Transcript
Founder Mode & Front Line Obsession - Ryan Petersen (CEO of Flexport)
From Ryan Hawk · Episode page · Watch on YouTube
· 1 h 1 min · 12,470 words · 136 timestamped sections
This is the full, timestamped transcript of "Founder Mode & Front Line Obsession - Ryan Petersen (CEO of Flexport)", an episode of Ryan Hawk published July 20, 2025 (1 h 1 min, about 12,470 words). It mentions 6 people, works and ideas, including Flexport, Ryan Peterson, Amazon, Renee Gerard, Luke Burgess.
What this episode is about
Ryan Petersen, CEO of Flexport, discusses innovative leadership through action-oriented problem-solving, exemplified by his viral "tweet storm" that highlighted the shipping crisis during COVID-19. Facing unprecedented congestion at US ports, he took decisive measures, including inspecting the Long Beach port to address inefficiencies, ultimately prompting significant policy changes and underscoring the importance of blending insights from various domains to drive impactful solutions.
Key takeaways
- Mixing domains can spark ideas that others overlook; innovation often lies in unexpected intersections.
- A taco truck and a boat led to a viral tweet; sometimes, unconventional approaches yield transformational insights.
- Bureaucratic bottlenecks can make or break efficiency; zoning laws might be the hidden villains in logistics.
- A viral tweet caught the governor's attention; it turns out social media can be a modern-day megaphone.
- Action-oriented leadership means diving deep; solving complex issues often requires more than just surface-level analysis.
Who speaks in this episode?
- Ryan Petersen (Guest) · 49 min speaking
- Ryan Hawk (Host) · 12 min speaking
What is discussed, and when
- – 10:00: Flexport
- – 20:00: Flexport, Ryan Peterson
- – 40:00: Flexport, Amazon
- – 50:00: Flexport
- – 1:00:00: Flexport, Renee Gerard, Luke Burgess, Columbia Business School
Notable quotes from "Founder Mode & Front Line Obsession - Ryan Petersen (CEO of Flexport)"
Flexport's a ultimately container shipping company help companies ship cargo around the world. They use technology to make that easier. And it was not easier. It was much harder than.
about Flexport · atIt off the next day. It went super viral at like I think I posted at 6 am the next day. Had Gavin Newsome call me by 10 a.m. The governor of California had you know written up…
about Ryan Peterson · atI'm a huge Amazon fan. I think Amazon's a really interesting company that the way and in our world of tech plus logistics there's not a lot. It's kind of an end of one type of company. Yeah,.
about Amazon · atYeah. Well, also the example of working hard is a really good thing. One more thing before we run. you're meeting with a young person, maybe like a newer employee who's…
about Columbia Business School · atThem those are all good ideas. And then I guess the other one comes from Renee Gerard which is the idea that we're all imitative people.
about Renee Gerard · atLuke Burgess has a book called Wanting which is all about Rene Gerard. So that's really good. It's funny Ryan actually I leave on this trip tomorrow.
about Luke Burgess · at
Who and what is mentioned in this episode?
People
- Ryan Peterson — Person · Main guest · 1 mention · first at
Primary interview subject; discusses Flexport leadership philosophy and his viral 2021 Long Beach port tweetstorm that helped trigger a rapid zoning change. - Renee Gerard — Person · Referenced thinker · 1 mention · first at
Cited for the idea of mimetic desire—humans imitate others—used as career advice about choosing role models intentionally. - Luke Burgess — Person · Referenced author · 1 mention · first at
Mentioned as the author of 'Wanting' (about René Girard), reinforcing the episode’s discussion of imitation, role models, and desire.
Companies & orgs
- Flexport — Company · Business focus · 15 mentions · first at
Primary company discussed by the CEO, focusing on logistics and global commerce - Amazon — Company · Referenced company · 3 mentions · first at
Mentioned as a comparison point for logistics and tech integration
Places & events
- Columbia Business School — Place · Referenced location · 1 mention · first at
Mentioned in the context of advice for young professionals
Full transcript with timestamps
be so good you can't be ignored. Whatever the thing is, most successful people have come from taking one domain and another domain and mixing these things out and find out like, oh, the best idea from this no one's even thought about over here, but it would work.
You are a actionoriented leader and what was called the tweet storm that saved Christmas.
We all remember there was like a 100 ships backed up off the port of Long Beach and all the ports in the US during COVID. The ports just were not able to keep up with all the demand. We needed to understand what was happening and was pretty dissatisfied with the answers that I was getting. And I tweeted about it the next morning. It went super viral. Had Gavin Newsome called me by 10:00 a.m. the governor of California. Written up in dozens of articles. It went very viral. And by 200 p.m. Okay. Uh I remember when this happened but I want to go deeper into the story because you are a actionoriented leader.
My favorite kind and that is in what was called the tweet storm when they were called that the tweet storm that saved Christmas. You where you famously rented a boat to inspect the Long Beach port in inefficiencies, right? And this prompted like this big policy change. Can you take me inside that story and what was happening and then what happened as a result of you taking action and making change?
So that was five years ago. So I had to jog my memory. Four years ago I think it was 2021. Um what happened? Well if we all remember there was like 100 ports backed up 100 ships backed up off the port of Long Beach and all the ports in the US during COVID. the ports just were not able to keep up with all the demand for products that people were buying when they were trapped in their house. And so you had it was obviously very impacting on Flexport's business. Flexport's a ultimately container shipping company help companies ship cargo around the world. They use technology to make that easier. And it was not easier. It was much harder than it had ever been to get cargo cleared.
So we we had real skin in the game. we needed to understand what was happening and was pretty dissatisfied with the answers that I was getting and we'd ask people what you know why is it the biggest problem was we couldn't get appointments to get a container picked up it was just taking forever to get containers out of the port and we asked kept asking different people and hearing different stories that didn't quite add up for me like people were saying the union's lazy and I'm like maybe, but are they lazier now than they used to be? I mean, like that's not an answer that I was accepting. So, it actually started with a joke where I said to my team, I was like, "Let's let's send a taco truck down to the union and then we'll give free tacos out and we'll just talk to all the union guys and see what they say, what the problem is." And I was joking, but then I decided I wasn't joking. And then no one knew if I was
joking or not. So, it took me like three or four different Flexport employees before I finally found someone who would like be like, "Oh, he's not joking. Okay, I will just go do that." Um, so that's where we started. We had a taco truck and our team went down. I wasn't able to go, but the team went down and they talked to all the union workers and the union workers uh at the port is long called the International Long Shore men's warehousing union. They told our team that um it was um because the again truckers are lazy. Truckers are missing their appointments.
And so when they had an appointment, 50% of all that you need an appointment to pick up the container and 50% of the time the trucker wouldn't show up. And so then they pulled this container to the front, no trucker shows up. Now the container that they pulled to the front is blocking all the other containers. You get this huge bottleneck and traffic jam. So from there, I was like, "All right, well, I got to go interview these truck drivers." And I have this the boat rental. You know, it's not that you can see the port that well from the from the water. You can't. I mean, it actually is a great thing to do in Long Beach if you're ever down there. It doesn't cost that much to get a boat to take you around and see the port from the sea, but you're not really going to understand what the problems are. What I did was invite the CEO of one of the biggest trucking companies in the LA area onto the boat with me. And it is a
great way to get information from somebody. You might try this, Ryan, for your podcast. You get them on a boat, they can't leave. They're stuck and you can just keep asking them questions forever unless they want to swim. And so we had the CEO of this trucking company on the boat and he's the one who told me what his view was was the reason that they couldn't get that the reason that the trucking companies were missing their appointments is that they couldn't get chassis. Chassis are the trailers that haul the containers around. And so if they were out of chassis and so you go five W's, you know, Toyota production system, you ask the five W's. What? Why can't you get chassis? Well, all the chassis have containers on them in our yard. And it's like, well, why don't you unload them? Well, the regulation says we can't stack containers more than two high in a trucking yard in Southern California. And it's like, well, okay,
why is that the rule? You know, we don't know, but that's the rule. That's what the zoning law says. So, because of that zoning law, then you couldn't uh stack once the containers got stacked too high in the yard, then the third container has to sit on a chassis and can't and then the chassis can't be used to go pick up more containers and you get it you get gridlock in the system. So, that's what I discovered on that day on the water and I tweeted about it the next morning. So, that was like one afternoon when we rented the boat. The next morning I took some time to think it over, wrote it up. Originally, it was like a blog post and I realized I'll just do this as a tweet storm. I blasted it off the next day. It went super viral at like I think I posted at 6 am the next day. Had Gavin Newsome call me by 10 a.m. The governor of California had you know written up in dozens of articles. It went very viral. I added
like 30,000 Twitter followers that day. And by 2:00 p.m., the city of Long Beach voted to change the zoning law in to allow stacking of containers up to four high in trucking yards, which anyone who's ever dealt with zoning law knows that this is kind of a remarkable feat of human achievement. I don't think any government's ever reacted that quickly to a citizen action in the history of government all the way back to, you know, several thousand years BC.
Yeah. The thing that's remarkable about the story though is your willingness to as the CEO, right, you're the founder CEO of the company to just do something about it, to take action, to get curious, to chase that down even though you didn't know the answers. There's uncertainty. You weren't sure if it was going to work. I I really want to get deeper into just your philosophy and your mentality as a leader to say, "Well, I'm going to do it. I'm just going to go do it." Right? instead of just sitting in the corner office, you go out and get taco trucks and rent a boat and get some other senior powerful person to ride the boat with you so you can talk to them and learn. Can you just talk through your your mindset and your process and philosophy when it comes to leading by action?
I mean, I don't I don't think that's something that's that unique to me. Hopefully, it's something that's imbued into all the flexboard people is biased to action and go do things. You know, find a got to go learn more. There's no way to better way to learn than to do or to see with your own eyes what's happening. Um, in to I'm a huge fan of the Toyota culture, Toyota production system. And in Toyota, they call it a gimba. Gamma walk. Uh, GMA is like the where the work gets done. In their case, it's a factory. And
what is that? Is that is that an acronym? It's a Japanese word. GMBA. Oh, okay.
It's like the place where the work is being done. Gotcha. The gimba. And so a gambo walk is walking around and you know you have to go and see what people are saying on the front line where the work's getting done. For our world it's harder because it's like we're very distributed. People aren't all in one location. Flexport has offices all over the We ship cargo to and from 147 countries. I went to 19 of them last year, but I'm not, you know, and when I'm on the plane, I'm not doing that. So it's a real tax on the ability to go out there.
So other people have to do it. Our whole team's doing this all the time. leaders got to walk the floor. Uh got to find out what's happening. And then you when you find out a problem, you have to solve it. And if you do, if you help the team solve their problem, they will then tell you about problems the next time you come around. And and that is key because leaders can easily get cut off from information if they're hanging out. You know, I'm in my office right now. It's a risk that I have is like having an office where I close the door and not being out there on the floor and hearing what people are saying and talking to them and solving their problems with them.
You probably don't have a a standard or typical day, but what what what in general does a day look like in the life of the CEO of Flexport?
Um yeah, well it depends on time of year. We have a real seasonable business. So there's a um there's kind of a heartbeat to the rhythm to the year. So um and what that means literally is like you have the Q4 is kind of peak shipping season, holiday season, etc. And so there it's a lot more operations, a lot of um high volume. It's making sure that we actually have space for all the cargo that's going on the ship so that our we're correctly staffed in the fulfillment centers and other operations. Q1 is the low season for shipping. It becomes the the in logistics world, that's when all the sales get done. Um so that Q1 is when I try to meet I met um 200 customers in person during Q1 and another hundred since then. So probably try to meet lots of customers. The only way to do that is scaled events. So I spent um two to three nights a week doing a customer event that try to do that throughout the
year but it's a little exhausting. So I'm taking a summer break from travel right now. I mean I just traveled uh to four countries last month. July and August to stay in San Francisco area. Um but uh so that's that's like those are the kind of the rhythms through the year is like very intense Q1 meeting customers going to conferences events lot a lot of um dinners and kind of speaking engagements those conferences those types of things in Q1 throughout the day you know we all I also manage a lot through we're we're a very document driven culture I I really like uh we're global which means we're yeah we're globally distributed which means it's really hard to get everybody body in a meeting at once. So we do a lot of written documents. Um so I do a lot of reading.
We do we have around 26 teams that do a monthly review with me. And so they write a six pager once a month about what they're doing, what they're what they got done, what they're going to do next month. Key metrics is page zero. And so I meet with the teams mostly in that structured environment, 26 of those every month. and then unstructured, lots of time to go figure out, okay, what's the key problem that we're focused on right now? And so I'll have two or three hours a day trying to solve problems. And often that involves sla spontaneous phone calls, slacks. You know, you work at flex, you expect to get a random unpredictable message from me asking for something, asking about something. So I probably, if you look at my Slack, I probably message with 30 to 40 people every day. Slack is like internal chat messaging different people all the time. And then yeah, lots of just like call people up, ask what's
going on, what's this or that thing that I'm trying to learn about. And then yeah, go walk the floor, go figure out, you know, a lot of travel to go figure out what's happening. Every time I go to an office, I feel like I get 10 pages worth of notes about again just like asking them about problems or opportunities or things that they you know that I didn't know and it's kind of sad honestly like it can't I can't go everywhere. So how are we going to get how do I get that information flowing everywhere? It can't be all about me. I think that's one of the things we're working on a lot is like how do we develop so that all the people all the leaders at flexboard know hey you get you're doing the same stuff as me more or less on a smaller scope a smaller area but go solve these problems directly you should be everyone at the flexboard should be obsessed with learning from the people on the front
lines from the customer ultimately I think Ryan a lot of people that are there aren't a lot of them that exist but if you're a CEO of a of a of a large company like you are who's highly competent who's on TV, who's being asked to go everywhere and do all this type of media, who's really well spoken. It can be intimidating and it can actually make you seem so powerful that you're not approachable. But I feel honestly the opposite with you. I feel like you have this high level of competence and power and you you literally make change happen in a day, but yet you still feel like this kind of downto- earthth, comfortable dude that I'm not intimidated to approach. And I don't really see that. I have a hard time finding people like that. Do you think about that? Is that intentional or is that just how you are? I'm curious what you think.
I don't know if I don't know if it's true. I mean, I think at Flexport, I'm sort of a at risk of being a celebrity that's unapproachable. So
really, but you're you're certainly certainly it's a risk. Uh you know, and most people don't people who know me know that that's not the case, but if you don't know me, I mean, I think that's a that's definitely a risk that I worry about. Like how do I make sure I don't get cut off from information flows and people are still
What do you do? How do you do that? I don't know. Try to be uh light-hearted and not You got to be humble. I think um recognizing that
this is not about me. This is about everybody is even really wise people are wrong like 30% of the time
probably at least. And so it's not enough to be wise. You also have to be humble and like accepting that you're often wrong and willing to change your mind quickly and change direction quickly and try things and find out, you know, and so um cuz it's very risky if people think that I said to do something, therefore everyone just has to go do it. And yet it's also super annoying when they don't do the things that you ask them to do if you're the boss. Uh the inherent like that's just messed up. Um, but it's the lack I trying to stay humble, I think, is really really important for any leader because of that fact. Like you're you're wrong a lot and it's okay to be wrong a lot. But you got to surround yourself with people who are keep willing to tell you when they think you're wrong and have some good debate and change your mind easily when when better information presents itself.
Who are those people for you? Is that like your exact team? Are they friends, family, all of the team? Yeah, for sure. Exact team, fans, uh my wife, my brother. Um but uh but I'd like it to be anybody at Flexport, right? Like I mean I'm learn from everybody in the company. I don't know nearly as much as our company as all the people do collectively. I'm lucky I have this privileged perch. I can get information from everybody. So I feel like I know as much as anybody, but not not more than everybody. That's for sure.
Gotcha. Paul Graham's one of my favorite writers and thinkers. I know he's a friend of yours, a backer. You guys have worked together for a while. You went through Y Combinator in 2014. And he he said, quote, "Ryan is what I call, and I love this, an armorpiercing shell. He's a founder who keeps going through obstacles that would make other people give up. But he's not just determined, he sees things other people don't see. The freight business is both huge and very backward." And yet, who of all the thousands of people starting startups noticed? Ryan Peterson. What does it mean to you to hear him say that?
Well, that's nice. I don't remember that exact quote, but um he's been a really good supporter for us for a long time. Really? Uh, even since I met him before I did Y Combinator, my brother did Y Combinator and they he knew him and we were renting a house in Palo Alto and we used to see Paul when he just had one son named uh his youngest or now his oldest rather um would be at the dog at the children's park and we were walking our dog all the time. So I would see him like multiple times a week and talk to him there
before I got into YC. I got lucky, made him love my brother was the reason it happened cuz my brother knew him. Yeah, great adviser. I think Paul's great in that he can uh only see the good and he doesn't really focus on the bad in people and companies. He's like what's the possible upside here?
Yeah, not really concerned with what an optimist. Yeah, definitely an optimist when it comes to startups. For sure.
Well, one of the things I mentioned about him is I he's one of my favorite writers and thinkers. I read everything that he publishes. he's published for a long time
and I think it kind of relates back to what you said earlier about how big your company is and how you guys need to write the six pagers to get very clear and then have those those meetings with you. How important is it
for you as well as the people on your team to be excellent writers, thinkers, communicators?
Um, yeah. I don't know. So I don't know how to say whether that's more important than other things. It's definitely one of the things that we look at in we try to do like a skills matrix of like here are the important attributes of people and where where do they assess themselves? How do we how does the manager assess them and communication ability is one of the 10 or 12 things on that list. But it'll depend on the role how important it is. I think one of our values is to simplify and that Paul's the best example of this as a writer. He's like incredibly smart and intellectual but very he uses very simple language. Uh he's he's passionate about using simple language as as a great writer should be. In fact, Paul considers his main life calling not to be starting Y Combinator, but to be an essaist.
And you know, he's really passionate about simple writing. And part of that value like comes from global logistics, really complicated. And so our ultimate mission is to make it easy. So easy there will be more trade. But so it is simplifying, right? We're trying to simplify this very complicated thing to make it simple, to make it easy. And yet the industry has this aura of complexity that makes it it allows for like mediocre people to hide because they maybe worked in this industry a decade. They learned all the buzzwords. They know all the things.
They know how the world works. They don't know why though. And they couldn't explain it in simple terms. And but when you if you don't know how it works at all and you're brand new and you hear someone explain all this, you're like, "Man, this person's a genius. I can't believe they know all this stuff." When actually they're just doing what what I call chauffeur knowledge, which is the knowledge your chauffeur gets from driving smart people around in the limousine. And they they can repeat what they heard, but they don't know any of the substance of why and first principles thinking, etc. So I think simplify if you can't simplify a problem to a point where layman can smart layman but layman nonetheless can understand it then you're probably operating it too much with chauffeur knowledge so on some level it's a test of that like I never have a hard time understanding Paul Graham or Mark Andreen Peter Teal these are some
of people that I've gotten to know who are really next level way way smarter than I am and like I don't have a hard time understanding them even though they're way smarter than me, right? And so it's kind of a a little bit of a test like if you can't communicate simply, there's probably because you don't understand the stuff well enough at a deep enough level. Yep. It's I think that's the ultimate sign of intelligence. One of them at least is taking the complex and making it simple. I think this is why why Tim Urban, for example, is is is such a a great writer and attractive to lots of people because he takes these super complex
like different areas of life and you read him and and he makes the reader feel smarter. I think great leaders do that. I think great that's part of our job as as leaders is to help simplify the the complex world. That's that's like your it's a big part of your job. I want to hit on something though that you just talked about is I love CEOs who are serious about values and you mentioned simplify being one of them. What are your other values and if you could I'd love to kind of like hear why the other ones are your values too.
Yeah. Um the the we have five values. There are sort of behaviors and they start with the first one which is empower your client and we this is it's all about our customers at the end of the day and this sounds a bit cliche but frankly in logistics it's kind of a mercenary industry where a lot of people are how much money can I make on this shipment there's a lot of intransparency a lot of mystery a lot of complicated stuff and like you can make where there's mystery there's margin you can make money off of that and you can extract as much money as you want on one shipment but the customer won't come back and like how do you build that long game motion. So that's that's number one. Playing the long game is is another one of our core values is recognizing there is so much short-term thinking in this industry. And those those values can come at odds with each other.
Actually, it's I don't know if it's by design, but it's certainly the way it works. Like empowering your client and playing the long game may be at odds. If what if the customer wants you to break the law and misdeclare something on customs or, you know, ship something that's hazardous? Like there's all kinds of ways that you could empower your client but actually not play the long game. And so there's there's an intentional tension that that comes with that. And and so what else can you say about that? It's it's you actually we have the values back here. I don't know if you can see that behind me. Yeah.
But acting like an entrepreneur is another one of the core ones. It's on purpose that says act like an entrepreneur. I don't think most people should be entrepreneurs. So it's like go imagine as if you owned this company. But it's about breaking down bureaucracy. say asking why over and over again challenging not saying the names of departments as a reason as a reason you could or couldn't do something
uh there's some bad habits that occurred at our company actually became a little bit bureaucratic and this is one to remind people like if you're shipping I don't want to hear about how origin like Asia this happened oh actually a great example for us is we ship a lot from Indonesia but we don't have any employees in Indonesia we work with the local partners are there. And what we found over and over again is that if we put our own people on the ground, even if they're overseeing that partner and managing quality and relationship and solving problems on the ground, quality goes up as measured by on-time performance cost quality, all the uh the the response times, all sorts of metrics that you could measure, quality goes up.
So I was like to the team, hey, why don't we have a office in Indonesia? And this is to my senior leadership team in Asia. called them out publicly. They were like, "Oh, illegal legal told us we can't." And I was like, "It's very odd to me that statement." So, I was like, "Well, who in the legal department?" You know, because I made it illegal now after that to to say that a department said something because it's like departments don't say anything. There was a human being in the legal department. Who was it? And no one knew.
And then I find out that I was like, "You need to find out and tell me tomorrow." Like, who said this? Like, I'm going to talk to them. I want to I'm not saying they're wrong. I want to know what they have to say. Well, it turned out it was a woman who hadn't worked in our company for two years.
You're like, "We're being haunted by the ghosts of former employees." And then when you talk to the legal team, I don't even believe she ever said that to be honest. Like when I cuz when I talked to the head of legal, he was like, "Oh, no. Legal would never say that. We that's not our job. We'll just tell you here the costs, here are the risks, like here are the challenges, but it's a business decision whether whether to go and do that." was what a great I won't call him out because he might have been said it in private but a great CEO told me um tell your people they don't have to listen illegal unless they tell you something is illegal otherwise they're just giving you business advice you know and uh
I like that I want to use that but uh so yeah don't mention you know no entrepreneur would ever be like oh the legal legal team says I can't do this it'd be like here show me the law like show me what is it about this that is illegal why can I not do this like ask more questions we can get the name of the person. So those are that that value comes from that simplify already mentioned how important that is to our business. But we build up this tendency. I think every company probably people show their expertise by using comp showing how complicated their world is. And
yep, you need me because look at all this complexity here. And if I can't understand some, I'm not the world's smartest person, but like logistics, we're kind of on some level like we're shipping cardboard boxes from here to here. And we're trying to create a more streamlined flow to eliminate defects and make it more reliable. When there's a problem, we need to root cause it and ask why five times and figure out, well, okay, is this how do we avoid this happening again in the future? None of this is that complicated. So, if it's getting to the place where I can't understand it, probably no. It's we're over complicating things. So, yeah, that simplified value score. And then teamwork, winning as a team. This is we're all on one team. feel like it can happen as your company gets big that people it starts to be about me versus other people or my team versus other teams and it's just like constant reminder guys
we're all on the same team here like we're just trying to help our customers solve these problems and go win we're not uh we're all we've got to align like we should
How hard is that one though Ryan because like you have 26 of those you have 26 different groups that are
and that's arbitrary there's probably more than that Well, yeah. I mean 26 just like having a meeting with you that they write up the six pager and then talk through it. So technically whoever's in charge of those 26 people if that's how it's organized that like because this is the thing that we actually run across when we do like leadership development work within companies is
is is someone will say like my team well that person does have a team within the larger team and then the CEO gets frustrated or the owner gets upset frustrated. It's like, "It's our team. It's our team." And the person's like, "It is, but I know I'm responsible for my team and I need to make sure my team's right. So, I keep my job. I get my bonus. I get my rate." You know what I'm saying? This is a very normal thing that happens. So, how do you especially that one? Because for you, you're the guy in charge of all of it. You, it is one team for you. But literally, it's not one team for anybody else in the company. How do you manage that? It's um it's got to come through the culture, through the vision, through the a commitment to the mission, to what we're trying to do, to alignment to a larger, higher set of goals, um through lots of teamwork. Mhm.
So like these meetings are not just with me like other execs are there and you know people are we're identifying who else needs to be here who everybody's reading all the 26 all these monthly business reviews and annual plans together aligning lot of work to map dependencies and say hey you own this and then constant constant assessment of like is this are these team teams aligned do they do we need and it it is true like if people will optimize for their own like change or or structure changes can make a big difference in achieving an outcome. We have the hardest there's a lot of global companies in the world.
There's a lot of complicated businesses and I don't think there's anyone that's more complicated than freight forwarding more interdependence because it's on a single you know there's a lot of global companies like Coca-Cola has probably more offices in more countries than we do. They're at every plate. But like Coca-Cola in Vietnam doesn't need to part cooperate with Coca-Cola in in Mexico. Like those are just they run their own little P&L. They just run fast. They do their own thing. But in in freight forwarding, every transaction from Vietnam to Mexico, both those teams have work to do that they need to collaborate on to get that shipment moved. And there's an ocean team that's getting it space on the boat. Customs teams clearing the customs. So there's domain expertise.
uh and there's regional operational work all needing to collaborate on each and every single transaction. So it's you do it a lot through metrics, a lot through alignment, a lot of video calls at different hours of the day. People know they got to work nights or early mornings and it's ongoing. But we we made it one of our values to just clarify like guys, we're all on one team here. Let's solve this problem together. A lot of it can be done through metrics. We never underestimate the incentives. You know, that's one of the core aspects here is you've got to have a strong mission that ties people together, a sense of purpose, a real focus that comes through the metrics, good decision- making processes if you need to change direction.
It's clear who can make what decisions, clear incentives, and a good program for knowledge and learning and make sure we're all like those are kind of the underpinnings of good culture in addition to the values.
It's a reminder of what my dad has reminded me a million times. It dude leadership if it were easy then you wouldn't need to exist. Like this is why you whenever like I complain about something this is why you exist as a leader. This is specifically why if it were easy and everything just worked, you wouldn't really need leaders. You just kind of go out and do the thing. But this is why leadership is a thing is because you have to work through these complexities, through these issues, through these incentives, through the messiness of human beings. That's that's why leaders exist.
Yeah. And the relationships really matter. Co really derailed Flexport in a lot of ways, not just the fact that we couldn't ship containers successfully because of the port situation and other problems. Um we it really we stayed to work from home and just for way too long now you know we're five days a week in office but we we stayed for like a couple years too long. We never should have we should have just always worked through it in office for our business and we then on top of that regardless of whether you're in office we're not all in the same office so you got to get people together. So started this on the recommendation of Brian Chesy, the CEO of Airbnb, who's someone I really look up to on the culture front. And he recommended, he got it from Steve Jobs, of take your take the 150 most important people in the company, not the most senior people, and it doesn't have to be the same list every time. It's not, but
get the top 150 together every twice a year is what they do. I think we're doing once a year for the top 150 and then twice a year in addition to that for uh 350 people. gather them together and go through here's what we're doing and why and here's all the different deep dive into the different teams and the different plans that are happening and trainings and part of that we do a speed dating thing just like everybody meeting every you know just like meet this person for 15 minutes talk through what do you do what they do just trying to create engineer serendipity on some level but get the teams I think that in person is just key I I'm jealous if companies were Just everybody works in one building.
Is it hard to choose those 150? Yeah, it is. The leaders have to pick their list and I reallocate and then I keep 25 slots that are just based on contribution to our culture and values, not based on level at all.
Yeah, the leaders will always pick their direct reports and the senior most people, but I don't want it to be the 150 most senior. So I do a lot of hand selecting of people who are like high contributing culturally as well as people who are just like all right this person maybe not the most senior but they're maybe it's a key designer or a staff engineer or a salesperson who's just absolutely crushing it or some you know you want to have a mix of different people there and it's not the same every time that has to be like this is not a static list if you're one of the flexorters who didn't get invited it's like it's fine you'll come to you know maybe you'll come to the next one or here's these avenues of like ways that you can contribute more to get invited did and it's not the only thing that we do. As we get more and more profitable, our goal is to end this year sustainably, durably profitable as a
company. Then big way to reinvest, I think, is going to be these types of summits and getting it's not cheap, right? We're doing the next one in Vietnam, taking 150 people to Vietnam. But I want to do more and more of that and different types of groups, right? We're doing the op summits. The summits we do were like 300 people where we're coming together. It's more operators, people who are like moving freight and stuff that we do in Vegas because it's cheaper. We do it in Vegas in the summer. Be nice to do that more frequently in more places like get people more exposure.
Yeah. I I feel like getting together with people there's just nothing beats that actually think it's in demand more now than ever because we got a feel we got a taste of what it's like to have that taken away from us. And so now I've sensed in-person events, companies getting together, leadership off sites, all of the above are way more in demand. I want to talk about culture and maybe even cost getting out of hand. So the last time we talked, you were the CEO, founder CEO of Flexport. Now we're talking you're the founder CEO of Flexport, but in between the two times we've talked, you were just the founder, but not necessarily the CEO. you hired a CEO to come in and run the business and there's a lot that goes into that. It didn't necessarily go great from what I gathered, but I I'd love to hear what made you initially want to hire an outside CEO and then what made you decide to say, "Nope, I'm taking this
thing back. I I gotta I got to come back and run the show." Yeah. It clearly didn't go well or you know, you don't hire the CEO and then plan to come back. Um,
right. And I came back after six months. So, it was a it was a pretty uh but a lot a lot went wrong during this that period. Why did we do it? I wasn't trying to hire CEO. I was trying to hire COO and met uh his D his name is Dave Clark. He was this he had become the CEO of Amazon's retail division. So, kind of what you and I think of Amazon, not AWS, but Amazon.com. He had but he'd really come up through the supply chain logistics group there. He ran supply chain and logistics. So, it seemed like an marriage made in heaven. I think I made the mistake of fall in love with the resume. But honestly, it's not Dave's D.
We We had our problems, but it wasn't I wouldn't blame Dave at all. It would be like it's even just listening to myself earlier talking about the culture and how complicated it is, how complex it is and how interrelated and it's just very hard for an outsider, probably impossible to take over the company. And if doing it over again, I mean, first of all, I wouldn't, but should have hired the COO if that's what I needed. And turns out I don't think I even needed that. I needed to have more confidence. But it takes years. I think you we're now like our key HR focus is just hiring from within.
You got to promote from within. And so if I ever someday I will pass the torch. You know, hopefully when I'm very old it will be someone who's been at the company for many years, who's grown up and it's a natural transition, not an outsider. It just doesn't it's just too hard to too much to learn. the fundamental problems, the short-term approximate cause. We let cost get out of control and quality suffer. Our customers, our churn went up, our NPS with our customers went down, and our cost ballooned. You're like, this is like a perfect storm. So, we we did have to go through quite a turnaround the last 18 months, but it's bad. Company's in a good place right now.
Did you like did you think you weren't like knowledgeable enough or like cuz like why bring in somebody else? I'm just trying to distinguish for for maybe someone listening who and I get the population isn't that big of someone who started something and then it gets so big or gets to the point where like you know what we need to bring the guy who ran like the best company in the world in Amazon. You know what I'm saying? Like I'm just wondering for that person.
I'm a huge Amazon fan. I think Amazon's a really interesting company that uh the way and and in our world of tech plus logistics there's not a lot. It's kind of an end of one type of company. Yeah,
maybe that's not quite true on a global basis, but in the United States, Amazon is like tech and logistics. That's what I think of besides Flexport. Um, and the the the problem that I was trying to solve is operationally doing the same thing over and over again a little bit better every time. How do you drive that operational rigor to improve quality defect to improve quality remove defects just like drive repeatability reduce variability of outcomes just that that whole um lean is what it's called in the US but it's Toyota production system ultimately is who pioneered this in the world and Amazon was very well known for doing that I had hired a lot of good people from Amazon a lot of them gave told me this guy was amazing would be perfect for us I trusted some people on the reference checks more than thing. Of course, I had some bad reference checks that I just ignored, so that was my fault. Um, but I don't want to go into
it too much when So, those were I was looking for someone who could do those types of things. Like, I'm more of a creative type. I like to do different things every day, not the same thing over and over again. And operations is the same thing over, you know, review the same metrics every day. Find the defects, root cause it, ask why over and over again, do it again. Kind of build those rhythms. And so I was looking for a partner to do that and next thing I knew I kind of convinced myself that he'd be better as the CEO rather than the COO and probably that was the only way to hire him in the first place. So kind of fell into that. That should have been the first sign that this was the wrong fit because it wasn't what I was hiring for. And hindsight should have had more confidence in my ability to go learn these things and put it in and get the team, you know, to own those challenges.
Oh, it's a fun intellectual problem and like philosophical problem and really it's actually very very interesting to take Toyota production system and apply it to our business because we're a different business. We're not a manufacturing business and yet there's a lot of parallels. So, it's actually very intellectually simulated to be like, well, what is the concept of inventory in a
logistics company? We don't have inventory, but what how would we what would be the related concept that we'd work off of?
Interesting. I want to talk about poise. I think excellent leaders have this. I've got to learn about being kind of calm and composed and poised as a quarterback and playing in college a little bit afterwards that, you know, stuff's going bad all the time. You throw an interception, you get sacked, you you got to bounce back. You got to stay cool. You got to get the play call in and call it with confidence. I I read that you said something. Rule number one in a crisis is everybody will rally around the calmst person in the room.
You got to have poise, right? You got to be composed. Can you talk to me about the importance of being the calmst person in the room?
Well, it's great advice. I'm not that good at it. Uh I'm kind of emotional and get pissed off too easily. It's something I need to work on, but it is intellectually correct and you need to remember it and come back to it and
figure out, you know, it's a real real crisis. Sure, you can you have the moment to digest, but when things are when people are just like disappointing you, sometimes it's sometimes valuable to get mad at someone and yell at them and get them, you know, you you don't do it. What what's the um a gentleman is never rude except on purpose. There's there's there is there is a time and place.
Do you do that in front of peers or do you do that privately or both? Probably both. Uh I don't know. Is that something you think about though or because some some exec teams that's just it's a it's just part of the like a sports background you just get used to that you're going to get ripped in front of all your buddies and that's just how it goes.
I don't think it's that bad. Yeah. I think you I think there's some value in I actually think there's some value in I don't do this that much but reading about it. It's kind of an interesting idea that there is value in getting mad at one of your directs in front of their team.
Yes. Because the next time that exec asks them to do something, they're like, "We better deliver or Ryan's going to yell at him again."
Well, sometimes I also I don't do that consciously, but I was just reading someone talking about that. I was like, "It's kind of an interesting idea."
I think though there's value if somebody is viewed as this is like a Bellichc Brady thing, but somebody is viewed as above everybody else of making sure that that you make sure that that's not true. I had a coach, I remember one of my favorite coaches, he he pulled me aside and said, you know, this is when things were going pretty well for me. And he said, "Hey, I'm going to rip you in front of the guys regularly because they need to see that nobody's above the team
and it and and so if you make a mistake, like I'm I might overdo it a little bit." And and actually that built a ton of trust with me and him because he he like told me he's like, "It's not going to be fake. It'll be when you mess up, but but just know and I know you can take And so I think there is some some art to that when it comes to communicating and leadership to making sure that everybody knows the standard here is really really high and we're holding everybody to it. I think that's a good leadership moment.
Yeah, that's interesting. There's so much I never played. I wasn't a very good athlete so I don't have like uh that background but I wish
where do you pull like your leadership lessons and and I feel like you're well read but where do you pull from? Is it from your peer group, your friends, the Paul Grahams of the world? like where do you do it?
Some of that I have a good CEO group that like 10 eight or there's 10 of us I think CEOs of kind of peer level companies that we meet really regularly and and give each other feedback and
how was that how was that formed? One of them I don't know they already had it going and they invited me.
Well I'm I'm fascinated by these things because I think we need these things like all of us need these. So, I am curious like there's probably some parts that you don't talk about, but but I am just curious about how the whole thing goes. What are the meetings? Are they formal, informal? Like what is how does that semiformal? There's formal in terms of like we have it prescheduled. Not you're only allowed to miss two a year or you get kicked out.
Wow. You go you get together in person every other month in person. Wow. Are they are you are you guys located like all in California or
Everyone's in California, but some are in SoCal and some are in SF. So that's why we don't do every month in person.
Okay. Um but we'll we'll and then we alternate SF or LA. So you have to fly every third month to the other country or to the other city. And then um we do updates. So you say what's the best thing that's happening the last month and the worst thing kind of personal and professional. Share if and then someone kind of times it. Make sure people don't go for too long. And then we saved time at the end to synthesize topics that looked relevant across different people's areas and deep dive or offer to help somebody who had a problem that someone thinks they could offer input on. And
so it's pretty good. I think I recommend people you got to find peers that can do that for you,
right? Um what uh it's similar I think that we're not in like a formal association with a bigger group, but I think it's kind of similar to what YPO does.
Yeah. In their little formations. I think we probably copied it. I think one of the guys a member of YPO and helped us structure a little bit on how they do things.
You have simplified your Twitter bio or X bio about making global commerce as simple and reliable as flipping a light switch and you highlighted this recently. Can you talk to me more about simplicity and the kind of we all can envision just flipping a light switch? What's that all about?
The light switch. I I like the light switch analogy because very similar in the old days when the electricity was first invented, every company had to have their own power plant in their factory. Everybody generated well originally before electricity, you had to put your plant next to a waterfall to make a to make power off the water mill. But then when it when electricity came along, everybody ran their own generators. And it was only with the development of the grid that you could then just take it. Now we just take for granted that you have electricity. You flip that light switch.
But when you control if you're in a place that's coal fired where you're getting your power from coal, which most of us are, if you flip that light switch, you're actually controlling the power plant itself. Like it's getting a little bit hotter for you. There's not a battery between you and the generator. It's generating a tiny bit more electricity on demand for you. That is a that we want. We just totally take that for granted and yet it powers everything that we do. And I think in logistics like in commerce you have this mindset.
You don't really think about it but you the idea you you buy something on a website and it just gets delivered to you. You think therefore oh there must be this complex interconnected system that flows data back to the factory that's making those goods and they produce one more on demand to to replenish and move it in. And that's that's not how it works today. today it's like a bunch of emails and attachments and kind of duct taping this thing together of phone calls and spreadsheets and stuff and so we but that's what our ambition is is to make it work a lot more like the electrical grid that you buy something the demand signal is automatically sent back to the factory to queue up production on demand make one more or maybe they shouldn't make one more. It depends on the product and what the machine learning models say about what demand forecast looks like for the next one and where to position
that item. Should they put it in a fulfillment center near you or in the center of the country or fulfill it off the water, fulfill it directly from the factory? Um, yeah, we want to make it more like the electrical grid where you can just take it for granted and uh have it work on demand.
Interesting. I I like the simplicity and the use of metaphors and making something complex easy to understand. Changing gears a little bit before we before we run in a few minutes though. I'm always fascinated what a CEO looks for in somebody specifically on a leadership team. So these are really important decisions. I know it sounds like you're shifting more towards promoting from within and maybe you've always done that for other jobs but you didn't for the one brief stint as for the CEO, but what do you like what are some of the musthaves when someone's going to get promoted or hired into a role that's super important, a leadership role? A number of things.
Work ethic very underrated, but like you and you won't find that in an interview. You got to talk to people who worked with them. Is this one of the hardest working people you've ever met? Will they outwork everybody else? Work ethic is super key. I think John Calvin is probably the greatest religious genius of all time. Well, maybe that's an overstatement, but incredible genius because Calvinism basically said your fate is predetermined whether you're going to go to heaven or hell is already decided before you're born. You have nothing to do. However, the only way you can know which one you're going to do is based on how much wealth you acrew and how hard you work. It's like basically the origin of capitalism comes from that in insight. It's like, all right, I got to work really hard and don't spend money so that I can prove that I'm going to heaven. I'm not like literally looking for Calvinist Protestants, but there's
something to that work ethic. It's not it's not in aid in everybody. Some people have it, some people don't. You can be any religion to have it. There's some there's some argument that the origin of it comes from Calvinism. Intellect. I want really really smart people. I want to be wowed by how smart they are. And that comes with curiosity because you're you don't become that smart. You're not born that smart. You learned all this stuff. And so someone who's like constantly learning and excited by learning. Then I mentioned earlier humility because again even the really wise people are wrong 30% of the time. So you got to be willing to be wrong and admit it and stay humble and and frankly like arrogance is its own form of stupidity because you stop learning.
Reliability something that you want to look for someone that actually does what they say they're going to do. public speaking or charisma. I mean, I guess that goes along with communication that we talked about earlier, your ability to simplify and communicate well. And then there's in our space is domain experience, which could be logistics, could be technical, legal, finance, whatever the domain is that they got to be have seen a lot of a lot of edge cases and have good developed enough experience, have intuition. How much of this is done through an interview process versus how much is done through referrals and talking to people who've worked with them?
It's almost all referrals and references. And that's why I try to do internal hiring for everything because it's like how do you trust these external people that they're telling you? Do you know them better than they know the person like
Yeah. Um you could so you have you could see it that they've actually done it while working at your company sal worked really really hard been humble curious learned
but uh but this you can't we can't fill all the roles internally we try so hard but um when it's external I try to get someone who's referrals from people who work at the company worth way more than a random reference check that the candidate themselves gave you right
right that's my ideal like I've only hired one exec in the last couple years and he was someone who was one of my direct reports bosses for six years and said he was the best boss ever without remembering that he works for me now. So
are you still doing much work with Founders Fund? Not that well I mean I was full-time there and now I'm kind of a part not really I'm so focused on Flexport. I hope to in the future but gota get the end of the year we turn profitable Q4 and then I think I'll have more options there. I don't think most people in your position, they have moments of where there's more balance in their life, but a lot of their life is not very balanced. So, I don't really even strive for that. I think people that do big things usually are obsessed. They have amazing work ethics. They get after it, right? They chase it with great rigor. I am curious, though, you're a family guy, married, kids. How do you manage making sure that you have a strong marriage and you're a good dad in addition to doing this impossibly hard job?
Yeah, I got two little kids, two little girls. So, I'm try to give them as much attention as I possibly can when I'm there. Make it home for bedtime most nights, weekends, a lot of time, but I'm kind of bad. I'm I'm like constantly thinking about Flexport. So,
really? Yeah. Constantly. Like, I'm sure investors love to hear that and employees probably love to hear that, but what does your wife think when you say that? Um, well, I mean, I'm just being honest. She knows, she's correcting me. She's pushing me. She's a good partner. She like knows, you know, what's best for me, what's good for the company. She knows, she knows that it's good that I'm obsessed with Flexport. It's like Hannibal, right? Like Hannibal the general. He was always praised because his soldiers were never loy were never defected. They were always very loyal and he was like, "Ah, he's a great general."
But the only thing is he was pretty cruel. Whenever somebody defected from his army, he would torture them to death. Like, well, you can't criticize him for that. If you're going to praise him for his soldiers never defecting on some level, it's like take you got to take the good with the bad. So,
so are you saying though, because I I I feel this so much of when you're kind of an alpha type of a person who gets things done, who does big big things in the world, who leaves a positive dent, right? you employ thousands of people, you're helping so many your customers, all this. There is a cost, right? You don't become that type of a guy who does those things without being obsessed, without being a maniac, without working really hard. I think there's just a price to it. And I don't think we should act like that doesn't exist. That's just a real thing.
Totally. That's my thing. But I mean, like, it's it's amazing to have kids because it gives you instant fulfillment, sense of purpose why we're here. I mean, I would always wonder about that. Like I always got my purpose and fulfillment from building Flexport and I would wonder like what are all these people that aren't doing this get how are they getting purpose in the world and then you like have kids you're like oh I get it. You just need to like you just need to raise your kids and that's all the purpose you ever need. Um so there's a tension there because I see it. I feel it. It's great to care about so much about them about anybody besides yourself.
That's the thing I feel like it gives us massive purpose. I remember after having one and I was thinking there is no possible way I can love the second one as much as the first one. It's not possible. But here's the weird thing and you know this right because you've done it. But then you have the second one and and and all of a sudden
you can like you do like you you actually are able to have more love. And I think that's a good thing for a leader. That's a good thing for a person is like,
I didn't think it was humanly possible cuz I love this thing so much. And then you have the second one, you're like, wait a second, I I'm capable. It's just it's bizarre, dude. I mean, being a dad is the best. Being a dad's best
the best. It is the best. Something I work on constantly is like, work on my put my phone away. Stop. Don't let it Don't pick it up. Don't get distracted. It'll be there.
Yeah. Well, also the example of working hard is a really really good thing. One more thing before we run. you're meeting with a young person, maybe like a newer employee who's straight out of college or straight out of Columbia Business School like you were, and they want to leave a a dent, right? Like they want to leave a positive dent in the world. What are some general pieces of life/career advice you give to them?
Oh, I mean, I think everything is about learning is like building your capabilities and learning and um I I really like to point people to Charlie Mer's essay on worldly wisdom. You can find it. I think it was actually a graduation speech that he did. I
think it was at USC. Yeah. Yeah. Yeah. That's a really important piece of knowledge and wisdom is is the idea that you summarize it is that in life there's only a limited number of domains of areas that it's not infinite things. There's yeah these are arbitrary lines between those. You can say how many there are but I you know call it 300 different areas. And in each of these domains there's two or three big ideas that if you understand that you kind of get 80% of the whole domain. And so it's not an infinite problem to learn to become worldly wise would mean you know these kind of main ideas and therefore mental models from all the domains. And that's a very good starting point to strive towards in w in life.
And the you know you can read pretty easily the world's smartest people have taken the moment taken the time to write down their ideas like you can engage with the smartest people to ever live and a lot of people don't take advantage of that. So going to read constantly find find the people who know the thing that you want to do and model them ask them those are all good ideas. And then I guess the other one comes from Renee Gerard which is the idea that we're all imitative people. There's no way around it. That's what human beings are. We imitate others.
That's what separates us from the animals is that we're very good at imitating. And there's no way out of this. You're going to imitate somebody. So, you should be very conscious about who you imitate.
Choose your role models wisely. Surround yourself with people that are working on have similar values to the ones you want to have that are working towards inspiring things that you know that that that are leading the type of life that you want to lead because you're going to naturally imitate those people. And if you're not careful, you'll be imitating the wrong model. You will be you will imitate someone. This is why um why Christianity can be really important is like imitate Christ even if you know you pick the ideal and imitate that rather than at least you're consciously choosing someone great to imitate and otherwise you will imitate someone who's you get it wrong and it could be disastrous. So I think picking really good role models, whoever it might be, is really important and do it consciously.
Those are all good ideas and optimize for that for learning and like who are you going to learn from and you don't have to have one role model. You can have role models for different areas of development or different areas you're trying to trying to learn.
Luke Burgess has a book called Wanting which is all about Rene Gerard. So that's really good. It's funny Ryan actually I leave on this trip tomorrow. I go on an annual trip with my younger brother and it's it's with people who have definitely sustained excellence. They've generated a lot of wealth in their life. Not they haven't inherited. These are people who have worked really really hard and made tons of money and and are kind of world changers. And I'm super lucky to get to go. We've done it the last 17 years. When I come back from that trip, we have dinners every night.
We hang out during the day. When I come back from that trip, I I think differently, man. being around kind of world
dominators, it it raises your level of thinking. It it truly truly does. And like I so I I I love that advice to put yourself in environments with people who do big things, who get after it, who are optimist, who want to do it the right way by working insanely hard, like the first thing you mentioned when you're going to hire somebody. That's so good. Dude, I love this.
And remembering that success compounds, right? because those people don't want to hang out with you if you've never done anything interesting or haven't contributed etc. And so you got to work your way up and then the more successful you become the more capable you become it'll compound on itself because now you're going to be able to surround yourself with people even more successful than that and yes
that will inspire you that you will learn from them etc. you know, you don't networking is not that useful. Like you come out of college and like, oh, I met so and so. Like I met I've met tons of entrep famous people and entrepreneurs, but like doesn't really help me unless they're see me as a peer and want to engage with me and develop. And that, you know, I've earned over time by being more and more successful. So, you got to work on yourself. And
the the best networking tool is being insanely good at whatever the thing is that you do.
Yeah. the best network. I It really is like be so good you can't be ignored. The Steve Martin Cal Newport stuff, right? Whatever the thing is, it doesn't necessarily matter, but be insanely good at what you're doing. That's how you don't get kicked out of groups like that because that, you know, those groups are ruthless, too. Like they will they're not afraid to disinvite people, right? Like you're just out. So, I think like that's a big part of it as well. And in business world, you know, coming back to that mental models thing of like learning all this stuff, like a lot of the success, the most successful people have come from like taking one domain and another domain and mixing these things out and find out like, oh, the best idea from this no one's even thought about over here, but it would work. I mean, in our case, like SAS and one of my early inspirations for Flexport was this web app called Dropio.
Sam Lesson started it, who then went over to become, I don't know, senior job at Facebook. Facebook acquired it and killed it. There's one of the team, but it was like the earliest web app where you could just like upload docs. Now you take it for granted, Google Drive or something. You upload these docs in there and it had a really nice UX. I was like, "Oh, we should have this for customs." I know Sam. I don't know if I've ever told him that he was really an inspiration for customs for flexport in the early days because I'm like but it was taking like all right what's cutting edge web ideas and applying it to this other domain that no one inside of that domain was thinking about this and now it's probably what what can you take AI and apply it to these other domains and generate useful insights and but if the more different mental models you have the more areas also the more interesting
you're going to be the more life will be curious like I'm always a little jealous of geologists Because wherever they go, there's something interesting to look at. There's rocks everywhere. It's like no matter where a geologist goes, like the world's full of wonder. I look at rocks, I'm like, whatever. It's a rock.
Yeah. So cool. It's funny you mentioned Sam. He's coming on in three weeks. I think we just booked that one a couple weeks ago. Fascinating, dude. Hey, man. I love this. I'd love to continue uh and do it again as a little bit more time passes. Just just to to to hear from you, man. I always learn learn a ton. I appreciate it, man.
Likewise, man. Thanks a lot. Awesome. Thanks, man. See you, Ron. All right.
Questions about this episode
Who speaks in "Founder Mode & Front Line Obsession - Ryan Petersen (CEO of Flexport)"?
Ryan Petersen (Guest), Ryan Hawk (Host).
What is "Founder Mode & Front Line Obsession - Ryan Petersen (CEO of Flexport)" about?
Ryan Petersen, CEO of Flexport, discusses innovative leadership through action-oriented problem-solving, exemplified by his viral "tweet storm" that highlighted the shipping crisis during COVID-19. Facing unprecedented congestion at US ports, he took decisive measures, including inspecting the Long Beach port to address inefficiencies, ultimately prompting significant policy changes and…
What is mentioned in this Ryan Hawk episode?
6 people, works and ideas are mentioned, including Flexport, Ryan Peterson, Amazon, Renee Gerard, Luke Burgess, Columbia Business School. Each one on this page links to its own page with every episode that mentions it.
How long is "Founder Mode & Front Line Obsession - Ryan Petersen (CEO of Flexport)"?
The episode runs 1 h 1 min; the transcript is about 12,470 words in 136 timestamped sections.
More from Ryan Hawk
About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.