11 episodes

In The Arena is where entrepreneurs and leaders share stories of the biggest crises of their careers and lives – and how they made it through. Host (and founder herself) Jesse Genet goes beyond the headlines to interview leaders about the most challenging moments they've ever faced – from total business collapse, to public scandals, even being sentenced to prison. Along with special guest co-hosts, In The Arena revisits the crucible experiences and reveals what it was actually like in the room. Most importantly, leaders share how they bounced back from the brink, offering advice, mental frameworks, and earned wisdom for any aspiring leader.
In the Arena is part of the Turpentine podcast network. Learn more: turpentine.co

"In The Arena‪"‬ Turpentine

    • Business
    • 4.8 • 16 Ratings

In The Arena is where entrepreneurs and leaders share stories of the biggest crises of their careers and lives – and how they made it through. Host (and founder herself) Jesse Genet goes beyond the headlines to interview leaders about the most challenging moments they've ever faced – from total business collapse, to public scandals, even being sentenced to prison. Along with special guest co-hosts, In The Arena revisits the crucible experiences and reveals what it was actually like in the room. Most importantly, leaders share how they bounced back from the brink, offering advice, mental frameworks, and earned wisdom for any aspiring leader.
In the Arena is part of the Turpentine podcast network. Learn more: turpentine.co

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

    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

    RECOMMENDED PODCAST:
    Turpentine Finance  
    Host Sasha Orloff (3x Founder & CEO) is joined by top founders and finance leaders at high growth tech companies who share how they navigated huge make-or-break decisions, rode inflection points, and architected success. If you want to learn the mental models and tactics top business leaders and CFOs, subscribe below. Debut episode features Casey Woo unpacking his wild ride managing billions in budgets at WeWork  – arguably one of the craziest capital stories ever.

    Listen on Spotify: https://open.spotify.com/show/5BflNhFxxLjqT2RA47352G 
    Listen on Apple: https://podcasts.apple.com/us/podcast/id1704418764
    -
    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

    • 1 hr 23 min
    E9: Ryan Hudson of Honey on Being Targeted by a Tech Giant, Getting Acquired for $4B, and the Great Personal Struggles Founding a Company No One Will Fund

    E9: Ryan Hudson of Honey on Being Targeted by a Tech Giant, Getting Acquired for $4B, and the Great Personal Struggles Founding a Company No One Will Fund

    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:
    Turpentine Finance  
    Host Sasha Orloff (3x Founder & CEO) is joined by top founders and finance leaders at high growth tech companies who share how they navigated huge make-or-break decisions, rode inflection points, and architected success. If you want to learn the mental models and tactics top business leaders and CFOs, subscribe below. Debut episode features Casey Woo unpacking his wild ride managing billions in budgets at WeWork  – arguably one of the craziest capital stories ever.

    Listen on Spotify: https://open.spotify.com/show/5BflNhFxxLjqT2RA47352G 
    Listen on Apple: https://podcasts.apple.com/us/podcast/id1704418764
    -
    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

    • 1 hr 18 min
    E8: Oren Aks on Marketing the Fyre Fest, the Infamous Cheese Sandwich, and Why Our Culture Can’t Look Away from Colossal Failure

    E8: Oren Aks on Marketing the Fyre Fest, the Infamous Cheese Sandwich, and Why Our Culture Can’t Look Away from Colossal Failure

    Oren Aks was a designer at F**k 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:
    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 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

    • 1 hr 14 min
    E7: Ryan Caldbeck on “Terrifying Growth”, Managing Mental Heath, and Radical Sharing

    E7: Ryan Caldbeck on “Terrifying Growth”, Managing Mental Heath, and Radical Sharing

    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 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:
    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 

    • 54 min
    E6: Host Jesse Genet on Selling Her Startup Lumi While 8 months Pregnant

    E6: Host Jesse Genet on Selling Her Startup Lumi While 8 months Pregnant

    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 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 PODCASTS:
    On The Limited Partner Podcast we discuss Venture Capital through the lens of Limited Partners. Join us for conversations that are normally held in stealth. Head to https://link.chtbl.com/thelimitedpartner to listen on the platform of your choice!

    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 

    • 36 min
    E5: Martin Shkreli on public vilification, leadership lessons from prison, and getting back in the arena

    E5: Martin Shkreli on public vilification, leadership lessons from prison, and getting back in the arena

    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 

    • 1 hr 20 min

Customer Reviews

4.8 out of 5
16 Ratings

16 Ratings

oppie12345 ,

jesse is a fantastic host

the depth of the conversations on this show and the real-life, in-the-trenches stories she pulls out of her guests is so valuable!! much needed podcast admist all of the other tech shows

jackiekoch ,

Insider View!

What a great podcast to learn the real stories and lessons learned of growing a business. They ask the right questions that hit on the real struggles founders face. A new favorite!

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