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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RECOMMENDED PODCAST:

Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution.

Apple: https://podcasts.apple.com/us/podcast/id1786227593

Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg

YouTube: https://www.youtube.com/@ModernRelationshipsPod

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The HR industry is at a crossroads. What will it take to construct the next generation of incredible businesses – and where can people leaders have the most business impact? Hosts Nolan Church and Kelli Dragovich have been through it all, the highs and the lows – IPOs, layoffs, executive turnover, board meetings, culture changes, and more. With a lineup of industry vets and experts, Nolan and Kelli break down the nitty-gritty details, trade offs, and dynamics of constructing high performing companies. Through unfiltered conversations that can only happen between seasoned practitioners, Kelli and Nolan dive deep into the kind of leadership-level strategy that often happens behind closed doors. Check out the first episode with the architect of Netflix’s culture deck Patty McCord.

https://link.chtbl.com/hrheretics

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