Parallel Entrepreneur with Mark Cleveland

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.

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. Eve Peeterson on LinkedIn

⏱️ 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

👉 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.

 #ParallelEntrepreneur #EvePeeterson #Leadrs #MentorshipMatters #MentorshipIsBroken #LeadershipDevelopment #Reinvention #StartupEstonia #EuropeanStartups #GlobalEntrepreneur #FounderMindset #WomenInBusiness #PersonalGrowth #StartupCulture #CareerReinvention #BetterLeadership #NeverStopLearning #Estonia #MarkCleveland #ParallelEntrepreneurPodcast 

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

• Greater Nashville Technology Council
• Nashville Area Chamber of Commerce
• Nashville Entrepreneur Center
• Williamson Inc.

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.

Dakota Simpson on LinkedIn

About the Hosts

Mark A. Cleveland Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network

Johnny Anderson Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC)

👉 Join the Parallel Entrepreneur Network

👉 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

© Parallel Entrepreneur, LLC 2024- 2026

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 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.

⚠️ Note for editor: Stephanie Johnson's LinkedIn was not included in the original show notes. Please add her profile link here once confirmed.

About the Hosts

Mark A. Cleveland Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network

Johnny Anderson Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC)

👉 Join the Parallel Entrepreneur Network

👉 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

© Parallel Entrepreneur, LLC 2024- 2026

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. Amy Henderson on LinkedIn

About the Hosts

Mark A. Cleveland Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network

Johnny Anderson Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC)

👉 Join the Parallel Entrepreneur Network

👉 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: Women in Technology of Tennessee

Connect with Meg: Meg Chamblee on LinkedIn

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

Johnny Anderson Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC)

👉 Join the Parallel Entrepreneur Network

👉 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

© Parallel Entrepreneur, LLC 2024- 2026

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: Suzi Earhart on LinkedIn

About the Hosts

Mark A. Cleveland Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network

Johnny Anderson Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC)

👉 Join the Parallel Entrepreneur Network

👉 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

© Parallel Entrepreneur, LLC 2024- 2026

The leadership playbooks that built today's successful organizations were designed for a different world.

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

© Parallel Entrepreneur, LLC 2024- 2026

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: Amalia Goodwin on LinkedIn

About the Hosts

Mark A. Cleveland Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network

Johnny Anderson Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC)

👉 Join the Parallel Entrepreneur Network

👉 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 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 → Markifyapp.com
• Abigail Goddard, National Program Champion and creator of Spikey First → 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.

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.

👉 Join the Parallel Entrepreneur Network 👉 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 👉 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

© Parallel Entrepreneur, LLC 2024- 2026

Why do AI initiatives often stall? What does it take to build AI strategies that scale inside real businesses? What does responsible, human-centered AI look like in practice?

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 Jon, 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. Jon Hilton on LinkedIn

ABOUT THE HOSTS Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.

👉 Join the Parallel Entrepreneur Network 
👉 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.

© Parallel Entrepreneur, LLC 2024- 2026

In this special Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Shauna Sprague, an AI strategist, architect, and TEDx speaker with 20+ years of experience helping Fortune 500 organizations navigate technology transformation.

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. Shauna Sprague on LinkedIn

ABOUT THE HOSTS Mark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.

Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.

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