From High School Dropout to Redefining Modern Wealth Management

What does it really take to rewrite your own story, and then challenge an entire industry at the same time?

In this episode of Startup Builders & Backers, I’m joined by Steven Woods, Founder of Stirlingshire Investments, for a conversation that goes far beyond balance sheets and buzzwords. Steve’s journey is anything but predictable. From leaving high school early to advising on Wall Street, earning credentials from Harvard and Oxford, and ultimately building a firm that questions how modern asset management should actually work, his path challenges many of the assumptions we still take for granted in finance.

We talked about why the traditional broker-dealer model feels increasingly out of step with today’s founders, operators, and investors. Steve shared how transparency, ethics, and genuinely personalized service can coexist with modern technology, and why large firms often struggle to deliver any of those at scale. Rather than chasing complexity, he argues that clarity and alignment are becoming the real differentiators in wealth management, especially for builders who want their capital to work in ways that reflect their values as well as their goals.

What I appreciated most was how practical this conversation became. Whether you are a seasoned investor, a startup founder thinking about long-term financial strategy, or simply finance-curious, Steve offers grounded advice shaped by lived experience rather than theory. We also touched on life outside the boardroom, from growing up in Kansas City to the contrast between Manhattan and Missouri, along with football, fishing, and why good barbecue still matters when building relationships.

If you are building something new or backing others who are, this episode offers a candid look at how personal reinvention and industry change often go hand in hand. As capital, technology, and trust continue to shift, what kind of financial partners will founders and investors really need in the next decade, and are we brave enough to move away from models that no longer serve us?

Useful Links

• Connect with Steven Woods
• Learn more about Stirlingshire Investments,

Thanks to our sponsors, Alcor, for supporting the show.