The Wisdom Wall

“I think the truth is that even with your board as a founder, I'm not sure your incentives are completely aligned because it's back to, well, first of all, what is the price on the table, right? Is it a nice two or three X for the VCs on the board or not? Because if it's not, they're going to tell you not to sell, even…”

“we believe that we monetize 20 times better Then other spend management systems, systems like Expensify or Concur, because we monetize through financial services.”

“And so in all those cases, these companies are spending one to three percent of their market cap on the MNAs, which is not like, that's not transformative MNA. It's really like, again, these big consolidators are just taking call options bets on these fast growing new companies.”

“I think that in a world of AI and as AI starts to mature, I think a lot of the benefits actually go to what I would call not the incumbents, but like the fast moving larger companies. Like, of course there will be a few companies that start from zero and explode, but you know, companies like Salesforce, like…”

“Paul Graham has an essay called never talk to corp dev that he published, I think like 15 years ago, um, which I, my hot take is I actually don't agree with it. And essentially his, his point is that look, as soon as you talk to a large big tech, or you talk to a potential acquire, you've kind of crossed the Rubicon,…”

“in M and A, it's the opposite. I think you don't want to be nice. You want to be not rude, but you want to be direct and you want to be harsh.”

“most successful MNA, I would bet, you know, I have to run the numbers on this, but most successful MNA comes in tech where the companies have been partners first, because like, why wouldn't you take a call option on a relationship?”

“In terms of when you actually started the M&A process, I think that's when as a seller, you're actually at the most weak negotiating points to be very careful. So that's when you got something in writing and you're bought in, but nothing's closed. That's when the buyer will try to do what they can to extract more value…”

“So once you're selling to PE, I would say absolutely use a banker, 10 out of 10 times, because that's like a tried and true method of like a data room and a management presentation and like a whole dog and pony show.”

“The number one advice I give founders on when they're testing the waters on M and A is to not tell anyone at their company. Because as soon as you get folks excited, it's a little bit like raising around, but at an extreme, as soon as people at the company, even if it's just your CFO knows and he sees dollar signs or…”

“you need to partner with folks that are similar to you in order for it to be successful. It can't be one really large company and one really small one or one that serves companies in one space and one in the other, because then again, it's like, what's in it for me? Everyone's in business. It has to be an exchange of…”

“BD and product partnerships should be the VC arm of a company. And this is what I tell my team is like, look, we need to look for pole vault opportunities, but we're going to fail sometimes like, yeah, Navon zip are going great, but there's a bunch of other partnerships that. Haven't necessarily worked out as, as well…”