"In The Arena"

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 [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 [https://open.spotify.com/episode/7H9Q0Cbudh3DeIKTzjTHBc?si=5HyYcAXRTxemSGNP9tzZ4Q] -- RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw [https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw] Apple: https://podcasts.apple.com/podcast/id1762756034 [https://podcasts.apple.com/podcast/id1762756034] - 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 [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 *

Ryan Hudson, the co-founder of Honey (which sold to PayPal for $4B in 2019) sits down with Jesse Genet and Ryan Caldbeck for a rare interview about his rollercoaster trajectory, so emblematic of the startup struggle - but with an M&A ending. Ryan dives into what it was like at the startup's early days when Honey was unattractive to investors, the great personal risks he undertook to keep working on the company, the chaos of being directly targeted by Amazon in the weeks leading up to closing the PayPal deal, and gives us a revealing look at what it's actually like getting acquired. Ryan Caldbeck, guest on episode 7 of In The Arena, is the perfect co-host for this conversation: a startup founder and CEO himself, who is also well known on tech Twitter for discussing founder mental health. -- RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw [https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw] Apple: https://podcasts.apple.com/podcast/id1762756034 [https://podcasts.apple.com/podcast/id1762756034] - 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 [https://link.chtbl.com/hrheretics] Catch up on Ryan Caldbeck's episode: “Terrifying Growth”, Managing Mental Heath, and Radical Sharing Apple: https://podcasts.apple.com/us/podcast/e7-ryan-caldbeck-on-terrifying-growth-managing-mental/id1691530886?i=1000623146998 [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 [https://open.spotify.com/episode/7H9Q0Cbudh3DeIKTzjTHBc?si=5HyYcAXRTxemSGNP9tzZ4Q] TIMESTAMPS: (01:00) Episode Preview (04:15) Honey under siege from Amazon (11:07) Could the Amazon action endanger the Paypal acquisition? (17:15) Was Ryan lucky or unlucky to have closed an M&A deal right before the pandemic (21:00) How do you tactically handle the moment conversations turn to a potential acquisition? (23:19) How do you set a price? (26:00) Honey didn’t want to sell (29:30) Smoothest exit in history? (36:40) Co-founder relationship tested during the stressful moments (38:55) Leaving as Honey’s co-founder to go be a Product Manager at another company (41:24) $5,000 in the bank and supporting 3 kids (47:09) How Honey finally began earning revenue (52:57) How to design a deeply aligned Co-Founder relationship (57:24) What to look for in a co-founder (01:03:00) Why firing employees is such a painful practice in fast-growing companies (01:09:30) Controversial influencer marketing strategy and crisis comms X:  @ketau (Ryan Hudson) @ryan_caldbeck (Ryan Caldbeck) @jessegenet (Jesse) @eriktorenberg (Erik) @inthearena_pod

Oren Aks was a designer at Fuck Jerry Media, the agency behind the signature marketing of the now-infamous Fyre Festival of 2016. In this episode, Oren recounts his ground-level realization that the festival was a fraud, sharing new details about the debacle chronicled in two documentaries. Oren also tells us about the backlash he experienced after the festival, shares his well-earned lessons around trust, and offers perspective about our cultural fascination with failure. Jesse Genet is joined by a special guest co-host Matty Mo, an artist who made headlines for putting on a fake fire fest as satire in Los Angeles.  -- RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw [https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw] Apple: https://podcasts.apple.com/podcast/id1762756034 [https://podcasts.apple.com/podcast/id1762756034] -- Catch up on host Jesse Genet’s own crucible moments from her entrepreneurial story in Episode 6: Spotify: https://open.spotify.com/episode/3HQKu4vbaIuAvhgKLBuyYk?si=UYb2aGlJTxynO_B8UzMkUQ Apple: https://podcasts.apple.com/us/podcast/e6-host-jesse-genet-on-selling-her-startup-lumi-while/id1691530886?i=1000622369978 TIMESTAMPS: (00:00) Episode preview (03:00) How Oren and co-host Matty first met (04:35) Oren relives landing at Great Exuma for Fyre Fest (13:30)The social distortion field Oren witnessed at Exuma (17:00) Distraction efforts and the angry mob (20:55) Things take a turn (34:20) Processing the failure while Oren was on the island, and then back in NY (44:30) The documentaries (45:25) The red flags in hindsight (49:00) Financial breadcrumbs (54:00) The orange square and power of social proof (01:00:20) Billy McFarland’s new thing (01:05:18) Why the Fyre Festival has lasting power in the zeitgeist of colossal failures LINKS REFERENCED: Oren Aks agency Atomic Milk: http://www.atomicmilk.com/ [http://www.atomicmilk.com/] Matty Mo's site: https://www.themostfamousartist.com/ [https://www.themostfamousartist.com/] X: @fyrefestival (Oren runs this now) @jessegenet (Jesse) @mostfamousartist (Matty) @inthearena_pod *

Ryan Caldbeck is a tech founder, investor, and former CEO of CircleUp, which raised over $50M in venture capital during his tenure. Ryan is especially well known for his personal writings in the form of thought-provoking twitter threads where he chronicles his struggles with mental health, extreme leadership pressures, and sheds light on conflicts with investors. We dive into all this and more, including his experiences replacing himself as CEO while battling cancer. -- RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw [https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw] Apple: https://podcasts.apple.com/podcast/id1762756034 [https://podcasts.apple.com/podcast/id1762756034] -- In The Arena is a part of the Turpentine podcast network. Learn more: www.turpentine.co RECOMMENDED PODCAST: Turpentine VC: Delve deep into the art and science of building successful venture firms through conversations with the world’s best investors and operators. Subscribe wherever you get your podcasts: https://link.chtbl.com/TurpentineVC [https://link.chtbl.com/TurpentineVC] Catch up on host Jesse Genet’s own crucible moments in her entrepreneurial story in Episode 6: Spotify: https://open.spotify.com/episode/3HQKu4vbaIuAvhgKLBuyYk?si=UYb2aGlJTxynO_B8UzMkUQ [https://open.spotify.com/episode/3HQKu4vbaIuAvhgKLBuyYk?si=UYb2aGlJTxynO_B8UzMkUQ] Apple: https://podcasts.apple.com/us/podcast/e6-host-jesse-genet-on-selling-her-startup-lumi-while/id1691530886?i=1000622369978 [https://podcasts.apple.com/us/podcast/e6-host-jesse-genet-on-selling-her-startup-lumi-while/id1691530886?i=1000622369978] TIMESTAMPS: (01:00) Episode Preview (04:00) The inflection point when Ryan decided to pivot  (08:59) “Terrifying growth” (11:35) Vulnerability with the board vs vulnerability with the executive team (16:00) How transparent should a leader be? (20:50) Ryan’s hindsight about vulnerability (26:55) 2019: Ryan starts to post publicly on Twitter (28:25) How to deal with feeling bad about yourself (37:30) A real leader never quits (42:33) Dark side of VC (46:00) Ryan's feedback email to one of his investors LINKS REFERENCED: Ryan Caldbeck's writing https://ryancaldbeck.co/ [https://ryancaldbeck.co/] Ryan Caldbeck's Pivoting CircleUp thread: https://twitter.com/ryan_caldbeck/status/1118288136918847488?lang=en [https://twitter.com/ryan_caldbeck/status/1118288136918847488?lang=en] Hard Things About Hard Things: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1690962629&sr=1-1 [https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1690962629&sr=1-1] X:  @ryan_caldbeck (Ryan) @jessegenet (Jesse) @eriktorenberg (Erik) @inthearena_pod

On today’s episode, In The Arena's very own Jesse Genet is in the hotseat. Jesse dives into her biggest crucible moment as the CEO of Lumi: deciding to halt a Series B fundraise and navigating the subsequent conversations with the board, employees affected by layoffs, and acquirers. RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw [https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw] Apple: https://podcasts.apple.com/podcast/id1762756034 [https://podcasts.apple.com/podcast/id1762756034] In The Arena is a part of the Turpentine podcast network. Learn more: www.turpentine.co [www.turpentine.co] -- RECOMMENDED PODCAST: 🎙️ Second Opinion - A new podcast for health-tech insiders from Christina Farr of the Second Opinion newsletter. Join Christina Farr, Luba Greenwood, and Ash Zenooz every week as they challenge industry experts with tough questions about the best bets in health-tech. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211 [https://podcasts.apple.com/us/podcast/id1759267211] Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv [https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv] TIMESTAMPS: (00:00) Episode Preview (02:31) Saying no to the fundraise (08:04) What happened after deciding to go against the board? (10:03) The moment Jesse realized she couldn't proceed with the Series B (12:01) How the board received Jesse's decision (14:08) Podcast Rec: The Limited Partner podcast (14:44) Reliving Jesse’s lowest low moment (16:53) How to conduct a layoff (20:05) Picking up the pieces after Lumi’s layoffs (23:01) Lumi's founding story (25:43) The acquisition process (28:53) Jesse's pregnancy during Lumi's transition and acquisition X / TWITTER:  @jessegenet (Jesse) @eriktorenberg (Erik) @inthearena_pod