#293 | Jarrad Holst; Real Estate, Risk Tolerance & Eternal Optimism

About this episode

Jarrad Holst — real estate investor/attorney, Vance's friend and the person who introduced him to his business partner Ben Anderson — delivers an extended meditation on risk tolerance, urban investment, and eternal optimism, all traced back to a genuinely difficult childhood (divorced parents, an ADHD diagnosis he refused to medicate) that he frames as the source of his resilience rather than a wound. He makes an impassioned case for continued investment in downtown St. Louis, tying his real estate strategy to a family legacy of immigrant ancestors who "built to last," and argues that reversing urban decline requires city-county reunification and continued capital investment rather than just more policing. The conversation ranges widely: the philosophy of risk (citing Marcus Aurelius, chess vs. checkers thinking, and his grandmother's "worn out body" mentality), the importance of personal presence and fashion as "self-portrait," a rejection of American aristocracy in favor of "first-generation hustlers," his approach to law as a relationship-driven practice rather than billable-hours grind, and an extended philosophy of networking rooted in reciprocal generosity ("givers gain"). He closes with reflections on raising his kids (including a son with autism) in the city rather than sheltering them in the suburbs, framing authentic exposure to hardship as essential parenting, and credits mentors like John Porta for showing him the same door-opening generosity he now extends to others.

“To tuck and run and go out to the county, in my mind, you're kind of pissing on their legacy... they chose to build things with oak and with stone and with brick for a reason, because they wanted them to last.”

“You have to build the foundations first before you're gonna get the population to come in... you had to build this huge steel wicket [the Arch].”

“I'm a firm believer in givers gain... if I see people that I believe in, I want to do whatever I can to help them. There's no ulterior motive there.”

Key moments

• St. Louis decline framing — population drop from 700k to 300k since 1950, attributed to white flight, segregation, and divestment, paired with an insistence the city is now recovering (cranes in the skyline as evidence).
• "Build it and they will come" thesis — the Gateway Arch as proof that audacious infrastructure investment precedes population growth, drawn from Flagler, Disney, and Lewis and Clark's mapping of the Louisiana Purchase.
• The German uncle's wallet demonstration — cash vs. credit cards as a metaphor for American risk tolerance versus German risk aversion, explaining Jarrad's "no such thing as failure" philosophy.
• ADHD as a blessing, not a deficit — refusing medication as a child and crediting undiluted hyperfocus for his professional success.
• The law firm negotiation — restructuring his own compensation (no billable-hour requirements, salary plus percentage of business) by building a relationship-driven book of business instead of grinding hours.
• Deliberately raising kids in the city rather than the suburbs — "I want him to see that, that's authenticity" — including hearing what might be gunshots from the porch and choosing to stay and improve the neighborhood rather than retreat.
• Mentor tribute to John Porta and reflections on why he mentors younger real estate professionals — "you can't take that with you to the grave."

Notable quotes

“You had to build this huge steel wicket [the Arch]... people aren't just gonna come first and look at a river and go, all right, this is nice.”

“This is the United States [credit cards]. This is Germany [cash]. We're very risk adverse... Americans will take all the risk under the sun, sometimes will lose their butts. But you guys come up with a lot of things.”

“I look at ADHD as one of the greatest blessings I could ever have... I refused medication, and I'm glad I did.”

“I do not wanna shelter them behind some white picket fence... I want him to see that, that's authenticity.”