Cover of Parallel Entrepreneur with Mark Cleveland

Parallel Entrepreneur with Mark Cleveland

Parallel Entrepreneur with Mark Cleveland

By: Mark A. Cleveland
Listen for free

Season's Savings | 0.99 €/month for 3 months

5.99 €/month thereafter - terms apply. Cancel monthly.
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.© Parallel Entrepreneur, LLC 2026 Economics Leadership Management Management & Leadership
Episodes
  • What It Takes to Lead More Than One Business | Dr. Tobias Kutzewski

    What It Takes to Lead More Than One Business | Dr. Tobias Kutzewski
    1 Oct 2026
    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 entrepreneursIf you've ever been told you need to choose one business, one idea, or one path, this conversation offers another perspective.About Dr. Tobias KutzewskiDr. 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 LinkedIn𝗔𝗯𝗼𝘂𝘁 𝘁𝗵𝗲 𝗛𝗼𝘀𝘁Mark 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 LinkedInSubscribe 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 KutzewskiExplore Tobias's research at Vrije Universiteit AmsterdamUnlocking Strategic Innovation: Competitive Success in a Disruptive Environment — Surja Datta, Sandeep Roy & Tobias Kutzewski:Follow The Parallel Entrepreneur on LinkedInLearn more about Mark Cleveland:Happy OverallChapters:00:00 Are you already a parallel entrepreneur?01:59 What is strategic optionality?04:20 Recognizing vs. seizing opportunity07:20 Why Tobias began studying parallel entrepreneurs11:28 Parallel vs. serial entrepreneurship14:37 How Mark manages attention across multiple companies18:54 Finding and deploying the right talent21:26 Businesses at different stages of maturity22:27 Different types of parallel entrepreneurs25:09 Happy Overall26:16 Is entrepreneurship a game?29:44 When the rules suddenly change32:05 Mark's businesses during COVID-1933:36 Pause, pivot or pursue?35:25 How entrepreneurs make decisions under pressure38:17 Studying entrepreneurs through COVID-1941:37 Preparing for black swan events43:15 What makes some entrepreneurs more resilient?48:16 Mark's approach: observe, accept, act51:13 "Why on earth do you do more than one thing?"53:56 The economic impact of parallel entrepreneurs57:48 How big is parallel entrepreneurship?1:00:55 The next generation of parallel entrepreneurs
    Show more Show less
    41 min
  • The Science Behind Running Multiple Businesses at Once | Dr. Tobias Kutzewski

    The Science Behind Running Multiple Businesses at Once | Dr. Tobias Kutzewski
    10 Sep 2026
    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 entrepreneursIf you've ever been told you need to choose one business, one idea, or one path, this conversation offers another perspective.About Dr. Tobias KutzewskiDr. 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 LinkedIn𝗔𝗯𝗼𝘂𝘁 𝘁𝗵𝗲 𝗛𝗼𝘀𝘁Mark 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 LinkedInSubscribe 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 KutzewskiExplore Tobias's research at Vrije Universiteit AmsterdamUnlocking Strategic Innovation: Competitive Success in a Disruptive Environment — Surja Datta, Sandeep Roy & Tobias Kutzewski:Follow The Parallel Entrepreneur on LinkedInLearn 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 opportunity07:20 Why Tobias began studying parallel entrepreneurs11:28 Parallel vs. serial entrepreneurship14:37 How Mark manages attention across multiple companies18:54 Finding and deploying the right talent21:26 Businesses at different stages of maturity22:27 Different types of parallel entrepreneurs25:09 Happy Overall26:16 Is entrepreneurship a game?29:44 When the rules suddenly change32:05 Mark's businesses during COVID-1933:36 Pause, pivot or pursue?35:25 How entrepreneurs make decisions under pressure38:17 Studying entrepreneurs through COVID-1941:37 Preparing for black swan events43:15 What makes some entrepreneurs more resilient?48:16 Mark's approach: observe, accept, act51:13 "Why on earth do you do more than one thing?"53:56 The economic impact of parallel entrepreneurs57:48 How big is parallel entrepreneurship?1:00:55 The next generation of parallel entrepreneurs
    Show more Show less
    1 hr and 2 min
  • Fall in Love With the Problem, Not the Solution | Annie Cyr

    Fall in Love With the Problem, Not the Solution | Annie Cyr
    18 Aug 2026
    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 creators𝗔𝗯𝗼𝘂𝘁 𝗔𝗻𝗻𝗶𝗲 𝗖𝘆𝗿Annie 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 LinkedIn𝗟𝗶𝗻𝗸𝘀 & 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀:Tengiva:The Parallel Entrepreneur Podcast:Happy Overall:𝗔𝗯𝗼𝘂𝘁 𝘁𝗵𝗲 𝗛𝗼𝘀𝘁Mark 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 LinkedinChapters00:00 Fall in Love With the Problem01:05 How Annie Cyr Wrote the Book on Textiles02:57 The Knowledge You Can't Learn From a Book04:00 Why the Textile Industry Is So Complex06:26 Innovation vs. Disruption08:26 Why AI Won't Replace Human Expertise09:58 Choosing Which Problems to Solve First13:30 Modernizing a Protective Industry16:34 Annie's Superpower: Selling Without Selling19:46 Lessons Every Founder Can Use21:05 Learn With Other People's Money22:25 Happy Overall23:31 What Fundraising Taught Annie26:50 Stop Trying to Beat Your Competitors28:21 Hiring for Industry Experience31:19 What Annie Wants Tengiva to Accomplish32:52 Annie's Magic-Wand Vision for Textiles33:26 Making It Easier for New Brands to Start36:41 Is Work-Life Balance an Illusion?38:11 The Hospital Lesson That Changed Annie's Approach41:16 Knowing When to Stop42:42 Why Tengiva's Real Start Came in 202043:46 Raising Capital and What's Next44:34 Closing ThoughtsSubscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures.
    Show more Show less
    45 min
adbl_web_anon_alc_button_suppression_t1
No reviews yet