But what if wealth quietly destroys your drive, energy, and sense of aliveness?

In this private webinar, Anastasia Koroleva, founder of Exit Paradox, reveals a powerful and deeply counterintuitive pattern she has observed in founders and CEOs after major exits — a state she calls post-wealth apathy.

After wealth, we optimise our lives for time and energy. We remove discomfort. We avoid stress. We follow what “feels good.”

Yet 10–20 years later, many high achievers find themselves living lives that are comfortable - but flat.
Low drive. Low energy. Low pull toward anything extraordinary.

In this webinar, Anastasia explains why the dominant post-wealth philosophy fails — and introduces the Worthy Challenge Framework, a science-grounded approach used by true post-wealth sages to stay peaceful yet energized, calm yet fully alive, without burning out.

This conversation is essential viewing for founders, CEOs, investors, and high performers navigating identity, purpose, and motivation after success.

In this episode, you’ll discover:
◼️ Why optimising for comfort after wealth leads to low dopamine and chronic apathy
◼️ The hidden biochemical reason drive disappears post-exit
◼️ Why “following your energy” often keeps you stuck and disengaged
◼️ The difference between time & energy optimisation vs worthy challenge living
◼️ How post-wealth sages stay deeply fulfilled without sacrificing peace
◼️ The framework that reignites sustainable motivation after financial freedom
◼️ Why most founders wait too long — and then never re-engage fully with life

If this conversation resonates, please share it with someone navigating life after an exit.

These ideas can quietly change the trajectory of an entire life.

Omar is a multi-exit entrepreneur and investor who has spent years studying the psychological and emotional realities of life after selling a business.

He reflects on the philosophy of life after success: how wealth gives safety but not security, why progress is really about trading old questions for better ones, and how many exited founders quietly waste their freedom by staying comfortable.

We explore:
• The moral responsibility that comes with capability
• Why regret is a better compass than ambition
• How founders get stuck using old success models in a new life
• Why contribution, not accumulation, becomes the real measure

Instead, she encountered something no one talks about—the Wealth Lag.

In this deeply honest and research-backed breakdown, Anastasia reveals the emotional crash that happens after financial freedom: the confusion, cognitive dissonance, identity loss, and the quiet dissatisfaction that haunts even the most successful founders, investors, athletes, and creators.

For 15 years she's studied hundreds of post-exit lives, and today he shares the patterns, tools, and stages that determine whether wealth becomes leverage for a deeply fulfilling life… or a trap that slowly suffocates us.

This episode is for anyone who has created wealth, is on the path to it, or wants to understand the psychological reality behind “success”.

Anastasia explains:

◼️ What the Wealth Lag really is — and why it hits every rich founder
◼️ Why the brain rebels against sudden wealth (cognitive dissonance explained)
◼️ How comfort becomes a silent addiction that drains purpose and identity
◼️ The 5 stages people must move through to adapt to wealth
◼️ Why most wealthy people stay stuck for decades
◼️ The emotional, intellectual, and spiritual work required after an exit
◼️ How to build a tribe that accelerates growth instead of stagnation
◼️ Why financial freedom does NOT create fulfillment — and what does

This is the real conversation that elite founders, ex-CEOs, wealth creators, and next-gen inheritors have behind closed doors. Exit Paradox brings it into the light.

If this episode helped you, please share it with someone who needs it.

TIMESTAMPS
00:00 – What Happens After Financial Freedom
00:22 – The Hidden Problem No One Warns You About
01:01 – The Wealth Honeymoon: Cars, Jets & New Toys
01:43 – Why Wealth Eventually Stops Feeling Good
02:15 – “Wealth Has Arrived… But I Haven’t”
02:58 – The Wealth Lag: Why Your Inner World Falls Behind
03:38 – Cognitive Dissonance: Your Brain’s Wealth Alarm System
05:00 – Why Most People Never Adapt to Wealth
06:39 – The Trap of Comfort (and How It Quietly Destroys Ambition)
07:28 – Step 1: Reframing Wealth as Leverage, Not the Goal
08:24 – Step 2: Building a Fulfilling Life Strategy Post-Exit
09:50 – Step 3: The Skills You Need After You Get Rich
10:42 – Step 4: Building a Tribe That Pulls You Forward
12:16 – Step 5: The Decision That Changes Everything
13:24 – The Real Mission: Clarity, Conviction & A Life Worth Living

Daniel Kivatinos journey is different and just as important to hear. His pause after selling his company didn't push him into a new path. It gave him clarity that he was already on the right one.

Daniel built and sold DrChrono, one of the first mobile medical platforms processing billions in medical billing. His work even took him to the White House to help shape healthcare data policy.

Today, Daniel is building JustPaid, an AI powered platform changing how businesses manage accounts receivable. 

In our conversation, Daniel shows us how he built that conviction about who he is and what he truly wants to do. In his case, to keep building highly impactful tech companies right in the heart of Silicon Valley.

TIME STAMPS:
00:00 – Fulfilment: “Some days I’m a five, some days a six”
00:19 – What would it take to feel like a 10?
00:58 – The illusion of a “perfect place” in life
01:17 – Mountain after mountain: why satisfaction always moves
01:37 – Introducing Daniel Kivatinos & his journey from DrChrono to JustPaid
02:14 – Can a life ever feel fully “satisfied”?
03:11 – Starting the conversation: Daniel joins the show
03:17 – How he discovered the podcast & why it resonated
03:36 – He sold DrChrono… and then started a new company within a year
04:05 – Why founders can’t take long breaks without losing their edge
05:40 – Did one year off give enough space for clarity? (Short answer: no.)
06:21 – Why entrepreneurs struggle with taking real time off
07:57 – The addictive nature of building companies
08:40 – Is the second company easier? (Spoiler: no, just “different hard.”)
10:10 – Is it ever easier the second time? Unrealistic expectations
10:43 – “You can’t hire people to build it for you”
11:40 – Even Steve Jobs struggled with his second company
13:07 – Why second-time founders often fail
14:33 – What Next actually gave Steve Jobs later
15:19 – Connecting the dots only works backward
15:44 – What Daniel did during his year off
16:40 – The Reddit founder told him to move to California
17:22 – Early Y Combinator days & why he never returned to NYC
17:39 – Considering moving away after the exit
18:01 – Missing family and exploring other states
23:15 – “What should I do with a year off?” His advice
23:59 – Driving across the U.S. twice — unstructured freedom
25:05 – The joy of having no plan
26:25 – Driving across the Great Salt Lake (the slightly risky part)
27:11 – Why unstructured time matters after a big exit
27:31 – Realizing he wasn’t “done” with tech or Silicon Valley
27:57 – Three years later: is he happy?
28:07 – Business as a game, not just work
29:32 – Creator vs operator: early-stage founders must be both
32:41 – Did his son influence the decision to start another company?
33:58 – Modeling meaning and fulfilment for children
36:08 – Why he became an entrepreneur in the first place
36:14 – Graduating into the 2008 crisis
36:40 – Discovering startup life and loving the creative chaos
38:23 – It wasn’t about money — it was about people
40:49 – Two failed startups in a row: learning without financial reward
41:11 – Motivation after exit: still driven by curiosity, not fear or money
42:13 – Curiosity as the true engine behind building companies
43:17 – Why no single motivator is enough to build a company
45:01 – “Stay hungry, stay foolish” — Daniel’s interpretation
46:36 – Work-life balance vs. work-life integration
46:45 – How he designs balance in his second company
48:40 – Why remote culture supports family life
49:26 – How much he actually works
49:35 – Comparing work intensity: first company vs second
50:16 – Why he set up the company so co-founders push each other
50:22 – Returning to fulfilment: the moving target
51:00 – The mountain metaphor: why fulfilment never stays
52:07 – What a “10 day” looks like for Daniel
53:42 – Finding joy in the small things
53:59 – Why the end goal will never create long-term fulfilment
54:18 – “How do you want to be remembered?”
54:29 – Family, impact, and acceptance
56:16 – Graveyards, billionaires, and perspective on legacy
57:13 – Closing reflections & farewell

On the one hand, enjoying the incredible lifestyle we've earned. On the other, protecting and growing the wealth it took so much to build. 

My friend Justin Donald has lived that tension and he wrote a best selling book about it and created a community called Lifestyle Investor to help others walk the same path. It's easy to dismiss the drive for more financial success once we've already had an exit. But Justin shows us it doesn't have to be a choice and fulfillment can live side by side. 

Today he shares his story, his hard earned insights and the way he's chosen to live his own life.

He shares what he’s learned from their stories: what works after an exit and what does not.  

Barak is now partner at VC firm Vine Ventures in New York City and Tel Aviv.

Connect with Barak:
Linkedin: https://www.linkedin.com/in/barakk/
X: @barak-kaufman
PEF: https://pef.xyz/
Vine Ventures: https://vineventures.com

Connect with Anastasia: 
Linkedin: https://www.linkedin.com/in/anastasiakoroleva
X: @AnasKoroleva
Newsletter: https://www.exitparadox.com/blog
About Anastasia: https://www.exitparadox.com/about

Listen to Exit Paradox Podcast:
Apple Podcasts: https://podcasts.apple.com/us/podcast/exit-paradox/id1719806072
Spotify: https://open.spotify.com/show/7cC1er82lJBviXe6qjM158

Dan Berger's story is one of those. Seven years ago, he sold social tables for around $100 million million dollars. And like so many of us, the exit cracked something open. The wealth, the time, the freedom. It didn't bring peace at first. It made things worse. Den spiraled into addiction, sex and porn. But he soon realized the pleasure they gave him was too fleeting, too empty. It did nothing to meet his real needs. That's when Den realized that his Exit wasn't just a big win. It was a chance to create something he'd never truly had. Real sense of belonging. 

Today, years later, he finally has it. He has finally built it. Then is a story of real courage. The courage to confront his darkest demons. Childhood trauma, bipolar disorder, Chronic anxiety. The patience and resilience to get to the root of his pain. 

This is one story you really don't want to miss.

00:00:00 Intro
00:01:55 Life After Selling Social Tables 
00:02:25 Loss of Belonging Post-Exit 
00:03:53 Failed Attempts to Recreate Work Identity 
00:05:05 Belonging & Addiction 
00:06:42 Why He Wasn’t Aware of His Needs 
00:09:43 The Crossroads Moment and Reinventing Identity 
00:13:23 Dan’s Framework for Belonging 
00:18:10 Can Our Belonging Archetype Change? 
00:22:43 Dan’s Belonging Tank Today 
00:25:02 How Dan Defines Belonging 
00:32:01 Sex Addiction and Its Roots in Belonging 
00:36:22 Getting Help: 12-Step Recovery 
00:37:54 Why No One Talks About Sex Addiction 
00:39:44 Loneliness, Belonging & the Male Crisis 
00:42:52 Raising Boys and Masculinity Today 
00:45:14 Switching Gears: The Financial Impact of Exit 
00:48:49 Die With Zero: A New Financial Philosophy 
00:53:23 Purpose, Not Just Experience 
00:56:00 New Venture: Offsite Retreat Venues 
00:57:38 Lessons from Social Tables to New Business 
00:59:12 Dan’s Business Archetype: Operator 
01:00:12 The Risks of Using Own Money 
01:01:19 Writing a Book: Process and Pitfalls 
01:03:20 What's Special About Dan's Book 
01:04:07 How Dan Wants to Be Remembered

Amy Castoro helps families have honest conversations about wealth—the kind most of us were never taught to have.

She shares practical tools from her firm’s 50 years of experience advising some of the wealthiest families in America. 

Her work focuses on the emotional side of money—how we build trust, protect our closest relationships, speak openly, and prepare the next generation to handle wealth well.

We talk about raising children with money and how to rethink our own relationship with it after a successful exit.

It’s one of the most useful conversations I’ve had. Amy’s views challenged my own.I hope it helps you as much as it helped me.

00:01:59 Amy’s Background & Work with the Williams Group

00:03:30 Why 70% of Families Fail at Wealth Transition

00:05:18 Trust, Communication & Heir Preparedness

00:08:18 How Early Should Kids Be Taught About Wealth?

00:10:31 Age-Appropriate Conversations About Philanthropy

00:13:17 Creating Motivation Without Financial Desperation

00:16:23 Responding to Kids Asking About Inheritance

00:20:35 Involving Children in Wealth Management Early

00:22:33 Teaching Kids to Say “No” & Handle Peer Pressure

00:26:44 Skills Young Heirs Often Feel They Miss

00:29:09 Should Children Be Encouraged to Be Entrepreneurs?

00:32:28 What If the Family Came into Wealth Late?

00:36:04 First Family Meeting: What to Discuss

00:37:28 Re-engaging the “Unmotivated” Youngest Child

00:40:29 Coaching vs. Therapy in Wealth Transition

00:41:41 Families with Young Kids: How to Start Early

00:44:33 Relationship Skills & Communication Patterns

00:47:06 Why the Skills That Build Wealth Won’t Transition It

00:48:20 Balancing Entrepreneurship & Parenting Post-Exit

00:50:39 Modeling Purposeful Wealth, Not Just Growth

00:54:36 What Successful Families Say the Purpose of Wealth Is

00:56:49 Defining Family Values Around “Education”

00:58:41 Reconciling Different Values in the Family

00:59:50 Allowance Strategies in Wealthy Families

01:01:38 Knowing When to Shift from Parent to Mentor

01:03:28 Creating & Living a Family Mission Statement

01:06:06 New Program: Next Gen Leaders

01:07:25 Common Mistakes Families Make Around Wealth

01:10:34 Should Families Hold Regular Meetings?

01:12:37 The #1 Shift Families Must Make for Success

01:13:38 Amy’s Recommended Books on Family Wealth

01:15:15 Final Thoughts: Preparing the Family for the Assets

Why did he choose this path? What has he learnt so far? Was it the right move?

For a while, Jay also co-hosted The Joyful Entrepreneur Podcast—a top 10 show about success and happiness.Today, we explore how Jay is designing his venture studio not just for financial success—but for joy, purpose, and meaning.And what he’s learned from both his own journey and the many post-exit founders he works with.

_____________________________________________________
00:00:00 - Introduction
00:04:23 - Emotional journey post-exit
00:06:00 - Experiencing emptiness despite success
00:07:15 - Defining the Post-Exit journey (Pause, Reset, New Chapter)
00:08:15 - Avoiding the corporate trap post-sale
00:09:35 - Discovering he's not a CEO type
00:10:15 - Founding Blissgrowth and love for early-stage building
00:11:30 - Venture Studio vs Angel Investing and Accelerators
00:13:15 - Pros and cons of running a Venture Studio
00:15:15 - Team dynamics and focus of Blissgrowth
00:16:45 - Common misconceptions about Venture Studios
00:17:45 - How his studio compares to others
00:19:15 - Angel investing vs Venture Studio involvement
00:21:15 - Journey from emptiness to fulfillment
00:23:15 - Connecting with intuition through stillness and yoga
00:25:15 - Daily practices to cultivate inner clarity
00:26:60 - The power of quiet and introspection
00:28:15 - Rewiring mindset and deep inner work
00:30:00 - Changing his relationship with fear
00:31:30 - From fear to freedom and growth
00:33:00 - The psychology of purpose and contribution
00:34:15 - Observations on other exited founders and finding purpose
00:35:45 - Why decoding purpose is a unique journey
00:37:15 - Role of spirituality and Indian heritage in self-discovery
00:39:45 - Spirituality as a path to love and connection
00:41:15 - Overcoming skepticism and redefining success
00:43:15 - AI, intellect, and spiritual work
00:44:15 - Creating and renaming his podcast: Joyful Entrepreneur
00:46:15 - Why he paused podcasting despite success
00:47:45 - Lessons learned from podcasting
00:49:15 - The power of public self-expression for exited founders
00:50:45 - Normalizing post-exit struggles in the founder community
00:52:15 - Redefining success after financial freedom
00:53:45 - Jay’s 5-pillar framework for purpose
00:55:45 - How Blissgrowth aligns with his purpose
00:57:15 - Building to scale vs building to exit
01:00:15 - Should founders build with an exit in mind?
01:01:45 - Jay’s commitment to Blissgrowth long-term

00:00 - Introduction and reflections on Linda’s first business exit
03:34 - Selling Peregrine Technologies and emotional response
04:36 - Starting the next venture and skills assessment
05:55 - Creating comScore and early funding story
08:11 - Frugality and surviving the dot-com crash
10:30 - Pivot to audience measurement and analytics
11:36 - Selling data to financial institutions like Citadel
11:59 - IPO and financial outcomes for the team
13:00 - Motivations beyond money and public company growth
14:01 - Leaving comScore and reflections on career satisfaction
15:10 - Post-exit transition and board work
17:09 - Realizing need for a break and pulling back from overcommitment
18:19 - Shift to board advisory roles and family balance
18:49 - Motherhood and managing with four children
20:09 - Family-first values and support system
21:48 - Daily decision-making and sacrifices
24:49 - Health and lifestyle improvements post-exit
27:25 - Transitioning from entrepreneur to investor
29:01 - Challenges in board work and mindset shifts
31:18 - Finding joy and variety in board roles
33:42 - Investing in second-time founders and founder motivations
38:15 - Raising children with wealth and aligned values
40:50 - Reflections on adult children and family discussions
43:07 - Delaying wealth conversations and individual approaches
46:21 - Continuing involvement in husband’s new startup
48:04 - Evolving motivations and contribution style
49:42 - Creating balance through mindful time management
52:45 - Focus on impact and strategic contribution
56:12 - Mentorship, support, and satisfaction in giving back
57:60 - Work, family, community: expanded arc of purpose
59:58 - How Linda wants to be remembered
01:01:14 - Conclusion and farewell

00:00:00 – Introduction & Adam’s Exit Story
00:01:06 – Why Exited Founders Make Bad Investors
00:05:15 – From Angel Investing to Private Equity
00:09:00 – Why Most Second Companies Fail
00:10:15 – Lessons from a Failed Acquisition
00:12:07 – Buying vs. Building a Business
00:14:34 – Regret After Exit and Finding New Purpose
00:17:27 – Sacrifice, Purpose & The Next Big Thing
00:20:18 – Impact, Meaning & Philanthropy Struggles
00:23:44 – Coaching Entrepreneurs as a Calling
00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet
00:27:00 – Kids, Family, and Timing the Next Move
00:29:00 – Angel Investing: Rise and Decline
00:31:06 – The Illusion of Control in Angel Investing
00:32:35 – Advice for New Angel Investors
00:34:45 – Lifestyle Balance Post-Exit
00:36:00 – The Grind Years: 20-Hour Days and Stress
00:38:00 – Building a Business with His Wife
00:41:30 – Division of Labor and Complementary Skills
00:43:00 – Conflict Resolution in a Husband-Wife Team
00:44:45 – Why They Didn't Start a Second Business Together
00:46:15 – Raising Entrepreneurial Kids with Wealth
00:50:45 – The Only Real Passive Investing Strategy
00:53:26 – Life Rules: Wealth vs. Freedom
00:56:40 – Is Balance Between Mission and Freedom Possible?
00:58:45 – Mental Health After the Exit
01:01:00 – Why He Shares His Story Publicly
01:03:15 – A Book for His Kids and Maybe the World
01:07:17 – Will He Publish It?
01:09:41 – How Adam Wants to Be Remembered
01:10:36 – Closing Thanks & Final Reflections

Today we are talking about what he's learned and why he decided to dedicate himself to coaching. 

🔗 CONNECT WITH MIKE:
🎥 YouTube Channel - ‪@mbrown_co‬
🐦 X (Twitter) - https://x.com/mbrown_co
📸 Instagram - @mbrown.co
💻 Website - https://unbreakablewealth.com/👥
Linkedin -   /mikebrownactual  

TIME STAMPS:

00:00:00 – Introduction

00:00:37 – The Aftermath of Selling a Business

00:02:07 – Reality Hits: The Post-Exit Crisis

00:03:19 – The Connection Between Entrepreneurship and Divorce

00:05:00 – Chasing Achievement vs. Finding Purpose

00:06:40 – Could He Have Saved His Marriage?

00:08:33 – What’s Next After the Exit?

00:09:59 – Why Coaching and Why It Almost Didn’t Happen

00:10:34 – A Costly Distraction: A Failed Investment

00:12:30 – The Emotional Weight of Money and Investing

00:15:00 – A Brutal Financial Loss: Losing $100K a Month

00:18:00 – The Transition from Founder to Investor

00:20:15 – The Importance of Financial Safety Nets

00:24:15 – Balancing Risk and Stability

00:29:00 – The Concept of Wealth Beyond Money

00:30:06 – Unlimited Freedom vs. Purpose

00:32:03 – Defining Purpose and Service to Others

00:36:00 – The Danger of Retiring Too Early

00:40:00 – Lessons from Childhood: How Early Experiences Shaped His Drive

00:46:00 – Parenting and Entrepreneurship

00:52:25 – Post-Exit Traps to Avoid

00:57:45 – Rebuilding Structure and Identity After an Exit

01:06:00 – Final Lessons: The Power of Stillness

01:07:22 – How Mike Wants to Be Remembered

Yet, the Lazerows defied that norm—building not just one, but two successful companies together, culminating in an $800M exit.

They didn’t just make it work; they mastered it—and then wrote a book about it.

Today, we’ll dive deep into what exactly they did to make it work—and what they wish they hadn’t.

TIME STAMPS:

00:00:01 - Introduction

00:00:14 - Learning from Failure vs. Success

00:00:27 - Building a Business as a Married Couple

00:01:08 - First Meeting and Early Impressions

00:02:30 - Life After an Exit

00:03:08 - Golf.com: The First Big Exit

00:06:58 - The Struggles of Entrepreneurship

00:09:14 - The Emotional Toll of Entrepreneurship

00:10:35 - Taking a Break After an Exit

00:11:14 - Was Their First Exit Life-Changing?

00:12:54 - Why Start Another Business?

00:14:31 - Entrepreneurship with Three Kids

00:16:47 - Why Entrepreneurs Keep Going

00:19:41 - Becoming Investors

00:23:20 - The Hardships Behind Entrepreneurship

00:28:17 - Coping with Post-Exit Stress

00:31:41 - Entrepreneurs and Mental Health

00:34:55 - Reframing Anxiety & ADHD as Superpowers

00:38:46 - The Dark Side of Entrepreneurship

00:44:01 - Work-Life Balance: Do They Have One?

00:48:01 - Michael’s Attempt at a Painting Career

00:50:12 - Filtering Opportunities

00:52:28 - Navigating Marriage After an Exit

00:55:15 - Raising Kids with Wealth

01:02:11 - Teaching Kids About Money and Responsibility

01:09:04 - The Purpose of Their Book

01:11:20 - Final Question: How Do You Want to Be Remembered?

🔗 CONNECT WITH KASS AND MIKE:

👥 Linkedin KASS - https://www.linkedin.com/in/kasslazerow/

🐦 X (Twitter) KASS -  https://x.com/kasslazerow

👥 Linkedin MIKE - https://www.linkedin.com/in/lazerow/

🐦 X (Twitter) MIKE -  https://x.com/lazerow

💻 Website (personal) -  https://www.kassandmike.com/

I📸 Instagram: https://www.instagram.com/kassandmike/

TikTok: https://www.tiktok.com/@UCgLzz0yep6lUaE5i62zMXTw 

🎥 YouTube Channel: https://www.youtube.com/@UCgLzz0yep6lUaE5i62zMXTw 

🔗 CONNECT WITH ANASTASIA: 

🎥 YouTube Channel - https://www.youtube.com/@UCaoC4W9E2Vopnkd-K3dOw7Q t

🐦 X (Twitter) -  https://x.com/AnasKoroleva  

📸 Instagram -  https://www.instagram.com/anastasiashoot

💻 Website -  https://www.exitparadox.com

🗞️ Newsletter - https://www.exitparadox.com/blog

👥 Linkedin -  https://www.linkedin.com/in/anastasiakoroleva

TikTok - https://www.tiktok.com/@anastasia.korolev7

A huge milestone - but as all exited founders know, the real story starts after the deal is done.Today, he’s building again - but with a completely different approach.

Josh isn’t optimizing for another massive exit. He’s after something bigger. So let’s see what we can learn from this fascinating man.

00:00:00 Introduction
00:00:45 Selling StackCommerce: Was It a Happy Moment?
00:02:00 The Emotional Impact of Selling a Company
00:03:30 Why Money Didn’t Solve Everything
00:05:15 Prioritizing Family After the Exit
00:06:30 Leaving the Company: A Tough Identity Shift
00:07:45 Taking a Healing Family Trip
00:09:00 Training for an Ironman & Overcoming Mental Barriers
00:12:30 Decoupling Identity from Business
00:14:00 Leadership & Purpose Beyond Business
00:16:00 Sacrifice vs. Suffering in Entrepreneurship
00:18:45 Ironman Training: Lessons in Overcoming Fear
00:22:00 The Challenge of Finding a New Purpose
00:23:45 Why Start Another Business After an Exit?
00:27:00 Learning to Build a Company Without Fear
00:30:00 The Difference Between First and Second Businesses
00:33:00 Finding a Sustainable Way to Build Again
00:35:00 Balancing Business & Personal Life After Exit
00:38:15 Why Many Second Businesses Fail
00:42:00 The Importance of Motivation in a New Startup
00:45:30 Avoiding the Trap of Losing Interest Midway
00:48:00 The Role of Peer Groups Like Tiger 21
00:50:30 How Long Does It Take to Truly Adjust After Exit?
00:53:00 Raising Kids With Wealth: Teaching Responsibility
00:54:00 Closing Thoughts & Future Plans

This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why?

Well, Alex has seen enough of his post-exit founder friends getting stuck in full-blown existential crisis after they sold their company. He didn't want that to happen to him. 

In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL.

00:00:00 - Introduction

00:02:25 - The Story of Velocity Black

00:07:46 - Selling Velocity Black to Capital One

00:07:05 - Why Alex Started Another Business Before Selling His First One

00:10:52 - The Founder’s Existential Crisis After an Exit

00:12:45 - The Shortage of Builders, Not Investors

00:14:19 - Work-Life Balance & Health After an Exit

00:16:21 - Lessons from Running a 24/7 Business

00:19:52 - Changing Approach to Work with Sequel

00:21:19 - Different Approaches to Post-Exit Businesses

00:24:19 - Sequel: Building a Next-Gen Goldman Sachs

00:27:26 - Managing Motivation After Financial Success

00:31:03 - Fulfillment vs. Happiness: What Really Matters?
00:33:15 - The Biohacking & Longevity Obsession

00:35:51 - Community & Meaning in Life After an Exit

00:39:13 - The Idea of Creating a New Religion

00:45:46 - The Role of Structure & Responsibility in Life.

00:54:08 - The Challenge of Freedom After an Exit

00:57:46 - Angel Investing & How It Led to Sequel

01:03:42 - Helping Athletes Transition Beyond Their Careers

01:07:37 - Building a Legacy vs. Just Making Money

01:10:52 - Avoiding Mistakes in Early-Stage Investing

01:15:30 - The Power of Influence in Investing

01:20:05 - Sequel’s Future Plans & Scaling the Model

01:25:00 - What Drives Long-Term Success?

01:30:10 - Final Thoughts & Advice for Founders

Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. 

Everything changed when Cory went back to building and working. But this time it felt different. 

His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment. 

Today, Cory finally feels deeply fulfilled, energised and joyful. 

There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life.
 _____________________________________________________ 
00:00:00 Introduction
00:01:40 Guest Introduction: Cory Janssen’s Story
00:04:00 Founding Investopedia: The Early Days
00:10:55 Deciding to Sell Investopedia
00:22:15 Regret After Selling: Financial and Emotional Impact
00:35:10 Working for the Acquirer: Lessons Learned
00:46:50 Negotiating the Sale Process: Tips for Founders
00:56:20 Post-Exit Struggles: Managing Wealth and Purpose
01:07:10 Challenges of Professional Investing
01:15:30 Rediscovering Passion for Building: Transitioning to AI
01:26:15 Balancing Parenthood and Entrepreneurship
01:37:30 Raising Kids with Wealth: Avoiding Entitlement
01:40:00 Closing Reflections and Key Takeaways

Michael Miller has been a friend for over 15 years and has made a huge difference in my life. 

He's a Vedic meditation teacher who taught me to meditate at a time when I was searching for clarity and tranquility following a life-changing exit. Since then, meditation has been my go-to tool for healing, finding peace, processing ideas, and making decisions. 

And it's not just me, people like Jack Dorsey, Bill Gates, Arianna Huffington, and Ray Dalio all credit meditation for helping them on their own post-exit journeys. 

Before discovering his calling as a meditation teacher, Michael had a successful business career. That experience gives him a unique ability to explain meditation in ways that make sense to us entrepreneurs. 

If you've tried meditation before, but let it slip, this might just inspire you to pick it back up.

 _____________________________________________________ 
00:00 The Healing Power of Meditation
02:46 Personal Journeys and Transformations
06:10 The Science Behind Meditation
11:54 Meditation as a Decision-Making Tool
17:49 The Ripple Effect of Meditation
24:06 Creating Peace from Within
40:07 The Ripple Effect of Inner Peace
44:51 The Journey of Personal Growth Post-Success
49:52 Addiction as a Spiritual Search
52:15 From Material Success to Fulfillment
59:33 Designing a Toolbox for Holistic Leadership
01:13:30 The Journey of Self-Discovery
01:18:05 Navigating Life Stages and Transitions
01:23:25 Embracing Discomfort for Growth
01:29:35 The Role of Community and Giving Back
01:34:08 Traveling with Purpose
01:39:23 Understanding Consciousness
01:42:34 Defining Purpose and Connection

_____________________________________________________ 
00:00:00: Introduction and greetings
00:01:04: Sarah's business journey beginnings (Music school)
00:01:39: Transition to selling online (Discovery at dinner)
00:02:04: Starting with camping gear (Wise Owl Outfitters)
00:02:56: Challenges and operations (Traveling to China)
00:03:40: Balancing family and business (Moving and kids)
00:04:23: Working with her husband
00:05:21: Husband's role and career shift (Becoming a painter)
00:04:37: Decision to sell the business
00:05:00: Influences and reasons for selling
00:07:01: Financial freedom and exiting strategy
00:08:16: The selling process (Timeline and logistics) 
00:09:56: Reflections on the buyer's bankruptcy 
00:11:06: Emotional impact of selling 
00:12:10: Post-sale challenges and burnout 
00:13:23: Realizations and health impact 
00:14:40: Personal and existential reflections 
00:16:55: Seeking and understanding contentment 
00:18:37: Advice on spirituality and life direction 
00:19:06: Initial thoughts on spirituality and personal development 
00:19:23: Exploring different avenues for growth 
00:19:46: Impact of personal coaching and physical health 
00:20:36: Reflection on life's purpose post-exit 
00:21:32: Evaluating new opportunities and the allure of starting new businesses 
00:25:00: Importance of being helpful to others 
00:27:18: Finding balance in life and prioritizing oneself 
00:27:50: Balancing motherhood and business 
00:32:17: Handling wealth and teaching children about money 
00:34:42: Shifts in business motivation without the need for money 
00:38:17: Importance of having a supportive team 
00:39:08: Pursuing new, exciting projects 
00:40:02: Balancing current business with new ventures 
00:40:26: Benefits of taking extended trips 
00:42:04: Discovering oneself through new experiences 
00:46:04: Reflections on legacy and impact on others 
00:48:02: Interpretation of "Stay hungry, stay foolish" 
00:51:03: Struggles of balancing business and family as a woman 
00:56:06: Comparison of post-exit life to athletes' career transitions 
00:56:38: Feeling lonely during the process 
00:56:52: Searching for information online 
00:57:15: Conclusion and thank you

_____________________________________________________
00:00:00 - 00:00:39 Introduction
00:00:39 - 00:02:58 Tim Schumacher's Exit and Reflections
00:02:58 - 00:05:58 Transition to New Ventures
00:05:58 - 00:07:28 The Importance of Rest and Work-Life Balance
00:07:28 - 00:09:51. Personal Interests and Climate Change
00:09:51 - 00:11:55. Evolution of Motivation and Values
00:11:55 - 00:16:38. The Bootstrap Mindset
00:16:38 - 00:18:28. Balancing VC and Bootstrap Approaches
00:18:28 - 00:25:30. Scaling vs. Building from Scratch
00:25:30 - 00:29:37. Financial and Purposeful Integration
00:29:37 - 00:31:12 Managing Identity Change Post-Exit
00:31:12 - 00:37:05 Work-life Balance and European Influence
00:37:05 - 00:36:59. Entrepreneurial Legacy and Family
00:36:59 - 00:42:20. Reflecting on Business Strategies and Learnings
00:42:20 - 00:45:26 Revisiting Entrepreneurial Failures
00:45:26 - 00:47:09. Cultural Exposure and Entrepreneurial Growth
00:47:09 - 00:49:29 Purpose and Motivation Beyond Business

A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. 

In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. 

Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth.

_____________________________________________________
00:00:00: Introduction 
00:00:21: The paradox of success 
00:00:43: Rick's background and contributions 
00:01:04: Discussion on post-exit rebirth and struggles 
00:01:12: Exploring dopamine addiction and post-success frustrations 
00:02:30: Exploring the post-exit maze 
00:02:45: Rick's background and experience with exited founders 
00:04:47: Rick's critical event with Vistage group 
00:06:09: The price and prize of money and freedom 
00:07:52: Reflections on the dual meaning of success 
00:08:53: Grappling with post-exit paradox 
00:09:41: The "focusing illusion" and the arrival fallacy 
00:11:12: The societal pressure to be happy post-exit 
00:12:01: Support groups and legitimating experiences 
00:13:08: Initial reactions and reflections on the post-exit reality 
00:14:31: The societal issue of ignoring exited founders 
00:15:33: The lack of support and self-blame post-exit 
00:18:00: Escaping the blank sheet of paper 
00:19:07: Dealing with loss of motivation 
00:20:38: The challenge of striving without a company 
00:22:21: Stories of loss of identity and success paradox 
00:23:02: The impact on identity and structure post-exit 
00:24:29: Avoiding the inclination to fill the void with the same elements 
00:25:32: Closing the first business 
00:26:18: Question of true desires and freedom paradox 
00:27:19: Attempt to create a model from experiences 
00:29:06: Journey from identity to meaning and structure 
00:30:02: Revisiting personal development opportunities 
00:33:16: Financial dangers post-exit 
00:35:30: Paradox of money and its role 
00:36:09: Evolution of the meaning of wealth 
00:41:03: Refusal of the call and negative transfer of learning 
00:44:10: Dopamine addiction as an obstacle 
00:47:00: Fear of losing entrepreneurial identity 
00:49:00: Navigating the journey of death and rebirth in personal growth 
00:51:13: Leaving people behind during personal growth 
00:52:29: Real journeys begin where fairy tales end 
00:54:08: Redefining retirement and societal expectations 
00:56:03: Advising young successful entrepreneurs 
00:57:23: Identifying and addressing emotional struggles post-sale 
00:58:46: Embracing a Mosaic Life 
01:00:00: Communicating personal transitions to others 
01:03:07: Returning to business after personal growth 
01:05:00: Listening for truth, vitality, and fear in decisions 
01:07:32: Distinguishing between legitimate fears and psychological barriers 
01:09:08: Discernment of skill-related fears in new ventures 
01:10:14: Transitioning from entrepreneur to investor 
01:13:20: Rediscovering a sense of purpose post-exit 
01:14:00: The search for meaning and what matters now 
01:16:22: Two ways of knowing and going: Destination vs Direction 
01:17:57: Understanding fulfillment and satisfaction 
01:19:20: The importance of savoring moments 
01:21:00: Stories about finding fulfillment 
01:23:26: Legacy question 
01:24:00: Discussion about dynamics of arrival 
01:27:00: The role of intention in satisfaction

He barely knew his family anymore. 

So he and his wife pulled their kids out of school, packed up. and set off on an open-ended journey around the world. For 14 months, they traveled without a plan, letting each destination choose them and discovered what freedom really meant. When they returned, threw himself into the challenge of cycling and completed an Ironman. 

He also started an angel investment firm to stay intellectually engaged. He has built a beautiful life, but now 13 years post-exit, he is still looking for a new purpose. 

Roy is torn between the urge to build something big again and the fear of sacrificing his family and lifestyle. Roy is disarmingly open and witty in this conversation. His ideas on personal growth, leadership and fulfillment are fresh and thought-provoking. 

_____________________________________________________
00:00:00: Introduction and greetings
00:01:38: Roy's background and introduction to Magento 
00:02:3: The founding and growth of Magento 
00:03:36: Why Magento was sold to eBay 
00:05:28: Reflections on selling Magento 
00:05:53: Period after selling: Working at eBay 
00:06:51: Challenges and experiences at eBay 
00:10:18: Frustrations and limitations at eBay 
00:11:07: Difficulty in leading within eBay 
00:13:39: Reflections on regret and learning from the experience 
00:15:53: Pain of working at eBay 
00:18:04: Changes in the leadership team post-acquisition 
00:19:25: Leadership style and inspiration 
00:22:07: Transparency and leadership approach 
00:25:24: Personal reflections post-exit 
00:25:48: Reflecting on leaving Magento in 2013 
00:28:03: Deciding to leave eBay after Magento's Imagine conference in 2014 
00:29:15: The decision to travel with family for 14 months 
00:30:00: The travel route through Central America, South America, Asia, and Europe 
00:31:03: The travel experience and its impact on family dynamics 
00:36:04: Encouragement to other founders to take time off and travel 
00:43:02: Discovering new passions post-travel, specifically Iron Man and cycling 
00:45:59: Introduction to Personal Journey 
00:46:26: Discovering Passion for Sports 
00:46:10: Reinventing Post-eBay Life 
00:46:44: Starting the Fund During COVID 
00:48:04: Transition to Angel Investing 
00:51:27: Managing Wealth Post-Magento Sale 
00:54:03: Investment Philosophy and Public Equities 
00:56:45: The Non-Financial Rewards of Investing 
00:58:17: Search for Purpose Beyond Business 
01:01:27: Reflection on Purpose During Magento Years 
01:03:33: Balancing Life with Current Ventures 
01:06:12: Discussing a life of 24/7 dedication 
01:06:47: The search for purpose 
01:08:01: Meeting new people 
01:10:00: The intense journey with Magento 
01:12:56: Coping with the transition post-acquisition 
01:16:07: Being a creator versus an operator 
01:19:11: Future impact and legacy 
01:22:10: The desire for more meaningful work 
01:26:21: Closing remarks and goodbyes

It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook. 

In this episode, Brock talks about the secrets behind his consistent success, what keeps him optimistic and gives him a sense of purpose, and how he cultivates relationships in both business and private life.

_____________________________________________________ 
00:00:00: Introduction
00:01:17: Brock's first company exit experience
00:03:02: Transition challenges after the exit
00:03:31: Acquisition by PetSmart and transition experience
00:06:00: Acquisition of PetCoach
00:07:45: Brock's role and relationship with PetCoach team
00:08:59: Insights on being a startup to grown-up stage founder
00:09:41: Brock's involvement in subsequent businesses
00:11:00: Selling Great Pet Care due to MS diagnosis
00:11:56: Diagnosis impact on priorities and motivations
00:13:09: Adjusting to life with MS
00:14:38: Post-exit reflections and personal journey
00:15:41: Engaging with the business community in new ways
00:16:27: Realignment of life and business perspectives
00:21:47: Reflections on Sharing Knowledge and Purpose
00:22:08: Importance of Meaningful Involvement and Family Time in Purpose
00:22:26: Daily Approach to Living Purposefully
00:24:10: Impact of Diagnosis on Relationships and Support System
00:26:07: Friends' Support During a Difficult Time
00:26:54: Tracing the Evolution from First Business to Present
00:27:03: Story of the First Business Failure
00:30:02: Lessons Learned from Business Failures
00:31:15: The Role of Investors and Ethics
00:35:59: Challenges of Transitioning from Owner to Employee Mentality
00:38:24: Celebrating Failures and Learning from Them
00:40:52: Keeping Perspective in Business Ventures
00:41:14: Adapting and Learning in New Environments
00:42:48: Introduction to the CEO’s vision
00:44:09: Staying humble and continuing to learn 
00:51:22: Balancing experience and youthful energy 
00:52:06: The importance of continuous learning 
00:54:01: Past performance vs future success 
00:56:15: Building successful teams 
00:59:55: The value of the cap table and smart investment decisions 
01:02:22: Financial considerations and risk profiles 
01:03:27: Final advice for building a new business after an exit 
01:02:50: Being intentional in business and personal life 
01:03:11: Setting personal intentions and accountability 
01:04:25: Specific goals and realistic expectations 
01:06:00: Applying business discipline to personal life 
01:07:15: Correlation between personal and professional success 
01:08:08: Open communication and its importance 
01:09:19: Achieving balance and happiness 
01:09:22: How to be remembered

Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. 

Scott is a natural creative who sees building a business as an artistic endeavor. 

It was this intrinsic need to create that sustained him through the grueling journey of building his business. Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created. 

In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children.

_____________________________________________________
00:00:00: Introduction and welcome to Scott 
00:01:11: Reflections on selling the company 
00:02:22: Feelings post-sale and personal identity 
00:05:01: Comparing business to art 
00:06:58: Transition from attorney to entrepreneur 
00:08:57: Founding and growing Levelset 
00:11:15: Key roles and talents in the company 
00:13:21: Starting a new business and family considerations 
00:19:00: Debating the reasons to start another business 
00:21:02: Seeking purpose and fulfillment 
00:23:21: The necessity of creativity and purpose 
00:24:06: The challenges of balancing personal and professional life 
00:25:01: The paradox of purpose 
00:26:31: Rebuilding life and purpose post-exit 
00:27:56: Adjustments and surprises after exiting a company 
00:29:02: Facing mortality and existential reflections post-exit 
00:31:36: Managing personal expectations and regrets 
00:34:07: Reflecting on unfinished business and the non-finality of accomplishments 
00:38:03: The journey and appetite for creative endeavors 
00:40:44: Exploring new experiments and hobbies post-exit 
00:42:28: Writing and reflecting on vision after business exit 
00:43:32: Building and helping companies after the exit 
00:45:08: Structuring the company's vision 
00:45:48: Financial exit and its impact 
00:47:25: Managing newfound wealth 
00:54:58: Becoming a cautious investor 
00:56:00: The hedgehog concept 
00:58:53: The influence of entrepreneurial family upbringing 
01:01:42: Wishing entrepreneurial experiences for children 
01:05:32: The importance of self-reliance and vision for entrepreneurs 
01:06:22: Strategy Development and Investment Philosophy 
01:08:07: Changes in Motivation Over Time 
01:10:40: Current Motivation and Challenges 
01:13:36: Inspiration and Choosing People to Surround Yourself With 
01:14:21: Building a Network Organically 
01:16:33: The Importance of Purpose and Motivation 
01:17:49: Reflections on Authenticity and Meeting New People 
01:18:04: Legacy and How to be Remembered

_____________________________________________________
00:00: Introduction 
01:00 Transition after selling the company 
01:20: Jonathan's unconventional wisdom 
02:08: Jonathan's previous careers 
03:06: Motivation for starting a new business 
03:53: Challenges faced in hierarchical systems 
04:44: Importance of money in decisions 
05:47: Founding a data business 
06:44: Challenges in raising money 
08:24: Misconceptions about data 
10:03: Advantages of bootstrapping 
11:14: Financial challenges and salaries 
14:53: Impact of minority exit in 2016 
17:02: Reasons for full business exit 
18:12: Dividend checks and responsibility 
19:04: Working with private equity firms 
21:04: Importance of choosing the right partner 
22:10: Reflections on Exiting During COVID 
23:00: Health Issues and Impact on Business 
24:03: Regrets and Decisions on Exiting 
25:10: Continuing Involvement Post-Exit 
26:14: Merging with a US Company 
27:02: Adjusting to Life After Business 
28:32: Personal and Family Focus Post-Retirement 
30:26: Supporting Academic Research and Mental Health 
31:29: Motivation of Wealth Training for Children 
35:17: Disinterest in Material Possessions 
38:13: Sources of Fulfillment and Life Satisfaction 
41:47: Outdoor Activities and Personal Well-being 
42:00: Processing Life's Experiences into Wisdom 
45:36: Small experiences of delight 
46:12: Caring for employees through share options 
46:50: Satisfaction from contributing to others' happiness 
47:08: Reflection on being remembered 
48:04: Conclusion and gratitude

Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, health and meaningful work. 

This shift inspired him to found Thunder, a tech enabled investment bank and launch the fundraising demystified podcast. In this interview, Jason shares his journey from high stress startups to a life centered on fulfillment and purpose.

_____________________________________________________
00:00:00: Overview of Jason’s Expertise 
00:01:27: Starting Liquid Sky 
00:01:56: Formation and Operational Beginnings of Liquid Sky 
00:02:24: The Vision and Mission of Liquid Sky 
00:03:11: Partnership and Expansion Efforts 
00:03:37: Business Philosophy and Personal Contribution 
00:05:15: Diverse Industry Experience 
00:06:50: Curious Nature and Learning Process 
00:06:53: Liquid Sky’s Rapid Growth and Sale to Samsung 
00:08:05: The Failed Acquisition by Samsung 
00:10:17: Crisis and Pivot Strategy 
00:11:01: Final Attempts for Acquisition and Survival 
00:13:28: New Strategy with Walmart 
00:15:39: Outcome and Life Post-Acquisition by Walmart 
00:19:42: Excitement about Walmart Gaming 
00:20:25: Transition to San Diego and New Opportunity 
00:20:50: Introduction to Generation Esports 
00:21:48: Investing Energy into Generation Esports 
00:24:05: Initial Reflection and Momentum 
00:25:42: Navigating the COVID-19 Challenges 
00:26:28: Series A Funding and Rising Tensions 
00:29:06: Decision to Leave Generation Esports 
00:31:00: Self-discovery and New Relationships 
00:35:19: Learning from Relationship Dynamics 
00:36:00: Considering the Next Move 
00:36:10: The Idea of Starting Thunder 
00:36:42: The seed for Thunder 
00:37:18: What Thunder does 
00:39:02: Thunder as a tech-enabled investment bank 
00:40:21: Introduction to the podcast "Fundraising Demystified" 
00:42:00: Origin of "Fundraising Demystified" 
00:44:04: The value of understanding venture capital 
00:45:11: Advice for post-exit founders considering new ventures 
00:52:01: Importance of risk tolerance 
00:52:58: Determining the endgame for new businesses 
00:53:41: Plans for Thunder 
00:54:14: Decision against starting another big business 
00:55:04: Balancing career and family priorities 
00:55:48: Balancing Family and Ambitions 
00:56:07: Introduction to Entrepreneurship in College 
00:56:11: Influence of Successful Entrepreneurs 
00:56:35: Reflections on Success and Family Time 
00:56:39: Closing Remarks

Alongside his twin brother Nathan, he then acquired and transformed TruConnect into a telecom powerhouse. Matthew also co-founded the technology investment bank Drake Star Partners, leveraging his earlier investment banking experience in NYC. 

Balancing life between LA and Switzerland, he also leads a nonprofit providing wheelchairs to disabled children. Let’s dive into his unique post-exit lessons on staying motivated, enjoying life, and raising entrepreneurial children.

TIME STAMPS:

00:00:00 - 00:02:34 - Introduction and Career Transition

00:02:34 - 00:03:23 - The First Startup Experience

00:03:23 - 00:06:33 - Building True Connect

00:06:33 - 00:07:50 - Financial Discipline and Management Philosophy

00:07:50 - 00:12:42 - Transitioning from Finance to Entrepreneurship

00:12:42 - 00:15:08 - Balancing Multiple Ventures

00:15:08 - 00:19:05 - Considering Exiting True Connect

00:19:05 - 00:23:28 - Lessons in Hiring and Management

00:23:28 - 00:33:05 - Managing Investments and Personal Fulfilment

00:33:05 - 00:37:21 - Impact of Entrepreneurship on Family and Personal Life

00:37:21 - 00:41:06 - Raising Entrepreneurial Children

00:41:06 - 00:50:02 - Reflecting on Angel Investing

00:50:02 - 00:58:59 - Charity Work and Personal Fulfilment

00:58:59 - 01:08:21 - Life Philosophy and Future Goals

To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life. 

Two years ago, Bill moved with his family from Colorado to Portugal with no plans of returning anytime soon. 

Today we discuss this transformation, his craving for inspiration, creativity, simplicity, and soul-nourishing experiences. 

Connect with Bill 
Linkedin: https://www.linkedin.com/in/bflagg/

_____________________________________________________
00:00:00 - 00:03:36 - Introduction and Background 
00:03:36 - 00:04:31 - Transition to Sabbatical 
00:04:31 - 00:06:24 - Loss of Passion and Creativity 
00:06:24 - 00:07:45 - Embracing a Pause for Creativity 
00:07:45 - 00:11:11 - Living with Uncertainty 
00:11:11 - 00:16:16 - Rediscovering Life in Europe 
00:16:16 - 00:19:33 - Letting Go of Past Identities 
00:19:33 - 00:26:18 - Challenges with Possessions and Ownership 
00:26:18 - 00:29:03 - The Root Cause of Post-Exit Struggles 
00:29:03 - 00:31:13 - Embracing Retired Life 
00:31:13 - 00:31:38 - Family Perspective and Legacy 
00:31:38 - 00:33:22 - Final Thoughts

_____________________________________________________
00:00:00 - 00:03:12 - Introduction and Overview of Exits 
00:03:12 - 00:06:28 - Building and Selling MVC 
00:06:28 - 00:12:52 - Reflections on Investment and Entrepreneurship 
00:12:52 - 00:15:54 - The Impact of Personal Transformation and Pandemic 
00:15:54 - 00:23:35. Angel Investing and Adapting to New Roles 
00:23:35 - 00:32:13 - Personal Growth and Reflection 
00:31:13 - 00:35:18 - Ongoing Pursuit of Purpose and Legacy

Today, he manages a substantial real estate portfolio, invested in over 50 startups, and authored the book called Nightlife Lessons: How I Conquered the Business of Partying with Tech.

In this episode, Shane reveals the secrets behind his transition from the daily stress of running two businesses to achieving contentment and impressive financial success. 

Connect with Shane: 
Website: https://www.shaneneman.com/ 
X: / shaneneman LinkedIn: / shaneneman 
Instagram: / shaneneman 
YouTube: / @shaneneman 
Facebook: / nemanventures

_____________________________________________________
00:00 - 03:36 Introduction and Background 03:37 - 07:08 Early Entrepreneurship and Challenges 07:09 - 10:12 Growth and Evolution of JoonBug 10:13 - 13:02 Transition to EZTexting and Subsequent Sale 13:03 - 14:51 The Burnout and Decision to Exit EZTexting 14:52 - 21:05 Post-Exit Introspection and New Ventures 21:06 - 28:52 Investment Strategies and Mistakes 28:53 - 35:41 Personal Growth and Health Focus 35:42 - 42:54 Maintaining Balance and Family Life 42:55 - 51:07 Philosophical Insights and Ethical Reflections 51:08 - 57:21 Decision-Making and Lifelong Learning 57:22 - 01:04:51 Final Reflections and Outro

It was the last exit 16 years ago that hit him hard.

What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been.

In this episode we discuss his hard-earned lessons on happiness, why he started his fourth business now and walked away from running his VC firm.
 _____________________________________________________
00:00 - Introduction
01:33 - The impact of the 2008 exit and the dark decade
03:10 - Initial feelings and challenges post-exit
05:32 - Divorce and addiction struggles
07:51 - The sudden change in life without a business to run
09:55 - Coping mechanisms and poor investment decisions
11:57 - The importance of grounding oneself after a major life change
14:02 - Reflections on making poor decisions and facing addiction
16:10 - The importance of dealing with significant life events
18:08 - Advice to the younger self: taking time off and dealing with addictions
19:53 - The impact of personal struggles on family
21:54 - Strategies for being present and engaging with children
24:02 - The role of family in finding happiness
26:02 - Recognizing the importance of real friends and authentic relationships
28:20 - The danger of wealth changing social dynamics
30:25 - The importance of staying grounded and real
32:23 - Transition from VC firm back to entrepreneurship
34:20 - The creation of UP and its vision
36:19 - The importance of having a clear purpose and passion for work
38:21 - Changes in views on wealth and financial freedom
40:35 - The role of money in achieving happiness
42:22 - Learning to appreciate simple pleasures in life
44:12 - Finding happiness in nature and everyday moments
46:26 - Teaching kindness and empathy to children
48:29 - The role of nature in achieving a balanced and happy life
50:25 - The desire to leave a meaningful legacy
52:26 - The importance of helping others and making a positive impact
54:33 - Reflections on how to be remembered
56:29 - Parenting strategies and guiding children towards real values
58:28 - The importance of independence and real-world experiences for children
01:01:04 - Balancing drive and contentment in personal and professional life
01:03:26 - The journey to finding personal happiness
01:05:20 - Combining contentment with entrepreneurial drive
01:07:30 - Final thoughts on balancing life, work, and happiness

Today, he runs a VC firm called Tandem and has written a book titled The Factory for Good on turning your life into a force for positive impact. 

In this episode, we explore the emotional complexities of wealth and discuss why he envies those still in the rat race, how he earns his sleep, finds purpose and talks to his kids about wealth.

_____________________________________________________
00.00 Introduction 
01:57 The Post-Exit Emotional Journey: Pride, Excitement, and Unfulfillment 
07:03 Transitioning to Venture Capital: Purpose and Fulfillment 
13:59 Challenges and Lessons After Selling a Company: Insights for Entrepreneurs 
30:31 Purpose, Values, and Success: Building a Meaningful Post-Exit Life 
33:00 Legacy and Impact: Creating a Lasting Influence 
53:31 Finding Your Superpower: Leveraging Strengths for Post-Exit Success

CK Kim's website: https://www.changkim.me/ 

More about CK's sabbatical leave: https://www.linkedin.com/posts/changkim_on-sabbatical-activity-7195448168396861440-zcvW/?utm_medium=member_desktop&utm_source=share 

_____________________________________________________
00:00 Introduction 
00:50 The Journey of Starting and Selling Two Companies 
04:55 Transitioning from Founder to Employee 
09:15 Life After the Exit: Rest and Recovery 
23:00 Long-Term Thinking and Finding the Right Path 
29:15 The Importance of Soul Searching and Rest 
33:40 The Power of Conversations 
40:05 Finding Meaning and Purpose 
43:00 Managing Imposter Syndrome 
48:45 The Fulfillment of Parenthood 
51:30 Creating a Platform for Sharing Wisdom

But Preston wasn't there to experience it. 

While he regrets exiting too early, he acknowledges that the exit propelled him into an intense personal growth journey. 

In this episode, Preston shares how he learned to appreciate what he had, communicate more vulnerably and understand the compounding effect of experience, skills, and relationships. 

Connect with Preston: 
LinkedIn: https://www.linkedin.com/in/prestonr/

____________________________________________________
(00:00:00) Intro 
(00:01:11) Welcome 
(00:01:50) Reason behind starting Chubbies 
(00:02:13) Reasons for leaving Chubbies 
(00:03:52) Consequences of leaving the business 
(00:04:42) Contemplations on the decision to leave 
(00:05:24) Regret on leaving the business 
(00:06:16) The pursuit of greener pastures 
(00:07:14) Learning from the decision to leave 
(00:08:33) Journey back to the zone of genius 
(00:09:20) Overcoming burnout and healing 
(00:12:20) Facing personal and professional challenges 
(00:13:47) Realizations and personal growth 
(00:14:21) Finding out personal identity 
(00:17:41) Coming to terms with self worth 
(00:18:34) Working on personal development 
(00:21:13) Understanding the definition of success 
(00:23:14) New definition of success 
(00:25:09) Search for self-worth 
(00:26:09) Current definition of success 
(00:27:25) Professional journey and success 
(00:28:10) Reflections on personal life 
(00:29:14) Personal life and family 
(00:30:06) Juggling work and family life 
(00:30:21) Joy and personal life reflections 
(00:33:02) Work and self-identity 
(00:35:25) Progress since leaving previous company - Chubbies 
(00:40:01) Relationship with wife amid business challenges 
(00:44:16) Balancing dreams and practicality in business 
(00:47:32) Transition period after Chubbies and preparations for new business 
(00:48:45) How he wants to be remembered

Today, Gil runs a venture capital firm which adds value to consumer tech companies by bringing celebrities onboard. 

In this episode, we discuss overcoming a post-exit identity crisis, building a personal brand, dealing with celebrities and becoming an investor. 

Connect with Gil: 
Linkedin: https://www.linkedin.com/in/gileyal

____________________________________________________
(00:00:00) Intro 
(00:01:17) Welcome 
(00:09:33) The role and impact of Influence Marketing 
(00:14:41) The struggle and lessons of selling a company 
(00:16:55) Dealing with separation and moving on after selling 
(00:19:38) Retaining financial interest and future prospects 
(00:20:37) Reflections on past experiences as a founder and transition into an investor 
(00:24:02) Advice for someone selling their company 
(00:26:37) Building personal brand post-exit 
(00:28:25) Reflecting on mentorship and investment choices 
(00:30:06) Balancing relationship with personal life post-exit 
(00:32:46) The impact of investing on mentorship 
(00:35:06) The effect of an exit on family 
(00:37:33) Prospects for children becoming entrepreneurs 
(00:38:31) Future as an investor 
(00:39:10) Challenges in the investment industry
(00:39:33) The challenges of being an investor
(00:41:20) Personal risk in investments 
(00:43:24) Advice on angel investing 
(00:45:32) Joining a group and surrounding yourself with experts 
(00:46:17) What to do after an exit 
(00:48:02) Changing your lifestyle post-exit

Following the sale, Craig grew the business 30-fold and took the company global before leaving in 2019. He then found his calling in building Peggy.com, a secure marketplace for buying and selling investment-grade art. 

In this episode, Craig shares how and why he found his post-exit mission in making incredible art affordable to everyone. 

Discover more about Peggy: https://peggy.com/

____________________________________________________
(00:00:00) Intro 
(00:01:11) Welcome 
(00:03:03) Post-Business Life and Feelings 
(00:03:46) Sabbatical Experiences and Growth 
(00:06:12) Creativity and Business Associations 
(00:07:42) Brainstorming New Business Ideas 
(00:08:37) Development of New Business Idea 
(00:09:16) Understanding the Art Industry and Seeing Opportunities 
(00:13:16) Motivations behind Starting a Business 
(00:16:54) Desire for Social Impact in Business 
(00:18:08) Purpose-driven Business Endeavor 
(00:19:29) Reflections on Money and Wealth 
(00:20:35) Sharing Success with Loved Ones 
(00:21:51) Following Motivation for Creativity 
(00:22:18) Money as a Resource and Scarce Time 
(22:52) Self Identity and Growth Reflection 
(23:48) Imposter Syndrome in Entrepreneurs 
(24:04) Separating Personal Identity from Business 
(26:03) Investment and Detachment in Business 
(27:12) Rediscovering Self Identity after Exiting Business 
(27:58) Moral Acceptability of Pursuing Self-Interest in Business 
(29:19) Personal Growth and Self-Improvement Plans 
(30:15) Relationship with Spirituality 
(32:00) The Transition from Entrepreneur to Employee 
(34:07) Alternative Investment and Art 
(34:56) The Impact of Art on Society 
(36:38) The Role of Suffering in Personal and Business Success 
(41:33) The Importance of Pleasure and Satisfaction 
(43:51) Future Plans for Peggy and Disruption in the Art Industry 
(00:45:41) Definition of Canon and Role of Auction Houses 
(00:46:39) The Use of Blockchain for Technology 
(00:47:38) Future Plans and Legacy 
(00:49:02) Discussion on Mental Health and Childhood

Connect with Dave:
Website: https://www.davehersh.com/
Reignition - Book by Dave Hersh: https://www.amazon.com/Reignition-Transforming-Startups-Breakout-Winners/dp/1639090347 

_____________________________________________________
(00:00:00) Intro 
(00:01:21) Welcome 
(00:01:33) Life After Selling the Company 
(00:02:05) The Founding of Jive 
(00:04:24) Changing Trends in Digital Communication 
(00:05:14) The Challenges of Scaling Up 
(00:06:02) Life After Leaving the Company 
(00:08:16) Dealing with Identity Crisis 
(00:09:12) The Hoffman Process 
(00:10:46) The Art of Accomplishment 
(00:13:20) The Long Process of Reinvention 
(00:15:36) The Need for Inner Work and Transformation 
(00:16:37) Overcoming Entrepreneurial Struggles 
(00:18:01) Trying to Reconstruct Past Success 
(00:19:26) Finding Clarity and Direction 
(00:21:01) The Process of Transforming Identity 
(00:23:00) The Liminal Space Between Old and New Self
(00:24:43) The Wilderness and Benefits of Being a Ghost in Between Worlds 
(00:25:20) Transition from Jive to Andreessen Horowitz 
(00:33:30) The Decision to Leave Venture Capital 
(00:35:31) Acquiring Businesses and Understanding Their Core 
(00:38:15) The Art of Identifying and Peeling Away Non-Core Activities 
(00:42:30) The Transformative Power of Returning to Your Core 
(00:43:55) Bounce Back Post Acquisitions and Restructures 
(00:44:12) Experimentation for Growth & Financing 
(00:45:24) Transforming into Purpose-Driven, Disciplined, and Strong Culture Businesses 
(00:46:08) Building a business that matters 
(00:53:00) Personal definition of success 
(00:54:33) Choosing the right people to surround with 
(00:57:29) Reimagining the idea of a company 
(00:58:38) Personal transformation and rebuilding 
(01:03:28) The trend of the creator economy 
(01:04:52) Optimism for younger generations 
(01:05:58) A perfectly fulfilling life 
(01:06:32) Discussing happiness and joy 
(01:07:26) Rating personal fulfillment 
(01:08:33) Advice after selling a company 
(01:09:16) Importance of inner work 
(01:09:55) What keeps one up at night 
(01:10:19) Discussing personal divorce 
(01:11:33) How one wants to be remembered 
(01:12:11) Anticipation for upcoming book

In this episode, he shares this formula with us, delving into how to identify your true zone of competence, release control, and master the art of letting go.

_____________________________________________________

(00:00:00) Intro 
(00:01:25) Welcome 
(00:01:41) LinkedIn Profile of Mike 
(00:02:24) Discussing Mike's identity 
(00:03:18) Mike's experience after selling his business 
(00:07:35) Mike's experience on exiting business 
(00:10:10) Mike's perspective on initiating a startup 
(00:11:01) Being a part of a startup team 
(00:13:34) Traumatic experience of building a company 
(00:18:52) Missing the entrepreneurial experience 
(00:20:50) Discussions on Mike's new venture 
(00:21:25) Two types of approaches to problem-solving 
(00:24:03) Post-idea creation process 
(00:27:07) Role of passion and motivation in entrepreneurship 
(00:30:38) Trauma in starting a new venture
 (00:33:36) Defining success in present day
 (00:38:16) The journey from chasing status to chasing happiness 
(00:41:35) Balancing entrepreneurship with parenthood
 (00:42:22) Starting the M&A Process While Having a Newborn Baby 
(00:43:34) Balancing Work and Life and Aiming for a Healthy Business Structure
 (00:44:57) Striving for a Balanced Life while Building a Business 
(00:47:43) Implementing Business Plan While Being Parents of Young Children
 (00:49:31) Dealing With Wealth and Financial Success 
(00:51:57) Utilising Wealth and Managing it With Responsibility 
(00:53:37) Using Wealth to Accomplish Goals and Support Causes 
(00:54:44) Experiencing Economic Anxiety and Addressing Guilt
 (00:56:05) Being True to yourself, Leaving Things Better than Found, and Being a Good Human
 (00:57:47) Using Means to Empower Others and Improve the World 
(00:59:10) Integrity as a Core Value 
(01:00:27) Balancing Parenthood and Founding a Company
 (01:00:54) Working to Pay it Forward 
(01:01:04) Entrepreneur's Approach and Zone of Genius 
(01:01:55) Spirituality and its role 
(01:04:58) Advice for a business post-sale
 (01:08:01) The introspective work founders ought to do
 (01:09:13) Shifting from identifying as a founder to a larger role
 (01:14:05) The role of tech post-COVID 
(01:18:34) Level of fulfillment 
(01:20:09) Legacy and how to be remembered

Four years ago, he fully exited his business and now describes his life as post-economic. He realized he had a money addiction his entire life and took a radical step to address it—he avoids any money-making activities, focusing instead on activities that increase his energy. 

In this episode, we focus on how to know what we truly want and whether we have enough. 

Beyond The Finish Line: https://btfl.org/ 
Retired Founder Twitter: https://twitter.com/RetiredFounder

_____________________________________________________
(00:00:00) Intro 
(00:02:09) Reasoning behind anonymity 
(00:03:43) Business selling journey 
(00:06:15) Post-business selling life 
(00:08:06) Personal discovery and growth
 (00:09:50) The struggles in retirement 
(00:11:10) Unraveling the unhappiness 
(00:14:00) Breaking bad habits 
(00:17:35) Further self-discovery and improvement 
(00:18:56) Reflections on the pursuit of money 
(00:19:45) The concept of "enough" money
(00:20:28) The struggle with money addiction 
(00:21:08) Forming an anonymous support group 
(00:21:35) Description of 'Beyond the Finish Line' group 
(00:22:10) Dealing with loss of work structure after exit 
(00:25:04) Choosing to separate self from money making endeavors after exit 
(00:30:00) Emotional connections to the sold business and the importance of being needed 
(00:35:16) The quest for being useful and finding satisfaction 
(00:37:03) Setting up for inviting good things into life
 (00:38:59) Overcoming post-exit blues and the journey to self-enlightenment 
(00:40:41) The realization that happiness is not equal to money 
(00:41:43) The comfort zone and yearly expense 
(00:42:27) Discomfort and societal views on financial pursuit 
(00:47:07) Potential of finding a new purpose with economic upside
 (00:51:14) Balancing personal monetary gain with sustainable solutions
 (00:53:28) Personal hobbies and recreational activities that energize 
(00:57:59) The struggle with too much freedom 
(01:00:17) The process of energy management 
(01:01:57) The sense of purpose and fulfillment through contribution and growth
 (01:03:16) Art of Disappearing 
(01:04:15) Views on Legacy 
(01:05:06) Thoughts on Inheritance 
(01:07:03) Mental Health Discussion 
(01:08:11) Silent Retreats and Psychedelics Exploration
 (01:10:03) Vision of the Four False Gods 
(01:10:47) Wrap Up and Final Advice

Now, Laurent is channeling his expertise and refined taste into launching a wine company committed to delivering the world’s finest wines at fair prices. 

In this episode, we explore the art of building luxury brands, quality obsession, and treating business as an artistic endeavor. A deep and independent thinker, Laurent shares his life lessons with us in a beautifully vulnerable way.

_____________________________________________________

(00:00:00) Intro 
(00:01:18) Introduction and Greeting
 (00:01:30) About Laurent's Thought Process and Life Experiences
 (00:01:50) Journey of Building Tablet Hotels
 (00:02:20) Motivation Behind Starting Tablet Hotels
 (00:04:12) Importance of Convincing People in Business
 (00:07:15) Challenge of Funding 
(00:09:55) Growth and Business Model of Tablet Hotels
 (00:10:15) Difference in Business Approaches 
(00:11:04) Brief on LVMH & Bernard Arnaud 
(00:12:00) Methodology of Growing Businesses 
(00:14:07) Process of Shift to the Next Business Venture
 (00:16:18) Process of Looking Inward For Growth
 (00:19:09) Decision on Regaining Entrepreneurial venture
 (00:20:46) Intersection of Art and Commerce 
(00:22:57) Art, Wine, and Commerce 
(00:23:24) Structure of the Wine Industry 
(00:24:18) The art of wine making 
(00:26:04) The drawback of removing alcohol from wine
 (00:26:26) Scouting wine artisans globally 
(00:27:58) Mission to help people discover good wine 
(00:31:30) Learning about the complexity of wine distribution in the US 
(00:34:38) Money as a means of freedom 
(00:37:14) Engaging with life through entrepreneurship 
(00:40:37) On becoming an angel investor
 (00:42:51) Self-growth and patience 
(00:45:33) Creating something desirable
 (00:46:29) Fulfillment and Happiness 
(00:49:45) Fulfillment as Satisfaction 
(00:53:30) Personal Growth and Intent 
(00:57:39) About New Business MV Wine
 (00:59:41) Engaging with Life When Awake 
(01:02:06) Dealing with Unfiltered Challenges 
(01:05:32) Creating a Vehicle to Express Creativity
 (01:07:31) Perception of Selfishness 
(01:08:07) Conclusion and Gratitude

A deep and original thinker, he chose to confront his post-exit mental health issues head on. 

In this episode, Keith openly shares his insights, therapy takeaways and how he found his latest mission in empowering creators with his innovative AI tools.

_____________________________________________________

00:00:00: Intro 
00:01:27: Welcome 
00:01:50: Discussing Keith's life-changing moment in 
00:02:15: Discussing Keith's background 
00:03:28: The impact of wealth on Keith's mindset 
00:06:09: Developing empathy and changing mindset about wealth 
00:06:44: Balancing business and parenthood 
00:09:26: Learning to share wealth and outcomes 
00:10:17: Adjusting equity in business partnerships 
00:12:12: Motivation behind starting the first company 
00:13:24: Views on wealth and societal impact 
00:14:27: Personal growth and the importance of self-evaluation
 00:16:47: Experience as a single parent while building a business 
00:19:55: Children's involvement in the business 
00:20:54: Insights from business successes and failures
00:22:08: Reflection on experiences as a repeat founder 
00:24:44: Importance of mental health before and after an exit 
00:26:11: The therapeutic journey and self-discovery 
00:29:42: Spirituality and mental health in personal development 
00:32:10: Addressing mental health stigma, especially among entrepreneurs 
00:34:23: Transitioning from ad tech to fintech, and to AI 
00:36:14: Building impactful socio-tech solutions 
00:39:58: Launching Meforyou.ai and the problem it aims to solve 
00:42:07: Addressing the "loneliness epidemic" through AI 
00:42:47: Discussing Behavioral Changes Toward Media Consumption 
00:43:23: Synthetic relationships for the disconnected and lonely 
00:43:57: How AI Personas can potentially be used for Education 
00:45:15: Potential Use in Entrepreneurship and Mentorship 
00:46:10: Evolution of Company's Features and Starting Point 
00:47:21: The Future Use Cases for AI Personas 
00:49:04: Personal Impact and Civic Mindedness 
00:50:16: Personal Goals and Successful Outcome
 00:53:04: Transition after Selling Company, Imposter Syndrome 
00:56:02: Recognizing the Imposter Syndrome in Others, Importance of Spreading Opportunities 
01:00:02: Systemic Biases in Society 
01:01:03: Personal Therapy and Self-Sabotage 
01:02:47: Discussing personal life and struggles 
01:03:07: Intentions and personal reflections 
01:03:37: Choosing the people to have around 
01:04:52: Working with a team and personal dynamics 
01:06:56: Dealing with breakups and personal life 
01:07:10: Dating apps and searching for a partner
 01:09:13: Telling a story, finding a fit and blending energies
 01:09:21: Sense of purpose and believes 
01:10:38: Psychedelics and taking new paths 
01:11:06: Level of fulfillment
 01:13:14: Raising children and developing relationships 
01:16:00: Importance of hobbies and reshaping identity 
01:18:16: Hobby of one wheeling 
01:19:20: Most important lessons learned since the first life changing exit 
01:20:37: Impactful lessons from children 
01:22:47: Reflections on parenthood and self-improvement 
01:23:06: Desire to make a societal impact 
01:24:15: Vision for the future and overcoming age 
01:25:17: Closing remarks and farewell

_____________________________________________________

Timestamps: 00:00:00: Intro 
00:01:16: Welcome 
00:01:26: The sale of Support Ninja 
00:02:42: The experience of selling a company 
00:03:08: Lessons learned from selling the company
 00:09:48: The start of Operator Equity 
00:10:10: How Operator Equity works 
00:12:01: Explanation of EOS (Entrepreneur Operating System) 
00:14:22: Experiences with EOS and why it was chosen 
00:17:01: Ambitions for Operator Equity
 00:17:15: Why Operator Equity was started
 00:18:11: Personal love for inception and growth of a company 
00:19:27: Investment in mature companies
 00:20:33: Managing the creative impulse with mature companies 
00:21:11: Beginning of Operator Equity journey 
00:21:26: Looking ahead: The future of Operator Equity 
00:22:15: Reflections on the impact of ego in business 
00:23:04: The notion of fleeting success and the value of the journey 
00:23:43: The struggle of self-identity post exit 
00:26:13: The evolution of thoughts about money and wealth 
00:28:24: The challenges and fears related to sudden wealth 
00:31:06: Caution around extending financial security to others 
00:31:45: Uncertainty in defining personal success after exit 
00:33:22: The impact of financial success on personal relationship 
00:35:45: Thoughts on sense of purpose post business exit 
00:37:55: Avoiding guilt through conscious actions in business 
00:39:56: Managing imposter syndrome and motivation 
00:43:02: Expectations and understanding of success from parents' perspective
 00:43:55: Discussion about stepping down and operator equity 
00:44:23: Thoughts on raising future children and entrepreneurship 
00:45:35: Talks on operator equity and investments 
00:47:24: Inquiry over work-life balance 
00:48:42: Question on personal legacy 
00:49:50: Conclusion and best wishes for future projects

_____________________________________________________

Timestamps: 00:00:00: Intro 
00:01:10: Welcome 
00:01:19: Discussion about the sale of ILab's operation system 
00:01:37: Discussion about the treatment of staff post-sale 00:01:46: Discussion about the bootstrapping process 
00:01:56: Discussion about life post-exit 
00:02:09: Reflection on change post-exit 
00:03:01: Discussion about the financial aspects post-exit 
00:03:12: Discussion about managing time after selling the business 
00:03:57: Discussion about how the exit was structured 
00:05:10: Discussion about joining the buyer 
00:05:34: Reflection on being an employee post-exit
 00:06:28: Discussion about running operations for iLabs 
00:07:10: Discussion about being a creative person 
00:07:39: Discussion about motivations for starting a new business 
00:09:14: Reflection on the entrepreneurial journey 
00:09:19: Discussion about the creation of the Longangle community 
00:10:31: Discussion about the growth of the Longangle community
 00:11:01: Reflection on what Longangle gives to the founder 
00:13:00: Discussion on angel investing 
00:18:33: Reflection on angel investing as a financial strategy 
00:19:46: Reflection on time spent on angel investing 
00:20:09: The Balance of Time: Mentoring, Deal Flow Sourcing, and Personal Life
 00:20:29: After Exit Stage: Opportunities and Challenges 
00:21:46: The Unexpected Time Investment in Startups 
00:22:04: The Impact and Limitations of Being an Angel Investor 
00:22:25: The Long Game of Angel Investing and the Consequences of Fundraising
 00:23:16: Investment Outside of Angel Investing 
00:24:37: Diversification of Portfolio: Real Estate and Broad-based Indices 
00:25:11: The Desire for Simplification in Investments 
00:28:19: Community Involvement: Engaging in the DC Tech Scene 
00:28:58: Entrepreneurship Education for the Younger Generation 
00:29:20: The Concept of "Ikigai": Defining Purpose and Intention
 00:30:48: Aspirations for the Future: The Drive for Building 
00:33:04: The Influence of Wealth on Time Allocation 
00:34:17: Reflective and Introspective Retreats 
00:36:36: The Impact and Responsibility of Wealth 
00:38:17: Regrets and Reflections on Selling a Business 
00:39:37: Post-Exit Mental Health: The Need for Therapy
 00:41:31: Consequences of quitting and firing 
00:42:32: Thoughts on Spirituality and Culture 
00:44:06: Personal Growth Strategy 
00:45:16: Advice for business sellers 
00:49:36: Importance of Health 
00:50:35: How fulfilled are you? 
00:52:43: Surrounding oneself with the right people 
00:55:26: Recreational activities and building networks 
00:55:57: Legacy and How to be remembered

_____________________________________________________

 Timestamps: 00:00:00: Intro 
00:01:18: Welcome 
00:01:49: Ari's previous dermatology business 
00:02:34: Partnership and business dynamics with his wife 
00:10:37: Selling the business
 00:13:56: Post-exit reflections 
00:19:05: Mental health
 00:21:30: Decision to seek help for mental health 
00:21:44: Overcoming Depression and Anxiety 
00:24:01: Discovering Natural Alternatives to Conventional Medications 
00:24:47: Utilising Financial Freedom for Personal Growth 
00:26:26: Facing the Second Mountain - Shifting the Focus from Personal to Community Centric 
00:27:13: Launch of the new company, Roar 
00:28:11: The Effect of Psychedelics 
00:31:30: Pioneering Psychedelics in the Startup Space 
00:32:08: Exited Founders and Psychedelics 
00:32:28: Taking a Leap into Psychedelics 
00:33:10: Recommended Psychedelic for Beginners 
00:36:11: Applying Neuroplasticity Through Psychedelic Medicines 
00:38:31: Breaking Habits with Neuroplasticity 
00:39:01: Ketamine Assisted Therapy and Ego Dissolution 
00:40:34: Perspective on Psychedelics
 00:41:35: Comparing Ketamine to Other Psychedelics 
00:42:50: Concerns About Psychedelic Experiences 
00:44:14: Discovering Psychedelic Medicine Through Media 
00:45:37: Abuse of Psychedelic Drugs and the War on Drugs 
00:49:52: The Impact of Politics and Divisiveness on Mental Health 
00:51:26: The Risks and Stigmas Around Psychedelic Medicines 
00:53:24: Exploring The Spiritual World with Psychedelic Medicines 
00:56:58: Realizing Personal Potential and Striving for Self-Improvement 
00:58:07: Re-evaluating the Definition of Success 
00:59:10: Personal Success Definition
 01:00:04: Business Success and Liquidity Event 
01:01:22: Psychedelic Medicine and Personal Growth 
01:02:07: New Business Announcement - Betterness 
01:03:03: Current Medications and Supplements 
01:07:06: Dealing with ADHD 
01:13:46: Choosing People to Spend Time With
 01:16:28: A Perfectly Fulfilling Life for Ari 
01:18:12: Rating Personal Fulfilment 
01:20:30: Perception of Wealth & Fulfillment 
01:26:41: Perspective on Global Issues 
01:28:39: Joy Derived from Family, God and Spirituality 
01:32:13: Learning after Selling the Company 
01:37:17: Striving for perfection and the role of luck in success 
01:37:49: Importance of sharing entrepreneurial stories and overcoming challenges 
01:38:14: Gratitude and appreciation for the podcast and its host, Anastasia 
01:38:58: Concluding the conversation and future meeting plans

_____________________________________________________

 Timestamps: 00:00:00: Intro 
00:01:24: Welcome 
00:01:46: Sharing Personal Experiences and Lessons Learned 
00:03:34: Recalling the Business Exit 
00:04:10: Dealing with Post-Exit Struggles and Imposter Syndrome 
00:09:09: Losing Identity after Selling the Business 
00:10:25: Discussing New Opportunities and Future Outlook 
00:12:13: The Impact of Selling on Creativity and Control 
00:13:41: Reflecting on Regrets and Decisions 
00:17:41: Returning to Self-Identity and Recovery 
20:27: Discussing insecurities 
00:20:49: Starting therapy 
00:23:25: Experience with psychedelic drugs 
00:28:57: Confronting alcoholism
 00:33:03: Discussing life post exit
 00:35:02: Sharing experiences on social networks 
00:36:40: Discussing Ikigai concept 
00:37:24: Using five love languages
 00:39:12: Personal Insights and Relationships 
00:40:01: The Influence of Family 
00:40:18: The Significance of Goal Setting 
00:42:11: Valuable Business Frameworks 
00:43:31: Thoughts on Masking Authenticity 
00:44:39: Level of Fulfillment 
00:47:49: Important Business Lessons 
00:48:59: Dealing with Depression and Staying Fulfilled 
00:51:00: Motivations for Starting Businesses
 00:52:42: Learnings from the Beverage Industry 
00:55:01: Journey to Sparkling Water Business 
00:55:13: Perspective on Wealth and Money 
00:56:50: Future Personal Goals 
57:06: Discussing family and being remembered 
57:25: Wrapping up the interview 
57:31: Therapy Thursday discussion 
57:39: Appreciation for the podcast platform 
57:58: Discussing LinkedIn posts 
58:12: Talk of potential extended interview 
58:25: Plans for future chats 
58:35: Final Thanks and End of Conversation

_____________________________________________________ 

Timestamps: 00:00:00: Intro 
00:01:07: Nick's life post business sale 
00:01:18: The impact of money on happiness 
00:01:27: Future plans for Nick
 00:01:45: Thoughts on Angel investing 
00:02:06: Lessons learned from business 
00:02:53: How Nick wants to be remembered 
00:03:05: Reflecting on the moment of selling the company 
00:04:07: Personal crisis post-sale 
00:05:13: Shift in idea of purpose after business sale 
00:06:47: Self-discovery and ideation post-sale 
00:07:44: Beginning of angel investing and new approach to stress 
00:08:42: Motivations for continuing in business and advisory roles
 00:09:14: Continuing desire to succeed and win 
00:10:33: Discussion on the motivation for starting the first business 
00:12:17: Exercise for financial freedom 
00:13:36: Reflection on accomplishment of achieving financial goal 
00:16:02: Thoughts on selling the company 
00:16:35: Recollections of relief post-sale 
00:18:12: Comparing past business motivation with current Trumpet business 
00:19:10: Adjusting to new founder's financial objectives 
00:20:07: Current motivation - learning and challenging self 
00:20:41: Identity crisis post-business sale 
00:21:56: Adjusting to new identity as a "startup guy". 
00:22:36: Discussion about identity and starting of Podcast 
00:23:13: Benefits of raising money from angel investors for early-stage businesses 
00:24:06: Different formats for Podcast and its live nature 
00:24:43: Purpose of starting the Podcast - Making angel investing less secretive
 00:25:13: Success rate of the Podcast 
00:26:02: Networking and forming friendships via the Podcast 
00:27:32: Relation of Podcast and personal purpose post-business exit 
00:28:57: Future plans post-trumpet days 
00:29:24: Current Fulfillment rating 
00:31:01: Changes in views towards money and wealth after exit 
00:33:16: Importance of taking time for joy and presence 
00:34:02: Discovering joy in walking 
00:35:15: Health restoration post-exit during Covid
00:36:38: Thoughts on imposter syndrome 
00:39:10: Candidness about making mistakes and continuous learning 
00:41:39: Mental health struggle during 'my night' and post-exit realization 
00:43:40: Discussions on Purpose and Joy 
00:44:51: Thoughts on Growing Up and Impacting the Community 
00:46:56: Experience in Angel Investing 
00:51:04: Current Position in Angel Investing 
00:52:48: Thoughts on Why Founders don't Ask for Help 
00:55:10: Reason Why Founders Become Angel Investors 
00:59:44: Effect of Exit on Relationships with Friends and Family 
01:01:06: Parents' Influence on Becoming an Entrepreneur 
01:02:25: Choosing Who to Surround with 
01:05:09: Friendship and energy 
01:06:10: Thoughts on spirituality 
01:09:07: Spirituality and mysticism separation 
01:09:33: Contribution and purpose 
01:10:42: Resolving the self-interest paradox 
01:11:51: Closing remarks

_____________________________________________________

 Timestamps: 
00:00:00: Intro 
00:01:12: Welcome 
00:01:15: Deep dive into money happiness 
00:01:31: Exploring the concept of fulfillment 
00:03:17: Discussion on the merits of angel investing 
00:03:30: Sharing important lessons from a big exit 
00:03:59: Advice post selling your company 
00:04:37: Importance of introspection and how to stimulate it 
00:05:20: Anastasia's method for choosing the people she surrounds herself with 
00:06:03: An insight into Anastasia's first business venture and exit 
00:07:37: Discussing life changing exits 
00:09:57: Identifying the role of competitiveness and love for the game 
00:12:01: A discussion on business growth and potential plans for future businesses 
00:13:36: Reflecting on Anastasia's childhood and how it influenced her entrepreneurial journey 
00:16:06: Anastasia's family background and her deviation from traditional career paths 
00:19:39: Investigating patterns between successful entrepreneurs and their backgrounds 
00:20:01: Different types of entrepreneurs and Anastasia classifying herself 
00:21:15: The effect of Anastasia's first job on her entrepreneurial drive. 
00:22:09: Overcoming Challenges
 00:22:47: The Importance of Having a Purpose 
00:23:17: Post-Exit Reflections 
00:24:15: Post-Exit Depression 
00:25:13: Realising Money Isn't Everything
 00:26:15: Life and Death Situations 
00:27:15: Importance of Building Companies with Amazing People
 00:29:18: The Excitement of Seeing a Company Grow 
00:33:44: Fulfillment from Impacting Lives
 00:34:30: Achieving Success By Helping Others
 00:37:33: Philanthropy Projects
 00:41:13: Valuing Both Global and Individual Impacts
 00:41:18: Personal Life and Hobbies
 00:42:10: Current Daily Routine 
00:42:48: Personal Prioritizations 
00:43:38: Discussion on marketplace and venture studio 
00:44:30: Discussion on Company Builders 
00:45:14: Discussion on "Die with Zero" and living life based on experiences
 00:46:25: Perspective on building businesses 
00:47:42: Discussing the regret minimization framework 
00:48:58: Discussion on societal treadmill and introspective questions 
00:50:47: Perspective on being an entrepreneur 
00:51:25: Events that shaped the speaker
 00:53:12: Closing the interview

LinkedIn Boris: https://www.linkedin.com/in/borisberenberg/

Blog Boris: https://www.nothingeasyaboutthis.com/i-regret-selling-my-startup/

_____________________________________________________

 TIME STAMPS: 
00:00:00 Intro 
00:01:00: Beginning and Introduction 
00:03:36: Discussing the Financial Side of Selling a Company 
00:04:55: Talking About Financial Expectations and Reality After Selling a Company
 00:07:33: Concept of "Dragon Mode" After Selling a Company 
00:10:08: Discussing Reaction and Regrets After Selling the Company 
00:13:25: Lessons Learnt and What Would Be Done Differently 
00:16:03: Understanding Personal Values in the Context of Selling the Company 
00:19:58: Mental Health Consequences for Founders Post-Sale 
00:20:46: Looking Back - Starting the Business. 
00:22:10: Effective team dynamics 
00:22:54: Reaching a career apex at a young age 
00:23:37: Starting on their own and consulting 
00:24:24: Balancing job security with business growth 
00:25:20: Shift in customer support ideologies 
00:26:45: The motivations behind founding a company 
00:27:21: The struggle with job autonomy
 00:28:09: Working in an environment with almost complete autonomy 
00:29:14: Perspectives on work-life balance and defining 'work' 
00:31:26: Losing identity after selling the business 
00:31:44: Contemplating next steps 
00:34:01: Challenges of life as a digital nomad
 00:36:33: Considerations on personal satisfaction vs financial security 
00:41:11: Finding a happy place in specific environments. 
00:42:15: The importance of networking and exploring future plans 
00:44:21: Personal relationships and their effects post-exit 
00:46:06: The benefits of the sale and finding a community 
00:47:35: The loneliness pre-sale and finding community 
00:48:24: Building acquaintanceships and friendships in new communities 
00:49:47: Channeling dissatisfaction into motivation 
00:50:46: Rating personal fulfillment 
00:51:24: Searching for a sense of purpose 
00:54:13: Discussing the difference in post-exit crisis for parents and non-parents 
00:56:03: Desiring simple remembrance as a good family member 
00:56:33: Aspiring to create a 'work playground' 
00:57:37: Looking forward to future businesses and potential failures.

Aaron and Anastasia delve deep into the concept of entrepreneurship being akin to longevity and transition. They unfold the compelling insights about the joys, struggles, and beauty of entrepreneurship, viewed essentially as an infinite game where the primary motivation lies in the joy of creation itself. Tune in and prepare to see entrepreneurship through an entirely new lens.

_____________________________________________________

Timestamps: 
00:00:00: Intro 
00:01:05: Welcome 
00:01:18: Aaron's post exit journey & lessons learned 
00:02:30: Challenges faced in previous startup ventures 
00:03:24: Discussing the concept of deals 
00:03:33: Reflecting on personal motivations and growth mindset 
00:06:02: Importance of customer satisfaction in business 
00:07:33: Reflecting on personal growth and motivations (continued) 
00:09:00: Struggles of identity crisis post exit 
00:09:22: Transition to another startup venture 
00:11:09: Reflections on successful exits and their impacts
 00:13:04: Personal feelings post-successful exit 
00:13:53: Strategies to handle identity crisis 
00:16:26: Being obsessive about new things and learning 
00:18:00: Allowing deep immersion in interests 
00:18:48: Exploration of personal and business identity 
00:19:00: Supporting growth in team members and building strong culture 
00:21:21: Maintaining vision and focus in business 
00:21:49: Discussing alignment with family members. 
00:22:10: Family influence on entrepreneurship 
00:23:05: Wife's support and influence 
00:23:49: Lessons from parents 
00:25:23: Did parent's expect entrepreneurship? 
00:26:33: Entrepreneurship as a form of art 
00:28:05: Channeling creativity in entrepreneurship 
00:30:25: Advantages of sharing accomplishments 
00:33:41: Embracing public storytelling 
00:36:22: Why transition to VC? 
00:40:28: Challenges with VC 
00:40:58: Preference for Team Building 
00:41:20: Challenges of being an angel investor 
00:42:14: Balancing personal time with investment opportunities 
00:42:34: Managing pressures and setting expectations 
00:44:11: Overcoming an identity crisis through angel investing 
00:46:18: Relationship with financial freedom 
00:48:32: The paradox of entrepreneurship and financial focus 
00:49:17: Wealth management strategies
 00:51:45: Grappling with fulfillment and ambition
 00:56:56: Choosing personal relationships intentionally 
00:59:27: Overcoming the trauma of past stressful experiences in business 
01:01:02: Building Better Teams 
01:01:55: Overcoming Business Struggles 
01:02:25: Balancing Responsibilities
 01:03:46: Maintaining Health During Stressful Times 
01:05:29: Increasing Ambition to Reduce Stress 
01:09:35: Envisioning a Bright Future with Technology
 01:12:01: The Importance of Post-Exit Healing 
01:14:55: Sustaining a Healthy Day-to-Day Routine 
01:16:38: The Struggle of Rest and Transition 
01:19:14: The Challenges of Starting New Ventures After Exits
 01:19:50: Preparing For Family Life. 
01:20:26: Work-life balance discussion 
01:21:45: Next big project criteria 
01:24:52: The importance of product building over business model 
01:28:35: Expectations for future success 
01:29:01: How to be remembered

_____________________________________________________

Timestamps: 
00:00:00: Intro 
00:01:13: Welcome 
00:01:21: Discussing important lessons from business experiences 
00:02:05: The correlation between happiness and money 
00:02:39: Discussing worries and concerns 
00:03:43: Things that bring joy in life 
00:04:31: Self-definition and uniqueness 
00:05:32: Future plans and goals 
00:06:11: Discussing sense of purpose 
00:06:48: Reflecting on personal legacy
 00:07:16: Recognition of achievements and experiences
 00:08:25: Source of motivation for impact 
00:09:31: Importance of striving for positive impact 
00:09:56: Discussing the morality of earning whilst serving others 
00:10:52: Reflections on childhood and parents' expectations 
00:12:23: Connection between entrepreneurship and mental health issues 
00:15:37: Addressing mental health issues post-business sale 
00:18:01: Relationship between spirituality and mental health 
00:19:37: Personal insights into life purpose 
00:22:25: Aspects of building personal relationships 
00:24:24: Reflection on the role of luck in business and success 
00:26:27: Influence of Success on Personal Attributes 
00:27:37: Lessons of humility on the Entrepreneur journey 
00:30:08: Dealing with guilt related to success 
00:30:42: Discussing Impostor Syndrome 
00:34:14: Dealing with failure and feelings of responsibility 
00:34:47: Regrets related to past business decisions 
00:36:33: Learning from business exits and realigning ambitions
 00:38:12: Understanding of wealth and its impacts
 00:40:29: Effects of business success on personal relationships 
00:41:26: Defining personal success and failure 
00:43:23: Reflections on undertaking business ventures 
00:45:35: Initiation of the business, deep 
00:47:53: Evolution of Business ideas and the birth of everpage.com 
50:42: Discussion on increasing anxiety post-pandemic 
51:06: Introduction of the "deep" app 
51:32: Pivot towards mental health and meaningful connections
 52:01: Discussion on kindred spirits 
53:14: What activities are meaningful in speaker's personal life 
54:23: Discussion on compassion, selfishness, and human connection 
55:33: Link between hurt and transactional relationships 
56:06: Steps towards becoming compassionate 
57:01: Philosophical insight on selfishness and fulfillment 
58:09: Thoughts on the concept of self, the illusion of independence
 59:02: Speaker's mission on this planet.

_____________________________________________________

Timestamps: 
00:01:00: The early journey into business and entrepreneurship 
00:01:22: Entering the cannabis industry 
00:01:56: Decision to avoid traditional nine-to-five job 
00:02:44: Becoming CEO at age 
00:03:26: The drive to solve problems in the industry 
00:04:19: Change in motivation after business exit 
00:06:12: Shifting from a fear-driven approach to a passion-driven one 
00:08:20: Considering other industries and opportunities 
00:10:51: Decision to sell first business and focus on another 
00:11:25: Feeling after selling first business 
00:14:34: Shifting perspective on money and success 
00:16:15: Parents' influence on entrepreneurship journey 
00:17:26: Starting a business with father 
00:19:24: Challenge and benefit of working with a family member in business 
00:21:01: Decision to go into business with father and learning through the process 
00:22:38: Growing up in a business-oriented family 
00:23:21: Impact of business partnership on personal relationships 
00:24:58: Parents' reaction to business partnership 
00:25:33: Impact of financial freedom on happiness 
00:28:14: Experience of travel and luxury after financial security 
00:29:11: Reflection on the journey of building and selling a business 
00:31:35: Learning lessons from the entrepreneurial cycle 
00:35:21: Experience and benefits of globetrotting 
00:43:39: The role of therapy in personal growth 
00:44:36: Lessons from a Life Coach 
00:57:18: Transitioning from Entrepreneur to Family Man 
01:02:57: Preparing for Parenthood 
01:03:39: How Brett Wants to be Remembered 
01:05:23: Entrepreneurship as Freedom 
01:06:13: Discussing personal freedoms and lifestyle 
01:07:35: Reflecting on retirement and the necessity of growth 
01:08:22: The role of financial success in personal growth and risk-taking 
01:09:41: Investment philosophy and financial strategy 
01:11:39: Closing the discussion and expressing gratitude

_____________________________________________________

 TIME STAMPS: 
00:00:00: Intro 
00:01:12: Background 
00:01:20: Starting the First Business, Fanbyte 
00:02:01: Fanbyte's Growth and Success 
00:03:15: The Rise of Influencer Marketing and Formation of Fanbyte 
00:03:51: Motivation Behind Starting Fanbyte 
00:04:33: Reflection on Entrepreneurial Journey 
00:06:09: After Selling the Business 
00:10:07: Reflection on Selling the Business and Significance 
00:12:23: Post-Business Activities 
00:17:00: Planning for the Future and Next Business Adventure 
00:19:36: Motivation for Next Business 
00:21:16: Reflection on Success and Luck 
00:22:49: School days and meeting intelligent peers 
00:23:43: Starting Entrepreneur Express 
00:24:19: Significance driving ambitions 
00:24:42: Thoughts on future business ventures 
00:25:08: Partnership dynamics at Fanbite 
00:28:02: Zones of genius 
00:30:22: Different mindsets of business founders 
00:30:41: Post-exit emotional stages 
00:33:12: Money meaning: ownership of time and optionality 
00:36:35: Abundance mindset and its impacts 
00:38:24: Changing relationships post-exit 
00:39:26: Money's role in shaping social circles 
00:41:45: Intentionally creating a circle with like-minded individuals 
00:43:03: Deciding the type of conversations and people to be around 
00:44:24: Managing money and portfolio strategy
 00:45:39: Mental struggle of adjusting to wealth 
00:51:11: Reconsidering the motivations for angel investing 
00:57:03: Power of manifesting and visualizing your goals 
01:03:06: The importance of serving others and spirituality 
01:06:27: Motivation and community building 
01:08:00: Life, Fitness and Health 
01:08:47: Regrets, Challenges and Aims 
01:13:33: Building a personal brand 
01:18:00: Choosing the right Platform 
01:19:19: Non-obvious ways to monetize a personal brand 
01:20:41: Legacy and Remembrance

In this episode, he shares how these insights now direct and drive his post-exit journey. He also offers actionable advice for you and me to live a more meaningful life.

_____________________________________________________

00:00:00 Intro 
00:01:03: Introduction 
00:04:04: Personal journey into Philosophy and Spirituality 
00:08:29: Career beginning in Real Estate Development 
00:12:32: Importance of maintaining discipline 
00:16:02: Transition from selfish to selfless 
00:19:57: Applying Vedantic principles to business and personal life
00:21:09: Leaving the Oligarch and Starting Own Property Business 
00:23:05: Desire to Teach Philosophy 
00:24:46: Naming of Family Office - Impact Assets 
00:26:30: Finding Balance in Desire for Business and Self-Actualisation 
00:27:52: Conflict Between Desire for Wealth and Spirituality
00:29:50: Concept of Managing Desires Over Wealth Management
00:31:21: The Case Study of Post-Exit Entrepreneurship
00:34:31: Understanding True Nature from an Entrepreneur Perspective
00:36:20: Desire for Control vs Spiritual Growth
00:38:57: The Role of Agitation in Sparking Bliss
00:39:56: Stages of Spiritual Development 
00:40:08: Levels of Spiritual Growth 
00:44:07: Building a Philosophy-focused Business 
00:46:52: Impact Investing 
00:50:20: Principles of Self Discovery 
00:52:39: Process of Having a Charitable Disposition 
00:54:25: Developing Intellectual Capacity for Control 
00:56:10: Reading Philosophy for Self Development 
00:59:33: Post Exit - Finding a Purpose 
01:00:10: The significance of action and reaction 
01:01:18: Discussion about the book "Die with Zero" 
01:02:10: Changing mindset from scarcity to abundance
 01:04:43: Incorporating philosophy into daily life
 01:06:15: Managing one's energy and giving within capacity 
01:09:33: Moving from selfish to unselfish 
01:12:47: Concept of meditation and achieving a still mind 
01:14:40: Thoughts on silent retreats and frustration of the mind 
01:15:35: Insights on different forms of yoga and pathways of learning 
01:17:57: Concluding thoughts

 👤 LinkedIn: https://www.linkedin.com/in/davidjonathangoldberg?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app 

🖥️ Founders Pledge: https://www.founderspledge.com/ 

_____________________________________________________

 Timestamps: 
00:01:08: The Purpose of Life and Time
 00:03:29: Drive and Work Ethic 
00:03:42: David's thoughts on Identity 
00:05:16: Secrets to a Successful Romantic Relationship 
00:06:00: What keeps David up at night 
00:07:56: Waking up Motivation 
00:08:30: How David wants to be Remembered 
00:08:44: Parent's Expectations 
00:10:02: Value of Formal Education and Start of Career 
00:13:36: David's First Business 
00:17:15: Developing Communication Skills 
00:18:20: The moment of Business Exit 
00:19:44: Motivation for the First Business 
00:20:10: Changes after Business Selling 
00:20:40: Upbringing and "winning the life lottery" 
00:21:31: Decision to do more than amass wealth 
00:22:28: Challenges and obstacles in philanthropy efforts 
00:24:07: Journey to discover true purpose 
00:24:38: Process and experience of self-growth 
00:26:26: Learning to think critically through formal education 
00:30:03: Undergoing the cultural shift of studying abroad 
00:32:05: Founders Forum group and understanding real poverty 
00:33:22: Redefining success after selling first business 
00:35:57: Encountering true poverty in Southeast Asia 
00:37:09: Using resources effectively for maximum impact 
00:37:49: The problem of "poverty tourism" 
00:39:09: How compassion plays a role in business success 
00:40:31: Introduction to Founders Forum and efforts to help social entrepreneurs 
00:41:04: Reasons why the initial idea didn't work. 
00:42:08: Evaluating the potential of startups
 00:42:27: The challenge of execution in social businesses 
00:43:06: Pivoting to support commercial entrepreneurs 
00:45:10: Founders Pledge 
00:47:23: The relationship with Founders Forum 
00:50:31: Aim to give effectively in Founders Pledge 
00:52:06: Resolving the problem of global donations 
00:55:02: Funding model of Founders Pledge 
00:56:56: The reality of Donor Advised Funds 
01:00:06: The challenge of raising funds annually 
01:02:20: Focus on impact in Founders Pledge 
01:03:33: Present commitments and funds injected in Founders Pledge. 
01:04:29: Scaling up 01:05:32: Mental health as a neglected area 
01:06:17: Introduction of non-profit working on mental health treatment in Africa 
01:07:35: Effects on post-exit journey of founders who pledged 
01:08:02: Role of philanthropy after exit 
01:11:36: Introduction to Founders Pledge 
01:15:02: The spiritual journey through Founders Pledge
 01:15:43: Introduction to Pledge Ventures 
01:18:02: Rules and initial fundraising for Pledge Ventures 
01:20:53: Commencement of investment through Pledge Ventures 
01:25:05: Introduction to the Foundry program 
01:25:54: Bespoke research programs for larger sums of yearly philanthropy. 
01:26:03: The Order of Giving and the Importance of Knowledge 
01:26:41: The Foundry Program 
01:27:26: Partners, not Clients 
01:28:07: Improving The Efficiency of Giving
 01:29:19: Transparency in Philanthropy 
01:30:00: Aligned Incentives with Members and Issues with Charities 
01:31:03: The Importance of Community in Philanthropy
 01:32:04: Future Impact and Growth of the Organization 
01:32:46: Efficiency and Control in Giving
 01:33:18: Pledges and Donations: Freedom of Choice
 01:34:03: The Organization’s Differentiating Factors 
01:35:11: Final Words

Timestamps 
00:00:37: Introduction of Michael, Founder of Tiger21

00:01:53: Discussion on investors

00:02:05: Challenges of investing

00:02:39: Handling Success and Entrepreneurship

00:04:17: Discussion on Turning into an Investor after Being an Entrepreneur

00:06:44: Setting realistic passive returns

00:18:49: Discussion on Family Offices

00:23:49: Michael's personal motivations and the foundations of his success

00:24:55: Michael's ambition and challenges in the early years

00:27:37: Michael's personal experience of hearing loss and its impact on his life

00:28:53: Reflection on the role of luck in building businesses

00:29:04: Discussing the Role of Luck in Success

00:32:46: Overcoming Responsibility and Trauma After Business Success

00:34:46: Navigating Early Success and Future Ventures

00:39:46: Balancing Entrepreneurship and Introspection

00:43:59: The Intersection of Politics, Philanthropy, and Investment

00:49:02: Discovering Philanthropy

00:55:14: Importance of Travel and Cultural Awareness Post-Exit
00:56:22: Passion for Art, Photography and Fashion

00:58:00: Building a Large Photographic Archive

00:58:44: Handling Estates of Important Photographers after they Pass On

00:59:40: Estate Management of Deceased Photographers

01:00:20: Fulfillment in Life

01:01:41: Artwork and Business

01:02:37: Loneliness After Founders Exit

01:03:10: Isolation After Wealth Creation

01:05:10: Inherited Wealth Management

01:06:02: Shift in Wants After Selling Business

01:09:36: Turning Down Family Members' Investment Requests

01:12:07: Generosity Vs Enabling Bad Behavior

01:12:47: Parenting with Wealth

01:14:50: Responsibility Coupled with Inherited Wealth

01:15:14: Preparing Children for Inheritance

01:16:30: Selecting People to Surround Yourself With

01:20:15: Striving for a Life of Meaning and Purpose

01:24:50: Evolution of Tiger Organization and its impact

01:26:54: The Experiences and Learnings from a Long Term Marriage

Follow Adrien Cohen on: linkedin.com/in/adrien-cohen-883a1527/

Timestamps 
00:00:00: Introduction

00:01:44: Early Motivation

00:03:28: Relationship with Judaism

00:04:36: Being a spoiled rich kid

00:05:20: What parents did right

00:06:07: The world is competitive

00:09:41: Defining success

00:10:52: Leaving Goldman Sachs

00:14:21: Starting e-commerce in Vietnam

00:16:33 Motivation

00:17:32 Critical Thinking

00:18:19 Exit from Lazada

00:19:43: Current stage of his new venture

00:23:58: Dealing with feelings of being an imposter

00:25:25: Discussing financial success and its responsibilities

00:27:13: The responsibility of exited founders to make a difference
00:30:02: Discussing the unique time in history for young, self-made individuals

00:31:58: Channelling guilt and insecurities into action

00:32:48: The mission to cure paralysis

00:34:10: Sharing personal tragedy and its impact

00:38:11: Introducing the concept of venture philanthropy

00:42:24: The structure and aim of the venture philanthropic fund

00:45:22: Choosing people to surround oneself with

00:47:16: The Secret Superpower - Using Empathy and Acceptance

00:50:00: Rules, Principles, and Lessons for Creating a Unified Relationship

00:57:10: Dealing with the Control Freak Aspect

00:59:16: Balancing Work, Life, and Family

01:01:12: Raising Children with Integrity and Humor

01:02:07: How to Be Remembered - Leaving a Lasting Impact and Legacy

Mimi's zest for life and the transformative power of gratitude will leave you with a fresh perspective on personal well-being and the pursuit of purpose. Tune in for a dose of positivity and wisdom!

00:00:00: Introduction and overview of the episode 

00:00:06: Introduction of Mimi Ikonn and her ventures 

00:00:26: Achievements in the first year of business 

00:01:00: Mimi's gratitude for the platform and her reflection on financial freedom 

00:01:47: Mimi's self-awareness about financial abundance and its impact 

00:04:04: Mimi's perspective on the power and influence of businesses 

00:04:45: Mimi talks about her purpose and how she wants to be remembered 

00:05:55: Mimi discusses her influence and control over her actions 

00:06:51: Mimi talks about her childhood and the origin of her dreams 

00:09:48: Mimi's definition of success and the importance of feeling good and fulfilled 

00:12:00: Mimi's reflection on her journey after attaining financial abundance 

00:17:51: Discussion on the hunger for freedom and realization of its abundance 

00:20:10: Mimi shares about the need for stability and community in the abundance of freedom.

00:21:45: Pragmatism vs. passion in building a business 

00:22:33: A shift from not wanting to work to wanting to work 

00:23:14: Realization from building Luxy Hair 

00:24:03: Marketing strategies for Luxy Hair 

00:25:26: Work-life balance and stepping in and out of "hustle mode"
00:26:23: The process of selling Luxy Hair and what came afterwards 

00:28:46: Re-framing the concept of work as art

00:30:12: Memory of money and its influence on our attitude towards work and business 

00:31:50: The natural inclination towards creation and problem-solving in business ventures 

00:34:27: Creation of Intelligent Change and the Five Minute Journal 

00:40:27: Role and responsibilities in Intelligent Change today 

00:42:24: Personal transition: Separation from her husband Alex Ikonn 

00:43:20: Belief in Dreams and Living the Potential 

00:43:47: Navigating Relationships: Conscious expansion and maintaining respect 

00:46:31: Addressing Divorce and Its Impact on Children 

00:52:05: Defining the Next Dream: Authenticity & Potential Personal Development 

00:54:21: The Role of Friendships 

00:56:46: Living a Life of Purpose: A life Guided by Love 

01:04:28: Approach to Psychedelics and Meditation. 

01:05:58: Meditation Practice and its Importance 

01:08:19: Comparison with Psychedelic Experiences 

01:09:29: Advantages of Meditation 

01:10:05: Personal Experience with Anxiety and the Role of Meditation 

01:10:47: Overcoming Fear through Love and Meditation 

01:12:09: Conclusion and Appreciation for Deep Conversations 

Timestamps:

00:00:02: Dramatic introduction

00:00:31: Introduction to Exit Paradox Podcast

00:00:49: Guest Introduction: Pete Henderson

00:01:13: Pete's Mission to End World Hunger

00:01:28: Pete’s Experience as a War Cameraman

00:05:31: Impact of Technology and Media

00:05:56: Development of Nutritious Food Bar

00:09:03: Pete’s Early Life

00:10:49: Lion Attack Incident

00:14:23: Selling First Business and Attending Harvard

00:15:53: Pete’s First Business as a DJ

00:16:36: Transition Into Television Business

00:18:13: Building a media company

00:19:09: Growing and selling the business

00:19:47: Life after selling the company

00:23:27: Starting a new business

00:28:15: Venture in Telecommunication

00:32:06: Introducing Site: Sustainable Impact Trading Ecosystem

00:33:56: Future plans for 'food' venture

00:39:06: Building a microalgae farm in Zimbabwe
00:43:13: Reflecting on life and personal values

00:43:46: Discussing parenting based on personal experiences

00:45:54: Experience living in Africa and the children's outlook on life

00:46:55: The children's transition to British boarding schools

00:46:26: The role of money and wealth management

00:52:29: Sharing an intensifying experience in South Africa during apartheid

00:55:56: Meeting Sister Barnard and learning a valuable life lesson

00:56:40: The decision to write a book for his children

00:58:25: Defining success

00:58:44: Introduction to Pete, "the food chap"

00:59:37: Discussing role models

01:01:16: Emphasizing the power of thinking

01:02:06: What keeps Pete awake at night

01:04:55: Feelings of guilt about financial success

01:06:35: Regrets on selling a business

01:07:20: Discussing joys in life

01:07:51: How Pete wants to be remembered

01:08:23: Finding fulfillment through witnessing history

01:09:39: Final advice for listeners

Timestamps 
00:00:00: Introduction and starting point

00:06:08: Importance of education and its relevance for children of exited founders

00:15:51: Transition from a student to a start-up founder

00:22:44: Vikrant's financial journey and perspective on "paper money"

00:23:26: Going public and financial stability

00:24:46: First public interview and going public

00:25:18: Being publicly recognized

00:26:03: Preparing for going public

00:26:22: Company's valuation and public impression

00:27:48: The moment of financial settlement

00:28:20: The impact of financial success

00:29:06: The luxury of time and money, dealing with boredom

00:30:57: Exit from business

00:31:41: Sense of Identity with financial stability

00:34:29: Post exit stagnation

00:35:21: Moving from Gibraltar to London
00:37:10: Transition in thought process about wealth

00:38:30: Managing wealth

00:41:17: Cultivating a culture of giving in India

00:43:52: Impact of philanthropic activities

00:44:01: Balance between investment and giving

00:45:02: Impact beyond material possessions

00:45:57: Discussing Old Money vs New Money

00:47:10: Learning to Say No after Wealth

00:48:06: No Loans, Only Gifts

00:49:22: Missing Running a Business Day-to-Day

00:50:17: Missing the Creativity in Business

00:52:27: Business and Philanthropy

00:53:52: Founder's Pledge and Giving Better

00:58:45: The Purpose and Meaning of Wealth

01:02:06: Concerns and Worries

01:02:38: How to be Remembered

Follow Michia Rohrssen on: instagram.com/askmichia/https://www.youtube.com/@askmichiatwitter.com/AskMichia

Timestamps
00:00:25: Introduction to Michia Rohrssen

00:01:25: Discussion on Prodigy and why it was started

00:02:46: Michia's backstory and motivation for starting a business

00:04:12: Discussion on how money was a motivator

00:06:02: The dream for the future

00:07:22: On role models and carving out a unique path

00:08:40: Introducing the Youtube channel 'Ask Michia'

00:14:09: Reasons against starting a paid online course

00:18:47: Giving away a billion dollars

00:20:25: The stress over the finish line in Prodigy

00:22:10: Discussion on the formulation of Prodigy's business model

00:22:51: Fundamental Business Principles

00:23:47: Key Gap in Car Dealerships

00:24:26: Unexpected Sale of the Business in