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.

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

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