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.
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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.
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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