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Parallel Entrepreneur with Mark Cleveland

Parallel Entrepreneur with Mark Cleveland

Von: Mark A. Cleveland
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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.© Parallel Entrepreneur, LLC 2026 Management & Leadership Ökonomie
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  • How to Build an Extraordinary Life Without Following One Path | Ian Adamson

    How to Build an Extraordinary Life Without Following One Path | Ian Adamson
    Jul 7 2026

    What do engineering, world championship sport, product innovation, television production, and the Olympic movement all have in common?

    In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Ian Adamson, Chair of the World Pentathlon Multisport Obstacle Commission, to explore a career built on curiosity, continuous learning, and saying yes to opportunities most people would never consider.

    Ian has spent decades moving between engineering, elite sport, business, product development, and global leadership. From designing products for Nike and competing as a professional adventure racer to helping guide obstacle sports into the Olympic movement, his career is proof that the experiences we collect often become our greatest advantage.

    Along the way, the conversation explores parallel entrepreneurship, decision-making, resilience, innovation, engineering thinking, AI, adventure, leadership, and why living an extraordinary life often begins by embracing the unexpected.

    In this episode:
    • Why Ian believes your greatest superpower is the ability to learn
    • How engineering shaped his approach to leadership and problem solving
    • The mindset behind managing multiple careers at once
    • Walking across China... twice
    • Why saying yes creates opportunities you could never plan for
    • Lessons from building world-class sporting events and international organizations
    • What innovation looks like when you're too early for the market
    • How AI is accelerating discovery and changing the way we learn
    • Why the Olympic movement is about creating better humans—not just better athletes
    • The importance of curiosity, legacy, and leaving the world better than you found it

    Whether you're an entrepreneur, leader, engineer, athlete, or simply someone who enjoys learning from people who have taken an unconventional path, this conversation offers practical wisdom and a refreshing perspective on building a meaningful life.

    Links & Resources

    👉 Join the Parallel Entrepreneur Network
    🎧 The Parallel Entrepreneur Podcast

    Connect with Ian Adamson:
    💼 LinkedIn
    🌐 World Pentathlon Multisport
    🌐 World Obstacle

    About the Host

    Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum without forcing themselves into a single path.


    Key Moments

    00:00 Introduction & Ian's extraordinary career
    01:36 Managing energy across multiple careers
    04:47 From engineer to world champion athlete
    09:01 Building a global sport and the Olympic movement
    12:04 Why saying yes changes everything
    15:24 What Ian would tell his younger self
    16:02 Walking across China... twice
    19:06 Breaking impossible goals into achievable steps
    21:04 Why learning how to learn matters most
    23:00 Innovation, timing, and being too early
    26:30 The power of constant pressure
    29:10 The parallel entrepreneur mindset
    34:37 Identity, curiosity, and lifelong learning
    37:47 AI, discovery, and the future of learning
    45:21 Why everyone should train like an astronaut
    46:39 Lessons from the ocean and thinking beyond ourselves
    50:23 Engineering, safety, and managing risk at scale
    54:29 The Olympic movement and creating better humans
    58:23 Final thoughts

    Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures.

    #ParallelEntrepreneur #MarkCleveland #IanAdamson #Entrepreneurship #Leadership #Innovation #Olympics #Engineering #AdventureRacing #ObstacleRacing #BusinessPodcast #PersonalGrowth
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    59 Min.
  • The AI Skill Every Working Adult Needs to Learn | Spencer Handley

    The AI Skill Every Working Adult Needs to Learn | Spencer Handley
    Jun 23 2026
    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 built on curiosity, learning, and challenging conventional thinking.Spencer shares the story behind Sonora's growth from a guitar education company into a modern learning institution that has helped nearly 6,000 students—including multiple Grammy winners—reach new levels of mastery. He also discusses the recent national attention surrounding Sonora's AI transformation, what actually happened behind the headlines, and why he believes learning to work with AI may become one of the most important skills of the next decade.Along the way, the conversation explores accelerated learning, entrepreneurship, creativity, the future of work, building companies around personal passion, and what world-class performers can teach all of us about continuous growth.In this episode:• Why curiosity has been the common thread throughout Spencer's career • The two-year guitar plateau that ultimately led to founding Sonora • How Sonora has helped thousands of musicians accelerate their learning • Lessons from Grammy-winning artists and elite performers • What really happened when Sonora rebuilt its technology stack • The opportunities and risks AI presents for founders and professionals • Why Spencer believes learning how to manage AI agents is becoming a critical skill • The future of education, work, and human creativityWhether you're a founder, creator, educator, musician, or someone navigating the rapid changes happening in business and technology, this conversation offers practical insights and a thoughtful perspective on what comes next.Links & Resources 👉 Join the Parallel Entrepreneur NetworkThe Time article: The Small Businesses Already Replacing Workers With AISpencer's response: AI Didn't Replace Our Workers. It Replaced Our SaaS Stack.Connect with Spencer: 🌐 Sonora Music Education 🌐 Spencer Handley's website 🌐 Pioneer Species 🎸 Playback Sessions on YouTube 📸 Spencer Handley on Instagram 💼 Spencer Handley on LinkedInSonic Sphere: sonic-sphere.comConnie Yang: Connie Yang on Instagram Connie Yang's portfolioAbout the Host Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum, without forcing themselves into a single path.Key Moments 00:00 Introduction & Spencer's bold prediction about AI 00:43 Welcome to The Parallel Entrepreneur 01:17 The common thread: curiosity and learning 02:00 What is Sonora? 03:00 Why Grammy winners still take lessons 06:38 Studying music at UCLA and the search for mastery 07:38 The "intermediate plateau" that changed everything 10:20 The teacher who transformed Spencer's playing 12:05 How Sonora was born 14:05 The science of learning and creating momentum 17:15 Teaching through transformation, not information 19:45 Building community around mastery 23:00 Creative projects, side ventures, and parallel entrepreneurship 27:00 Why Spencer learned to code 30:00 Using software to solve your own problems 33:30 The entrepreneurial advantage of technical skills 36:15 AI, agents, and the future of work 44:25 The TIME Magazine story 47:40 What really happened inside Sonora's AI transformation 50:30 Why the middle-management layer may disappear 52:00 The human work AI can't replace 55:10 Rebuilding an entire SaaS stack 58:40 Pioneer Species and teaching AI skills 01:01:10 Flow, energy, and avoiding burnout 01:05:20 How Spencer decides what to build next 01:08:50 Managing multiple ventures without losing focus 01:12:40 Lessons from world-class musicians 01:15:20 What Spencer has changed his mind about 01:17:30 The future of learning, AI, and human potential 01:19:10 Final thoughtsSubscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures.#ParallelEntrepreneur #MarkCleveland #SpencerHandley #Sonora #ArtificialIntelligence #Entrepreneurship #FounderStories #CreatorEconomy #FutureOfWork #BusinessPodcast© Parallel Entrepreneur, LLC 2024- 2026
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    1 Std. und 20 Min.
  • Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song

    Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song
    May 26 2026
    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 Capital, for a wide-ranging conversation on independent sponsors, lower middle market acquisitions, leadership, succession planning, AI, uncertainty, and what founders often overlook when preparing for growth or exit.Doug shares lessons from dozens of transactions across multiple industries, including how he evaluates leadership teams, why organic growth still matters more than acquisition rollups, and what makes a business resilient in a world filled with constant disruption.But this conversation also becomes deeply personal.Doug reflects on immigrating to the United States from South Korea as a child, watching his parents build a life through entrepreneurship, and how that experience shaped the way he thinks about people, stewardship, and long-term value creation.The conversation also explores:The rise of the independent sponsor model Why succession planning is becoming urgent for founder-led businesses AI adoption in lower middle market companiesHow great operators handle black swan eventsWhy culture and people matter more than spreadsheets Building blue-collar entrepreneurship pathways for the next generationThe difference between growing fast and growing well Legacy, learning, and designing a life with intentionWhether you're building, scaling, buying, selling, or simply trying to lead well through uncertainty, this episode offers a rare combination of strategic insight and lived experience.Subscribe for more conversations with founders, operators, creators, and visionaries building in parallel.About the Host Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum—without forcing themselves into a single path.About the Guest Douglas Song is the Founder and CEO of Protos Capital, an independent sponsor firm focused on lower middle market businesses. For more than 25 years, he has worked alongside founders and management teams to help businesses grow, transition, and navigate acquisitions with a people-first approach centered on long-term value, stewardship, and community. Links & Resources 👉 Join the Parallel Entrepreneur Network👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.Key Moments 00:00 Why founders need transition plans, not just exits 00:47 Introducing Douglas Song and Protos Capital 01:30 Entrepreneurship Through Acquisition (ETA) explained 03:00 Independent sponsors vs. traditional operators 05:00 Why operators matter more than dealmakers 06:01 The coming succession wave for founder-led businesses 08:15 What "another bite at the apple" really means 11:50 How Protos measures investment success 12:40 Defining the lower middle market 13:50 AI adoption in family-owned businesses 16:30 Using AI during due diligence 17:20 What founders overlook before a transaction 20:00 Growth by acquisition vs. organic growth 23:40 Why organic growth still wins with buyers24:38 Evaluating leadership teams under pressure 27:40 Black swan events and constant uncertainty 31:35 Managing leverage and protecting downside risk 35:22 Is Douglas Song a parallel entrepreneur? 37:20 Lessons learned across multiple portfolio companies 41:15 Why flexibility matters more than fixed timelines 44:20 Different types of capital partners 46:35 What makes founders great partners 49:27 Mentoring the next generation of independent sponsors 52:25 Why community matters in business 53:48 Protecting culture after acquisition 55:08 Doug's immigrant family story and entrepreneurial roots 57:20 Building blue-collar entrepreneurship pathways 01:01:45 AI, uncertainty, and creating opportunities for young people 01:06:05 Books, learning, and the concept of flow 01:10:12 Writing letters to his children 01:11:40 Advice for navigating uncertainty 01:13:40 Restoration, creativity, and balance 01:15:45 Formula 1, Monaco, and memorable experiences 01:17:18 Doug's long-term life plan and legacy goals 01:20:14 Final reflections and closing thoughts#ParallelEntrepreneur #DouglasSong #PrivateEquity #Entrepreneurship #MergersAndAcquisitions #Leadership #BusinessGrowth #IndependentSponsor #AI #FounderJourney© Parallel Entrepreneur, LLC 2024- 2026
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    1 Std. und 22 Min.
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