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Eoghan McCabe: uncertainty

21 Aug 2025 Lenny's Podcast How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

“Now, it's okay to wrap things up and quit, but when you kind of run away, like I kind of had to because I was sick and burned out and kind of disenchanted, I don't know, it didn't feel good.”

— Eoghan McCabe

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Everything needed to verify it.

Speaker
Eoghan McCabe
Attribution
Verified speaker
Claim type
uncertainty
Recorded
21 Aug 2025
Publisher
Lenny's Podcast

Transcript context

…Yeah, so this whole period sounds very stressful for you. Did you ever regret coming back and just like, what the hell did I get myself into? What am I doing to myself? I never regretted coming back, but I have many moments where I don't enjoy the job. I didn't regret coming back because it was deeply cathartic for me. When a founder runs away from their business, it is the ultimate betrayal of their heart and the dream that they have. Now, it's okay to wrap things up and quit, but when you kind of run away, like I kind of had to because I was sick and burned out and kind of disenchanted, I don't know, it didn't feel good. So, especially when I had done that, having betrayed in a million or a thousand small ways, my intuition, there was something I needed to exercise. So, it has been deeply meaningful in that respect. And then of course, I'm fortunate that it worked out. I get to be on the second most popular podcast in tech. I get to pat myself on the back in front of all these people. Who wouldn't want that? That said, the reality is that for particularly people like me who like the adventure and the high agency being unilateral, day-to-day movement where you're trying to make big, wild, bold decisions, the reality is that if you're successful, most of your days will not be that. It'll be reviewing the bonus policy for next year and reviewing the comp proposal for your execs for the next year. It will be showing up for accountability meetings and stepping through the status of different work streams. It'll be rushing from meeting to meeting, having 8, 9, 10 meetings a day. I don't happen to believe that that's a great way to live your life. It'll be trying to get to all the emails you need to get to such that all those people aren't offended and hurt and trying to communicate in the ways with your staff and your team that is empathetic and thoughtful and keeps in mind that they may be having as shit a day as you are. You're giving me an opportunity to paint story of this maverick led adventure that you might imagine in a comic. I'm for some reason picturing TinTin sail the seas, this swashbuckling adventure. It's not. It's corporate life kind of sucks particularly for people like me. So, I have many of those days, and so the only reason I'm still around is that I have a broader mission that makes it worthwhile for now, but that's why you see so many of our best founders get to a point where they're like, okay, I've had enough corporate fun. So, that's the most authentic answer I could give you. No regrets coming back, but plenty of pain on a day-to-day basis. Today's episode is brought to you by DX, the developer intelligence platform designed by leading researchers. To thrive in the AI era organizations need to adapt quickly, but many organization leaders struggle to answer pressing questions like which tools are working, how are they being used, what's actually driving value? DX provides the data and insights that leaders need to navigate this shift. With DX, companies like Dropbox, Booking.com, Adyen and Intercom get a deep understanding of how AI is providing value to their developers and what impact AI is having on engineering productivity. To learn more, visit DX's website at getdx.com/lenny, that's getdx.com/lenny. One of the interesting things about this space of agents, there's all this talk, agents are taking over. It's the future of software. SaaS is going to be replaced with agents. CX is a classic. It just feels like, I imagine looking forward, it was not obvious. Now looking back, it's like obviously this is an amazing place for agents to take over work, but there's always this talk of agents will do everything and all the SaaS software is going to be replaced by agents. Do you have a sense of just how far this disruption will go outside of CX because it's already happening in your businesses?…

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