Not slower. Not more careful. Just… faster, sharper, and a little harder to categorize.

In this episode, we sit down with Daniel Innovaté, product designer, creative entrepreneur, and one of the most naturally adaptive builders you’ll come across.

Daniel doesn’t just talk about ideas. He turns them into real, working products, sometimes in minutes.

We explore what it actually looks like to build in this new era:

- Creating apps in 15 minutes instead of 6 months
- Using AI as a collaborator, not a threat
- Managing 10+ parallel projects without losing direction
- Why being a generalist might be the real advantage now
- And how speed is changing the way we think, build, and solve problems

At one point, Daniel shares how he built a fully functional app for his dog… on a plane… before landing.

It sounds trivial. It’s not.

Because underneath that story is something bigger:
We’re entering a moment where ideas don’t have to sit in notebooks anymore. They can come to life instantly.

But speed comes with tradeoffs.

We also get into:

- The tension between creativity and AI
- Why most people resist new tools (and what that really means)
- The shift from centralized platforms back to community-driven systems
- And why nature—not technology—might be the real counterbalance

This conversation isn’t about doing more.

It’s about seeing what’s possible when friction disappears.

About Daniel Innovaté
Daniel is a product designer, builder, and creative entrepreneur known for turning messy, early-stage ideas into polished, live experiences with unusual speed and clarity. He operates across multiple ventures, blending design, technology, and creativity to build platforms that solve real problems, fast.
https://www.linkedin.com/in/danielinnovate/
https://ideafactory.agency/danielinnovate

About the Host
Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum, without forcing themselves into a single path.
https://www.linkedin.com/in/macleveland/

⏱️ TIMESTAMPS

00:00 Building 20+ revenue streams at once
01:20 Welcome to The Parallel Entrepreneur
01:50 Introducing Daniel Innovaté
03:00 How we met (and why it stuck)
04:30 From Soviet refugee to builder
06:30 The mindset of a parallel entrepreneur
08:30 Why generalists win in today’s world
08:50 AI vs creativity (what surprised Daniel most)
10:45 Collaborating with AI as a creative
12:30 The speed of AI (and why it’s hard to keep up)
13:40 “AGI already happened” — Daniel’s perspective
14:05 How he chooses what to build next
15:45 “Just build it yourself” — the new playbook
16:50 The magic of building ideas instantly
17:00 The 15-minute app story (for his dog 🐶)
18:25 What “parallel entrepreneur” really means
19:05 Are younger builders embracing AI?
20:40 Why experts resist AI tools
21:30 Don’t start a company for every idea
22:25 What inspires Daniel to create
23:40 Turning ideas into real products overnight
24:00 Inside ecom.ai (automating product catalogs)
27:45 What happens when AI removes busywork
28:30 What we’ll do with all this extra time
29:20 From 1,000 lines of code to 250,000+
30:00 Why older frameworks of thinking are breaking
31:30 Speed vs quality (and finding the balance)
32:30 AI as a creative collaborator
33:20 The shift away from centralized platforms
35:00 Identity, expression, and building something personal
36:05 Trust, relationships, and the next currency
36:50 The reality of modern dating (unfiltered)
38:30 The case for slowing down
40:15 Nature vs technology
41:10 Reinventing lending (Folio Capital)
44:05 Turning images into video (render.realestate)
46:10 Protecting ideas in a fast-moving world
48:20 Building feedback loops into products
49:00 Raising capital + building in public
50:05 Reverse mentorship (learning both ways)
51:30 When mentorship backfires
52:40 Protecting your energy as a builder
53:20 Closing thoughts

But every now and then, you meet someone who’s building something deeper, something rooted in people, place, and community.

In this episode of The Parallel Entrepreneur, Mark sits down with Andy Marshall, Founder & CEO of A. Marshall Hospitality and the driving force behind Puckett’s. From his early days in the grocery business to transforming a small market with two gas pumps into a destination known for food, music, and connection, Andy’s journey doesn’t follow a typical path, it evolves with purpose.

Puckett’s didn’t grow because of a playbook. It grew because it meant something to people. And over time, that approach hasn’t just worked, it’s scaled, without losing what made it matter in the first place.

Now, Andy is stepping into a new chapter, running for Mayor of Williamson County. Not as a career politician, but as a builder shaped by decades of leading teams, serving communities, and creating places people care about.

This conversation explores what that kind of leadership looks like:

  • How Puckett’s became more than a restaurant, it became a community staple
  • The discipline behind long-term growth
  • Why community isn’t a byproduct, it’s the foundation
  • What it means to lead beyond your business
  • And why stepping into public service felt like the next right move

This isn’t just about hospitality.
It’s about building with intention, and carrying that into leadership at a different level.

𝗟𝗲𝗮𝗿𝗻 𝗺𝗼𝗿𝗲 𝗮𝗯𝗼𝘂𝘁 𝗔𝗻𝗱𝘆 𝗮𝗻𝗱 𝗵𝗶𝘀 𝘄𝗼𝗿𝗸:
https://www.puckettsrestaurant.com/
https://www.voteandymarshall.com/
https://www.voteandymarshall.com/about
https://www.facebook.com/voteandymarshall/

About the Host
Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum—without forcing themselves into a single path.
https://www.linkedin.com/in/macleveland/

About the Guest
Andy Marshall is an entrepreneur who built his career the long way, starting in the grocery business before transforming a small-town market into what is now Puckett’s, one of the most recognized hospitality brands in the region. As Founder and CEO of A. Marshall Hospitality, he’s spent years scaling a business without losing its identity, focusing on experience, consistency, and community. His work reflects a belief that great businesses aren’t just built to grow—they’re built to matter.

Not “What am I building?”
But “Who am I becoming?”

In this conversation, Mark sits down with Eve Peeterson, an Estonian strategy and transformation leader who has led across private industry, government innovation, and national startup ecosystems.

From working her way up in hospitality…
To leading Estonia’s startup strategy…
To now building a global mentorship platform…

This is a conversation about reinvention, leadership, and what it actually takes to build ecosystems that work.

They explore the real differences between US and European startup cultures, why mentorship is misunderstood, and how the best leaders keep learning, especially when they’re the ones teaching.

And maybe most importantly…
Why your next evolution doesn’t require starting over. Just saying yes.

What You’ll Learn:
- Why “perfect before launch” is holding founders back
- The real difference between US and European startup thinking
- How mentorship should actually work (and why it usually doesn’t)
- Why leadership is the root of culture — whether you like it or not
- How to keep reinventing yourself without losing who you are

About the Host
Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum—without forcing themselves into a single path.
https://www.linkedin.com/in/macleveland/

About the Guest
Eve Peeterson is an Estonian strategy and transformation leader with over 20 years of experience across hospitality, creative industries, and national innovation. From leading Startup Estonia to building cross-border initiatives like Nordic Tech Valley, she now focuses on leadership development as the founder of Leadrs.online, a mentorship platform designed to make better leadership more accessible.
https://www.linkedin.com/in/eve-peeterson/

⏱️ Key Moments
00:00 – If you’re the smartest in the room…
02:10 – Why she came to the U.S. (and what she got wrong)
05:10 – Mentorship: Europe vs U.S.

07:03 – The mistake founders make: waiting too long to sell
08:51 – Reinventing yourself (again and again)

14:24 – “Maybe I am an entrepreneur”
18:56 – Why Estonia punches above its weight

26:40 – Starting over when nobody knows you
28:22 – Why teaching is the best way to learn

31:14 – The biggest hiring mistake founders make
32:43 – Leadership sets the culture

40:04 – The decision that changed Estonia’s future
43:38 – What innovation actually means

49:47 – What she’s taking from this experience

Links & Resources

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Dakota is focused on a simple idea: founders don’t succeed in isolation. They succeed when the right systems, support, and structure are in place around them.

At the NEC, he leads the strategy and execution behind accelerator programs and founder development, helping entrepreneurs access the resources, networks, and guidance needed to grow.

But this conversation goes deeper.

It’s about what actually drives founder success beyond the idea.

They cover:
• Why ecosystems matter more than individual effort
• The role of structure in startup success
• What founders actually need at different stages
• Aligning programs, people, and outcomes
• Building more inclusive pathways to growth

Short, practical, and grounded in real experience.

Links 
- https://www.boringcompany.com/
- https://technologycouncil.com/
- https://nashvillechamber.com/
- https://ec.co/
- https://williamsonchamber.com/

About the Guest
Dakota Simpson is Chief Program Officer at the Nashville Entrepreneur Center, where he leads startup accelerators and founder programming. With a background in government and nonprofit leadership, he focuses on building systems that improve access, strengthen execution, and help entrepreneurs grow with clarity and support.

https://www.linkedin.com/in/dakota-simpson-566358306/

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Chapters
00:00:00 Speed to market and why it matters
00:00:50 Meet Dakota Simpson + role overview
00:01:54 What innovation actually means
00:02:40 Building a founder support system
00:03:42 The current surge in entrepreneurship
00:05:02 Growth in founder demand and programs
00:06:14 Shifts in founder demographics
00:07:46 Younger founders entering earlier
00:09:08 The rise of the parallel entrepreneur
00:10:32 Lower barriers and earlier risk-taking
00:11:05 Entrepreneurship by acquisition
00:11:37 AI’s impact on founders
00:12:30 What AI means for SaaS and business models
00:13:55 Speed of change and access to knowledge
00:15:00 What founders actually need to succeed
00:17:30 Building systems that support growth
00:19:30 Final thoughts on supporting entrepreneurs
00:21:00 Episode close

Most leaders recognize technical debt in software. Fewer realize the same concept exists inside organizations.

Misaligned teams. Unclear processes. Decisions that made sense in the moment but quietly compound over time.

Stephanie steps into companies during pivotal moments—growth, transition, or pressure—and helps leadership teams reconnect strategy with execution.

This conversation explores:
• What operational debt actually looks like inside organizations
• Why strategy often fails at the execution layer
• How leaders stabilize teams during change
• The hidden friction slowing growth
• What it takes to realign people, systems, and performance

If you’ve ever felt like your business should be moving faster than it is, this conversation will resonate.

About the Stephanie Johnson
Stephanie Johnson is a fractional and interim CEO/COO who helps organizations navigate complexity, stabilize operations, and drive sustainable growth. Known for her ability to quickly assess challenges and reconnect strategy with execution, she works with leadership teams to improve performance, strengthen alignment, and eliminate operational friction. Stephanie has led across global teams and organizations, bringing a balance of operational rigor, executive leadership, and people-centered transformation.

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Chapters
00:00:00 The idea of operational debt
00:00:44 Episode introduction + Stephanie’s leadership focus
00:01:10 What operational debt looks like inside companies
00:02:05 Why strategy often breaks at execution
00:02:58 Stepping into organizations during pivotal moments
00:03:47 Aligning leadership teams around clarity and accountability
00:04:39 Finding the friction slowing growth
00:05:26 Stabilizing teams during transformation
00:06:19 Reconnecting strategy with operational discipline
00:07:12 Leadership lessons from high-stakes environments
00:08:05 Final thoughts on eliminating operational debt

Amy operates at the intersection of technical viability and business outcomes, aligning talent, technology, and data to drive enterprise growth inside one of the largest healthcare systems in the country.

But this conversation isn’t just about infrastructure.

It’s about what it really takes to connect strategy to execution. To build teams that understand both the financial model and the human one. And to develop workforce pipelines that strengthen an entire region.

Amy also reflects on her decade of service with the Nashville Technology Council, including her time as Board Chair, where she helped advocate for technology-focused workforce development across Tennessee, from K-12 to career changers.

This episode explores:
• Why strategic alignment is a leadership discipline
• Operating technical teams inside financial guardrails
• Building culture while scaling enterprise systems
• Workforce development as a long-term investment
• The role Nashville plays in shaping tech leadership

If you care about the future of enterprise leadership — especially where technology meets execution — this conversation is worth your time.

About Amy Henderson

Amy Henderson is Director of Infrastructure at HCA Healthcare Physician Services, where she aligns talent, technology, and data to drive enterprise performance in complex healthcare environments. With a focus on connecting technical strategy to business outcomes, she builds high-performing teams that operate with both financial discipline and cultural strength. Amy also served for a decade on the Nashville Technology Council Board, including as Chair, where she championed workforce development across Tennessee’s tech ecosystem.
https://www.linkedin.com/in/henderson-amy/

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Chapters
00:00:00 The intersection of tech viability and business goals
00:00:41 Episode introduction + Amy’s leadership focus
00:01:07 Amy’s role at HCA Healthcare Physician Services
00:01:54 Aligning talent, tech, and data inside enterprise systems
00:02:48 Operating to a financial model while scaling teams
00:03:39 Building culture within infrastructure organizations
00:04:28 Why workforce development matters in Tennessee
00:05:27 Serving on the Nashville Technology Council
00:06:18 Developing talent pipelines from K-12 to career changers
00:07:32 Leadership lessons from board service and enterprise growth
00:08:36 Episode close

Meg launched UDig’s Nashville office in 2020 and has grown it more than 10x, building not just a market presence, but a reputation rooted in trust, partnership, and long-term relationships.

But this conversation goes far beyond growth metrics.

Meg shares how Nashville’s tech community has evolved, why organizations like Women in Technology of Tennessee (WiTT) matter more than ever, and what it really looks like to lead with both excellence and inclusion.

As a past president of WiTT and a board leader at the Greater Nashville Technology Council (GNTC), Meg has helped shape the ecosystem that supports emerging leaders, especially women navigating technology careers in Middle Tennessee.

This episode explores:
• Why community is a strategic advantage in Nashville
• How WiTT is creating access, confidence, and opportunity for women in tech
• The power of real relationships in building sustainable growth
• What enterprise clients actually need from digital transformation partners
• How leadership evolves as companies scale
• Why investing in people outlasts investing in hype

If you care about technology, leadership, and building something that lasts in this city, this conversation is for you.

Learn more about WiTT: https://www.wittn.org/

Connect with Meg: https://www.linkedin.com/in/megchamblee/

About Meg Chamblee
Meg Chamblee is Executive Vice President for Tennessee at UDig, a technology consulting firm that designs and builds custom digital workflows and experience solutions for enterprise clients. She founded and leads UDig’s Nashville office, which has grown more than 10x since 2020.

Meg is a past president of Women in Technology of Tennessee (WiTT), serves on the board of the Greater Nashville Technology Council (GNTC), and co-founded the ELITE (Emerging Leaders in Technology) program. She has been recognized as an NBJ 40 Under 40 honoree and is a longtime advocate for building inclusive leadership pipelines across Middle Tennessee.

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Chapters
 00:00:00 The reality of being the only woman in the room
 00:00:52 Episode introduction + framing Meg’s leadership
 00:01:01 Meg Chamblee, UDig, and launching Nashville
 00:01:47 Why relationships drive real growth
 00:02:03 Nashville’s tech ecosystem and connection culture
 00:03:00 The impact of WiTT in Nashville
 00:04:02 Community as the foundation for scaling
 00:05:00 Leadership lessons from growing a market
 00:06:01 Investing in people and showing up to serve
 00:07:00 Board service, volunteer leadership, and long-term impact
 00:07:42 Episode close

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Suzi Earhart, CCXP, a Customer Experience and Organizational Change executive who believes better experiences begin with intentional design, empathy, and mutual understanding — and end in measurable business results.

Suzi started her career in computer science before realizing something foundational: technology alone doesn’t create great outcomes. People, process, and technology must work together. And if they aren’t aligned around the customer, trust quietly erodes.

This conversation goes beyond surface-level CX talk. We explore how leaders unintentionally design from the inside out, how unconscious bias limits true “outside-in” thinking, and why deciding between human, assisted, or self-service interactions is one of the most strategic trust decisions a company makes.

In this episode, we discuss:
- Why incentives today are tied to identity and belonging
- The challenge of truly thinking “outside-in”
- How culture and bias distort customer-centered design
- The difference between human, assisted, and automated experiences
- Why innovation requires structured change management
- Assessing whether employees are truly set up to deliver quality
- How aligned CX creates both financial and relational wealth

At just over 12 minutes, this episode delivers practical insight for founders, operators, and leaders responsible for shaping experience at scale.

About the Guest

Suzi Earhart, CCXP is a Customer Experience and Organizational Change executive based in Denver, Colorado. She is passionate about improving experiences through intentional design, empathy, and mutual understanding — outcomes she believes must ultimately be proven in business results.

Beginning her career in Computer Science, Suzi quickly recognized that sustainable innovation requires alignment across people, process, and technology. Her work focuses on helping organizations think like their customers, challenge unconscious bias, and intentionally decide when to use human, assisted, or self-service models.

She holds certifications in change management and has led initiatives including:
- Strategic and technology roadmaps
- Journey mapping and Voice of the Customer systems
- Service delivery redesign
- Organizational change management programs
- Governance system creation
- Employee capability and “do-ability” assessments

Throughout her career, she has remained committed to servant leadership and mentoring — helping others reach their full potential while building systems that deepen trust and results.

Connect with Suzi here: https://www.linkedin.com/in/suzi-earhart-ccxp-220663/

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Chapters:
00:00:00 Incentives, Identity & Brand Association
00:00:49 Episode Introduction
00:01:41 Suzi’s Background: Tech, People & CX
00:02:00 Why Innovation Demands Change
00:04:01 Brand as Identity & Belonging
00:05:01 The Full Customer Ecosystem
00:06:00 Designing Platforms Customers Struggle With
00:07:00 Fitting Into the Fabric of Customers’ Lives
00:09:00 “Our Customers Don’t Understand”
00:10:01 Perspective, Bias & Trust Decisions
00:12:01 Innovation as Intentional Design

In this episode of The Parallel Entrepreneur – Innovation Series, hosts Mark Cleveland and Johnny Anderson sit down with Amalia Goodwin, Global Managing Director of Adaptive Organizations at Slalom, to confront a reality most executives quietly avoid:

Incremental change is no longer safe. It’s organizational suicide.

Amalia works with C-suite leaders and boards who understand that AI transformation isn’t about tools, it’s about redesigning how organizations sense, decide, and evolve at scale. This conversation goes far beyond technology and into the deeper work of leadership courage, organizational design, and the role companies play as architects of society’s future.

We explore what it actually means to build an adaptive organization, one capable of continuous reinvention rather than reactive survival.

In this episode, we discuss:
- Why AI transformation fails without leadership courage
- The danger of applying yesterday’s playbooks to tomorrow’s problems
- What “innovation metabolism” really means inside organizations
- How leaders can balance quarterly performance with long-term survival
- Why organizations must see themselves as civic architects, not just profit engines
- Designing decision-making systems that can keep pace with exponential change
- The overlooked societal impact of AI governance and organizational choices

Amalia brings insights shaped by 25+ years and 100+ global transformations, blending strategic clarity with moral responsibility. This is a conversation for leaders who know the future isn’t something you react to, it’s something you design.

Chapters:
 00:00:00 “Courage feels a lot like fear when you’re in it.” (Cold open)
 00:00:47 Episode introduction + why this conversation matters
 00:01:07 The systems that made you successful won’t survive the AI age
 00:01:16 Why incremental change is actually dangerous right now
 00:01:37 Amalia on helping organizations succeed in a technology shift
 00:03:54 “The definition of value is changing.”
 00:04:22 How companies are evaluating AI strategy (M&A lens)
 00:05:23 Adaptive leadership + reinvesting in continuous change
 00:06:00 Learning velocity as a new measure of value
 00:06:25 Decision velocity: when do leaders know enough to move?
 00:07:27 “Innovation metabolism” — how leaders fuel themselves differently
 00:07:56 Addressing fear in strategic decision-making
 00:08:13 It’s okay to be afraid — making AI adoption fun (Bingo + games)
 00:09:59 The moment AI “blew me away” (and rewrote an SOW)
 00:10:29 The real leader work: humility, new mindsets, new skill sets
 00:10:41 “Courage feels a lot like fear when you’re in it.” (Expanded)
 00:11:28 Relearn vs. Unlearn — why unlearning is harder
 00:12:23 Six-month roadmaps vs. 3-year plans
 00:13:19 Massive 30-year transformative vision
 00:14:01 AI as a playground — bringing back play
 00:15:03 Hackathons, bake-offs, and low-code teams winning
 00:16:00 Agentic workflows + giving unexpected leaders a stage
 00:16:55 Closing: “A bake-off sounds like the right answer.”

About the Guest
Amalia Goodwin is the Global Managing Director of Adaptive Organizations at Slalom, where she partners with C-suite leaders and boards to reimagine how organizations lead through exponential disruption.

Her work focuses on the intersection of AI transformation, leadership courage, and organizational responsibility, helping companies design systems capable of continuous reinvention. Amalia is a recognized thought leader on adaptive strategy and organizational courage, with insights featured in Fortune, Forbes, HR.com, Unite.AI, and Slalom’s global research on AI-enabled organizations.

She is known for introducing leaders to what she calls “innovation metabolism”, the capacity to transform fast enough to survive, without being consumed by change itself.

🔗 Connect with Amalia on LinkedIn:
https://www.linkedin.com/in/amaliagoodwin/

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Jeremy leads one of the most compelling early-stage entrepreneurship models in the region—where students don’t just learn about innovation, they practice it. Inside the EIC, high school students launch real businesses, products, and services while earning academic credit and developing leadership skills that typically come much later in life.

During the conversation, Jeremy shares examples of how this model comes to life, including:

• Anthony Beckett, founder of Markify → http://Markifyapp.com
• Abigail Goddard, National Program Champion and creator of Spikey First → http://Spikeyfirst.com

These stories reflect what the EIC is built to do: help students move from ideas to execution, and from confidence to ownership.

Under Jeremy’s leadership, the EIC has grown from 70 students to more than 500 applicants, secured over $17 million in grants, and built a mentor network of 100+ business and community leaders—all focused on developing entrepreneurial thinkers early.

In this episode, we explore:

• Why entrepreneurship is a mindset, not a job title
• How leadership development changes when it starts earlier
• What founders can learn from education systems—and vice versa
• Why culture and coaching matter more than curriculum
• How community partnerships create real-world opportunity

CHAPTERS
 00:00:00 Entrepreneurship as the Heartbeat, Not a Track
 00:00:50 Building the Future of Work Before It Starts
 00:01:00 Jeremy Qualls and the Vision Behind the EIC
 00:01:45 Rethinking Traditional Career & Technical Education
 00:02:15 From Ideas to Action: National Pitch Competitions
 00:03:10 Teaching Business Plans, Ownership, and Real Skills
 00:04:10 Why Culture and Coaching Matter More Than Curriculum
 00:05:20 Discovering What’s Possible: The Markify Story
 00:06:30 Giving Students Real Responsibility Early
 00:07:35 Mentorship, Trust, and Community Partnerships
 00:08:50 When Student Ideas Become Real Businesses
 00:10:05 Scaling Leadership Development Inside a System
 00:11:40 What Schools and Founders Can Learn From Each Other
 00:13:10 Building Confidence Before Credentials
 00:14:30 Why Starting Earlier Changes Everything
 00:15:40 Final Reflections on Leadership and Opportunity

ABOUT OUR GUEST
Dr. Jeremy Qualls is the Executive Director of the Entrepreneurship & Innovation Center (EIC) and College, Career & Technical Education for Williamson County Schools. A leadership strategist, coach, and educator with more than two decades of experience, Jeremy has built a people-first model for developing entrepreneurial thinkers and future leaders. Under his leadership, the EIC has grown from 70 students to more than 500 applicants, secured over $17 million in grants, and built a mentor network of 100+ business and community leaders. His work focuses on cultivating culture, ownership, and leadership at every level.

ABOUT THE HOSTS
Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.
https://www.linkedin.com/in/macleveland/

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.
https://www.linkedin.com/in/johnnyonbrand/

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.
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#ParallelEntrepreneur, #InnovationSeries, #EntrepreneurshipEducation, #LeadershipDevelopment, #FutureOfWork

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland sits down with Jon Hilton, Shareholder-in-Charge of the LBMC AI Practice, to address these questions.

Jon brings a rare mix of experience, enterprise data science, large-scale digital transformation, and leadership forged through military service. From this conversation with John, you'll learn:

- Where AI strategy usually breaks down
- How to move from pilots to production without chaos
- Why clarity beats complexity every time
- The leadership mindset required to scale AI responsibly
- This conversation is for executives, founders, and operators who want results, not hype.

CHAPTERS:

 00:00:00 AI Isn’t a Technology Problem — It’s a Leadership Problem
 00:00:40 Introducing Jon Hilton: Leading AI Practice at LBMC
 00:01:47 The Strategy Disconnect: Executives vs. Employees
 00:02:40 West Point + Combat Tours: Leading Through Fear, Chaos & Uncertainty
 00:03:55 Building the Veterans Tech Peer Group in Nashville
 00:04:57 Military Technology + Nashville: What’s Being Built and Why It Matters
 00:06:27 The AI Tool Explosion: Don’t Chase Tools — Define the Problem
 00:08:25 AI’s Expanding Attack Surface: Scams, Security & New Risks
 00:09:42 “In Absence of Orders, Attack”: Courage and Forward Motion in AI
 00:10:24 Avoiding Paralysis: Deliberate Action Without Rushing
 00:12:03 Bringing People Along: Sentiment, Trust & Internal Buy-In
 00:12:55 Leveraging Veterans Well: What Corporate Leaders Need to Understand
 00:13:31 Translating Military Experience to Corporate Value (Network + Skills)
 00:15:10 Closing Thanks & Service Appreciation

ABOUT OUR GUEST
Jon Hilton helps organizations turn AI from an experiment into a scalable capability. As Shareholder-in-Charge of LBMC’s AI Practice, he works with leadership teams to define practical AI strategies, identify where automation and intelligence actually create value, and build systems that can scale responsibly across the organization. A data scientist by training with experience at ExxonMobil and EY, Jon brings a disciplined, execution-first perspective shaped by enterprise environments and military leadership. His work focuses on helping leaders make better decisions about when to use AI, where to apply it, and how to do so without creating risk, chaos, or wasted investment.
https://www.linkedin.com/in/jonathan-hilton/

ABOUT THE HOSTS
Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.
https://www.linkedin.com/in/macleveland/

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.
https://www.linkedin.com/in/johnnyonbrand/

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.
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Shauna is known for helping leaders move beyond the AI hype and into confident execution—building clear roadmaps, designing intelligent workflows and agents, and scaling automation responsibly. She’s led AI initiatives across 49 business units and brings hands-on experience with tools like AWS, Power BI, Zapier, n8n, and LangChain.

In this episode:
 • Why most people aren’t afraid of AI — they’re just overwhelmed by it
 • How to move from curiosity to confident AI execution (without getting lost in buzzwords)
• The “automate the mundane” mindset that gives teams time back for meaningful work
• A parent-friendly AI hack: photo → sports schedule → fully automated calendar
• The first practical tools to start with, even if you don’t have a big budget or deep technical expertise
• When to use workflows, automation, RPA, and when it’s time for AI agents
• Why working at the top of your skill set is becoming the new competitive advantage
• How to scale AI responsibly,and why human-centered, inclusive AI matters

Shauna brings clarity, humility, and a deep sense of purpose to a topic that feels overwhelming for a lot of teams. If your organization has been circling AI wondering where to start, this conversation will help you take the next step ,with confidence.

Chapters:
00:00:00 “Eliminate the task — make yourself valuable”
00:01:13 Introducing Shauna Sprague + what this episode is about
00:02:45 Shauna’s core idea: automate the mundane, protect the human work
00:03:34 The parent use-case: photo → sports/school schedule → calendar automation
00:04:02 Daily AI assist: meeting digest + LinkedIn “who I’m meeting with” rundown
00:05:33 Why resistance is normal (and how skeptics become champions)
00:05:52 The low-cost starting point: RPA tools for ~$20/month
00:06:09 When teams “graduate” to agents (LangChain / LangGraph)
00:06:41 Working at the top of your skill set (sales example: stop the busywork)
00:07:50 The empowering question: “Where do I start with AI?”
00:08:15 First recommendation: Zapier + plug-and-play automations
00:08:40 Practical example: Gmail automation + VIP alerts (and filtering sales emails)
00:09:13 Time back unlocks creativity (resources aren’t the limiter anymore)
00:10:02 Upskill move: build something in n8n + become the hero
00:10:26 Closing thought: “They don’t lay off valuable people”

ABOUT OUR GUEST
Shauna Sprague is an AI strategist, architect, and TEDx speaker with 20+ years in technology innovation. She has led AI and automation initiatives across 49 business units, built intelligent workflows and agents, and developed AI personas that streamline operations and increase efficiency. She’s also a board member, STEM advocate, and champion for inclusive innovation.
https://www.linkedin.com/in/shaunasprague/

ABOUT THE HOSTS
Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.
https://www.linkedin.com/in/macleveland/

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.
https://www.linkedin.com/in/johnnyonbrand/

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.
👍 Like this episode? Leave a comment or share it with someone who leads across lanes.

👉 Join the Parallel Entrepreneur Network: (link below)
👉 Subscribe for more Innovation Series conversations with builders and operators.
👍 Like this episode? Leave a comment or share it with someone who’s ready to make AI practical.

#ShaunaSprague #ParallelEntrepreneur #InnovationSeries #AILeadership #PracticalAI #AIStrategy #Automation #AIForBusiness #FutureOfWork #HumanCenteredAI #InclusiveAI #DigitalTransformation #NashvilleTech #Entrepreneurship #LeadershipPodcast

Rod’s journey, from growing up in public housing in Nashville to leading a nationally recognized, mission-driven tech recycling company, is a powerful example of what community, purpose, and leadership can create.

In this episode:
• Why community is Nashville’s greatest strength
• How mobility, transit, and opportunity are deeply connected
• What’s fueling Nashville’s new leadership renaissance
• How to use “dead time”, traffic, commutes, swims, for growth
• Why passion outside of work strengthens culture inside it
• How companies relocating to Nashville are shaking things up
• The surprising role of musicians, artists & creators in tech culture
• The city’s collaborative DNA, and how to protect it

Rod’s story is as grounded as it is extraordinary, and this conversation is filled with the kind of insight that only comes from someone who’s built a life on purpose, service, and second chances.

Chapters:

 00:00:00 Introducing Rod McDaniel: Competitive Drive & Entrepreneurial Roots
 00:01:10 Early Lessons from Sports, Discipline & Team Culture
 00:03:05 Learning to Win Without Burning Out
 00:05:00 First Ventures and the Reality of Risk
 00:07:15 Navigating Failure, Pressure & Self-Doubt
 00:09:40 Building Confidence Through Repetition and Trust
 00:12:05 Leadership Beyond the Title
 00:14:30 Accountability, Standards & Personal Ownership
 00:17:00 What Real Grit Looks Like Over Time
 00:19:20 Building Teams That Actually Work
 00:21:45 The Importance of Culture Before Scale
 00:24:10 Why People Matter More Than Process
 00:26:30 Decision-Making Under Uncertainty
 00:29:00 Growth, Patience & Long-Term Thinking
 00:31:25 Lessons Learned the Hard Way
 00:33:40 Balancing Ambition with Perspective
 00:36:00 Redefining Success at Different Stages
 00:38:30 Community, Connection & Giving Back
 00:41:00 Nashville’s Role in Shaping Leaders
 00:43:20 Creating Impact Beyond Business
 00:45:40 Advice for Founders in the Middle
 00:48:10 Staying Grounded While Scaling
 00:50:30 Final Reflections on Leadership & Legacy

ABOUT OUR GUEST
Rod McDaniel is CEO of S3 Recycling Solutions, a 5x Inc. 5000 company and Best Place to Work honoree. A native Nashvillian and community advocate, Rod has driven more than 3,000% revenue growth, speaks nationally on sustainability and leadership, and serves on major boards including the Nashville Entrepreneur Center and Nashville Technology Council.
https://www.linkedin.com/in/rod-mcdaniel-7478729/

ABOUT THE HOSTS
Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.
https://www.linkedin.com/in/macleveland/

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.
https://www.linkedin.com/in/johnnyonbrand/

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.
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#RodMcDaniel #S3Recycling #NashvilleTech #LeadershipPodcast #MissionDrivenBusiness #CommunityLeadership #EntrepreneurStory #Inc5000 #SustainabilityTech #FaithAndBusiness #PurposeDrivenLeadership

Mark Blaze is the kind of leader communities grow around. As President & CEO of the Greater Nashville Technology Council, he’s less interested in headlines and more focused on connection, collaboration, and long-term impact.

In this Innovation Series episode, recorded live at the Greater Nashville Technology Council Innovation Summit, Mark joins hosts Mark Cleveland and Johnny Anderson for a grounded, honest conversation about what makes Nashville different, and what it will take to turn momentum into global prominence.

If you care about ecosystems, talent, leadership, and building something bigger than any one company, this conversation is for you.

In this episode:

• Why Nashville already has “all the pieces of the puzzle”
 • How public–private partnership accelerates real innovation
 • What servant leadership looks like at a city-wide scale
 • The importance of finding, developing, and retaining tech talent
 • Why collaboration — not competition — is the region’s real advantage
 • How reverse mentorship strengthens modern leadership
 • What it will take for Nashville to earn worldwide tech prominence

Chapters:

 00:00:00 Welcome to the Innovation Series from the Nashville Innovation Summit
 00:01:20 Introducing Mark Blaze & the Greater Nashville Technology Council
 00:02:35 Why Nashville Is the Best Place to Start and Grow a Business
 00:03:55 Geographic Advantage, Tax Policy & Momentum
 00:05:10 “We Have the Height” — Nashville’s Natural Gifts
 00:06:30 Collaboration as a Competitive Advantage
 00:07:45 Servant Leadership and Mark’s Influences
 00:09:10 Learning from Reverse Mentorship
 00:10:40 Government as a Partner in Innovation
 00:12:20 Public & Private Investment Working Together
 00:13:55 What’s Still Missing — And Why Nothing Is Broken
 00:15:30 Connecting Talent, Capital & Opportunity
 00:17:10 The Vision for Nashville’s Tech Ecosystem in 3 Years
 00:18:45 Finding, Developing & Retaining Talent
 00:20:30 The Region’s “Special Sauce”: Its People
 00:22:10 Final Thoughts on Community, Leadership & What’s Next

Show Notes:

• Share and engage with this interview on LinkedIn: Click here

Connect with Mark Blaze
• LinkedIn – Mark Blaze
• Greater Nashville Technology Council – technologycouncil.com

About Our Hosts
• Mark Cleveland — Managing Director at Kensington Park Capital, founder, M&A strategist, and host of The Parallel Entrepreneur
• Johnny Anderson — Entrepreneur-in-Residence at the Nashville Entrepreneur Center, advisor, and tech community leader

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.
👍 Like this episode? Leave a comment or share it with someone who leads across lanes.

Michael Peters is a rare kind of founder: one who leads both with technical depth and creative clarity. In this episode, we dive into the frameworks behind his companies Lazarus Alliance and Continuum GRC, the origin of the HORSE Project, and how he balances operational intensity with deep personal discipline.

If you're building more than one thing—and trying to stay grounded while doing it—this conversation is for you.

In this episode:

• How Michael turned spreadsheet pain into an AI-driven compliance platform
• His decision to turn down a major buyout
• What it means to lead a “family-responsible” company
• How he manages time, noise, and multiple companies with intention
• His upcoming leap from cybersecurity to sci-fi storytelling

Chapters:

00:00:00 Introducing Michael Peters: Venture Catalyst & Cybersecurity Pioneer
00:01:52 Lazarus Alliance: Audits, Compliance & Global Reach
00:04:15 From “Spreadshits” to Automation: Birth of Continuum GRC
00:05:03 The HORSE Project: One Question, Many Frameworks
00:06:21 Automating the Boring Stuff
00:06:45 Pivoting to Continuum GRC and Passing on a Buyout
00:09:41 Navigating Jurisdictions: From FedRAMP to GDPR
00:11:07 Why We Let Competitors White-Label Our Tech
00:12:18 My First Business: Cannons, Cabins & Capitalism at Age 9
00:13:34 Hacking Bell Labs and Exploring the Internet in the 90s
00:14:49 Selling My ISP in 1995 Before the Web Was Cool
00:16:00 Using AI to Transform Compliance & Technical Writing
00:17:30 Time Management, Focus Time, and Email Discipline
00:20:08 Structure, Boundaries, and Protecting Family Time
00:22:45 Creating a Family-Responsible Culture at Work
00:25:50 Managing Auditors vs. Software Creatives
00:27:20 Overcoming Upward Delegation with Great Leadership
00:28:35 Aligning Vision Across Two Very Different Companies
00:30:00 The Traits That Make Parallel Entrepreneurs Thrive
00:31:30 Why I Work in 15-Minute Bursts
00:33:01 Advice to My Younger Self: Be Bolder
00:35:30 The Power of Younger Friends and a Growth Mindset
00:37:21 Books on Our Nightstands
00:38:50 Engineering Meets Creativity in My Daily Workflow
00:40:30 Solving Problems Before They Become Disasters
00:41:42 Biggest Challenge: Bureaucracy vs. Innovation
00:43:29 What’s Next: A Sci-Fi Trilogy at 4 A.M.
00:46:32 The Books I’ve Written and the LifeLock Exit
00:48:19 Togetherness, Legacy, and Mars
00:50:49 What You Didn’t Ask: The Secret Sauce I Won’t Share

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Connect with Michael Peters - LinkedIn – Michael Peters
• Continuum GRC - continuumgrc.com
• Lazarus Alliance - lazarusalliance.com
• To Sell is Human: The Surprising Truth about Moving Others by Daniel Pink - https://www.danpink.com/books/to-sell-is-human/ 
• The Crowd: A Study of the Popular Mind by Gustave Le Bon - https://www.amazon.com/Crowd-Study-Popular-Mind/dp/1636000169 
• Time Anxiety by Chris Guillebeau - https://www.timeanxiety.com/ 
• Securing the C Level: Getting, Keeping, or Reclaiming that Executive Title by Michael Peters - https://www.amazon.com/Securing-Level-Getting-Reclaiming-Executive/dp/146796882X 
• The Holistic Operational Readiness Security Evaluation: HORSE Project Series: Governance Documentation and Information Technology Security Policies Demystified by Michael Peters - https://www.amazon.com/Holistic-Operational-Readiness-Security-Evaluation/dp/1468063871 

👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me
👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.
👍 Like this episode? Leave a comment or share it with someone who leads across lanes.

Carla's bold curiosity and relentless learning has had great impact on transportation, public policy, and corporate governance. From deploying bus rapid transit in underserved neighborhoods to baking the perfect baguette, this episode celebrates the human side of engineering and entrepreneurship.

Chapters List:

00:00:00 – Introduction to Carla Bailo
00:01:00 – Carla's Impact on Cities and Roads
00:03:19 – Columbus Wins the Smart Cities Challenge
00:06:50 – Rethinking Mobility for Underserved Communities
00:10:13 – Logistics Innovation: Rickenbacker Middle-Mile Project
00:12:45 – A Flyer on the Door: Communication Gaps in Tech Projects
00:15:23 – Paralleling Transportation, Economic Access, and Planning
00:18:36 – Start Small, Learn Fast: Scaling Smart City Systems
00:21:24 – Asking Better Questions: Carla’s Mentoring Style
00:23:33 – Think in Seven Generations: Long-Term Urban Planning
00:25:58 – Carla on Joining Corporate Boards and Boardroom Roles
00:28:00 – Lessons from Her Father on Responsibility and Preparation
00:32:29 – Learning Upstream Oil & Gas Through Hands-On Curiosity
00:34:20 – CEO Oversight and Navigating Shifting Political Climates
00:37:22 – What Makes a Great Board and a Good CEO
00:40:55 – Mentoring Done Right: Listening and Mutual Learning
00:46:50 – Grandparent Wisdom and Generational Teaching
00:49:49 – The Joy of Embracing the Unknown
00:53:07 – Baking Baguettes & Balancing Curiosity with Relaxation
00:54:40 – Surviving as a Woman Engineer in the ‘70s and ‘80s
00:57:54 – Final Reflections: Making a Difference at Scale

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Carla Bailo, NACD.DC on LinkedIn - https://www.linkedin.com/in/carla-bailo-nacd-dc-604ba19/ 
• Smart Columbus - https://smartcolumbus.com/?utm_source=chatgpt.com 
• US Department of Transportation’s Smart City Challenge - https://www.transportation.gov/briefing-room/us-department-transportation-announces-columbus-winner-unprecedented-40-million-smart 
• Society of Automotive Engineers – https://www.sae.org/ 
• Automotive Women’s Alliance Foundation - https://awafoundation.org/ 
• The Road to the Top is Not on the Map: Conversations with Top Women of the Automotive Industry by Carla Bailo – https://www.amazon.com/Road-Top-Not-Map-Conversations/dp/0768000920
• The Road Forward: More Conversations with Top Women in the Automotive Industry by Carla Bailo –  https://www.sae.org/publications/books/content/r-513/ 
• Women in Mobility Bundle by Carla Bailo - https://www.amazon.com/Women-Mobility-Bundle-Carla-author/dp/1468603574/ 

Enjoy this episode? Don't forget to like, subscribe, and share with fellow entrepreneurs! For more insights and to join our community, visit parallelentrepreneur.com.

In this fast-paced sequel we dive into:

• How Matthew rescued a bankrupt currency-trading firm and scaled it to $1 B+ in volume.
• Why he calls Bitcoin “a collectible—like Beanie Babies” and predicts its slide back to reality.
• Dollar dominance, tariffs as modern-day tribute, and the hidden mechanics of fiat liquidity.
• AI-driven disruption—from accountants to animation studios—and the rise of “one-person unicorns.”
• Freedom as America’s true currency, and how Gen-Z parallel entrepreneurs can seize the moment.

Stick around to the end for Matthew’s no-BS advice on patents, cap tables, and turning unused assets into new revenue with AI.

Chapters:

00:00:00 Matthew Joynes Show Teasers
00:00:32 Part 2 Kick-Off With Matthew Joynes
00:01:19 From Law to Saving a Bankrupt FX Firm
00:04:28 Market Manipulation: Gold, Silver, Currencies
00:06:12 Bitcoin Debate: Commodity or Currency?
00:09:39 Crypto Regulation & Generational Wealth Gaps
00:11:20 Money Creation: Share Price as Printing Press
00:13:00 “Bitcoin Is a Beanie Baby”
00:13:54 Why the Dollar’s Purchasing Power Rose
00:14:44 Tariffs, China’s Trap & Deflation Forces
00:17:11 Digital Dollar, CBDCs & Surveillance Risks
00:18:28 Freedom as America’s Ultimate Currency
00:22:21 Rethinking Value in an AI-Robot Economy
00:23:59 Tariffs Through a Business Lens
00:25:15 Tribute Economy & the Stock-Market Train
00:31:01 Adapt, Adopt, Change: Redefining Failure
00:33:54 Patent Wars Versus Creative Marketing
00:35:37 Why Patents Usually Waste Money
00:38:50 Gen-Z’s Parallel Entrepreneurship Boom
00:41:54 Pinpoint Apps & the Free-Service Model
00:45:40 Renting Idle Assets With AI Matching
00:47:27 Knowledge Is Cheap, Everything as a Rental
00:49:12 Phones, Cubes & Voice-First Futures
00:51:38 “Spend the $20 and Learn AI”
00:53:37 Animation Disrupted: IP vs. Algorithms
00:56:00 Final Takeaways & Thanks to Matthew

Show Notes:

Matthew Joynes – LinkedIn - https://www.linkedin.com/in/matthewjoynes
Gamevice - https://gamevice.com 
LifeMed AI - https://lifemed.ai/
Pulley - https://pulley.com/
CompaniesHouse.gov (free UK company filings)

👉 Subscribe for more conversations that unleash potential everywhere.
🎧 Listen to the audio pod & get extras: https://theparallelentrepreneur.transistor.fm/
🚀 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/

In this high-voltage conversation you’ll learn:

▸ Why Joynes says the real product of your company is its share price
▸ How LifeMed AI replaces 90,000 manual billing jobs with 120 staff and a neural network
▸ The fatal cap-table mistakes that make a start-up “un-investable”
▸ Post-capitalist realities: one-person, billion-dollar AI companies, robot labor, 7-day weeks disappearing
▸ Practical first steps for founders—tokenization, options, warrants, “buying your own time,” and more

Chapters:

00:00:00 Matthew Joynes Show Teasers
00:00:26 Meet Matthew Joynes, “Apex” Parallel Entrepreneur
00:02:31 Why AI Will Rewrite History
00:09:29 The Fear (And Opportunity) in AI
00:12:27 From Blind to Seeing: AI As New Vision
00:13:30 Work, Creativity, and Post-Capitalism
00:15:54 Parallel Entrepreneurs as Creators
00:17:24 What Matthew’s Reading Now
00:18:50 Why Every Tech Founder Is Parallel
00:22:00 “Your Product Is Your Share Price”
00:25:32 Biggest Mistakes in Forming a Company
00:29:10 Turning Shares Into Currency
00:30:27 Building an Investable Cap Table
00:37:52 Competing With (And Eating) Yourself
00:38:45 AI As Your Personal Teacher
00:44:10 Follow Your Curiosity, Not Just Passion
00:49:30 Selling a Film With Just Script & Poster
00:52:20 AI Accelerates Every Creative Idea
00:56:55 Letting Go, Buying Your Own Time
00:57:30 Stop Spending on Others—Invest in Yourself
00:59:17 Teaser for Part Two

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Matthew Joynes – LinkedIn - https://www.linkedin.com/in/matthewjoynes
• Gamevice - https://gamevice.com  
• Stolen (2012) - http://www.stolen-movie.com/ 
• Bullet (2014) - https://www.youtube.com/watch?v=tdF9Vcv4cCo 
• I Am Soldier (2014) - https://www.youtube.com/watch?v=7LIqnkUl0zA 
• Marmadue (2022) - https://scfilmsinternational.com/current-films-animation-titles/marmaduke-3d/
• Dragonkeeper (2024) - https://dragonkeepermovie.com/ 
• LifeMed AI - https://lifemed.ai/ 
• Pulley - https://pulley.com/
• Brendan Iribe - https://brendaniribe.com/ 
• Backbone One - https://playbackbone.com/ 

Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/

Whether you’re a founder with five side projects, an artist‑parent, or a multipotentialite who refuses to “pick a lane,” this 15‑minute talk will give you:

• A new definition of success (alignment, not hustle)
• Real‑life examples from the Parallel Entrepreneur Network 
• A 60‑second guided reflection you can do right now 
• Practical prompts to weave business, art, family and growth into one powerful tapestry

Chapters:

00:00:00 Intro — What “parallel” really means 
00:01:55 The origin of The Parallel Entrepreneur project 
00:04:17 Case study: Caitlin MacGregor’s aligned life 
00:07:08 Insight: The power of slowing down 
00:09:40 When stillness feeds creativity 
00:11:32 Paralleling vs. Pivoting 
00:13:05 Guided reflection exercise 
00:14:40 Final invitation + takeaways 

Join the community:
https://ParallelEntrepreneur.com/

Subscribe for more talks & founder stories:  
https://www.youtube.com/@ParallelEntrepreneur?sub_confirmation=1

Key Quotes
“Success isn’t in speeding up; it’s in letting every lane of your life feed the others.” 
“When who you are shows up in everything you do, stress becomes spaciousness.”

Connect with Mark
• Twitter – https://twitter.com/MarkCleveland 
• LinkedIn – https://www.linkedin.com/in/mark‑cleveland/
• Podcast – https://parallelentrepreneur.com/podcast 

Connect with Creative Mornings
https://creativemornings.com/

Show Notes:

• Share and engage with this video on LinkedIn: Click here

In this episode, he and Mark Cleveland explore:

• Following Your Heart: Why Tim chose cigars and contemporary art
• Improv & Entrepreneurship: Leveraging “Yes, And” to handle surprises & spark creativity
• Exiting at the Top: Inside the CAO sale, key lessons in valuation & deal structure
• Nonprofit vs. For-Profit: Contrasts in building teams, mission, and sustainability
• Staying Centered: Yoga, mindful scheduling, and choosing environments that fuel innovation

Parallel Entrepreneurs, subscribe now and tell us in the comments which Oz insight struck your fancy—was it engineering meets art, or harnessing improv in daily business?

Chapters List:

00:00:00 Meet Tim Ozgener: Nashville’s Multi-Passionate Unicorn
00:01:14 Why Follow Your Passions?
00:02:23 The Art & Science of Cigars
00:05:09 Improv Skills in Business
00:07:14 Launching OZ Arts: A Different Kind of Startup
00:09:22 The Power of Authentic Connection
00:12:13 Lessons from Dad: Engineering Meets Entrepreneurship
00:15:18 Time Management & Team Trust
00:19:00 Nonprofit vs. For-Profit: Contrasting Cultures
00:22:00 Building Global Distribution
00:29:08 The CAO Exit Story
00:37:14 Yoga, Flow & Mindful Entrepreneurship
00:42:00 Embracing Failure & Authenticity

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• CAO Cigars - https://www.caocigars.com/ 
• OZ Arts - https://www.ozartsnashville.org/ 
• Crowned Heads Cigars - https://www.crownedheads.com/ 
• Oz Family Cigars - https://ozfamilycigars.com/ 
• The Revenge of the Tipping Point: Overstories, Superspreaders, and the Rise of Social Engineering by Malcolm Gladwell - https://www.amazon.com/Revenge-Tipping-Point-Overstories-Superspreaders/dp/0316575801/ 
• Headway app - https://headwayapp.co/ 
• Art Basel - https://www.artbasel.com/ 
• Ken Cope Consulting, LLC - https://kencopeconsultingllc.com/ 

Key Highlights:

• Opportunity Filtering – The three questions Justin always asks before launching a new product.
• AI as Internal Auditor – How Strike Graph deploys large language models to verify compliance automagically.
• Co-Founder vs. Solo Act – Winning arguments for teamwork, board partnerships, and the joys of not going it alone.
• Music & Mental Health – Surprising ways that daily creative outlets (and old-school Ashtanga yoga) keep Justin’s energy fresh.

Ready to sharpen your parallel potential? Subscribe now and share which insight resonated most—AI? Mentoring? Or making that “hundredth monkey” leap?

Chapters List:

00:00:00 Introduction to Justin Beals and StrikeGraph
00:02:02 Spotting Opportunities: Three Key Questions
00:04:10 Building Strike Graph: Why Framework Matters
00:06:06 Understanding Risk in Entrepreneurship
00:08:19 Systems Thinking & Data Models
00:12:09 Trends in Cybersecurity and Business Impact
00:14:31 Surviving a Downturn: B2B SaaS Realities
00:16:18 Co-Founders & Good Investors
00:19:43 Leveraging AI in Cybersecurity
00:22:35 Mentoring & Measured Learning
00:27:25 Creativity and Leadership in Entrepreneurship
00:33:13 Lessons Learned in Business and Co-Founding
00:40:36 Navigating Change with Venture Backers
00:43:19 The Emotional Landscape of Collaboration
00:45:18 The Art of Flexibility in Leadership
00:46:20 Shifting Focus: From Sales to Strategic Partnerships
00:48:00 Scaling with Core Values
00:51:38 Identifying Aha Moments in Customer Experience
00:53:57 The Impact of AI on Business and Society
00:57:52 Empowerment through Creative Technology
00:01:05:47 The Future of AI Companions
00:01:08:21 Lessons from the Past: Advice for the Future
00:01:18:58 The Essence of AI and Poetry

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Secure Talk podcast - https://www.strikegraph.com/secure-talk-podcast
• StrikeGraph – https://www.strikegraph.com/ 
• Roundbox Global - https://roundbox.com/
• Koru - https://www.koru.global/
• Snow Crash by Neal Stephenson - https://en.wikipedia.org/wiki/Snow_Crash 
• Zealot: The Life and Times of Jesus of Nazareth by Reza Aslan -  https://www.amazon.com/ZEALOT-Life-Times-Jesus-Nazareth/dp/140006922X 
• Europe Between the Oceans: 9000 BC – AD 1000 by Barry Cunliffe - https://www.amazon.com/Europe-Between-Oceans-9000-BC-AD/dp/0300170866 
• The Three Body Problem by Liu Cixin - https://en.wikipedia.org/wiki/The_Three-Body_Problem_(novel) 
• Hundredth Monkey Effect - https://en.wikipedia.org/wiki/Hundredth_monkey_effect

Key Highlights:

• Secrets of a $100M Scale – How Robert powered up his cell phone stores with EOS and big-picture “why.”
• Dark Night of the Merger – The day Google listings vanished, store traffic plummeted, and Robert sold to survive.
• Harnessing AI as "Idea Manager" – Why we should treat AI like a creative partner, not a threat.
• Mindset & Breathwork – Tools Robert swears by to stay calm, refocus, and unlock “superhero energy.”
• The Clark Kent vs. Superman Moment – Overcoming shame, embracing authenticity, and letting your real self shine.

If you’re juggling multiple ventures—or dreaming of it—hit Subscribe and share in the comments which breathwork or AI tip resonates most with you!

Chapters List:

00:00:00 Introduction to Robert Hartline
00:00:47 Scaling to $100M & EOS Discipline
00:03:01 How Robert Reframes to Discover His “Why”
00:08:38 The T-Mobile Merger: From Momentum to Meltdown
00:14:20 Darkness, Divorce, and Post-Merger Fallout
00:19:45 The COVID Mask Pivot & Parallel Entrepreneurship Gone Wild
00:23:49 AI as Your “Idea Manager”
00:27:40 The Energy of Connection and Creation
00:30:12 How to Flow: Add Love, Breath & Movement
00:32:43 Unique Ability and the Power of Community
00:34:56 Discovering Your Why and Core Values
00:37:16 The Role of Love in Business and Life
00:40:00 Clark Kent vs. Superman: Embracing Your True Self
00:42:46 AI as a Decision-Making Tool
00:50:07 Energy Management and Personal Practices
00:52:17 The Biggest Gift Ever & the Future
00:54:56 Slowing Down to Speed Up
00:58:15 Wrap-Up & Gratitude

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• The Decision Experience - https://thedecisionexperience.com/ 
• Entrepreneurial Operating System (EOS) - https://www.eosworldwide.com/ 
• Soma Breath Guided Breathwork Training and Certification- https://www.somabreath.com/ 
• Wim Hoff Breathing - https://www.wimhofmethod.com/breathing-exercises 
• Strategic Coach by Dan Sullivan - https://www.strategiccoach.com/book-a-call
• Traction: Get a Grip on Your Business by Gino Wickman - https://www.eosworldwide.com/traction-book 
• Driven: Understanding and Harnessing the Genetic Gifts Shared by Entrepreneurs, Navy Seals, Pro Athletes, and Maybe You by Douglas Brackmann and Randy Kelley - https://www.iamdriven.com/ 
• 10x Is Easier Than 2X: How World-Class Entrepreneurs Achieve More by Doing Less by Dan Sullivan and Benjamin Hardy - https://10xeasierbook.com/ 
• The Three Marriages: Reimaging Work, Self and Relationship by David Whyte - https://davidwhyte.com/store/book/the-three-marriages/ 
• Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert - https://www.elizabethgilbert.com/books/big-magic/
• CallProof, sales tracking app - https://callproof.com/ 

Highlights:

• From OR to Revenue Tech – Why Michael traded the surgical suite for software code.
• 24 Years Sober – How recovery principles shape his resilience in business.
• Nail Compliance, Stop Revenue Bleed – The healthcare billing problem Michael solves.
• Mindset Hacks – Handling stress, negativity, and “the shadow self” with unshakable resolve.
• Chasing Flow – Moving from “hustle 24/7” to deeper creativity and real presence.

Chapters List:

00:00:00 The Journey of Dr. Michael Sprintz
00:01:45 Resilience and Tenacity in Recovery
00:04:27 The Intersection of Pain and Addiction
00:06:40 Lessons from Entrepreneurship
00:09:00 Aligning Vision and Values
00:10:39 The Birth of Solarian
00:13:21 Navigating the Software Landscape
00:14:08 The Role of AI in Healthcare
00:16:13 Market Response and Growth Strategies
00:18:14 The Art of Adaptation
00:20:07 Authenticity in Business
00:22:08 Future Aspirations and Innovations
00:24:48 Best Advice Received: What you sell your company is not what you created at first
00:28:52 Helping Others See Beyond Their Current Reality
00:29:53 Understanding the Opioid Crisis and Healthcare Misalignment
00:32:45 Balancing Stress and Personal Life as a CEO
00:34:13 Time Management and Effective Communication
00:35:56 Lessons from Life and Death Experiences
00:37:43 Finding Meaning and Making Ethical Decisions
00:39:37 Embracing Technology and Uncertainty in Healthcare
00:41:27 Reflecting on Past Accomplishments and Future Risks
00:42:55 Living Life with No Regrets
00:43:55 The Impact of Literature on Personal Growth
00:45:14 The Connection Between Humanity and Business
00:52:44 Art, Music, and the Flow of Life
00:57:13 Trusting the Process and Letting Go

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Cellarian Inc., healthcare software that improves diagnosis, treatment, documentation and risk-management for substance use disorder and other diseases - https://www.cellarian.com/ 
• A Life of Meaning: Relocating Your Center of Spiritual Gravity by James Hollis - https://jameshollis.net/hollisBooks.html 
• Living with Borrowed Dust: Reflections on Life, Love and Other Grievances by James Hollis - https://jameshollis.net/hollisBooks.html 
• The Alchemist by Paulo Coelho – https://www.amazon.com/Alchemist-Paulo-Coelho/dp/0062315005/ 
• Never Split the Difference: Negotiating As If Your Life Depended on It by Chris Voss – https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805 
• Mark’s 2025 Bhavana – https://www.youtube.com/watch?v=twS9UpeqeF0 

Highlights:

• Parallel Mindset – John runs two consultancies that fuel each other.
• M&A Mastery – Turning chaotic post-acquisition phases into opportunities for deeper alignment.
• Keeping Pace with Change – Simple practices to handle lightning-fast market shifts without burning out.
• AI & the Future – How advanced tech is reshaping value propositions—and why you need to adapt now.
• Leading with Love – The surprising “sticky note” that guides John’s leadership style.

Chapters List:

00:00:00 Meet Organizational Alignment Guru John Farkas
00:02:08 Taming Chaos: Context Switching Across Industries
00:05:17 Birth of Candor: Solving the "Alignment" Dilemma
00:07:20 Understanding Organizational Alignment
00:09:13 Overcoming Fear & Building Trust in Organizational Change
00:11:29 Pace Paradox: Thriving in Accelerating Markets
00:13:46 Flattened Org Charts & Shared Objectives
00:16:02 The Impact of AI on Business Models
00:18:26 Spectacular Failures & Lessons Learned
00:20:37 The Mentoring Gap & Real Team Building
00:22:52 How do you manage time and energy between ventures
00:23:43 Superpowers: Context Switching & Listening
00:26:42 Self-Care & the Importance of Loving Leadership
00:30:16 M&A and Human Capital: Missing the Biggest Asset
00:34:19 Facing an AI-Driven Future
00:39:38 Rapid Fire: North Star, Books, Gifts & Wise Words
00:43:38 Closing Thoughts: Curiosity, Intent, and Love

Show Notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/3HDZLsS
• Ratio, a growth marketing consultancy helping B2B healthtech and fintech companies - https://goratio.com/ 
• Candor, a growth architecture firm - https://www.candorgrowth.com/ 
• 99% Invisible podcast - https://99percentinvisible.org/ 
• The Power Broker by Robert Caro - https://99percentinvisible.org/club/ 
• Conclave by Robert Harris - https://www.amazon.com/Conclave-novel-Robert-Harris/dp/1101972904
• John's "walk on" song - Beautiful Day by U2

Highlights include:

• How Silas bootstrapped VendEngine from idea to digital disruption
• An innovative approach to transforming inmate financial transactions
• Scaling strategies that grew the business from county jails to 425 facilities
• Merging startup agility with corporate synergy at Tyler Technologies
• Critical lessons on embracing failure, pivoting, and mastering time management
• Leadership insights on integrity, mentorship, and building winning teams
• The mindset behind taking calculated risks and seizing future opportunities, including AI trends

Chapters:

00:01:00 Introduction: Bootstrapping & Exiting with Silas Deane
00:02:56 VendEngine's Genesis: Innovating Inmate Transactions
00:04:32 Transforming the Inmate Payment System
00:07:27 Scaling Success: From County Jails to 425 Facilities
00:11:13 Corporate Synergy & Strategic Growth: Acquisitions & Hardware Innovation
00:16:09 Finding Synergies and Growth Opportunities
00:17:14 Learning Through Failure: Time Management & the Power of Pivoting
00:21:32 Leadership in Action: Integrity, Mentorship & Government Insights
00:24:46 Overcoming Financial Hurdles: Hustling to a $90M Exit
00:29:09 The Journey of a Parallel Entrepreneur
00:32:21 Learning from Mistakes and the Freedom of a Clean Slate
00:34:29 Feeding the Creative Drive
00:36:26 The Power of Historical Insights and Identifying Patterns
00:39:08 The Importance of Business Basics
00:40:19 Discovering and Nurturing Talent
00:41:45 Turning Mistakes into Learning Opportunities
00:46:25 Advice to My Younger Self
00:48:14 The Nature of Risk in Entrepreneurship
00:50:18 The Value of a Large Addressable Market

Show Notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/4l4RZH8
• VendEngine Inc. - https://www.businesswire.com/news/home/20210901005799/en/
• Tyler Technologies (NYSE:TYL) - https://www.tylertech.com/ 
• KPMG - https://kpmg.com/us/en.html 
• Deane/Smith & Partners, a Nashville-based, award-winning public relations, marketing and advertising agency - https://deanesmith.agency/ 
• NIC transaction management solution - https://www.florida.egov.com/services.html 
• University of Kentucky, Gatton College of Business and Economics, Von Allmen Center for Entrepreneurship - https://vace.uky.edu/node and https://vace.uky.edu/bootcamp/mentors/silas-deane
• Junior Achievement of Middle Tennessee, a nonprofit that inspires and prepares young people for success - https://jausa.ja.org/index
• The Power of Broke: How Empty Pockets, a Tight Budget, and a Hunger for Success Can Become Your Greatest Competitive Advantage by Daymond John - https://daymondjohn.com/pages/power-of-broke 

Highlights include:

• His transformative journey from the Naval Academy to leading a multipreneur empire
• How Leap Partners was born out of a shared vision and 45+ acquisition successes
• Proven strategies for identifying quality businesses and integrating diverse cultures
• Lessons learned from early exits and the importance of “begin with the end in mind”
• The secret to balancing rapid growth, due diligence, and celebrating success
• Insights on building a people-first, family-centric company culture
• Rapid-fire insights on must-read books and what fuels his day-to-day drive

Whether you're running multiple businesses or planning your next big leap, this conversation is packed with actionable wisdom for every ambitious entrepreneur.

Chapters List:

00:01:00 Introduction to John Cerasuolo and Leap Partners
00:02:06 Naval Academy: Forging a Leader
00:04:09 Leap Partners Genesis: From ADS Security to Home Services
00:08:31 Identifying Acquisition Opportunities
00:11:05 Integrating Cultures in Acquisitions
00:14:36 Exiting with Great M&A Advisors
00:18:17 Challenges in Due Diligence
00:20:07 Celebrating Success
00:23:03 Mindfulness and Daily Practices
00:24:18 Advice to His Younger Self
00:26:08 Learning from Each Other in Business
00:27:15 Navigating Talent Challenges in the Trades
00:29:21 Rapid Fire Insights
00:32:20 Recognition and Awards
00:33:03 Scaling a Culture of Happiness
00:34:20 Modeling Leadership Behavior
00:35:22 A Day in the Life of a CEO
00:36:48 Choosing the Right Financial Partners
00:38:09 Surrounding Yourself with Talent
00:39:22 Books that Inspire
00:40:21 Closing Thoughts on Life and Business

Show Notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/3HUWntG
• Leap Partners, a Family of Service Companies - https://www.theleappartners.com/ 
• Fossil Future by Alex Epstein - https://www.forbes.com/sites/johntamny/2022/09/29/book-review-alex-epsteins-excellent-and-essential-fossil-future/ 
• Atlas Shrugged by Ayn Rand - https://aynrand.org/novels/atlas-shrugged/ 
• Joe Scarlett, former President and Chairman of Tractor Supply Company - https://joescarlett.com/ 

In this episode of Parallel Entrepreneur, Mark Cleveland sits down with Caitlin MacGregor, CEO and Co-Founder of Plum, to talk about building a high-growth company while raising a family and defying the usual startup playbook.

If you’re juggling multiple ventures—or planning to—Caitlin’s journey will inspire you to embrace change, experiment with collaboration, and double down on what really drives success.

Highlights:

• Power Couple: Why being married to her co-founder is Caitlin’s superpower (despite investor skepticism).
• 13 Years of Growth: Balancing fundraising with customer-driven revenue, and why sales might matter more than venture capital.
• People Over Résumés: How Plum’s behavioral data approach uncovers “diamonds in the rough” for any role.
• Authentic Leadership: Leading with love, care, and collaboration to break down silos and foster real engagement.
• GenAI & the Future: Why tasks, not jobs, are being automated—and how to reinvent your organization for exponential success.

Don’t miss these candid insights from a founder who’s rewriting the rules on entrepreneurship and talent strategy.

Chapters List:

00:00:56 Meet Caitlin MacGregor: Founder, CEO & Human Potential Champion
00:02:44 When Your Co-Founder Is Your Spouse
00:05:08 Growing a Family & a Company Simultaneously
00:09:21 Fundraising Lessons: 99 No’s for 1 Yes
00:15:17 Rethinking Growth in a Shifting Market
00:17:30 Why Sales Might Matter More Than Fundraising
00:20:48 Integrating Feminine Dimensions of Leadership
00:25:16 Symbiotic Health - the New Model for Business Success
00:26:51 Well-being, Mindfulness & Self-Awareness
00:31:06 The Science of Unlocking Human Potential
00:35:00 Hire for Behaviors, Not Resumes
00:35:57 The Collaborative Operating System: Eliminating Silos
00:38:48 Perfection vs Collaborative Creation
00:45:42 Transforming Company Culture to Eliminate Politics
00:48:00 A Hiring Experiment That Sparked Plum
00:52:18 Advice for Future Generations
00:57:07 GenAI & the Future of Work
00:59:55 Books, Escapes & Art
01:04:53 The Future of Change Management

Show Notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/3FKdXQF
• Plum, a revolutionary talent platform - https://www.plum.io/  
• EY Entrepreneurial Winning Women - https://www.ey.com/en_us/entrepreneurial-winning-women-north-america/class-of-2024  
• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman - https://www.blitzscaling.com/
• Bo Burlingham - https://boburlingham.com/
• The Revenue Engine: Fueling a B2B High Octane Pipeline by Kara Smith Brown - https://therevenueengine.com/
• The Fourth Wing by Rebecca Yarros - https://rebeccayarros.com/fourthwing

About Plum:

Dive into a fresh take on talent strategy with Plum, the durable skills company. Our robust talent assessment platform, PlumThrive, helps you harness the lasting impact of the core competencies that matter. By focusing on durable skills, we transform your company into a skills-based powerhouse, allowing you to make better talent decisions across the employee journey.

Are you ready to boost your hiring precision and extend employee tenure? Explore PlumThrive and transform your workforce strategy today: https://www.plum.io/book-demo

What You’ll Learn:

• Banker Skepticism → Big Vision: How Christian overcame early financing doubts to build Nashville’s go-to coworking hub.
• The Power of Celebration: Why throwing parties and embracing small wins keeps your team and tenants inspired.
• Mindful Pauses & Ping Pong: Christian’s secret to staying calm under pressure (including his favorite “reset” technique).
• Mentoring vs. Micromanaging: How giving autonomy attracts long-term staff and nurtures a vibrant entrepreneurial ecosystem.
• Expanding Into Events & Arts: From a single building to 49 acres of innovation—Christian’s massive new development plan.

Chapters List:

00:00:00 Meet Christian Paro: The Man Behind Nashville's Most Innovative Collaboration Spaces
00:01:28 From NYU Parks & Rec to Property Investor
00:03:06 Discovering Coworking: The Birth of Center 615
00:05:19 Banking Skepticism & the Power of Relationships
00:08:29 Studio 615: Expanding into Creative Production Spaces
00:12:05 Patterns, Parties & Parallel Lessons
00:13:48 Biggest Lessons & Avoiding Over-Leverage
00:14:54 Mentoring, Not Micromanaging
00:16:32 Mindfulness Practices & the Entrepreneurial Journey
00:22:13 Designing a New 49-Acre Community
00:24:13 Mindful Pauses: Staying Centered Under Pressure
00:27:25 Rapid Fire Insights: Gifts, Mantras, Books & Jedi Wisdom
00:32:36 Do What Scares You
00:37:12 Facing Fears & Final Thoughts

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• C615, a driving force in building and shaping community in Nashville - https://c615.co/
• Artist Sergey Gordienko (the art behind Mark) - https://www.instagram.com/dowhatyoulove.artist/
• Joanna Barbera, Nashville Musician and Mindfulness Mentor - https://www.joannabarbera.com/
• 8 Decisions (Conscious Entrepreneur Tribe) by Robert Hartline - https://8decisions.com/
• Nasty Girl by Iglesias - https://open.spotify.com/track/5MghBTWUogtorQqmKBwaBn
• All about Love: New Visions by Bell Hooks - https://www.amazon.com/All-About-Love-New-Visions/dp/0060959479
• The Optimist by Sophie Kipner – https://www.amazon.com/Optimist-Sophie-Kipner-author/dp/1783525584 
• The Madness of Crowds: A Novel by Louise Penny - https://www.gamacheseries.com/books/the-madness-of-crowds/
• Do One Thing Every Day That Scares You: A Journal - https://www.amazon.com/One-Thing-Every-That-Scares/dp/0385345771
• “Jenny’s Answer (867-5309)” female empowerment parody song by Jenny Pruitt - https://www.youtube.com/watch?v=qi2Ru6vvZo0
• Tiny Happy Things: Poems by Jenny Pruitt - https://www.amazon.com/Tiny-Happy-Things-Jenny-Pruitt/dp/B0DLD78L24

What You’ll Learn:

• How to leverage distribution (and why it’s everything)
• Turning media audiences into profit engines
• When boredom is more dangerous than burnout
• Using AI to supercharge content creation and customer engagement
• The power of small, strategic M&A deals for explosive growth

Hit play and discover how to “Focus Less, Explore More” so you can scale your impact across industries—on your own terms.

Timestamps:

00:00:51 Introduction to Craig Fuller and FreightWaves
00:01:50 Revolutionizing Transportation with Data
00:03:40 The Business Model of FreightWaves
00:05:12 From Futures to Transparency in Trucking
00:06:46 The Bloomberg Inspiration for FreightWaves
00:11:56 Pursuing Opportunities to Drive Top of Funnel
00:18:45 Motivating Teams and Sharing Value
00:21:20 Finding Inspiration and Avoiding Burnout
00:26:29 Current Trends in the Transportation Market
00:34:04 Harnessing AI for Enhanced Content Creation
00:39:58 AI's Role in Customer Engagement
00:41:54 Evaluating Business Opportunities
00:42:56 The Importance of Distribution in Business
00:47:22 Asymmetric Risk and Business Strategy
00:50:10 Learning from Experience and Testing
00:56:58 The Journey vs. Destination in Entrepreneurship
01:02:37 The Value of Shared Experiences in Business

Show notes: 

• Share and engage with this interview on LinkedIn: Click here
• Bloomberg by Bloomberg - https://www.bloombergbybloomberg.com/
• The Power Law: Venture Capital and the Making of the New Future - https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X
• Range: Why Generalists Triumph in a Specialized World by David Epstein - https://davidepstein.com/range/
• The Rational Optimist: How Prosperity Evolved by Matt Ridley - https://www.amazon.com/Rational-Optimist-Prosperity-Evolves-P-s/dp/0061452068
• Outliers: The Story of Success by Malcolm Gladwell - https://www.amazon.com/Outliers-Story-Success-Malcolm-Gladwell/dp/0316017930

If you’re a Parallel Entrepreneur hungry for both impact and inner balance, this conversation is your roadmap to thriving in the fast-paced world of multi-venture leadership.

In this conversation, we dive into:

• How openness and authenticity drive healthier board relationships and better decision-making
• Why failure isn’t an option for many minority entrepreneurs
• Why relinquishing control is essential for founders who juggle multiple ventures—and how to do it effectively
• Why women-led ventures often outperform expectations and attract strong investor support
•  What’s happening outside of Silicon Valley in today’s startup world

Time Stamps:

00:00:26 Introduction to Nitin Rai and His Journey
00:05:42 The Importance of Transparency, Leading from the Heart
00:08:49 Challenges in Raising Capital: The Current Landscape
00:14:43 Balancing Multiple Ventures: The Art of Delegation
00:18:05 Navigating Exits: Lessons Learned
00:19:40 Sharing Wealth: The Entrepreneurial Approach
00:22:01 Role Models and Mentorship: Influences on Nitin's Approach
00:24:45 Identifying with Entrepreneurs: A Personal Connection
00:25:40 The Power of Small Ideas
00:25:56 The Power of Intuition
00:27:16 Mindfulness Practices and Self-Care
00:29:51 Celebrating Entrepreneurial Success
00:32:12 The Virtuous Cycle of Wealth Creation
00:34:28 Entrepreneurship as an Art
00:35:23 Defining Success in Entrepreneurship
00:38:24 The US Entrepreneurial Landscape
00:41:01 Advice to Your Younger Self
00:42:14 Reading and Continuous Learning

Show notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/43UJPKm
• Kishau Rogers, Founder of Time Study - https://kishau.com/about/
• Ania Rodriguez, Founder of JourneyTrack - https://www.journeytrack.io/about
• Allie Magyar, Founder of Hubb - https://www.linkedin.com/company/hubb/
• Monica Enand, Founder of Zapproved - https://zapproved.com/about-us/company/
• Nat Parker, Founder of Globe Sherpa (changed to Moovel North America) - http://moovelus.com/
• Ganesh Shankar, Entrepreneur & Investor - https://www.responsive.io/about/
• "Anarchy" by William Dalrymple - https://www.amazon.co.za/Anarchy-Company-Corporate-Violence-Pillage/dp/1635573955
• White Mughals by William Dalrymple - https://www.amazon.com/White-Mughals-Betrayal-Eighteenth-Century-India/dp/014200412X
• Light on Life by B.K.S. Iyengar - https://www.amazon.com/Light-Life-Journey-Wholeness-Ultimate/dp/1594865248

Whether you’re juggling multiple startups or dreaming of your first exit, Roger’s candid insights are a must-watch for any Parallel Entrepreneur.

Tune in to gain insights from a leader who believes in doing the right thing, embracing change, and leaving a lasting legacy.

Chapters:

00:00:00 Introduction to Parallel Entrepreneurship
00:00:24 Roger Brown's Journey into Cannabis Testing
00:01:18 The Thrill of Building Businesses
00:04:13 Creating Value in Business
00:05:25 Challenges in the Healthcare Industry
00:06:30 The Debate: Symptoms vs. Wellness
00:08:27 The Role of Co-Founders in Business
00:11:27 Insights from M&A Advisors
00:14:56 Lessons Learned from Selling Businesses
00:17:59 Navigating Healthcare's Evolution
00:20:22 AI's Role in Modern Business
00:23:14 Finding Balance and Recharging
00:24:44 Guiding Principles and Life Lessons
00:28:13 Learning from Mistakes
00:30:42 Legacy and Life's Purpose
00:31:53 Rapid Fire Questions
00:32:59 The Importance of Trust and Team Dynamics
00:36:44 Embracing Change and Perspective

Show Notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/43EixZQ

In this conversation, we dive into:

 - Why “failing fast” can spark rapid innovation
 - How psychometric data transforms hiring and retention
 - Cultivating a culture that scales alongside your business
 - Personal insights on mindfulness, leadership, and building strong teams

Don’t miss Jason’s fascinating journey and powerful takeaways—perfect for any parallel entrepreneur aiming to juggle multiple ventures with clarity and impact.

Chapters:

00:00:00 Welcome to the Parallel entrepreneur
00:00:29 Introduction to Jason Putnam and Plum
00:04:52 Scaling Businesses with Plum's Tools
00:10:50 Addressing Unconscious Bias in Recruitment
00:14:08 How AI is Transforming the Hiring Game
00:17:32 Understanding the Pace Paradox of Change
00:21:07 Navigating Rapid Change with a ‘People-First’ Approach
00:27:45 The Impact of AI in Our Lives
00:33:32 Lessons from Exits: Building for Success
00:36:56 How Fast Decisions Spark Innovation
00:39:46 Fail Fast, Learn Faster: The Entrepreneurial Spirit
00:44:15 How Jason Finds Mindfulness by Helping Others
00:45:16 Books Jason is currently reading

Show notes:

• Share and engage with this interview on LinkedIn:  https://bit.ly/3FMMaPA
• Plum - https://www.plum.io/
• Caitlin MacGregor (Founder and visionary behind Plum) - https://www.plum.io/about
• Move Fast, Break Shit, and Burn Out by Dr. Tracey Lovejoy and Shannon Lucas - https://www.amazon.com/Move-Fast-Break-Shit-Burn/dp/1544515774
• The Talent Fix by Tim Sackett - https://www.amazon.com/Talent-Fix-Tim-Sackett/dp/1586445227
• Scythe by Neal Shusterman - https://www.amazon.com/Scythe-Arc-Neal-Shusterman/dp/1543617948
• Spartan Up by Joe DeSena - https://www.amazon.com/Spartan-Take-No-Prisoners-Overcoming-Obstacles-Performance/dp/0544286170

Francisco shares his journey from early entrepreneurial experiences to founding Fearless Journeys, a community aimed at connecting aspiring entrepreneurs. They discuss the emotional aspects of entrepreneurship, the significance of listening to customers, and the role of fear in decision-making.

The conversation also touches on the importance of spirituality, mindfulness, and the impact of books on personal growth. Throughout, they emphasize the value of relationships and the need for an adventurous spirit in the entrepreneurial journey.

Chapters:

00:00:00 Introduction to The Parallel Entrepreneur Podcast
00:00:28 Introduction to Fearless Journeys and Francisco Gonzalez
00:02:47 The Early Entrepreneurial Spirit
00:03:42 Inception of Fearless Journeys
00:06:49 Building a Community of Innovators
00:09:54 Insights from Entrepreneurial Conversations
00:11:47 The Value of Travel and Connection
00:12:40 Role Models and Mentorship in Entrepreneurship
00:13:25 The Importance of Timing in Business Exits
00:14:31 The Pragmatic Optimist: Navigating Business Valuation
00:15:44 Identity and the Entrepreneur: Letting Go of Attachment
00:16:06 Parallel Entrepreneurship: Balancing Multiple Ventures
00:17:32 The Emotional Toll of Exiting a Business
00:19:16 Fear and Risk: Embracing the Unknown
00:23:35 Mindfulness and Spirituality: Grounding in Faith
00:24:53 Podcasts and Personal Growth: The Power of Listening
00:25:05 Books that Inspire: Lessons from 'The Alchemist' and 'Atomic Habits'
00:29:36 The Value of a Gap Year
00:32:59 Essential Skills for Parallel Entrepreneurs
00:33:51 Defining Your North Star
00:34:54 The Importance of Lifelong Learning
00:35:39 Embracing Adventure in Entrepreneurship
00:37:05 Finding Joy in Entrepreneurship
00:38:22 Delegation and Efficiency in Business
00:39:51 Building an Entrepreneurial Mindset

Show notes:

• Share and engage with this interview on LinkedIn:  https://bit.ly/3HSmpOd
• Fearless Journeys Website: fearlessjourneys.org
• Agents of Innovation Podcast - https://agentsofinnovation.org/
• Economic Club of Miami - https://www.econclubmiami.org/
• The Heart of the American Dream by Francisco Gonzalez - https://www.amazon.co.za/dp/B0DNMHVGXB
• The American Dream is a Terrible Thing to Waste by Francisco Gonzalez - https://www.amazon.com/American-Dream-Terrible-Thing-Waste/dp/B0BRDCCNHM
• The Alchemist by Paulo Coelho - https://paulocoelhoblog.com/
• Atomic Habits by James Clear - https://jamesclear.com/

Highlights:

• The biggest mistakes founders make when selling
• How to spot the perfect buyer (it’s not just about price!)
• The HVAC & Home Services roll-up wave: Who’s buying and why
• Tactical exit-prep moves that boost your valuation
• The “buy side” strategy—growing your biz by acquiring rivals

Whether you’re a serial founder eyeing your next sale or a trailblazer itching to acquire, John’s insights will help you maximize value, protect your team, and maintain the creativity that powers your parallel ventures. Don’t miss these real-world lessons from one of the industry’s most seasoned M&A advisors!

Chapters:

00:00:00 Introduction to the Parallel Entrepreneur
00:00:36 About Kensington Park Capital
00:03:02 Entrepreneurial Mindset: Diversifying Through Necessity or Passion
00:06:06 HVAC Roll-Ups: Innovation in Customer Acquisition and Service
00:10:17 Choosing the Right Buyer: Exit Strategies and Integration
00:12:36 Lessons Learned from 300+ Transactions in Investment Banking
00:17:06 Decision-Making Frameworks for Entrepreneurs and Advisors
00:20:46 Timing the Sale: Entrepreneur Advice on Business Preparation
00:22:29 Keys to a Successful Business Sale
00:25:51 Private Equity and Buy-Side Acquisitions Explained
00:30:13 First-Time vs. Second-Time Entrepreneurs: Patterns in Growth
00:36:21 Overcoming Imposter Syndrome and Embracing Positivity
00:39:00 Controlling Your Mindset: The Power of Optimism in Entrepreneurship
00:43:10 Finding the Perfect Fit: Leveraging Business Relationships
00:45:53 Innovation and AI in Mergers & Acquisitions
00:48:10 A Unique Business Sale Story: Lessons in Collaboration
00:51:11 The Value of Patience in Complex M&A Transactions
00:52:56 Celebrating Success: Gratitude and Giving Back in Business

Show Notes: 

• Share and engage with this interview on LinkedIn: Click here
• Learn more about Kensington Park Capital - https://kensingtonpark.com/
• John is currently reading "You Like It Darker" by Stephen King - https://stephenking.com/works/collection/you-like-it-darker.html

Highlights:

• How Ania leveraged her background in customer experience and innovation to launch JourneyTrack.
• The importance of listening to your customers and tying Customer Experience to ROI.
• Her strategies for building a winning team and thriving as a Parallel Entrepreneur.
• If you're an entrepreneur, leader, or innovator, this episode is packed with actionable advice and inspiration.

Chapters:

00:00:00 Welcome to the Parallel Entrepreneur
00:29:00 Introduction to Anya Rodriguez and JourneyTrack.io
00:02:12 The Importance of Customer Experience
00:06:04 Lessons from Entrepreneurship
00:08:37 Scaling and Team Dynamics
00:09:50 Mentorship and Networking
00:13:20 Navigating Capital Raising Challenges
00:15:27 Daily Life as a CEO
00:16:31 Finding Inspiration and Energy
00:18:34 Finding Investors and Building a Supportive Team
00:22:23 Defining the North Star for Impact
00:26:30 The Role of AI in Customer Experience
00:29:39 Embracing Experimentation and Agility
00:31:32 Lessons on Timing and Exit Strategies
00:33:57 Advice to My Younger Self
00:37:06 The Power of Creativity and Mentorship

Show Notes:

• Share and engage with this interview on LinkedIn: https://bit.ly/4l6NDze
• The Gap and The Gain by Dan Sullivan - https://gapandgainbook.com/
• Life Force by Tony Robbins - https://tr.tonyrobbins.com/life-force

From spinning off a $28 billion asset at Ford Motor Company to leading groundbreaking startups in e-bikes and artificial intelligence, Bill shares his journey of innovation, leadership, and impact. 

Chapters:

00:00:00 Welcome to the Parallel Entrepreneur
01:18:00 Lessons from Ford: The Foundation of Entrepreneurship
04:05:00 Lessons from Bill's father, the inventor of the CD-ROM
07:43:00 The Startup Journey: From Concept to Capital
18:20:00 Key Lessons in Entrepreneurship
24:06:00 How he disrupted the automotive and cycling industries
33:11:00 Customer-Centric Leadership
34:57:00 The Impact of AI on Business
36:17:00 AI in Education and Beyond
38:55:00 Lessons from Mergers and Acquisitions
43:06:00 Defining Your North Star
44:27:00 Bill's current goals for life
48:54:00 The Power of Boldness
50:51:00 Trusting Your Instincts
51:28:00 The Journey of Entrepreneurship

This candid and inspiring conversation explores themes of courage, resilience, and the drive to make a lasting impact. Whether you're an aspiring entrepreneur or a seasoned business leader, there's something here for everyone. 

Show Notes:

Share and engage with this interview on LinkedIn: https://bit.ly/3HyElO5

Through candid conversations, we uncover what drives these visionaries to juggle diverse enterprises, how they navigate risks and failures, and the lessons that have shaped their paths. Guests share practical advice on scaling businesses without losing their edge, balancing energy and focus across ventures, and finding inspiration in mentors and personal philosophies.

From reflections on pivotal moments like company exits to insights on living authentically and defining success, each episode offers listeners an opportunity to connect with the stories, strategies, and wisdom of trailblazers in parallel entrepreneurship.