Best From The Basement To The Boardroom Podcasts (2025)

1
The Power of Curiosity: Carla Bailo on Smart Cities, Boardroom Wisdom, and Transforming Mobility 59:53

6d ago59:53

59:53

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 for Automotive Research and winning the USDOT Smart City Challenge for Columbus, Ohio. Carla shares stories of innovation, mentorship, boardroom leade…

1
Part 2 - Currency Chaos, AI Freedom & The Future of Value | Matthew Joynes 55:02

13d ago55:02

55:02

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 scaled it to $1 B+ in volume. • Why he calls Bitcoin “a collectible—like Beanie Babies” and predicts its slide back to reality. • Dollar dominance, tar…

1
Part 1 - AI Will Erase 20th Century – Parallel Entrepreneur Matthew Joynes on Money, Cap Tables & Super-AI 1:00:11

20d ago1:00:11

1:00:11

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) joins host Mark Cleveland to smash the china shop of old-school business. In this high-voltage conversation you’ll learn: ▸ Why Joynes says the real pr…

1
Start Paralleling: Mark Cleveland on Multiplying Your Impact 11:15

27d ago11:15

11:15

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 multiple passions run side‑by‑side so each fuels the next. Whether you’re a founder with five side projects, an artist‑parent, or a multipotentialite …

1
From Basement Startup to Global Brand: Tim Ozgener’s Parallel Journey 58:04

1M ago58:04

58:04

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 Arts, a cutting-edge contemporary arts hub in Nashville. Now launching Oz Family Cigars, Tim blends art, science, and storytelling into every venture.…

1
From EdTech to CyberTech: Justin’s Parallel Entrepreneur Path 1:08:47

1M ago1:08:47

1:08:47

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 frameworks, data risk, and that special systems-thinking spark that turns small wins into scalable success. Leveraging his EdTech expertise to tackle sec…

1
The Human Side of Hustle Ft Robert Hartline 1:00:38

2M ago1:00:38

1:00:38

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 brutal T-Mobile merger that forced him to shut down half his locations in months. In this candid episode of The Parallel Entrepreneur, Robert reveals …

1
Surviving to Serve: A Parallel Entrepreneur’s Comeback Ft Michael Sprintz 1:00:49

2M ago1:00:49

1:00:49

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 episode, Mark Cleveland welcomes Dr. Michael Sprintz, an anesthesiologist-turned-tech-entrepreneur tackling chronic pain, addiction, and complicated billing …

1
Mastering Leadership, AI, and Organizational Alignment Ft John Farkas 44:38

2M ago44:38

44:38

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 unlock growth-ready alignment. From creating synergy across different offerings to leading teams through high-stakes transformations, John shares real-worl…

1
From Startup to $90M Exit: Silas Deane on Innovation, Risk, and Resilience 51:54

2M ago51:54

51:54

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-changing fintech solution in an unlikely industry to executing a $90M exit without investors. If you’re ready to unlock the secrets of scaling, pivoting, …

1
Scaling Success: Leadership, Acquisitions, and Culture with John Cerasuolo 43:08

3M ago43:08

43:08

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-won lessons that propelled his journey from the Naval Academy to leading a thriving home services network. If you're a parallel entrepreneur looking t…

1
How Caitlin MacGregor is Unlocking Human Potential with Plum.io 1:08:17

3M ago1:08:17

1:08:17

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 MacGregor, CEO and Co-Founder of Plum, to talk about building a high-growth company while raising a family and defying the usual startup playbook. If you’r…

1
How Multipreneur Christian Paro Built the Coolest Co-Working Space in Nashville 40:35

3M ago40:35

40:35

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 in Nashville—and a new 49-acre trail-oriented development, featuring artist lofts. Hosted by Mark Cleveland, this episode of Parallel Entrepreneur expl…

1
The Journey of FreightWaves Ft Craig Fuller 1:08:40

3M ago1:08:40

1:08:40

In this episode of the Parallel Entrepreneur podcast, host Mark Cleveland interviews Craig Fuller, founder of FreightWaves, a pioneering company in the logistics and transportation sector. They discuss Craig's entrepreneurial journey, the innovative business model of FreightWaves, and the importance of real-time data in the freight industry. The co…

1
Small Ideas, Big Wins: Nitin Rai’s Blueprint for Multi-Venture Success 46:01

3M ago46:01

46:01

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 episode, host Mark Cleveland uncovers Nitin’s secrets to mastering delegation, cultivating mindful leadership, and building “small” ideas into life-changing …

1
Scale, Sell, Repeat: Roger Brown’s Playbook for Parallel Entrepreneurs 41:22

4M ago41:22

41:22

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 power-packed interview, Roger reveals how to create genuine value in a business (not just revenue), the art of spotting the right time to sell, and why …

1
Redefining Success Through Human-Centric Leadership Ft Jason Putnam 53:42

4M ago53:42

53:42

I’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 revolutionizing the talent space with psychometric data to build inclusive, thriving teams. In this conversation, we dive into: Why “failing fast” can s…

1
Bridging Passion and Purpose in Business Ft Francisco Gonzalez 41:11

4M ago41:11

41:11

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. Francisco shares his journey from early entrepreneurial experiences to founding Fearless Journeys, a community aimed at connecting aspiring entrepreneurs.…

1
Serial Exits & Roll-Ups: John McDonald’s M&A Roadmap for Parallel Entrepreneurs 1:03:10

4M ago1:03:10

1:03:10

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 and Senior Managing Director of Kensington Park Capital, who’s closed 300+ M&A transactions. John shares: Highlights: The biggest mistakes founders mak…

1
Building a Competitive Edge Ft Ania Rodriguez 42:18

5M ago42:18

42:18

Join me, Mark Cleveland, as I sit down with Ania Rodriguez, CEO & Founder of JourneyTrack.io, to discuss her journey as a serial entrepreneur and her mission to revolutionize customer experience. Ania shares her insights on building enterprise-grade SaaS platforms, raising capital as a female founder, and scaling multiple businesses simultaneously.…

1
Innovating Beyond Boundaries Ft William Klehm 1:00:06

6M ago1:00:06

1:00:06

In my very first episode, I sit down with visionary Parallel Entrepreneur, William Klehm, to unpack the lessons he learned from building, scaling, and selling multiple businesses. From spinning off a $28 billion asset at Ford Motor Company to leading groundbreaking startups in e-bikes and artificial intelligence, Bill shares his journey of innovati…

1
Welcome to the Parallel Entrepreneur Podcast with Mark Cleveland! 0:37

8M ago0:37

0:37

The Parallel Entrepreneur Podcast, hosted by Mark Cleveland, dives into the journeys, challenges, and insights of entrepreneurs who simultaneously manage multiple ventures. Through candid conversations, we uncover what drives these visionaries to juggle diverse enterprises, how they navigate risks and failures, and the lessons that have shaped thei…

1
Legends & Lore 42:23

10M ago42:23

42:23

Chapter 14 - In the aftermath of Lorraine's coup, Gary struggles to regain his footing. But as the years pass, and D&D’s popularity grows, Gary and Dave Arneson become folk heroes to a new generation of role playing gamers. From humble beginnings, their legacy endures.By Traction Media

1
Dispel Magic 49:19

10M ago49:19

49:19

Chapter 13 - While Gary moves to improve the company’s finances as its new CEO, President, and Board Chairman, a second battle gathers momentum. Unbeknownst to Gary, his worst and fiercest enemy has been lurking in the background, masquerading as his greatest ally.By Traction Media

1
Save or Die 49:00

10M ago49:00

49:00

Chapter 12 - Gary races back to Lake Geneva, dead-set on restoring his royalty payments. As retribution, Gary blames all the company’s failures on Kevin and convinces the Board to replace him. Kevin and Brian are out - but refuse to resign from the Board until TSR buys out their shares. With the help of a new ally, Gary outmaneuvers Kevin and Brian…

1
Ring of Delusion 49:36

10M ago49:36

49:36

Chapter 11 - Gary escapes to Hollywood, rents a mansion, and embraces a life of excess as he pursues movie and TV deals. Meanwhile, Kevin strategizes ways to limit the impact of Gary’s royalties on TSR. But Gary takes notice, and takes aim at Kevin.By Traction Media

1
Critical Hit 32:37

11M ago32:37

32:37

Chapter 10 - Gary, Brian, and Kevin are forced to reckon with the failures of over-expansion. Between the “Satanic Panic” and market saturation, sales of the game begin to plateau. Continued corporate mismanagement leads to a crisis that puts hundreds of people out of work and sends TSR into a tailspin. Gary’s marriage collapses.…

1
Rope of Entanglement 43:18

11M ago43:18

43:18

Chapter 9 - With Gary distracted, TSR’s lack of corporate leadership and vision creates a vacuum for Kevin Blume to assume even more control. What he lacks in experience, he makes up with confidence. Flush with money and the promise of future sales, Kevin, Brian, and Gary focus on acquisitions and ambitious expansion.…

1
Tomb of Horrors 47:29

11M ago47:29

47:29

Chapter 8 - As sales of D&D continue to skyrocket, tensions between the designers and upper management reach a boiling point. The employees turn to Gary for help, but find him missing in action. With his marriage on the rocks and exhausted by the company in-fighting, Gary looks for new opportunities to expand the D&D brand in Hollywood.…

1
The Snake Pit 47:56

11M ago47:56

47:56

Chapter 7 - New divisions emerge within the company. Gary’s camp includes his wife, his kids, and a cadre of executives and freelance designers known as “The Friends of Gary.” The Blume camp includes more than a dozen relatives and in-laws. The employees caught in the middle become cogs in a gaming factory, punching a clock at the direction of Kevi…

1
Satanic Panic 41:35

12M ago41:35

41:35

Chapter 6 - When James Dallas Egbert goes missing, the press and concerned parents start to question the influence D&D holds over impressionable young minds. As a result: the game explodes into the national consciousness and Gary Gygax becomes a multi-millionaire.By Traction Media

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Reaction Adjustment 49:47

12M ago49:47

49:47

Chapter 5 - To keep up with growing product demand, TSR hires a new crop of young designers, developers, and editors. Wages are low, but it’s a chance to work with their hero in a brand new industry. On the management side, Brian Blume's older brother Kevin joins the company and rises through the ranks.…

1
Creeping Doom 44:40

12M ago44:40

44:40

Chapter 4 - Gary Gygax and Brian Blume reassert control by instituting new company policies and focusing exclusively on D&D. Dave Arneson strikes out on his own, but struggles to match TSR's impressive growth. Just months after the company moves into a new headquarters at the former Hotel Clair, Arneson files suit against the company for attempting…

1
Decision Fatigue - Fake news? You Decide 48:01

2y ago48:01

48:01

Join our hosts Brett Hale, Taylor Lowe, and Ben Glathar uncovering the relationship between Cholula, radishes, and decision fatigue. The effects of decision fatigue are felt in our personal and work lives. This discussion targets the main symptoms of decision fatigue, including poor concentration, decreased willpower, and procrastination, drawing f…

1
Burnout - A sign that culture may be cracking 48:43

2y ago48:43

48:43

120,000 deaths are attributed to chronic stress each year[1]. This episode tackles the widespread issue of burnout in the workforce. Brett, Taylor, and Ben share personal narratives of their own burnout experiences and explore the societal implications and impact on productivity and overall well-being. The trio discusses necessary changes in work c…

1
Are Resumes Dead? ...please, it's time for a change. 1:00:02

2y ago1:00:02

1:00:02

Welcome to our latest episode, where we dive deep into a fascinating topic - the relevance and importance of resumes in today's job market. We explore the bold assertion that the traditional resume may be an outdated method of assessing job applicants. In this episode, we share our personal insights into the ever-stagnant job application process an…

1
Fight VUCA with VUCA: The new VUCA world 55:26

2y ago55:26

55:26

Operating in a VUCA (Volatile, Uncertain, Complex, and Ambiguous) world is this episode's topic. We explore how businesses can harness vision, understanding, collaboration, and action (VUCA 2.0) to thrive amidst turbulence. Navigate unprecedented challenges, with practical examples from the business arena. Whether a seasoned entrepreneur or a busin…

1
AI Apocalypse Team Selection 13:27

2y ago13:27

13:27

In a world where AI has run amok, you must assemble your "A" team to survive. Join our hosts in this bonus episode for their team selection. Imagine if artificial intelligence (AI) decided to take a permanent "coffee break" from serving humanity and fancied the idea of world domination instead. Like an overworked intern finally fed up with fetching…

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ChatGPT, AI, Humans – Oh my! - Part II 1:16:50

2y ago1:16:50

1:16:50

In the second part of Boardroom in the Basement podcast series "ChatGPT, AI, Humans - Oh My!", the discussion continues on the impact of AI and other emerging technologies on society, the workforce, and our daily lives. The speakers focus on the ethical concerns, potential benefits, and challenges posed by AI adoption. They highlight the importance…

1
ChatGPT, AI, Humans – Oh my! 1:02:43

2y ago1:02:43

1:02:43

Welcome to this episode of our podcast, part one of two-part series with hosts, Brett, Taylor, and Ben discussing the open letter calling for a halt to AI Labs' ChatGPT model training, and the concerns surrounding unchecked advancements in artificial intelligence. ChatGPT is everywhere in the news, social media, and businesses racing to adopt the t…

1
Who wouldn't want a four day workweek? 55:33

2y ago55:33

55:33

Welcome to this episode of our podcast, where hosts, Brett, Taylor, and Ben will be discussing the results of the largest study yet on the feasibility of a global 4-day workweek. Over the past few years, there has been a growing movement advocating for a shorter workweek as a way to improve work-life balance, boost productivity, and reduce burnout.…

1
Layoffs, layoffs, and more layoffs 1:03:11

2y ago1:03:11

1:03:11

You can't hide from the news dropping every week about layoffs. Why is this happening? Resources: https://knowledge.wharton.upenn.edu/article/the-cow-in-the-ditch-how-anne-mulcahy-rescued-xerox/By Brett Hale

1
System Shock 43:01

3y ago43:01

43:01

Chapter 3 – Seizing the momentum of D&D’s growing popularity, Gary and his partner Brian Blume press on with an investment from Brian’s father, Melvin. The company moves into a new headquarters and hires on friends from the Twin Cities and Lake Geneva. It looks like Camelot, but underneath the surface, grievances fester and friendships fracture. Th…

1
Detect Magic 40:58

3y ago40:58

40:58

Chapter 2 - In Minneapolis, a hive-mind of creative synergy reaches a critical mass with a game from Dave Arneson called “Blackmoor.” Convinced of its potential, Gygax and Arneson work furiously to develop the idea into what eventually becomes Dungeons & Dragons. But when he is unable to find a publisher for it, Gary and a childhood friend start th…

1
Eye of the Beholder 43:53

3y ago43:53

43:53

Chapter 1 - In the early 1960s, Gary and Mary Jo Gygax move their young family to Lake Geneva, Wisconsin to escape their urban life in Chicago,. Though he works as an insurance underwriter by day, Gary spends his nights and weekends as a central figure in a burgeoning community of wargame players seeking camaraderie and a distraction from a turbule…

1
Introduction - When We Were Wizards 1:25

3y ago1:25

1:25

WHEN WE WERE WIZARDS is a 14-episode documentary podcast that charts the rise and fall of Gary Gygax, the co-creator of the role-playing-game phenomenon Dungeons & Dragons and co-founder of the company that produced it, TSR Hobbies. It’s a story about the personal toll success can exact on friendships and families, especially when corrupted by gree…

1
Boob Talk 1:01:00

5y ago1:01:00

1:01:00

We discuss coping with stress & anxiety during the COVID 19 Pandemic using aromatherapy with special guest, Aromatherapy Specialist Stacey Halligan McCarthy and the benefits for cancer survivors. Also Survivor Spotlight with breast cancer survivor, Andraya Lombardi.By Survival Radio Network

1
The Paula G Show 1:06:00

5y ago1:06:00

1:06:00

Listen to The Paula G Show each week as we expand the mindset through world-wide conversations. Farewell Episode.By Survival Radio Network

1
Boob Talk 1:04:00

5y ago1:04:00

1:04:00

We discuss the benefits of Tea Therapy for Cancer survivors.By Survival Radio Network

1
The Paula G Show 1:03:00

5y ago1:03:00

1:03:00

Listen to The Paula G Show each week as we expand the mindset through world-wide conversations. Tune in this week: A full circle moment. Our very first guest Daneea Badio McCray joins us along with our very first engineer Mike Barnes.By Survival Radio Network

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