The Ledger

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Disclosure
Petersen: SoftBank led Flexport's $1B round and urged undercutting rivals by 10%
“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…”
Ryan Petersen Jun 20, 2026 ▶ 1:12:18 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport is struggling to get employees back into the office
“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 …”
Ryan Petersen Nov 13, 2023 ▶ 55:51 Ryan Petersen: Why Velocity not Speed is Most Important in Company Building | E1081 · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport reaches $450 million net revenue run rate
“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.”
Ryan Petersen Jun 20, 2026 ▶ 9:51 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport will shift to open-source AI models to lower costs
“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.”
Ryan Petersen Jun 20, 2026 ▶ 15:02 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport won major client after competitor laid off embedded worker
“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…”
Ryan Petersen Jun 20, 2026 ▶ 23:04 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Peter Thiel offered Flexport $300M valuation after Petersen asked for $275M
“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…”
Ryan Petersen Jun 20, 2026 ▶ 33:20 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport mandates a five-day in-office baseline requirement
“We're five day a week in office as the baseline assumption at our company.”
Ryan Petersen Jun 20, 2026 ▶ 38:15 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Flexport Operated at a 13% Take Rate and 6% Profit Margin
“Our take rate on the freight is 13%, our margin six percent”
Ryan Petersen Dec 2, 2016 ▶ 13:16 20VC: Flexport's Ryan Petersen on Why Investor Relations Are Overrated, Why Boards Have To Be Rethought & Why MBAs Do Not Make Bad Entrepreneurs
Disclosure
Ryan Petersen: Driven by power and doing big things, not money
“Yeah, I mean, I haven't been that motivated by money. I'm more into, like power. I want to do big things.”
Ryan Petersen Jun 20, 2026 ▶ 8:45 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport spends $5M annually on LLMs, spend doubled recently
“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.”
Ryan Petersen Jun 20, 2026 ▶ 15:53 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Ryan Petersen: Flexport's largest customer spends $150M annually on logistics
“Spend about a hundred fifty million a year.”
Ryan Petersen Jun 20, 2026 ▶ 23:59 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Ryan Petersen: Flexport has a dozen customers spending over $50M annually
“We don't have too many like that, but we have probably a dozen that spend over 50, and then a long tail.”
Ryan Petersen Jun 20, 2026 ▶ 24:03 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Flexport's logistics business serving data centers is growing rapidly
“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.”
Ryan Petersen Jun 20, 2026 ▶ 25:12 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Only 4% of Flexport's workforce is in San Francisco
“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.”
Ryan Petersen Jun 20, 2026 ▶ 36:41 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Ryan Petersen: I was the first angel investor in Rippling
“I was the first investor in Rippling. Put a big check into that. Did really well.”
Ryan Petersen Jun 20, 2026 ▶ 52:17 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: Sam Altman Was One of Flexport's Earliest Investors
“Sam was one of our early, earliest investors”
Ryan Petersen Jun 20, 2026 ▶ 58:03 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen quit angel investing because time away hurts Flexport
“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.”
Ryan Petersen Nov 13, 2023 ▶ 52:58 Ryan Petersen: Why Velocity not Speed is Most Important in Company Building | E1081 · 20VC with Harry Stebbings
Disclosure
Petersen: Flexport holds less than 0.1% of global logistics market
“We're still less than one percent.1%.”
Ryan Petersen Jun 20, 2026 ▶ 11:00 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Petersen: I change company direction too easily
“I'm very good at changing direction, probably change direction too easily also.”
Ryan Petersen Nov 13, 2023 ▶ 43:43 Ryan Petersen: Why Velocity not Speed is Most Important in Company Building | E1081 · 20VC with Harry Stebbings
Disclosure
Flexport Founder Ryan Petersen Graduated Columbia Business School With $140k Debt
“I came out with a 140,000 dollars in debt”
Ryan Petersen Dec 2, 2016 ▶ 5:16 20VC: Flexport's Ryan Petersen on Why Investor Relations Are Overrated, Why Boards Have To Be Rethought & Why MBAs Do Not Make Bad Entrepreneurs
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