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

"In The Arena"

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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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