Flexport

“The company I recently invested that I really like is Flexport, which is an end-to-end freight forwarding company.”

“We didn't have a board at Flexboard until we'd raised thirty million dollars and just created the board after the Series B when we raised another 65.”

“Our series B was Done almost entirely by insiders, by people who had been in the series A and even, and a lot of the money came from people who were in our seed round.”

“Most of them have been amazing, like connecting, making connections and stuff, but we would have pretty much had the same company without any given thing that any of them did besides give us lots of money.”

“The licensing part turned out to take three, three years. So I had this, like, proof of concept, and then I had to wait three years before I launched.”

“If we really succeed, if we fail, we'll just build the best customer acquisition and service model in a trillion dollar industry and still do quite well.”

“It's about seven years of runway right now.”

“If you do a great job, you get some traction, you get progress, you build, you know, you start really doing something, especially you raise some money. Now, all of a sudden you can go recruit your co-founders. And so that's what I did basically was One, I had …”

“Partially because I, this is my third business and the last one makes five million dollars a year in profit.”

“I'm not, we're not going to sell the business.”

“We got in one year, 300 companies to sign up, and I thought it would be all small businesses like my little e-commerce venture, but among the companies that signed up were Foxconn, the maker of the iPhone, Cargill, which is like one of the biggest commodities …”

“Our take rate on the freight is 13%, our margin six percent”

“At SUSE, we've made about 50 investments over the last four years. And Flexport was the only one where we made it, like, we basically made the call during the first meeting where we just said, okay, like, we want to be a part of this.”

“Backing, and I cannot believe I'm saying this, Dad, but an incredible two unicorns per year since founding, including Shopify, Opendoor, Flexport, Adyen, Twitch, Fitbit, and many more incredible companies.”

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

“I think being generically right and specifically wrong is extremely Extremely dangerous as a leader, so you have to actually dive in and really understand the details of what people are doing.”

“It kind of reminds me of Flexport or something. It's the people who are telling you they're going to automate everything they do. I also am quite Skeptical.”

“Yeah, I think the most the most compelling first pitch I had was Ryan Peterson at Flexport.”

“Personally, my biggest tip from a cashback perspective is Flexport. I think rough numbers, when I invested, it was like, 15 cents a share, and I sold at 25 dollars and 40 cents a share.”

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

“My first angel investment ever was Flexport.”

“And I like to hire entry level jobs out right out of colleges. Yeah. Because you don't have, you haven't learned any bad behavior. You know, you haven't gone to a company that's not very good at things and learned a bunch of foundational elements that Are wron…”

“What I saw was the power of multi-tenant, you know, the power of you know, multiple companies being able to benefit from the scale of the total, and the rest of the world needs that, you know, the rest of the world needs that for the environment to pull carbon…”

“But we're not a family because we're all here to do a job and we have a set of roles and responsibilities and You know, you have to deliver on performance. You know, it is a team. I think that's a much better way of framing it than a family.”

“You really only know if you're customer-centric in a very, very hard moment where you're faced with doing something that the customer would like, but it's going to cost you a lot of money that you really, really, really don't want to spend.”

“But in fast growth environments, like I was at Amazon and like we're in it flexed work you often have to intersperse more senior external talent because the business, the people who grew up internally, they haven't, don't have exposure to the business you're b…”

“We raised a billion dollars in 2019 and then in 2022, we raised nine hundred eighty four million dollars. That turned out to be true. Like that we were kind of at the peak of the bull market and that balance sheet serves us very well today that we have a billi…”

“Flexport is struggling to get team members to come back to work right now. And I, it wasn't, you know, it wasn't our focus the last few months, but it's absolutely my focus right now. I'm pretty frustrated by people at Flexport who don't want to come into our …”

“We cut 27% of our costs already in my first five weeks.”

“Over the long run, 50 year period or something, the CEOs who have the best returns in the stock market have been really good at resource allocation, meaning, meaning they really understand when their stock is overvalued or undervalued. And if it's undervalued,…”

“A lot of our best customer relationships are people that we royally screwed up with five years ago, but it's how do you respond in that moment?”

“We let go of a lot of amazing people a few weeks ago. We let go of about half of our engineering team. We know we grew our engineering team this year from 450 software team members, product and engineering team members to 1300.”

“So we, what we do instead is we grab four or five, six people for whatever the topic is that we need. And we'll go deep and not just those six people who report to me, but some usually the layer down from the technology or someone from the front lines who unde…”

“Finding people at Flexport who are focused on anything other than making Flexport successful at work, It's like really, really frustrating. I don't care what you want to focus on outside of work at all, what your politics are, what your cause is. I think that'…”

“Don't hire outside people. I rather much, I don't hire senior executives. I think in almost all, I'm not, look, that's not a blanket rule. We've hired a lot of great senior executives at Flexport over the years, and a lot of them are doing amazing work for us,…”

“I actually quit angel investing a while ago, basically. I'll do it a little bit here and there if it's a friend of mine or something, but the reality is any time spent away from Plexport is probably net negative for Flexport.”

“Your values don't really count unless you're willing to give up money for it. Otherwise it's just word on the wall.”

“I think remote work is Very, very difficult to achieve a build a company culture. I think individuals can succeed. I'm incredibly productive working in my house with there's no distraction. I'm incredibly productive individual contributor, but great things get…”

“I'm very good at changing direction, probably change direction too easily also.”

“Flexport's now the third largest of the American companies and top 10 globally. And if you look at the top hundred providers of global freight forwarding services, customs brokerage and freight forwarding, we're the only one founded after the web browser was i…”

“Flexport delivered thirty-three million packages to consumers' homes. That's what we're on track to do this year.”

“I've done a 115 customer calls. In the first eight weeks on the job try to do four or five every single day.”

“I don't think speed is the most important thing. I think it's velocity. And if you remember your physics, velocity has a vector. It's speed in the right direction.”

“And if I just think about all the great people have left Flexport over the years, If they were still here, we'd be like 10 times better company.”

“We've got a roadmap to get the company profitable by next year, by the end of next year without raising prices for our customers.”

“The first big check that I wrote at Founders Fund was Flexport. And no one was thinking about Supply chain logistics in 2014.”

“Did I have like some super crazy interest in supply chain and logistics or a thesis in supply chain and logistics before I invested in flex work? No, of course not. Like I needed Ryan to like convince me of the timing to the market.”

“So when I wanted to make the flex board investment, I had to kind of go through the gauntlet and answer a bunch of questions from the team and pound the table. But at the end of the day, they were like, we made a bet on Trey. Trey has high conviction in this. …”

“I don't really want a more active board. They're not super active in the business. They're not like telling us what to do. They don't help that much, but they don't ever hurt. And like, I would much rather have that than like a really helpful board. I don't th…”

“We're five day a week in office as the baseline assumption at our company.”

“It might be about the same. We're hiring a lot of salespeople and we're expanding a lot in new markets, but I think you're going to see like a shift from people that today do operations, kind of manual work that I was describing earlier into, okay, you've got …”

“Yeah, probably. I mean, I don't know about Anthropic, but on LLMs.”

“I'd like to be a nicely profitable, making a few hundred million of EBIT and then we'll go public. So it could happen in a couple of years. It should, like the way that things are going right now, we should be able to get there.”

“We're still less than one percent.1%.”

“I had, like, a lot that seemed like they went well, and then they never invested, and the number of investors who ghosted me, by the way, after the pitch, the vast majority, I would say. Where I pitched him, it seemed great, and then it's just like, never hear…”

“And we had this recent, we just had this huge customer win, one of our biggest ever. And I was like, wow, this is great. But I had heard that our competitor makes their Has one of these forward deployed logisticians, like, and runs their RFP, runs their proces…”

“My first Excel my first and only financial model that I made for myself for the business got to one million of revenue, right? Like, we did over two billion last year, so.”

“We've got about, well, Probably like a hundred core workflows that are costly that we have AI that we're building AI agents for right now. And like five of them are live and working and saving us money and 95 that are under development.”

“And I need at least like 80% of those to come to life and like actually have the impact. Otherwise we're just spending money and not getting much back for the AI.”

“I mean, by the way, our competitors, like us and others that are scaling, that are serving data center companies, that part of the business is growing like crazy, because there's data center, all this physical, the data centers have to be built.”

“And I think we'll do 600. I mean, the goal is to keep going 30% every year for 10 years.”

“Sam was one of our early, earliest investors”

“Well, I got, I say it's white collar fraud.”

“We're on run rate to do about four hundred fifty million dollars of revenue, net revenue. Breaking news here, I haven't shared that, but four hundred fifty million of net revenue.”

“Best offer I got was two 75, but the firm wants board control. So if you'll just do it without taking the control of the board, you guys can have it. And Peter just offered 300 instead of two 75, which wasn't as good as my 500, but he didn't need to do that. I…”

“Yeah, well, they led the round of a billion, yeah. And he was like, whatever the price of freight is, you'd just be 10% cheaper than everybody, and then if someone matches you, you'd just be 10% cheaper than that, which is like a terrible strategy. I did not d…”

“Spend about a hundred fifty million a year.”

“I think this year we're gonna get to basically break even.”

“I don't need to raise any money ever again.”

“I think we're spending like probably like five million a year or something ramping pretty fast though. Like it's doubled. The last few months.”

“And like, there's a limit to how many relationships a human can have. And I think you can probably use those to use AI and use other techniques to like double that ratio or something, but like there's some limit to how many relationships you can maintain. And …”

“I mean, one of the big tech companies that runs like a hyperscaler, let's call it has one of our direct competitors has 130 full-time employees that work at that company that have badges that show up to work every day that run their logistics for them. And we …”

“Like, our team in San Francisco is maybe four percent of the companies based in San Francisco, even though that's where we were founded and where I'm based.”

“Yeah, I do. And I've, I, as measured by when I tell my sales team I'm going to do less of it, they always push me to go do more press. Like they say that it helps them get deals and close deals and stuff.”

“Almost all of our competitors have had major hacks in logistics. Like, it's been a major target area for cyber, and there's been a lot of, like, ransoms.”

“For the last decade, I wanted to be, I didn't want to compete on price, and I wanted to be the premium value, premium provider in logistics and thought it would be bad to compete on price. And now I'm like pretty convinced that we need to be the low cost leade…”

“So I'm like pushing, I'm probably, Gonna start pushing more of our employees like, hey, you should come move back to San Francisco.”

“I don't want to dedicate that much of our engineering resources to replacing SaaS. Like I want to build, I want to replace work, like expensive labor, and I want to build our product and make it way better. So I don't, I want to, like, focus on our core busine…”

“We don't have too many like that, but we have probably a dozen that spend over 50, and then a long tail.”

“We're using OpenAI. We're using Anthropic. We're going to increasingly use open source models to save money, but also because we don't today have a budget constraint on our Anthropic contract.”

“But agents can go all the way. Like, we think we can automate the full end to end.”