There’s a moment in every founder’s journey where the question shifts.

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.

In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Dakota Simpson, Chief Program Officer at the Nashville Entrepreneur Center.

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

In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Stephanie Johnson, a fractional CEO and COO who specializes in helping companies eliminate what she calls operational debt.

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