Discussion

• @annbordetsky Ann Bordetsky on x

  @jasonlk Balanced take here, really well articulated on all sides Founders have to play the game on the field but the mercenary risk is very real

• @mrp Ron Pragides on x

  HUBRISTIC FUNDRAISING “Brex raised $300 million at a $12.3 billion valuation in October 2022—technically 2022, but really the tail end of the 2021 madness before rates spiked and everything crashed. At that valuation, with maybe $200-250M in revenue at the time, Brex was being [i…

• @alexfmac Alex Macdonald on x

  Thoughtful piece... but for most VCs the incentives encourage hubristic fundraising. This isn't really a founder problem... it's a VC problem. Also a few ‘modern day AI’ hubristic comps do not deserve to be in the list 👀

• @parkerconrad Parker Conrad on x

  @jasonlk I think this is very smart / very much on-point. It can be very dangerous not to play the game on the field though - if your competitors are doing this and you are not, it can be very hard to survive.

• @elwatto Miguel Carranza on x

  Fantastic and balanced piece. It's less about right vs wrong and more about understanding tradeoffs and the rules of the game. It's always a lot more nuance than the average, simplistic twitter/hn take. PS: If you ever get the chance, take Jason's check.

• @markmacleod_ Mark MacLeod on x

  Brilliant and balanced take on the Brex acquisition

• @trace_cohen Trace Cohen on x

  Great post that sums up the current tech/VC market and the games being played.

• @alexiskold Alex Iskold on x

  Epic post by @jasonlk Know the trade off If you roll the dice and stumble you won't capture all the upside But obviously still an epic outcome for founders, early employees and early investors With AI companies unlike with Brex unit economics will be another big variable.

• @jamesreggio James Reggio on x

  This is a really good piece - especially because it honors the folks who stuck around to make this turnaround happen.

• @jasonlk @jasonlk on x

  Brex and The Pros and Cons of Hubristic Fundraising

• @jesskah Jess Lee on x

  We have entered the vibe raise era

• @rabois Keith Rabois on x

  This post is very good. (He will regret the comments re Ramp however; Ramp is massively undervalued actually.)

• @shaig Shai Goldman on x

  I've been in the startup game for a minute, there is a very wide delta between private market valuation & public valuations , especially at this moment. Worth a read if you are a founder who is raising.

• @arampell Alex Rampell on x

  @jasonlk My observation is that secondaries have really altered the dynamic Founders can understand that fundraises should be organized for monotonic growth with great investors to get to a great final/max destination It's hard (when they're selling along the way) to take a lower…

• @fredsoda @fredsoda on x

  My only qualm with this article is the claim that, say, Loveable is “worth” more than Brex. Brex sold for $5.15B. Loveable is “worth” $6.6B. If early-stage valuations are hype; late-stage valuations are fake.

• @bgurley Bill Gurley on x

  This is quite well written; important reflection on the current environment. I would add one more thing. Most of these rounds are preemptive. The investor suggested it - it wasn't the company's initiative. A finance form of the observer effect. https://grokipedia.com/...

• @rakeshsfnyc Rakesh Agrawal on x

  I have no idea what bilt modeled, but once they take away the unsustainable giveaway, all those people are going to churn off. They had a deal that was too incredible to be true. That they couldn't buy the back book is even more damning. They have to reacquire those customers.

• @rakeshsfnyc Rakesh Agrawal on x

  My approach to real arr projections: if you are selling primarily to startups, you should discount by likelihood they will still be around in out years. Hint: they won't. And the degree to which you are giving away money. If your product sells for below your token costs, of