Are you feeling stuck in your career, yearning for something more but unsure how to make the leap? You're not alone. Many people dream of entrepreneurial success but struggle to break free from the golden handcuffs of corporate life.

In this episode of Scaling the Gap, host Madeleine MacRae chats with Steven Livingston, a self-proclaimed "corporate misfit," and entrepreneur whose journey is as real as it gets. Growing up in Jamaica, Steven’s passion for business started early—he was selling in school and working in investment banking by 17. Years later, he and his wife then made a bold move: buying a franchise while still working full-time corporate jobs. It wasn’t easy, but it was smart. They used what they learned in their careers to grow their business, creating a snowball effect that paid off big time.

But it wasn’t all smooth sailing. Steven opens up about a major financial loss and how it tested his confidence. Instead of giving up, he doubled down—on himself. He also talks about the juggling act of life, likening it to a three-legged stool: it’s not about perfect balance every day, but getting it right over time.

For Steven, success isn’t about titles or money—it’s about growth, humility, and staying grateful. Tune in for an honest, inspiring conversation about entrepreneurship, resilience, and finding your version of success.

Key Takeaways

• Talent + Passion = Magic – Success thrives at the intersection of what you love and what you’re good at.
• Golden Handcuffs vs. Golden Parachutes – Breaking free from corporate security requires conviction.
• Entrepreneurship Isn’t for Everyone – It demands resilience through financial lows and personal sacrifices.
• ADHD as a Superpower – Leverage hyperfocus on passions; delegate weaknesses.
• Redefine Success – It’s about fulfillment, gratitude, and the journey—not just the destination.
• Leadership = Unlocking Potential – Great leaders spot talent mismatches and reposition people for excellence.

In This Episode

• [00:00] Introduction to Steven Livingston
• [01:20] Early life and business ventures
• [05:03] Corporate career and entrepreneurial balance
• [07:20] The leap to full-time entrepreneurship and the inspiration behind it
• [12:37] Finding passion and talent intersection
• [14:09] The luck paradigm
• [17:29] Embracing ADHD as a superpower
• [18:55] The entrepreneurial journey: Unexpected hurdles
• [21:17] Balancing life as an entrepreneur
• [24:26] Defining success: A personal perspective
• [27:30] Crafting your own success algorithm
• [33:30] Final thoughts and farewell

Notable Quotes

• [04:12] “ What I found was I continued to grow at a faster rate whenever I had a business on the side because then I would take the things that I'm learning from business and apply it to my job. And then that allowed me to come with a different approach, a different perspective, a different angle.” — Steven
• [03:37] “I started doing entrepreneurial roles within corporate. I was 100% a corporate misfit.”— Steven
• [05:53] “There would be times when the therapist is looking at me and saying like you were meant to be an entrepreneur, why are you still at work yourself in this position in corporate where the skill sets has gotten you to a certain point that it creates what they call the golden parachute.”— Steven
• [13:47] “In many cases, people are just in the wrong seat doing the right things. Right the wrong seat, doing the wrong things. But it's for a leader to establish what the right things are. Part of leadership is identifying where those two intersect so you can find that talent.” — Stevenu
• [12:37] “I've always lived by the philosophy that where talent and passion intersect, there is where magic is formed.” —...