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Parallel Entrepreneur with Mark Cleveland - Podcast

Parallel Entrepreneur with Mark 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.

Innovation Entrepreneurship Inspiration Management Business Leadership Growth Success Mindset Creativity
Update frequency
every 6 days
Average duration
50 minutes
Episodes
23
Years Active
2024 - 2025
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Michael Built a Cybersecurity Empire—Then Let Competitors Use His Tools

Michael Built a Cybersecurity Empire—Then Let Competitors Use His Tools

What happens when a cybersecurity veteran automates the work his competitors still struggle to deliver? He builds the future—and lets them use it.

Michael Peters is a rare kind of founder: one who lea…

00:53:11  |   Thu 22 May 2025
The Power of Curiosity: Carla Bailo on Smart Cities, Boardroom Wisdom, and Transforming Mobility

The Power of Curiosity: Carla Bailo on Smart Cities, Boardroom Wisdom, and Transforming Mobility

In this episode of The Parallel Entrepreneur, Mark Cleveland welcomes Carla Bailo—an industry visionary who’s helped shape the future of mobility, from General Motors and Nissan to leading the Center…

00:59:53  |   Thu 15 May 2025
Part 2 - Currency Chaos, AI Freedom & The Future of Value | Matthew Joynes

Part 2 - Currency Chaos, AI Freedom & The Future of Value | Matthew Joynes

Welcome back to The Parallel Entrepreneur for part 2 with British-American polymath Matthew Joynes.

In this fast-paced sequel we dive into:

• How Matthew rescued a bankrupt currency-trading firm and s…

00:55:02  |   Thu 08 May 2025
Part 1 - AI Will Erase 20th Century – Parallel Entrepreneur Matthew Joynes on Money, Cap Tables & Super-AI

Part 1 - AI Will Erase 20th Century – Parallel Entrepreneur Matthew Joynes on Money, Cap Tables & Super-AI

What happens when super-AI makes lawyers, accountants—and even capitalism—obsolete?
British-American “apex” parallel entrepreneur Matthew Joynes (PGA producer, GameVice inventor, LifeMed AI founder) j…

01:00:11  |   Thu 01 May 2025
Start Paralleling: Mark Cleveland on Multiplying Your Impact

Start Paralleling: Mark Cleveland on Multiplying Your Impact

Stop juggling. Start PARALLELING.

Entrepreneur, community‑builder and podcast host Mark Cleveland takes the Creative Mornings stage to share why the future belongs to parallel thinkers—people who let…

00:11:15  |   Thu 24 Apr 2025
From Basement Startup to Global Brand: Tim Ozgener’s Parallel Journey

From Basement Startup to Global Brand: Tim Ozgener’s Parallel Journey

Looking for inspiration on juggling multiple business passions? Tim Ozgener might just be your blueprint. He helped take CAO Cigars from a basement startup to a global best-seller and then founded OZ…

00:58:04  |   Thu 17 Apr 2025
From EdTech to CyberTech: Justin’s Parallel Entrepreneur Path

From EdTech to CyberTech: Justin’s Parallel Entrepreneur Path

AI and security compliance could make or break your next venture. In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Justin Beals, co-founder of Strike Graph, to dive into fr…

01:08:47  |   Thu 10 Apr 2025
The Human Side of Hustle Ft Robert Hartline

The Human Side of Hustle Ft Robert Hartline

What happens when a merger you can't control threatens to destroy your 22-year business overnight? Meet Robert Hartline—parallel founder who scaled his wireless stores to $100 million, only to face a…

01:00:38  |   Thu 03 Apr 2025
Surviving to Serve: A Parallel Entrepreneur’s Comeback Ft Dr. Michael Sprintz

Surviving to Serve: A Parallel Entrepreneur’s Comeback Ft Dr. Michael Sprintz

How do you launch a thriving medical practice, then pivot to a fast-scaling software startup—all while staying laser-focused on patient care, personal growth, and 24 years in recovery? In this episod…

01:00:49  |   Thu 27 Mar 2025
Mastering Leadership, AI, and Organizational Alignment Ft John Farkas

Mastering Leadership, AI, and Organizational Alignment Ft John Farkas

Wondering how to nurture alignment throughout M&A integration?  In this episode John Farkas, founder of Ratio and Candor—two companies that help businesses master M&A integration—discusses how to unl…

00:44:38  |   Thu 20 Mar 2025
From Startup to $90M Exit: Silas Deane on Innovation, Risk, and Resilience

From Startup to $90M Exit: Silas Deane on Innovation, Risk, and Resilience

Are you a serial entrepreneur juggling multiple ventures and hungry for breakthrough growth? In this candid conversation, Silas Deane reveals his battle-tested blueprint—from bootstrapping a game-cha…

00:51:54  |   Thu 13 Mar 2025
Scaling Success: Leadership, Acquisitions, and Culture with John Cerasuolo

Scaling Success: Leadership, Acquisitions, and Culture with John Cerasuolo

Unlock the secrets of building an acquisition empire from someone who's done it well. In this exclusive interview, John Cerasuolo, CEO of Leap Partners, reveals the unconventional strategies and hard…

00:43:08  |   Thu 06 Mar 2025
How Caitlin MacGregor is Unlocking Human Potential with Plum.io

How Caitlin MacGregor is Unlocking Human Potential with Plum.io

Ready to discover how to hire for potential rather than past credentials—and why it could transform your business?

In this episode of Parallel Entrepreneur, Mark Cleveland sits down with Caitlin MacG…

01:08:17  |   Thu 27 Feb 2025
How Multipreneur Christian Paro Built the Coolest Co-Working Space in Nashville

How Multipreneur Christian Paro Built the Coolest Co-Working Space in Nashville

Get ready for a masterclass in multi-venture entrepreneurship from Christian Paro, founder of Center 615, Studio 615, Five Points Alley Shops—three of the most dynamic co-working and creative spaces …

00:40:35  |   Thu 20 Feb 2025
The Journey of FreightWaves Ft Craig Fuller

The Journey of FreightWaves Ft Craig Fuller

Ready to master the art of running multiple ventures without losing your sanity—or your shirt? Join host Mark Cleveland and Craig Fuller, the pioneering founder of FreightWaves, as they rip open the …

01:08:40  |   Thu 13 Feb 2025
Small Ideas, Big Wins: Nitin Rai’s Blueprint for Multi-Venture Success

Small Ideas, Big Wins: Nitin Rai’s Blueprint for Multi-Venture Success

How do you juggle multiple ventures and keep your cool under pressure? Meet Nitin Rai — seasoned founder, investor in 70+ startups, and champion of underrepresented talent. In this eye-opening episod…

00:46:01  |   Thu 06 Feb 2025
Scale, Sell, Repeat: Roger Brown’s Playbook for Parallel Entrepreneurs

Scale, Sell, Repeat: Roger Brown’s Playbook for Parallel Entrepreneurs

How do you scale, sell, and still come back for more? Meet Roger Brown — a serial founder who’s built (and exited) four different ventures, from physician services to cannabis testing labs. In this p…

00:41:22  |   Thu 30 Jan 2025
Redefining Success Through Human-Centric Leadership Ft Jason Putnam

Redefining Success Through Human-Centric Leadership Ft Jason Putnam

’m joined by Jason Putnam, a two-time award-winning executive (Globee Executive of the Year, Silver Stevie Award) and a 2024 Inspiring Leader. Jason’s the Chief Revenue Officer at Plum, where he’s re…

00:53:42  |   Thu 23 Jan 2025
Bridging Passion and Purpose in Business Ft Francisco Gonzalez

Bridging Passion and Purpose in Business Ft Francisco Gonzalez

In this engaging conversation, Mark Cleveland and Francisco Gonzalez explore the essence of entrepreneurship, focusing on the importance of community, mentorship, and the entrepreneurial mindset.

Fra…

00:41:11  |   Thu 16 Jan 2025
Serial Exits & Roll-Ups: John McDonald’s M&A Roadmap for Parallel Entrepreneurs

Serial Exits & Roll-Ups: John McDonald’s M&A Roadmap for Parallel Entrepreneurs

How do you build a company that buyers can’t wait to acquire—and still keep your entrepreneurial spark alive? In this episode of The Parallel Entrepreneur, we sit down with John McDonald, Co-Founder …

01:03:10  |   Thu 09 Jan 2025
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