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Parallel Entrepreneur with Mark Cleveland

Mark A. Cleveland

Mark explores the minds of visionary entrepreneurs who refuse to limit themselves to a single venture to learn how these trailblazers manage risks, innovate across industries, and turn ideas into impact.

Whether you’re scaling your first business or juggling several, this podcast is your ultimate guide to thriving as a parallel entrepreneur.

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  • 21 episodes
  • fortnightly
  • Avg 38 min
  • English

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  • #44
    October 1 · 40 min

    What It Takes to Lead More Than One Business | Dr. Tobias Kutzewski

    What if running multiple businesses isn't a failure to focus, but a different way of operating altogether? Dr. Tobias Kutzewski has spent years studying entrepreneurs who build and manage multiple ventures simultaneously. His research followed 21 entrepreneurs over time, examining how they allocate resources, respond to uncertainty, recognize opportunities, build teams, and decide when to explore something new while continuing to operate what they already have. In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Tobias to compare that research with Mark's own experience of building multiple companies throughout his career. They explore strategic optionality, the ability to prepare for and seize opportunities you cannot necessarily predict, and what happened when Tobias's research collided with the enormous uncertainty of COVID-19. The conversation also gets into one of the biggest assumptions surrounding entrepreneurship: that focus must mean doing one thing. In this episode: • What separates parallel entrepreneurs from serial entrepreneurs • Why Tobias began studying founders running multiple companies • What "strategic optionality" means in practice • How successful founders divide their time, capital, and attention • Why knowing what you don't know is a critical leadership skill • The role of trust and talent when managing several ventures • What Tobias observed when COVID-19 disrupted the entrepreneurs he was studying • Why some founders become more opportunistic during uncertainty • Mark's "pause, pivot or pursue" decision during the pandemic • Whether resilience can be developed • Why the economic impact of parallel entrepreneurship may be larger than we currently know • Why younger generations may increasingly become parallel entrepreneurs If you've ever been told you need to choose one business, one idea, or one path, this conversation offers another perspective. About Dr. Tobias Kutzewski Dr. Tobias Kutzewski is an interim finance director and freelance lecturer at the School of Business & Economics at Vrije Universiteit Amsterdam. He earned his PhD in entrepreneurship researching how parallel entrepreneurs initiate, develop, and coordinate multiple ventures over time. He is also the co-author of Strategic Optionality: Pathways Through Disruptive Uncertainty. Connect on LinkedIn 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. Connect on LinkedIn Subscribe to The Parallel Entrepreneur for conversations with founders, researchers, and leaders exploring what it takes to build, lead, and thrive across multiple ventures. Learn more about The Parallel Entrepreneur and our growing community at https://parallelentrepreneur.com/ 𝗟𝗶𝗻𝗸𝘀 & 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀: Connect with Dr. Tobias Kutzewski: Strategic Optionality: Pathways Through Disruptive Uncertainty — Surja Datta & Tobias Kutzewski Explore Tobias's research at Vrije Universiteit Amsterdam Unlocking Strategic Innovation: Competitive Success in a Disruptive Environment — Surja Datta, Sandeep Roy & Tobias Kutzewski: Follow The Parallel Entrepreneur on LinkedIn Learn more about Mark Cleveland: Happy Overall Chapters: 00:00 Are you already a parallel entrepreneur? 01:59 What is strategic optionality? 04:20 Recognizing vs. seizing opportunity 07:20 Why Tobias began studying parallel entrepreneurs 11:28 Parallel vs. serial entrepreneurship 14:37 How Mark manages attention across multiple companies 18:54 Finding and deploying the right talent 21:26 Businesses at different stages of maturity 22:27 Different types of parallel entrepreneurs 25:09 Happy Overall 26:16 Is entrepreneurship a game? 29:44 When the rules suddenly change 32:05 Mark's businesses during COVID-19 33:36 Pause, pivot or pursue? 35:25 How entrepreneurs make decisions under pressure 38:17 Studying entrepreneurs through COVID-19 41:37 Preparing for black swan events 43:15 What makes some entrepreneurs more resilient? 48:16 Mark's approach: observe, accept, act 51:13 "Why on earth do you do more than one thing?" 53:56 The economic impact of parallel entrepreneurs 57:48 How big is parallel entrepreneurship? 1:00:55 The next generation of parallel entrepreneurs

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  • #43
    September 10 · 1 hr 1 min

    The Science Behind Running Multiple Businesses at Once | Dr. Tobias Kutzewski

    What if running multiple businesses isn't a failure to focus, but a different way of operating altogether? Dr. Tobias Kutzewski has spent years studying entrepreneurs who build and manage multiple ventures simultaneously. His research followed 21 entrepreneurs over time, examining how they allocate resources, respond to uncertainty, recognize opportunities, build teams, and decide when to explore something new while continuing to operate what they already have. In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Tobias to compare that research with Mark's own experience of building multiple companies throughout his career. They explore strategic optionality, the ability to prepare for and seize opportunities you cannot necessarily predict, and what happened when Tobias's research collided with the enormous uncertainty of COVID-19. The conversation also gets into one of the biggest assumptions surrounding entrepreneurship: that focus must mean doing one thing. In this episode: • What separates parallel entrepreneurs from serial entrepreneurs • Why Tobias began studying founders running multiple companies • What "strategic optionality" means in practice • How successful founders divide their time, capital, and attention • Why knowing what you don't know is a critical leadership skill • The role of trust and talent when managing several ventures • What Tobias observed when COVID-19 disrupted the entrepreneurs he was studying • Why some founders become more opportunistic during uncertainty • Mark's "pause, pivot or pursue" decision during the pandemic • Whether resilience can be developed • Why the economic impact of parallel entrepreneurship may be larger than we currently know • Why younger generations may increasingly become parallel entrepreneurs If you've ever been told you need to choose one business, one idea, or one path, this conversation offers another perspective. About Dr. Tobias Kutzewski Dr. Tobias Kutzewski is an interim finance director and freelance lecturer at the School of Business & Economics at Vrije Universiteit Amsterdam. He earned his PhD in entrepreneurship researching how parallel entrepreneurs initiate, develop, and coordinate multiple ventures over time. He is also the co-author of Strategic Optionality: Pathways Through Disruptive Uncertainty. Connect on LinkedIn 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. Connect on LinkedIn Subscribe to The Parallel Entrepreneur for conversations with founders, researchers, and leaders exploring what it takes to build, lead, and thrive across multiple ventures. Learn more about The Parallel Entrepreneur and our growing community at https://parallelentrepreneur.com/ 𝗟𝗶𝗻𝗸𝘀 & 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀: Connect with Dr. Tobias Kutzewski: Strategic Optionality: Pathways Through Disruptive Uncertainty — Surja Datta & Tobias Kutzewski Explore Tobias's research at Vrije Universiteit Amsterdam Unlocking Strategic Innovation: Competitive Success in a Disruptive Environment — Surja Datta, Sandeep Roy & Tobias Kutzewski: Follow The Parallel Entrepreneur on LinkedIn Learn more about Mark Cleveland: Happy Overall: Chapters: 00:00 Are you already a parallel entrepreneur? 01:59 What is strategic optionality? 04:20 Recognizing vs. seizing opportunity 07:20 Why Tobias began studying parallel entrepreneurs 11:28 Parallel vs. serial entrepreneurship 14:37 How Mark manages attention across multiple companies 18:54 Finding and deploying the right talent 21:26 Businesses at different stages of maturity 22:27 Different types of parallel entrepreneurs 25:09 Happy Overall 26:16 Is entrepreneurship a game? 29:44 When the rules suddenly change 32:05 Mark's businesses during COVID-19 33:36 Pause, pivot or pursue? 35:25 How entrepreneurs make decisions under pressure 38:17 Studying entrepreneurs through COVID-19 41:37 Preparing for black swan events 43:15 What makes some entrepreneurs more resilient? 48:16 Mark's approach: observe, accept, act 51:13 "Why on earth do you do more than one thing?" 53:56 The economic impact of parallel entrepreneurs 57:48 How big is parallel entrepreneurship? 1:00:55 The next generation of parallel entrepreneurs

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  • #42
    August 18 · 45 min

    Fall in Love With the Problem, Not the Solution | Annie Cyr

    Annie Cyr saw a gap in the textile industry, wrote the book she couldn't find, and years later built the technology she wished existed. In this episode of The Parallel Entrepreneur, Annie joins Mark Cleveland to share the journey from writing The Guide to Textile Fibers to co-founding Tengiva, and what she's learned trying to modernize a complex global industry from the inside. The conversation goes well beyond textiles. Annie shares why founders should "fall in love with the problem, not the solution," how she decides which opportunities are worth pursuing, why she tested existing technology before building her own, and what fundraising has taught her about choosing the right partners. They also get into something every entrepreneur eventually has to confront: knowing your own limits. Annie shares an unexpected lesson from her time working in a hospital emergency department and how it shaped the way she approaches leadership, balance and building a company today. For anyone turning deep industry experience into a business, there's plenty here to apply. 𝗜𝗻 𝘁𝗵𝗶𝘀 𝗲𝗽𝗶𝘀𝗼𝗱𝗲; • Why Annie spent three years writing a textile reference book • How industry experience led to the creation of Tengiva • Why founders should fall in love with the problem, not the solution • How to innovate without trying to replace everything that already works • Why textile industry knowledge is so difficult to digitize • How Tengiva prioritizes which customer problems to solve • Why transparency and proprietary knowledge don't have to be opposites • Annie's approach to selling without "selling" • Why she tested existing technology before building her own • When customers should fund your growth — and when outside capital makes sense • What Annie has learned from raising venture capital • Why industry experience matters when hiring • The difference between competing with others and becoming better than yourself • What working in a hospital emergency department taught Annie about balance • Her vision for making textile sourcing more accessible to the next generation of creators 𝗔𝗯𝗼𝘂𝘁 𝗔𝗻𝗻𝗶𝗲 𝗖𝘆𝗿 Annie Cyr is the CEO and co-founder of Tengiva, a technology company modernizing commercial operations across the global textile industry. Before building Tengiva, Annie spent years working across textile development, sourcing and procurement. She is also the author of The Guide to Textile Fibers: Clothing and Fashion Industry, a practical reference created after a university professor challenged her to write the resource she couldn't find herself. Together with co-founder Carlos Agudelo, Annie began the Tengiva journey in 2018, testing existing technologies before ultimately deciding the industry needed technology purpose-built around the way textile businesses actually operate. Connect on LinkedIn 𝗟𝗶𝗻𝗸𝘀 & 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀: Tengiva: The Parallel Entrepreneur Podcast: Happy Overall: 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. Connect on Linkedin Chapters 00:00 Fall in Love With the Problem 01:05 How Annie Cyr Wrote the Book on Textiles 02:57 The Knowledge You Can't Learn From a Book 04:00 Why the Textile Industry Is So Complex 06:26 Innovation vs. Disruption 08:26 Why AI Won't Replace Human Expertise 09:58 Choosing Which Problems to Solve First 13:30 Modernizing a Protective Industry 16:34 Annie's Superpower: Selling Without Selling 19:46 Lessons Every Founder Can Use 21:05 Learn With Other People's Money 22:25 Happy Overall 23:31 What Fundraising Taught Annie 26:50 Stop Trying to Beat Your Competitors 28:21 Hiring for Industry Experience 31:19 What Annie Wants Tengiva to Accomplish 32:52 Annie's Magic-Wand Vision for Textiles 33:26 Making It Easier for New Brands to Start 36:41 Is Work-Life Balance an Illusion? 38:11 The Hospital Lesson That Changed Annie's Approach 41:16 Knowing When to Stop 42:42 Why Tengiva's Real Start Came in 2020 43:46 Raising Capital and What's Next 44:34 Closing Thoughts Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures.

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  • #41
    August 4 · 58 min

    Inside the Mind of a Former Xerox CEO | Steven Bandrowczak

    There are very few people who have led transformation at the scale Steven Bandrowczak has. After leading global technology businesses including DHL, Lenovo, HP and ultimately serving as CEO of Xerox, Steven joins Mark Cleveland to share the leadership lessons he's learned from decades of navigating disruption, reinvention and technological change. One of the most surprising moments in this conversation comes when Steven argues that AI shouldn't be owned by IT, it should be owned by HR. His reasoning challenges the way most organisations are approaching AI today and completely reframes how leaders should think about building the workforce of the future. But this episode is about far more than artificial intelligence. How do you reinvent before you're forced to? How do you lead people through uncertainty? How do you build organisations that embrace change instead of fearing it? Steven shares lessons from reinventing Xerox, leading through major acquisitions, learning from failure, mentoring future leaders and why leadership, not technology, is still the deciding factor between companies that thrive and companies that disappear. If you're building a business, leading a team or trying to understand where AI fits into your organisation, this conversation offers practical insights from someone who has led through transformation at the highest level. 𝗜𝗻 𝘁𝗵𝗶𝘀 𝗲𝗽𝗶𝘀𝗼𝗱𝗲; • Why Steven believes AI should be owned by HR, not IT • Why reinvention is harder than transformation • The biggest mistake leaders make during change • Why company culture determines whether acquisitions succeed • The real reason businesses fail to capture value from AI • Why fear is the biggest obstacle to innovation • How entrepreneurs should think about disruption • The importance of solving real business problems • Building organisations that can adapt faster • Leadership lessons from more than four decades in technology • Why kindness may be one of the greatest leadership advantages 𝗔𝗯𝗼𝘂𝘁 𝗦𝘁𝗲𝘃𝗲𝗻 𝗕𝗮𝗻𝗱𝗿𝗼𝘄𝗰𝘇𝗮𝗸 Steven Bandrowczak is the former Chief Executive Officer of Xerox and previously served as the company's President and Chief Operating Officer. Across a career spanning more than four decades, he has held senior leadership roles at DHL, Lenovo, HP and Avaya while leading major technology transformations across global organisations. LinkedIn Today, Steven advises CEOs and boards on AI strategy while teaching the next generation of technology leaders at Northeastern University. 𝗟𝗶𝗻𝗸𝘀 & 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀: SOL Consulting - Website SOL Consulting - Linkedin The Parallel Entrepreneur Podcast 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. LinkedIn Chapters 00:00 AI or Employees? Why It's Both 00:36 Introducing Steven Bandrowczak 02:03 Reinventing Xerox as CEO 06:22 Why Mergers Fail 08:32 Keeping a 100-Year-Old Company Innovative 12:13 Why AI Is Accelerating So Fast 15:40 Leading People Through AI Change 17:57 Why HR Should Own AI Agents 20:29 What the Nortel Collapse Taught Steven 24:22 Why AI Can't Replace Strategy 28:54 Growing Up in Queens & Becoming Fearless 33:49 Leadership, Kindness & Reading the Green 36:07 Building an AI Strategy That Creates Value 39:03 The Biggest Business Risk Today 41:10 Why Companies Aren't Getting Value from AI 43:02 The Future of Parallel Entrepreneurship 48:18 The CEO's Responsibility to Build Leaders 51:15 Reverse Mentorship & Developing Talent 53:10 What Steven Is Reading 55:51 What He'd Tell His Younger Self 57:53 Closing Thoughts Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures.

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  • #40
    July 21 · 45 min

    The Comfort Trap Every Entrepreneur Must Escape | Joe De Sena

    Joe De Sena has built one of the world's most recognised endurance brands. As the founder and CEO of Spartan, he's spent decades proving that resilience isn't something you're born with. It's something you build. In this conversation with Mark Cleveland, Joe shares the business philosophy behind Spartan, why comfort quietly destroys ambition, how surrounding yourself with the right people changes your future, and why entrepreneurs should deliberately seek challenges instead of avoiding them. They also explore Joe's unlikely path from cleaning swimming pools in Queens to Wall Street, launching Spartan after years of failure, navigating 9/11, surviving COVID, and ultimately helping obstacle racing reach the Olympic Games. This isn't just a conversation about fitness. It's about leadership, business, discipline, resilience and building a life you'll actually be proud of. In this episode: • Growing up around hustle and learning business before adulthood • The three lessons that shaped Joe's career • Why relationships matter more than transactions • Leaving a successful business to start over on Wall Street • The long road to building Spartan • What entrepreneurs get wrong about comfort • Why difficult goals literally reshape your brain • Future memory and finishing what you start • Building companies around purpose instead of money • The importance of community and environment • How to stay motivated for decades, not weeks • Why the journey matters more than the destination If you're building a business, leading a team, or simply trying to become a stronger version of yourself, this conversation is full of timeless lessons. About Joe De Sena Joe De Sena is the Founder and CEO of Spartan, the world's leading endurance sports and obstacle racing brand operating in more than 40 countries. He is a New York Times bestselling author, entrepreneur, endurance athlete and one of the world's leading voices on resilience, discipline and human performance. Links & Resources: Join the Parallel Entrepreneur Network: The Parallel Entrepreneur Podcast: Connect with Joe De Sena: Website: LinkedIn: Instagram: X: Facebook: YouTube: Spartan: Joe's Books: 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. Linkedin Key Moments 00:00 Why your brain avoids hard things 00:00:45 Meet Joe De Sena 00:02:03 Growing up around hustlers and the Bonanno family 00:06:37 Four rejections before Cornell said yes 00:12:19 Leaving construction for Wall Street 00:16:15 How failure led to building Spartan 00:18:37 Launching an endurance race after 9/11 00:22:38 The Parallel Entrepreneur mindset 00:26:17 Why comfort is the real enemy 00:29:16 Future memory and why finishing hard things matters 00:31:14 Building an environment for peak performance 00:33:15 Journey vs. destination 00:35:30 Reinventing Spartan during COVID 00:37:05 When data tells you to compromise 00:38:12 The 15-year vision to reach the Olympics 00:40:10 Building a mission bigger than money 00:43:40 Joe De Sena's challenge for every entrepreneur Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures. #Entrepreneurship #Business #Founder #BusinessLeadership #BusinessGrowth #Leadership #HighPerformance #SuccessMindset #Resilience #PersonalDevelopment #BusinessPodcast #JoeDeSena #Spartan #ParallelEntrepreneur #MarkCleveland

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  • #39
    July 7 · 59 min

    How to Build an Extraordinary Life Without Following One Path | Ian Adamson

    What do engineering, world championship sport, product innovation, television production, and the Olympic movement all have in common? In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Ian Adamson, Chair of the World Pentathlon Multisport Obstacle Commission, to explore a career built on curiosity, continuous learning, and saying yes to opportunities most people would never consider. Ian has spent decades moving between engineering, elite sport, business, product development, and global leadership. From designing products for Nike and competing as a professional adventure racer to helping guide obstacle sports into the Olympic movement, his career is proof that the experiences we collect often become our greatest advantage. Along the way, the conversation explores parallel entrepreneurship, decision-making, resilience, innovation, engineering thinking, AI, adventure, leadership, and why living an extraordinary life often begins by embracing the unexpected. In this episode: • Why Ian believes your greatest superpower is the ability to learn • How engineering shaped his approach to leadership and problem solving • The mindset behind managing multiple careers at once • Walking across China... twice • Why saying yes creates opportunities you could never plan for • Lessons from building world-class sporting events and international organizations • What innovation looks like when you're too early for the market • How AI is accelerating discovery and changing the way we learn • Why the Olympic movement is about creating better humans—not just better athletes • The importance of curiosity, legacy, and leaving the world better than you found it Whether you're an entrepreneur, leader, engineer, athlete, or simply someone who enjoys learning from people who have taken an unconventional path, this conversation offers practical wisdom and a refreshing perspective on building a meaningful life. Links & Resources 👉 Join the Parallel Entrepreneur Network 🎧 The Parallel Entrepreneur Podcast Connect with Ian Adamson: 💼 LinkedIn 🌐 World Pentathlon Multisport 🌐 World Obstacle 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. Key Moments 00:00 Introduction & Ian's extraordinary career 01:36 Managing energy across multiple careers 04:47 From engineer to world champion athlete 09:01 Building a global sport and the Olympic movement 12:04 Why saying yes changes everything 15:24 What Ian would tell his younger self 16:02 Walking across China... twice 19:06 Breaking impossible goals into achievable steps 21:04 Why learning how to learn matters most 23:00 Innovation, timing, and being too early 26:30 The power of constant pressure 29:10 The parallel entrepreneur mindset 34:37 Identity, curiosity, and lifelong learning 37:47 AI, discovery, and the future of learning 45:21 Why everyone should train like an astronaut 46:39 Lessons from the ocean and thinking beyond ourselves 50:23 Engineering, safety, and managing risk at scale 54:29 The Olympic movement and creating better humans 58:23 Final thoughts Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures. #ParallelEntrepreneur #MarkCleveland #IanAdamson #Entrepreneurship #Leadership #Innovation #Olympics #Engineering #AdventureRacing #ObstacleRacing #BusinessPodcast #PersonalGrowth

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  • #38
    June 23 · 1 hr 20 min

    The AI Skill Every Working Adult Needs to Learn | Spencer Handley

    What happens when a musician, software engineer, educator, and entrepreneur all show up in the same person? In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Spencer Handley, Founder and CEO of Sonora, to explore a career built on curiosity, learning, and challenging conventional thinking. Spencer shares the story behind Sonora's growth from a guitar education company into a modern learning institution that has helped nearly 6,000 students—including multiple Grammy winners—reach new levels of mastery. He also discusses the recent national attention surrounding Sonora's AI transformation, what actually happened behind the headlines, and why he believes learning to work with AI may become one of the most important skills of the next decade. Along the way, the conversation explores accelerated learning, entrepreneurship, creativity, the future of work, building companies around personal passion, and what world-class performers can teach all of us about continuous growth. In this episode: • Why curiosity has been the common thread throughout Spencer's career • The two-year guitar plateau that ultimately led to founding Sonora • How Sonora has helped thousands of musicians accelerate their learning • Lessons from Grammy-winning artists and elite performers • What really happened when Sonora rebuilt its technology stack • The opportunities and risks AI presents for founders and professionals • Why Spencer believes learning how to manage AI agents is becoming a critical skill • The future of education, work, and human creativity Whether you're a founder, creator, educator, musician, or someone navigating the rapid changes happening in business and technology, this conversation offers practical insights and a thoughtful perspective on what comes next. Links & Resources 👉 Join the Parallel Entrepreneur Network The Time article: The Small Businesses Already Replacing Workers With AI Spencer's response: AI Didn't Replace Our Workers. It Replaced Our SaaS Stack. Connect with Spencer: 🌐 Sonora Music Education 🌐 Spencer Handley's website 🌐 Pioneer Species 🎸 Playback Sessions on YouTube 📸 Spencer Handley on Instagram 💼 Spencer Handley on LinkedIn Sonic Sphere: sonic-sphere.com Connie Yang: Connie Yang on Instagram Connie Yang's portfolio 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. Key Moments 00:00 Introduction & Spencer's bold prediction about AI 00:43 Welcome to The Parallel Entrepreneur 01:17 The common thread: curiosity and learning 02:00 What is Sonora? 03:00 Why Grammy winners still take lessons 06:38 Studying music at UCLA and the search for mastery 07:38 The "intermediate plateau" that changed everything 10:20 The teacher who transformed Spencer's playing 12:05 How Sonora was born 14:05 The science of learning and creating momentum 17:15 Teaching through transformation, not information 19:45 Building community around mastery 23:00 Creative projects, side ventures, and parallel entrepreneurship 27:00 Why Spencer learned to code 30:00 Using software to solve your own problems 33:30 The entrepreneurial advantage of technical skills 36:15 AI, agents, and the future of work 44:25 The TIME Magazine story 47:40 What really happened inside Sonora's AI transformation 50:30 Why the middle-management layer may disappear 52:00 The human work AI can't replace 55:10 Rebuilding an entire SaaS stack 58:40 Pioneer Species and teaching AI skills 01:01:10 Flow, energy, and avoiding burnout 01:05:20 How Spencer decides what to build next 01:08:50 Managing multiple ventures without losing focus 01:12:40 Lessons from world-class musicians 01:15:20 What Spencer has changed his mind about 01:17:30 The future of learning, AI, and human potential 01:19:10 Final thoughts Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures. #ParallelEntrepreneur #MarkCleveland #SpencerHandley #Sonora #ArtificialIntelligence #Entrepreneurship #FounderStories #CreatorEconomy #FutureOfWork #BusinessPodcast © Parallel Entrepreneur, LLC 2024- 2026

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  • #37
    May 26 · 1 hr 21 min

    Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song

    What happens when an entrepreneur spends decades helping founders transition, scale, and protect the businesses they've built? In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Douglas Song, founder and CEO of Protos Capital, for a wide-ranging conversation on independent sponsors, lower middle market acquisitions, leadership, succession planning, AI, uncertainty, and what founders often overlook when preparing for growth or exit. Doug shares lessons from dozens of transactions across multiple industries, including how he evaluates leadership teams, why organic growth still matters more than acquisition rollups, and what makes a business resilient in a world filled with constant disruption. But this conversation also becomes deeply personal. Doug reflects on immigrating to the United States from South Korea as a child, watching his parents build a life through entrepreneurship, and how that experience shaped the way he thinks about people, stewardship, and long-term value creation. The conversation also explores: The rise of the independent sponsor model Why succession planning is becoming urgent for founder-led businesses AI adoption in lower middle market companies How great operators handle black swan events Why culture and people matter more than spreadsheets Building blue-collar entrepreneurship pathways for the next generation The difference between growing fast and growing well Legacy, learning, and designing a life with intention Whether you're building, scaling, buying, selling, or simply trying to lead well through uncertainty, this episode offers a rare combination of strategic insight and lived experience. Subscribe for more conversations with founders, operators, creators, and visionaries building in parallel. 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 Douglas Song is the Founder and CEO of Protos Capital, an independent sponsor firm focused on lower middle market businesses. For more than 25 years, he has worked alongside founders and management teams to help businesses grow, transition, and navigate acquisitions with a people-first approach centered on long-term value, stewardship, and community. 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. Key Moments 00:00 Why founders need transition plans, not just exits 00:47 Introducing Douglas Song and Protos Capital 01:30 Entrepreneurship Through Acquisition (ETA) explained 03:00 Independent sponsors vs. traditional operators 05:00 Why operators matter more than dealmakers 06:01 The coming succession wave for founder-led businesses 08:15 What "another bite at the apple" really means 11:50 How Protos measures investment success 12:40 Defining the lower middle market 13:50 AI adoption in family-owned businesses 16:30 Using AI during due diligence 17:20 What founders overlook before a transaction 20:00 Growth by acquisition vs. organic growth 23:40 Why organic growth still wins with buyers 24:38 Evaluating leadership teams under pressure 27:40 Black swan events and constant uncertainty 31:35 Managing leverage and protecting downside risk 35:22 Is Douglas Song a parallel entrepreneur? 37:20 Lessons learned across multiple portfolio companies 41:15 Why flexibility matters more than fixed timelines 44:20 Different types of capital partners 46:35 What makes founders great partners 49:27 Mentoring the next generation of independent sponsors 52:25 Why community matters in business 53:48 Protecting culture after acquisition 55:08 Doug's immigrant family story and entrepreneurial roots 57:20 Building blue-collar entrepreneurship pathways 01:01:45 AI, uncertainty, and creating opportunities for young people 01:06:05 Books, learning, and the concept of flow 01:10:12 Writing letters to his children 01:11:40 Advice for navigating uncertainty 01:13:40 Restoration, creativity, and balance 01:15:45 Formula 1, Monaco, and memorable experiences 01:17:18 Doug's long-term life plan and legacy goals 01:20:14 Final reflections and closing thoughts #ParallelEntrepreneur #DouglasSong #PrivateEquity #Entrepreneurship #MergersAndAcquisitions #Leadership #BusinessGrowth #IndependentSponsor #AI #FounderJourney © Parallel Entrepreneur, LLC 2024- 2026

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  • #36
    May 12 · 54 min

    Stop Planning. Start Building. (His Rule Will Challenge You) | Daniel Innovaté

    There's a new kind of builder emerging. 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. Daniel Innovaté on LinkedIn Idea Factory Agency 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. ⏱️ 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 #ParallelEntrepreneur #DanielInnovaté #AIBuilder #BuildWithAI #ShipFast #IdeaFactory #GeneralistAdvantage #MultipleVentures #BuildInPublic #FutureOfWork #AICollaboration #ProductDesign #FounderMindset #JustBuildIt #TechEntrepreneur #ImmigrantFounder #Resilience #Innovation #MarkCleveland #ParallelEntrepreneurPodcast © Parallel Entrepreneur, LLC 2024- 2026

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  • #35
    April 27 · 1 hr 8 min

    What It Really Takes to Build a Brand People Love | Andy Marshall

    Most people think they're building a business. 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: Puckett's Restaurant About Andy Marshall Andy Marshall on Facebook 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 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. Chapter: 00:00 "Son, you sound like an entrepreneur." — the moment that started it all 00:31 Welcome to the Parallel Entrepreneur — Season 2 intro 00:58 Who is Andy Marshall? Host introduction 01:50 Mark's first visit to Puckett's Grocery in Leapers Fork 02:22 Andy's origin story: selling soap, Sunday suppers, and his dad's words 04:25 Buying his first grocery store at 26 — and eventually selling four 05:43 Leapers Fork finds Andy: two gas pumps and an instinct 06:36 Cooking becomes the calling card — then music, then community 07:07 11 restaurants later: how do you keep the magic at scale? 07:46 Going from one to two: the duplicability question 09:35 Why Andy keeps choosing the hardest businesses 10:30 Passion over logic: following the entrepreneur instinct 11:40 "My dad taking me in" — mentorship and what that phrase really meant 12:12 Growing up: divorce, a stepfather, abuse, and learning to survive 16:13 Landing in Williamson County — the place that saved his life 17:12 How adversity became leadership: people skills forged by necessity 18:24 Adapting, reading people, and becoming a natural leader 20:03 Parallel vs. serial entrepreneurship — and why the difference matters 21:04 Superpower: sitting in the other person's chair 22:58 People just want to be heard 23:01 Boys & Girls Club, the Ed Moody Award, and giving back to youth 24:05 Understanding and leading the next generation of workers 27:09 Not everyone is the same — coaching, adaptive leadership, and bad eyesight 28:28 Family business: how Claire became president of A. Marshall Hospitality 30:20 Claire's path — from #1 MTSU graduate to company leader 31:14 Teaching Claire entrepreneurship through Hattie James Creamery 32:14 Dave Ramsey's advice, Claire's return, and succession clarity 33:21 The company's finances today: zero personal debt 33:56 Build a brand before you talk about a franchise 36:26 Coaching daughters, crossing the dad/coach line, and asking better questions 37:40 Emily and Cliff — the rest of the Marshall family in and out of the business 39:34 Williamson County's schools: the foundation of everything 40:21 The hat comes out — Andy is running for county mayor 41:11 Why now: 24 years of Rogers Anderson, and who comes next 43:49 Politics has gotten polarizing — but Andy's all in 44:14 The call to Bill Lee: "I can't think of anybody better" 46:49 Marsha Blackburn, Rogers Anderson, and the conversation that sealed it 49:15 Jenny's two-page letter — and the Bible study Andy wrote back 51:35 What Andy is most excited about: getting past the campaign 52:18 The hardest part: keyboard cowards and false narratives 53:34 Walking the county complex — hugs instead of handshakes 55:03 Public servants are vastly underappreciated 56:16 A lesson from an employee that stuck 56:44 The door-kicking moment: choosing not to become his stepfather 59:23 Grandfather's advice: learn from other people's mistakes 59:47 Advice for entrepreneurs scaling from one venture to two 01:00:09 Eight years of 3:30am biscuits — the real Leapers Fork grind 01:01:55 The New York Times writes it up — and suddenly locals care 01:02:27 The hardest truth about selling a company 01:05:10 What made Puckett's a brand: intentional vs. accidental 01:07:19 Building essential businesses — the community partnership model 01:07:50 Closing thoughts and outro #ParallelEntrepreneur #AndyMarshall #Puckets #AMarshallHospitality #WilliamsonCounty #WilliamsonCountyMayor #FamilyBusiness #ServantLeadership #BuildingABrand #HospitalityLeadership #Entrepreneurship #CommunityLeadership #BoysAndGirlsClub #Resilience #LegacyBuilding #NashvilleFood #FounderStory #BusinessPodcast #MarkCleveland #ParallelEntrepreneurPodcast © Parallel Entrepreneur, LLC 2024- 2026

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  • #34
    April 8 · 53 min

    Why Mentorship Is Broken (And How to Fix It) | Eve Peeterson

    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

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  • #33
    March 18 · 21 min

    Why Founders Don’t Succeed Alone | Dakota Simpson

    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

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  • #32
    March 11 · 6 min

    Operational Debt Is Slowing Your Company | Stephanie Johnson

    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

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  • #31
    March 4 · 10 min

    Strategic Alignment of Talent, Tech & Data | Amy Henderson

    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

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  • #30
    February 25 · 21 min

    Women in Tech, Real Relationships & Nashville’s Growth Story | Meg Chamblee

    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

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  • #29
    February 18 · 13 min

    Designing for Trust: Customer Experience, Bias & the Human–Automation Balance

    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

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  • #28
    February 11 · 17 min

    Why Today’s Leadership Playbook Breaks in the Age of AI

    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.

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  • #27
    February 4 · 16 min

    Why the Future of Entrepreneurship Starts in Schools | Dr. Jeremy Qualls

    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

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  • #26
    January 28 · 16 min

    Why AI Strategy Fails Before It Starts | Jon Hilton

    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

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  • #25
    January 21 · 11 min

    Stop Doing Tasks AI Can Handle: Shauna Sprague on Automation & Human Potential

    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™. 👉 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. #ShaunaSprague #ParallelEntrepreneur #InnovationSeries #AILeadership #PracticalAI #AIStrategy #Automation #AIForBusiness #FutureOfWork #HumanCenteredAI #InclusiveAI #DigitalTransformation #NashvilleTech #Entrepreneurship #LeadershipPodcast © Parallel Entrepreneur, LLC 2024- 2026

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