Justin Freishtat joined Sean Kelly on the Digital Social Hour to walk through the path from a family food business to running a fund built on alternative assets. Justin Freishtat describes scaling that first company to $87 million a year in revenue before selling it, and the lessons that shaped how he invests today.
The conversation covers the best and worst bets he has made along the way, along with how he thinks about structuring investments to legally minimize what he owes in taxes — all framed as his own experience rather than a how-to guide.
About Justin Freishtat
Justin Freishtat built his career starting with a family business in the food industry, an operation he grew significantly, including during a surge in demand that preceded its sale. That exit became his entry point into the world of hedge funds and private equity, where he now focuses on building a fund centered on alternative assets.
His current work spans real estate, aviation-related investments like retired airplanes and turbines, and pre-IPO positions in companies such as Starlink and Flexport. He describes his approach as disciplined and diversified, built around long-term cash flow rather than chasing short-term gains.
What Justin Freishtat and Sean Kelly Talked About
- His account of building a family food business into an $87M-a-year operation
- What it was like selling his company after a surge in demand during the pandemic
- His strategies for reducing tax liability through depreciation and alternative asset investments, in his own words
- Why he sees retired airplanes, turbines, and development syndications as options worth considering
- His take on investing in pre-IPO companies like Starlink and Flexport
- How he approaches diversification across real estate, private equity, and emerging tech
- His perspective on staying grounded and avoiding risky, emotional decisions with money
- Why he is focused on growing his fund toward $100 million and beyond
Why This Conversation Matters
This conversation offers a candid look at how one entrepreneur scaled a business, exited it, and rebuilt his approach to money from the ground up. Presented as his own experience rather than financial advice, it is a useful watch for anyone curious about how investors like Justin Freishtat evaluate risk and opportunity.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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