Tim spent 35 years as a commercial banker, the last 20 lending to tech startups, and never once got in trouble with a regulator. At 60 he started the Austin Pickle Ranch, and the city of Austin spent the next three years teaching him why bankers make poor real estate developers. He's 64 now, plays in every 7 a.m. game, and bought into a pro team as one of the eight original founders of Major League Pickleball.

What he covers:

→ Telling a guy at a 2019 Wimbledon finals watch party that pickleball is "for losers who can't play tennis," then playing it at his house that night

→ Raising 1Minfoundingmemberdeposits(5,000 for five years of free play) with a college intern answering inbound emails while checks showed up in the mail

→ Structuring those deposits as a loan, not a security, so he never had to register with the Texas State Securities Commission

→ Giving all $1M back to members when the delays dragged on

→ A city that tried to declare a river through the middle of his land, three years of fighting it, and the epiphany that renting beats owning

→ His first location in a downtown parking garage: it killed it there, then noise complaints and zoning shut it down

→ A 70-location pickleball chain filing Chapter 11 the same week, and the overbuild Tim predicted back in 2023

→ Why venues paying 70-80% of revenue in rent are nearly impossible to buy (a typical SaaS company pays 10-15%)

→ Why every pickleball court is the same size, and why community is the only real differentiator

→ Being willing to be "the bad guy" when a player's DUPR rating isn't high enough for the top game

→ Turning down a Merrill Lynch move to San Francisco in the mid-90s, then driving his parents nonstop from Columbus to Austin in a minivan after his dad's stroke

→ The one thing he'd do differently: raise outside money earlier

🔗 CONNECT WITH STU

Instagram: @stu

Website: https://startupswithstu.com

📌 CHAPTERS

00:00 – Intro: from 35 years of commercial banking to a pickle ranch

02:30 – Why a banker who backed tech startups became a founder at 60

05:00 – Lending against raw land and the Wimbledon night that changed the plan

09:00 – The downtown parking garage location: killed it, then got shut down

12:00 – A river nobody could find on a map and the "rent, don't own" epiphany

16:00 – $1M in founding member deposits, then giving all of it back

20:00 – The $5,000 loan structure: five years of free play, no securities filing

23:30 – Predicting the pickleball overbuild in 2023 and the 70-location bankruptcy

26:30 – Every day at the club: 7 a.m. games and midnight closes

29:00 – Four generations on one block and the San Francisco job he turned down

32:30 – Branding, a brand book, and why Yellowstone helped

35:00 – Why buying a pickleball venue rarely pencils out (rent at 70-80% of revenue)

38:00 – Community as the moat: open play, ratings, and being the bad guy

42:00 – Stu on dialing in the customer experience

44:00 – What Tim would tell himself before starting: raise outside money earlier

⚠️ Note: Timestamps are estimated from transcript flow. Swap to actual timecodes before publishing.

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