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 leadership, and the importance of building systems that serve every citizen.

Carla's bold curiosity and relentless learning has had great impact on transportation, public policy, and corporate governance. From deploying bus rapid transit in underserved neighborhoods to baking the perfect baguette, this episode celebrates the human side of engineering and entrepreneurship.

Chapters List:

00:00:00 – Introduction to Carla Bailo
00:01:00 – Carla's Impact on Cities and Roads
00:03:19 – Columbus Wins the Smart Cities Challenge
00:06:50 – Rethinking Mobility for Underserved Communities
00:10:13 – Logistics Innovation: Rickenbacker Middle-Mile Project
00:12:45 – A Flyer on the Door: Communication Gaps in Tech Projects
00:15:23 – Paralleling Transportation, Economic Access, and Planning
00:18:36 – Start Small, Learn Fast: Scaling Smart City Systems
00:21:24 – Asking Better Questions: Carla’s Mentoring Style
00:23:33 – Think in Seven Generations: Long-Term Urban Planning
00:25:58 – Carla on Joining Corporate Boards and Boardroom Roles
00:28:00 – Lessons from Her Father on Responsibility and Preparation
00:32:29 – Learning Upstream Oil & Gas Through Hands-On Curiosity
00:34:20 – CEO Oversight and Navigating Shifting Political Climates
00:37:22 – What Makes a Great Board and a Good CEO
00:40:55 – Mentoring Done Right: Listening and Mutual Learning
00:46:50 – Grandparent Wisdom and Generational Teaching
00:49:49 – The Joy of Embracing the Unknown
00:53:07 – Baking Baguettes & Balancing Curiosity with Relaxation
00:54:40 – Surviving as a Woman Engineer in the ‘70s and ‘80s
00:57:54 – Final Reflections: Making a Difference at Scale

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Carla Bailo, NACD.DC on LinkedIn - https://www.linkedin.com/in/carla-bailo-nacd-dc-604ba19/
• Smart Columbus - https://smartcolumbus.com/?utm_source=chatgpt.com
• US Department of Transportation’s Smart City Challenge - https://www.transportation.gov/briefing-room/us-department-transportation-announces-columbus-winner-unprecedented-40-million-smart
• Society of Automotive Engineers – https://www.sae.org/
• Automotive Women’s Alliance Foundation - https://awafoundation.org/
• The Road to the Top is Not on the Map: Conversations with Top Women of the Automotive Industry by Carla Bailo – https://www.amazon.com/Road-Top-Not-Map-Conversations/dp/0768000920
• The Road Forward: More Conversations with Top Women in the Automotive Industry by Carla Bailo – https://www.sae.org/publications/books/content/r-513/
• Women in Mobility Bundle by Carla Bailo - https://www.amazon.com/Women-Mobility-Bundle-Carla-author/dp/1468603574/

Enjoy this episode? Don't forget to like, subscribe, and share with fellow entrepreneurs! For more insights and to join our community, visit parallelentrepreneur.com.

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, tariffs as modern-day tribute, and the hidden mechanics of fiat liquidity.
• AI-driven disruption—from accountants to animation studios—and the rise of “one-person unicorns.”
• Freedom as America’s true currency, and how Gen-Z parallel entrepreneurs can seize the moment.

Stick around to the end for Matthew’s no-BS advice on patents, cap tables, and turning unused assets into new revenue with AI.

Show Notes:
Matthew Joynes – LinkedIn - https://www.linkedin.com/in/matthewjoynes
Gamevice - https://gamevice.com
LifeMed AI - https://lifemed.ai/
Pulley - https://pulley.com/
CompaniesHouse.gov (free UK company filings)

👉 Subscribe for more conversations that unleash potential everywhere.
🎧 Listen to the audio pod & get extras: https://theparallelentrepreneur.transistor.fm/
🚀 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/

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 product of your company is its share price
▸ How LifeMed AI replaces 90,000 manual billing jobs with 120 staff and a neural network
▸ The fatal cap-table mistakes that make a start-up “un-investable”
▸ Post-capitalist realities: one-person, billion-dollar AI companies, robot labor, 7-day weeks disappearing
▸ Practical first steps for founders—tokenization, options, warrants, “buying your own time,” and more

Chapters:

00:00:00 Matthew Joynes Show Teasers
00:00:26 Meet Matthew Joynes, “Apex” Parallel Entrepreneur
00:02:31 Why AI Will Rewrite History
00:09:29 The Fear (And Opportunity) in AI
00:12:27 From Blind to Seeing: AI As New Vision
00:13:30 Work, Creativity, and Post-Capitalism
00:15:54 Parallel Entrepreneurs as Creators
00:17:24 What Matthew’s Reading Now
00:18:50 Why Every Tech Founder Is Parallel
00:22:00 “Your Product Is Your Share Price”
00:25:32 Biggest Mistakes in Forming a Company
00:29:10 Turning Shares Into Currency
00:30:27 Building an Investable Cap Table
00:37:52 Competing With (And Eating) Yourself
00:38:45 AI As Your Personal Teacher
00:44:10 Follow Your Curiosity, Not Just Passion
00:49:30 Selling a Film With Just Script & Poster
00:52:20 AI Accelerates Every Creative Idea
00:56:55 Letting Go, Buying Your Own Time
00:57:30 Stop Spending on Others—Invest in Yourself
00:59:17 Teaser for Part Two

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Matthew Joynes – LinkedIn - https://www.linkedin.com/in/matthewjoynes
• Gamevice - https://gamevice.com
• Stolen (2012) - http://www.stolen-movie.com/
• Bullet (2014) - https://www.youtube.com/watch?v=tdF9Vcv4cCo
• I Am Soldier (2014) - https://www.youtube.com/watch?v=7LIqnkUl0zA
• Marmadue (2022) - https://scfilmsinternational.com/current-films-animation-titles/marmaduke-3d/
• Dragonkeeper (2024) - https://dragonkeepermovie.com/
• LifeMed AI - https://lifemed.ai/
• Pulley - https://pulley.com/
• Brendan Iribe - https://brendaniribe.com/
• Backbone One - https://playbackbone.com/

Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/

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 who refuses to “pick a lane,” this 15‑minute talk will give you:

• A new definition of success (alignment, not hustle)
• Real‑life examples from the Parallel Entrepreneur Network
• A 60‑second guided reflection you can do right now
• Practical prompts to weave business, art, family and growth into one powerful tapestry

Chapters:

00:00:00 Intro — What “parallel” really means
00:01:55 The origin of The Parallel Entrepreneur project
00:04:17 Case study: Caitlin MacGregor’s aligned life
00:07:08 Insight: The power of slowing down
00:09:40 When stillness feeds creativity
00:11:32 Paralleling vs. Pivoting
00:13:05 Guided reflection exercise
00:14:40 Final invitation + takeaways

Join the community:
https://ParallelEntrepreneur.com/

Subscribe for more talks & founder stories:
https://www.youtube.com/@ParallelEntrepreneur?sub_confirmation=1

Key Quotes
“Success isn’t in speeding up; it’s in letting every lane of your life feed the others.”
“When who you are shows up in everything you do, stress becomes spaciousness.”

Connect with Mark
• Twitter – https://twitter.com/MarkCleveland
• LinkedIn – https://www.linkedin.com/in/mark‑cleveland/
• Podcast – https://parallelentrepreneur.com/podcast

Connect with Creative Mornings
https://creativemornings.com/

Show Notes:

• Share and engage with this video on LinkedIn: Click here

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.

In this episode, he and Mark Cleveland explore:

• Following Your Heart: Why Tim chose cigars and contemporary art
• Improv & Entrepreneurship: Leveraging “Yes, And” to handle surprises & spark creativity
• Exiting at the Top: Inside the CAO sale, key lessons in valuation & deal structure
• Nonprofit vs. For-Profit: Contrasts in building teams, mission, and sustainability
• Staying Centered: Yoga, mindful scheduling, and choosing environments that fuel innovation

Parallel Entrepreneurs, subscribe now and tell us in the comments which Oz insight struck your fancy—was it engineering meets art, or harnessing improv in daily business?

Chapters List:

00:00:00 Meet Tim Ozgener: Nashville’s Multi-Passionate Unicorn
00:01:14 Why Follow Your Passions?
00:02:23 The Art & Science of Cigars
00:05:09 Improv Skills in Business
00:07:14 Launching OZ Arts: A Different Kind of Startup
00:09:22 The Power of Authentic Connection
00:12:13 Lessons from Dad: Engineering Meets Entrepreneurship
00:15:18 Time Management & Team Trust
00:19:00 Nonprofit vs. For-Profit: Contrasting Cultures
00:22:00 Building Global Distribution
00:29:08 The CAO Exit Story
00:37:14 Yoga, Flow & Mindful Entrepreneurship
00:42:00 Embracing Failure & Authenticity

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• CAO Cigars - https://www.caocigars.com/
• OZ Arts - https://www.ozartsnashville.org/
• Crowned Heads Cigars - https://www.crownedheads.com/
• Oz Family Cigars - https://ozfamilycigars.com/
• The Revenge of the Tipping Point: Overstories, Superspreaders, and the Rise of Social Engineering by Malcolm Gladwell - https://www.amazon.com/Revenge-Tipping-Point-Overstories-Superspreaders/dp/0316575801/
• Headway app - https://headwayapp.co/
• Art Basel - https://www.artbasel.com/
• Ken Cope Consulting, LLC - https://kencopeconsultingllc.com/

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 security compliance for billion-dollar enterprises, Justin’s story is a masterclass in spotting trends and executing effectively.

Key Highlights:

• Opportunity Filtering – The three questions Justin always asks before launching a new product.
• AI as Internal Auditor – How Strike Graph deploys large language models to verify compliance automagically.
• Co-Founder vs. Solo Act – Winning arguments for teamwork, board partnerships, and the joys of not going it alone.
• Music & Mental Health – Surprising ways that daily creative outlets (and old-school Ashtanga yoga) keep Justin’s energy fresh.

Ready to sharpen your parallel potential? Subscribe now and share which insight resonated most—AI? Mentoring? Or making that “hundredth monkey” leap?

Chapters List:

00:00:00 Introduction to Justin Beals and StrikeGraph
00:02:02 Spotting Opportunities: Three Key Questions
00:04:10 Building Strike Graph: Why Framework Matters
00:06:06 Understanding Risk in Entrepreneurship
00:08:19 Systems Thinking & Data Models
00:12:09 Trends in Cybersecurity and Business Impact
00:14:31 Surviving a Downturn: B2B SaaS Realities
00:16:18 Co-Founders & Good Investors
00:19:43 Leveraging AI in Cybersecurity
00:22:35 Mentoring & Measured Learning
00:27:25 Creativity and Leadership in Entrepreneurship
00:33:13 Lessons Learned in Business and Co-Founding
00:40:36 Navigating Change with Venture Backers
00:43:19 The Emotional Landscape of Collaboration
00:45:18 The Art of Flexibility in Leadership
00:46:20 Shifting Focus: From Sales to Strategic Partnerships
00:48:00 Scaling with Core Values
00:51:38 Identifying Aha Moments in Customer Experience
00:53:57 The Impact of AI on Business and Society
00:57:52 Empowerment through Creative Technology
00:01:05:47 The Future of AI Companions
00:01:08:21 Lessons from the Past: Advice for the Future
00:01:18:58 The Essence of AI and Poetry

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Secure Talk podcast - https://www.strikegraph.com/secure-talk-podcast
• StrikeGraph – https://www.strikegraph.com/
• Roundbox Global - https://roundbox.com/
• Koru - https://www.koru.global/
• Snow Crash by Neal Stephenson - https://en.wikipedia.org/wiki/Snow_Crash
• Zealot: The Life and Times of Jesus of Nazareth by Reza Aslan - https://www.amazon.com/ZEALOT-Life-Times-Jesus-Nazareth/dp/140006922X
• Europe Between the Oceans: 9000 BC – AD 1000 by Barry Cunliffe - https://www.amazon.com/Europe-Between-Oceans-9000-BC-AD/dp/0300170866
• The Three Body Problem by Liu Cixin - https://en.wikipedia.org/wiki/The_Three-Body_Problem_(novel)
• Hundredth Monkey Effect - https://en.wikipedia.org/wiki/Hundredth_monkey_effect

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 why he believes in dancing through chaos, harnessing AI for decisions, and leading from a place of love.

Key Highlights:

• Secrets of a $100M Scale – How Robert powered up his cell phone stores with EOS and big-picture “why.”
• Dark Night of the Merger – The day Google listings vanished, store traffic plummeted, and Robert sold to survive.
• Harnessing AI as "Idea Manager" – Why we should treat AI like a creative partner, not a threat.
• Mindset & Breathwork – Tools Robert swears by to stay calm, refocus, and unlock “superhero energy.”
• The Clark Kent vs. Superman Moment – Overcoming shame, embracing authenticity, and letting your real self shine.

If you’re juggling multiple ventures—or dreaming of it—hit Subscribe and share in the comments which breathwork or AI tip resonates most with you!

Chapters List:

00:00:00 Introduction to Robert Hartline
00:00:47 Scaling to $100M & EOS Discipline
00:03:01 How Robert Reframes to Discover His “Why”
00:08:38 The T-Mobile Merger: From Momentum to Meltdown
00:14:20 Darkness, Divorce, and Post-Merger Fallout
00:19:45 The COVID Mask Pivot & Parallel Entrepreneurship Gone Wild
00:23:49 AI as Your “Idea Manager”
00:27:40 The Energy of Connection and Creation
00:30:12 How to Flow: Add Love, Breath & Movement
00:32:43 Unique Ability and the Power of Community
00:34:56 Discovering Your Why and Core Values
00:37:16 The Role of Love in Business and Life
00:40:00 Clark Kent vs. Superman: Embracing Your True Self
00:42:46 AI as a Decision-Making Tool
00:50:07 Energy Management and Personal Practices
00:52:17 The Biggest Gift Ever & the Future
00:54:56 Slowing Down to Speed Up
00:58:15 Wrap-Up & Gratitude

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• The Decision Experience - https://thedecisionexperience.com/
• Entrepreneurial Operating System (EOS) - https://www.eosworldwide.com/
• Soma Breath Guided Breathwork Training and Certification- https://www.somabreath.com/
• Wim Hoff Breathing - https://www.wimhofmethod.com/breathing-exercises
• Strategic Coach by Dan Sullivan - https://www.strategiccoach.com/book-a-call
• Traction: Get a Grip on Your Business by Gino Wickman - https://www.eosworldwide.com/traction-book
• Driven: Understanding and Harnessing the Genetic Gifts Shared by Entrepreneurs, Navy Seals, Pro Athletes, and Maybe You by Douglas Brackmann and Randy Kelley - https://www.iamdriven.com/
• 10x Is Easier Than 2X: How World-Class Entrepreneurs Achieve More by Doing Less by Dan Sullivan and Benjamin Hardy - https://10xeasierbook.com/
• The Three Marriages: Reimaging Work, Self and Relationship by David Whyte - https://davidwhyte.com/store/book/the-three-marriages/
• Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert - https://www.elizabethgilbert.com/books/big-magic/
• CallProof, sales tracking app - https://callproof.com/