A Million Ways to Make a Million Bucks

James McCabe
  • 5.0 (13)
  • Entrepreneurship
  • Updated Weekly

We believe there could be a million ways to create wealth. James McCabe spends time with individuals around who they’re being that allows them to preform at a high level. We felt that generating a million dollars of income in a 12 month period could be an appropriate benchmark to define “high level.” Join us as they share their experiences, lessons learned, useful perspectives and how they did it.

  1. Sep 8

    Fired 5 Times Before Building Millions | Dave Lee

    Dave Lee was rejected from every business school he applied to and fired from five different companies. Today, he looks back at those failures as some of the most important turning points in his life. In this episode, James McCabe sits down with Dave Lee to talk about his journey through the early days of SaaS, helping build Infusionsoft, losing jobs, supporting a young family, and eventually walking away from a potential presidency at LeadMD to pursue an entrepreneurial opportunity of his own. That decision ultimately led to a multimillion-dollar business—but the lessons Dave shares are bigger than the outcome. They discuss taking calculated risks, selling before overbuilding, using white-label software instead of reinventing the wheel, validating whether customers will actually pay for an idea, and how AI is changing what entrepreneurs can build. Dave also opens up about the role his wife and family have played throughout his journey, why having someone who genuinely believes in you can change what you believe is possible, and why business doesn’t necessarily need to be your passion. Sometimes, business is the vehicle that gives you the freedom to pursue what you truly love. An episode about entrepreneurship, resilience, family, calculated risk, and continuing to create when life doesn’t go according to plan.

    Fired 5 Times Before Building Millions | Dave Lee

  2. Aug 25

    Will Humphreys: How to Scale Without Becoming a Slave to Your Business

    Will Humphreys' career almost ended before it began. Weeks after 9/11, a misunderstanding involving creatine at his university led to an FBI investigation, suspension from school, and a year-long fight to save the career he'd spent seven years pursuing. Years later, Will faced another breaking point—this time as an entrepreneur. His physical therapy practice had only $5,000 left with $10,000 in bills coming due, and the business he'd created for freedom had become something he felt trapped by. That moment became a turning point. In this conversation with James McCabe, Will shares how he went on to scale his practice, build multiple multimillion-dollar businesses, find the opportunity that became Virtual Rockstar, and create a life centered around income, impact, freedom, family, and purpose. James and Will break down business focus, leadership, mentorship, networking, scaling, burnout, finding your “one thing,” and why the most successful entrepreneurs learn to say no to almost everything except what matters most. If you're building a business—or trying to make sure your business doesn't end up owning you—this conversation is for you.

    Will Humphreys: How to Scale Without Becoming a Slave to Your Business

  3. Aug 18

    Shane Rowley: How 3,300 Credit Cards Taught Him to Scale 100X

    Shane Rowley has one of the wildest entrepreneur stories we have heard. Before co-founding Nimbl, Shane spent years finding patterns, spotting overlooked opportunities, and scaling them in ways most people would never imagine. He and his wife had over 3,300 credit cards, he bought $10 million of gold on credit cards, earned massive amounts of points, got an Amex black card, nearly redeemed points for a Virgin Galactic flight, and ended up spending time on Richard Branson’s private island. But this conversation is about much more than credit card points. James McCabe sits down with Shane to talk about creativity, risk, leverage, family, fulfillment, and the shift from chasing short-lived opportunities to building something with lasting value. Today, Shane is the co-founder and president of Nimbl, an outsourced accounting department for small businesses that provides accounting, tax, FP&A, forecasting, CFO support, cybersecurity, device management, and global staffing services. This episode is about how to see opportunity, how to scale responsibly, and how to find the work that makes you feel alive. In this episode: What Nimbl does for small businesses Why many founders need financial help earlier than they think How Shane and Dave Olson became business partners Growing up in an entrepreneurial family The story behind Shane’s 3,300 credit cards How he earned and used massive amounts of credit card points The Amex black card story Buying $10M of gold on credit cards Almost redeeming points for a Virgin Galactic flight Ending up on Richard Branson’s Necker Island Why Shane eventually walked away from the side-hustle world The power of focusing on one real business How to find what makes you feel alive Connect with Shane: LinkedIn:https://www.linkedin.com/in/rowley-shane/ Nimble: trustnimbl.com

    Shane Rowley: How 3,300 Credit Cards Taught Him to Scale 100X

  4. Aug 11

    Mikey Taylor: The Path from Pro Skater to Investor and Mayor

    Mikey Taylor sits down for a wide-ranging conversation that traces an unlikely path: hard-charging pro skateboarder who turned his parents’ neighborhood into a legendary skate house, built signature product deals and royalties, launched (and exited) a craft brewery after Rob Dyrdek crumpled up the business plan, founded real-estate firm Commune Capital, and became mayor of his hometown—all while reordering his priorities around faith, marriage, and kids. They dig into the real economics of extreme sports, how young athletes (and their parents) should think about sponsorships, social media, and long-term money, why most pro athletes still go broke, the difference between building to exit versus building a machine, contrarian California real-estate investing, and the practical systems Mikey uses to protect family time while running multiple businesses and serving in local politics. Honest, tactical, and grounded. Chapters 00:00 – Sean Malto’s text & the legendary 2007 skate house 04:30 – Skater → founder → investor → mayor 09:20 – How extreme athletes actually make money 13:00 – Parent playbook + the hard “no” on kids and social media 18:00 – First pro checks, royalties & the early money discipline 25:20 – Rob Dyrdek’s 10-year rule on business 31:00 – Building to exit the right way (vs. cash-flow machines) 39:00 – Why become mayor when there’s zero upside? 43:30 – Contrarian California investing + favorite markets 51:00 – Athlete money playbook: control lifestyle or lose it all 56:30 – The hard reset: God → wife → kids → business 1:03:40 – Definition of success + final 10X challenge

    Mikey Taylor: The Path from Pro Skater to Investor and Mayor

  5. 09/15/2025

    Giveaway Marketing: Expert Van Oakes Behind Goat Media’s Ecom Success

    Scaling with Giveaway Marketing | Van Oakes of Goat Media Van Oakes is the founder of Goat Media and one of the top voices in giveaway marketing and paid ad strategy. He’s helped brands like Diesel Brothers scale to 9 figures using giveaway-based customer acquisition, direct response funnels, and Shopify-first thinking. In this episode, Van opens up about: The business model that made Diesel Brothers a $100M brand Why giveaways still outperform traditional ads in 2025 How Goat Media scales brands using performance-first paid ads The numbers behind real ecom growth: CAC, LTV, and AOV benchmarks Transitioning from door-to-door sales to owning a top-tier agency What most ecom brands get wrong when trying to scale Balancing family, business, and personal trials without losing it all Timestamps: 0:00 – Intro 1:20 – Van’s first big win in D2D 10:45 – Building Diesel Brothers with giveaways 18:50 – The Goat Media model explained 30:00 – How to price and position a giveaway 40:15 – Mistakes to avoid in paid ads 50:05 – Life after $100M: family, trauma, and truth 1:10:00 – Final thoughts on scaling sustainably If you’re in e-commerce, digital marketing, brand building, or growth strategy, this episode is a masterclass in what works now. No fluff—just real frameworks, tested campaigns, and the story of a founder who’s led from the front, failed big, and still came back stronger. 💬 Connect with Van on IG: @itsyourboyvan 💼 Learn more: https://goat4media.com/

    Giveaway Marketing: Expert Van Oakes Behind Goat Media’s Ecom Success

  6. 09/08/2025

    Kidswear: How Matt Fisler Started Binky Bro

    Binky Bro Founder Matt Fisler on Building a Kidswear Brand, Starting a Business, and Leaving Tech for E-Commerce Matt Fisler, founder of the kidswear clothing brand Binky Bro, breaks down how he turned a side hustle into a multimillion-dollar children’s apparel company. In this podcast episode, Matt shares how he left his job at Qualtrics to start a profitable e-commerce business, what it’s like building a company with your spouse, and how Binky Bro became a leading surf-style kidswear brand. This is a must-listen for entrepreneurs, brand builders, e-commerce founders, and anyone in the kids fashion or DTC space. Topics covered: How to start a kidswear brand Family-run business tips E-commerce business growth Startup branding strategies From Qualtrics to full-time founder Shopify, scaling, and organic marketing Building a lifestyle brand for parents Kids fashion trends and retail strategy Perfect for: Listeners interested in entrepreneurship, kidswear fashion, DTC brands, Shopify startups, family business, and startup case studies. Timestamps: 01:19 A Blast from the Past: Memories of Scotland 06:19 From Mission to Career: The Journey Begins 08:10 The Qualtrics Experience: Lessons and Growth 14:37 The Entrepreneurial Spirit: From Ideas to Action 29:38 The Birth of Binky Bro: From Concept to Reality 38:06 The Grind Behind the Success 40:46 Starting a Business with Your Spouse 42:34 Balancing Personal and Professional Life 49:06 Philosophy on Business Growth 01:00:00 Decade of Influence: Prioritizing Family 01:07:51 Exciting New Ventures and Collaborations 01:11:23 Giving Back: Legends are Born Every Day Foundation Keywords: Binky Bro, Matt Fisler, kidswear brand founder, start a kids clothing line, Shopify brand, e-commerce success story, leave tech for business, surf kids clothes, family startup podcast

    Kidswear: How Matt Fisler Started Binky Bro

  7. 09/01/2025

    Influence VC: Bubba Page on Fatherhood & Building Wealth Without Debt

    Bubba Page is an entrepreneur, investor, and father of eight—best known for building and selling LaunchLeads, then launching Influence VC to help fund early-stage startups. In this episode, he breaks down the principles that guided his journey to financial independence—without ever relying on debt. We cover: How Bubba built a profitable B2B company and exited in 2020 The mindset shift from operator to angel investor How Influence VC works as a syndicate model Why he paid off all his real estate assets—including a $3M cabin The dangers of over-leverage for founders What spiritual discipline and parenting strategy look like at scale Why lifestyle businesses often outperform the hype of venture-backed startups This episode is packed with practical advice for entrepreneurs, business owners, and creators looking to build sustainable wealth and live intentionally. Search terms: Bubba Page podcast, entrepreneur investor dad, Influence VC, startup founder, business exits, building wealth without debt, how to invest early-stage, fatherhood and money, LaunchLeads founder, no debt philosophy, millionaire mindset, family-first entrepreneurship Chapters: 00:00 Defining Bubba Paige 01:35 Pro Tips for Aspiring Entrepreneurs 03:13 College Entrepreneurship and Early Ventures 05:33 The Impact of Failure and Rebirth 07:22 Investing Strategies and Principles 16:56 Diversification and Risk Management 30:05 Debt, Peace of Mind, and Financial Freedom 40:04 The Importance of Financial Security 41:20 Finding Financial Stability 49:07 The Father Operating System 54:47 Daily Habits for Success 56:00 The Value of Spiritual Connection 01:00:31 Creating a Balanced Life 01:06:23 Final Thoughts and Future Plans

    Influence VC: Bubba Page on Fatherhood & Building Wealth Without Debt

  8. 08/25/2025

    Sandlot Investor Casey Baugh on Rejection & Value Creation

    Casey Baugh—entrepreneur, private equity investor, and co-founder of Sandlot Partners—joins James McCabe to share how he scaled from door-to-door sales to leading a multimillion-dollar investment firm. In this episode, Casey breaks down proven strategies for leadership, business planning, and emotional resilience. Discover Casey’s personal routines, sales psychology, and the planning framework that drives results. Whether you’re a startup founder, sales leader, or aspiring investor, this episode offers practical tools for long-term business and personal success. Timestamps: 00:00 Overcoming Rejection and Building Confidence 07:03 The Psychology of Sales 11:06 Balancing Work and Personal Life 15:24 Principles of Leadership and Influence 20:04 The Holistic Approach to Adding Value 36:55 Embracing Change and Being Present 38:13 The Happiness Exercise & Being Deliberate in Life 42:48 Life's Struggles and Perspectives 45:16 Making Progress Every Day 48:42 Investing in Yourself 53:07 The Power of Weekly Planning 01:02:58 Roles and Goals 01:10:00 The Importance of Taking Risks Important Links: Casey's LinkedInCasey's PodcastSandlot Partners Keywords: Casey Baugh, Sandlot Partners, private equity, investor mindset, door-to-door sales, entrepreneurship, leadership development, business strategy, emotional intelligence, productivity, financial growth, weekly planning, how to raise capital, investor advice, sales success

    Sandlot Investor Casey Baugh on Rejection & Value Creation
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We believe there could be a million ways to create wealth. James McCabe spends time with individuals around who they’re being that allows them to preform at a high level. We felt that generating a million dollars of income in a 12 month period could be an appropriate benchmark to define “high level.” Join us as they share their experiences, lessons learned, useful perspectives and how they did it.

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