#5: Ego death

Got an agency horror story? Spill here! TL;DR: We unpack why founders struggle to hear criticism, how AI can become an ego-boosting yes-man, and what happens when a CEO asks for feedback and absolutely cannot handle it. Hola amigos! What if the biggest thing standing between your agency and its growth is your own ego? This week, we're talking about the uncomfortable art of admitting you're wrong, letting other people take the wheel, and resisting the temptation to ask a chatbot to tell you how brilliant you are. AI Obsession: Is AI feeding your ego? We kicked off with a question: why is it sometimes easier to hand an AI agent access to important decisions—or even bank credentials—than to delegate to a human? Maybe machines feel easier because they have no egos or feelings to manage. But LLMs can also be yes-men, reflecting our ideas back at us and making us feel even more brilliant. Pilar: LLMs are usually a yes man. If you only listen when AI agrees with you, you're talking to a mirror. Mila finds it useful for preparing delicate conversations and understanding cultural context in multicultural teams. But growth happens when humans disagree and make ideas better. Kids with a Wallet: The cost of not knowing Money can be especially hard to talk about honestly. Admitting you've mismanaged it can feel like admitting you don't know what you're doing, so it's tempting to pretend the numbers don't matter—or celebrate revenue without looking at what you're spending. Pilar shares how much respect she has for founders who can admit they've made bad investments or got into debt, then ask for help. Whether that means finding a bookkeeper, bringing in a finance person, or learning what went wrong, humility is the starting point. Mila: I think it's very hard to be radically candid when it comes to the numbers. A business can't outgrow a founder who refuses to learn, delegate, or let go. It should eventually run without you—not stay your baby forever. Confession Booth: Please don't ask for feedback you can't take This week's anonymous confession is a meeting from hell. A CEO gathered a group to brainstorm how to turn around an underperforming project. But when the team started giving the feedback they'd been invited to share, the CEO got defensive, started yelling, and accused one person of doing nothing. That person yelled back. So much for a safe space. Mila: You are just assuming the other person won't notice, and you're wasting their time. We saw a lack of psychological safety, unclear expectations, and a project handed down rather than genuinely shared. In a brainstorm, people need to speak honestly. Leaders must model the behaviour they expect, or the rules only apply to some people. Got an agency horror story? Send us an anonymous confession through the link in the show notes. You can share a video, voice note, or just type it out—we'll respect your wishes. Timestamps 00:05 Intro 01:15 LinkedIn Crush/Cringe/Crash 01:25 Cringe: creepy outreach 03:01 Crush: Eugene Healy on marketing 06:09 This week's theme: ego death 09:49 AI Obsession: delegating to AI vs. humans 13:33 AI, bias, and the mirror effect 17:18 Using AI to prepare hard conversations 19:24 Kids with a Wallet: ego and money 21:33 Self-awareness and transparency 22:29 Asking for help with financial mistakes 25:49 Letting go so the business can grow 27:02 Growth means growing as a person 29:00 Confession Booth: a CEO loses it 29:22 Send us your agency horror stories 30:01 The confession: feedback gone wrong 32:27 What the story reveals about ego 34:37 Company culture and psychological safety 36:23 Values, code of conduct, and leading by example 38:21 Outro and final horror-story call