20VC: The Largest Venture Backed D2C Consumer Exit; PillPack: $0-$300M Revenues in 5 Years & The Biggest Lessons Scaling the B2B Business to $300M in 2.5 Years with TJ Parker, Co-Founder @ PillPack
5th June 2023
Jon Callaghan is a founder of True Ventures, one of the West Coast’s leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of WordPress) and more amazing companies. Jon also led the deals and sits on the board of Fitbit, Brightroll, Peloton and Glu Mobile, just to name a few. Prior to True, Jon founded 3 of his own companies, the first being in 1986 with Mountain Bike Outfitters Inc. Following several years founding companies, Jon made his move into VC with Summit Partners and then enjoyed roles with AOL’s venture incubator, CMGi’s Venture group and Globespan Capital.
In Today’s Episode You Will Learn:
1.) How Jon made his first forays into the world of VC and came to co-found True with Phil Black?
2.) How does Jon look to straddle the divide of “founder/VC”? Why does Jon believe it is crucial to have an entrepreneurial mindset as an investor?
3.) Why does Jon believe VCs biggest bias is loss aversion? Why does Jon always believe that the role of the VC is to maximise risk? What 1 thing must all prospective investors get good at very quickly?
4.) How does Jon view reserve allocation? True invest -1% per deal in each company, how do they look to efficiently deploy reserves? What must the communication be between founder and VC with regards to attaining follow on funding?
5.) Why does Jon believe that current board meetings do not serve startup founders? What are the characteristics of the best board members and how they conduct themselves? What is the single biggest problem boards bring to founders?
Items Mentioned In Today’s Show:
Jon’s Fave Book: Moby Dick
Jon’s Fave Blog: Dave Pell: NextDraft
Jon’s Most Recent Investment: Brava
As always you can follow Harry, The Twenty Minute VC and Jon on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
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2nd June 2023