Startup Therapy

Founders Need Finish Lines

Startups.com — Mon, 06 Apr 2026 07:31:06 -0700

Ever feel like you hit a milestone in your startup and immediately get handed the next problem? The episode explores why startup work rarely delivers a true sense of “done,” how founders get trapped by the arrival fallacy (believing the next round, milestone, or cushion will finally bring relief), and how the constant threat of being “eaten” by faster competitors turns ambition into paranoia. Ryan and Will compare the endless nature of startups to more finite work, discuss how chasing metrics and despising complacency fuels chronic restlessness, and share personal examples of goals that didn’t bring fulfillment. Their takeaway: startups are an infinite game, so founders need to create completion outside work—through finishable, tangible activities like cooking, workouts, sports, cleaning, or building projects—because completion is psychological maintenance, not a luxury.

What to listen for:
01:37 Goals vs Fulfillment
02:46 Arrival Fallacy Explained
03:42 Milestones Aren't Meaning
05:16 Dopamine and Restlessness
05:40 Painful Arrivals Stories
09:13 Despising Complacency
11:00 Getting Eaten Alive by Change
16:09 Contentment vs Career Metrics
18:24 Ad Break and Lamborghini Setup
19:22 Breaking Down The Fees
19:40 Paranoia About Losing It
20:30 Advice Comes With Bias
21:08 Founder Scarcity Mindset
22:54 Finding Completion Offline
26:32 Why Startup Wins Feel Empty
31:41 Small Finishes Refill The Tank
33:16 Buying Stuff Won’t Fix It
35:57 Appreciation Versus Earning
37:34 Manufacture Your Finish Line

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What Should My Expectations Be?

Startups.com — Mon, 23 Mar 2026 09:00:00 -0700

Ever feel like you’re working nonstop and still falling behind? The discussion argues founder happiness and decision-making improve fastest by recalibrating expectations, because “happiness = reality ÷ expectations.” Using stories from trading work for pizza or restaurant tabs to later winning massive business, it highlights how low expectations can make progress feel rewarding, while the “snowflake myth” and unpriced optimism create entitlement and disappointment. They distinguish aspiration (what you’d like) from expectation (what must happen), urging founders to replace unicorn fantasies with concrete, earned milestones like revenue, payroll, and product-market fit. They stress startups take far longer than most timelines claim—often 5–10+ years—even for legendary companies, and warn that funding timelines and social comparison can trigger panic and bad decisions.

00:37 Pizza Paper Hustle
01:41 Rib Money Origins
03:07 From Ribs to Lilly
04:30 Happiness Math Formula
05:59 Lambo Expectations Check
07:47 The Snowflake Myth
08:09 Optimism vs Expectation
09:19 IPO Odds Reality
10:53 Aspiration Not Debt
12:07 Milestones Over Unicorns
15:06 Time Myths and 3x Rule
17:36 Funding Clocks and Panic
20:42 Startup Mythology Trap
24:08 Five to Ten Year Truth
24:38 Overnight Success Myth
25:19 Funding Timeline Trap
26:01 Check Your Premises
26:54 Entitlement Mindset
28:19 Effort Versus Results
30:05 Earning Versus Inheriting
35:51 Milestones Not Home Runs
37:57 Small Wins Ladder
41:06 Expectations And Comparison

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What Actually Happens When A Founder Runs Out of Gas?

Startups.com — Mon, 02 Mar 2026 06:21:16 -0800

What do you think really happens if you burn out and step away for a minute? The conversation breaks down how founders often imagine an apocalyptic chain reaction—customers leaving, the team collapsing, investors panicking—when in reality burnout is a predictable capacity ceiling and most worst-case scenarios don’t happen. They argue the real danger is pretending burnout won’t come, pushing until physical failure, and keeping recovery secret, which can create the chaos founders fear. Using sports analogies, they emphasize that staying “on the field” nonstop makes you a liability, and that planned breaks build resilience, give teams room to step up, and help founders regain creativity and effectiveness. The core takeaway: treat recovery like required maintenance, plan for it, and build a company that doesn’t depend on you 24/7.

What to listen for:
00:57 Apocalypse Scenario
02:12 Always On Mentality
03:49 No Built In Breaks
06:56 Superman Plan Fails
08:06 Burnout Warning Signs
10:32 Atlas Shrugged Reality
15:22 Hockey Shift Lesson
16:23 Fear of Replacing Yourself
16:46 Stop Guessing Get Help
17:19 Burnout Nightmare Myths
19:14 When Investors Shrug
20:57 Youre Not The Main Character
23:24 Let The Team Step Up
25:14 Breaks Prevent The Crash
27:06 Vacation ROI Mindset
29:34 Plan Recovery Like Taxes
31:44 Durable Not Tireless
33:22 No Great Company Empty Tank

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

The Value of Distraction

Startups.com — Mon, 23 Feb 2026 07:03:53 -0800

What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re still figuring out what actually works. The hosts challenge the myth of the linear startup path, arguing that side quests—small, intentional experiments with capped downside—create learning, reduce single points of failure, and help you earn the right to pivot with evidence instead of vibes.

They share how Fundable’s early equity crowdfunding push revealed founders were unprepared to raise money, which led to a major side quest: doing diligence on about 100 companies, talking to 200+, and acquiring six venture-backed businesses—work that became the genesis of startups.com. Along the way, they highlight the value of the quest itself (market intel, understanding what not to do, faster learning) and even mention an extreme near-distraction: briefly considering buying Atari.

The conversation also reframes common “side quests” like doing services work while building a product, arguing that bringing in revenue to stay alive isn’t a distraction—it’s the business. They clarify the difference between a side quest (exploration) and a pivot (committing to a new direction), and point to the podcast itself as an example of a side quest that became a major long-term asset after a rough start.

What to listen for:
00:40 The AI Newsletter Moment That Sparked the Topic
01:47 What a “Side Quest” Means for Founders
03:45 The Myth of the Linear Startup Path
06:34 When Focus Becomes a Liability: Certainty, Ego & Roadmaps
10:04 Side Quests as the Ongoing Lab (and Why It Never Ends)
12:01 Case Study: Fundable 2012 and the Crowdfunding Gold Rush
15:48 The Pivot: Founders Needed Help, Not Just a Platform
18:07 Side Quests Done Right: Controlled Experiments (…and Almost Buying Atari)
18:42 The Wild Idea: Almost Buying Atari (Nostalgia vs. Distraction)
19:48 Why Side Quests Matter: Learning More Than the Outcome
20:42 Founder-Forward Deal Talks & Market Intel as a Force Multiplier
22:10 Side Quests as “Insurance”: Selling the Learning to Skeptics
23:48 The Classic Startup Side Quest: Services to Pay the Bills
27:14 Side Quest vs. Pivot: Exploration First, Commitment Later
27:52 The Podcast as a Side Quest That Became Core to the Business
30:26 Earning the Right to Pivot: Evidence, Courage, and Finding Truth
34:20 Closing: De-Risking Through Exploration + Startups.com Community Invite

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

Master Failure

Startups.com — Mon, 16 Feb 2026 04:19:22 -0800

What if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guaranteed to be wrong a lot. The goal isn’t to “be right,” it’s rapid error correction: make decisions, ship anyway, learn fast, and recover even faster. The conversation covers how avoiding failure leads to paralysis (“steering a parked car”), why indecision compounds in startups, and how to reduce risk by keeping failures small, reversible, and frequent (kill switches, stop rules, and capped losses). They share early personal stories—school fights and a childhood cattle business collapse—to show how overcoming real consequences builds confidence and resilience. Practical examples include choosing an ICP quickly, improving poor conversion rates through iteration, using vesting/cliffs when picking co-founders, and why even top VCs still miss constantly. The key takeaway: the most dangerous competitor is the one who isn’t afraid to get hit, recover, and keep coming back—because that’s as close to “invincible” as a founder can get.

What to listen for:
02:01 Failure Isn’t the Enemy: Stop Optimizing for Being Right
02:59 The Founder Reality: Uncertainty, Rapid Error Correction & the Boxing Analogy
03:44 Safety vs Startups: Why Most People Avoid the Risk
05:24 ‘Steering a Parked Car’: Indecision Kills Startups
07:54 Make the Call, Learn Fast: Small Failures, Big Truths
09:02 We’re Conditioned to Fear Failure (School, Work, Relationships)
11:59 Will’s Origin Story: Jason Barker and Learning to Beat the Monster
14:48 Choosing to Fail on Purpose: Turning Fear into a Superpower
17:06 Ryan’s First Big Failure: The Farm/Cattle Business Lesson Begins
17:45 Cash-Strapped Expansion: Inventory Leverage & a Brutal Winter
18:09 When the Side Hustle Needs a Side Hustle (and the Cost of Neglect)
18:35 Failing Hard at 12: Losing Animals and Learning to Plan
19:51 Founders Don’t Win by Being Right—They Win by Taking Hits
21:36 Shipping While Wrong: Marketing Experiments, MVPs, and Momentum
22:51 Hiring, Co-Founders & Investors: Why Nobody Can Pick Perfectly
24:00 The Real Skill: Recovering From Failure (Resilience as a Reflex)
30:26 Small Blast Radius, High Frequency: Reversible Bets & Kill Switches
31:13 Failure Is Portable: Building a House, Living ‘Why Not,’ No Regrets

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

We Can't Predict the Future Anymore

Startups.com — Mon, 09 Feb 2026 05:38:06 -0800

Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and investment in the startup ecosystem. Ryan Rutan and Will Schroter discuss the rapid pace of change brought by AI, including the exciting opportunities and the unsettling uncertainties. They explore how traditional pillars of business like hiring, marketing, and customer acquisition are being upended, creating both new challenges and avenues for innovative founders to thrive. Tune in to understand how to navigate this AI-driven landscape and leverage the chaos for maximum impact.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:00 Introduction and Future Predictions
00:49 The Impact of AI on Business Models
02:06 AI's Rapid Advancement and Market Disruption
04:17 Challenges in Marketing and Content Creation
10:04 Hiring and Talent Management in the AI Era
15:18 Product Development and Market Relevance
17:04 Industries Vanishing Overnight
17:32 The Accelerating Pace of Change
18:20 Investment in the Age of AI
19:07 The Future of Startup Funding
22:31 The Shrinking Moat of AI
24:54 Compounding Anxiety in the Startup Ecosystem
33:37 Founders: Built for Chaos
35:53 Embracing the Problem Business

We wanted efficiency. We got isolation.

Startups.com — Mon, 02 Feb 2026 05:02:37 -0800

How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized workflows on our humanity. We delve into personal anecdotes and discuss the ramifications of isolation in the workplace and the loss of shared experiences. We also contemplate the importance of reintroducing human interactions to ensure a balanced, connected, and more fulfilled work environment.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:31 The Loneliness of Optimized Efficiency
01:48 The Impact of Remote Work on Human Connection
04:14 The Rise of AI and the Decline of Human Interaction
12:41 The Evolution of Remote Work Culture
17:20 The Dystopian Reality of AI Conversations
20:22 The Importance of Laughter and Human Interaction
21:23 Leveraging GPT for Problem Solving
22:18 The Downside of Relying on AI
23:45 The Value of Human Interaction in the Workplace
25:09 The Impact of AI on Team Dynamics
27:04 Balancing Efficiency and Human Connection
29:05 The Future of Startups and Human Connection
30:33 The Need for Human-Centric Work Cultures
32:06 Conclusion: Embracing Humanity in the Age of AI

Are startups the future of employment?

Startups.com — Wed, 03 Dec 2025 04:51:15 -0800

What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big employment shifts, giving rise to smaller, more agile companies using AI tools. Drawing parallels with past technological revolutions, we highlight the opportunities that lower costs and new market demands present for founders. We discuss the transformation in various sectors, from customer service to content creation, and emphasize how AI can democratize entrepreneurship globally. Finally, we delve into the exciting potential for startup growth and the role of AI as both a tool and a transformative force in the startup ecosystem.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:24 The Impact of AI on Employment
01:16 Historical Parallels: Internet and Industrial Revolution
02:32 The Shift from Big Employment to Entrepreneurship
03:16 The Decline of Traditional Jobs
05:25 Opportunities in the New Economy
11:48 The Rise of the Creator Economy
20:15 Macro Trends and Future Outlook
23:52 The Rise of Billion-Dollar Startups
24:24 Price Collapse and Premium Experiences
26:01 The Impact of AI on Startups
26:44 The Creator Economy and Niche Markets
29:06 The Evolution of eSports
31:09 The Dawn of Young CEOs
33:22 The Future of Entrepreneurship
39:43 Global Entrepreneurship and Accessibility
45:56 The Age of the Startup

The Founder Hard Reset

Startups.com — Tue, 25 Nov 2025 04:49:10 -0800

Ever felt like vacations just aren't cutting it when it comes to startup burnout? In this episode, Ryan Rutan and Will Schroter dive deep into why burnout is inevitable for founders and how quick fixes like vacations often fail to address the root of the issue. They explore how to truly recover and maintain that all-important spark in your work. Learn why it's crucial to inventory what drains and fuels your energy, and how making meaningful changes—not just taking time off—can lead to sustainable recovery. Real-life examples and practical advice make this a must-listen for any founder feeling the grind.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:34 The Misconception of Business Success and Burnout
01:00 Personal Stories of Burnout
02:10 The Ineffectiveness of Vacations
03:49 The Importance of Meaning in Work
04:11 Personal Struggles with Burnout
07:27 The Real Cause of Burnout
10:23 Balancing Tasks to Prevent Burnout
11:59 The Battle Within: Struggles in the Workplace
12:58 Startup Expectations vs. Reality
13:46 Finding Energy and Avoiding Burnout
15:34 The Importance of Positive Energy
18:22 Active Breaks for Founders
22:32 Identifying and Addressing Burnout
25:31 Join the Startups.com Community

Is there a line between Founder optimism and delusion?

Startups.com — Mon, 17 Nov 2025 09:00:00 -0800

Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explores how belief against all odds drives entrepreneurs forward. They explain how maintaining optimism is not just about having a positive outlook but about creating momentum from minor wins and leveraging chaos as an opportunity. The hosts also address the fine line between optimism and dishonesty, emphasizing the importance of an 'educated wish.' Whether you're battling to raise funds or struggling to maintain morale, this episode delves into why a founder’s unyielding belief is crucial for startup survival and growth.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:07 The Delusional Optimism of Founders
01:02 Creating and Living in a Fantasy
02:00 Running Toward Chaos
04:54 The Passion and Drive of Founders
05:59 The Reality of Startup Life
12:08 The Role of Belief and Proof
14:31 Finding Optimism in Small Wins
16:40 Persistence in the Face of Rejection
18:56 The Power of Hope in Business
19:52 The Role of Optimism in Startups
21:41 Balancing Optimism and Honesty
23:03 The Fine Line Between Optimism and Deception
26:07 The Importance of Optimism in Leadership
28:55 The Role of Optimism in Overcoming Challenges
32:05 The Founder's Mindset: Manufacturing Optimism

Prioritize Productivity Over Popularity

Startups.com — Fri, 07 Nov 2025 03:07:15 -0800

Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily translate to business traction. Will Schroter shares a cautionary tale from his own experience, revealing how his focus on brand-building and networking kept him from truly building his company. We explore the fine line between personal branding and productivity, and why many founders need to prioritize the latter to achieve real success. It's a reminder that until your product and business are fully developed, every external interaction could be costing you more than it's worth.

00:30 The Trap of Visibility: A Personal Story
02:24 The Illusion of Popularity vs. Productivity
06:21 The Modern-Day Equivalent: Social Media
09:24 Balancing Publicity and Productivity
11:23 Cautionary Tales and Lessons Learned
12:55 The Importance of Focus and Balance
14:48 Earning the Right to Brand Build
15:29 The Pitfalls of Prioritizing Popularity Over Business
16:07 The Honeymoon Period of Venture Funding
17:40 The Dangers of Personal Branding for Founders
18:47 When Personal Views Hurt Business
21:39 Balancing Personal and Company Brand
23:48 Focus on Building the Business First
30:22 The Cost of External Interactions

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

Better is Better than Bigger

Startups.com — Mon, 27 Oct 2025 10:00:00 -0700

Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company worse, not better. Ryan and Will discuss the trade-offs between size and quality, using examples like Google and PayPal. They explore how rapid growth can diminish company culture, slow down decision-making, and introduce inefficiencies. The conversation also covers personal experiences in startup growth, emphasizing the importance of optimizing for better rather than just bigger. Whether it's adding more staff or raising capital, they advocate for making decisions that enhance company quality and founder life satisfaction.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:14 The Myth of Bigger is Better
00:43 Examples of Companies That Grew and Suffered
02:00 The Hidden Costs of Scaling
05:08 Personal Experiences with Growth Challenges
13:01 The Importance of Freedom and Quality
17:18 The Hidden Costs of Growth
17:58 Balancing Growth and Quality of Life
20:39 Defining Non-Negotiables for Better Business
22:33 Scaling with Soul: Maintaining Company Culture
24:41 Quality Over Quantity: Making Strategic Decisions
28:07 The Power of Saying No
31:15 Sticking to Your Values for Sustainable Growth

Founder Authenticity: Use with Caution

Startups.com — Wed, 22 Oct 2025 02:39:46 -0700

Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts where pure honesty works, to sharing personal anecdotes about navigating the consequences of unfiltered truth, this episode unpacks how transparency can impact your team, brand, and personal relationships. Find out why being your true self might only be great advice 6% of the time and how effective communication can save you from unintended fallout.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
01:01 The Consequences of Unfiltered Honesty
01:26 Generational Differences in Professionalism
02:44 The Power Dynamics of Founders
04:45 Balancing Honesty and Diplomacy
06:01 The Luxury of Honesty and Risk
08:04 The Importance of Filtering Communication
12:56 The Duality of Professional Personas
15:21 The Consequences of Honesty in Leadership
16:19 Balancing Honesty and Diplomacy
17:10 The Importance of Empathy in Communication
18:26 The Cost of Unfiltered Honesty
19:51 Frameworks for Effective Communication
20:55 Lessons from the Terminator: Choosing Responses Wisely
22:07 The Role of Diplomacy in Leadership
28:17 The Medium Matters: Hot, Warm, and Cold Communication
29:56 Prioritizing Outcomes Over Authenticity

Founders, Embrace Your Flaws

Startups.com — Tue, 14 Oct 2025 06:41:28 -0700

Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and their founders are loaded with problems, some of which aren't really 'problems' at all but hidden superpowers. From obsessive tendencies to ADHD, they discuss how to harness these traits for success rather than trying to fix them. Drawing from personal experiences and industry insights, they touch on the influence of pharmaceutical marketing, the role of social media in shaping perceptions, and the importance of finding context for your strengths. This episode challenges you to rethink how you view your weaknesses and offers a fresh perspective on founder self-acceptance and leveraging inherent traits for entrepreneurial success.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:33 Founders and Their Problems
01:15 Pharmaceutical Industry Insights
02:36 Social Media and Problem Creation
03:46 Personal Struggles of Founders
05:07 Overthinking and Control Issues
11:15 ADHD and Academic Challenges
17:11 Harnessing Obsessiveness for Success
20:40 Evaluating Self-Help Advice
21:09 Struggles with Attention Span
21:31 Learning Outside Traditional Education
22:15 Emphasizing Strengths Over Weaknesses
23:29 Founders and Their Strengths
28:08 Anxiety as a Superpower
34:46 The Importance of Context in Learning
38:36 Self-Acceptance and Utilizing Strengths

Is Remote Culture, Actually Culture?

Startups.com — Mon, 06 Oct 2025 07:51:31 -0700

Have you ever wondered if remote work is better than being in the office? Ryan and Will dive into their experiences and how their work culture has evolved over 20 years. They discuss the pros and cons of remote work, the importance of autonomy, and how remote setups have stripped away some of the overhead, revealing who truly thrives in this environment. They also explore whether it's possible to create a strong company culture remotely and how the shift has amplified the best and worst in employees. Tune in as they break down their journey from being die-hard office goers to embracing the flexibility and autonomy of remote work.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:36 The Shift from Office to Remote Work

01:01 Challenges of Remote Work

01:57 Socialization and Remote Work

04:42 Remote Work Rituals and Failures

07:26 Digital Culture and Transactional Work

12:06 Evolving Company Culture

19:14 The Evolution of Workplace Culture

19:34 Starting Fresh: Can We Be Transactional?

20:20 The New Culture: Autonomy and Responsibility

21:37 Balancing Work and Personal Life

23:49 The Value and Challenges of Remote Culture

25:34 Autonomy: The Ultimate Compensation

26:10 Remote Work: Amplifying Strengths and Weaknesses

32:13 The Social Aspect of Work

37:22 The Future of Work: Remote vs. In-Office

Can I Hand Off My Startup?

Startups.com — Mon, 29 Sep 2025 06:13:28 -0700

Ever dreamt of handing off your startup to a killer operator and sipping margaritas while the money keeps rolling in? It sounds perfect, but reality often has other plans. In this episode, we break down why passing on the reins isn't as smooth as it seems—from the slow degradation of everyday tasks to the irreplaceable instinct and urgency a founder brings. Discover why certain roles and tasks can be handed off successfully while others, like maintaining culture and strategic vision, often falter without the founder's unique touch. Tune in for practical advice on what you can actually hand off and what you should keep a close eye on to keep your startup thriving.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:06 The Dream of Handing Off a Startup
00:54 Early Days and Initial Success
02:14 The Startup Dream and Its Challenges
03:47 The Reality of Handing Off a Startup
05:09 The Slow Decline: Signs and Symptoms
07:48 Personal Experiences and Lessons Learned
17:00 The Boiled Frog Syndrome
19:45 The Timeless Nature of Startup Challenges
20:25 The Disconnect Between Perception and Reality
20:53 The Unique Metabolism of Founders
22:06 The Importance of Ownership and Passion
25:01 Handing Off Responsibilities: What Works and What Doesn't
27:43 The Irreplaceable Elements of Leadership
32:58 The Impact of Founder Presence on Company Culture
39:06 The Inherent Urgency of Founders

Did I Just Get Promoted or Fired?

Startups.com — Mon, 22 Sep 2025 09:00:00 -0700

Ever wonder what happens when a founder gets 'promoted' out of the CEO role? Ryan and Will dive into the tricky terrain of founder transitions, exploring how it feels to be nudged into roles like Chief Vision Officer or Chairman—positions that often come when a new CEO is brought in. They discuss the emotions involved, the motivations of investors, and the strategies for turning this awkward moment into an opportunity. Whether you're in the thick of this situation or just want to be prepared, this episode provides valuable insights on maintaining dignity, negotiating effectively, and leveraging a graceful exit for future success.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:24 The Founder Promotion Dilemma
01:07 Personal Experience with Founder Titles
02:26 The Gary Coleman Effect
03:21 The CEO Replacement Backfire
05:29 The Emotional and Financial Impact of Founder Reassignment
10:44 Board Mechanics and Founder Control
13:06 Investor Strategies and Founder Leverage
18:34 Facing the Reality of Founder Reassignment
23:17 Famous Comebacks: Steve Jobs, Howard Schultz, and Jack Dorsey
24:36 The Emotional Toll of Being Replaced
25:10 Turning Emotions into Positive Actions
25:46 Negotiating Your Exit Strategy
30:54 Crafting Your New Role
31:55 The Importance of Maintaining Relationships
37:00 The Worst and Best Case Scenarios

Burnout is a Treatable Injury

Startups.com — Mon, 15 Sep 2025 06:19:49 -0700

Ever felt like burnout is inevitable in your startup journey? You're not alone. Burnout can feel like a silent co-founder, but it doesn't have to signal the end of your entrepreneurial story. In this episode, we discuss why burnout happens, how to diagnose it, and most importantly, how to treat it. Discover the importance of pacing yourself, the hidden costs of burnout, and why taking a break is crucial—not just for you, but for your entire team. We'll share personal anecdotes, practical tips, and the value of stepping away to recharge, so you can return stronger and more passionate than ever. Tune in to learn how to recognize the signs of burnout and create a treatment plan that works for you and your startup.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
01:01 Personal Burnout Stories
04:46 The Hidden Costs of Burnout
08:41 Recognizing and Addressing Burnout
19:17 Recognizing Emotional Burnout
19:47 Impact of Economic Downturn on Founders
21:19 Personal Struggles and Their Impact on Work
22:13 Diagnosing and Addressing Burnout in Teams
23:04 The Importance of Personal Life in Preventing Burnout
27:32 Strategies for Treating Burnout
29:27 Finding Passion Outside of Work
32:59 Identifying and Mitigating Burnout Triggers
38:25 The Role of Leadership in Managing Burnout

Stop Pretending You Don't Have Enough Time!

Startups.com — Wed, 10 Sep 2025 07:09:56 -0700

Ever feel like you need more hours in the day? Turns out, you don't. In this episode, we dive deep into time management for founders, starting with a viral Reddit post that stirred some controversy. We'll explore how compressing your timelines can lead to greater efficiency and free up your schedule for the things that truly matter. Forget the chronic meeting bloat and endless email chains; it's all about optimizing every minute. Discover how focusing on small, incremental tasks can lead to significant progress, both in your professional and personal life. Whether you're a solo founder or leading a team, this episode offers actionable insights to make the most out of your 24 hours.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:26 The Reddit Experiment: Stirring Controversy
03:53 The Time Compression Revelation
04:32 Analyzing Time Management
07:52 The Cost of Meetings and Conversations
15:21 The Impact of Family on Work Hours
17:44 The Power of Constraints
20:02 The Power of Saying No
20:24 Focus as a Job
20:34 Timeless Solutions
21:06 The Importance of Prioritization
21:34 Efficiency in Communication
22:34 Breaking Down Big Tasks
23:14 Consistency and Compounding
23:25 Building a House with Focus
26:53 Weekly Timelines for Productivity
36:12 Reclaiming Time for Personal Use

Are Founders Aligned with Those Around Them?

Startups.com — Tue, 02 Sep 2025 05:41:10 -0700

The complexities of alignment among founders, employees, and even spouses. They debunk the notion that perfect alignment exists, emphasizing that often, perceived alignment is more fiction than reality. The conversation covers the inevitable differences in expectations, contributions, and risk tolerances that arise between co-founders and employees. The hosts also delve into the personal side, exploring how founders' professional decisions impact their relationships at home. Through candid anecdotes and practical insights, they highlight the importance of mutual respect and understanding in managing these fundamentally misaligned expectations in both business and personal life.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:42 The Myth of Alignment in Startups
01:06 Investor Alignment: Fact or Fiction?
01:48 The Role of Spouses in Startup Alignment
03:09 The Challenge of Aligning with Employees
04:59 Generational Differences in Work-Life Balance
14:50 The Reality of Co-Founder Alignment
21:16 The Challenge of Co-Founder Alignment
22:45 Spousal Support and Startup Life
25:45 Understanding and Managing Differences
28:31 The Myth of Perfect Alignment

Will the Payout be Worth the Sacrifice?

Startups.com — Mon, 25 Aug 2025 09:00:00 -0700

The challenging question of whether the sacrifices made in pursuit of entrepreneurial success are ultimately worth the payoff. Will retells his personal story of almost buying an expensive house in Bel Air only to realize, thanks to his wife's intervention, that it wasn't what he truly wanted. The duo explores themes of sacrifice, payoff, and how aligning personal goals with true desires can lead to genuine happiness and fulfillment. Whether it's the freedom to travel or the joy of creating something with your hands, this episode urges founders to carefully contemplate their end goals and ensure their sacrifices lead to meaningful rewards.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:25 The Beverly Hills House Dilemma
03:05 Reflecting on Sacrifices and Payoffs
06:52 The Decision to Move Back to Ohio
13:42 The Value of Freedom and Purpose
17:46 The Danger of Undefined Goals
22:15 The Illusion of Goals
23:19 Realizing Unwanted Desires
24:13 Shifting Ambitions
26:21 The Fear of Losing Ambition
27:54 Evaluating Sacrifices
33:48 Finding True Fulfillment
36:31 Building a Dream
42:38 Advice for Founders

How Founders Blow Their Fortunes

Startups.com — Tue, 19 Aug 2025 08:33:39 -0700

The critical do's and don’ts after a big financial win as a startup founder. They emphasize the importance of not oversharing about your wealth, shifting from an offensive to a defensive mindset, preserving your gains, and being cautious about new investments. They also explore how to handle the psychological and social challenges that come with newfound success, using real-life examples and practical advice to ensure you don't blow your hard-earned money.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:52 The Myth of the Big Exit
01:52 Emotional and Psychological Impact of Wealth
02:58 The Speech: Congrats, Now Don't Mess It Up
04:23 Financial Management for Newfound Wealth
06:11 The Three Js of Wealth: Judgment, Jealousy, and Jockeying
06:47 The Importance of Keeping Financial Information Private
20:06 The Shift from Offense to Defense in Wealth Management
22:24 The Founder Mentality Shift
23:53 The Casino Analogy
26:45 The Importance of Playing Defense
30:18 The Danger of Proving Yourself Again
36:33 The Save Point Strategy
44:19 The Burn Rate Dilemma
45:24 Conclusion: Preserving Your Wealth

When is Enough, Enough?

Startups.com — Mon, 11 Aug 2025 09:00:00 -0700

Ryan and will talks about a critical issue many founders face: knowing when to say 'enough is enough.' They explore the constant pursuit of growth both personally and professionally and how it can turn into a liability if not checked. They dive into the psychological roots of why founders struggle with the concept of 'having enough,' the impact of a scarcity mindset, and the importance of recognizing diminishing returns. The hosts share personal anecdotes and offer practical advice on how to balance ambition with fulfillment, emphasizing the need for diversified 'buckets' of happiness beyond just business success.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:07 The Founder’s Dilemma: Knowing When Enough is Enough
01:26 The Scarcity Mindset and Its Impact
02:35 The Law of Diminishing Returns
03:12 Personal Anecdotes on Ambition and Satisfaction
05:38 The Concept of Utility in Economics
12:00 Balancing Growth and Happiness in Startups
16:56 Post-Exit: The Risk of Overreaching
20:11 The Downfall of a Legend
21:15 The Cost of Ambition
22:32 The Utility of Wealth
23:25 Chasing More: A Founder’s Dilemma
25:42 The Search for True Happiness
28:48 Redefining Success
33:50 Balancing Ambition and Value

Can Entrepreneurship Alleviate Poverty?

Startups.com — Mon, 04 Aug 2025 09:00:00 -0700

How entrepreneurship can transform lives and communities? Will shares his personal journey from a challenging childhood to becoming a successful entrepreneur. They explore whether entrepreneurship can be a means to alleviate poverty, emphasizing the importance of hope, a safety net, and access to education and mentorship. The conversation dives deep into the potential impact of entrepreneurial initiatives on economic development and the need for structured support to foster entrepreneurial success on a global scale.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:40 The Power of Entrepreneurship to Alleviate Poverty
01:17 Personal Stories of Entrepreneurial Beginnings
02:34 The Ripple Effect of Entrepreneurship
03:38 Teaching Entrepreneurship as a Lifelong Skill
04:46 Hope as the Foundation of Entrepreneurship
05:37 Early Wins and Their Impact
07:17 The Importance of Small Wins
08:20 The Role of Hope and Pride in Entrepreneurship
12:15 The Willingness to Fail
22:49 The Risk of Failure for the Broke
23:45 Historical Context and Immigrant Success Stories
24:46 The Luxury of Credit and Capital
27:03 Entrepreneur Welfare and Venture Capital
29:14 The Case for Minimum Basic Income for Founders
29:40 The Parallel with Education and FAFSA
38:47 The Need for Structured Entrepreneurship Education
39:47 The Role of Hope and Security in Entrepreneurship
45:46 Entrepreneurship as a Solution to Poverty
47:34 Join the Startups.com Community

Should Startups Be a Family?

Startups.com — Mon, 28 Jul 2025 08:31:03 -0700

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges and dynamics of blending friendship and professionalism in startups. They delve into the potential pitfalls of treating your startup team like a family, the consequences on both founders and employees, and the importance of setting clear boundaries. They highlight shared experiences from their early careers and emphasize the need for empathy, respect, and a professional approach to lead effectively without compromising authority.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:08 The Illusion of Startup as a Family

00:55 Early Career and Peer Dynamics

01:50 The Reality of Founder-Employee Relationships

03:46 The Pitfalls of Treating Employees as Family

05:54 Transparency in Startups: A Double-Edged Sword

07:13 Shared Risk and Misinterpreted Bonds

09:32 The Inevitable Strain on Relationships

12:17 The Limits of Friendship in Startups

16:18 The Evolution of Team Dynamics

18:12 A Throwback to Early Company Culture

18:31 The Impact of a New Hire

19:19 Cultural Misalignment and Realization

20:15 Adjusting Company Culture

21:43 Balancing Professionalism and Empathy

22:50 The Importance of Boundaries

24:18 The Dangers of Forced Inclusivity

28:24 Personal Experiences with Cultural Fit

32:20 The Family vs. Professional Sports Team Metaphor

36:42 Final Thoughts on Company Culture

Can Founders be Replaced by AI?

Startups.com — Mon, 21 Jul 2025 09:00:00 -0700

Ryan and Will talk about the growing role of AI in startups. They explore how AI is automating traditional founder tasks like writing, coding, and analyzing data. The conversation delves into the existential threat AI poses to the founder's role and how founders can adapt to this new landscape. They argue that founders should embrace AI to focus on creativity, curation, and leadership rather than being bogged down by routine tasks. The episode underscores the importance of evolving with technology to enhance productivity and innovation, ultimately redefining the founder's job description for the future.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:34 Can AI Replace Founders?
01:16 The Evolution of AI Capabilities
02:03 AI's Impact on Copywriting and Creativity
03:28 AI in Advertising and Idea Generation
04:44 Embracing AI for Efficiency
06:31 AI as a Force Multiplier
09:44 The Future of AI and Founders
14:36 AI in Coding and Development
17:08 Leveraging AI for Business Growth
19:13 Simulating Business Scenarios with AI
19:38 The Role of AI in Business Decision Making
19:53 The Timeless Nature of Business Challenges
20:48 Embracing AI for Efficiency
21:12 The Unique Human Element in Business
23:40 The Future of Founders in an AI-Driven World
25:50 The Evolution of Founders' Roles
28:05 Leadership and Determination in Business
30:47 The Importance of Vision and Adaptability

What if we run out of goals?

Startups.com — Mon, 30 Jun 2025 09:00:00 -0700

In this episode of the Startup Therapy Podcast, Ryan and Will talk about what happens when you hit all your big goals and realize there might not be any more mountains left to climb. They discuss the complex feelings and identity crises that can emerge when success is achieved, and reflect on how to find new meaning and satisfaction beyond traditional goal-setting. The conversation touches on personal anecdotes, the concept of enjoying the process, and how to appreciate the journey in a fulfilling way.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:27 The Identity Crisis of Achieving Goals
01:05 Personal Reflections on Goal Setting
02:25 The Evolution of Goals Over Time
04:14 The Reality of Achieving Big Goals
07:04 The Trap of Sensationalizing Goals
10:58 The Diminishing Returns of Goal Achievement
19:06 The Two Paths of Goal Setting: Pleasure vs. Pain
20:40 Understanding Pain and Relief
21:42 The Myth of Success Equals Happiness
22:32 Existential Goals and Realizations
23:31 The Challenge of Finding Fulfillment
25:23 Enjoying the Journey vs. The Destination
29:12 Reevaluating Ambitions and Goals
33:11 Building for the Sake of Creation
36:59 Infinite Games and Lifelong Pursuits

Founders, Reinvention IS your Constant!

Startups.com — Mon, 23 Jun 2025 08:27:40 -0700

Will and Ryan talk about the fascinating and often overlooked journey of reinventing oneself. Will shares his diverse background, from being an ad guy to becoming a multi-time startup founder, and stresses the importance of embracing various roles to build a comprehensive skill set. The duo emphasizes that becoming a founder isn't a job you get hired for but one you create yourself. They explore how personal and professional reinvention can be the key to success in the startup world, encouraging founders to see themselves as a composite of their varied experiences. The episode is filled with personal anecdotes, practical advice, and an inspiring message: you are not confined to one identity or role — your potential is ever-evolving.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:43 The Journey to Becoming a Founder
01:28 Reinventing Yourself as a Founder
02:31 The Value of Diverse Experiences
03:55 A Humorous Job List
08:11 The Role of Exposure in Career Choices
13:06 Breaking Free from Career Constraints
19:46 Early Career Hustles
20:22 Learning from Experience
20:53 First Sales Job
21:30 Unexpected Opportunities
23:22 Reinvention Starts Small
24:06 Curiosity and Career Growth
26:14 Building Skills Over Time
28:04 The Power of Starting Small
30:10 Embracing Continuous Learning
32:21 The Value of Diverse Experiences
39:59 Reinventing Yourself as a Founder

Founder Isolation is Getting Worse

Startups.com — Mon, 16 Jun 2025 09:00:00 -0700

Ryan and Will talk about the growing isolation that founders are feeling despite having more ways to connect. They delve into how the shift to remote work, the impact of social media, and the rise of AI have contributed to stripping away the humanity from our daily interactions. They share personal experiences and offer insights into why this sense of loneliness has worsened, and most importantly, explore actionable steps founders can take to reconnect, feel less isolated, and build meaningful relationships in an increasingly digital world.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
01:05 The Paradox of Connection and Loneliness
02:36 Impact of Remote Work on Founders
16:17 The Role of Social Media in Isolation
20:49 The Distorted Reality of Social Media
21:24 The Cynicism Towards Social Media Posts
22:19 Creating Private Spaces and Personal Connections
23:15 Declaring Relationship Bankruptcy
26:53 The Impact of AI on Authenticity
31:08 The Future of Human Interaction in a Digital World
35:33 Combating Isolation as Founders

Forging Founder Confidence

Startups.com — Mon, 09 Jun 2025 08:31:04 -0700

Ryan and Will discuss the journey of becoming a confident founder. Celebrating their 300th episode, they reflect on how learning to lead and building confidence starts with curiosity. They emphasize asking questions, even seemingly silly ones, to gain knowledge and confidence. Will and Ryan also dive into the importance of challenging oneself incrementally and being willing to make mistakes as key steps in growing confidence. They share personal anecdotes and practical advice, making a case for bravery, perseverance, and learning from failures. Perfect for any founder grappling with self-doubt or seeking actionable steps to boost their confidence.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:58 Building Confidence Through Practice
05:25 The Power of Curiosity
09:25 Asking the Right Questions
14:58 Taking on New Challenges
19:03 Building Confidence Through Small Victories
19:40 Teaching Kids Micro Challenges
20:09 Challenging Yourself Incrementally
21:17 The Line Between Ambition and Recklessness
22:19 Learning Through Incremental Steps
25:37 The Importance of Being Wrong
27:41 Building Confidence as a Founder
31:33 The Role of Bravery in Confidence

Is College a Waste of Time for Founders?

Startups.com — Mon, 02 Jun 2025 09:00:00 -0700

In this episode of The Startup Therapy Podcast, Ryan and Will discuss the true value of a college education for aspiring entrepreneurs. They explore whether the traditional path through higher education is the best route for those determined to start their own businesses. With personal anecdotes and economic insights, they argue that college may not always be the ideal path for founders, emphasizing the benefits of real-world experience and early entrepreneurial efforts. They also discuss societal expectations, financial implications, and alternative approaches to gaining the necessary knowledge and skills.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:17 The Value of a College Degree for Founders
00:55 Challenging the College Norm
01:37 A Real-Life Example: Skipping College for Startups
03:14 Generational Expectations and College
07:25 The Economics of College Education
08:04 The Financial Impact of College vs. Investing
14:19 The Opportunity Cost of College for Founders
20:21 The Power of Compounding Experiences
20:35 Learning at Your Own Pace
20:58 The Irrelevance of Traditional Education
22:19 Founders Need a Broad Skillset
22:57 The Limitations of College
24:33 Alternative Learning Paths
25:57 The Value of Practical Experience
27:44 The Diminishing Value of a College Degree
29:13 Questioning the College Path
33:30 The Founder Mindset
40:18 Restarting the Conversation on Education

Are We Preventing Our Startup From Evolving?

Startups.com — Mon, 26 May 2025 07:26:40 -0700

The realities of evolving a startup. Ryan and Will discuss how the first idea is rarely the final solution, sharing insights on how to navigate the pivoting process. Using Uber and their own experiences at startups.com as examples, they explore the dangers of clinging to an initial plan and the importance of staying open to change. They also touch on overcoming ego, internalizing market feedback, and avoiding self-sabotage to ultimately achieve a more successful and fulfilling business.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:51 The Myth of the Perfect Plan
02:04 The Uber Example: Evolving Business Models
03:55 The Importance of User Feedback
04:48 Facing Investor Expectations
07:44 Ego vs. Agility in Decision Making
08:47 The Afford It Story: Lessons Learned
13:21 Conclusion and Final Thoughts
13:53 The Original Plan and Its Challenges
14:25 Admitting Mistakes and Moving Forward
15:10 Evolving as a Founder
15:58 The Birth of Startups.com
17:26 Learning from Market Feedback
20:45 Detaching Ego from the Product
23:14 The Importance of Adaptation

Building a Startup That Loves You Back

Startups.com — Mon, 19 May 2025 06:18:55 -0700

Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Will shares an incredulous story about a friend enjoying a Tuesday afternoon in the pool, leading to a broader discussion on the importance of setting boundaries and recognizing the signs of burnout. The hosts emphasize the need for self-awareness, prioritizing personal values, and finding joy in the journey, not just the destination. They also touch on the benefits of giving team members autonomy and creating a supportive, non-toxic work culture.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:32 The Pool Story: A Lesson in Work-Life Balance
02:08 The Toxic Relationship with Work
03:11 Startup Therapy: The Podcast's Origin
08:15 Balancing Work and Family
13:17 Non-Negotiables and Personal Values
14:51 Conclusion and Final Thoughts
15:35 Mitigating Guilt Through Productivity
17:29 The Elusive Goal of Profit
19:21 Emotional ROI in Startups
21:57 Autonomy and Company Culture
24:50 Balancing Safety and Happiness
28:26 Avoiding the Trap of Obligations
29:40 Creating a Non-Abusive Startup Relationship
30:50 Join the Startups.com Community

When Our Friends Resent Our Success

Startups.com — Mon, 12 May 2025 07:49:48 -0700

Ryan and Will discuss the surprising reactions founders often face when they achieve success. They explore how unexpected resentment from friends and peers can arise, why it happens, and how to navigate these tricky social waters. Through personal anecdotes and practical advice, they delve into balancing humility and openness about success while staying true to oneself. Tune in to learn about managing relationships as you climb the ladder and handling the inevitable pushback with grace.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:31 The Unexpected Reactions to Success
02:54 Personal Stories of Resentment
07:57 The Impact of Success on Relationships
12:32 Social Media and Validation
14:01 Processing Success and Insecurities
19:34 Navigating Conversations About Success
21:04 The Validation Loop Dilemma
21:21 Caring About Others' Opinions
21:57 The Spectrum of Self-Presentation
23:17 The Insecurity Behind Social Media Influencers
25:34 The Cost of Flaunting Success
29:04 Extreme Humility and Its Consequences
32:19 Balancing Humility and Pride
37:01 The Art of Humble Bragging
40:39 Avoiding Resentment Through Humility
41:46 The Power and Responsibility of Success
42:38 Join the Startups.com Community

When Our Startup Outgrows Us

Startups.com — Sat, 10 May 2025 02:00:23 -0700

In this episode of the Startup Therapy Podcast,Ryan and Will delve into the emotional journey of startup founders who feel out of place in the very companies they built from scratch. They discuss the guilt and struggle founders experience when their roles change and they no longer enjoy their jobs. They share personal anecdotes and examine the impact of forced roles, from management misfits to a loss of personal fulfillment. The duo also explores the concept of evolving with or beyond your startup, and how to come to terms with these difficult but often necessary transitions.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:48 The Shift from Building to Managing

01:29 The Struggles of Management

02:13 The Evolution of Roles

04:17 The Peter Principle in Action

05:29 The Emotional Toll of Management

08:34 Reflecting on the Past and Moving Forward

09:57 The Realization and Acceptance

12:39 The Dilemma of Founder Evolution

13:10 Learning from the Past

13:42 Commitment and Introspection

15:02 The Cost of Doing What You Hate

17:40 Recognizing and Embracing Change

20:16 The Hard Decision to Move On

25:03 Celebrating Growth and Moving Forward

When Being in the 1% Feels like Failure

Startups.com — Mon, 28 Apr 2025 21:04:48 -0700

Ryan and Will discuss the psychological challenges founders face by constantly looking ahead and rarely celebrating their achievements. They explore how important it is for founders to practice gratitude and recognize their progress, even if their ultimate goals haven't been reached. The conversation delves into personal experiences, including Ryan's move to Guatemala and Will's time in Beverly Hills, highlighting how perspective and gratitude can significantly impact one’s satisfaction and motivation in their entrepreneurial journey.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:29 The Psychological Cost of Milestones
00:58 The 1% of Startups
02:01 Celebrating Small Wins
02:38 The Comparison Trap
03:45 Balancing Credit and Complacency
04:33 Contrasting Success Stories
09:14 Perspective on Startup Success
16:26 The Olympic Mindset and Startup Mentality
17:39 The Power of Perspective and Gratitude
19:35 Balancing Ambition and Gratitude
21:16 Family Traditions and Simple Joys
22:47 Reinforcing Self-Worth and Capability
28:19 The Curse of the Exited Founder
31:02 Changing Perspectives for Greater Happiness

We Need Outside Interests that Consume Us

Startups.com — Mon, 21 Apr 2025 06:44:43 -0700

Dive into the common struggle founders face with burnout and the inability to truly relax. Ryan and Will share their personal experiences and discuss how traditional relaxation methods often fail for them. Instead, they highlight the importance of finding other meaningful and challenging obsessions outside of work to channel their energy. From woodworking and home-building to martial arts, they explore how these activities can provide a sense of accomplishment, progression, and actual mental rest, ultimately making them better and more effective in their startup journeys. Tune in to gain insights on how to recharge as a founder by embracing big, consuming projects that challenge and fulfill you.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:44 The Struggle with Relaxation
01:36 Failed Attempts at Relaxation
03:32 Vacation Dilemmas
05:52 The Need for Mental Engagement
09:47 The Importance of Completion
14:07 Finding New Problems to Solve
22:10 Woodworking as a Solution
24:13 The Obsession Begins: From Birdhouses to Building a House
24:48 The Challenge of Building a House from Scratch
25:35 Balancing Work and Passion Projects
26:31 The Importance of Completion and Physical Activity
27:53 Managing Overwhelm and Finding Solutions
29:14 The Power of Small, Consistent Efforts
30:22 The Role of Meaningful Side Projects
33:17 The Need for Mental and Physical Challenges
36:21 The Value of Overwhelming Projects

You probably should be TERRIFIED. At least a bit..

Startups.com — Mon, 14 Apr 2025 21:00:00 -0700

Ryan and Will discuss the prevalent fear in the market due to economic uncertainty in April 2025. They delve into how fear is a constant companion for founders and argue that it's not a weakness but a strength. Drawing on personal experiences, including public speaking and risky business moves, they illustrate how leaning into fear can drive massive growth and success. Comfortable activities rarely lead to significant achievements, they argue, emphasizing that true progress requires embracing discomfort. They also highlight the importance of conditioning oneself to fear and rejecting complacency to ensure continuous growth and impactful outcomes.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:35 Founders' Relationship with Fear
01:35 Fear as a Motivator and Asset
02:38 Personal Experiences with Fear and Risk
03:17 Balancing Risk and Reward in Decision Making
06:36 The Role of Fear in Entrepreneurship
07:05 Cultural Differences in Risk Perception
12:57 Embracing Fear as Part of the Job
14:55 Building Resilience Through Failure
15:39 Embracing Fear in Business
16:02 The Role of Fear in Motivation
17:46 The Danger of Complacency
19:25 Taking Big Risks for Big Rewards
21:23 Balancing Fear and Progress
25:44 Facing Public Speaking Fears
30:08 The Importance of Leaning Into Fear

Make Money First - Then Make a Product

Startups.com — Mon, 07 Apr 2025 07:37:37 -0700

In this episode, Ryan and Will discuss the common misconception that startups need funding before generating revenue. They emphasize that the actual business isn't just the product but the revenue it generates. The discussion covers various strategies to bootstrap and generate cash flow, including building a minimal viable product, offering related services, and even taking on side gigs or unconventional methods to bring in money. By doing so, startups can extend their runway and better validate their business model before seeking significant investment. The episode includes examples from famous startups like Zappos and Airbnb to illustrate these points.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:|
00:51 The Broken Assumption About Funding
01:29 Generating Revenue Before the Product
02:39 Examples of Early Revenue Generation
03:07 The Zappos Story: Validating Demand
08:06 Personal Anecdotes on Testing Demand
10:27 The Importance of a Minimum Viable Product
18:39 Service-Based Proxies for Products
21:21 The Unexpected Success of Pitch Deck Services
22:04 Assumptions About Entrepreneurs and Investors
23:48 The Role of Services in Startup Success
25:33 The Importance of Revenue and Profitability
28:53 Creative Ways to Fund Your Startup
34:10 The Value of Bootstrapping and Hustle

It's really HARD to REPEAT A WIN

Startups.com — Mon, 31 Mar 2025 17:24:21 -0700

Will and Ryan discuss the dangerous mindset founders can fall into after hitting it big with their startups. They reflect on the story of Peter Chesky, co-founder of Wish, who became a billionaire during the tech IPO boom of early 2021 but saw his net worth plummet as the company's stock tanked. The episode emphasizes the importance of treating any major payout as if it's the last one you'll ever receive. With only a small percentage of startups ever having significant exits, and even fewer doing it repeatedly, Ryan and Will stress why founders should be cautious with their newfound wealth instead of assuming it will keep flowing.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

01:01 The Rise and Fall of Wish
03:01 Lessons from the Wish IPO
05:15 The Psychology of Founders
11:52 A Counter Story: Priceline's IPO
15:13 Reflecting on High School Memories
15:37 The Illusion of Endless Wealth
15:51 The Reality of Financial Downturns
19:09 Understanding Venture Capital Statistics
21:28 The Rarity of Repeat Success
24:18 Advice for Founders: Secure Your Wins
28:11 The Importance of Financial Safety
30:39 Final Thoughts: Keep the Win

Does LOCATION matter for your startup?

Startups.com — Mon, 24 Mar 2025 08:05:17 -0700

Ryan and Will discuss the evolution of startup location strategies. They reminisce about the bygone era when relocating to major hubs like San Francisco was essential for success due to access to talent, investors, and networking opportunities. Now, with advancements in remote work, AI, and digital connectivity, these factors have become less relevant. Ryan and Will delve into the changing dynamics of raising capital, building teams, and cultivating networks without needing to uproot one's life to a specific city.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:39 The Shift in Startup Location Importance

01:46 Reevaluating the Need to Move for Startups

01:58 The Impact of Remote Work and COVID-19

03:51 Debating the Necessity of Moving to San Francisco

06:12 Talent Acquisition in the Remote Work Era

09:23 Financial Considerations and Cost of Living

15:10 The Role of Investors in the New Startup Landscape

17:54 Questioning the Need for Large Engineering Teams

18:21 Capital Requirements and Investor Expectations

19:14 The Evolution of Pre-Seed Rounds

22:27 The Impact of Technology on Investment

23:43 Relocating for Networking Opportunities

27:13 The Shift in Startup Location Necessities

32:03 The Value of Flexibility in Startup Locations

35:59 Conclusion: Startups Can Thrive Anywhere

Are The Sacrifices Worth It?

Startups.com — Mon, 17 Mar 2025 07:55:03 -0700

In this episode of the Startup Therapy Podcast, the guys tackle the big question: was the entrepreneurial journey worth it? They discuss the sacrifices, the missed experiences, and the immense pressures that come with being a founder. Will shares a touching story about his daughter's unprompted appreciation for his hard work, leading to a reflection on whether the grinding was worth the outcome. Both hosts also highlight the freedom, flexibility, and the unique sense of achievement they've gained. However, they caution about the inevitable costs and the importance of balancing life and startup aspirations. A must-listen for anyone questioning the value of their entrepreneurial path.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:49 A Moment of Gratitude

02:42 Was It All Worth It?

06:02 Missed Experiences and College Life

11:00 The Weight of Responsibility

15:12 Habits and Hardships

19:32 Guilt and Work-Life Balance

24:20 The Timeless Nature of Startup Challenges

24:52 The Hidden Costs of Success

25:47 The Value of Sacrifice

26:39 The True Meaning of Freedom

28:04 The Journey to Personal Agency

29:20 The Impact of Entrepreneurship

31:15 The Irony of Wealth and Freedom

35:12 The Cost of Corporate Success

45:44 Balancing Life and Startup

Are Founders Forged Over Youth?

Startups.com — Tue, 11 Mar 2025 06:05:57 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss how childhood experiences influence the entrepreneurial journey. They explore why many founders' origin stories trace back to their early years and how formative events can plant the seeds of entrepreneurship. Will shares his personal story of selling candy as a child, highlighting moments that taught him vital business skills. The conversation also delves into the importance of agency, the tools needed for entrepreneurial success, and the role of parents in nurturing a child's potential to create their own path.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:13 Exploring Founder Origin Stories
01:51 Will's Childhood Story
10:14 The Power of Agency
10:53 Teaching Kids About Agency
20:54 Personal Reflections on Agency
21:22 The Power of Agency and Optimism
22:14 Parental Protection vs. Empowerment
22:40 Real-Life Stories of Overcoming Adversity
24:40 The Magic of Agency in Hardship
26:42 Tools for Founders and Kids
27:23 Early Lessons in Entrepreneurship
34:56 The Importance of Sales Skills
42:29 Teaching Kids the Value of Agency
43:22 Join the Startups.com Community

Assets OVER Exits

Startups.com — Mon, 03 Mar 2025 09:00:00 -0800

In this episode of Startup Therapy, Ryan Rutan and Will Schroeter challenge the startup world's focus on big exits and venture capital. They highlight the benefits of cash-flowing businesses, showing how consistent profits can lead to financial security. Using real examples, they explain how making $10K a month can be as powerful as having millions in the bank—emphasizing sustainable growth and long-term success.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:19 The Value of Consistent Cash Flow

01:23 Examples of Profitable Local Businesses

03:37 The Misconception of Startup Exits

03:49 Real-Life Stories of Successful Small Businesses

06:16 The Broken Narrative of Startup Wealth

07:26 Reevaluating Business Success Metrics

09:05 The True Value of a Profitable Business

09:38 Calculating the Financial Impact

13:20 The Reality of Business Exits

18:09 Replacement Value vs. Exit Value

19:14 The Value of Experience and Pre-existing Solutions

19:39 Cash vs. Business Value: A Deep Dive

20:21 Real-life Examples of Business Growth

23:34 Risks and Rewards of Running a Business

27:12 The Importance of Consistent Earnings

34:54 Long-term Value and Compounding Effects

You Only Have to Be Right Once

Startups.com — Mon, 24 Feb 2025 09:00:00 -0800

In this episode of the Startup Therapy podcast, Ryan and Will chat about how startup success isn’t always a straight path. They use Mark Cuban’s story as a prime example, showing why sticking it out for the long run is so important—because success can happen at any time in a founder’s career. They also talk about how those early small wins can build up to something bigger and why setting strict timelines for success doesn’t really make sense. At the end of the day, one big right moment in a 50-year career can be a total game-changer.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:07 The Reality of Founders' Success

02:00 Mark Cuban's Journey to Billionaire Status

06:35 The Importance of Small Wins

10:15 Financial Stability and Early Success

15:57 The Value of Consistent Small Wins

18:02 Success Doesn't Have a Timeline

18:12 When Does Success Happen?

18:20 Examples of Late Bloomers

18:45 The Myth of Early Success

19:59 The Impact of Timing

20:44 The Internet Era and Young Wealth

21:40 Outliers and Unrealistic Expectations

25:13 Consequences of Chasing Quick Success

27:28 The Value of Longevity in Business

30:02 Unexpected Success Stories

31:46 Staying in the Game

32:36 Join the Startups.com Community

What Would I do Differently

Startups.com — Mon, 03 Feb 2025 10:00:00 -0800

In this episode of The Startup Therapy, Ryan Rutan and Will Schroter explore the 'what if' scenarios that often preoccupy founders. Will shares personal milestones, showing how taking bigger risks shaped his journey. They discuss the hidden costs of success, the pitfalls of romanticizing alternative outcomes, and the importance of realistic risk assessment. The key takeaway? Embrace risk to avoid the regret of missed opportunities.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:07 – Reflecting on milestones and 'what ifs'
00:44 – The risks and rewards of entrepreneurship
04:00 – A hilarious temp job experience
07:34 – The reality of alternate paths
09:02 – The danger of romanticizing 'what ifs'
13:48 – The cost of success
15:29 – Building a realistic mental model
16:18 – Stop guessing and get real answers
16:26 – The cost of staying in a job you hate
17:30 – Should you stay or leave?
18:10 – The true cost of success
19:12 – The hindsight trap: romanticizing outcomes
21:56 – Learning from failure and modeling risk
22:55 – Zirtual acquisition: a case study in risk
28:47 – Surviving failure and moving forward
31:35 – Avoiding regret and embracing risk

When Can I Afford to GAMBLE?

Startups.com — Mon, 27 Jan 2025 09:00:00 -0800

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter dive into an interesting perspective: taking risks in entrepreneurship is actually a luxury, not the norm. They break down what it really costs to take risks, how to figure out your "minimum viable risk pool," and why having a financial cushion is key to surviving setbacks.

They share personal stories from their experience at Startups.com, emphasizing the importance of cutting personal and business expenses to stretch your runway and make smarter decisions. This episode is all about helping entrepreneurs understand the financial milestones they need to hit to keep their businesses afloat—and how time plays a big role in navigating risks.

This episode is packed with advice for anyone trying to manage the tricky balance of risk and reward in entrepreneurship. Tune in to learn how to take smarter risks and build a solid foundation for your business!

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:15 Why Taking Risks Is a Luxury

02:08 Balancing Personal and Business Costs

03:44 Lessons from Startups.com

05:55 Why You Need a Risk Buffer

10:25 Figuring Out the Minimum Viable Risk Pool

16:51 Financial Discipline and Budgeting

19:09 The Freedom Fund Explained

26:51 How to Survive Financial Challenges

Can Founders Find Contentment?

Startups.com — Tue, 21 Jan 2025 09:00:00 -0800

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeter delve into the anxiety surrounding contentment in the startup ecosystem. They question the conventional wisdom that equates contentment with stagnation and probes whether startup founders should aim for contentment as a goal. Through personal anecdotes and industry examples, they explore the influence of perpetual ambition and societal expectations on entrepreneurs. They also discuss the differences between being content and being complacent and reflect on the continuous urge to chase new problems and challenges, even when previous goals have been achieved.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:44 Questioning the Need for a Business Coach
02:05 The Dilemma of Contentment vs. Ambition
04:02 Reflecting on Milestones and Contentment
07:35 The Nature of the Startup World
15:23 Anxiety as a Driving Force
20:51 The Anxiety of High Achievers
22:11 The Pressure of Success: Avicii and Pharrell
23:59 Imposter Syndrome Among Overachievers
26:21 The Elusive Goal of Contentment
29:08 Balancing Ambition and Contentment
33:29 The Trap of Endless Ambition
40:44 Finding True Satisfaction

Why do Investors FIRE Founders?

Startups.com — Mon, 13 Jan 2025 22:00:00 -0800

Ryan Rutan and Will Schroeter discuss the complexities and challenges faced by startup founders, particularly the frequent occurrence of founders being replaced by investors. The conversation delves into the motivations behind such investor decisions, the difficulties in replicating a founder's passion and vision, and the common pitfalls and consequences of these transitions. The hosts share personal anecdotes and provide insights on how to prevent these situations, handle them professionally if they arise, and maintain valuable stakeholder relationships. This episode is a must-listen for any startup founder navigating the turbulent waters of investor relations and company growth.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:25 The Downfall of Bench and Ian Crosby's Story
01:54 Investor Motivations and Founder Replacements
03:33 Understanding Investor Expectations
05:40 The Slow Burn of Founder Dismissal
08:23 The Impact of Replacing Founders
13:49 Personal Stories of Founder Replacement
16:47 The Challenges of Replacing Founders
19:26 Augmenting the Team vs. Replacing the Founder
22:01 Why Investors Push Founders Out
24:00 Navigating Earn-Out Periods in Acquisitions
24:26 The Challenge of Replacing Founders
26:43 Timing the Transition: Leadership vs. Management
29:08 The Mercenary CEO: Pros and Cons
35:31 Investor Expectations and Founder Realities
42:19 Handling Founder Exits Professionally

The Burden of Unrealistic Expectations

Startups.com — Mon, 02 Dec 2024 09:00:00 -0800

In this episode Ryan and Will delve into the intense pressures faced by founders from investors, peers, and the startup community. They discuss how these external expectations often drive founders to pursue goals misaligned with their personal beliefs and values. The conversation explores how unchecked expectations can lead to burnout and misguided efforts. They share insights on the importance of auditing and resetting personal and business expectations to ensure they align with one's true goals and values. The hosts also highlight the dangers of comparing oneself to other founders or industry giants, and emphasize the significance of building a business that meets personal fulfillment rather than external benchmarks.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for:
00:32 The Source of Pressure and Expectations
03:32 Investor Expectations and Their Impact
04:05 Personal Story: Missing Investor Expectations
05:44 The Reality of Investor Expectations
10:15 Comparing Yourself to Other Founders
17:45 The Peer Comparison Trap
18:06 Personal Journey: From Poverty to Success
20:01 The Futility of Social Media Comparisons
23:07 Tying Success to Self-Worth
28:20 The Illusion of Goals and Success
31:53 Reevaluating Startup Expectations
36:43 Conclusion: Building What Matters to You

How do I Stay Positive In Tough Times?

Startups.com — Mon, 25 Nov 2024 09:00:00 -0800

Ryan and Will discuss the omnipresent challenges that come with running a startup. They delve into the perpetual 'shit storm' that founders face and share practical advice on how to keep moving forward even when everything feels like it's falling apart. Key points include regaining perspective, converting anxiety into actionable tasks, breaking down large goals into manageable micro-goals, and finding healthy obsessions to channel stress. They emphasize the importance of maintaining a positive outlook, not just for personal sanity but for the wellbeing of the entire team, and share personal anecdotes and strategies that have helped them through their toughest times.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for:
00:07 The Perpetual Shit Storm of Startups
01:01 Practical Advice for Founders in Crisis
02:10 Regaining Perspective During Tough Times
05:08 Personal Stories of Overcoming Challenges
15:29 The Importance of Taking Action
20:41 Managing Anxiety with Side Tasks
21:58 The Power of Micro Goals
23:37 Breaking Down Big Tasks
26:29 The Importance of Focus
32:07 Finding Healthy Obsessions
41:08 Building Momentum with Small Wins
43:14 Join the Startups.com Community

Are Investors Trying to Push Us a Cliff?

Startups.com — Mon, 18 Nov 2024 09:00:00 -0800

In this episode of the Startup Therapy Podcast, Ryan and Will delve into the often misunderstood motivations of venture capitalists. They discuss why investors push startups to grow rapidly, the pressures VCs face to deliver returns within a specific timeframe, and the fundamental differences between the stakes for founders and investors. The episode uncovers the reasons behind the 'push you off a cliff' approach, the impact of the 2 and 20 model on VC behavior, and the importance of understanding these dynamics to better navigate the startup journey.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for:
00:11 Understanding Investor Motivations
01:12 The VC Time Crunch
03:57 Profit vs. Growth: A VC Perspective
13:25 The Reality of VC Salaries
16:29 Founders vs. Investors: Different Stakes
19:00 Conclusion: Aligning Goals with Investors

What Previously Funded Founders Do Differently

Startups.com — Mon, 11 Nov 2024 09:00:00 -0800

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the daunting realities of raising capital for startups. By sharing insights and experiences from both first-time and repeat founders, they delve into the recurring theme of regret found amongst entrepreneurs who've gone through the funding process. Topics include the hidden costs of raising money, the pitfalls of losing focus, and the challenges of working with investors. The hosts offer practical advice on when to raise funds, how to mitigate the risks of distraction, and the importance of being selective and strategic about bringing investors on board. Whether you're gearing up for your first round of fundraising or re-evaluating your approach, this episode provides valuable lessons to help navigate the complex landscape of startup financing.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for:
00:14 The Reality of Raising Funds
00:38 Founders' Regrets and Reflections
02:15 The Perils of Not Getting Paid
04:22 Understanding Founder Compensation
11:04 Strategies for Better Compensation
13:24 Challenges with Profitable Companies
15:02 The Pressure to Grow or Bust
15:16 The Dilemma of Raising Too Early
15:47 The Vulnerability of Early Stages
16:22 The Importance of Timing in Fundraising
16:56 The Pitfalls of Early Funding
17:28 The Distraction of Fundraising
20:34 The Impact of Investor Expectations
28:23 The Challenge of Having a New Boss
31:50 Key Takeaways and Final Thoughts

Are Startups Easier for Experienced Founders?

Startups.com — Mon, 04 Nov 2024 09:00:00 -0800

In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurship, sharing personal anecdotes and insights from their extensive history of building and acquiring startups. Discussing expectation management, the double-edged sword of experience, and the harsh realities of repeating past mistakes, Ryan and Will emphasize that while experience offers certain advantages, it does not guarantee success in new ventures. They also highlight the emotional resilience required to endure the cyclical nature of startup challenges and the ever-present difficulties of achieving product-market fit and successful marketing, regardless of prior victories.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for:
00:15 Debunking the Myth of Easier Startups
01:27 The Double-Edged Sword of Experience
02:32 Drawing from Multiple Experience Buckets
05:15 Expectation Management in Startups
09:39 Avoiding Duplicate Mistakes
13:01 Raising Capital: Lessons Learned
15:16 The Value of Experience in Decision Making
17:07 The Reality of Investor Promises
17:17 Understanding People: A Founder's Key Skill
18:38 Emotional Maturity in Leadership
20:00 Challenges That Never Get Easier
21:57 The Ever-Changing Landscape of Product Market Fit
25:39 Marketing Struggles for Experienced Founders
27:40 The Pain of Failure: It Never Gets Easier
31:30 The Value of Experience and the Role of Luck
32:38 Join the Startups.com Community

Who's Working for Who?

Startups.com — Mon, 28 Oct 2024 08:00:00 -0700

Ryan Rutan and Will Schroter explore the intricate and often misunderstood relationship between founders and their startups. They tackle the question of whether the founder works for the startup or vice versa, challenging common perceptions shaped by societal views and political discourse. The hosts discuss the unspoken 'contract' entrepreneurs form with themselves, the inevitable trade-offs of startup leadership, and the sacrifices founders make for their companies. They emphasize the emotional and financial tolls on founders, the discrepancies in founder-employee dynamics, and the need for startups to stay aligned with the founder's original mission. This episode stresses the importance of maintaining control and balancing personal goals with the demands of the startup ecosystem.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for
00:35 The Founder vs. Startup Dilemma
00:51 Political and Economic Perspectives
01:40 The Reality of Founders' Lives
03:00 The Initial Contract of Founders
05:11 The Shift in Founders' Roles
06:15 The Permanent Struggle of Founders
07:43 Revisiting the Founders' Goals
10:34 The Reality Check
15:30 The Investor's Impact
15:44 The New Boss: Investors and Liabilities
16:49 The Pain of Payroll: Sacrificing Founder Salaries
19:10 Credit Cards and Cash Flow: Desperate Measures
21:20 The Founder’s Dilemma: Sacrifice and Equity
23:42 The Reality of Startup Success: Rare and Elusive
28:28 The Emotional Toll: Identity and Relationships
31:49 Conclusion: Building a Startup That Works for You

Let's Get Back to Our WHY

Startups.com — Mon, 21 Oct 2024 09:00:00 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter explore the vital importance of maintaining a startup's foundational 'why' – the core reason for its existence. They discuss the excitement and clarity that founders experience in the early stages, the operational challenges that can cause them to lose sight of their mission over time, and practical strategies for rekindling that original passion. Through personal anecdotes and examples of companies like Apple and Google, the hosts underscore how minor compromises can erode a company's core mission. They emphasize the need for founders to continuously revisit and reinforce their original motivations to ensure sustained passion and purpose. Listeners will gain insights on recognizing when they've deviated from their vision, the benefits of realigning with the 'why', and actionable steps to recenter their focus, all while maintaining clarity and engagement within their teams.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn

/ startups-co

Join our Network of Top Founders
Wil Schroter

/ wilschroter
Ryan Rutan

/ ryan-rutan

What to listen for
00:29 The Importance of 'Why' in Startups
03:17 Losing Sight of the 'Why'
05:24 Diagnosing the Loss of 'Why'
09:21 The Impact of Compromises
15:56 Tiny Compromises Lead to Major Changes
18:48 The Slippery Slope of Compromises
19:50 Losing Sight of the 'Why'
20:50 Rediscovering the Purpose
22:12 The Importance of Remembering the 'Why'
24:30 Practical Steps to Reconnect with the 'Why'
30:55 Identifying and Correcting Misalignments
35:36 The Constant Battle to Maintain the 'Why'

How We Secretly Lose Control of Our Startups

Startups.com — Mon, 07 Oct 2024 07:01:34 -0700

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the complex dynamics of maintaining control in a startup. They explore the misconception that not having investors means maintaining control and highlight the various ways founders inadvertently lose control—from customers, co-founders to their own staff. They delve into the idea that control is a currency spent for growth and emphasize the importance of understanding and strategically managing the areas founders are willing or unwilling to cede control over. They reveal how seemingly routine decisions can lead to significant shifts in control, urging startup founders to be proactive in understanding and negotiating these exchanges.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
/ startups-co

Join our Network of Top Founders
Wil Schroter
/ wilschroter
Ryan Rutan

Should Kids Follow in our Founder Footsteps?

Startups.com — Mon, 16 Sep 2024 09:00:00 -0700

In this episode of the Startup Therapy Podcast, Ryan and Will explore the complexities of encouraging their children to become entrepreneurs. With nearly 300 episodes discussing the founder's journey, they delve into whether they'd want their kids to follow the same path. They recount personal experiences, weigh the pros and cons, and discuss the importance of allowing their children to make their own decisions. The episode emphasizes providing the tools and support to foster independent choices rather than directing them towards entrepreneurship.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for
00:00 Introduction: The Founder’s Dilemma
00:55 A Proud Yet Conflicted Parent
02:27 The Value of Experience
05:03 Balancing Passion and Practicality
08:10 Nurture vs. Nature in Entrepreneurship
09:59 The Role of Education and Constraints
16:21 The Reality of Entrepreneurship
18:56 Reflecting on Founders' Struggles
19:39 Balancing Optimism and Realism in Entrepreneurship
19:59 The Timeless Nature of Startup Challenges
21:31 Empathy and the Reality of Startup Therapy
23:10 The Impact of Parental Influence on Career Choices
25:23 Encouraging Authenticity in Children's Career Paths
30:12 Empowering Kids to Make Their Own Decisions
35:07 Final Thoughts on Raising Future Founders

The Evolution of Entry Level Workers

Startups.com — Tue, 10 Sep 2024 05:03:50 -0700

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter discuss the evolving landscape of entry-level hiring for startups. They dive into why U.S. college graduates have fallen to the fourth pick for entry-level positions, overtaken by AI, global talent, and experienced young professionals who leverage new tools and platforms to gain relevant skills. They explore the benefits of each hiring option, debunk common misconceptions about global talent, and outline how these changes empower startups to make smarter, more economical hiring decisions. The discussion offers valuable insights for startup founders navigating the challenges of building efficient teams under tight budgets.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for
00:00 Introduction: The Changing Landscape of Entry-Level Talent
01:26 The Rise of AI in Startups
03:48 Global Talent: A New Frontier
07:30 Young and Hungry: The New Entry-Level
10:19 Challenges and Opportunities for College Grads
15:57 Resource Allocation in Startups
24:06 Stop Guessing and Get the Answers
24:16 The Global Talent Pool Advantage
25:15 Quality Concerns and Misconceptions
27:21 Parallel Validation in Startups
32:51 The Rise of Young and Hungry Talent
35:51 Evolving Job Market Expectations
39:50 The Changing Landscape of Hiring
45:20 Conclusion: Embrace the New Opportunities

Assume Everyone Will Leave in Year One

Startups.com — Mon, 02 Sep 2024 09:00:00 -0700

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges of managing early-stage startup teams, particularly the high likelihood of turnover and the risks of handing out equity prematurely. They talk about the emotional toll of losing key team members and offer practical advice on creating vesting schedules and setting realistic expectations to safeguard against these common pitfalls. The conversation also touches on the dynamics of initial hires, the importance of flexibility, and the need to balance passion with practical considerations in team building.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for
00:00 Introduction to Startup Challenges
00:09 The Reality of Early Startup Teams
01:25 Startup Weekend Insights
02:38 The First Love Analogy
03:44 The Commitment Dilemma
04:24 Life Happens: Unplanned Disruptions
12:02 The Fragility of Equity-Based Compensation
13:45 Long-Term Team Dynamics
15:32 Understanding the Nature of Turnover
17:44 The Emotional Impact of Employee Departure
18:52 The Reality of Passion and Commitment
27:20 Equity Distribution and Vesting Schedules
31:50 Preparing for Inevitable Change

Was Mortgaging My Life Worth it?

Startups.com — Mon, 26 Aug 2024 09:00:00 -0700

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter delve into the sacrifices that come with building startup companies. They explore the dangerous ambiguity of not having specific goals and timelines, using personal anecdotes to illustrate the costly trade-offs. Will reflects on his milestone birthday and the realization that 'later' never seems to arrive, sparking a discussion about the true worth of deferred happiness and success. The conversation underscores the importance of quantifying goals and ensuring that sacrifices made today lead to genuinely rewarding outcomes. They emphasize that the journey must be carefully balanced with immediate gratification to avoid a future riddled with regret. Through vivid storytelling, they highlight the crucial lessons for founders on how to navigate the complex landscape of ambition, sacrifice, and personal fulfillment.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for

00:21 The Danger of Vague Goals

00:57 Personal Reflections on Sacrifice

02:16 Quantifying Sacrifices and Rewards

04:03 The Reality of Sacrifice

05:27 Anecdotes of Sacrifice

15:08 The Moment of Truth

18:04 The Grand Experiment in Beverly Hills

18:36 The Struggles of Finding a Home in LA

19:07 Realizing the Cost of Living in Bel Air

20:34 Questioning the Move: A Moment of Clarity

23:10 The Decision to Return to Columbus

23:21 Reflecting on Sacrifices and Rewards

25:42 The Founder's Paradox: Happiness vs. Sacrifice

28:31 The Reality of Achieving Success

35:27 Balancing Sacrifice and Returns

What's my Startup Worth in an Acquisition?

Startups.com — Mon, 19 Aug 2024 09:00:00 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Startups.com founder Will Schroter discuss the unrealistic expectations that many startup founders have when it comes to selling their business. They detail the common pitfalls and misconceptions about startup valuation, the differences between raising capital and selling, the realities of private equity, and the dangers of deferred compensation. With insights from their own experiences of buying and selling companies, Ryan and Will provide a candid look at how to navigate the tricky world of startup acquisitions and set more realistic expectations for exit strategies.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for
00:00 Introduction to Startup Acquisitions

00:16 Realistic Expectations in Business Sales

01:09 Understanding the Acquisition Process

01:37 Our Acquisition Experience

02:29 Challenges in Closing Deals

04:31 The Importance of Direct Communication

07:08 The White Knight Fallacy

13:07 Investor Expectations vs. Reality

20:35 The Figma Acquisition: A Case Study

21:12 Understanding Market Leadership and Valuation

21:44 The Reality of Acquisition Multiples

24:53 The Spectrum of Potential Buyers

26:07 Private Equity: The Predatory Buyer

28:32 The Harsh Truths of Selling a Startup

32:53 Cash vs. Deferred Compensation

39:15 Managing Expectations in Startup Exits

Is my AMBITION my ENEMY?

Startups.com — Mon, 12 Aug 2024 17:25:56 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss the often overlooked costs of ambition in the startup world. They explore how ambition, while necessary for building innovative companies, can become a debilitating force, leading to severe health issues, strained relationships, and emotional burnout. Using personal anecdotes and analogies, they emphasize the importance of recognizing the tipping point where ambition becomes more detrimental than beneficial, and advocate for a balanced approach to sustain long-term personal and professional health.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for
00:00 Introduction to Ambition in the Startup World
00:30 The Double-Edged Sword of Ambition
01:27 The Escalating Costs of Ambition
02:18 Ambition's Impact on Founders' Lives
05:22 Personal Stories of Ambition and Sacrifice
12:52 The Cultural Reward of Sacrifice
16:16 Understanding Technical Debt and Burnout
16:58 The Hidden Costs of Ambition
17:06 Financial Struggles and Early Warning Signs
18:20 Impact on Relationships
20:40 Mental Well-being and Isolation
23:55 The Ultimate Price: Physical Health
27:12 A Rational Perspective on Work-Life Balance
28:46 Final Thoughts and Advice

Are Startups in a "Silent Recession"?

Startups.com — Mon, 05 Aug 2024 09:00:00 -0700

In this episode we discuss the current state of the startup ecosystem, which they describe as a 'silent recession.' Despite economic indicators suggesting otherwise, many startup founders are struggling with reduced capital flow and stagnating customer acquisition. The episode delves into the effects of the economic downturn on startups, the impact of investor behavior, and the historical context leading up to the current situation. Ryan and Will emphasize the importance of resetting expectations, adopting a survival mindset, and making tough decisions to ensure longevity in this challenging environment. While this period is difficult, there is always light at the end of the tunnel for those who can weather the storm.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:08 The Silent Recession in Startup Land
00:38 The Reality of Founders' Struggles
02:25 Economic Indicators vs. Founders' Experiences
04:39 The COVID-19 Economic Magic Trick
06:03 The Shift in Startup Funding Dynamics
11:15 The Onset of Economic Challenges
12:20 The Impact on Startup Operations
16:14 VCs Halt Investments
16:50 Impact on Startups
17:35 IPO Implosions
18:20 VCs' Strategic Pause
19:56 The Domino Effect
22:56 Navigating the Downturn
27:39 Survival Strategies
31:37 Looking Ahead
33:07 Join the Startups.com Community

Do Founders Deserve Their Profit?

Startups.com — Mon, 29 Jul 2024 08:00:00 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeder navigate the complexities founders face regarding success and societal scrutiny. They delve into the common critiques founders encounter about their profits and perceived entitlement while emphasizing that success should be celebrated not vilified. The conversation provides a detailed look at the multiple layers of taxation startups endure and the misconceptions surrounding founder wealth. They also highlight the emotional toll and risk involved in building a startup, offering insights into the importance of supporting founders and normalizing success.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:00 Introduction to the Startup Therapy Podcast
00:46 The Stigma of Founders' Success
04:47 The Burden of Taxes on Founders
13:55 The Lack of Support During Failure
16:06 Reflecting on College Days and Financial Struggles
16:25 The Reality of Startup Life
17:25 Deserving Success and the Guilt Complex
18:50 Comparing Founders to Other Professions
21:36 The Value of Innovation and Hard Work
25:36 Addressing Income Inequality and Fairness
28:42 Encouraging Charitable Giving and Community Support
30:12 Join the Startups.com Community

The Utter STUPIDITY of "Risking it All"

Startups.com — Mon, 22 Jul 2024 08:00:00 -0700

In this episode we discuss the myth of the 'bet it all' startup mentality. They highlight the importance of downside risk planning and how successful risk management plays a crucial role in startup success

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:00 Introduction to Startup Therapy
00:28 The Myth of Betting It All
01:36 The Reality of Downside Protection
06:18 Case Study: The Zirtual Acquisition
11:24 The Importance of Backup Plans
18:58 Conclusion and Final Thoughts

Why Most Founders Don't Get Rich

Startups.com — Mon, 15 Jul 2024 08:00:00 -0700

In this episode of the Startup Therapy Podcast, we discuss the common struggles of making money in the startup world. They explore the 'noble' but flawed narrative that founders shouldn't pay themselves, why aiming too big too soon can prevent profitability, and the cycle of raising funding that often leaves founders broke.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 Introduction to Startup Therapy

00:23 The Broken Narrative of Not Getting Paid

02:35 Self-Sabotage and Going Too Big

04:08 The Funding Trap

05:41 The Harsh Realities of Raising Money

12:07 The Never-Ending Hunger of Startups

14:36 Reinvesting in Growth

15:06 The Reality of Increased Liabilities

15:59 The Fear of Taking Money Off the Table

17:00 The Importance of Paying Yourself

18:14 Balancing Profit Sharing and Salaries

19:07 The Misconception of Startup Growth

21:13 The Dangers of Not Taking Money Off the Table

26:09 Common Sense in Startup Land

27:08 Conclusion: Get Paid Now

Investors will be Obsolete, The End of Venture Capital

Startups.com — Mon, 08 Jul 2024 09:00:24 -0700

In this episode, we discuss the potential obsolescence of venture capital due to advancements in AI technology. We explore how reduced startup costs and increased efficiency might reshape the future of funding in the startup ecosystem.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 Image a World Without Investors
02:16 The Rise of AI and Its Impact
03:01 Cost Reduction in Startups
06:05 The Future of Staffing and Marketing
08:37 Automation in Back Office Operations
13:04 The Changing Role of Investors
24:21 The Reality of VC Advice
27:57 The Future of Capital Needs
31:22 AI's Impact on Investment
34:40 Reimagining Investment Models
40:20 The Democratization of Startups

Why is a Founder so HARD to replace?

Startups.com — Mon, 01 Jul 2024 07:44:18 -0700

The Irreplaceable Founder. Ryan Rutan and Will Schroter discuss the irreplaceable role of founders in startups. They explore why removing a founder often leads to failure, the unique value and vision founders bring, and the difference between operational tasks and the founder's core contributions.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 Founder’s Role in a Startup
01:16 Challenges of Replacing a Founder
03:04 Founder’s Vision
05:43 Founder’s Passion
07:02 Founder’s Decisions
09:17 The Unique Value of Founders
20:06 Sales Process and Financials
22:49 Management by Walking Around
25:28 Risk Tolerance in Founders vs. Hired CEOs
33:07 Challenges of Replacing a Founder
37:54 Join the Startups.com Community

We Can't Grow by Saying "No"

Startups.com — Mon, 24 Jun 2024 10:41:10 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan (CMO at Startups.com) and Wil Schroter (CEO at Startups.com) discuss the importance of saying yes to growth opportunities that startups have not previously tried. They emphasize that startups thrive by committing to new challenges, even if the path isn't immediately clear, and how this willingness to stretch can affect interactions with customers, investors, and staff.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

This is WHY More Money Means MORE Problems

Startups.com — Mon, 17 Jun 2024 13:34:09 -0700

Why sometimes, less is more? Ryan Rutan and Will Schroeder discuss the misconception that reaching revenue milestones in startups will solve all problems. Explore how each milestone brings new challenges, why growing liabilities can be riskier than anticipated and the importance of balancing growth with stability.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 The Illusion of Milestones
02:46 Scaling Challenges
05:33 Weight of Responsibilities
13:37 New Nodes of Problems
16:21 The Reality of Scaling a Team
20:05 The Myth of Effortless Wealth
22:59 The Importance of Sustainable Growth
26:20 The Pitfalls of Chasing High Valuations
28:22 Setting Realistic Business Goals
30:24 How to Enjoy Your Business

Committees are Where Progress Goes to Die

Startups.com — Mon, 10 Jun 2024 08:50:42 -0700

In this episode of the Startup Therapy Podcast, we discuss the inefficiencies and dangers of making decisions by committee. Why committees often fail and why founders should avoid relying on them for critical decisions. Tune in to learn why decisive, individual leadership is key to startup success.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 Intro
01:34 The reality of committee decision-making
07:06 The problem with collective accountability
11:38 The downside of inclusive decision-making
15:38 The myth of the best decision
17:46 The importance of accountability
23:04 The danger of removing consequences
28:27 Leadership is about making the tough decisions

Giving Up Equity? Press Pause First

Startups.com — Mon, 03 Jun 2024 09:53:17 -0700

In this episode of the Startup Therapy Podcast, we talk about equity distribution in startups. Explore the psychological traps of seeking validation, the dangers of making hasty decisions when most vulnerable, and offer practical advice on how to navigate these challenges. Tune in to learn why patience and cautious decision-making are key to safeguarding the future value of your company.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 Intro

01:00 The Vulnerability of Early-Stage Founders

06:45 Evaluating Potential Co-Founders

07:55 The Risk of Overpaying for Talent

13:38 Milestones and Deliverables

17:00 Vulnerability in Decision Making

18:27 The True Cost of Equity

24:09 The Fallacy of Immediate Gratification

28:34 Why Wait and Evaluate

Why Do 99% of Founders Suck at Asking for Help?

Startups.com — Mon, 27 May 2024 08:43:31 -0700

In this insightful episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter discuss the importance of asking questions as a startup founder.Why founders often hesitate to seek advice, the untapped wealth of knowledge available?

You will find tips on how to develop the muscle for asking the right questions — founders do not need to reinvent the wheel.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

The Value of Actually Getting Paid (Avoid This Big Danger)

Startups.com — Mon, 20 May 2024 11:35:25 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter, discuss the misconception that startup founders are incredibly wealthy on paper, while in reality, many struggle with personal financial stability. See the importance of paying yourself regularly, even when building a high-potential startup. Consistently getting paid, no matter how small, is crucial to long-term success and personal well-being.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

Will Investors Bail Me Out? Brutal Truth About Startup Investments

Startups.com — Mon, 13 May 2024 12:18:13 -0700

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter talk about sacrifices founders make — accumulating debt and foregone salaries, with the expectation of being reimbursed. They discuss how founders commonly believe that future investments will pay back their personal financial commitments. They emphasize that the only real chances of getting 'paid back' are through a company sale or profit distributions. They put a light on the tough lessons learned through their own experiences and those of others in the startup world.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

Is the problem the Player or the Coach? Team Building Hacks

Startups.com — Mon, 06 May 2024 11:47:06 -0700

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter delve into evaluating startup team and management performance. Find out the importance of constant evaluation, highlighting the significance of both recognizing the need for improvement and taking actionable steps towards building a higher quality team.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

Do people really want me to succeed? Founders vs World

Startups.com — Mon, 29 Apr 2024 08:25:10 -0700

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter explore the harsh reality of seeking support as a founder. Surprising, limited number of people who genuinely want to see a founder succeed. You will hear about receiving superficial praise, the impact of social media on perception, and the psychological reasons behind others' reactions to success — the envy even among those closest to the founder.

Don't walk this narrow road alone, get support from your peers in founder groups at: https://www.startups.com/begin

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

You only THINK you work HARD — The Hard Work Illusion

startups.com — Mon, 22 Apr 2024 13:27:14 -0700

In this episode of the Startup Therapy podcast, hosts Ryan Rutan and Wil Schroter talk about the common misconception around 'working hard' within startups. They question the measurement of hard work, arguing that effort does not necessarily equate to progress or beneficial outcomes. The need for clear benchmarks within organizations to truly reward and recognize valuable contributions.

Additionally, they challenge the notion of what constitutes as 'hard work' and the danger of equating all effort with success, proposing a more nuanced understanding that could lead to more effective and rewarding startup cultures.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:17 The Misconception of Hard Work in Startup Culture
02:49 Real Value of Hard Work in Startups
04:29 The Effort vs. Progress Dilemma
06:40 Effort, Progress, and Reward
10:22 Learning from Effort and Reward
15:46 The Misconception of Effort vs. Outcome
17:36 Setting Expectations Across Management Levels
19:30 The Importance of Measurable Outcomes
28:31 Setting the Right Expectations and Rewards

SMALL is the New Big - Embracing Efficiency in the Age of AI

Startups.com — Mon, 15 Apr 2024 12:18:19 -0700

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter discuss the evolution of startups from the emphasis on scaling and headcount to prioritizing efficiency and output, largely due to advancements in AI. The challenges of the past, such as massive payrolls, investor dependency, and expensive infrastructures highlighting the opportunities AI technologies present for startups.

The conversation covers the changing landscape where small operations can achieve significant impact without the traditional costs, through examples like remote work, AI-driven efficiencies, and low-cost internet companies. They advocate for a shift in mindset where success isn't measured by headcount or office size, but by the value created with minimal resources.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to Listen For
00:00 The Evolution of Startups: From Headcount to Efficiency
01:29 AI and the Future of Work: A New Paradigm
05:14 The Unprecedented Scale and Speed of AI Adoption
07:14 AI's Impact on Staffing and Efficiency
09:39 The Ethical Debate: AI and Job Creation vs. Job Displacement
13:17 AI's Role in Democratizing Entrepreneurship
16:00 Historical Shifts in Startup Dynamics: From Match.com to AI
18:41 The Evolution of Startup Funding
19:33 The Dramatic Shift in Startup Economics
20:42 The Rise of Bootstrapping and Ownership Retention
21:24 Case Study: Plenty of Fish's Revolutionary Approach
24:32 The Future of Startup Costs and Ownership
31:55 Embracing Efficiency and Impact in Startups
33:48 A New Era of Startup Valuation and Efficiency

This is BOOTSTRAPPED - 3 Strategies to Build Your Startup Without Funding

Startup Therapy — Mon, 18 Mar 2024 08:59:25 -0700

In this episode of the startup therapy podcast, Ryan Rutan and Wil Schroter delve into bootstrapping a startup. They address common misconceptions about funding, emphasizing the importance of making do with what you have and prioritizing what's truly necessary for business growth. The conversation covers practical ways to manage expenses without external funding, including strategies for hiring, marketing, and managing operational costs through discipline and creative solutions.

The hosts share personal experience on how to navigate the challenges of bootstrapping, highlighting the importance of being resourceful, making money to spend money, and avoiding typical startup traps.

https://www.startups.com/newsletter

Resources:

Startup Therapy Podcast
https://groups.startups.com/
Join our Network of Top Founders
Check in with us on LinkedIn | Wil Schroter | Ryan Rutan

00:00 Welcome to Startup Therapy

00:08 The Realities of Bootstrapping

01:35 Navigating the Bootstrapping Journey

04:50 Mastering the Art of Compensation in Bootstrapping

22:00 Innovative Marketing on a Shoestring Budget

26:50 Leveraging Vendor Terms and Historical Examples

28:18 The Power of Deferred Payments in Business Growth

33:20 Strategic Use of Credit Cards for Business Expenses

42:20 The Path to Efficient Startup Growth

The Spectrum of Investor Advice

Startup Therapy — Mon, 11 Mar 2024 05:29:32 -0700

In this episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter discuss the complexities of handling feedback from investors, emphasizing the critical need for founders to properly qualify and assess the advice they receive. They highlight the dangers of acting on feedback without considering its relevance, potential bias, and the investor's qualifications. The discussion covers the spectrum of investor types, from well-meaning but inexperienced individuals to top-tier venture capitalists, and the importance of understanding the context and motivation behind their advice.

You will find how to advocate for a balanced approach that involves questioning, verifying, and thoughtfully considering advice before taking action.

https://www.startups.com/newsletter

Resources:

Startup Therapy Podcast
https://groups.startups.com/
Join our Network of Top Founders
Check in with us on LinkedIn | Wil Schroter | Ryan Rutan

$10K Per Month isn't Just Revenue. It's Life Support

Startups.com — Mon, 04 Mar 2024 02:00:00 -0800

In today's Startup Therapy Podcast, Wil and Ryan talks about why earning atleast $10,000 per month is one of the most important milestones in your startup career. They stress the need to do whatever it takes to keep your business alive. Hitting this milestone gives you room to handle setbacks and shows that you're making real progress. Tune in for tips on managing startup finances and staying resilient in the ever-changing business world.

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