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Grit · 3 min · Mar 9, 2026
Sierra chose financing partners over the highest valuation
Sierra passed on higher offers in all three rounds and sizes capital to reach the next milestone. Bret Taylor weighs dilution against the revenue and growth needed for the next raise.
Bret Taylor is co-founder of Sierra.
Co-founded and leads Sierra, an enterprise AI agent company; chairs OpenAI's board and co-created Google Maps.

Joubin Mirzadegan, Host · Partner, Kleiner Perkins
Took Palo Alto Networks' cloud business from $2M to $50M+ ARR in a year.
About this segment
Sierra passed on higher offers in all three rounds and sizes capital to reach the next milestone. Bret Taylor weighs dilution against the revenue and growth needed for the next raise.
From “How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor”, Mar 9, 2026. Watch the full episode
Thanks. We'll look at and fix what's off.
“In fact, in all three of our rounds, we had higher valuations available that we didn't take.”
Bret Taylorat 48:54 · Grit48:54Takeaways
- Sierra did not take the highest valuation available.
- The capital target is tied to the next business milestone.
- Taylor prefers to plan with a buffer against unfavorable markets.
In this episode
Full episode- 11:55Leaders have to test internal stories against customers4:38
- 22:35Applied AI will rely on a portfolio of specialized models4:16
- 32:44AI's impact depends on task complexity and real-world bottlenecks5:51
- 52:40Paid proofs of concept filter out AI tourism5:38
48:13Sierra chose financing partners over the highest valuation3:05
- 38:52AI gains will fuel competition as well as efficiency5:45Up next
- 4:05Sierra pairs enterprise experience with AI-native graduates2:59
- 17:27AI is expanding contact-center demand while capital delays consolidation4:30
Transcript
Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.
- 48:17
highest valuation so you can have the least amount of dilution? Like, I'm curious, like, you know the let's take the market correction example like let's imagine that it happens this year and it happens meaningfully the counter argument to raising whatever a hundred at 10 billion is i'm just making up numbers but just for the story's sake um you you just have a proverbial gun to your head of a really big target that you have to hit at a valuation that was quite frothy at that given moment. So like, I'm more just like philosophically curious about how you think about it. We definitely don't choose the highest valuation. In fact, in all three of our rounds, we had higher valuations available that we didn't take. So factually, we definitely don't do that. We have a dilution that we care about, but within that range, we're choosing a partner
- 49:12
and that's how we think about it. But it is a generous valuation. The way I think about it is actually quite simple, um, which is how much capital do we need to grow, uh, into the next milestone, which, you know, might end in, in entering the public markets, but between that, it would be to have a revenue scale and growth rate to justify, to capitalize the business in the next round in a way that all of the existing cap tables happy, uh, with that outcome. And so the way I think about it is, you know, if you take the $10 billion valuation scale, what does it mean to sort of fill in that valuation what revenue scale and growth rate how much capital do we need to achieve that that's all it is and i think the uh so we're very much focused on like our business plan which is like how are we going to invest in uh you know the products and uh you know our go
- 50:05
to market teams to grow uh grow our revenue and it's a sort of a spreadsheet to be honest with That's how we think about it. And the unknowns, uh, but we just put a lot of, you know, air bands around it are, you know, the demand environment and competition. Um, though, you know, when you're a company like ours, you just assume you're going to, you know, remain the best product on the market, uh, which is not something you're entitled to, but like, that's why you exist. Um, and then similar things like there's a lot of unknowns around we've talked about, like, well, how many software engineers will we need to reach? I don't know. I have no idea. Um, but with usually what these things is you try to plan somewhat conservatively because the last thing you want to do is under capitalize your business and then be in an environment where you have to raise
- 50:48
money on terms that aren't favorable which has you know happened a lot but you don't want that to happen to you so we tend to sort of you know you put a bunch of padding in on different assumptions and run some contingency plans and all those other things and just make sure that you have enough capital to get to where you want to go to and by the way the reason why you know 100 it does sound but most companies aren't going 50 quarter over quarter either you know so that's the that's the dynamic and so i'm not sure it's right or wrong but i just mean like i i would