Parallel Entrepreneur with Mark Cleveland

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

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

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.

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.

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

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

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

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

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

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