#03: The Workaholic Founder

Psss... have an Agency Horror Story? Say no more... (meaning, please, spill) TL;DR Workaholic founders, the cobra effect, and a laptop opened at the top of a mountain. Hola amigos! Ditching grind culture is no easy feat, especially for founders who wear their workaholic tendencies like a badge of honor. This week on The Agency Horror Show, we took on the founder who can’t switch off, and what it costs them, their team, and their business. AI Obsession: the productivity trap AI was supposed to give us our time back. Instead, we’re shipping more, faster, around the clock. Mila: A reflection from my mentor Itai has stuck with me: “The fact that AI can ship more doesn’t mean that we have to ship more.” It reminds me of the cobra effect: pay a bounty for dead cobras and people start farming cobras. AI is doing the same to our time. Treating your job as your hobby sends the wrong signal to your team. “Your brain needs it. Period.” (Mila) Pilar: As a former workaholic, I can tell you this pressure doesn’t appear overnight. Start by asking why you’re running this business in the first place. Takeaway: if creativity strikes on a Sunday, take Monday back. Kids with a Wallet: what are you actually measuring? Workaholic founders usually measure success in revenue and team size. Mila has started asking how we’re measuring success and plans to add it to her discovery calls. “One founder told me, ‘I’m measuring my success as an agency by whether my team is happy or not.’ I find that really inspiring.” (Pilar) Pilar: Companies like Patagonia show that slow, sustainable growth is possible. We both think we’re at the end of an era, and more people are choosing enough over the ladder. “The best thing about founding your own thing is you get to set the rules.” (Pilar) Confession Booth: the most unhinged workaholic founder stories Mila: a founder who proudly said he loves that his employee will reply at 3 a.m. I cried on the inside. Pilar: a founder who finally took the weekend off to hike a mountain, then: “I got to the summit, opened my laptop, turned on my hotspot and started closing tasks.” Mila’s (very serious) advice: “It’s not cute, it’s not attractive. You have a problem.” Timestamps 00:00 Intro and a Happy Friday 00:20 LinkedIn Crush, Cringe and Crash 00:38 Cringe: “Hinge-In” and the windmill beach photos 02:37 Crush: PAAW, the for-profit dog rehoming company 04:15 Why dog and cat photos belong on LinkedIn 04:55 Today’s theme: workaholic founders 05:50 AI Obsession: workaholism across cultures 06:50 “My job is my hobby” and the message it sends 09:12 Why agencies replicate the corporate pressure 09:50 Pilar’s story as a former workaholic 11:33 When the agency becomes the founder’s identity 12:44 The micromanaging workaholic and AI’s inhumane pace 15:07 The cobra effect: AI saves time, we ship more 17:01 Kids with a Wallet: how founders measure success 17:54 Revenue and team size vs. profit 19:50 Adding “How do you measure success?” to discovery calls 21:42 The “grow uncontrollably” narrative and Patagonia 23:52 Founders choosing team happiness over revenue 24:42 The end of an era: “enough” over the ladder 26:59 You get to set the rules 28:17 Submit your agency horror story 29:00 Confession Booth: the most unhinged moments 29:40 “I can message them at 3 a.m. and they’ll reply” 30:22 The weekend off that ended at a mountain summit 32:00 Wrap-up and outro