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Parallel Entrepreneur with Mark Cleveland

Mark A. Cleveland
Entrepreneurship
Parallel Entrepreneurship
Artificial Intelligence
Nashville
Leadership
Mergers and Acquisitions
Plum
Freightwaves
Business Ventures
Creative Synergies
Healthcare Technology
Venture Capital
Caitlin Macgregor
Human Potential
Customer Experience
Mentorship
Cybersecurity
AI Leadership
Nashville, United States
Work-Life Balance

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.

PublishesWeeklyEpisodes39Founded2 years ago
Number of ListenersCategories
ManagementBusinessEntrepreneurship

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Artwork for Parallel Entrepreneur

Latest Episodes

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 b... more

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 Capita... more

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 naturall... more

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 Marsha... more

Key Facts

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Recent Guests

Douglas Song
CEO, founder of Protos Capital
Protos Capital
Episode: Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song
Daniel Innovaté
Entrepreneur, photographer, AI developer, and brand creator
Independent entrepreneur; various ventures mentioned (e-comm, render.real estate, Folio Capital)
Episode: Stop Planning. Start Building. (His Rule Will Challenge You) | Daniel Innovaté
Andy Marshall
Founder of A. Marshall Hospitality, restaurateur and community leader
A. Marshall Hospitality
Episode: What It Really Takes to Build a Brand People Love | Andy Marshall
Eve Peeterson
Estonian strategy and transformation leader; founder of Leadrs.online
Leadrs.online / Enterprise Estonia (former)
Episode: Why Mentorship Is Broken (And How to Fix It) | Eve Peeterson
Dakota Simpson
Chief Program Officer at Nashville's Entrepreneur Center
Nashville Entrepreneur Center
Episode: Why Founders Don’t Succeed Alone | Dakota Simpson
Amy Henderson
Experienced executive who helps organizations drive enterprise growth by aligning talent, technology, and data
Episode: Strategic Alignment of Talent, Tech & Data | Amy Henderson
Meg Chamblee
Executive vice president at UDig, leader of Nashville office
UDig
Episode: Women in Tech, Real Relationships & Nashville’s Growth Story | Meg Chamblee
Suzi Earhart
Customer experience and organizational change executive
Episode: Designing for Trust: Customer Experience, Bias & the Human–Automation Balance
Amalia Goodwin
Global Managing Director of Adaptive Organizations at Slalom
Slalom
Episode: Why Today’s Leadership Playbook Breaks in the Age of AI

Host

Mark Cleveland
Host of the show and founder of the parallel-entrepreneur-focused brand.

Reviews

5.0 out of 5 stars from 59 ratings
  • Mark is the real deal

    Love this show and the idea of parallel entrepreneurship

    Apple Podcasts
    5
    earlyriserpro
    United States2 years ago
  • The best host!

    Mark Cleveland’s journey as a parallel entrepreneur really sets him up nicely to converse with entrepreneurs from a wide variety of fields. It’s amazing how he engages both listeners and his guests for some real instruction to all who are on their own entrepreneurial journeys!

    Apple Podcasts
    5
    fgonzalez1978
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Mark Cleveland's show consistently delivers actionable insights for parallel entrepreneurs.
Guests come from diverse sectors, offering practical frameworks for growth.
Strong emphasis on mentorship and community impact resonates with listeners.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song
Q: What signals make a company attractive for your model?
Fragmented industries with consolidation potential, a capable current management team, and a growth plan that includes organic growth plus selective acquisitions when aligned with the strategy.
Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song
Q: How do you approach risk and leverage in lower-middle-market deals?
We avoid over-leveraging, use conservative debt levels, and structure deals with contingencies such as earn-outs or seller notes to withstand shocks and preserve liquidity for growth.
What It Really Takes to Build a Brand People Love | Andy Marshall
Q: What advice would you give someone trying to grow from one venture to two or more?
Focus on building a brand first, ensure you can deliver reliable experiences, and use experiential value (people, community) to drive growth rather than chasing quick expansion or external financing.
What It Really Takes to Build a Brand People Love | Andy Marshall
Q: What leadership lessons did you carry from your difficult childhood into running multiple businesses?
He describes developing people skills, adaptability from moving between many schools, and a mindset of service and leadership that prioritizes listening, humility, and mentorship, which informed how he leads now.
Why Mentorship Is Broken (And How to Fix It) | Eve Peeterson
Q: How does leadership culture influence mentorship and employee retention?
Leadership sets the tone for culture; a toxic or unsupportive leadership style undermines mentorship and drives people away, while a supportive environment that values learning keeps talent and fosters ongoing development.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Parallel Entrepreneur

What is Parallel Entrepreneur about and what kind of topics does it cover?

This show features practical, hands-on conversations with entrepreneurs who juggle multiple ventures across industries. Episodes frequently explore topics like independent sponsorship, AI-enabled product development, brand building, and leadership that scales with growth. A standout aspect is the emphasis on community, mentorship, and ecosystem-building, often anchored in Nashville but with broad relevance to builders pursuing parallel entrepreneurship. Listeners can expect actionable frameworks, personal journeys, and real-world examples of turning ideas into durable, multi-venture impact. Potential guests and sponsors should note the show's consistent focus on growth, governance, and the human side of technology-driven expansion.

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Which podcasts are similar to Parallel Entrepreneur?

These podcasts share a similar audience with Parallel Entrepreneur:

1. Money Guy Show
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3. Craftsmen Online Podcast

How many episodes of Parallel Entrepreneur are there?

Parallel Entrepreneur launched 2 years ago and published 39 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Parallel Entrepreneur?

Recent guests on Parallel Entrepreneur include:

1. Douglas Song
2. Daniel Innovaté
3. Andy Marshall
4. Eve Peeterson
5. Dakota Simpson
6. Amy Henderson
7. Meg Chamblee
8. Suzi Earhart

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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