E10: Match Group’s Sam Yagan on Unexpectedly Becoming the CEO of the Public Company that Acquired You

Today we are thrilled to have Sam Yagan, co-founder of OKCupid and ultimately the CEO of Match Group through its rapid growth and IPO. Sam takes us behind the scenes of OKCupid’s gripping acquisition process (including phone calls from the delivery room). He also dives into his unlikely journey of being selected successor to his acquirer -- becoming the CEO of publicly traded Match Group. Jesse is joined again by special co-host Ryan Caldbeck: a startup founder and CEO himself, who is also well known on tech Twitter for discussing founder mental health. Don't forget to catch up on Ryan Caldbeck's In The Arena episode, “Terrifying Growth”, Managing Mental Heath, and Radical Sharing- linked below.

Apple: https://podcasts.apple.com/us/podcast/e7-ryan-caldbeck-on-terrifying-growth-managing-mental/id1691530886?i=1000623146998

Spotify: https://open.spotify.com/episode/7H9Q0Cbudh3DeIKTzjTHBc?si=5HyYcAXRTxemSGNP9tzZ4Q

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TIMESTAMPS:

(01:00) Episode Preview: Sam Yagan

(03:30) The day Sam is about to sign a term sheet to sell OKCupid

(16:37) “Am I gonna miss my kid’s birth?”

(19:50) A last-ditch effort

(23:44) The deal is on! Sam’s reflections on dealmaking and unmaking

(35:30) The state of the co-founders and exec team prior to selling

(44:55) Would Sam have done things differently if he had traditional venture backing?

(48:00) Failure feelings about getting out

(58:18) Sam’s best advice

(1:04:00) After the deal: Sam stays on with OKCupid and then catapults to CEO of Match Group

(1:13:53) Match’s wartime CEO

(1:20:15) Individual relationships in business matter, even as companies scale

X:

@samyagan (Sam)

@ryan_caldbeck (Ryan)

@jessegenet (Jesse)

@eriktorenberg (Erik)

@inthearena_pod