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

--

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

--

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

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 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

--

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

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

Spotify: 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 PODCAST:

🎙️ Unpack Pricing - Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more.

Apple: https://podcasts.apple.com/us/podcast/id1765716600

Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg

--

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/

Matty Mo's site: 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:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

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

--

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

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

Apple: 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/

Ryan Caldbeck's Pivoting CircleUp thread: 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

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:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

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

In The Arena is a part of the Turpentine podcast network. Learn more: www.turpentine.co

--

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 

Biotech founder and investor Martin Shkreli joins Jesse Genet and Erik Torenberg on In The Arena to dissect his controversies and crises through the lens of leadership. Martin goes deep into the decisions, mindset, and unforeseen logistics that led to him serving time in prison, the lessons he took away about tech and founding startups, and how he believes there is a hero’s journey arc up ahead. 

RECOMMENDED PODCAST:

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

In The Arena is a part of the Turpentine podcast network. Learn more: www.turpentine.co

RECOMMENDED PODCAST:

Econ 102 with Noah Smith and Erik Torenberg

Economist and Substack writers Noah Smith and Erik Torenberg make sense of what’s happening in the news, technology, business, and beyond, through the lens of economics. Subscribe to the show: https://link.chtbl.com/Econ102

TIMESTAMPS:

(00:00) Episode preview

(03:55) Perceptions of the media

(06:00) How the lawsuit impacted Martin's team

(09:40) How the government handled Shkreli’s case

(12:50) The day Martin was taken by authorities

(15:30) Hedge funds’ relationships with the law compared with venture

(24:15 The price hike and pharma industry norms

(29:45) Explanation of charges

(38:30) The new CEO

(41:00) New trope of private equity pharma

(47:30) The demise of the trust in the media

(54:20) Regrets and anger

(58:15) The epidemic of criminal injustice

(1:00:00) Being sued under the Sherman Act (monopoly law)

(1:03:26) Shkreli and Silicon Valley

(1:05:45) Entrepreneurship post-indictment

(1:13:00) Martin’s time in prison

(1:19:10) Martin reflects on being a repeat founder and where his passions lie now.

TWITTER: 

@wagieeacc (Martin)

@jessegenet (Jesse)

@eriktorenberg (Erik)

@inthearena_pod 

Sophia Amoruso reflects on being the poster child of entrepreneurship with Nasty Gal and Girlboss, going from the cover of Forbes to bankruptcy in a matter of months. Jesse Genet and co-host Erik Torenberg talk to Sophia about what it’s actually like at the red-hot center of the zeitgeist, how to assess your own leadership strengths and weaknesses, and how to rebound in your career and life.

RECOMMENDED PODCAST:

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

In The Arena is part of the Turpentine podcast network. Learn more: Turpentine.co

TIMESTAMPS

(00:00) Introducing Sophia Amoruso

(01:49) Describing Nasty Gal’s turning point 

(05:00) Missed opportunities to exit: “I would have taken the money”

(08:00) How helpful is the team of C-level executives around a founder?

(12:00) Leadership burnout

(14:20) Tension between the rough waters at Nasty Gal and the success of Sophia’s book Nasty Gal

(16:33) Sponsor: Pesto.tech for remote developers

(20:00) Girlboss backlash: “If you stand for something, people will use it against you.”

(24:00) Politicization of Girlboss

(27:00) Toxic culture from a founder perspective

(31:00) Sophia’s support to other female founders who were taken down

(33:00) How do you defend yourself in the public arena?

(35:02) Accountability and lessons for what Sophia is doing now

(37:15) How to avoid entrepreneurial mistakes

(39:00) Sophia’s advice for other entrepreneurs

(41:40) Sophia’s mindset as an investor and advisor

LINKS:

Trust Fund VC https://www.trustfund.vc/

TWITTER:

@sophiaamoruso (Sophia)

@trustfundvc (Trust Fund)

@jessegenet (Jesse)

@eriktorenberg (Erik)

@InTheArena_Pod

SPONSOR:

Head to Pesto.tech if you want to hire remote developers today!

Nathaniel Whittemore is the host of The Breakdown, the world’s biggest daily crypto podcast, and a former Marketing and Strategy Specialist at FTX. Nathaniel took no part in the activities that led to FTX’s downfall, but his insights and observations are equal parts horrifying and enlightening. Host Jesse Genet and Co-host Erik Torenberg talk to Nathaniel about the internal culture and comms at FTX during the crisis, SBF’s lies, as well as red flags and lessons he took away from witnessing the crisis unfold. 

RECOMMENDED PODCAST:

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:

(00:00) Introducing Nathaniel Whittemore

(02:05) Setting the scene for FTX’s collapse from $40 billion to nothing 

(06:55) Twitter debacle and FTX’s comms

(08:29) The FTX Slack during the crisis

(11:33) The emergency raise

(12:31) Who do you tell first about the crisis?

(14:40) FTX employees discover Binance acquisition through SBF’s Twitter

(15:20) Internal comms 

(18:10) SBF encouraging employees to keep their money on FTX

(19:44) HR at FTX

(24:11) When did employees turn on SBF?

(26:18) What was normal about FTX from a startup lens?

(31:14) Red flags to keep in mind

(34:58) Effective altruism culture at FTX

(36:21) Employees taking money out of FTX

(37:42) Is there anything that could’ve been saved at FTX?

(41:37) Doing things differently after witnessing the FTX crisis

(45:54) Evaluating SBF

(50:27) SBF’s confidantes and what might be next for SBF after serving his sentence

(55:02) Bouncing back after FTX

LINKS:

The Breakdown: https://nlw.substack.com/

TWITTER:

@nlw (Nathaniel)

@BreakdownNLW (The Breakdown Podcast)

@jessegenet (Jesse)

@eriktorenberg (Erik)

SPONSOR:

Head to pesto.tech if you want to hire remote developers today

Austen is the CEO and founder of BloomTech, an education platform famous for pioneering income sharing agreements instead of charging tuition. His company has forever altered thousands of students' lives for the better, but having a huge positive impact doesn't make actually running and growing a company easy. Host Jesse Genet and co-host Erik Torenberg talk to Austen about navigating legal and regulatory minefields, shifting internal culture amidst layoffs, and mental models for resilience.

RECOMMENDED PODCAST:

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:

(00:00) Introducing Austen Allred, CEO of BloomTech

(02:48) Setting the scene for BloomTech’s pivotal moments

(07:42) Sponsor: Pesto.tech

(08:21) Layoffs and aftermath

(11:08) Resetting internal culture

(13:18) Making decisions amidst ambiguity

(16:20) Lawsuit, regulations, and company name change

(28:28) Compartmentalizing as a CEO

(33:20) Mental models for “running into the darkness”

(40:27) Companies that execute their PR really well

(46:30) Hiring with a selection filter

(54:34) Hard Choices Officer

TWITTER:

@jessegenet (Jesse)

@eriktorenberg (Erik)

@austen (Austen)

@InTheArena_pod

SPONSOR:

Head to Pesto.tech if you want to hire remote developers today

Emil Michael was the Chief Business Officer at Uber during their meteoric and incomparable growth from 2013 to 2017, as well as CEO Travis Kalanick’s right hand. Few leaders in tech have accomplished so much in terms of raw users and revenue growth. Few leaders in tech have also personally experienced so much turmoil. Host Jesse Genet and Co-host Erik Torenberg talk to Emil about the #DeleteUber campaign, Uber’s unsuccessful bids to acquire Lyft, doing business in China, and more from inside Uber.

RECOMMENDED PODCAST:

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:

(00:00) Introducing Emil Michael, CBO of Uber from 2013-2017.

(02:27) Setting the scene for #DeleteUber crisis

(11:05) Lyft

(11:32) The Trump White House invitation

(13:02) Sponsor: Pesto.Tech

(13:42) Internal dynamics at Uber

(20:35) China

(30:17) Unsuccessful deals

(34:03) Tim Cook and Apple

(38:42) Hiring lessons

(41:39) Most misunderstood notion about Uber

(45:44) SWAT team episode

(47:30) Emil’s advice for overcoming a crisis

TWITTER:

@jessegenet (Jesse)

@eriktorenberg (Erik)

@emilmichael (Emil)

@InTheArena_pod * DM us if you have suggestions for who we should interview on In The Arena

SPONSOR:

Head to pesto.tech if you want to hire remote developers today.