Founder's Story · Nov 4, 2026 · 32m · 26m saved
With Robert Herjavec, Shark Tank investor and Founder of Cyderes
Elon Musk sold his PayPal shares for $180 million, then borrowed $20 million and put it into Tesla. Robert Herjavec, the Shark Tank investor and founder of cybersecurity firm Cyderes, told Daniel Schlaepfer on Founder's Story that most successful founders keep making bets like that one — and it's exactly why so many of them end up broke.
"Being a great founder doesn't... has nothing to do with being great with money. Those are two completely different things." — Robert Herjavec
Robert bootstrapped his first business to $200 million in revenue before ever taking a bank loan, then sold a later company to a private-equity firm managing roughly $87 billion — a transition he says exposed exactly how different those two skills are.
The full interview is covered here so you can skip it. 32 minutes of audio, 6 minutes of reading.
Here are the 5 takeaways that matter.
Key Takeaways
Founding and money management are opposite skill sets, Robert says
Elon Musk sold PayPal shares for $180M, then borrowed $20M to bet on Tesla
Robert and Mark Cuban walked off the set of Shark Tank over a deal they saw as a charity gift
Obsession, not passion, is what starting a business actually requires, per Mark Cuban's line to a contestant
Immigrants get a work-ethic advantage but a business-literacy disadvantage, Robert says
Robert paid off his house at 25 and says that's how he got past the fear of losing everything
1. Why Founders Go Broke
Robert's core argument is that founding and money management are opposite skill sets. Building a company means believing in something that doesn't exist yet and taking on risk fast; being good with money means patience, diversification and the long game of compounding.
Being a great founder and being great with money are two completely different skills, Robert says
"Being a great founder doesn't... has nothing to do with being great with money. Those are two completely different things." — Robert Herjavec
He pointed to Elon Musk as the extreme case: someone who sold one success for cash and immediately bet it on the next long shot rather than diversifying.
Musk sold his PayPal shares for $180 million, then borrowed $20 million to bet on Tesla, Robert says
"He sold his shares in PayPal for $180 million, borrowed $20 million, and invested it in Tesla. I mean, who would do that?" — Robert Herjavec
Robert said his own instincts flipped once he sold a company to a private-equity firm managing roughly $87 billion. He had bootstrapped his first business to $200 million before ever taking a bank loan, and that same frugality made him good at building it. Once other people's money was involved, the same instinct made him a worse partner, because he fixated on spending it as if it were his own.
