645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity

20 Jul 2025 · 58 min

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Podcast Summary: The Learning Leader Show With Ryan Hawk - Episode 645: Ryan Petersen (Flexport CEO)

Overview In this episode, Ryan Hawk interviews Ryan Petersen, the founder and CEO of Flexport, a technology-driven global logistics company. Petersen discusses his experiences in leadership, the challenges of supply chain management, and his philosophy on decision making and company culture.

Key Themes and Discussions

  1. The Tweetstorm That Saved Christmas
  2. Background: During the 2021 supply chain crisis, Petersen rented a boat, brought tacos, and invited a CEO of a major trucking company to inspect the Port of Long Beach.
  3. Outcome: His viral Twitter thread prompted immediate action, leading to a change in policy by California Governor Gavin Newsom. This illustrates the impact of direct action and problem-solving in leadership.
  1. Frontline Obsession & Gemba Walks
  2. Gemba Walk: Petersen emphasizes the importance of being present on the frontlines by traveling to meet employees and customers. He believes that understanding the challenges faced on the ground is crucial for effective leadership.
  1. Leadership Style at Flexport
  2. Communication and Documentation: Petersen implements a culture of "managing through writing," where teams produce six-page memos monthly, fostering deep discussions.
  3. Daily Engagement: He connects with 30-40 employees daily to maintain communication and gather insights.
  1. Leadership & Decision-Making Criteria

Petersen discusses his criteria for hiring leaders, which includes:

  • Relentless Work Ethic
  • Intellectual Curiosity
  • Humility: Acknowledging that even wise individuals can be wrong.
  • Reliability
  • Charisma
  1. Lessons from Mentors
  2. Petersen shares valuable advice he received from influential figures like Paul Graham (Y Combinator) and Brian Chesky (Airbnb) emphasizing the importance of in-person gatherings for innovation and alignment.
  1. Challenges and Mistakes
  2. Petersen candidly reflects on a difficult CEO transition when hiring Dave Clark from Amazon, recognizing the complexities of leadership and the necessity of promoting from within.
  1. Personal Growth & Philosophy
  2. Inspired by thinkers like Charlie Munger and René Girard, Petersen advocates for lifelong learning, urging individuals to read widely and choose role models wisely.
  3. Key Quote: "We're all imitative people. Choose your role models wisely."
  1. The Importance of Simplicity in Leadership
  2. Petersen emphasizes that the logistics industry often complicates issues unnecessarily. He aims to make global trade as simple and reliable as flipping a light switch, emphasizing the need for clarity and simplicity in operations.
  1. Flexport’s Core Values

Petersen outlines five core values that guide Flexport

  • Empower Clients
  • Play the Long Game
  • Act Like an Entrepreneur
  • Commit to the Vision
  • Simplify
  1. The Role of Poise in Leadership
  2. Petersen highlights the importance of staying calm during crises, stating that "everybody will rally around the calmest person in the room."

Key Takeaways

  • Action-Oriented Leadership: Taking initiative can lead to significant change.
  • Frontline Engagement: Understanding the challenges of employees is essential for leaders.
  • Continuous Learning: Emphasizing lifelong learning can enhance leadership capabilities.
  • Simplicity is Key: Striving for simplicity can improve operations and customer relations.
  • Core Values: Establishing and adhering to core values can align teams and improve company culture.

Conclusion Ryan Petersen's insights provide a powerful perspective on leadership in the logistics industry and the importance of effective communication, frontline engagement, and a commitment to simplicity. His experiences and philosophies offer valuable lessons for aspiring leaders across various fields.

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Transcript

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0:00This episode is brought to you by my friends at Insight Global. Insight Global is a staffing and professional services company dedicated to being the light to the world around them. If you need to hire one person, hire a team of people, or transform your business through talent or technical services, Insight Global's team of 30 ,000 people around the world have the hustle and grit to deliver. Hiring can be tough, but hiring the right person can be magic. Visit insightglobal.com slash learning leader today to learn more. That's insightglobal.com slash learningleader. Welcome to the Learning Leader Show.

0:50I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcasts. Go to learningleader.com. Now on to tonight's featured leader. Ryan Peterson is the founder and CEO of Flexport. He's built a reputation as one of the most forward-looking problem solvers in business today, known for taking on massive complex challenges in supply chains and logistics. He started Flexport in 2013 after seeing firsthand how broken and inefficient global shipping really was. And under his leadership, Flexport has grown into a multi-billion dollar company, moving goods for some of the biggest brands in the world.

1:40During our conversation, we discuss how he's become a sought after thinker on everything from globalization to entrepreneurship to tackling bottlenecks. And he's even known for literally renting a boat to help unclog the port of Oakland. Amazing story there. And Paul Graham has said, quote, Ryan is an armor-piercing shell, a founder who keeps going through obstacles that would make other people give up. I think you're going to love this one. Ladies and gentlemen, please enjoy my conversation with Ryan Peterson. Okay, I remember when this happened, but I want to go deeper into the story because you are an action-oriented leader, my favorite kind.

2:32And that is, and what was called the tweet storm when they were called that, the tweet storm that saved Christmas, where you famously rented a boat to inspect the Long Beach port 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. I had to jog my memory. Oh, four years ago. I think it was 2021. We all remember there was like 100 ships backed up off the port of Long Beach and all the ports in the U.S. 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.

3:14It was obviously very impacting on Flexport's business. Flexport's ultimately a container shipping company. We 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 had real skin in the game. We needed to understand what was happening. and was pretty dissatisfied with the answers that I was getting. 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 kept asking different people and hearing different stories that didn't quite add up for me.

3:47Like 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 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 be like, oh, he's not joking.

4:19Okay, I will just go do that. 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, they told our team that it was because, 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've 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.

4:52You get this huge bottleneck in traffic jam. So from there, I was like, all right, well, I got to go interview these truck drivers. And the boat rental, you know, it's not that you can see the port that well 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's a great way to get information from somebody.

5:20You 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 that told me what his view was. 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 Ys, Toyota production system, you asked the five whys. Why can't you get chassis? Well, all the chassis have containers on them in our yard.

6:01And it's like, well, why don't you unload them? Well, the regulation says we can't stack containers more than too high in a trucking yard in Southern California. And I was like, well, okay, why is that the rule? We don't know, but that's the rule. That's what the zoning law says. So because of that zoning law, Once the containers got stacked too high in the yard, then the third container has to sit on a chassis. And then the chassis can't be used to go pick up more containers and 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.

6:37So 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. I think I posted at 6 a.m. the next day, had Gavin Newsom call me by 10 a.m., the governor of California, written up in dozens of articles and went very viral. I added like 30 ,000 Twitter followers that day. By 2 p.m., the city of Long Beach voted to change the zoning law to allow a 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.

7:16I don't think any government's ever reacted that quickly to a citizen action in the history of government all the way back to several thousand years BC. 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 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.

7:55Instead 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 mindset and your process and philosophy when it comes to leading by action? I don't think that's something that's that unique to me hopefully it's something that's uh imbued into all the flex sport people is biased action and go do things got to go learn more there's no better way to learn than to do or to see with your own eyes what's happening i'm a huge fan of the toyota culture toyota production system and in toyota they call it gemba walk gemba is where the work gets done in their case it's a factory what is that is that is that an acronym it's a japanese word gemba oh okay and so a gemba 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.

8:46People aren't all in one location. Flexport has offices all over. We ship cargo to and from 147 countries. I went to 19 of them last year. 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, got to find out what's happening. And then 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. That is key because leaders can easily get cut off from information if they're hanging out.

9:22I'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 standard or typical day, but what in general does a day look like in the life of the CEO of Flexport? Yeah, well, it depends on time of year. We have a real seasonable business. So there's a, there's kind of a heartbeat to the rhythm to the year. And what that means literally is you have Q4 is kind of peak shipping season, holiday season, et cetera.

9:53And so there it's a lot more operations, a lot of high volume. It's making sure that we actually have space for all the cargo that's going on the ship so that we're correctly staffed in the fulfillment centers and other operations. Q1 is the low season for shipping. It becomes in logistics world, that's when all the sales get done. I met 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 two to three nights a week doing a customer event. Try to do that throughout the year, but it's a little exhausting.

10:26So I'm taking a summer break from travel right now. I mean, I just traveled to four countries last month, so July and August on this day in San Francisco area. Those are the kind of the rhythms through the year is like very intense Q1, meeting customers, going to conferences, events, a lot of dinners and kind of speaking engagements, conferences, those types of things in Q1. Throughout the day, we're a very document driven culture. We're globally distributed, which means it's really hard to get everybody in a meeting at once. So we do a lot of written documents. So I do a lot of reading. We have around 26 teams that do a monthly review with me.

11:06And so they write a six-pager once a month about what they're doing, what they got done, what they're going to do next month. Key metrics is page zero. 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 spontaneous phone calls, Slack. You know, you work at Flexport, you expect to get a random unpredictable message from me asking for something, asking about something.

11:40So I probably, if you look at my Slack, I probably message with 30 to 40 people every day, different people all the time. And then, yeah, lots of just like call people up, ask what's going on with 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. Again, just like asking them about problems or opportunities or things that I didn't know. And it's kind of sad, honestly. Like, I can't go everywhere. So how do I get that information flowing everywhere?

12:16It 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 Flexport know, hey, you're doing the same stuff as me, more or less on a smaller scope, a smaller area, but go solve these problems directly. Everyone at the Flexport should be obsessed with learning from the people on the front lines and from the customer, ultimately. I think, Ryan, a lot of people, there aren't a lot of them that exist, but if you're a CEO 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.

12:57But I feel honestly the opposite with you. I feel like you have this high level of competence and power and you literally make change happen in a day, but yet you still feel like this kind of down to earth, comfortable dude that I'm not intimidated to approach. 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 about that i don't know if it's true i mean i think at fly sport i'm sort of a at risk of being a celebrity that's unapproachable so really it's 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 you got to be humble.

13:47I think 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. Because 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. That's just messed up. Trying to stay humble I think is really, really important for any leader because of that fact.

14:27Like you're wrong a lot. And it's okay to be wrong a lot. But you got to surround yourself with people who are willing to tell you when they think you're wrong and have some good debate and change your mind easily when better information presents itself. Who are those people for you? Is that like your exec team? Are they friends, family, all of the exec team? Yeah, for sure. Exec team, friends, my wife, my brother, but I'd like it to be anybody at Flexport, right? Like, I mean, I'm learning from everybody in the company. I don't know nearly as much as our company as all the people do collectively.

15:04I'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 more than everybody. That's for sure. Got you. Paul Graham is 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 said, quote, Ryan is what I call, and I love this, an armor piercing 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.

15:40And yet who of all the thousands of people starting startups noticed? Ryan Peterson. What does it mean to you to hear him say that? That's nice. I don't remember that exact quote, but he's been a really good supporter for us for a long time. I met him before I did Y Combinator. My brother did Y Combinator and he knew him. And we were renting a house in Palo Alto. And we used to see Paul when he just had one son, would be 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 yeah great advisor 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 he's not really concerned with what could be an optimist yeah definitely an optimist and when it comes to startups for sure well one of the things i mentioned about him is he's one of my favorite writers and thinkers i read everything that he publishes he's published for a long time And 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 meetings with you.

16:47How important is it for you as well as the people on your team to be excellent writers, thinkers, communicators? Yeah, I don't know. 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. We try to do like a skills matrix of like, here are the important attributes of people and where do they assess themselves? 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. One of our values is to simplify. And Paul is the best example of this as a writer.

17:26He's like incredibly smart and intellectual, but he uses very simple language. He's passionate about using simple language as a great writer should be. In fact, Paul considers his main life calling not to be starting Y Combinator, but to be an essayist. And he's really passionate about simple writing. And part of that value comes from global logistics, really complicated. And so our ultimate mission is to make it easy. So easy there will be more trade. So it is simplifying, right? We're trying to simplify this very complicated thing to make it simple. and yet the industry has this aura of complexity.

18:04It allows for like mediocre people to hide because they maybe worked in this industry a decade and they learned all the buzzwords. They know how the world works. They don't know why though. And they couldn't explain it in simple terms. But 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 I call chauffeur knowledge, which is the knowledge your chauffeur gets from driving smart people around in the limousine. And they can repeat what they heard, but they don't know any of the substance of why and first principles, thinking, et cetera.

18:39So if you can't simplify a problem to a point where laymen can – smart laymen, but laymen 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 Balaji, Mark Andreessen, Peter Thiel. These are some of the people that I've gotten to know who are really next level, 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 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.

19:18Yep. 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 Tim Urban, for example, is such a great writer and attractive to lots of people because he takes these super complex different areas of life and you read him and he makes the reader feel smarter. I think great leaders do that. That's part of our job as leaders is to help simplify the complex world. It's a big part of your job. I want to hit on something that you just talked about is I love CEOs who are serious about values. And you mentioned Simplify being one of them.

19:53What are your other values? And if you could, I'd love to kind of like hear why the other ones are your values. Yeah, we have five values. And they start with the first one, which is empower your client. 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 shit, man? There's a lot of intransparency, a lot of mystery, a lot of complicated stuff. 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.

20:25And like, how do you build that long game motion? So that's number one. Playing the long game is another one of our core values is recognizing there is so much short-term thinking in this industry. Those values can come at odds with each other, actually. 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. What if the customer wants you to break the law and misdeclare something on customs or ship something that's hazardous? There's all kinds of ways that you could empower your client but actually not play the long game.

20:55There's an intentional tension that comes with that. 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 i could go imagine as if you owned this company but it's about breaking down bureaucracy asking why over and over again challenging not saying the names of departments as a reason you could or couldn't do something like if you're shipping i don't want to hear about origin like asia this happened oh actually a great example for us is we ship a lot from indonesia but we have any employees in Indonesia.

21:36We work with a local partner 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 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 an office in indonesia and this is to my senior leadership team in asia called them out publicly they were like oh a legal told us we can't and i was like it's very odd to me that statement so i was like who in the legal department you know because i made it illegal now after that 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 gonna talk to them i want to I'm not saying they're wrong.

22:31I 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. He's 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. Because when I talked to the head of legal, he was like, no, legal would never say that. That's not our job. We'll just tell you, here are the costs, here are the risks, here are the challenges. But it's a business decision whether to go and do that. I won't call him out because he might have been, he said it in private, but a great CEO told me, tell your people they don't have to listen to legal unless they tell you something is illegal.

23:04Otherwise, they're just giving you business advice. I like that. I want to use that. You know, no entrepreneur or whatever would be like, oh, the 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. Get the name of the person. So that value comes from that. Simplify, I 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 showing how complicated their world is. And you need me because look at all this complexity here.

23:37And if I can't understand something, I'm not the world's smartest person, but logistics, we're kind of on some level. We're shipping cardboard boxes from here to here. And we're trying to create a more streamlined flow to eliminate defects, to 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, 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, we're overcomplicating things. So yeah, that simplified value score. And then winning as a team, we're all on one team.

24:12I 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've got to align. We should not be at odds. How hard is that one though, Ryan? Because like you have 26 of those, you have 26 different groups that are meeting. There's probably more than that, right? Well, yeah. I mean, 26, just like having a meeting with you that they write up the six pager and then talk through it.

24:44So technically whoever's in charge of those 26 people, if that's how it's organized, this is the thing that we actually run across when we do like leadership development work within companies 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. 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.

25:15So 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 got to come through the culture, through the vision, through the commitment to the mission, to what we're trying to do, to alignment, to a larger, higher set of goals, through lots of teamwork. So like these meetings are not just with me, like other execs are there. People were identifying who else needs to be here. Everybody's reading all the 26 monthly business reviews and annual plans together.

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25:49There are a lot of work to map dependencies and say, hey, you own this. And then constant assessment of are these teams aligned? It is true. People will optimize for their own. Work structure changes can make a big difference in achieving an outcome. But I don't think there's anyone that's more complicated than freight forwarding, more interdependence. Because, 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 Coca-Cola in Vietnam doesn't need to cooperate with Coca-Cola in Mexico. They run their own little P &L.

26:23They just run fast. They do their own thing. But 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 its space on the boat, customs teams clearing the customs. So there's domain expertise and there's regional operational work, all needing to collaborate on each and every single transaction. So 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.

27:01But 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. Never underestimate the incentives. 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 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.

27:36It's a reminder 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 it's like 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 these incentives through the messiness of human beings that's why leaders exist yeah and the relationships really matter COVID 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.

28:16We stayed to work from home for way too long. Now, we're five days a week in office, but we stayed for like a couple of years too long. We should have just always worked through it in office for our business. 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 Chesky, the CEO of Airbnb, who's someone I really look up to on the culture front. And he recommended it. He got it from Steve Jobs of 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.

28:51It's not. But get the top 150 together 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 350 people. Gather them together and go through, here's what we're doing and why. 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 meet this person for 15 minutes. Talk through what you do, what they do. Just trying to create serendipity on some level. but I think that in-person is just key. I'm jealous of companies where just everybody works in one building.

29:31Is it hard to choose those 150? Yeah, it is. And I just do it. We just do it. 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 maybe it's a key designer or a staff engineer or a salesperson who's just absolutely crushing it or something.

30:08You want to have a mix of different people there. And then it's not the same every time. That has to be like, this is not a static list. If you're one of the flex providers who didn't get invited, it's like, it's fine. Maybe you'll come to the next one. Or here's these avenues of ways that you can contribute more to get invited. And it's not the only thing that we do. I'm trying to do more, like, as we get more and more profitable, our goal is to end this year sustainably, durably profitable as a company. Then a big way to reinvest, I think, is going to be these types of summits and getting – it's not cheap, right?

30:37We're doing the next one in Vietnam, taking 150 people to Vietnam. So I want to do more and more of that in different types of groups, right? The summits we do are, like, 300 people where we're coming together as 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. It'd be nice to do that more frequently in more places, like get people more exposure. Yeah. Getting together with people, there's just nothing beats that. I 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.

31:12And 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 costs 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. There's a lot that goes into that. It didn't necessarily go great from what I gathered. 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.

31:56I got to come back and run the show. Yeah, it clearly didn't go well or you don't hire the CEO and then plan to come back. Right. And I came back after six months, but a lot went wrong during that period. Why did we do it? I wasn't trying to hire a CEO. I was trying to hire a COO and his name is Dave Clark. 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. But he'd really come up through the supply chain logistics group there. He ran supply chain and logistics. So it seemed like a marriage made in heaven. I think I made the mistake of falling in love with the resume.

32:28But honestly, it's not Dave's. We had our problems, but I wouldn't blame Dave at all. 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 it turns out, I don't think I even needed that. I needed to have more confidence. But we're now, like, our key HR focus is just hiring from within. You got to promote from within.

33:03And so if I ever, someday I will pass the torch, you know, hopefully when I'm very old, and 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's just too hard to, too much to learn. The fundamental problems, the short-term proximate cause, we let costs get out of control and quality suffer. Our customers, our churn went up, our NPS with our customers went down and our costs ballooned. You're like, this is like a perfect storm. So 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.

33:36Did you think you weren't knowledgeable enough? Why bring in somebody else? Because I'm just trying to distinguish for maybe someone listening who 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 the best company in the world. And it's Amazon. You know what I'm saying? Like, I'm just wondering for that person, what was it? I'm a huge Amazon fan. I think Amazon is a really interesting company. And in our world of tech plus logistics, it's kind of an end of one type of company.

34:07Yeah. Maybe that's not quite true on a global basis, but in the United States, Amazon is like tech and logistics. That's who I think of besides Flexport. And the problems 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, remove defects, just like drive repeatability, reduce variability of outcomes? Just that whole 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.

34:42I'd hired a lot of good people from Amazon. A lot of them told me this guy was amazing, would be perfect for us. I trusted some people on the reference checks more than anything. Of course, I had some bad reference checks that I just ignored. So that was my fault. So those were, I was looking for someone who could do those types of things. Like I'm more of the creative type. I like to do different things every day, not the same thing over and over again. And operations is 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.

35:13And so I was looking for a partner to do that. 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 I 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 yeah, in hindsight, I should have had more confidence in my ability to go learn these things and put it in and get the team to own those challenges. 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.

35:50We're not a manufacturing business. And yet there's a lot of parallels. So it's actually very intellectually stimulated. They'd be like, oh, what is the concept of inventory in a logistics company? We don't have inventory, but 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 stuff's going bad all the time. You throw an interception, you get sacked, you got to bounce back, you got to stay cool, you got to get the play call in and call it with confidence, right?

36:28And I read that you said something, rule number one in a crisis is everybody will rally around the calmest 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 calmest person in the room? Well, it's great advice. I'm not that good at it. 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 people are just like disappointing you and sometimes valuable to get mad at someone and yell at them and what was the um the gentleman is never rude except on purpose 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 is that something you think about though or because some some exec teams it's just part of the sports background you just get used to that you're gonna to get ripped in front of all your buddies and that's just how it goes i don't think it's that bad actually 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 then the next time they ask you something they'll be like oh we better we better the next time that exec asked them to do something they're like we better deliver or ryan's gonna yell at him again i 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.

37:56I think, though, there is value if somebody is viewed as, this is like a Belichick-Brady thing, but somebody is viewed as above everybody else, you make sure that that's not true. I had a coach, I remember one of my favorite coaches, he pulled me aside and said, 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 so if you make a mistake, I might overdo it a little bit. actually I've built a ton of trust with me and him because he's like it's not gonna be fake it'll be when you mess up but just know and I know you can take it and so I think like there is 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 that background but I wish I did there's so much where do you pull like your leadership lessons.

38:50I 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? Where do you do it? Some of that. I have a good CEO group that there's 10 of us. I think CEOs of peer-level companies that we meet really regularly and give each other feedback and help support. How was that formed? I don't know. They already had it going and they invited me. I'm fascinated by these things because I think we need these things. All of us need these. I am curious there's probably some parts that you don't talk about but i am just curious about how the whole thing goes like what are the meetings are they formal informal how does it work they're semi-formal there's formal in terms of like we have it pre-scheduled you're only allowed to miss two a year or you get kicked out wow do you get together in person every other month in person wow are you guys located 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 and then we alternate sf or LA.

39:47So you have to fly every third month to the other city. Okay. We do updates. So you'd say, what's the best thing that's happening last month and the worst thing kind of personal and professional share. And then someone times it and make sure people don't go for too long. And then we save 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 recommend people, you got to find peers that can do that for you. Right. We're not in like a formal association with a bigger group, but I think it's kind of similar to what YPO does.

40:24Yeah. In their little formations. I think we probably copied it. So 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, again, back to simplicity and the, we all can envision just flipping a light switch. What's that all about? Oh, well, I like the light switch analogy because very similar in the old days, when electricity was first invented, every company had to have their own power plant in their factory.

41:02Well, originally before electricity, you had to put your plant next to a waterfall to make power off the water mill. But then when electricity came along, everybody ran their own generators. And it was only with the development of the grid, now we just take for granted that you had electricity and 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.

41:33It's generating a tiny bit more electricity on demand for you. We just totally take that for granted. And yet it powers everything that we do. And I think in logistics, in commerce, you have this mindset. You don't really think about it. The idea, 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 replenish and move it in. And 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.

42:09But 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? Yeah, we want to make it more like the electrical grid where you can just take it for granted and have it work on demand.

42:44Interesting. I like the simplicity and the use of metaphors and making something complex easy to understand. Changing gears a little bit before we run in a few minutes, 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 for the CEO. But what are some of the must-haves when someone's going to get promoted or hired into a role that's super important, like a leadership role?

43:19It's a number of things. Work ethic, very underrated. 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 we'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 that 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 accrue and how hard you work.

43:54And it's like basically the origin of capitalism comes from that 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 innate in everybody. Some people have it, some people don't. You can be any religion to have it, but 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 not born that smart.

44:26you 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 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 the communication that we talked about earlier, your ability to simplify and communicate well.

44:58And then there's, in our spaces, domain experience, which could be logistics, legal, finance, whatever the domain is that they gotta be, have seen a lot of edge cases and developed enough experience to 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 just like, how do you trust these external people that they're telling you? Do you know them better than they know the person?

45:30Yeah, you could see it, that they've actually done it while working at your company. That's ideal, right? Worked really, really hard, been humble, curious, learned new things. But we can't fill all the roles internally, which I so hard. But when it's external, I try to get someone whose referrals from people who work at the company are worth way more than a random reference check that the candidate themselves gave you, right? Right, right. That's my ideal. Like I've only hired one exec in the last couple of 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.

46:06So are you still doing much work with Founders Fund? 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. The end of the year, we turn profitable Q4 and then I think I'll have more options there. Most people in your position, they have moments 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.

46:39So 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. of work at it i guess i got two little kids two little girls so i'm trying 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 like constantly thinking about flex sports so really yeah constantly 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's 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 that's it's like hannibal right like hannibal the general he was always praised because his soldiers were never loyal were never defected they were always very loyal and he's 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.

47:49Well, you can't criticize him for that. If you're going to praise him for his soldiers, never defecting, uh, you know, on some level, you got to take the good with the bad. So are you saying though, cause 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.

48:22I 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. That's my thing. Yeah. But I mean, like, it's amazing to have kids because it gives you an 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? How are they getting purpose in the world? And then you have kids. You're like, oh, I get it. You just need to raise your kids. And that's all the purpose you ever need.

48:51So 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 all of a sudden you can, like you do, like 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 because I love this thing so much.

49:31And then you have the second one. You're like, wait a second. I'm capable. Like, it's just, it's bizarre, dude. I mean, being a dad is the best. It is the best. It is the best. and as uh so that work on constantly is like work on my take put my phone away don't pick it up don't get distracted it'll be there yeah but also the example of working hard is a really really good thing one more thing before we run dude you're meeting with a young person maybe like a newer employee who's straight out of college or straight out of like columbia business school like you were and they want to like leave a dent right like they want to leave a positive dent in the world what are some general pieces of life slash career advice you give to them oh i mean i think everything is about learning is like building your capabilities and learning.

50:09And I really like to point people to Charlie Munger's essay, Unworldly 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 the idea that in life, there's only a limited number of domains of areas. It's not infinite things. And yeah, these are arbitrary lines between those. You can say how many there are, but I 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.

50:45And so it's not an infinite problem to learn. To become worldly wise would mean you'd 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 life. And 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 we're going to read constantly, find the people who know the thing that you want to do and model them, ask them. Those are all good ideas.

51:20And then I guess the other one comes from Rene Girard, 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, have similar values to the ones you want to have that are working towards inspiring things that are leading the type of life that you want to lead because you're going to naturally imitate those people.

51:54And if you're not careful, you'll be imitating the wrong model. You will be, you will imitate someone. I think this is why, um, why Christianity can be really important is like imitate Christ, pick the ideal and imitate that rather than at least you're consciously choosing someone great to imitate. Otherwise you will imitate someone who's, you get it wrong and it can 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 you don't have that one role model you can have role models for different areas of development or different areas you're trying to learn luke burgess has a book called wanting which is all about renee 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 with people who have definitely sustained excellence they've generated a lot of wealth in their life they haven't inherited these are people who've worked really, really hard and made tons of money and are kind of world changers.

52:54And I'm super lucky to get to go. We've done it last 17 years. We have dinners every night. We hang out during the day. When I come back from that trip, I think differently, man, being around kind of world dominators, it raises your level of thinking. It truly, truly does. So I love that advice to put yourself in environments with people who do big things, who get after it, who are optimists 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. It's so good. 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, et cetera.

53:30And 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 that will inspire you, that you will learn from them, et cetera. But you don't, networking is not that useful. Like you come out of college and like, oh, I met so-and-so. Like, I've met tons of famous people and entrepreneurs, but like, it 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.

54:03So you got to work on yourself. The best networking tool is being insanely good at whatever the thing is that you do. Yeah. It really is. 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 those groups are ruthless too. Like they will, they're not afraid to disinvite people, right? They'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 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.

54:47I mean, in our case, like SaaS. 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, a senior job at Facebook. Facebook acquired it and killed it. It just wanted 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. 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.

55:18Fascinating dude. Hey, man, I love this. I'd love to continue and do it again as a little bit more time passes just to hear from you, man. I always learn a ton. I appreciate it, man. Likewise, man. Thanks a lot. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know what you learned from this great conversation with Ryan Peterson. A few takeaways from my notes. How about the tweet storm that saved Christmas when Ryan heard about the problems at the Long Beach Port? He asked the five whys, as he mentioned multiple times, the five whys, and then went to the front lines himself.

56:02This reminds me of General Stanley McChrystal and his front line obsession. I think senior leaders need to have a front line obsession. Ryan got a taco truck, rented a boat, and brought another high-powered CEO with him on the boat. Kind of held him captive, as he mentioned I should do. And then afterwards, he wrote a tweet storm about what he learned. It went viral. And then Governor Gavin Newsom called a couple hours later. and then policy changed a few hours after that. Ryan's action created change. That is frontline obsession. That is powerful. And then rule number one in a crisis is everybody will rally around the calmest person in the room.

56:50It is on us as leaders to be poised and level-headed when things go bad, as they inevitably will. Be prepared for those moments and how you will respond. Everybody will rally around the calmest person in the room. And I love his idea of going deeper than having quote chauffeur knowledge. A chauffeur can repeat back with the people they're driving said, but they don't know why. As leaders, we gotta go deeper than that. Understanding the things so that you can answer again those five whys and be able to describe it back to someone else with simplicity. That is when you truly show that you know something about that and not just having chauffeur knowledge.

57:38Once again, I would say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with Ryan Peterson. I think he'll help you become a more effective leader because you continue to do that. And you also go to Spotify and Apple Podcasts and you subscribe to the show. Really important. You write a thoughtful review and you rate the show, hopefully five stars. By doing all of that, you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much.

58:09Talk to you soon. Can't wait.

From the publisher

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

Ryan Petersen is the founder and CEO of Flexport, a technology-driven global logistics company. He's a leading voice in supply chain innovation and has been at the forefront of solving major trade and shipping challenges worldwide.

Notes:

  • "Arrogance is its own form of stupidity."
  • The Tweetstorm That Saved Christmas:
    Ryan shares the now-legendary story of how he rented a boat, brought tacos, and took another high-powered CEO with him to tour the Port of Long Beach during the supply chain crisis. His viral Twitter thread sparked immediate action, California Governor Gavin Newsom called within hours, and the policy changed shortly after. A masterclass in "doing the thing."
  • Frontline Obsession & Gemba Walks:
    Why Ryan frequently travels the world (visiting 19 countries last year) to meet employees and customers. He explains the power of Gemba walks, being physically present on the frontlines, and how it shapes his leadership.
  • How He Runs Flexport:
    Ryan's leadership playbook includes:
    • Managing through writing. Every one of his 26 teams writes a six-page memo monthly, followed by deep conversations.
    • Daily conversations with 30-40 employees to stay connected.
    • Living Flexport's values:
      Empower Clients, Play the Long Game, Act Like an Entrepreneur, Commit to the Vision, Ask Why 5 Times.
  • Leadership & Decision-Making:
    He shares his "must-haves" for hiring leaders:
    • Relentless Work Ethic
    • Intellectual Curiosity
    • Humility ("Even wise people are wrong 30% of the time.")
    • Reliability
    • Charisma
  • Lessons from Mentors:
    Ryan talks about advice from Paul Graham (Y Combinator) and Brian Chesky (Airbnb), including how gathering your top leaders in person sparks innovation and alignment.
  • Hard Decisions & Mistakes:
    He candidly discusses Flexport's CEO transition gone wrong, hiring Dave Clark from Amazon, and what he learned from that difficult chapter.
  • Personal Growth & Life Philosophy:
    Ryan shares his approach to lifelong learning, inspired by Charlie Munger and René Girard. He emphasizes reading widely, asking questions, and choosing role models wisely.
    • "We're all imitative people. Choose your role models wisely."
  • "We're making global trade as simple and reliable as flipping a light switch."
  • "Even wise people are wrong 30% of the time. You must stay humble."

More from The Learning Leader Show With Ryan Hawk

All 112 episodes
645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing SimplicityThe Learning Leader Show With Ryan Hawk · 58 min
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