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Podcast Summary: The Twenty Minute VC (20VC) - Episode with Zach Perret
Episode Overview Title: 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 its Last Legs with Zach Perret @ Plaid Host: Harry Stebbings Guest: Zach Perret, CEO and Co-Founder of Plaid Duration: Approximately 20 minutes Air Date: [Insert Date]
Guest Background
- Zach Perret is the CEO and Co-Founder of Plaid, a financial technology platform that connects applications to users' bank accounts.
- Raised over $734 million from prominent venture capital firms such as NEA, Spark, GV, Coatue, and Andreessen Horowitz (a16z).
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Key Discussion Points
- Founder Mode
- Danger of "Founder Mode": Zach describes a recent blog post advocating for "Founder Mode" as potentially harmful for startup founders, as it may lead to poor behaviors.
- Grinder Problems: Introduced the concept of "grinder problems," which are difficult but rewarding challenges that startups should tackle.
- Critique of OKRs: Zach argues that Objectives and Key Results (OKRs) are not suitable for software companies and should be eliminated in favor of more tailored approaches.
- Fundraising Insights
- Raising Money is Wasteful: Zach advocates for raising funds as infrequently as possible, emphasizing a preference for organic growth over constant fundraising.
- Misguided VC Advice: He highlights common bad advice from VCs that founders tend to follow, stressing the importance of staying true to one's vision.
- Angel Investing Distraction: Zach believes that angel investing can distract founders from their core responsibilities, preferring that they focus on their own companies.
- Decisions on Exits and Valuations
- Turning Down Visa Acquisition: Zach reflects on the decision to reject a $5 billion acquisition offer from Visa, weighing the implications for Plaid's long-term vision.
- High Valuation Risks: Discussed the complexities of raising capital at inflated valuations and expressed a preference for maintaining realistic expectations.
- Talent Acquisition and Team Dynamics
- Hiring for Spikes: Advocates for hiring individuals with specific strengths ("spikes") rather than well-rounded candidates, as they can contribute significantly to a team's success.
- Experience vs. Hustle: Zach has evolved his view on the value of experience in hiring, recognizing that seasoned professionals can be beneficial in specialized roles, especially in later-stage companies.
- Personal Reflections on Leadership
- Balancing Recognition and Progress: Zach acknowledges his struggle with celebrating incremental progress, emphasizing the need to motivate teams through recognition of achievements.
- Impact of Fatherhood: Becoming a father has reshaped Zach's perspective, enhancing his capacity for love and understanding in both personal life and leadership.
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Key Takeaways
- Founder Mindset: Being overly immersed in "Founder Mode" can lead to detrimental decision-making.
- Fundraising Strategy: A minimalist approach to fundraising can lead to stronger business foundations.
- Team Composition: Hiring for specific skills rather than general competencies is crucial for building effective teams.
- Reflection and Growth: Personal experiences, including parenthood, can influence leadership styles and decision-making processes.
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Conclusion In this episode, Zach Perret shares candid insights on the challenges and realities of leading a successful startup in the fintech space, reflecting on important decisions and lessons learned throughout his journey with Plaid. His perspective serves as a vital reminder of the importance of mindful leadership and strategic decision-making in the ever-evolving landscape of technology and venture capital.
For more information, visit the podcast's official page at [www.20vc.com](http://www.20vc.com).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00I 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. Okay, there's another one. The okayers were built for manufacturing. We don't manufacture software. I think that raising money is like a big waste of time. So we try to raise money as infrequently as we possibly can within plan. Angel investing actually I think is very distracting to founders. Wow, this show packs a punch today and such a joy to welcome Zach Paray to the hot seat. Zack is the co -founder and CEO at plaid, where he's raised over $734 million from the likes of NEA, Spark, GV, Co2 and Andrew Eason to name a few.
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3:07Try UI Paths new AI agents for free at uipath .com. The future of automation is both a genetic and robotic. Don't get left behind. You have now arrived at your destination. Zach, I am so excited for this dude. For me to do this in person is such joy. Also the first time we met in person. So thank you for joining me. Thank you so much for having me. I'm a huge fan of the podcast and amazing how long you've been doing it and how impressive all of the episodes are and Kudos to you as an amazing interviewer. That is very, very kind of you. As I was saying, I did not start quite like this. I would love to start though on a little bit like the refounding moment, because planners had many iterations over the years.
3:45And in the last two to three years, it would seem like there's been like a refounding latest chapter. Can you just take me to that and how that's evolved? So for those that aren't aware in 2020, we signed paperwork to sell the company to Visa In the intervening period, the regulators in the US had investigated it to say that to kind of ask the question, was Visa a monopolist and was this a kind of monopoly creating transaction? And the amazing opportunity we had within the business was we'd grown quite massively from 2020 to 2021. COVID had been a huge tailwind for us. And we had the opportunity to actually walk away at the end of that deal and so elected to do so.
4:18But no, we started working on the new product expansion before that acquisition. Was there a time when you were like, oh shit. We're growing fast again and we're locked into this acquisition. I don't think that there was that specific question on my mind. The question that was always on my mind was, are we undershooting the long -term opportunity by being part of another company? And for every founder that's ever thought about selling a company, that's the key question that they're probably asking themselves. I don't think that most people immediately orient on value of the acquisition. Like sure, yeah, it reaches a threshold and the dollar value starts to make sense.
4:51But I think when people really go through that agony around selling a company It's much more about like am I creating the long -term impact in my fulfilling the mission Am I achieving the vision that I've set out and for me it was always about that You know making the decision to sell the company to visa that was one of if not actually the hardest decision that I've ever made Do you remember the moment you made that oh my gosh. Yeah, yeah, it was my leadership team and I it was right We were doing this off -site student on being the office and we were sitting in my living room and And I'd had them all there, we had this offer and we were going through the pros and cons of it.
5:26And we went around, we talked about what people were thinking and then I kicked them all out. And I was like, I need to think, I'm making this call at the end of the day, I've got all of your input and I just need to think. And it was like me sitting in my living room, my wife is out of town and I'm just kind of alone sitting there. And then I ended up making what I think was a 5149 call to say it's the right answer to sell the business and it's 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 style of conversation.
5:51And that was a 99 -1 decision. I was pretty certain that the right answer was to walk away. I just wanted to make sure that everyone else was aligned. And what had changed in that intervening period is that our business had grown quite massively. We'd reached this escape velocity. And the concept of digital finance had really taken hold as something that people couldn't really live without. Did we build products because of the acquisition? No. Now, the one thing that I did wrong there was we launched three new business areas at the same time. What should you have done? What would benefit of hindsight?
6:18How would you change it? One, then the next. As you would naturally imagine. A bit of a year in between. I think it's hard to do all the things that we did simultaneously. So, once three new business areas, go from being a single product to a multi -product company. That is really hard. Going from one to two products, one to two major product areas within a company, super, super hard. Because you have to figure out how do you sell? How do you balance your sales resources across the two? How do you change your brand? How do you explain your customer that you're not just doing nothing, you're doing multiple things?
6:45Going 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. I have this analogy that I use internally is like, it's gonna be a little gross. It's like a snake that eats an elephant. And you can see this elephant like slowly digesting through the snake. The correct answer is like a snake that eats three sheep, you eat one and then the next and then the next. But like doing one thing where you have a gigantic amount to digest with them in company, super hard. What's the first thing that breaks? Go to market breaks first.
7:15Because how does it break? Every one of the new things that you're doing, the product team that's working on it, wants the salespeople to sell their thing. And the salespeople are getting internally lobbied, like, hey, sell my thing, sell my thing, sell my thing. And they're disappointed when you don't sell their thing. And then the salespeople then have to go explain it to the customer. And all of a sudden, the salespeople are explaining the thing to the customer. They don't know how to sell. So they're like, all right, well, they don't get it. Bring the product people to the sale. So it becomes this really complex go -to -market motion.
7:43And you have to go from having a single sale scene that knows your products in and out to having specialist sales, having technical account managers that are coming to things, engineers that are coming to things. It starts to become this much more complex model. So doing that all at once, I probably wouldn't have done. We also, by the way, went international and started to go up market with our sales all at the same time. So sequencing is the feedback that I would give myself. How did you think about resource allocation between the products? Were you like, hey, split investment across all three, ones are much bigger opportunity, let's put 80 % here in 10 and 10?
8:20How did you think about that? Well, first of all, actually, yes, the shit question. Do you believe that the best CEOs of the best resource allocators? In the long term, yes. It kind of depends on the horizon and scale of the business. Like in this short term, like if you're a founder and you're amazing at finding product market fit, like actually, no, that's the best thing. just go off spend your time on product market fit. At the mid stages is about, can you build an effective company in the long term? When you look at the CEOs that are truly the best, like 10, 20 year public CEOs, they're the best resource marketers.
8:52So when you look at the three products, how did you approach the resource allocation problem? Well, in the early phase, it's very easy. So you build an atomic team as small as possible. You say, go off and figure out if there's something to build here. And I've done that, by the way, with tons of other product areas too. So at a top -mic team, what's the top -mic team? Like a generous team. Yeah, like a product manager, whatever the smallest version of a sufficient team is. So it's a product manager, an engineer, maybe a few engineers, maybe designer, if you need it, maybe data scientists, if you need it, depending on the type of product.
9:22And you just send them off into the ether. And as a founder, your job is like, you need to give them sufficient food to continue to exist, like sufficient resources and attention that they can continue to exist. Soficient protection that they don't get killed by what I call the DeedOS attack, where where if we have a new product that we're working on, we tell the whole company, we have 1 ,000 people now. 950 people are going to reach out to the team saying, I'm super excited, how can I help? 950 messages saying, I'm super excited, how can I help? And actually, like, DDoS is the system, and they're thus not able to move fast.
9:53With this atomic team, you give them sufficient resources, you give them sufficient protection, which oftentimes means ignoring them or hiding them in some sense from the rest of the company. And then you help them figure out how to get to their, are like, at least in our case, to get to their first design partner. So they need like one or two customers that are willing to go experiment with them. So we've done this a lot. This is like how we think about a lot of new product development. And then you do like milestone based financing, which is like, hey, if we find sufficient product market fit, we'll open up new resources.
10:20How do you think about the next stage post -atomic team? Yeah, if you try to over -processize that, then it doesn't really work. Like a lot of people try to run like an internal VC style model, which is like, you know, we'll fund you for a million bucks for a year and we'll figure it out. for a series A style in term. Yeah, and you can do that, but it becomes over -processized, and then everyone starts to try to hack the process as opposed to really finding the unique insight. I'd rather just let people go run it a thing for a while, and usually they'll come back and say, hey, this is not gonna work, or hey, there's something very real here.
10:52They might come back in a week and say, there's something very real here, and I have a customer that's chomping at the bar, like I really need to find it now. I don't want them to wait 18 months to come back and ask for more resources. The flip side, no one inside the company wants to go off in a foray for like three years finding nothing. In terms of the problems that that pursuing, we chatted before and he said to me about a brilliant start of problem that you like called the grind of problems. But I just want to ask, what is the grind of problem and why do you find them attractive to do as a company?
11:22Yeah, so the early history of Plaid was we needed to integrate with all the banks. And these integrations were not like, you know, flip a switch, magically integrations is 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 screen shrapers for the banks because the banks didn't have APIs and like every screen shaper was different. And we had this realization, if we're able just to grind out all the integrations, we're going to be better at 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.
11:50You're like, 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. This was just a mess. In any time, I find a problem like that, and I'm like, yeah, that's it. I get excited about it. And everyone inside the company, 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 difficult. There's a long path. It might not work. And so forth. I just believe that sometimes if you're 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.
12:24Those things that are not necessarily like, it's not about the intellectual brilliance of the strategy you come up with is about your ability and desire to do the work. I love those kind of challenges. So I was talking to a actually one of my partners on the methane team yesterday and they were saying, but there's no defensibility in the company and it's like a seed company. It was like two customers and 400 K and revenue. So there's no defensibility. I'm like, I don't really think any startup has to have a defensibility on day one. Exactly right. On day one. That's the most important part of your statement though.
12:51Are they, if they're coming from 10 years with knowledge of the banking sector, do you see what I mean? Fine, maybe. But ASM intake is in general, if you have two atomic teams, you throw them the same problem, if they have 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 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.
13:19And 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. On the experience side, are there areas where more experience is dangerous? 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 were not going you read any business book, we'd go to great, right?
13:54First is, do you have the right people in the bus? Second is, what the heck are you building? But first is, they get to get to 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, I figured out, to convince myself, trick 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 they didn't accept the offer.
14:23So for me now it's like this intense form of competition with myself. Can I find the person like I love the hunt and then can I convince them to join me? What about discoverability? What I mean by that is like I think recruiting is like a search for the truth and that sounds like super lofty and like I've just wanted to you know J. Shetty book but it's like win loss assumes you want them. Yeah of course. And like actually for me the challenge is determining true greatness. Yeah I mean that's a crucial part of it as Well, finding them, making sure that you're right and then kind of winning. Okay, let's start on finding them.
14:53I heard you were amazing actually in terms of your outreach. Yeah. If you find great talent, it's been your biggest lessons on how to do outreach well. Spear 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 get really good early on at just sending call, email to people saying like, Hey, I love this thing that you do. I'm super, super impressed by it. Will you, 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, my career.
15:21And 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, I started this company called Plaid. I've been super impressed by, you know, whatever you're impressed by for that person. And just say, hey, we're hiring for this job, are you willing to talk to me about it? And you know, they ignore you a bunch of times. They say no a bunch of times, but some people say yes. If you do it enough, then it starts to work. And like that the same thing you can do ever email you do over the phone you get introductions But like it's the same process of like hey, I'm genuinely interested in you and like I have an opportunity that you might be interested in like Can we have a conversation?
15:53Yeah, I totally agree. I think short and succinct is really important totally I get a time where they're like four pages and that's not I This is related to recruiting but but sort of not early on in the company I had a five sentence rule And which is if you write an email with more than five sentences. Yeah, no one's ever gonna read it So write them with less than five sentences. Okay, so we get on the cool or we get in a process with this person in terms of talent assessment. How have you changed your approach mindset, appreciation towards talent assessment? So we have a couple of these core philosophies and one or two of them have evolved.
16:27One 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 like, you know, one certain, you can imagine like a level, like kind of a, if you were to chart this out, you can imagine like they're only reach a certain max on the vertical axis. But if you have spikes in you like make the spikes all kind of work together, then like the level of the elevation of vertical axis is far higher.
16:58So 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 a different background or different ways of thinking about the world. So this 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 more than 15 or 20 years, like kind of wasn't a fit for a plan. We just had this bad assumption that people that had been doing a thing for that long like weren't going to hustle. This was based on our own experience, meaning like we interviewed a bunch of people and either seen friends or ourselves made some hires of people that had been really experienced but weren't willing to work that hard or really jaded in their thinking.
17:36So 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 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.
18:02We do still want this balance though. Like we're in financial services. We want a 70%, 30 split. 70 % of people in our team should not have come from financial services, 30 % should have. What has been the biggest harm mistake that you've made and how have you changed as a result of it? 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 mistake. But let's imagine I'm an early stage company. I can't find the right accountant, but I just need an accountant.
18:30At some point you're actually right. Yeah, you actually do just need an accountant. And chances are that higher that you're going to make is not the right one. You have to dig yourself out of that later. So like, 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. How do you feel about... Obviously PG's essay went in completely viral. How did you feel about it? I was surprised how fire lit went and it clearly struck a nerve for a lot of people. So like, I think there's a lot of aspects of it that are really good.
18:54Why? Why were you surprised by how fire lit went? It's 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 up to me, I brought up to our exact name, like, it was just like this really fast set of conversations. Did you not find it obvious? 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 contacts that he does, then it will actually be a huge unlock for a lot of people.
19:26The 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. I think that that's totally wrong. The second way to read it is the founders should micromanage everything. 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 in work. I think he didn't hit the nail on the head of the whole point. It's like delegate effectively. If you delegate something and it really matters, You're going to stay close to it.
19:59If you delegate something, it doesn't matter. You can say a lot further away from it. Don't over -delegate because I think that 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 certainly made mistakes with over -delegation. But I do worry that it's going to be a little misinterpreted. I totally agree. And it's used as a justification for a lot of bad behavior to happen. And you have people like a Ryan Peterson at Flashboard who is a phenomenal CEO and you who are phenomenal CEO, but not everyone is Ryan or Zach.
20:26And that doesn't mean that bad CEOs, but it just means it's maybe not as applicable. Totally. I think people are going to see that there's Steve Jobs top 100 offsite that he did. People are going to see that and say, I should do a top 100 offsite. They're top 50 offsite, top 20 offsite. That's actually like horrible in a lot of companies. Like 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 like incredible for Steve Jobs at Apple, at the size that they were at the time that it was that thing.
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20:54It doesn't mean that that practice is universally applicable. I also think that building a philosophy of Brian Chesky, who's one of the most amazing leaders, everyone can learn a lot from Brian, but not all of us are Brian. I totally agree. I'm a frabblesom to this blog post on reserve utilization and the importance of reserves in our East -Age Port -Foday is recently. He said, basically, everyone needs to know how you can use them to effectively strive to DPI. And it's like, yes, if you're a brilliant picker, like Fred Wilson is, if he was legitimately one of the best investors in the last two decades, but most people are not very good pickers and concentrate capital into the wrong companies.
21:29What other things are very common beliefs, which many agree with in Silicon Valley echo circles that you're like, I don't agree with that. 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 be willing to go back I can 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 and being really, really unique.
22:01But there are some of these things, I'll take three simple sales. One of the most common early stage things that people will tell small companies is you need to go higher of 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 higher VP of sales for a long time. I hired this group of these amazing young people that would just help me do sales. I was driving sales and they were around me making it more efficient. They were going to show my emails, all the stuff I was ever seeing. That scale was for quite a long time, way longer than it should have.
22:30But in doing that, I learned way more 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 hide the VP of sales early if you don't want to. If you don't think that's right for you, OK, there's another one. OK, there's a built for manufacturing. We don't manufacture software. We're not running an assembly line to create software. Goals are important. But like do it your own way don't just read the indie Grove book and try to apply this thing that worked for Intel to your business if It doesn't actually fit to your business.
22:57It's speed single most important thing for companies going from zero to one No being right is and then speed what does that mean? It being strategically right on the problem that you're solving and then acting with big stream execution speed Yeah, so one of our company values is move fast But you have to be careful when to apply move fast like once you found product market fit But 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.
23:33Ryan and Flite's probably told me very wise, I think he said, velocity is the most important thing, it's speed in a given direction. And I'm like, that's a good one. Well, speed, it's, vice is correct, speed in a given direction, the direction also should be right. Like it should be the correct direction. Do you feel that we've got in a manufacturing line on venture funding companies? What I mean by that is it feels like so many founders get on this production line of, I'm going to hit a million in ARR and then I'm going to raise my A and then I'm going to hit 5 million and raise my B and then 20 and it just feels a little bit overmanufactured and almost forgetting the fact that we build products for customers who give us money.
24:12My 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 the plot. So we go 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, like revenue is growing. Everything looks great. No, we just want to raise money. How do you think about that, though? Because if you want to raise money every three years, say, for example, you're going to have to raise a chunky round.
24:41You're going to have to either take a lot of dilution, or you're going to have to have a really inflated price. How did you think about that? 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 like our business was profitable in the early days. Like not intentionally just happened to be. And so we're like, well, we don't need the money resource.
25:08Like 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. There's a brilliant statement always be raising. Do you disagree with that? Yeah. That seems like I would have wasted a lot of time. What was the hardest funding round? Our seed round was horrible. Why? 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 -200 financial crisis. There's this movement called Occupy Wall Street. And it was like people moved tense in and lived in Wall Street and the big takeaway from everyone was consumers are really frustrated with financial services.
25:40They don't think that the banks are building the products they want. So being 23 -year -old entrepreneurs, we said 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're built a bunch of the details 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 for people, like everybody said no to us, we actually lined up this early funding round.
26:07It's 500K funding round at a $2 million valuation. and the lead investor for this funding round like backed out and it is investing like $100 ,000 or something that and then the rest of the funding run fell apart. And we were out of money. We were basically dead as a company. And so we went to all the investors that had been planning to invest in. We were like, hey, look, the lead has backed out. We 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.
26:38I mean, company, but it kept us alive. It invested 60K to maybe $2 .5 million valuation. That was the 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 there was maybe like six or eight months later that we went back and raised the seed round. It was value that $11 or $12 million. So it could actually a good step up. Did you think you were gonna die? Yeah, but I mean, we hadn't paid ourselves in six months at that point. We were like, whatever. At that point, we're going to actually run out of money. My co -founder was living on a friend's couch.
27:11I'd moved in with my girlfriend because I couldn't pay rent anywhere. I had a moderate amount of credit card debt, which I don't advise to any other founders. But we thought we were going to debt, but we also had nothing to lose. So you just keep going. How did you think about secondaries and money as you progress through the company? Again, I don't want to be at a one -sided journey, as first as founder. like for me making a little bit of money really enabled me to think differently. And I actually super pro secondaries for founders. How do you think about it and did it change your minds at it too?
27:43When 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't get to 100 % of employees. We got to like the large majority of the employees that were able to participate in that secondary. 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. Then we said it was the team. Well, let me finish the whole story.
28:12First it was like, we're selling company for $5 billion. Then we got the end of a year and everyone was like, oh, okay. People don't spend the money practically, but they spend the money in their hat. They do. And then on the. Exactly. And look, who might have said 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. This is a very legitimate buyer. Like there was real cash coming in. And I told them there was a risk. But you know, you spend money in your head. Then we had to get to the end of the transaction and we walk away.
28:42And 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 money. There's a very different aspect of liquidity that was real for them. And then we said, like, 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 I couldn't. Then we got the secondary, then we did as much. Did they respond badly to that? Some of them did, yeah. But not selfishly, just people playing by a house, for example.
29:07Then we do the next round, which was a big step evaluation. And we let people sell us, as kind of, we wanted to create a rational amount of sale, we let them sell as much as we could rationally. But like, you wasn't this full amount. And instead of buying a house, maybe you, something larger than a car, but less than a house, but chunk of what they could sell was the whole thing. That I think was a hard thing for them, good outcome, because they could see the light of the future and the growth of the cloud 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.
29:41And as we were able to do more signers in the future, really focusing on the team is that would be the goal. Are you pleased that you raised a 13 .4 billion dollar valuation? That's a good question. The true value of a private company is impossible to tell. The true value of a private company is what someone is willing to pay to buy an incremental share of that company. That's why you see valuations being all over the place with private companies. In a lot of instances, I wish we had a real -time market market because that would make it much simpler to do things like like compensating employees and doing acquisitions and so and so forth.
30:19The reality is we raised money in the situation and in the environment that we were in at the time. Puzz values have gone down since then. Frankly, the value of the company has gone down since then. And by the way, as a founder, your job is to raise money and die in some cases as little as possible. 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 deeper responsibility to the investors in the invested in the plan. I want every one of them to make a lot of money on plan. That means that my expectations for the company are really, really high.
30:52I 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, but the reality is that the multiples have changed. You know, we're in a long journey. I've got work to do. We've got to make sure that invested and if we're lucky enough that the investors continue to hold through that entire period, like I really believe they'll be able to do it, but that takes patience. Did it enable you to do things that you couldn't do earlier?
31:21Yeah, exactly. Because that's the only thing that is cool. Like Instagram and Facebook, everyone's like, oh, what a mistake. I can't comment on Instagram and Facebook. The structure that we set up with Visa was that we were running as independent entity. We had access to all the tools internally. I was the CEO of the independent company and we could run as fast as we wanted to and the direction that we wanted to and we got a boatload of funding to go do it. That's not the worst setup. up now I like the independent path better. No answer is. I listen to it. I talk to you. It was a hard question.
31:48When we look at M &A more broadly, you know, I'm an investor, we think about liquidity now and we'll never. And there is no fucking liquidity. There's no liquidity for LPs that choked up to their neck with lack of liquidity. And I look at M &A first and it's just completely shut. Is that a fair representation? And do you think M &A is completely shut one? What do you think it will lead to it opening? So far as I can tell, I think the large MNA transactions are mostly getting deeply investigated and often them blocked by the regulators. That political environment will change eventually. We did see some of these odd, like, aqua -higher, large AI acquisitions, which have been fascinating, but I don't think that works with a company that has tons of contracts that they actually want to transfer over to the acquired company.
32:31I can't predict the future, but I do think that it's pretty hard to do a large MNA right now. On IPOs, another form of liquidity. How do you think about IPO markets today? It's something again that as a late stage value you always have to be in love and await too. How do you think about IPO markets today? The viability and the excitedness 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 and a fundraising event.
33:02When you need the capital, when you need the milestone, when being public is really useful to the company, then you should go do it. But now it would be inherently unattractive time for you to go public. Yeah, it would be for a variety of reasons. I'm sure that'll change in the next, I don't know how long. But are you going to be in the early days of your world? I would say companies, I'm not going to hear as I said this, but companies of your profile should go public, should take the head on valuation, and they will grow into great companies in public markets. Well, I definitely believe that we'll grow into a great company, if we're not there already.
33:31And they would love to have that increased trigger 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 and so forth. But on the flip side, you know, it is a milestone and it is a very useful tool for us to do at some point in the future, but that day is not today. And that day will hopefully be a good deal.
33:56Someone said a great statement to me the other day. They said, they have the highest things in life and not iron or gold, but unmade decisions. What unmade decision weighs on your mind most? Philistophically, I have a very high -partisist driven decision making model, which is you ask me a question, I have an answer. It's not a deeply held answer always, but I 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 strong end of what the decision is. I'm not sure I have a specific unmade decision. Does that not get you in trouble with your wife?
34:26All the time. Yeah, it 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 playing to ask this question later, which is like, what's the question that no one ever asked 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, what's the answer? Red or blue? Red. How confident are you? Zero percent confident. How much do you care? Not at all. Like those three need to go strong. Okay.
34:50So I'm exactly the same as you, but someone said to me, why is he the other day? You forget Harry is the weight of your words. And you said that with real confidence. And the team just went with it because of that. And I'm like, oh shit. And so do you worry that actually your words carry a lot of weight? And because you do say things with great confidence, it's like, shit, that said that. I mean, let's do that. 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? What's your biggest floor as a CEO? One of my biggest flaws as a leader is, I'm not great at recognition of progress if the outcome is not excellence.
35:27Let's say we have some problem with the company and currently we're operating at two out of ten going from a two out of ten to a four out Ten you've just made something twice as good my CEO tells me the seller time He's like you got to celebrate that if 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 two to a four out of ten Sometimes that matters quite a lot personally. I am like never never okay celebrating that because my answer is like that's a four out of ten It's like like, we're still horrible. And objectively, that is the correct answer if we stay a 4 out of 10.
35:58But oftentimes, the trajectory is you go from 2 out of 10 to a 4 out of 10 to a 6 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 like interim milestones that are not yet perfect, it's been really hard. And it definitely discourages people within the company, giving the internal praise of, hey, like you made progress there. Like let me cheer you on and like be the cheerleader to help you go from 4 out of 10 to a 6 out of 10 to an 8 out of 10. That's really hard. I do feel strongly that you should never celebrate something that just factually isn't good.
36:28If we're delivering something at a 4 to 10, that is factually bad. We should not be celebrating that we're delivering a 4 to 10, but we should celebrate the progress that we're making and the trajectory that we're on. Finding a way to support the team through that terrible to good, to great process. I do think in the early days people don't talk about manufacturing wins, which is often that it's just not much to celebrate. It just doesn't look that great. And I think your job as a CEO is to manufacture almost fake or small wins and to alleviate them into bigger wins just to carry teams through a bit stagnant times.
37:00You know, I was talking to an entrepreneur friend of mine who had a deep respect and they said, you know, we said a big hairy audition school. 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 a big hairy audition school? The big hairy audition school, I've always done. The what's the first thing you can celebrate question? I've never done and I love it It's a huge on that 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.
37:27I used to run my since when I was you know young and I had good knees But always you always break down by five miles just the next five miles just that if you look at what do you celebrate the five miles when you get to them Absolutely, I would have a jelly bean Jelly beans jelly bean just get that Or just an I'd actually varied up with a Lucas A don't Martin or whatever that is, but I think that's really important What trait do you have that you're a little bit ashamed of but it's also contributed to your success? I'm very independent, like very self -sufficient. The downside of this is comes from a childhood of a bunch of weirdness that I won't go into now, but people find it very hard to get to know me.
38:08They find it very hard to read me now within the company So I try to be more, I try to tell people what I'm thinking. I try to let my face be expressive, which is not, it isn't naturally, usually just smile, no matter what I'm thinking. But people find it very hard to get to know me, very hard to read me, very hard to empathize with me. On the flip side of that, it allows me to live in my own universe for decision -making or big thinking. So my favorite times are sitting on your plane. No one needs to talk to me. I can just sit there and think, I put my headphones in, I don't play anything, so I'm just going to play static.
38:40And they sit there and think and I have a notebook and a race to step down. And like this, like, it kind of self -sufficiency isolation, I find it gives me clarity in a place that otherwise I might not have. Do you enjoy your own comfort? They will own like company. Oh, yeah, of course. Not many do. I feel very fortunate though. Okay, final one for you to a quick fire. Becoming a father is an incredibly seismic moment in one's life. How did becoming a father change you as a person, one, and as a leader, two? It's a good question. And 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.
39:16For 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 who you've known for so long, you think you know super well and then you just see this totally new aspect. You know, it made me think differently about, you know, what are the underlying aspects that other people in my life might have and how might they change every time and being more open and accepting of that.
39:48What is the XAST -T today? 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 far. I fall into that trap absolutely as well. For me, it's like excellence, which is like, it doesn't have to be bigger. There's nothing to be fast driven, but it's like whatever we do, it has to be great. I care about the craft of interview and we don't have to do more shows or that show or whatever, but they have to be really good shows. And whatever we produce, it has to be great. Is it internally driven or is it externally driven? Do you have a threshold?
40:21That 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 so objectively really good, would that be okay? No. Yeah, exactly. So much of mine is driven through it, so I don't know. Competitive. Yeah, what's the right way to approach competition? I don't know. I love it though It's like drives me in my day when I see a competitor do something that I think we should have done I think self competition is the answer to that at least for me at some point like 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 Can I just ask one on on the investing side sure?
40:57It's like you have the fun now miss you for me. Yes. Yeah, so This might be spice, but you raise money for a plan and you are a brilliant CEO in that respect. And then you decide, I'm going to invest. I'm like, if you're an angel investing, game on. You do whatever you want. So your money, go for it. But if you're raising money from other people and then spending time investing their money, to me, I'm like, is that not a distraction to the core and to the investors that you've had invested in a plan? And actually, that's not how it should be. How would you respond to people who believe that? So that's a good framing and I appreciate the spice.
41:36Going 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 in later stage. I was spending time with the gigantic banks, I was spending time with the gigantic companies. I found that Plaid was in sometimes losing some of the founder mentality. It was losing some of the fine grain detention 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. I had reasons to go talk to founders, had reasons to engage with them deeply.
42:09It kept me fresh. It built a great network. I learned things that I brought into how we developed products at PLAD. I met amazing people who ended up hiring and it's created this really virtual 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 the 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 learned a lot, but it doesn't have that much meaning and it takes too much of my time.
42:44And 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 fun structure that I have max leverage. They run it full time, three full time people, and me who does it a few years weak, but I get to spend time talking to entrepreneurs, helping them through sticky situations. And the amazing thing for me is like, I talked about sending emails and people responding. Like the wisdom and the value of Silicon Valley, and I say Silicon Valley and like air quotes here, because it's not about being in the place, that enabled me to be an entrepreneur.
43:20That taught me everything that I know. And I think there's a value in paying it forward. and so what oftentimes happens is, you know, we have these WhatsApp threads with the founders and the last some 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 them flat. Like, hey, how do we think, like 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 an immune product innovation? So I'll share that with them flat.
43:45I'll share that with all the founders. And like, sometimes we'll even do a Q &A which will record and then we'll have this artifact. And so for me, it makes me a better entrepreneur to go deep on these 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 pay -it -forward mentality with the founders of Inter. 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. I agree completely, but we've moved from like a boutique industry to as Doug Leone equals it to like a commoditized asset class.
44:17Yeah, so the question is the VC product kind of played out. I think it's kind of played out. Yeah Do you think VCs add value a few in what way has the VC moved the needle for plant? There have been a few one of them was transformational where VC came in and said we'd around those falling apart for Very unrelated reasons they came in said look we're gonna We're gonna stand behind this we're actually gonna be more money to higher valuation And it's gonna like meaningfully change the trajectory of the company because there was some some risk on the round that that kind of came up mid -round and they were like, no, we believe so, so deeply in the company.
44:47And so like that decision to invest at the right time made a huge difference. Who was that? They'll love it. That was any A. Like they, I think the world of them and like the way that they handled that situation was truly incredible. That's awesome. They'll love that. That's good promotion. This is not who waterways. That'll be thrilled. They're not. Rikying. Amazing. Ravi, the smile. I spoke to him before. Actually, yeah. He said you're a dick. I swear. I don't think he's ever said that word was less. Yeah, and he's way too nice. That was just me. but we'll cut out that last sentence from me and then he'll just be pissed.
45:17Listen, I want to do a quick fires at I say a short statement. You give me your immediate thoughts, sounds OK? Yeah. What book written before 1965, would you most recommend? Ah, man, too many. The wealth of nations? What's the most contrarian or unall -sox advice for founders, listening? Most of the stuff that the VC's tell you don't do it. That's not to say, like, totally ignore them or like telling their own private. What's the most dangerous trope that VC's often say? The OKR stuff, like putting OKR in a business way too early is totally wrong. Putting revenue metrics on a company before they've achieved product market fit totally wrong.
45:48Like 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 like let them have space. Totally wrong. Don't like micro -many is them too much, but like stay close. You need to stay in the details. You need to understand what's going on. What have you changed your mind on most in the last 12 months? So many things. We were talking about experience. It's like I've just been proven time and time again that hiring for experience in certain pockets where deep industry expertise matters is really, really important.
46:16And so that's been like, it just really in my face a couple times. What technology or advancement is most underrated? The last time I had this like, oh my gosh, the internet, this is the way that technology is going to go. Like there been a few of them recently, like trying the meta -ray bands, it's like, oh my gosh, like this is a thing that's gonna happen. Like I'm dealing with some of the AI stuff that's been fascinating. Like 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 by. And it was like, ah, that's how the internet's supposed to work.
46:43And I think that that innovation is underrated. Like everyone's like cloned it now and like, you know, PayPal's done it and stripped it. Like everyone's like built the same thing. But the first time I saw that, like they had this, this incredible advantage, relatively the rest of the market. So it was very cool. If I ask you in five years time, where would you be exceptional for the plan to be and why would be a fail? What would the answer be? If anyone can get credit, a great asset to credit based on the data that they have with them in their head, your transaction history is so forth, you have the ability to link that based on the data you have in your head.
47:14That would be a huge unlock. I think if financial fraud, which right now, at least in the US, is growing at an increasing rate, if we can have it either flat or growing at a decreasing rate minimally, ideally declining, that would be huge. And so I think we can very realistically do that. And I think if it's a one -tap experience to apply for alone, that's the threshold that we have, that's the target that we have. It's like, I want to apply for alone, click Apply, do a Face ID, great, your application is spent. That's the goal. Zach, thank you so much for putting up with my variations and moving around schedules.
47:51You've been fantastic, and I've so enjoyed this, man. It's been super fun. Thank you for having me.
48:01I have to say that was such a special one for me to do. We first did our first episode together seven years ago, so to have the chance to do that in person was just fantastic. If you want to watch the full episode you can find it on YouTube by searching for 20 VC, that's 20VC. But before we leave you today, I'd like to introduce you to one of my favorite brands, Atio. Atio is the next generation of CRM. Setting up Atio takes less than a minute, and in seconds of syncing your email and calendar, you'll see all your relationships in one place, all in rich with valuable data. Atio also lets you build zapier style automations, gives you powerful reports and works perfectly for any go -to -market motion from PLG to sales -led.
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50:34Try UI paths new AI agents for free at uipath .com. The future of automation is both a genetic and robotic. Don't get left behind. As always, I so appreciate your tuning into the show and stay tuned for an incredible 20 growth on Friday with Antoine Lennel, head of growth at Revolut.
From the publisher
Zach Perret is the CEO and Co-Founder of Plaid, a technology platform reshaping financial services. To date, Zach has raised over $734M for Plaid from the likes of NEA, Spark, GV, Coatue and a16z, to name a few. Today, thousands of companies including the largest fintechs, several of the Fortune 500, and many of the largest banks use Plaid. In addition, Zach is also a Co-Founder of Mischief, an early-stage venture fund in San Francisco.
In Today’s Episode with Zach Perret We Discuss:
1. Founder Mode:
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Why “Founder Mode” will be the most dangerous blog post written in the last decade for founders? What is most misleading about it?
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What are “grinder problems”? Why does Zach believe that grinder problems are the best problems for startups to try and solve?
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Why does Zach believe that OKRs are BS and should be removed? What should be used instead?
2. Lessons from Raising $734M for Plaid:
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What is the worst advice that VCs give that most founders take?
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Why does Zach believe that angel investing is more distracting than helpful for founders to do? What are the pros of investing alongside running a company?
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Why does Zach encourage founders to raise money as infrequently as possible? What does this mean for the size and price of rounds Zach thinks we should see occur?
3. The $5BN Exit and the $13.4BN Round:
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Why did Zach turn down the $5BN exit to Visa? Was it the right choice?
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Does Zach regret raising at such a high price of $13.4BN when the exit did not happen?
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Would Zach sell the company today for $13.4BN if offered it?
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What did Zach not do that he wish he had done? What did he do that he wishes he had not done?




