
Kyle officially joins the solopreneur ranks — and immediately finds out that freedom comes with invoices, admin, and double LLC fees. CJ welcomes him to the chaos before breaking down Wealthfront’s IPO, a masterclass in efficiency with 46% EBITDA margins and a Rule of 71. From there, the crew dives into take-private season in SaaS, unpacking why companies like Couchbase and PagerDuty are retreating from the public markets. Then it’s onto LinkedIn chaos — the algorithm, the pitch-slaps, and the mystery of why everyone’s engagement tanked. They close with a tangent only this show could pull off: a Japanese man’s world record sprint on all fours, the surprising Guinness origins, and a lightning round on Waymo’s taxi empire and trying out Stripe.
00:00 – Intro
04:40 – Kyle Goes Solopreneur: What Could Go Wrong?
10:16 – The Wealthfront IPO Breakdown
22:33 – Take-Private Season
27:27 – Private Equity: Efficiency or Exploitation?
32:27 – Are You Bad at LinkedIn, or Is the Algorithm?
43:17 – The LinkedIn Pitch Slap
46:33 – Obscure World Records
48:01 – Lightning Round: Waymo & Stripe
Links
https://www.growthunhinged.com/p/a-new-chapter
https://www.mostlymetrics.com/p/wealthfront-ipo-s1-breakdown
https://www.mostlymetrics.com/p/netskope-ipo-s1-breakdown
https://www.mostlymetrics.com/p/navan-ipo-s1-breakdown
https://www.lookingforleverage.com/p/take-private-szn
https://tuck.dartmouth.edu/news/articles/where-did-all-the-public-companies-go
https://www.axios.com/2024/05/31/vista-equity-pluralsight
https://www.amazon.com/Plunder-Private-Equitys-Pillage-America/dp/1541702107
https://www.nytimes.com/2025/07/09/business/youth-sports-private-equity.html
https://www.linkedin.com/in/cj-gustafson-13140948/recent-activity/all/
https://x.com/Patticus/status/1456266281833746445
https://en.wikipedia.org/wiki/Guinness_World_Records#History
https://web.archive.org/web/20120225172648/http://guinness.book-of-records.info/history.html
https://www.stumbeanos.com/wpress/the-story-of-gus-comstock-worlds-coffee-drinking-champion/