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Tim Jackson

General Partner and CEO Coach at Walking Ventures

Tim Jackson is a seasoned CEO coach and seed investor with a diverse background spanning venture capital, entrepreneurship, journalism, and authorship. He has served as a mentor at prestigious programs like Seedcamp, Techstars, Entrepreneur First, and Ignite100. His educational background includes a MA in Philosophy, Politics & Economics from the University of Oxford. Tim has been affiliated with numerous organizations in various capacities ranging from CEO coach and investor to advisor and director.

Highlights

Sep 9 · linkedin

Amazing nugget for Series B+ founders, hidden in the FT and New York Post last week.

Peloton, the fitness bike company founded by John Foley, soared to a $50bn valuation during the pandemic, only to crash. Typical post-IPO risk, right? But here's the twist: according to the Post, Foley had to offload his $55m East Hampton house in a fire sale.

Why? Despite a holding in Peloton worth (at a guess) $2.4bn at the peak), Foley borrowed against his shares, rather than selling to buy the things he wanted.

At first glance, that seems smart—why sell at $50bn if you believe your company could hit $1tn? But the problem: loans against stock don’t diversify risk. When Peloton’s stock tanked, Foley faced margin calls. If that happens to you, assets bought with borrowed money—jets, boats, houses—are no longer yours.

Foley doesn’t need sympathy (he’s a smart guy, and has a new startup). But founders need outside perspectives for big decisions like this, beyond just advice from VCs or bankers.

I’ve had several chats with founders lately about whether to sell part of their stake, and if so what to do with the money and whether to take loans. It’s a good problem to have, but requires careful planning—especially if you want to keep that new toy, whether it's a $50m Hamptons house or a £500K London flat.

Peleton S1: https://lnkd.in/eu3RTXEw FT story (paywalled): https://lnkd.in/eq5wWdXr New York Post story: https://lnkd.in/eS3bDrjP Peleton stock price chart: https://lnkd.in/eGEQc_9a

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London, England, United Kingdom