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.
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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
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
