Flexport, every mention

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every year anyone Harry Stebbings 99Ryan Petersen 72Roy Bahat 7Dave Clark 7Wesley Chan 3Trae Stephens 2Sheel Mohnot 2Leo Polovets 2Garry Tan 2Fabrice Grinda 2

Verbatim, from the transcripts: the passages where Flexport comes up

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DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings Jun 25, 2026 · 2 mentions

  • ▶ 1:12:42 Harry Stebbings Ryan Peterson at Flexport said, kind of jokingly, obviously, um, work from home is white collar fraud. 2 times in the scene

Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings Jun 20, 2026 · 24 mentions

  • ▶ 0:15 Harry Stebbings Our guest today is a longtime friend of mine, Ryan Peterson, founder of Flexboard.
  • ▶ 9:40 Harry Stebbings If Flight Sport would have raised today, what do you think you'd raise at? 2 times in the scene
  • ▶ 11:38 Ryan Petersen I don't, I don't think about it at all for Flexport. 3 times in the scene
  • ▶ 18:45 Ryan Petersen Our business has just tons of manual operations with humans, like, forwarding email. 4 times in the scene
  • ▶ 31:11 Ryan Petersen So, uh, our Flexport Series B round, and we, I, we were like a hot company.
  • ▶ 35:44 Ryan Petersen Like, the fact that we're a Founders Fund company has made so many other investors want to invest in Flexport and like.
  • ▶ 38:54 Ryan Petersen I mean, I think that all the bad things that have happened at Flexport were when I didn't do what I wanted to do and was trying to, like, you don't want to ever be afraid of your employees, first of all.
  • ▶ 50:42 Ryan Petersen I, I used to do a ton of it, um, early days of Flexport. 2 times in the scene
  • ▶ 56:28 Ryan Petersen I left my partner there, my co-founder, or like my, the president of Flexport, he stayed behind, and I said I had to take a phone call, and I just never came back. 3 times in the scene
  • ▶ 1:06:36 Ryan Petersen And it was a newspaper, I mean, Bloomberg's not a print, but it was a, it was front lead of the story that Flexport, we used DoorDash to do the delivery.
  • ▶ 1:13:13 Harry Stebbings When have you been most nervous in the Flexport time? 4 times in the scene
  • ▶ 1:18:07 Ryan Petersen I, I don't, I don't think our Flex Sports board needs anybody, uh, the board is like mostly there to represent the interests of our, the investors and make sure we're doing a good job, not like.

Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings May 9, 2026 · 1 mention

  • ▶ 51:45 Harry Stebbings I'd have a seed check in Flettersport, seed check in Vanta, and I knew all these guys were great, but I wasn't sure they were like 10 out of 10, and the honest truth is the market.

How Hims & Hers Reached a $4.3BN Market Cap on $2.3BN of Revenue | Andrew Dudum · 20VC with Harry Stebbings Apr 4, 2026 · 1 mention

  • ▶ 8:33 Harry Stebbings Cause we have the founder mode and the, you know, I love Ryan at Flexport, but like that I'm so in the weeds and I love him for it.

Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings Dec 6, 2024 · 1 mention

  • ▶ 51:28 Zachary Bookman The, the checks I wrote in 1315, 17, you know, fantastic companies, you know, uh, Flock Safety and Adapar and, uh, uh, Qualia and Flexport and other things.

Zach Perret: Why ‘Founder Mode’ is the Most Dangerous Blog Post for Founders | E1215 · 20VC with Harry Stebbings Oct 16, 2024 · 2 mentions

  • ▶ 20:14 Harry Stebbings And you have people like, uh, Ryan Peterson at Flexport, who is a phenomenal CEO, and you who are a phenomenal CEO, but, but not everyone is Ryan or Zach.
  • ▶ 23:57 Harry Stebbings No, I, I tend to get you, uh, Ryan and Flexport told me very wisely, I think he said, velocity is the most important thing.

Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings May 8, 2024 · 1 mention

  • ▶ 1:03:57 Harry Stebbings I always remember Ryan at Flettersport said to me, like, it's not speed, uh, it's velocity, which is speed in a given direction.

Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings Apr 3, 2024 · 7 mentions

  • ▶ 14:48 Trae Stephens And so like two great examples, um, you know, the first big check that I wrote at Founders Fund was Flexport.
  • ▶ 17:57 Harry Stebbings and you are partners, and you say, Harry, Flexport, Ryan's fucking amazing. 4 times in the scene
  • ▶ 19:08 Harry Stebbings Say you have a really competitive deal, say Flexport suddenly gets 10 term sheets and some of the best firms in the world alongside you are competing for it.
  • ▶ 44:18 Trae Stephens 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?

Ryan Petersen: Why Velocity not Speed is Most Important in Company Building | E1081 · 20VC with Harry Stebbings Nov 13, 2023 · 65 mentions

  • ▶ 1:57 Harry Stebbings In the spirit of adventure that takes you to China and reselling scooters, motorbikes, how does that lead to Flexport with your bro?
  • ▶ 4:13 Harry Stebbings And how did you reflect on your life and Flexboard in that period? 6 times in the scene
  • ▶ 5:52 Ryan Petersen I mean, I came back to the company about two months ago. 4 times in the scene
  • ▶ 7:42 Ryan Petersen The other things I learned is how much customers like Flexport Capital. 4 times in the scene
  • ▶ 14:38 Ryan Petersen So like who cares what evaluation is right now, according to some outsider who doesn't even own Flexport stock and writing an analyst opinion on it. 4 times in the scene
  • ▶ 17:43 Ryan Petersen We let go of a lot of amazing people a few weeks ago. 2 times in the scene
  • ▶ 25:54 Ryan Petersen So what the way that Flexport works is
  • ▶ 26:53 Ryan Petersen I haven't even mentioned there's a bank that's financing that transaction or it's flexible capital.
  • ▶ 29:51 Ryan Petersen Uh, you know, Flexport's mission is to make global commerce so easy.
  • ▶ 33:44 Ryan Petersen 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, but it's so much higher risk. 5 times in the scene
  • ▶ 36:43 Harry Stebbings Your wife said, what's the biggest misconception people have of Flexport today versus what it is really? 18 times in the scene
  • ▶ 46:06 Harry Stebbings You are a CEO of a, you know, a thousand plus, how many, how many people work at Flexport now?
  • ▶ 48:14 Ryan Petersen How to get the media to like, well, I was building Flexport well before I met her. 2 times in the scene
  • ▶ 49:36 Ryan Petersen And I've started multiple successful companies, not just Wexport, but Import Genius, Room.com.
  • ▶ 53:00 Ryan Petersen 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. 2 times in the scene
  • ▶ 54:22 Ryan Petersen And so finding people at Flexport who are focused on anything other than making Flexport successful at work, 3 times in the scene
  • ▶ 55:51 Ryan Petersen Flexport is struggling to get team members to come back to work right now. 3 times in the scene
  • ▶ 58:22 Ryan Petersen I think that works for a lot of companies, but as I was describing, that doesn't work in Flexport.
  • ▶ 1:00:27 Harry Stebbings Do you still see a Flexport? 5 times in the scene

Dave Clark: Lessons from Leading 1M Employees w/ Jeff Bezos at Amazon to CEO of Flexport | E1036 · 20VC with Harry Stebbings Jul 17, 2023 · 16 mentions

  • ▶ 17:58 Harry Stebbings You didn't need to, respectfully, like you had such a great career at Amazon, and then you come home and say to your wife, you know what, I'm gonna move after 23 years, and I'm gonna be CEO of Flexport. 2 times in the scene
  • ▶ 21:17 Harry Stebbings What did you learn at Amazon then that you've not taken to Flexport, and what did you learn at Amazon that you have taken to Flexport? 4 times in the scene
  • ▶ 25:14 Dave Clark Are making like Flexport right now is a very aggressive roadmap of products. 2 times in the scene
  • ▶ 32:26 Dave Clark Uh, but in fast growth environments, like I was at Amazon and like we're in it flexed work, uh, you often have to intersperse more senior external talent because the business, the people who grew up internally, they haven't, don't have… 3 times in the scene
  • ▶ 36:32 Dave Clark Company felt a lot like the culture of, um, Flex Fort. 2 times in the scene
  • ▶ 59:01 Harry Stebbings Dave, you can be CEO of any company other than Flexport for a day. 3 times in the scene

Shopify CEO Tobi Lütke: Remote Work vs In-Person; The Benefit of Setting Constraints | E997 · 20VC with Harry Stebbings Apr 3, 2023 · 2 mentions

  • ▶ 24:28 Harry Stebbings If you think about, say, um, I don't know, say, take COVID, and think about how shipping and delivery changes in the world of COVID, you have the ability now to call up Ryan at Flexport, or the CEO of UPS, or you name any of the big… 2 times in the scene

David Lieb: How I Founded Google Photos & Bump; Why I Left Google | 20VC #927 · 20VC with Harry Stebbings Sep 21, 2022 · 2 mentions

  • ▶ 59:52 David Lieb So like best example, my first angel investment ever, uh, was Flexport. 2 times in the scene

Wesley Chan: How I Created Google Analytics; The Founding Story of Gmail & Canva | 20VC #919 · 20VC with Harry Stebbings Aug 22, 2022 · 3 mentions

  • ▶ 5:50 Wesley Chan And, you know, I was, I was able to write the first check in the, you know, companies like Robinhood or, or Platt or, or Gusto or Flexport.
  • ▶ 11:13 Wesley Chan You know, Flexport didn't just start out as a import export piece of software and stop there. 2 times in the scene

Sheel Mohnot: Lessons from Investing in Flexport and Missing on Robinhood | 20VC #917 · 20VC with Harry Stebbings Aug 15, 2022 · 2 mentions

  • ▶ 29:20 Sheel Mohnot Personally, my biggest tip from a cashback perspective is Flexport.
  • ▶ 45:49 Sheel Mohnot Yeah, I think the most, um, the most compelling first pitch I had was Ryan Peterson at Flexport.

20 Product: Scott Belsky on How to Hire Your Product Leader and Team, 3 Questions All Great Product Leaders Ask, How To Structure and Run Effective Product Reviews & Is Product More Art or Science? Feb 9, 2022 · 1 mention

  • ▶ 0:56 Harry Stebbings Scott's also an early advisor and incredible investor in companies like Pinterest, Uber, Sweetgreen, Carter, Flexport, Airtable.

20VC: Why VCs Should Care More About Cost of Capital and Less About Ownership, Investing Lessons from working with Peter Thiel at Founders Fund, Why Liquidity Aligns Incentives Between Founders and Investors & Why It Is The Last Double That Matters in Ven Feb 4, 2021 · 2 mentions

20VC: Alexis Ohanian on Why Now Was The Right Time To Start Seven Seven Six, The 2 Very Distinct Types of Deals In Venture & The Unbundling of Social in 2021 Nov 19, 2020 · 1 mention

20VC: Biggest Lessons From Opendoor's Scaling Journey, How To Implement Systems for Growth & The Right Way To Structure Customer Discovery Processes with Julia DeWahl, Angel Investor Jul 3, 2020 · 1 mention

20VC: It's Time To Talk About Drinking; How To Stop, The Impact It Has, How Life Changes Post-Alcohol and The Biggest Misconceptions on Drinking with Ryan Petersen, Founder @ Flexport, Justin Kan, Founder @ Twitch, Matteo Franceschetti, Founder @ Eight Jun 1, 2020 · 2 mentions

20VC: Elad Gil on Startup Offense and Defence in a Recession, How The Venture Landscape Has Shifted & All Things Valuations, Secondaries and Layoffs May 26, 2020 · 1 mention

20VC: Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors Mar 9, 2020 · 1 mention

  • ▶ 0:32 Harry Stebbings As for founders, Matt's worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport, and many more incredible companies.

20VC: BoxGroup's David Tisch on Whether Concentrated Investing At Seed Works, Do Founders Really Want Direct Feedback and Is It Good For Them & Why Consumer Social Is Interesting Again Dec 2, 2019 · 1 mention

  • ▶ 0:28 Harry Stebbings One of the leading early stage firms in New York, with a portfolio that includes the likes of Flexport, Rig Up, Roe, Glossier, Clearbit, PillPack, and Plaid, just to name a few.

20VC Exclusive: Roy Bahat on Bloomberg Beta's New Fund, The Truth About Valuation That Very Few VCs Will Tell You & Why Founders of Venture Backed Startups Make The Best Angels Oct 18, 2019 · 9 mentions

  • ▶ 10:04 Roy Bahat So the first time we met Ryan Peterson from Flexport, I was at the time still the chairman of the company that I'd co-founded, which was a hardware company. 7 times in the scene
  • ▶ 11:08 Harry Stebbings And so I do have to touch on that because when it comes to kind of successful founders, you know, Ryan and Flexport are the poster children.
  • ▶ 32:57 Harry Stebbings And I think we're seeing this at Ryan at Flexport, this generation of really conscious leadership driven people who are fundamentally vulnerable, fundamentally willing to be open and actually present a much more human side of leadership…

20VC: Y Combinator's New President, Geoff Ralston on The Single Most Important Perspective An Investor Can Provide A Founder, The Biggest Lessons From Working Alongside Paul Graham & Why You Will Lose As An Investor If You "Profile Invest" May 27, 2019 · 1 mention

  • ▶ 0:26 Harry Stebbings Jeff Ralston, though, is the president now at Y Combinator, the world's leading accelerator with a portfolio that includes the likes of, check this out, Stripe, Airbnb, Dropbox, Coinbase, Instacart, DoorDash, Flexport, and so many more…

20VC: Carta Founder Henry Ward on Why The Best Companies Are Not Product Led But Distribution Led, 3 Requirements Needed For A New Market/Investment To Be Exciting and Why Small Markets Are So Attractive Apr 12, 2019 · 1 mention

  • ▶ 0:31 Harry Stebbings To date, Henry's raised over a hundred and forty seven million in funding from some of the very best in the business, including USV, Spark, K-Nine Ventures, and Meritech, and then also leading founders, including Flexport's Ryan Peterson,…

20VC: Initialized's Garry Tan on The Most Important Thing A Seed Investor Can Do For Founders, How Ownership Requirements Change With Evolution of Funds & Why There Is Not Too Much Capital Chasing Too Few Deals Apr 1, 2019 · 1 mention

  • ▶ 0:32 Harry Stebbings Now, Gary is the co-founder and managing partner at Initialize Capital, one of the leading West Coast early stage funds, with a portfolio including the likes of Coinbase, Instacart, Cruise, Flexport, and Opendoor, just to name a few.

20VC: What It Takes To Be The Most Effective Coach To Startup Founders, The Biggest Surprises and Challenges About Transitioning To Venture From Operations & 3 Trends Shaking The World of Consumer Today with Victoria Treyger, General Partner @ Felicis Ven Mar 11, 2019 · 1 mention

  • ▶ 0:28 Harry Stebbings 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.

20VC: Scott Belsky on Why We Must Challenge Our Faith In The Strength of Resources, Why We Must Rethink The Product Creation and Design Process & How To Determine Between The Good and The Truly Great When Assessing Individuals Jan 7, 2019 · 1 mention

20VC: Why Warm Intros Are Mostly Dumb, Why Ownership is Built On First Check and 4 Crucial Elements To Make Cold Inbound Attractive with Leo Polovets, General Partner @ Susa Ventures Nov 12, 2018 · 2 mentions

  • ▶ 0:33 Harry Stebbings Sousa, I really should not say this, but are one of my favorite seed funds in the valley, with a portfolio including the likes of, check this out, Flexport, Robinhood, LendUp, Cadium, Rigetti, the list really does go on.
  • ▶ 9:14 Harry Stebbings You know, with Sousa, you're an investor in the likes of Flexport, Robinhood, LendUp.

20VC: The Commonalities In The Makings Of Truly Great People, How Silicon Valley Will Become The Home For Crypto and Frontier Tech Once Again & Why Games Are Such A Good Tool To Understand Human Motivation with Daniel Gross, Founder & Pioneer, Head of AI Aug 27, 2018 · 1 mention

  • ▶ 0:41 Harry Stebbings And YC is obviously the world's most successful accelerator, with alumni that includes the likes of Airbnb, Dropbox, Reddit, Flexport, and many more incredible companies.

20VC: ClassPass CEO Fritz Lanman on Betting His Career Facebook Would Be A $10Bn Company, Lessons From Travis and Uber on Scaling A Global Marketplace & Whether Growth and Capital Efficiency Are Mutually Exclusive Jul 20, 2018 · 1 mention

  • ▶ 19:28 Harry Stebbings No, I couldn't agree with you more on logistics, and Ryan at Flexport from your portfolio is a personal favorite of mine, but I do want to discuss, you mentioned the angel investments there, and it's easy to look at your angel portfolio…

20VC: Sam Altman, Y Combinator President on What Makes Truly Great Leaders, Why We Will See A Compression of Seed Funding & The Future Scaling of YC Jan 17, 2018 · 3 mentions

20VC: YC's Daniel Gross on How YC Can Democratise AI & Reduce Incumbency Advantages, Why ML Enabled Software Will Eat The Software That Ate The World & Whether AI Will Produce Independent Companies or Be Technology within Incumbents Aug 21, 2017 · 1 mention

  • ▶ 0:16 Harry Stebbings For those that are unaware, Y Combinator is the world's most successful accelerator, with alumni that include the likes of Airbnb, Dropbox, Reddit, and Flexport, just to name a few of the incredible companies.

20VC: Investing; A Game Of Access Or Picking, Why Technical DD At Seed Is Irrelevant & Why A Contrarian Mindset Does Not Always Lead To Optimal Returns with Leo Polovets, Co-Founder & General Partner @ Susa Ventures Apr 19, 2017 · 3 mentions

  • ▶ 0:28 Harry Stebbings They've made investments in the likes of previous guests, Robin Hood, Flexport, Andela, LendUp, and Cadium, just to name a few future unicorns from their Stellar portfolio.
  • ▶ 20:46 Leo Polovets I think one of the ones that really stands out to me is we invested in a company called Flexport, which is, they basically help take the pain out of managing international shipping. 2 times in the scene

20VC: How Every VC Firm Is A Marketplace, Why A Large Amount of Promise in AI Today Is Impossible & Entrepreneurs 3 Main Pain Points of Fundraising with Alex Mittal, Founder & CEO @ Funders Club Mar 22, 2017 · 1 mention

  • ▶ 0:20 Harry Stebbings Their portfolio includes the likes of Slack, Greenhouse, Shippo, and Flexport, just to name a few.

20VC: Benchmark's Scott Belsky on What Makes Truly The Best VCs? Why Entrepreneurs Must Focus on 'The First Mile' & The Key Ingredients To The Perfect Onboarding Process Feb 27, 2017 · 1 mention

  • ▶ 0:39 Harry Stebbings He's now a venture partner at Benchmark, a venture capital firm based in San Francisco, and as an early stage investor himself, he's made investments in the likes of Uber, Warby Parker, Pinterest, and Flexport, just to name a few…

20VC: Garry Tan on The Biggest Takeaways From Advising 700 Companies @ Y Combinator & Why Now Is The Golden Age For The Early Stage? Dec 14, 2016 · 3 mentions

  • ▶ 0:29 Harry Stebbings Now, Gary's portfolio includes the likes of previous guests, Tilt, Eero, Flexport, LendUp, and many more incredible companies.
  • ▶ 10:08 Garry Tan And we see it with things like Flexport or one of our favorite companies is Bannerman. 2 times in the scene

20VC: Flexport's Ryan Petersen on Why Investor Relations Are Overrated, Why Boards Have To Be Rethought & Why MBAs Do Not Make Bad Entrepreneurs Dec 2, 2016 · 29 mentions

  • ▶ 0:29 Harry Stebbings Now, Ryan is the founder and CEO of Flexport, the freight forwarder for the internet age, and Flexport recently raised a phenomenal sixty-five million dollar Series B from the likes of Founders Fund, First Round, Felicis, Bloomberg Beta,… 3 times in the scene
  • ▶ 2:26 Harry Stebbings However, it's now time for me to shut up and hand over to the main man, Ryan Peterson, founder and CEO at Flexport.
  • ▶ 2:50 Harry Stebbings Now, I'd love to get started today by discussing a bit about you and how you came to found the incredibly hot Flexport and a quick bio of you. 4 times in the scene
  • ▶ 7:59 Ryan Petersen Like too many MBAs show up at Flexport and are like, yeah, I want to be on the executive committee. 3 times in the scene
  • ▶ 10:59 Ryan Petersen I've never had any trouble raising money for Flexport though.
  • ▶ 12:10 Ryan Petersen Uh, when you get to later stage, especially, so we just raised a few weeks ago, 10 times in the scene
  • ▶ 18:14 Ryan Petersen I don't think there's an investor who's like had this life changing life career or like company trajectory altering effect on Flexport, right? 2 times in the scene
  • ▶ 19:15 Ryan Petersen Yeah, I mean, you know, 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. 2 times in the scene
  • ▶ 22:35 Ryan Petersen Well, the Flexport blog, by the way, is my favorite blog, because I write most of the posts. 3 times in the scene

20VC: Why There Is A Revolution In VC, Why Boards Are Inherently Inefficient & Why Data Will Be Central To VC In The Future with Chris Farmer, General Partner @ SignalFire Nov 30, 2016 · 1 mention

  • ▶ 25:53 Harry Stebbings Thank you so much, as always, and we look very forward to bringing you Friday's episode with Ryan Peterson, founder and CEO at Flexport.

20VC: Felicis' Wesley Chan on The Rise of IoT, Getting Recruited by Larry Page & Creating Google's Biggest Success Disaster Jun 29, 2016 · 1 mention

20 VC 072: Super Angel, Fabrice Grinda: The Future of Startup Investing Sep 16, 2015 · 2 mentions

  • ▶ 28:34 Fabrice Grinda The company I recently invested that I really like is Flexport, which is an end-to-end, uh, uh, freight forwarding company. 2 times in the scene
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