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It's not weird at all. Brian talked to a ton of people over many months. He was raising many months before I met him. And then I came in. I then spent too long

It's not weird at all. Brian talked to a ton of people over many months. He was raising many months before I met him. And then I came in. I then spent too long negotiating but then we finally worked out a deal end of Sep and then my lawyers and their lawyers negotiated the agreement Sep 26th and then we did our dinner. But then YC smartly moved in after this closing dinner and booted me out. Funny enough Justin Kan and I ended up in Vegas a few years later at a tech party at Caesars hotel and had a good laugh about it. He remembered me as the crazy Marine who was writing a huge check into Airbnb before they elbowed me out. This isn't unusual - they probably googled me at the time (back then all of the results would have been stories about iraq, Syria, afghanistan, Pakistan operations; black operations and crazy shit). They probably thought they were protecting Airbnb and keeping dumb money out of the cap table. It's quite common for good investors to strongly advise you not to take dumb money and I agree with the practice. And that goes back to one of the lessons from my post. I realized that for founders and investors to take me seriously and not lose deals I had to prove myself, build a positive brand by helping founders and getting smarter about this new world I was operating in.

jackgavigan 11y ago
> ..YC smartly moved in after this closing dinner and booted me out. Do you think YC told AirBnB "We won't accept you on our programme if you take investment from Paige", or do you reckon it was AirBnB's decision to join the YC programme instead of taking your investment?
- paigecraig0231 11y ago
  Pure speculation here: But objectively I think my money was perceived as "dumb money" and YC had a great rep even back then. When you compare the offers the YC money is clearly the best deal and smarter move.
napoleond 11y ago
Thanks for joining the conversation! To clarify, I didn't mean to insinuate that I thought anyone was necessarily lying; it's more of a "surprised" weird. Surprised because: (a) Based on your story, Airbnb got accepted into YC early (or at least received a strong enough signal that they would be accepted). I don't think that's inconsistent with Airbnb or YC's account, I'd just never heard about it before (amidst a ton of lore about Airbnb's early days at YC). (b) Airbnb had the foresight to see that YC's deal was better than yours. This would actually have been non-obvious in 2008: Dropbox was only a year old, Stripe didn't exist yet, and YC's best-known successes at the time would have been Heroku and Reddit. Not to mention the fact that you were offering them 10x the cash at 10x the valuation. So it is "weird" in the way that history is kind of weird. I don't doubt your version of events though, and I appreciate you sharing it.

jackgavigan 11y ago

> ..YC smartly moved in after this closing dinner and booted me out. Do you think YC told AirBnB "We won't accept you on our programme if you take investment from Paige", or do you reckon it was AirBnB's decision to join the YC programme instead of taking your investment?

paigecraig0231 11y ago
Pure speculation here: But objectively I think my money was perceived as "dumb money" and YC had a great rep even back then. When you compare the offers the YC money is clearly the best deal and smarter move.

napoleond 11y ago

Thanks for joining the conversation! To clarify, I didn't mean to insinuate that I thought anyone was necessarily lying; it's more of a "surprised" weird. Surprised because: (a) Based on your story, Airbnb got accepted into YC early (or at least received a strong enough signal that they would be accepted). I don't think that's inconsistent with Airbnb or YC's account, I'd just never heard about it before (amidst a ton of lore about Airbnb's early days at YC). (b) Airbnb had the foresight to see that YC's deal was better than yours. This would actually have been non-obvious in 2008: Dropbox was only a year old, Stripe didn't exist yet, and YC's best-known successes at the time would have been Heroku and Reddit. Not to mention the fact that you were offering them 10x the cash at 10x the valuation. So it is "weird" in the way that history is kind of weird. I don't doubt your version of events though, and I appreciate you sharing it.