Get into the heads of five intrepid alumni who launched multiple businesses
Tuesday, February 28, 2023

What do all serial entrepreneurs have in common? 

It’s likely they have burning curiosity and excitement for emerging markets, but at their core, they are certainly all adept problem solvers.  Are you an aspiring entrepreneur? Read on for their expert advice.


Ken Buckman







Ken "Bucky" Buckman (BBA92)

Business Ventures:
CEO & Founder, Rainy Investments/Rainy Capital
CEO & Founder, Boxinator
Founder, Rainy Solar
Founder, TradeTec

Bucky's Advice:

  • If you want to invent the next Facebook or Amazon, get a steel pole and wait for lightning to strike—while playing the lottery. Accept that virtually everything has already been invented. Instead, ask how you can improve something that people complain about and tackle that pain point. 

  • Find mature mentors. Seek counselors in every aspect and phase of your life. I’m talking 15 to 20 of them. Peer-to-peer groups are especially valuable and will become pseudo family. 

  • If you have a Plan B, don’t start. You have to have absolute belief in your idea.  


Leah Borgeson Stigile







Leah Borgeson Stigile (BBA04) 

Business Ventures:
Co-founder and CEO
, Hai

president, Fame & Partners

Former global head of e-commerce, TOMS

Former associate, Goldman Sachs

Leah's Advice:

  • Don’t be afraid of remote teams. Hai is completely virtual, with West Coast employees, overseas manufacturing, and product development in Australia and New Zealand. Digital meetings are essential: one-on-one meetings with direct reports, team meetings, and daily standups. 

  • Get ready to be told no a lot, especially if you are pushing people to think or act in a new way. Highs and lows can come at you on an hourly basis. Have a fundamental belief in what you are doing and keep pushing.  

  • Spend time with someone before agreeing to a business relationship. A great co-founder is someone you trust. Be honest about your strengths and weaknesses. 


Andrew O'Hara







Andrew O’Hara (BBA09) 

Business Ventures:
Co-founder and CEO, Modern Pediatrics
o-founder and former CEO, Chiron Health
Former equity research associate, William Blair

Andrew's Advice:

  • Almost any successful startup today is going to be a tech company in part, so it’s important for at least one of the founders to have technical DNA. It doesn’t always have to be a formal background; I taught myself coding. 

  • Be customer obsessed. Spend time doing frontline supportyou don’t want to be shielded from important feedback.  

  • Find a problem that’s a little messy or complicated and solve it. That’s how you find the competitive edge—seize opportunities that need fresh thinking and new energy. 


Aristotle Loumis







Aristotle Loumis (JPEC Entrepreneur Accelerator, 2014) 

Business Ventures:
& chief business officer, Fyllo

o-founder, Wesana

Founder, Ellison

+many more!

Aristotle's advice:

  • Go on another entrepreneur’s journey for a period of time. Get into a company with fewer than 10 employees and find where you can add value. Bring all your ambition without assuming liabilitywhat you learn will be invaluable.  

  • Embrace the non-sexy side of business. The devil is in the details, but that’s how great companies are made. Be part of the “back-of-house” excellence.  

  • Find a health regimen that works for you. We talk about athletes and their off-field performance—have the same mindset for your physical and mental wellness outside of business. 


Sara Larson







Sara Larson (JPEC Venture School, 2017)

Business Ventures:
, Gnarly Pepper

, Lovoto LLC
Marketing Director, BeraTek Industries 

Sara's Advice:

  • Don’t be afraid to ask for raw insights about someone else’s business journey. Pick their brains about operations; even ask about their mistakes. They don’t need to be in the same industry!   

  • Focus on a niche that’s truly in your heart; otherwise, you can lose sight. Remember: this idea originated for a reason, whether it’s your life purpose or simply the next opportunity within reach. 

  • People may shut you down in the beginning. Your neighbor, closest family, even your best friend will not be your biggest customer. Filter out naysayers and find supporters.  



This article appeared in the Spring 2023 issue of Tippie Magazine.