The AI Founder Rollercoaster: Fun If You Like Fear
A four-hour flight with no Wi-Fi gave me the perfect excuse to reflect - and write about what life as an AI founder actually feels like. (It’s also a decent cure for plane boredom)
TL;DR: Some days I can’t imagine doing anything else. Other days I wonder what I’m doing.
A rollercoaster is the perfect analogy - you're there because you want to be, but you're often afraid, and there's parts when it goes up and moments when it goes down.
Every week, especially in AI, is a mind-bender - it might be major platforms commoditising features like yours, new well-invested startups in a similar space coming with innovative ideas - but in case you're in the same boat, actually that's REALLY good...
The more you can see the red ocean, the more you can focus on the elements of your business that allow you to swim to the warmer, calmer blue seas.
Here’s what I’ve learned so far:
🔻 The downs
Sleep debt is real (my new Ultra 3 watch doesn’t lie). Does anyone here actually not do insane hours and days? Not said with pride, said with 'is there another way' energy?
SaaS costs are a chokehold (special mention to HubSpot, their pricing paths are infuriating, but I respect them as someone now thinking about that type of thing)
Customer feedback doesn't grow on trees. "Talk to your users every day" is the wisdom, it's not that easy. People are people, people are busy, so finding ways to get rich insights is another job on top of the job.
Momentum feels addictive - and fragile.
Fundraising is basically Tinder. Fun fact, it took me 4 years to get my (now) wife to go on a date with me, so I'm ready for this game.
🔺 The ups
Evolution is exciting: Meet-Ting went from closed beta → open beta → WhatsApp in 2 months.
The shark infested waters of the last two months (Perplexity, ChatGPT, YC-backed companies helped us see a blue ocean right in time for our next phase)
Freedom to build and market how we life: plain-English T&Cs, build in public and share data openly, fun SaaS videos.
The founder community is awesome, especially here on PH. We've got some really great virtual relationships going on and just connected with another PH company to potentially partner on a technical problem
⚖️ Somewhere in the middle
Luck. A big partnership fell through Friday → Monday night, one of the biggest tech companies in the world emailed to pilot. That’s the ride, but my heart rate struggles.
Founder life is toxic fun. Equal parts fear + excitement, just like a theme park.
Wouldn’t change it (most days).
Full blog here on our Substack: https://chiefting.substack.com/p/the-founder-rollercoaster-fun-if
If you’re thinking about starting your own journey, my DMs are open.
If you also just want to vent, same DM open to you!
-Dan
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