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

In this episode of the Parallel Entrepreneur, Innovation Series, Mark Cleveland and Johnny Anderson sit down with Amy Henderson, Director of Infrastructure at HCA Healthcare Physician Services.

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

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Meg Chamblee, Executive Vice President for Tennessee at UDig.

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

Great experiences don’t happen by accident. They’re designed.

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 Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Dr. Jeremy Qualls, Executive Director of the Entrepreneurship & Innovation Center (EIC) and College, Career & Technical Education at Williamson County Schools.

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.
👍 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.

#ParallelEntrepreneur, #InnovationSeries, #EntrepreneurshipEducation, #LeadershipDevelopment, #FutureOfWork