Plaid

“If I need to go hire for a role that I haven't hired for, I'll create a list of the top five people that anyone will recommend that are currently doing the job. Just cold email all five of those people and then try to get a coffee with as many as I can just to…”

“Everything's always broken. It's just a question of how broken and how important as to if we're going to focus on it. And when you're moving really quickly as a startup, you have to be willing to let certain things go, understand that there might be a fire smo…”

“It was partially opportunistic. We had the chance to meet a few really amazing investors. It was partially because we knew we needed to scale a bit faster on sales and marketing, and it was partially because it had been two and a half years since we'd raised, …”

“We look for the areas where someone is truly world class, and we prefer to hire people that have a few elements in which they're totally amazing, where they can really lean into their strengths, than hiring for the absence of weaknesses.”

“And so almost the history of the company, I've probably spent about a third of my time recruiting people.”

“We're fortunate to be in a business where our revenue doesn't scale directly with the number of people that we have, meaning we don't have to go out and hire thousands or tens of thousands of people in order to scale a great deal as a company.”

“The company Plaid, I would count as one of my absolute biggest misses, and the mistake that I made was I looked at the product that they were thinking about building in the very beginning, which was consumer financial management and playing with location at th…”

“On the VC side, Matt has worked with the likes of Peter Fenton at Benchmark, Several Sequoia partners, Hemond at GC, and Mamoon at Kleiner, to name a few. As for founders, Matt's worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport, and many mor…”

“Yeah, this is an easy one. It's Plaid, which I was part of the team that led the seed and Series A at NEA many, many years ago, so I know Zach has been on your show, and I think the world of him, so one of my top priority after founding NewView is figuring out…”

“Launched in 2018 with their 1.35 billion dollar debut fund, They've already set themselves as leaders in the world of growth funding, with three massive exits in less than two years, in the form of, check this out, Plaid sold to Visa for 5.3 billion dollars, A…”

“One of the leading seed-focused firms of the last decade, with a portfolio including the likes of Airtable, Glossier, Pillpack, Plaid, and many more incredible companies.”

“Five years ago, the people were saying, this is a flash in the pan, this is not going to work, we are better at technology, we have these customer relationships, look, we've got all these branches. This whole fintech thing is tulips in Amsterdam. I think there…”

“I led the seed round in Plaid and joined the founders, William and Zach, as their first outside board member.”

“And, you know, I was able to write the first check in the, you know, companies like Robinhood or Platt or Gusto or Flexport.”

“Is I don't think it was fair. I don't think it was correct, but it doesn't, my opinion doesn't matter is, you know, the government is a decision maker at the end of the day.”

“99.9% of my wealth is in platinum column.”

“You know, you raise a triple evaluation nine months later.”

“Pretty much anybody building in financial services in the U.S. Is some way associated with Plaid.”

“One of the things you realize about founders is first time founders, they don't realize they have to be great at firing. They just think they have to be great at hiring, but you have to be great at realizing when your talent's not working out and identifying t…”

“Like, I don't think I would be a good manager for a 20 person team anymore. I was when I joined Plaid, but I'm like so out of, that was six and a half years ago, like I've lost all those muscles.”

“You're Plaid, you're doing, or Stripe, or whatever you're doing, banking and payments thing, like you're not, you can't move fast and break things. You have to move fast, as fast as you can while not breaking things.”

“I think at most companies, the advice that I give is somewhere between 15 and 30 people, things will break on the management side, and the problems that you encounter are not cutie cutter.”

“Like definitely I have no difference in like PR success rate. I think the only thing in remote that's hurting me is Paul's score in terms of belonging and how much fun people are having on the work. Like, I think that has gone down from before, but I think in …”

“And if one of your function leads isn't scaling, yeah, you might give them three months, But pretty quickly you got to realize, hey, it's not working because next thing you know, you might have, you know, if you wait like a 12 months and then you make a new hi…”

“I mean, before, meaning it shouldn't come out of left field. The person should know that their performance is not quite meeting the bar that you have anymore, like a couple of months before.”

“My overarching thesis is that a lot of people things On a lot of people matters, how you level, how you title, how you comp how you organize your org, like your manager to IC ratio, remote hybrid. It's like, pick a thing, pick one of the three options on the m…”

“Well, so I know a few truly great people who I think are, have the right viewpoint and are really good at motivating and delegating, meaning they create the structure for success, like the North star, the product roadmap, and then they're able to motivate othe…”

“So even at Plaid amongst ICs, for example, there are no titles, even in managers outside of the person who leads like a giant area, we have don't, we don't have directors and things like that.”

“Where all the interviewers are like, you know, heads of things, and they're all asking the generic question, like, oh, tell me a great success in your career. Tell me about a time you failed. And you don't get real signal from that.”

“At any scale, like at plaid scale, like 50, I mean, we're much more than that, but like when you get to 50, a hundred million in ARR, you're living in a world of competition.”

“So I think at scale, when you're, like, at our size right now, like, we're, you know, a thousand people total, Like transparently, I think you want to go with the grain of the industry, not against it, because it's just too much fighting to go against it in so…”

“I joined when the company had, you know, forty-ish people and, you know, less than ten million in ARR.”

“You have to have interviewed enough people that you know what greed looks like. And so if you have the perfect candidate be your first hire, like the first person you interview, it's really hard to pull the trigger because people don't have any comparison poin…”

“I think for the existing startups, what you''ve got to look at is it probably isn''t going to be UX and there''s probably going to be consolidation because we''ve over verticalized things by going after every like bit of the software with a slightly better UX …”

“And I, you know, I probably got, I got too intellectual about it.”

“Dylan at Figma, Zach at Plaid and Alex at Scale, and I have enormous respect for all three of them got to know all three of them really early, and I just, I struggled with it.”

“Now they have no incentive to do that because if they let you do that, it's easier to move money out, and they don't want you to move money out because they make money on you storing money there. That's how a bank works. You get lock in to other products, but …”

“We actually lined up this early funding round it's a 500 K funding round at, ah, like a two million dollar valuation. The lead investor for this funding round, like, backed out. And he was investing, like, a 100,000 dollars or something like that. And then the…”

“I think that raising money is like a big waste of time, so we try to raise money as infrequently as we possibly can with implied.”

“Like, we're in financial services. We want a seventy-thirty split. 70% of people on our team should not have come from financial services. 30% should have.”

“I don't think that most people, like, immediately orient on value, the dollar value of the acquisition. Like, sure, yeah, it reaches a threshold and the dollar value, like, starts to make sense. But I think when people really go through that Agony around selli…”

“Doing that, going from one to two would have been the right answer, and then maybe we could have done the next two at once, but going from one to four it was super hard.”

“Philosophically, like, I have a very hypothesis-driven decision-making model, which is you ask me a question, I have an answer. I, like, I'm, it's not a deeply held answer always but I always start with a starting point. Within the company we push this really …”

“For, you know, 80% of the things in a company, you can literally just copy what's been done before, and 20% of the things you need to be unique and spend all your effort in being really, really unique.”

“Now, I believe that we'll do it. I believe it'll take some time, but I believe that we'll do it.”

“That's the target that we have is like, I want to apply for a loan. Click apply. Do a face ID. Great. Your application's submitted. Like that's the goal.”

“When we did the sale to Visa that ultimately didn't go through, we raised a funding round afterwards. One of the most complex things to do in that funding round was I wanted to try to max the number of people that could participate in the secondary. We couldn'…”

“We look for people that are incredible at some things, even if they have, like, glaring weaknesses in other areas. So as long as we have a team that can balance that out, we would rather have the spikey person, because it turns out, you know, a well-rounded pe…”

“And ended up making what I think was a 51 49 call to say, like, it's the right answer to sell the business. For a variety of reasons at the time. A year later, we had that same meeting, same group of people sitting in my living room, having the same, same styl…”

“Our business was profitable in the early days. Like, not intentionally, it just happened to be.”

“Plaid is a great example. It is a company built on a grind problem. Intense amounts of integrations, data challenges. It's not technically hard, but the man hours to do that was insane.”

“He was saying, why were they lifted from the manufacturing industry and plopped down into the software world? And I would very much agree with that.”

“It probably was one of the first rounds of Plaid, which I subsequently corrected myself for by doing the Series C of Plaid. So I think we invested at 2.4 billion for the Series C, and I was debating a five million dollar difference with Zach for the Series B. …”

“We hosted a dinner for the CEO of Visa, and I sat Zach at Plaid right next to Alec Kelly at Visa.”

“I don't find it crazy, honestly. Like I think when I was at Plaid and we were competing with talent for like Stripe, that felt like no harder than what I'm doing now.”