Parallel Entrepreneur with Mark Cleveland

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 structures in healthcare. Dr. Sprintz shares how resiliency, authentic leadership, and “flow” guide his parallel ventures.

Highlights:

• From OR to Revenue Tech – Why Michael traded the surgical suite for software code.
• 24 Years Sober – How recovery principles shape his resilience in business.
• Nail Compliance, Stop Revenue Bleed – The healthcare billing problem Michael solves.
• Mindset Hacks – Handling stress, negativity, and “the shadow self” with unshakable resolve.
• Chasing Flow – Moving from “hustle 24/7” to deeper creativity and real presence.

Chapters List:

00:00:00 The Journey of Dr. Michael Sprintz
00:01:45 Resilience and Tenacity in Recovery
00:04:27 The Intersection of Pain and Addiction
00:06:40 Lessons from Entrepreneurship
00:09:00 Aligning Vision and Values
00:10:39 The Birth of Solarian
00:13:21 Navigating the Software Landscape
00:14:08 The Role of AI in Healthcare
00:16:13 Market Response and Growth Strategies
00:18:14 The Art of Adaptation
00:20:07 Authenticity in Business
00:22:08 Future Aspirations and Innovations
00:24:48 Best Advice Received: What you sell your company is not what you created at first
00:28:52 Helping Others See Beyond Their Current Reality
00:29:53 Understanding the Opioid Crisis and Healthcare Misalignment
00:32:45 Balancing Stress and Personal Life as a CEO
00:34:13 Time Management and Effective Communication
00:35:56 Lessons from Life and Death Experiences
00:37:43 Finding Meaning and Making Ethical Decisions
00:39:37 Embracing Technology and Uncertainty in Healthcare
00:41:27 Reflecting on Past Accomplishments and Future Risks
00:42:55 Living Life with No Regrets
00:43:55 The Impact of Literature on Personal Growth
00:45:14 The Connection Between Humanity and Business
00:52:44 Art, Music, and the Flow of Life
00:57:13 Trusting the Process and Letting Go

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• Cellarian Inc., healthcare software that improves diagnosis, treatment, documentation and risk-management for substance use disorder and other diseases - https://www.cellarian.com/ 
• A Life of Meaning: Relocating Your Center of Spiritual Gravity by James Hollis - https://jameshollis.net/hollisBooks.html 
• Living with Borrowed Dust: Reflections on Life, Love and Other Grievances by James Hollis - https://jameshollis.net/hollisBooks.html 
• The Alchemist by Paulo Coelho – https://www.amazon.com/Alchemist-Paulo-Coelho/dp/0062315005/ 
• Never Split the Difference: Negotiating As If Your Life Depended on It by Chris Voss – https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805 
• Mark’s 2025 Bhavana – https://www.youtube.com/watch?v=twS9UpeqeF0 

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-world lessons on balancing purpose with performance, leveraging “context switching,” and staying ahead of rapid market shifts.

Highlights:

• Parallel Mindset – John runs two consultancies that fuel each other.
• M&A Mastery – Turning chaotic post-acquisition phases into opportunities for deeper alignment.
• Keeping Pace with Change – Simple practices to handle lightning-fast market shifts without burning out.
• AI & the Future – How advanced tech is reshaping value propositions—and why you need to adapt now.
• Leading with Love – The surprising “sticky note” that guides John’s leadership style.

Chapters List:

00:00:00 Meet Organizational Alignment Guru John Farkas
00:02:08 Taming Chaos: Context Switching Across Industries
00:05:17 Birth of Candor: Solving the "Alignment" Dilemma
00:07:20 Understanding Organizational Alignment
00:09:13 Overcoming Fear & Building Trust in Organizational Change
00:11:29 Pace Paradox: Thriving in Accelerating Markets
00:13:46 Flattened Org Charts & Shared Objectives
00:16:02 The Impact of AI on Business Models
00:18:26 Spectacular Failures & Lessons Learned
00:20:37 The Mentoring Gap & Real Team Building
00:22:52 How do you manage time and energy between ventures
00:23:43 Superpowers: Context Switching & Listening
00:26:42 Self-Care & the Importance of Loving Leadership
00:30:16 M&A and Human Capital: Missing the Biggest Asset
00:34:19 Facing an AI-Driven Future
00:39:38 Rapid Fire: North Star, Books, Gifts & Wise Words
00:43:38 Closing Thoughts: Curiosity, Intent, and Love

Show Notes:

• Ratio, a growth marketing consultancy helping B2B healthtech and fintech companies - https://goratio.com/ 
• Candor, a growth architecture firm - https://www.candorgrowth.com/ 
• 99% Invisible podcast - https://99percentinvisible.org/ 
• The Power Broker by Robert Caro - https://99percentinvisible.org/club/ 
• Conclave by Robert Harris - https://www.amazon.com/Conclave-novel-Robert-Harris/dp/1101972904
• John's "walk on" song - Beautiful Day by U2

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, and innovating across diverse markets, this episode is your must-watch playbook.

Highlights include:

• How Silas bootstrapped VendEngine from idea to digital disruption
• An innovative approach to transforming inmate financial transactions
• Scaling strategies that grew the business from county jails to 425 facilities
• Merging startup agility with corporate synergy at Tyler Technologies
• Critical lessons on embracing failure, pivoting, and mastering time management
• Leadership insights on integrity, mentorship, and building winning teams
• The mindset behind taking calculated risks and seizing future opportunities, including AI trends

Chapters:

00:01:00 Introduction: Bootstrapping & Exiting with Silas Deane
00:02:56 VendEngine's Genesis: Innovating Inmate Transactions
00:04:32 Transforming the Inmate Payment System
00:07:27 Scaling Success: From County Jails to 425 Facilities
00:11:13 Corporate Synergy & Strategic Growth: Acquisitions & Hardware Innovation
00:16:09 Finding Synergies and Growth Opportunities
00:17:14 Learning Through Failure: Time Management & the Power of Pivoting
00:21:32 Leadership in Action: Integrity, Mentorship & Government Insights
00:24:46 Overcoming Financial Hurdles: Hustling to a $90M Exit
00:29:09 The Journey of a Parallel Entrepreneur 
00:32:21 Learning from Mistakes and the Freedom of a Clean Slate 
00:34:29 Feeding the Creative Drive 
00:36:26 The Power of Historical Insights and Identifying Patterns 
00:39:08 The Importance of Business Basics 
00:40:19 Discovering and Nurturing Talent 
00:41:45 Turning Mistakes into Learning Opportunities
00:46:25 Advice to My Younger Self 
00:48:14 The Nature of Risk in Entrepreneurship 
00:50:18 The Value of a Large Addressable Market

Show Notes:

• Share and engage with this interview on LinkedIn: LinkedIn post
• VendEngine Inc.
• Tyler Technologies (NYSE:TYL)
• KPMG
• Deane/Smith & Partners, a Nashville-based marketing and advertising agency
• NIC transaction management solution
• University of Kentucky, Gatton College of Business and Economics, Von Allmen Center for Entrepreneurship
• Junior Achievement of Middle Tennessee
• The Power of Broke by Daymond John

#ParallelEntrepreneur #SilasDean #VendEngine #90MillionExit #FintechFounder #Bootstrapped #TylerTechnologies #BusinessExit #SerialEntrepreneur #Innovation #ScalingUp #MarkCleveland #ParallelEntrepreneurPodcast #BusinessPodcast #StartupSuccess

© Parallel Entrepreneur, LLC 2024–2026

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 to scale or dreaming of launching your own network, this conversation is your blueprint for success.

Highlights include:

• His transformative journey from the Naval Academy to leading a multipreneur empire
• How Leap Partners was born out of a shared vision and 45+ acquisition successes
• Proven strategies for identifying quality businesses and integrating diverse cultures
• Lessons learned from early exits and the importance of “begin with the end in mind”
• The secret to balancing rapid growth, due diligence, and celebrating success
• Insights on building a people-first, family-centric company culture
• Rapid-fire insights on must-read books and what fuels his day-to-day drive

Whether you're running multiple businesses or planning your next big leap, this conversation is packed with actionable wisdom for every ambitious entrepreneur.

Chapters List:

00:01:00 Introduction to John Cerasuolo and Leap Partners
00:02:06 Naval Academy: Forging a Leader
00:04:09 Leap Partners Genesis: From ADS Security to Home Services
00:08:31 Identifying Acquisition Opportunities
00:11:05 Integrating Cultures in Acquisitions
00:14:36 Exiting with Great M&A Advisors
00:18:17 Challenges in Due Diligence
00:20:07 Celebrating Success
00:23:03 Mindfulness and Daily Practices
00:24:18 Advice to His Younger Self
00:26:08 Learning from Each Other in Business
00:27:15 Navigating Talent Challenges in the Trades
00:29:21 Rapid Fire Insights
00:32:20 Recognition and Awards
00:33:03 Scaling a Culture of Happiness
00:34:20 Modeling Leadership Behavior
00:35:22 A Day in the Life of a CEO
00:36:48 Choosing the Right Financial Partners
00:38:09 Surrounding Yourself with Talent
00:39:22 Books that Inspire
00:40:21 Closing Thoughts on Life and Business

Show Notes:

• Leap Partners, a Family of Service Companies - https://www.theleappartners.com/ 
• Fossil Future by Alex Epstein - https://www.forbes.com/sites/johntamny/2022/09/29/book-review-alex-epsteins-excellent-and-essential-fossil-future/ 
• Atlas Shrugged by Ayn Rand - https://aynrand.org/novels/atlas-shrugged/ 
• Joe Scarlett, former President and Chairman of Tractor Supply Company - https://joescarlett.com/ 

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’re juggling multiple ventures—or planning to—Caitlin’s journey will inspire you to embrace change, experiment with collaboration, and double down on what really drives success.

Highlights:

• Power Couple: Why being married to her co-founder is Caitlin’s superpower (despite investor skepticism).
• 13 Years of Growth: Balancing fundraising with customer-driven revenue, and why sales might matter more than venture capital.
• People Over Résumés: How Plum’s behavioral data approach uncovers “diamonds in the rough” for any role.
• Authentic Leadership: Leading with love, care, and collaboration to break down silos and foster real engagement.
• GenAI & the Future: Why tasks, not jobs, are being automated—and how to reinvent your organization for exponential success.

Don’t miss these candid insights from a founder who’s rewriting the rules on entrepreneurship and talent strategy.

Chapters List:

00:00:56 Meet Caitlin MacGregor: Founder, CEO & Human Potential Champion
00:02:44 When Your Co-Founder Is Your Spouse
00:05:08 Growing a Family & a Company Simultaneously
00:09:21 Fundraising Lessons: 99 No’s for 1 Yes
00:15:17 Rethinking Growth in a Shifting Market
00:17:30 Why Sales Might Matter More Than Fundraising
00:20:48 Integrating Feminine Dimensions of Leadership
00:25:16 Symbiotic Health - the New Model for Business Success
00:26:51 Well-being, Mindfulness & Self-Awareness
00:31:06 The Science of Unlocking Human Potential
00:35:00 Hire for Behaviors, Not Resumes
00:35:57 The Collaborative Operating System: Eliminating Silos
00:38:48 Perfection vs Collaborative Creation
00:45:42 Transforming Company Culture to Eliminate Politics
00:48:00 A Hiring Experiment That Sparked Plum
00:52:18 Advice for Future Generations
00:57:07 GenAI & the Future of Work
00:59:55 Books, Escapes & Art
01:04:53 The Future of Change Management

Show Notes:

• Plum, a revolutionary talent platform - https://www.plum.io/  
• EY Entrepreneurial Winning Women - https://www.ey.com/en_us/entrepreneurial-winning-women-north-america/class-of-2024  
• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman - https://www.blitzscaling.com/
• Bo Burlingham - https://boburlingham.com/
• The Revenue Engine: Fueling a B2B High Octane Pipeline by Kara Smith Brown - https://therevenueengine.com/
• The Fourth Wing by Rebecca Yarros - https://rebeccayarros.com/fourthwing

About Plum:

Dive into a fresh take on talent strategy with Plum, the durable skills company. Our robust talent assessment platform, PlumThrive, helps you harness the lasting impact of the core competencies that matter. By focusing on durable skills, we transform your company into a skills-based powerhouse, allowing you to make better talent decisions across the employee journey.

Are you ready to boost your hiring precision and extend employee tenure? Explore PlumThrive and transform your workforce strategy today: https://www.plum.io/book-demo

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 explores how Christian turned a park-management background into a cutting-edge real estate empire that thrives on community, collaboration, and creativity.

What You’ll Learn:

• Banker Skepticism → Big Vision: How Christian overcame early financing doubts to build Nashville’s go-to coworking hub.
• The Power of Celebration: Why throwing parties and embracing small wins keeps your team and tenants inspired.
• Mindful Pauses & Ping Pong: Christian’s secret to staying calm under pressure (including his favorite “reset” technique).
• Mentoring vs. Micromanaging: How giving autonomy attracts long-term staff and nurtures a vibrant entrepreneurial ecosystem.
• Expanding Into Events & Arts: From a single building to 49 acres of innovation—Christian’s massive new development plan.

Chapters List:

00:00:00 Meet Christian Paro: The Man Behind Nashville's Most Innovative Collaboration Spaces
00:01:28 From NYU Parks & Rec to Property Investor
00:03:06 Discovering Coworking: The Birth of Center 615
00:05:19 Banking Skepticism & the Power of Relationships
00:08:29 Studio 615: Expanding into Creative Production Spaces
00:12:05 Patterns, Parties & Parallel Lessons
00:13:48 Biggest Lessons & Avoiding Over-Leverage
00:14:54 Mentoring, Not Micromanaging
00:16:32 Mindfulness Practices & the Entrepreneurial Journey
00:22:13 Designing a New 49-Acre Community
00:24:13 Mindful Pauses: Staying Centered Under Pressure
00:27:25 Rapid Fire Insights: Gifts, Mantras, Books & Jedi Wisdom
00:32:36 Do What Scares You
00:37:12 Facing Fears & Final Thoughts

Show Notes:

• Share and engage with this interview on LinkedIn: Click here
• C615, a driving force in building and shaping community in Nashville - https://c615.co/
• Artist Sergey Gordienko (the art behind Mark) - https://www.instagram.com/dowhatyoulove.artist/
• Joanna Barbera, Nashville Musician and Mindfulness Mentor - https://www.joannabarbera.com/
• 8 Decisions (Conscious Entrepreneur Tribe) by Robert Hartline - https://8decisions.com/
• Nasty Girl by Iglesias - https://open.spotify.com/track/5MghBTWUogtorQqmKBwaBn
• All about Love: New Visions by Bell Hooks - https://www.amazon.com/All-About-Love-New-Visions/dp/0060959479
• The Optimist by Sophie Kipner – https://www.amazon.com/Optimist-Sophie-Kipner-author/dp/1783525584 
• The Madness of Crowds: A Novel by Louise Penny - https://www.gamacheseries.com/books/the-madness-of-crowds/
• Do One Thing Every Day That Scares You: A Journal - https://www.amazon.com/One-Thing-Every-That-Scares/dp/0385345771
• “Jenny’s Answer (867-5309)” female empowerment parody song by Jenny Pruitt - https://www.youtube.com/watch?v=qi2Ru6vvZo0
• Tiny Happy Things: Poems by Jenny Pruitt - https://www.amazon.com/Tiny-Happy-Things-Jenny-Pruitt/dp/B0DLD78L24

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 playbook on “Parallel Entrepreneurship.” From launching data-driven freight tech to buying iconic media brands—and even building an aviation empire—Craig spills the secrets behind owning your audience, harnessing AI for growth, and seizing opportunities most people miss. If you’re tired of thinking small and ready to multiply your wins, this episode is your ultimate roadmap.

What You’ll Learn:

• How to leverage distribution (and why it’s everything)
• Turning media audiences into profit engines
• When boredom is more dangerous than burnout
• Using AI to supercharge content creation and customer engagement
• The power of small, strategic M&A deals for explosive growth

Hit play and discover how to “Focus Less, Explore More” so you can scale your impact across industries—on your own terms.

Timestamps:

00:00:51 Introduction to Craig Fuller and FreightWaves
00:01:50 Revolutionizing Transportation with Data
00:03:40 The Business Model of FreightWaves
00:05:12 From Futures to Transparency in Trucking
00:06:46 The Bloomberg Inspiration for FreightWaves
00:11:56 Pursuing Opportunities to Drive Top of Funnel
00:18:45 Motivating Teams and Sharing Value
00:21:20 Finding Inspiration and Avoiding Burnout
00:26:29 Current Trends in the Transportation Market
00:34:04 Harnessing AI for Enhanced Content Creation
00:39:58 AI's Role in Customer Engagement
00:41:54 Evaluating Business Opportunities
00:42:56 The Importance of Distribution in Business
00:47:22 Asymmetric Risk and Business Strategy
00:50:10 Learning from Experience and Testing
00:56:58 The Journey vs. Destination in Entrepreneurship
01:02:37 The Value of Shared Experiences in Business

Show notes: 

• Share and engage with this interview on LinkedIn: Click here
• Bloomberg by Bloomberg - https://www.bloombergbybloomberg.com/
• The Power Law: Venture Capital and the Making of the New Future - https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X
• Range: Why Generalists Triumph in a Specialized World by David Epstein - https://davidepstein.com/range/
• The Rational Optimist: How Prosperity Evolved by Matt Ridley - https://www.amazon.com/Rational-Optimist-Prosperity-Evolves-P-s/dp/0061452068
• Outliers: The Story of Success by Malcolm Gladwell - https://www.amazon.com/Outliers-Story-Success-Malcolm-Gladwell/dp/0316017930

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 success stories. Discover why he believes failure is not an option, why women-led startups excel, and how a single headstand (yes, you read that right!) can sharpen entrepreneurial intuition.

If you’re a Parallel Entrepreneur hungry for both impact and inner balance, this conversation is your roadmap to thriving in the fast-paced world of multi-venture leadership.

In this conversation, we dive into:

• How openness and authenticity drive healthier board relationships and better decision-making
• Why failure isn’t an option for many minority entrepreneurs
• Why relinquishing control is essential for founders who juggle multiple ventures—and how to do it effectively
• Why women-led ventures often outperform expectations and attract strong investor support
•  What’s happening outside of Silicon Valley in today’s startup world

Time Stamps:

00:00:26 Introduction to Nitin Rai and His Journey
00:05:42 The Importance of Transparency, Leading from the Heart
00:08:49 Challenges in Raising Capital: The Current Landscape
00:14:43 Balancing Multiple Ventures: The Art of Delegation
00:18:05 Navigating Exits: Lessons Learned
00:19:40 Sharing Wealth: The Entrepreneurial Approach
00:22:01 Role Models and Mentorship: Influences on Nitin's Approach
00:24:45 Identifying with Entrepreneurs: A Personal Connection
00:25:40 The Power of Small Ideas
00:25:56 The Power of Intuition
00:27:16 Mindfulness Practices and Self-Care
00:29:51 Celebrating Entrepreneurial Success
00:32:12 The Virtuous Cycle of Wealth Creation
00:34:28 Entrepreneurship as an Art
00:35:23 Defining Success in Entrepreneurship
00:38:24 The US Entrepreneurial Landscape
00:41:01 Advice to Your Younger Self
00:42:14 Reading and Continuous Learning

Show notes:

• Kishau Rogers, Founder of Time Study - https://kishau.com/about/
• Ania Rodriguez, Founder of JourneyTrack - https://www.journeytrack.io/about
• Allie Magyar, Founder of Hubb - https://www.linkedin.com/company/hubb/
• Monica Enand, Founder of Zapproved - https://zapproved.com/about-us/company/
• Nat Parker, Founder of Globe Sherpa (changed to Moovel North America) - http://moovelus.com/
• Ganesh Shankar, Entrepreneur & Investor - https://www.responsive.io/about/
• "Anarchy" by William Dalrymple - https://www.amazon.co.za/Anarchy-Company-Corporate-Violence-Pillage/dp/1635573955
• White Mughals by William Dalrymple - https://www.amazon.com/White-Mughals-Betrayal-Eighteenth-Century-India/dp/014200412X
• Light on Life by B.K.S. Iyengar - https://www.amazon.com/Light-Life-Journey-Wholeness-Ultimate/dp/1594865248

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 trusting your team is your ultimate superpower. He also dishes on where AI fits in modern marketing, the pitfalls of overvaluing your own company, and how a simple dose of salt water therapy can recharge an overworked mind. Whether you're juggling multiple startups or dreaming of your first exit, Roger's candid insights are a must-watch for any Parallel Entrepreneur. Tune in to gain insights from a leader who believes in doing the right thing, embracing change, and leaving a lasting legacy.

Chapters:

00:00:00 Introduction to Parallel Entrepreneurship 
00:00:24 Roger Brown's Journey into Cannabis Testing 
00:01:18 The Thrill of Building Businesses 
00:04:13 Creating Value in Business 
00:05:25 Challenges in the Healthcare Industry 
00:06:30 The Debate: Symptoms vs. Wellness 
00:08:27 The Role of Co-Founders in Business 
00:11:27 Insights from M&A Advisors 
00:14:56 Lessons Learned from Selling Businesses 
00:17:59 Navigating Healthcare's Evolution 
00:20:22 AI's Role in Modern Business 
00:23:14 Finding Balance and Recharging 
00:24:44 Guiding Principles and Life Lessons 
00:28:13 Learning from Mistakes 
00:30:42 Legacy and Life's Purpose 
00:31:53 Rapid Fire Questions 
00:32:59 The Importance of Trust and Team Dynamics 
00:36:44 Embracing Change and Perspective

#ParallelEntrepreneur #RogerBrown #SerialFounder #BusinessExit #HealthcareEntrepreneur #CannabisIndustry #ScaleAndSell #AIInBusiness #TeamLeadership #Entrepreneurship #FounderAdvice #MarkCleveland #ParallelEntrepreneurPodcast #BusinessPodcast #ExitStrategy

© Parallel Entrepreneur, LLC 2024–2026

In this episode of the The Parallel Entrepreneur Podcast, 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 spark rapid innovation
• How psychometric data transforms hiring and retention
• Cultivating a culture that scales alongside your business
• Personal insights on mindfulness, leadership, and building strong teams

Don't miss Jason's fascinating journey and powerful takeaways—perfect for any parallel entrepreneur aiming to juggle multiple ventures with clarity and impact.

Chapters:

00:00:00 Welcome to the Parallel entrepreneur 

00:00:29 Introduction to Jason Putnam and Plum 

00:04:52 Scaling Businesses with Plum's Tools 

00:10:50 Addressing Unconscious Bias in Recruitment 

00:14:08 How AI is Transforming the Hiring Game 

00:17:32 Understanding the Pace Paradox of Change 

00:21:07 Navigating Rapid Change with a 'People-First' Approach 

00:27:45 The Impact of AI in Our Lives 

00:33:32 Lessons from Exits: Building for Success 

00:36:56 How Fast Decisions Spark Innovation 

00:39:46 Fail Fast, Learn Faster: The Entrepreneurial Spirit 

00:44:15 How Jason Finds Mindfulness by Helping Others 

00:45:16 Books Jason is currently reading

Show notes:

• Plum
• Caitlin MacGregor (Founder and visionary behind Plum)
• Move Fast, Break Shit, and Burn Out by Dr. Tracey Lovejoy and Shannon Lucas
• The Talent Fix by Tim Sackett
• Scythe by Neal Shusterman
• Spartan Up by Joe DeSena

#ParallelEntrepreneur #JasonPutnam #Plum #TalentStrategy #HumanCentricLeadership #PsychometricData #HiringInnovation #Leadership #FutureOfWork #AIHiring #Entrepreneurship #MarkCleveland #ParallelEntrepreneurPodcast #BusinessPodcast #FailFast

© Parallel Entrepreneur, LLC 2024–2026