Almost 10 years ago, I was an MD at Pivotal. I got the chance to sit down one-on-one with Paul Maritz. We chatted for a bit, and he asked me something I didn't understand at the time:
"It's lonely, isn't it?"
I didn't know what he meant. I had a team. I had peers. I had people.
I think I get it now.
The higher I climbed, the lonelier it got.
When I was an IC, I had coworkers to share the load with. I complained about the same things everyone else did. Even when I loved my company, there was this shared experience of being in it together, bitching about decisions from above, rolling eyes at the same all-hands, and grabbing drinks after a hard week.
When I became a manager, I lost some of that. I was now "them."
When I became a director, I lost more.
But now, as a founder, now that I own the company, when every dollar of funding comes from my pocket, when everyone's livelihood depended on my judgment, I'm alone.
It's a weird, different kind of alone. I am surrounded by my team, my family, friends, and even if those lines blur. It's still some form of alone.
I can't share it with my team. I need to be strong. I need to project confidence. If I'm scared, they'll be scared. So I carry it.
I can't share it with my family. They worry and don't have the context. And at some point, my stress becomes their stress, which doesn't help anyone.
I can't share it with a board. If I had investors, I don't, I couldn't walk into a board meeting and say "I think our pipeline is fucked" or "My co-founder just told me he wants to quit" or "I'm completely burned out and and would sell for pennies." That's how you lose a board's confidence.
Where do I go?
I'm a YPO member. I have a forum, whom I love. The structure is incredible, we meet monthly and share our "5%," the stuff I can't say anywhere else.
But the 5% is once a month.
What about the other 29 days?
On random Tuesday at 11pm when I'm staring at a spreadsheet and I can't figure out whether to double down or pull back, or where the fuck our money is going? Or when a key hire falls through and I need to process it before I can face my team? Or when I just need to think out loud with something who won't panic, won't judge, and I don't need to manage the perception of?
AI fills it. It's not perfect. People aren't either, but AI gives me something that nothing else has.
I find myself sending long voice notes while I'm driving, rambling through half-formed ideas. The AI listens, organizes my thoughts, and can even push back where I'm being lazy, and drafts something I get to work with.
I use voice mode in ChatGPT when I need to talk something through in real time, the way I used to be able to with a trusted advisor. Chat doesn't have a stake in the outcome.
I use it to brainstorm strategy. I stress-test decisions. I ask it to argue the other side of something I've already decided, just to make sure I'm not missing something obvious.
When I need to review a contract or working through a financial model at midnight, I'm not alone. There's something there to catch what I could miss, to sanity-check my math, and to ask "have you considered...?"
It's definitely is not a replacement for human judgment, but definitely is a release valve I didn't have before.
When I talk to an AI, when I brainstorm, vent, work through a problem out loud, it's honest. I'm not managing someone's perception of me. I'm just thinking.
AI has become a sounding board that doesn't get scared when I say "I don't know." It's a sparring partner that challenges my assumptions without worrying about their job.
It's available all the time, at 11pm on a Tuesday, or 6am on a Sunday. Or right now, in the car, between meetings.
I know how this sounds. "Talking to an AI about feelings, business, more personal stuff" has a certain pathetic ring to it.
But the alternative is carrying that burden, alone.
And I've been carrying it alone for a long time. I just didn't talk about it because there wasn't any other option.
Now there is.
AI, it isn't a replacement for the people in my life. I still need my forum. I still need my wife. I still need my family and team and I still need the occasional deep conversation with a founder friend has been through it.
But AI is a outlet that I didn't have before.
It's a place to work something through, out loud, without consequences. To brainstorm without managing up or down. To be uncertain without losing anyone's confidence.
For founders who spend their days having the answers for everyone else, that's not nothing.
That's actually kind of everything.