YouSaid · the spoken record

Zach Perret

lines on the record: 64
first: 2024-10-16
most recent: 2024-10-16
sittings or episodes: 1
sources: podcast

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“If anyone can get credit, great access to credit based on the data that they have with them in their head, your transaction history, so on and so forth, you have the ability to link that based on the data you have in your head, that would be a huge unlock. I think if financial fraud, which right now, at least in the US, is like growing at an increasing rate, if we can have it either flat or at least growing at a decreasing rate minimally, ideally like declining, that would be huge. And I think we can very realistically do that. And I think if it's a one-tap experience to apply for a loan, that's the threshold that we have. 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 spend it. That's the goal.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Last time I had this, like, oh my gosh, the internet, this is the way that technology is going to go. There have been a few of them recently, like trying the meta-ray bands. It's like, oh my gosh, this is a thing that's going to happen, like I'm dealing with some of the AI stuff has been fascinating. One of the first ones I had was like shop pay, where I showed up to this website and it had all my information. I just clicked buy. And it was like, ah, that's how the internet's supposed to work. And I think that that innovation is underrated. Everyone's like cloned it now and PayPal's done it and Stripes done. Everyone's built the same thing. But the first time I saw that, they had this incredible advantage relative to the rest of the market. So it was very cool.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“So many things. We were talking about experience. I've been proven time and time again that hiring for experience in certain pockets where like deep industry expertise matters is really, really important. And so that's been just really in my face a couple of times.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“The okay, our stuff, like putting OKRs in a business way too early is totally wrong. Putting revenue metrics on a company before they've achieved product market fit totally wrong. Like encouraging founders to like, I mean, this was addressed in the founder mode post that we talked about, but encouraging people to like hire great execs and then let them have space. Totally wrong. Don't like micromanage them too much, but stay close. You need to stay in the details. You need to understand what's going on”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“There have been a few. One of them was transformational where VC came in and said we had a round that was falling apart for very unrelated reasons. They came in and said, look, we're going to stand behind this. We're actually going to give you more money at a higher valuation. And it's going to meaningfully change the trajectory of the company because there was some risk on the ground that kind of came up mid-round. And they were like, no, we believe so deeply in the company. So that decision to invest at the right time made a huge difference.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Paying it forward. And so what oftentimes happens is we have these WhatsApp threads with the founders and the laws of questions, and we hear a question enough. I'll go down and write a blog post. And the blog post that I write will oftentimes be something I'll just distribute within Plat. Like, hey, how do we think? I have a blog post on atomic teams. Like, how do we think about atomic teams? Why do they matter? Like, why are they useful? How do we think about applying them into product innovation? So I'll share that with Implaid. I'll share that with all the founders. And sometimes we'll even do a Q&A, which we'll record, and then we'll have this artifact. And so for me, it makes me a better entrepreneur to go deep on these like key topics that I recognize. It prompts me to actually teach things to the company in an important way. And then it creates this amazing kind of paid-forward mentality with the founders that we interact. So I think the average returns have to come down because the amount of capital is going up and the amount of amazing companies is not necessarily going up at the same pace.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Time. You don't have a system for it. You haven't built infrastructure. You have no leverage. And so for me, a good friend and I sat down and she said, hey, I'm going to go be a full-time VC, but I really want to start a fund. I said, this angel investing stuff is interesting because I learn a lot, but it doesn't have that much meaning and it takes too much of my time. And so we decided to partner together. And she kind of decided to go raise a fund. We partnered. We did it together. And that became the first mischief fund. Since then, there are two other amazing entrepreneurs. And we've created this fund structure that I have max leverage. They run it full-time, three full-time people. And me who does it a few hours a week, but I get to spend time talking to entrepreneurs, helping them through sticky situations. And the amazing thing for me is like, I said, I talked about sending emails and people responding. And I say Silicon Valley in like air quotes here because it's not about being in the place. That enabled me to be an entrepreneur. That taught me everything that I know. And I think there's a value.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“That's a good framing, and I appreciate the spice. Going back to one of the themes that we've had throughout this conversation, you have to examine the specific rationale and reason. For me, as Plaid got bigger, I got sucked later and later stage. I was spending time with the gigantic banks. I was spending time with the gigantic companies. And I found that Plaid was in some sense losing some of the founder mentality. It was like losing some of the fine-grained attention that I needed to pay to the early stage market. In 2016, I started angel investing just because I wanted a reason to go talk to these companies. And I did a bunch of it. Had reasons to go talk to founders, had reasons to engage with them deeply. It kept me fresh. It built a great network. I learned things that I brought into how we developed products at Plaid. I met amazing people who ended up hiring. And it's created this really virtuous cycle. Angel Investing actually, I think, is very distracting to founders. The reason for it is it's personally on you. People want to talk to you all.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“When I see I think self competition is the answer to that, at least for me. At some point, now I care very little about what our competitors do if we're not as good as we could be, that starts to become a real challenge for me.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Is it internally driven or is it externally driven? Do you have a threshold? That was a good one, that was not a good one. Or if you found a better interviewer than you, if everybody in the world was a better interviewer than you, even though you were still objectively really good, would that be okay? Yeah, exactly.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“That's a very hard question. I think we all land in the bigger, faster, more, like the relentless pursuit of doing more and so forth. I fall into that trap absolutely as well.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Good question. Everybody says that having a kid teaches you time management, teaches you prioritization, teaches you coaching. I believe that all that stuff is really true. For me, the biggest change was personal. It just increases your capacity to love and recognize other people. My favorite thing about having a daughter is, yes, getting to love her and love the snuggles and all of the things that she does. But it was actually seeing my wife become a mother and seeing the change that brought about in her and seeing her capacity change. And that recognition of someone, you know, who you've known for so long you think you know super well and then you just see this totally new aspect. It made me think differently about what are the underlying aspects that other people in my life might have and how might they change over time and being more open in accepting of that.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“I was talking to an entrepreneur friend of mine who I deeply respect, and they said we set a big, hairy, audacious goal. And then within that, we asked the team, what's the first thing you can celebrate? Because it means that you're on track to achieve the Big Harry Dishes goal. The Big Hairy Dishes goal I've always done what's the first thing you can celebrate question I've never done and I love it. It's a huge unlock. So now you can ask the team, what's the first milestone that you can achieve and prove that you're going in that direction and then actually doing a celebration around it?”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Internal praise of hey, like you made progress there. Let me cheer you on and be the cheerleader to help you go from four out of ten to a six out of 10 to an eight out of 10. That's really hard. I do feel strongly that you should never celebrate something that just factually isn't good. If we're delivering something at a four out of ten, that is factually bad. And we should not be celebrating that we're delivering a four out of 10, but we should celebrate the progress that we're making and the trajectory that we're on. And so finding a way to like support the team through that terrible to good to great process.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“One of my biggest flaws as a leader is I'm not great at recognition of progress if the outcome is not excellence. Let's say we have some problem with the company. And currently we're operating at a two out of 10. Going from a 2 out of 10 to a 4 out of 10, you have just made something twice as good. My CEO tells me this all the time. He's like, you got to celebrate that. That is good progress. And yes, you can say there's another horizon that we got to go to, but you got to celebrate going from a 2 to a 4 out of 10. Sometimes that matters quite a lot. Personally, I am never, never okay, celebrating that because my answer is like, that's a four out of 10. It's like we're still horrible. And objectively, that is the correct answer if we stay a four out of 10. But oftentimes, the trajectory is you go from 2 out of 10 to a 4 out of 10 to a six out of 10 to an 8 out of 10, and then eventually you get to a 10 out of 10. Like finding a way to celebrate those interim milestones that are not yet perfect, it's been really hard. And it definitely discourages people within the company.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I do worry about that. That's why I wish people would ask me the question how confident are you, and how much do you care?”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“All the time. Yeah. Gets me in trouble with my wife because she's like, Why are you so confident in this thing that you've never thought about? I'm like, I'm not confident. And I think you were planning to ask this question later, which is like, what's the question that no one ever asks you that they really should? For me, the question that no one ever asked me is, how confident are you? And how much do you care? So if you ask me, hey, is the answer red or blue? Red. How confident are you? 0% confident. How much do you care? Not at all. Those three need to go strongly together. Okay.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Philosophically, I have a very hypothesis driven decision making model, which is you asked me a question I have an answer. It's not a deeply held answer always, but always start with a starting point. Within the company, we push this really hard. So if there's a decision to be made, there's always a straw man of what decision is. I'm not sure I have a specific unmade decision. Does that okay?”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I definitely believe it will grow into great company if we're not there already. And I would love to have that increased rigor, that being a public company brings. I think that's actually probably a really useful thing for companies. Certainly all the public CEOs that I've talked to, or many of the public CEOs, I shouldn't say all because that's not true. But many of the public CEOs that I've talked to said, like, you know, the rigor is a really good thing. It's helpful, so on and so forth. But on the flip side, it is a milestone and is a very useful tool for us to do at some point in the future. that day is not today and that day will hopefully be in the next couple years.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“The viability and the excitingness and the value of an IPO changes a lot for a lot of founders. Look in the long term, we said this before, in the long arc, we would like to be a public company. We're not in any specific rush to do so. And generally, I think of an IPO as a meaningful, important milestone in a fundraising event when you need the capital, when you need the milestone, when being public is really useful to the company, then you should go do it.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“So far as I can tell, I think the large MA transactions are mostly getting deeply investigated and off NEPs blocked by the regulators. That political environment will change eventually. We did see some of these odd aquaire large AI acquisitions, which have been fascinating. But I don't think that works with a company that has tons of contracts that you actually want to transfer over to the acquired company. Can't predict the future, but I do think that it's pretty hard to do large M&A right now.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Because I can't come into an Instagram and Facebook. The structure that we set up with Visa was that we were running as an independent entity. We had access to all the tools internally. I was the CEO of the independent company. We could run as fast as we wanted to in the direction we wanted to. And we got a boatload of funding to go do it. That's not the worst setup. Now, I like the independent path better. No answer is not.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so there's a fiduciary thing that pushes you towards the raise at max valuation and then the investors that invest be darned. My view is different. I feel a deep responsibility to the investors that invest and implied. Like I want every one of them to make a lot of money on Plaid. And that means that my expectations for the company are really, really high because I know I have to get back to a high hurdle rate that we've had in the past. Now, I believe that we'll do it. I believe it'll take some time, but I believe that we'll do it. The underlying fundamentals of the business look way better now than they did whenever I invested. The reality is that the multiples have changed. You know, we're on a long journey. We got work to do. We got to make sure that everyone makes a bunch of money on their investment where they invested. And if we're lucky enough that the investors continue to hold through that entire period, I really believe they'll be able to do it, but that takes patience.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Good question. The true value of a private company is impossible to tell, right? The true value of a private company is what someone is willing to pay to buy an incremental share of that company. And that's why you see valuations being like all over the place with private companies. You know, in a lot of senses, I wish we had a real time mark to market because that would make it much simpler to do things like compensating employees and doing acquisitions and so on and so forth. The reality is we raise money in the situation and in the environment that we were in at the time. Puzz valuation's gone down since then. Frankly, the valuation of every tech company has gone down since then. And by the way,”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Some of them did, yeah, but not selfishly, just people planning to buy a house, for example. Then we do this, do the next round, which was a big step evaluation, and we let people sell as kind of, we wanted to create a rational amount of sale. We let them sell as much as we could rationally. But like it wasn't this full amount, instead of buying a house, maybe something larger than a car but less than a house, a chunk of what they could sell was in the whole thing. That, I think, was like a hard thing for them, good outcome, like, because they could see the light of the future and the growth of the plaid and so on and so forth. But definitely a hard whiplashy thing. But I think that was really great that we let our employees participate there. And as we're able to do more segmentaries in the future, really focusing on the team, that would be the goal.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly, exactly. And look, who am I to say that they shouldn't get mentally locked in on a thing? Like we said we're going to sell the company for this amount of money. Visa's a very legitimate buyer. Like there was real cash coming in. And I told them there was risk. But, you know, you spend the money in your head. Then we had to get to the end of the transaction and we walk away. And I was like, this is going to be better for the company in the long term. But all of a sudden, they couldn't spend the money. There's a very different aspect of liquidity that was real for them. And then we said, look, we're going to go raise money. And we hope that we're going to let you participate in a secondary. And like that was like a pretty hard thing to say, but I also couldn't, I didn't want to guarantee anything because we got the secondary, then we did as much”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“When we did the sale to Visa that ultimately didn't go through, we raised a funding rent 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't get to 100% of employees, but we got to like the large majority of employees that were employees that were able to participate in that secondary. And that was hugely meaningful to me, hugely meaningful to the team on the other side. Keep in mind, we'd said, hey, we're selling the company for $5 billion. Well, let me finish the whole story. First, it was like we're selling company for $5 billion. Then we got the end of a year. And everyone's like, oh, okay. They don't spend the money practically, but they spend the money in their hat.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, but I mean, you know, we hadn't paid ourselves in six months at that point. We were like, whatever. So at some point, we're going to actually run out of money. My co-founder was living on a friend's couch. I'd moved in with my girlfriend because I couldn't pay rent anywhere. And I had like a moderate amount of credit card debt, which I don't advise to any other founders. But, you know, we thought we were going to die. But we also had nothing to lose. So you just keep going.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“And then the rest of the funny ran fell apart. And we were out of money. We were basically dead as a company. And so we went to all the investors that have been planning to invest. And we were like, hey, look, the lead has backed out. We'd still love to take your money, but the lead is gone and we just want to be transparent about it. We don't want to be a surprise. So we did it and everybody walked away from that, except for these three people all named Justin. And they invested a collective 60K in the company. That kept us alive. They invested like 60K to maybe $2.5 million valuation. That was a lifeline we needed to sustain until we could get to some customers that were actually using it. We had a late stage contract with Venmo. Then it was maybe like six or eight months later that we went back and raised a seed round. It was valued at $11 or $12 million. So like an actual good step up.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Our seed round was horrible. Oh my gosh, we have this crazy story. I don't think I've told this publicly. We started out first building a consumer app. So this was kind of post-2008 financial crisis. There's this movement called Occupy Wall Street. And it was like people moved tents in and lived in Wall Street. And the big takeaway from everyone was consumers are really frustrated with financial services. They don't think that the banks are building the products they want. So being like kind of 23-year-old entrepreneurs, we set out and said, we're going to go build a better budgeting tool for consumers because that's going to help consumers live a better financial life. So we had this whole story for a year. We like built a bunch of these. They all failed. And then we pivoted to build this infrastructure piece, which was basically the back end to our previous product. And that was actually a really good idea. But when we were trying to raise frame people, everybody said no to us. We actually lined up this early funding round. It's a 500K funding round at a $2 million valuation. And the lead investor for this funding round backed out. And he was investing like $100,000 or something like that.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“We kind of did what felt natural for the company and what felt right for us. My dig is like money is a resource when you need the resource you should go get the resource and you should do it. Yes, of course, in the most efficient way that you possibly can. But for a certain amount of time, we just didn't need the resource. We weren't spending a ton or our business was profitable in the early days. Not intentionally just happened to be. And so we were like, oh, we don't need the money resource. Like, money is not the tool that we need to use in order to solve the next challenge. Then later it became the tool, so we want to raise more money.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“My take is great entrepreneurs are going to apply their unique lens to what they do. We have this weird philosophy, I think that raising money is a big waste of time. So we try to raise money as infrequently as we possibly can within PLAD. So like, you know, we go like two and a half, three years between funding rounds. And in the early days, some people would call us and be like, oh, is the company dead? Because you haven't raised in the last 12 months? And we're like, no, revenue's growing. Everything looks great. We just didn't want to raise money.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, velocity's correct. Speed in a given direction. The direction also should be right. Like, it should be the correct direction.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so one of our company values is move fast, but you have to be careful when to apply move fast. Like once you've found product market fit, move fast. That's absolutely the right thing to do. Before you have product market fit, sure, maybe you should move quickly through ideas, but also like spending the time to think about what the right thing is, like gathering the signals, gathering the data, understanding what you need to do, like be right and then move fast.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“About our customers and way more about how to build a great product for our customers than it could have in any other way. And so don't hire the VP of sales early if you don't want to. Like if you don't think that's right for you, OKR is another one. Vocrs were built for manufacturing. We don't manufacture software. We're not running assembly line to create software. Goals are important, but do it your own way. Don't just read the Indy Grove book and try to apply this thing that worked for Intel to your business if it doesn't actually fit to your business.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“I do think that a lot of the advice given quote unquote is really applicable narrowly and not broadly. Every founder needs to, for the big important things, make a decision on their own of what really works and then like be willing to go back and remake those decisions time and time again. I will say I think that for 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. But there are some of these things like I'll take, for example, sales. One of the most common early stage things that people tell small companies is you need to go hire a VP of sales. If you're an enterprise company, if you're able to do founder-driven sales, like I think that's actually totally wrong. For me, I didn't want to hire a VP of sales for a long time. I hired this group of these amazing young people that would just help me do sales. Like I was driving sales and like they were around me like making it more efficient. They were go shredding my emails, all the stuff. I was ever seeing it. And like that scale is for quite a long time, like way longer than it should have. But in doing that, I learned way more.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Totally. I think people are going to see that there's Steve Jobs top 100 off site that he did. People are going to see that and say, I should do a top 100 offsite or top 50 offsite, top 20 offsite. That's actually horrible in a lot of companies. He did it for a specific reason. And I don't know what the specific reason was, but they had a specific reason in mind and like the way that he applied it and used it was incredible for Steve Jobs at Apple at the size that they were at the time that it was that thing. It doesn't mean that that practice is universally applicable. I also think that, you know, like building a philosophy off of Brian Chesky, who's like, you know, one of the most amazing leaders, like, yeah, everyone can learn a lot from Brian, but not all of us are Brian.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“That's the mode that it seems like a lot of people at companies that we're talking about a lot were in, and I've certainly seen that. We've certainly made mistakes with overdelegation. But I do worry that it's going to be a little misinterpreted.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it's going to be one of the blog posts that is the most misused and actually causes a lot of the worst behavior in startups for a long time. And I think for the people that truly get to get to the level of having all the context that he does, then it'll actually be a huge unlock for a lot of people. The reason I think it's going to be misused is a fewfold. First is one way to read it is to deeply undervalue great execs. And I think that that's totally wrong. The second way to read it is the founder should micromanage everything. And while I am a fan of micromanagement or actually said differently, I'm a fan of sweating the details, which is one of our core values in certain areas. If you try to micromanage everything, it's never going to work. And I think didn't hit the nail on the head of the whole point is like delegate effectively. If you delegate something and it really matters, you got to stay close to it. If you delegate something, it doesn't matter. You can stay a little further away from it. Don't over-delegate because I think that.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Just the speed of it. Like every founder chat I'm in, we're talking about it. Like, you know, within the company, multiple people brought it to me. I brought up to our exec team. It was just like this really fast set of conversations”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“I was surprised how Firelit went, and it clearly struck an error for a lot of people. So, I think there's a lot aspects of it that are really good.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Sometimes you get really annoyed with a search that's been going on for a long time, and you're like, I just need to hire someone. And sometimes that's actually true. And often that will lead you to make mistakes. Let's imagine I'm an early stage company. I can't find the right accountant, but I just need an accountant. At some point, you're actually right. Yeah, you actually do just need an accountant. Chances are that higher that you're going to make is not the right one and you have to dig yourself out of that later. So usually it's been the like, I really actually just need this job to get done for a little while. And I know I'm going to have to go back and fix it later, but that's okay.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Years like kind of wasn't a fit for PLAD. We just had this bad assumption that people that have been doing a thing for that long weren't going to hustle. This was based on our own experience, meaning we'd interviewed a bunch of people and kind of either seen friends or ourselves made some hires of people that had been really experienced but like weren't willing to work that hard or really jaded in their thinking. So we kind of avoided that early on in the company. But also there was a time when experience didn't matter as much. Like hustle mattered a lot more. Now that we're getting later into the company and as we're going to these more specialized fields, finding someone that's been a machine learning fraud engineer for 20 years, they're going to make a huge difference on your fraud product. You just have to filter for mindset, right? You have to filter for a hustle. You have to filter for the values that we actually really think are important within the company. And so we've shifted our thoughts on experience quite a lot. We do still want this balance, though. Like we want this, like we're in financial services. We want a 70-30 split. 70% of people on our team should not have come from financial services. 30% should have.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“So we have a couple of these core philosophies, and one or two of them have evolved. One of them is higher for spikes. This one hasn't really changed. We look for people that are incredible at some things, even if they have glaring weaknesses in other areas. So long as we have a team that can balance that out, we would rather have the spiky person. Because it turns out a well-rounded person that maybe doesn't have any really tall spikes. If you build a team of those, you'll have one certain, you can imagine like a level, if you were to chart this out, you can imagine there only reach a certain max on the vertical axis. But if you have spikes and you make the spikes all kind of work together, then the level that they'll reach on the vertical axis is far higher. So higher for spikes is a big one for us. It also means that we like people that are weird, that have unique experiences, that are different, that have different background or different ways of thinking about the world. So that's been a big one for us. One that I've changed was there's this thing internally called the experience trap where we basically thought that anyone that had been doing a certain thing for like more than 15 or 20 years.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“This is related to recruiting, but sort of not earlier on in the company. I had a five sentence rule, which is if you write an email with more than five sentences, no one's ever going to read it. So write them with less than five sentences.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Be yourself and do it. One of the things that someone told me really early in my career is that the best thing that you can do is go learn from other people that are willing to talk to you. So I got really good early on at just sending cold emails to people saying like, hey, I love this thing that you do. I'm super, super impressed by it. Will you talk to me on the phone for 15 minutes and tell me about it? And people were shockingly willing to do that early in my career. And it applies the same way for recruiting. So by the way, exactly what I just said, you can do just to get people that you kind of want to recruit but aren't recruitable. But in general, just saying like, hey, I'm Zach.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Always. I love recruiting. I started out hating recruiting. And it was one of those things where I realized that if I didn't become good at it and if I didn't learn to love it, I would build a terrible company because you read any business book. We'd go to great, right? First is, do you have the right people on the bus? Second is, what the heck are you building? But first is they get the people right. And I realized if I didn't start to enjoy recruiting, then that would be a challenge for me. So I went deep in, like I figured out kind of like, convinced myself, tricked myself in all these different ways to love, love, love recruiting. The key for me was I'm super competitive. I like games and recruiting is a win-loss game. Can I get this person to want to work in my company? Can I find the best person? And then pretty quickly, I will know, yes, they accepted an offer. They didn't accept the offer. So for me now, it's like this intense form of competition with myself on can I find the person? Like, I love the hunt and then can I convince them to join me? What about?”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe, but I guess my take is in general, you know, if you have two atomic teams, you throw them at the same problem if they have like roughly the same skills, they're going to start from roughly the same place, and one might move faster because they have this knowledge or background or whatever it is. That has been like one of the things that I've evolved my thinking on quite a lot over the years is the importance of experience. I think a lot of people worry too much about defensibility in the immediate term and at the start of a new project. And they were far too little about defensibility in the late stages. So as long as the grinder problem, the difficult, hard hustle problem that you're going after has the ability to be meaningfully differentiated in the long term via network effects or brand or scale or whatever it is, then it's great. If it never has that ability to be differentiated, I mean, be careful with your time.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Willing to grind it out, you're going to have a unique product that no one else is willing to build or able to build sometimes. You know, those things that are not necessarily like it's not about the intellectual brilliance of the strategy that you come up with, it's about your ability and desire to do the work. I love those kind of challenges.”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so the early history of PLAD was we needed to integrate with all the banks. And these integrations were not flip a switch magically integrations on. It's like a lot of work to actually set up integration with the bank. In the early days, we had to actually build screenscrapers for the banks because the banks didn't have APIs. And like every screenshot was different. And we had this realization if we're able just to grind out all the integrations, we're going to be better than anyone else. We will build better technology, yes, for these integrations, but also no one else is going to do this thing that we're doing. No one else is as crazy as we are to be willing to go grind out 12,000 bank integrations and then make them all scale and build all the software that you need to self-heal the integrations. It was just a mess. And anytime we find a problem like that, I'm like, yeah, that's it. Like I get excited about it. And everyone inside the company, like, even though we talk about this concept, people inside the company are often like, it's going to be so hard. It's going to be like, you know, it's going to be difficult. There's like a long path. It might not work. So on and so forth. I just believe that sometimes if you're”
2024-10-16 · The Twenty Minute VC · 20VC: Why Founder Mode is Dangerous & Could Encourage Bad Behaviour | Why Fundraising is a Waste of Time & OKRs are BS | Why Angel Investing is Bad for Founders to Do and the VC Model is on it's Last Legs with Zach Perret @ Plaid · IDENTIFIED FROM THE TRANSCRIPT · source