Why This Ex-Wall Street Banker Left It All to Build an AI Startup

Sara Wyman, founder and CEO of Stackpack, joins me to share her journey from investment banking and a Wharton MBA to launching a company that’s redefining how finance and operations teams manage vendors. From surviving the Bear Stearns collapse to scaling Etsy and Affirm through IPOs, Sara’s career has been built on spotting patterns and acting with conviction. In this episode, she breaks down how she validated her idea with 75 CFOs before writing a line of code, why timing and conviction matter more than a perfect resume, and what it really takes to leave the safety of corporate life to build something of your own.

Key Takeaways

• Why solving a problem you’ve lived through yourself is the best foundation for a startup

• How interviewing potential customers before building can double as both research and sales

• Why founders should outsource what they’re not great at instead of spinning wheels

• The hidden advantage of years of work experience when stepping into a founder role

• Why pace setting—not just hiring—is one of the founder’s most critical responsibilities

Timestamped Highlights

00:39 — What Stackpack does and how it helps finance teams gain full visibility into spend and contracts

02:10 — Lessons from investment banking, the Lululemon IPO, and the realization she wanted to be the CEO, not the banker

04:30 — Spotting the problem of vendor chaos and validating it through 75+ CFO conversations

07:12 — The leap from corporate security to founder risk and why timing mattered more than age

12:47 — A different founder path: starting with customers and funding before building the team

17:15 — Why the stereotype of the 24-year-old coder isn’t the reality of most successful exits

19:45 — Hard-earned lessons: outsource what you don’t excel at and embrace the founder role as a pace setter

A Standout Moment

“If you’re not awesome at something, outsource it or find the person that is. You don’t get bonus points for struggling through work that isn’t your strength.”

Pro Tip

Talk to customers before you build. Sara’s early interviews not only validated her idea but converted into her first paying design partners.

Call to Action

If Sara’s journey resonated with you, share this episode with someone considering the founder path. Don’t forget to follow the show on your favorite platform so you never miss stories like this one.