The Learning Leader Show With Ryan Hawk - 411: Ryan Petersen (CEO of Flexport) - How To Build A High Velocity Team

Episode Date: March 21, 2021

Text LEARNERS to 44222 for more... Full show notes at www.LearningLeader.com Twitter/IG: @RyanHawk12  https://twitter.com/RyanHawk12 Ryan Petersen is the CEO and Founder of Flexport. Prior to starting Flexport to fix the user experience in global trade, Ryan was co-founder and CEO of ImportGenius.com, a data-as-a-service business for global shipping. Flexport hit a $3.2 Billion valuation after $1 billion investment led by SoftBank. Notes: Excellence = Curiosity - "It's a more fun way to live." Learners Appreciative Have fun "It doesn't have to be boring." The importance of writing as a leader: "I write a lot of essays. Some are published. Some aren't." Communication: "It's a huge part of the job of a leader." For investor updates... "It's good practice." Try to use humor, learn something new, don't be boring, get people "pumped up" Raising money from investors: "It's like your love life. You have to earn it. There are no shortcuts. You need to have a business that doesn't need them." "We built a track record over the 15 years prior to raising money." Masayoshi Son is the CEO of Softbank. He is a Japanese billionaire technology entrepreneur, investor, and philanthropist. Ryan met with him and earned a $1 Billion investment... Making Flexport worth $3.2 Billion. Flexport became the fastest growing company in Silicon Valley. Ryan wrote an essay about raising a lot of money so that they could ride out a "100 year storm." How was he able to raise so much? "Don't do an auction. I said, 'I'm only talking to you.' Create a win-win. See the world through their eyes." Masa had written a 300 year vision. Ryan said, "The audacity to have a 300 year vision, it just resonated with me." "One of our core values is to play the long game." Flexport enables all parties to move large product around the world. It was born out of Ryan discovering the pain of shipping. There is a lack of technology with freight forwarders. There was no culture of customer satisfaction. There was high friction - "We counted 984 steps to get a product shipped." Paul Graham, one of the greatest investors of all time and founder of Y-Combinator said this about Ryan Petersen: Ryan is what I call an armor-piercing shell: 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 Petersen." By 2016, Flexport was serving 700 clients across 64 countries. Tech Crunch described it as the unsexiest trillion-dollar startup. Flexport has grown to 1,800 employees across 14 offices and 6 warehouses, and 10,000 clients. His goal: "Drive velocity: You need speed in the right direction. Velocity is the key to success. That's culture ultimately." The two forms of bureaucracy: Too many rules, order No rules, no process, chaos Need to find the balance between the two "Transparency helps get people aligned." Doing an open Slack Q&A with all employees -- Helps with transparency. What Ryan looks for when hiring a leader? And why Ryan admires Parker Conrad from Zenefits: He's "hungry, curious, has a chip on his shoulder, determined, ambitious, and solves complex problems." The profession of sales: It's "one of the most misunderstood professions. It's part of all jobs. You have to persuade, create value." "Sales is about creating value for others. Create win-wins. So much is repeat games. Almost nothing is a one time transaction." Obsession with company culture: "When I reach out to top execs, they always take the call if I'm asking about culture." The secret to the tech industry: Everyone is willing to share tools, mindset, and lessons learned with one another. It's "normal to pick up the phone and ask." How did becoming a dad change him? "It's exhausting. Babies are fragile." Generalists vs. Specialists? The world needs more generalists. "Generalists are under-valued. Leaders need to be well-rounded and cross over into multiple disciplines." Has has Ryan learned to speak 6 languages? Read books, make flash cards, read the newspaper, hire a tutor... "You have to experience pain to learn. You have to like the pain." Life/Career Advice: Get out of student debt Read books. Your life will be different in 5 years based on the books you read. "Most people don't read books." Success compounds - Add up a lot of little wins

The goal of our culture is to drive velocity. And velocity, if you remember from your physics class, is different from speed. Velocity has a vector, you know, so it's speed in the right direction. Even if you change direction, how do you maintain speed into the curve? It's not like how big are you. Can you move fast in the right direction? And that's culture, ultimately. Welcome to the Learning Leader Show, presented by Rixie and Meyer.

I am your host, Ryan Hawk. Thank you so much for being here. Text learners to 4422 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders from all over the world, will receive a carefully curated email from me with the latest ideas, articles, books, podcasts, videos to help you start your week off right. You'll also receive details about how my book, Welcome to Management, will help you become a more effective leader. Text learners to 4422. Now on to tonight's featured leader, CEO of Flexport, Ryan Peterson.

He started the business in 2013, which is a purpose-built cloud software and data analytics platform. Flexport serves more than 10,000 customers in over 100 countries offering a full range of services, including ocean, air, truck, and rail freight. Ryan is a very thoughtful and intentional leader and certainly someone that I have loved getting to know. And the great investor, Paul Graham, said about him, Ryan is what I call an armor piercing shell. He's a founder who keeps going through obstacles that would make other people give up. A few of the topics we discuss, the importance of velocity.

Ryan shares why leaders need to help their team operate at the right speed and the right direction. And then how he raised $1 billion. and how that relates to you selling your ideas to others. And then he shares his belief about transparency and why it is critical to building trust. Ladies and gentlemen, you'll get so much out of this one. It's Ryan Peterson. Ryan, good to have you here on the Learning Leaders Show. Welcome.

Thank you. Thanks for having me. When you think about leaders, in your life and based upon all of your work, you have put yourself in position to be surrounded by fantastic people, great leaders, those who sustain excellence. I'm curious, what have you found that those people tend to have in common? Well, it's got to be the subject of your show. It's curiosity and wanting to learn and not feeling like they got all the answers. And that's also a more fun way to live. So for me, I'm like one of my core values are around learning and appreciation and

having fun that I don't think it has to be this boring corporate follow the rules type of life. Like that's not for me. That works for a lot of personalities, but I just can't do it. So I really gravitate towards people like that. But you know, I think most of the great leaders that I've been exposed to is just those who have written books because I mostly get my knowledge from books and it's like the most amazing thing is that the world's smartest people have taken the time to write things down that you can learn from them and so maybe my my sample is biased by those people who have written great books and I get to spend time you know so when when you read a book that you love I've I've heard that you like that you introduced to people who are new hires is

radical candor by Kim Malone Scott I had Kim on the show do you reach out to the authors after you read a book that you if they're still alive and with us do you reach out? and talk to him? I have talked to Kim, but not always, you know, it's like often they put their best ideas in the book. So it's like, what else do I got? But if I have questions, you know, in fact, our investor who led our series A and series B, and I think they're still maybe the second largest shareholder in the company is founders fund. They're either number one and number two largest shareholder. And that's Peter Thiel's fund. And the way I started my relationship with them was. was asking Peter questions about his book, zero to one. And it, one of those cliches, right?

You ask, you want money. You ask for advice. And if you want advice, you ask for money. And so I never asked him to invest. I just was like, hey, can you can't, you know, I got a couple of questions about your book. And then next thing I knew, he was investing in the business. So you, so it's obvious you get a lot of benefit from reading. And I've, I've, I've never found an excellent leader who's not constantly reading. What about writing? Um, are you, Do you try to get your thoughts from your mind on the page? Are you going to publish books? What about that aspect of the learning process?

I'm a big writer, almost too much. Like, I'll write essays a lot. It's like maybe this is just like the college student in me, like doesn't know what else to do when I have things that I want to share and I write an essay. Probably do one of those every month or so. Not all of them I publish even internally. Some of them are, some of them I publish. just like sent to the whole team.

There's my thoughts on this thing. But some of them are like, I don't want to distract everybody, but it's like an idea that I had like, hey, we should do this. And I look at our actual priorities. And I'm like, well, I don't want to change the priorities of the company right now. So maybe I'll just like share this with a handful of people. I have to be careful because then those go viral in the company. And next thing I know people are like doing my things because I wrote it.

What role from a communication perspective of a leader should writing have, not just in your company in the way you think about it, But if you were advising others, and I'm sure you get people are asking questions constantly now that you've done what you've done. And we're going to get to that in a second. But what role should the leader have in being an effective written and speaking communicator? It's a huge percentage of the job. And both those skills are very rare, surprisingly rare. Being a great writer, so many people end up writing like as if they were a corporation or something.

instead of like, hey, be a person, have a personality, stop using such fancy language. Like, do, you know, write the way you talk. And that's a pretty rare skill set and very valuable enough that people really value authenticity, as well as when you're speaking, right? A lot of people are just like really stiff and have trouble being themselves. And I don't know that that, I think practice is the answer probably for both writing in written, but realizing it's important. It comes first.

And it's, I think the first really important writing that I was doing for a flexport was actually our investor updates. I would write, I never wrote a regular investor update. And this is a secret for those of my investors out there now hearing this for the first time. I never, they probably didn't even notice, but I didn't have like, oh, every month I send the update or every quarter. I would write when there was something worth writing and try to do it often enough that it didn't even. noticed that there was no pattern to it. And make sure that I wanted to, I wanted to be humorous so people would be entertained. I think people want to be, same with public speaking. They wanted two things. They want to learn something and they want to not be bored. And I think in the other order,

they want to not be bored first and then they want to learn something. And so I always aspire to do that with my investor updates and get people kind of pumped. You know, if you're an investor and these venture investors, whether it's Angel or venture capitalist later stage, like they have a lot of companies in their portfolios. And when someone asks them, what's the best company? Like, you got to be on the top three. They're not going to have time to remember. So it's like, okay, that was always my goal.

It's like, I want when someone asks my investor, who's the best company in your portfolio right now or like, what are you excited about? I need to be tip of the tongue one of the top three things. So like, how do I make sure I'm writing that? And I was never expecting my investors to solve our problems. So I didn't like make long list of all the problems. I was like, what's awesome? You know, why should you be pumped?

And we'll solve our problems on our own. I more want investors to just think like we're the best. The theme of or the topic of raising money fascinates me. I've never done it. And I would imagine most people in the world haven't done it. However, I think there's a lot of a lot of the keys to raising. money and getting backed would apply in many other different professions, industries, jobs. It's kind of a sales job. It's a communication job. It's convincing them. You've got to be

persuasive. Can you take me inside the room? So maybe we'll pick one here. So in 2019, I believe SoftBank invested a billion dollars in Flexport, the company that you started that you're the CEO of. That gave you a post money valuation of $3.2 billion. So somebody wrote you a check for a billion dollars. And we can talk about that person as well, Masa. But can you like from start to finish, how does that, I don't know how much you're allowed to share, but as much as you can, what is that like to go from the initial time meeting him or the leaders of that company to the day when he gives you a check for a billion dollars? Raising money is it is, there are skills that translate to other parts of life. And I mean, it's not

that dissimilar to like your love life or something like you know just wanting it is not going to be enough like you have to earn it you have to be like the kind of person that someone would want to love that someone would want to give money to uh which means like there's not a lot of cheap there's not there's not great any any kind of hack that you're doing or shortcut is probably not going to blast right lying or anything else um and so first off is like have a good business have a business have a business doesn't need them, that you're going to succeed with or without them and then sort of change the leverage structure a little bit in the process, in the conversation that, you know, I want to back this person because he's going to win whether or not I invest. So those are the

kinds of people that get investment. I think a lot of founders who I meet who are trying to raise money sort of get it backwards and they're like, oh, I'm going to do this company if someone invest. You're like, well, they're probably not going to invest. Like they want to invest knowing that you're going to do it with or without them. So that's like, the first thing. It's like be the kind of, and by the way, if no one will invest in your business, like pick a different business. There's a lot. I did start out for 15 years before I raised my first dollar of venture capital. Really? Yeah, there's many other ways to make money in this world besides like raising money from venture capitalists. And, and those things are part of the reason

that when I did start to raise money for Flexport, the reason that it was reasonably straightforward was that I built a track record of success that people were like, okay, I want to back this person. people think these are like just overnight success stories but it was a long lot of years of building good companies bad companies learning you know developing and earning credibility with investors so the specific um soft bank round was it was an interesting one so flexport uh was a big and we'd already raised about 350 million dollars up to that point we'd been on this crazy growth trajectory we were one of the fastest growing companies in the history of Silicon Valley technology business attacking a massive market. So even though I forget our revenue back then, but like last year we did

$1.3 billion in revenue gap revenue, we're still like a tiny 0.1% of global logistics or something. I mean, we're just still, it's just a big market. And because the market so big, we knew that capital was going to be a key. had either competitive advantage or weakness, you know. But it's a huge ability to invest in the business and keep scaling it. It was just crucial. So we knew we needed to raise a lot of money. Or that we didn't need to, actually.

But raising a lot of money would make us a much better company, let's say. So strategically it was the right thing to do. There are very few places you can raise that kind of money. You know, you can count on one hand, like the number of people that can make that decision and write you a billion dollar check. Did you have that, was that your goal like we need to raise a billion dollars? And we'd like to have it come from one place or how does that work? It's a nice round number.

And I think we're all numerologists at heart. So there was a goal like we won a billion. I mean, it's not a coincidence that was a billion even. Like, if it had been euros, I would have raised a billion euros. So I mean, the human brain is kind of simple like that. We didn't need to, you know, but there's only one person that could do that. If we hadn't done a billion, we would have raised a smaller amount from different people. But like, I wanted to go big.

I wanted to raise enough capital that no matter what happens to the economy, what happens to global shipping, trade wars, shooting wars. There's a lot of disrupt, you know, now you had a pandemic. There's a lot of disruptions that could happen. I mean, talk about writing. I actually wrote an essay about why we needed, why we wanted to raise so much money, why we did raise that much money. It was all about black swans and knowing you got to have enough balance to you.

to ride out 100-year storms. And so we wanted to raise a lot of money. And there's not a, like I said, very few places that you can go. And South Bank is the one that was like actually writing those checks. And so I, there's a number of different philosophies on how to raise, you know, like a competitive round. And do you want to get a market clearing price? You get lots of parties involved and almost run an auction. And I actually think fundraising, that's the wrong way to approach it, that people don't want to be in an auction.

They want to feel like they're valued. They want to feel like there's a relationship here. Money is not, it's not efficient market. Not all money is created equal. And people want to be valued for their network, for their reputation, for their values, for the alignment with the founder, et cetera. And so the mistakes I've made in the past and previous funding runs that didn't go that well, and that some of them actually completely failed and I had to get bailed out, those are where I was trying to run a more competitive process and get 15 different investors at the table and play them off each other and try to play fancy games.

And I blew it up and it totally failed. So I learned my lesson the hard way from that. And so actually with something I didn't, I gave them an exclusive. I don't know if it was legally, but I just told them like, look, I'm not going to go talk. to other people. I'm only talking to you. I'll give you guys three months, do as much diligence as you want, ask as many questions as you want to get comfortable. But I want you to have me an answer for us by, I think we started that process in October. And I was like, I want to have an answer from you by January. January, I'm going to start talking to other investors. And so in January, they gave us a term sheet

for the billion dollars on what I thought was good, you know, good terms. But it was also good for them like they ended up buying it almost a third of the business they didn't do the full billion by the way they did 700 million and then existing investors came for the other 300 um but uh but yeah so it was a you have to create a win win and i think that's the key in any relationship um and especially in business is like you've got to create win wins with all your counterparties and the key to that it's not as hard as it sounds is like see the world through their eyes try to understand what they want and and making sure that and what investors want is pretty straightforward they want high returns they want low risk and they want a long duration they want to be able to let the money ride and keep

compounding decade you know for decades the good investors do right hedge funds are just flipping stuff but but you want to find people who are aligned in that with those three things and then and then it's okay show show them how our story gives them that and i read that you said um so the leader from SoftBank, his name's Masa Yossi Son, am I pronouncing that right? Masa. I've heard of college for short. Usually people call it Masa. Masa. So he also invested in WeWork and that one kind of went the other way, right? WeWork was famous of 2020. Some pandemic related, some CEO related. And so that that one is, I guess they could still be okay, but it went south. What was it like with him? Because I read a quote that you said that he has a 300-year vision.

that 300-year vision resonated with you, which to me, like a five- or 10-year vision seems like a long time. 300-year seems like a really long time. What was it about that that resonated with you so much? Well, the audacity of it, you know, I think it's more, there's a great, there's a great, I think it's like a PDF document. You'll have to Google and find it, but it's like SoftBank 300-year vision or something. You should be able to find it.

It's just a fascinating, like, I don't know, I found it really refreshing to find someone who's just like, thinking so exotically about the future and long term long long term it's a bit extreme i think some of it is just like kind of a plant the flag show that we're extreme long term thinkers and the real detailed part of it is like a 30 year vision but but i really enjoyed the presentation you know it's all about increasing human happiness reducing sorrow like you know these are noble goals like you don't see a lot of venture capital as being like our goal is to reduce sorrow for humanity. So I just appreciated that. Let's talk a little bit about what Flexport does, what it is for those who don't know. Can you share at a high level why Flexport needed to exist, why you were the

guy to start it and what you guys do? Flexport's a platform for global trade, a technology solution that enables all the different parties required to move product around the world, like large volume product between any two locations on planet Earth. We connect all those parties in one place, make it super simple for everybody, and create those win-wins. And so you're bringing on, like, most of the, there's this really interesting thing. You asked, why am I the person who started? Well, I used to be the first, I was working for my older brother and his business partner,

his college roommate. And we were the first dealers for a company called G Lee, which is the Chinese car company that bought Volvo. though. And we were buying their motorcycles and selling them on eBay motors and Amazon. Like we were real entrepreneurs. I was telling you, I did startups for like 15 years. We never called it a startup. We never raised money. We were just trying to, you know, make money, do it, do a business. And in that process is where I just discovered the pain of shipping something, especially a complex thing, like a motorcycle where you've got to go clear customs regulations, but also the Department of Transportation,

EPA, probably some state and local licenses, too. It was a real pain. And so there were two big pain points that I felt that I was working with these companies that the companies that Flex Sports replacing are called freight forwarders. And these are like, basically it's a man with a phone and a Cadillac and a small, there's thousands of them and they just help you kind of broker this transaction. And there's no technology, very little technology. Some of the bigger ones have some tech, but none of them was founded after Netscape.

So they're kind of like, they just weren't built from the ground up to be technology businesses. And I think there's a lot of use for technology. Show me where my stuff is. When is it going to arrive? Help me simplify this very high friction process. And it's an incredibly frictionful process that, and we're still, one of the things I love about where we're still peeling the onion and learning all the different processes and steps and middlemen and layers to it of how to,

how to get cargo move. But the first thing was lack of tech and huge opportunity for tech. And second, I think it might even be more important. It's just like this, there was no culture of customer obsession. I felt like all the freight companies out there were just trying to conspire to take advantage. George Bernard Shaw has this great quote. He says, every profession is a conspiracy against the laity. And sort of freight forward is just a poster child for that. It's like old boys club. They got all this lingo. They know how it works. I know what the current freight rates are. You have no idea if I'm getting ripped off or not.

And so I thought between these two of like tech, actually simplifying things, giving people data, helping them make decisions and then a culture of like, let's do marketing as education. Let's teach people how this works. Let's build trust and make money over the long term by creating those relationships. So that was where the problem originally came from.

But it's this fascinating thing where high friction. I mean, we've identified nine. 984 steps to get a product ship from door to door. And it's taken us years to figure that out. Again, learning like nonstop. So very high friction. And at the same time, if you notice, there have been this crazy renaissance of like direct-to-consumer businesses that are growing faster than ever.

The Warby Parker is all birds, Lulu Lemon, Peloton. You can go on and on. dozens and dozens of these fast-growing e-com businesses. And you're like, how are they growing this fast? It's a really interesting question, given all the friction and giving how hard it is to launch of physical goods business from manufacturing, etc. And it turns out, well, there are these awesome platforms where you've got Shopify to build your sites, you don't have to spend millions.

You've got AWS. If you want to do custom development, you don't have to run your own servers. You have Foxcon or other types of companies that just manufacture your product. You don't have to build a factory anymore. You got Striped to take payments. And actually, almost all of the world's direct-to-consumer e-com businesses use for export because you no longer have to build this big bureaucratic logistics department. We're sort of your control tower in the cloud.

And that's what we basically built it out of my own experience of like, this is what I wanted to have when I was an importer and trying to build a brand and trying to, you know, sell products online. And so that's where it came from was from my own experience and suffering the and try to build something that I would want to use. So you went through Y Combinator in 2014. Is that right? Yep.

And I love, I read, I think every Paul Graham essay that he writes. I imagine you do too. And I was reading what he said about you. And he said, Ryan is what I call an armor piercing shell, a founder who keeps going through obstacles that would make other people give up. because or but he's not just determined he sees that 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 um what's your relationship like with with paul graham by the way if

if you're listening or watching and you haven't read his essays do it now i've shared a billion of them on my mindful monday emails but but talk to me about your relationship with paul graham as well as you being an armor piercing shell. To be honest, I never heard that quote before. That's pretty great. You got to email that to me. I didn't know he said that about me. Paul's a friend of mine.

I was very lucky that we, Flexport was in the very last batch before he retired at Y Combinator. And my older brother also did Y Combinator. And so my brother introduced me to Paul even before I started. And I think he kind of like, like you like, can you describe Y Combinator for people who don't, who have never heard of it. It's an investment fund slash incubator. They now do like over 100, maybe even over 200 companies a year where they'll give you,

I don't know the terms. I think it's 120K for 7% of your business, which sounds like a lot. And it is, but it's a network. And so it's not just the network of the people who work in Y Combinator, who are impressive people, mostly all startup. founders, but the other people who go through it are, you know, top companies, Airbnb, Dropbox, Stripe, so many, DoorDash, so many good companies. And you get to meet these people. I don't know, it's certainly the people in your batch become your friends. So to me, that was the big value of it.

It was like, I like to learn. I want to have friends who are doing awesome things and are teaching me stuff and inspiring me. So, yeah, but that's why Combinator, in a nutshell, pretty one of the best investment funds of all time given the list of companies they invested on those terms and so how is your relationship with paul how's that been helpful how's that developed over time since you since you've been there now it's been what seven years since you were there yeah well uh paul's awesome paul uh i also read all of his posts and i'm inspired by that but he's been just like really helpful paul's a kind of guy who i think the best investors and i think Paul's probably top two or three startup investors of all time.

The best investors don't ask what could go wrong. They ask what would happen if everything went right. Like what could happen here? The reality is these startups are power law returns. So it doesn't matter if things go wrong as long you have a big portfolio if you're an investor. And what you care about is if everything went right, how much would this company impact the world and what would it, you know, what would it be worth? And so his winners pay for all the losers. And I thought, you know, they're thinking of upside more so than anything else.

It's all that upside. And so Paul's like the best at that and like a real dreamer and a thinker about a creative mind about what could happen. And so he's and I'm lucky that he's taking Flexport under his wing to an extent and helped me. He's emailed engineers for me. Tell them to join. Engineers love Paul because he's a classic hacker. And so they like that's been helpful. He's helped introduce a few investors on the way.

Most recently, he donated a million dollars to flexport.org, which is our nonprofit group that does humanitarian logistics. And he helped us really seed that fund. We raised $10 million last year to work on COVID projects, help get masks to frontline health care workers. And Paul was the first large check into that. So, Ryan, one of the things I like to do if I'm lucky enough to know somebody who knows you, And I reach out to them and I'll say, tell me something about them that I can't find on the internet.

And so one of your best sales professionals is one of my good friends. I actually officiated his wedding. His name's Jonathan, butnik. And Jonathan, I met him years ago. He used to work for the Green Bay Packers. And that's my younger brother played for the Packers.

And so we developed their friendship for, it's been a while now. And I said, tell me something about Ryan that I can't find on the internet. and he shared a few things he mentioned radical candor getting that he mentioned a paul graham essay schlap blindness but what i want to cover is i said well what's he like as a leader and what's the culture like and he said he's first of all he said he's as legit as it gets which as you can imagine is a really good compliment and then he says he focuses heavily on culture he's dedicated a lot of time to seek out and meet with founders of companies that grew fast and are now institutions and he studies culture and how they are able to create it and sustain it.

And he said one of the things he does is he's also very accessible and welcomes good slash challenging questions. And we have an all company, quote, ask exec Slack channel where he will answer anything. So there's a lot there. But from a culture perspective, I think the leading from the front, being willing just to jump on Slack and answer any question, talk to me about your overall leadership. philosophy for your company and the culture that you're trying to build and how you see from one of your sales guys, one of your best sales guys says, like, I love this dude. This is why I keep coming to work

because I love our leadership. That's awesome. Yeah, I mean, I do think my primary job, like your first job when you're starting a company is to get product market fit. And we got that really, really early. And so my job became very quickly thereafter is create the culture, defend the culture, make sure that your culture is empowering people to be creative, innovative, and execute. And really, the goal of our culture is to drive velocity. And velocity, if you remember from your physics class, is different from speed. Velocity has a vector, you know, so it's speed in the right direction. Sometimes you've got to go slow to, you know, to make sure you're going the right direction. But it's, and that's still velocity, your goal is, even if you

change direction, how do you maintain? speed into the curve, right? And I think velocities are really interesting area to learn about. Even talk about the formula for kinetic energy, going back to physics again, kinetic energy is one half of mass times your velocity squared. That's the size of the explosion when you hit something. And so you'll remember, this is also relevant for a football player. This is why like the little guys can hit so hard. It's because the velocity is squared. Your mass is only a linear function. So when you hit someone, it's like, how fast are you going? That's your velocity. And so I think that velocity is the key to success. It's not like how big are you? It's like, can you move fast in the right direction?

And that's culture ultimately, because you've got to be able to get people aligned. Are we working on the right things, are we going the right directions, make decisions so that people can take action. You've got to empower them to take action so that they're not, you know, like, and there's, by the way, there's two forms of bureaucracy. There's two causes of bureaucracy. One is like way too many rules and process and committees and everything has to pass. And that that is one cause of bureaucracy. So it's too much order. And the other cause of bureaucracy is no rules. and no process, and no one knows how anything works, and it's too much chaos. And, yeah, everyone's moving really fast, but you're kind of like, the net sum is no movement

because you're moving in different directions, and you get, again, physics sort of like really hot molecules all bouncing off each other, but not moving anywhere. And so the challenge of creating a great culture that allows for velocities is that line right between order and chaos of like, what's the right amount of, process that people can know who has decision rights, how do decisions get made around here? Can we just act or who has veto rights on decisions? Are we going the right direction? Do we have the right tools, the right process for that versus too much process? And just like, oh my God, this place is boring and no one gets anything done because everything has to run through five committees.

And that's an obsession of mine. I think some companies, Amazon's probably the best example of just a high velocity culture. I'm not saying it's the best culture in the world, but certainly they've got some great processes you can learn from to drive velocity into a company. And Amazon's a great example as well of like where velocity and that kinetic energy that comes from moving so fast wins versus mass, right? If you're just, if mass is all that mattered, Walmart would have been an impenetrable barrier that nobody could have Costco too.

Like no one could ever compete with the scale of these things. but Amazon proved that like move really fast run circles around them and you can actually you can win so that's my definitely my obsession I think transparency helps I think getting folks aligned and understanding where we're going and so our ask exec channel is you know

some people would not like this thing can be challenged but I'd rather have the question surface I'd rather have the challenges put on the table if you don't address things like you that are that people are talking about it's not that they don't talk about it yeah it goes into the black market of where there's no standard of truth and there's rumors and i am curious about that what's that like where are some of the things that that pop up that you answer directly and how

frequently are you doing this because i i feel like this is from a place that has excellent culture the leader is willing and able which are two separate things willing and able to answer those questions of people and even maybe complaints, which I'm guessing come up too. A little bit, a little bit. I mean, it's pretty positive. Like, you know, it's also a good barometer for your culture is like, are people just complaining all the time or is there is it about business, about interesting? I don't know.

Last week, I'm just looking at it right now. Last week, we got a question about Tesla buying Bitcoin. We'll flexport buy Bitcoin from our treasury. It's a cool question. Yeah. Like, what do you say to that? Like, what do you say to that? Well, they ask if we accept Bitcoin.

I said, well, we already do. That's a, you know, people can pay us some Bitcoin anytime they what. As far as investing, I just said, hey, maybe someday, but right now it's not a priority. I think it's a cool idea, but we, you know, no, no, no, you know, I don't, I don't promise to like, go and spend a lot of time on the answer, but I'll answer it. Some of them, a few of them have led to like longer essays that all write where I'm like, hey, this is a bigger thing. And so, for example, someone asked a challenging question after we raised the billion dollars from SoftBank, which was a we took a lot of dilution.

We sold them, sold the investor base that invested in that round, almost a third of the company. And at our stage, that laid in the game to take a 30% dilution was a pretty, you know, it's a fair question. Like, did we really need to take that much dilution at this point?

Do we need that much money? Why did we raise so much? And I started answering, I realized this is a longer essay. And that's where I wrote that longer essay I was talking about before, about black swans and like, my foundational belief that you should have enough cash in the bank to write out any kind of disruption or a black swan event in your business.

What about when they gave you a billion dollars, did you and other leaders or investors get to take any off the table? We didn't. I mean, I probably, well, oh, in fact, what we did was about a couple of months later, I had another investor wanted to come in. And we did a tender offer so that we allowed employees to sell up to 15% of their vested equity. Anyone who had equity that was vested could sell up to 15% of it to that. But only like 20% of people participated that were eligible. And I didn't sell any. I'm long

flexport. I want to buy more shares, not sell. So the bulk of your wealth is in the company. Like it's not sitting in your checking account or another investment account. It's in flexport. 99% in flexport. I'm all in. I only own one stock, which is GameStop. And I just bought some shares for fun. Wow. So, so you, you are literally all your money is where your mouth is. You're all in. I have, uh, I do have a house that I bought. And I've invested in a lot of techs. I own a different business actually that I started with my brother. Oh, called the import genius with our other partner from the motorcycle business. Uh, and so I, I'm a shareholder in that. And it generates cash. And I take all the money from that and I invested in startups besides what I put into my house.

So I'm, I got a real estate house. Oh, and I bought. Bitcoin starting in 2012. So I've got my portfolio though, Flexport, Bitcoin, my house, and a bunch of startups, and 10 shares of GameStop for fun. Okay. So you invest in other leaders. This is a good, good, good, good, I'm glad you brought this up. When you're looking at other people to invest in, what are the qualities in those people

that like the must haves in order for you to invest in them? I like creative people. I like curious people and I really like people who teach me things. And so if I'm talking to you and I don't learn anything from a founder that I, you know, if you're not able to go,

hey, there's this thing that I know about the world that I'm like, okay, this is not that interest. You know, like the world's so fascinated. You should be, and if you're studying some space that I never heard of, like you should know all kinds of cool stuff about it that you can teach me. So those are the things that I look for. I think ambition,

make sure that they're starting it for the right reasons. Like they actually want to solve a problem, not just like it'd be cool to be a founder. I don't really like investing in people who are like so determined to start a company, but they don't know which. And they're like going to try to figure that out. I'm like, that's not really how it works.

Like you got to find a real problem that you and then and then be obsessed with solving that problem. Can you think of a recent one that you've invested in that where it was, it was of a, maybe you named the person where they, you really learned a lot or maybe there's more than one where like, wow, I had no idea and I'm fascinated by this person and what they were able to teach me. And I, and I couldn't wait to invest.

Probably it's Parker Conrad, the founder of Rippling and before that benefits. And Parker is just an incredibly smart, curious. and hungry and driven entrepreneur. And he's got a chip on his shoulder because of what happened with Xennafits where he was pushed out. And he just like is determined. And he taught me early on a lot about go to market

and how to build a sales team. He since has taught me a lot about product management, domain modeling, data modeling, like how do you organize org design that falls out of that? How do you organize your teams to be for velocity? And he's really ambitious and like willing to solve very, very complex problems. Ripling is kind of HR, everything HR and IT, your single system of record for your workforce.

And then, but so they sell everything benefits, IT, they rent you a computer. I haven't even looked at the list. Payroll. And they just keep finding new products. And he's not afraid of like, isn't that too much? Like shouldn't you focus? And I think I like people who are like don't really think, believe in like, oh, the world should be simple. You should do one thing and be good at it.

It's like, yeah, the value is usually created when you do lots of stuff and they're ambitious. You mentioned sales. And I love to talk to you and get your philosophy. I mean, my first job after I got done playing sports was was a cubicle inside sales rep job, pounded in the fans. And really, really glad that that was my first experience in the business world because I learned that the skills I learned through the training and through failing and through rejection have really benefited me for everything else that I've then I've then gone on to do. I sense in the, I think sales is one of the most noble professions in the world. If people didn't sell, then nothing would happen. And you mentioned before we started recording about why you love your sales team so much.

what's your philosophy on the profession and the art of selling this is i think it's one of the most misunderstood and and maligned professions it's really a sad i'm almost a toxic aspect of of modern culture is that we think sales when when most people hear the word sales they assign a negative salesperson that's like a negative reaction instinctual i haven't seen science on this but i know enough people to know that that's probably how it would happen if you went and studied it. And you know it's deep in the culture because there are, it's probably like 20% of all the jobs are explicitly sales jobs. And it's part of every job. You've got to be an influencer. You've got whatever you're doing. You've got to influence people on your ideas. Even if you're a scientist, you've got to sell your

ideas. You've got to convince other people that you're right. You got to persuade. And you've got to create value for other people before you expect something back. And when you understand that, that, then sales becomes a beautiful thing. And yet, there are only three universities in the United States that I can find. There might be others out there, but there are only three that I've been able to find that offer a major in sales. And that's, I feel I remember them, Weber State, Florida State and Baylor are the only three universities. So kudos to you, deans of those schools for actually like teaching the thing, because it is something that can be taught. It is a super valuable skill set and a great way to learn the ropes in business and learn that like you've got to

create value for other people. The image of the used car salesperson is just lying and doing a one-time transaction and selling things and not caring. That's like that's not real sales. Like sales is consultative. It's understanding the problems of your of your target of someone that you're trying to sell to. Understand what their problems are. And then understand the capabilities of your organization. How could I solve that problem? And if you can solve the person's problem, you've completed the deal. You consummate the transaction and you're a good salesperson. Like, what a beautiful thing.

You're solving other people's problems. And you only get paid when you do that. And so teaching my philosophy is that. It's like you've got to create win-wins. You've got to create value for the other side and try to get people to focus less and less on the results and more and more on the process and like actually helping your customer base. And it's really tough because this is antithesis. I go to a lot of sales management, sales leadership, where it's all about celebrating the number and the quota and striking the gong and just only, it's only output.

And you don't really care how they did it. And I think actually the paradox in these things is that you will do better if you don't care how you do. And if you instead just focus on what you do and enjoy the process. And, you know, I think our television is like, I'm sure this is true in sports too. It's like the best athletes aren't just the ones focus on their stats. It's like they're practicing all day. You know, Larry Bird practices shot so many times.

He enjoyed practice. And that's what made him great, not like focusing on the outcome. And so, but our culture doesn't teach that, right? We only show sports athletes at their winning moment or, you know, they don't show them like in the gym every day training. Yeah, exactly. I remember early in my career, my dad told me, when you go through bad like bad salespeople or training they'll have this close close close and they'll use these exclamation points and he goes I want you to view the close as the period

at the end of a long sentence so it's the process to get there and then the close just naturally happens because of everything that led up to it there isn't this and then there's more or here's the discount or it's just it just naturally happens where it almost doesn't even feel like an event because you've built the relationship. Yeah, of course, we signed the up. Yeah, you've solved problems. And by the end, it's just a natural step. It's not a big deal.

It's not a big deal. So like, is you going to sign it? No, well, yeah, of course, that's just the next step. That's because we've already done all of this work leading up to it. And this is just one of the periods. We're going to have many of these because we're building a relationship on trust. Yeah, totally. Help you. Right.

And so much like remembering that things are repeat games. Yeah. So much of stuff that is taught in the world, like, assumes that we're in this, a lot of like classical economic theory and negotiations, tactics and stuff. Like so much of it is just like assuming that things are one time and like almost nothing in the real world is like that. Like almost everything is a repeat game.

People are going to do business. Once you can do business with someone, you're going to keep doing business with them and they're going to tell their friends and stuff, right? I went to business school and business school has a negotiations class, which is my favorite class in business school probably. Because you do like simulated negotiations and, And both sides get a piece of paper that the case and you, you know, you read your role. You've got to negotiate this and the other.

And what's really cool is that there's like, I forget how many people in the class. I call it 30 people in the class. So you've got 15 pairs. You can see who's good in a negotiation. But what I would love to see a study is, is follow those people throughout their careers. Because what I, what I've learned is that my classmates who were the best in the negotiations class have not had great career. because those negotiations were so far from reality. They were like one-time games.

And yeah, the person really won because they won because they were like aggressive and willing to stretch the truth and like play the hand in a really, but like in a repeat game world, which is the real world, people don't want to work with someone like that. And actually I was like not that good in negotiations class. But I've done much better because I'm like, look, I'm trying to create a win-win.

I'm trying to actually. But win-win doesn't matter in a one-off negotiation in a simulated environment. Right. Well, it's just playing the long game I've really learned over probably last five or six years doing the show. The people, I'm asked a lot. Like, what have you found that these people have in common? And the first one I always bring up is the fact that they're extremely curious people, which is awesome because most of them have accomplished so much a guy like you. And yet you're so incredibly curious when you could just go chill on the beach for half the year, probably and still be fine. but the other part is that they view life and they view business from a long-term perspective,

not trying just to hit the next quarter or not trying to get the quick win, that there are times when you may not get the best of it because you don't think that way. You're thinking longer term where long-term we're going to be better off, even if initially we don't get the best of this deal or best of whatever it is that you're doing because you don't think that way. You're thinking more longer term. Yeah, yep, yep. The other thing that I've noticed that the top people have in common is their obsession with company culture.

And it's long game, right? That is like it doesn't, it's not obvious how it pays dividends. And but it, but it happens even though it's not measurable. And not being overly focused on the measurable things, but being able to being willing to work on things that are like, your judgment tells you that this will be good. And culture is one of those. And this really resonated with me when I was trying to understand culture, what it is, how to describe it, how to troubleshoot it, how to improve it. Whenever I would reach out to a top exec at one of the great tech companies in the world,

mostly tech companies, but other companies too, but they would always take the call if I was asking about culture. If I'm calling you to ask, if I was calling the head of sales from LinkedIn, in to ask him about sales, he'll refer me to like a director of sales operations or somebody. But when I'm like, hey, can you tell me about how you bring your values to life through your communication? It's like, ah, yeah, let's do a call. Talk about that. So you see immediately like what's important to them. And they were all willing. And I actually think this is the secret to the technology industry success is because it's not really an industry. The technology

industry is all over it's just the tools and a mindset and an evolution and the idea of using evolutionary principles which is diversify select and amplify agile sort of like try things iterate build that's what technology is about it's not about an industry and therefore the tech companies don't compete with each other and so they're happy to share lessons and then because of the lesson sharing and best practices and cultural norms like spread really easily the best practices get taken up in lots of companies. And so, like, I can go learn from LinkedIn. Whereas if you're in your industry as like, we're in the freight industry,

the other freight companies, my peers don't want to, they don't want to help me. I'm too competitive. So by, it's actually one of the key advantages is that information can really flow freely between companies and best practices get adopted and spread and amplified. And that's, yeah, I think a real hidden gem for why tech companies can really move so fast. It's like we're able to copy each other because we don't compete. Well, how common is it though that a CEO founder who has done really well picks up the phone to call somebody else? Because there are some that think they've got to figure it out or, hey, this is what we do inside here.

I don't need anybody. Like I sense, though, to you it seems normal and just intuitive in the way that you are. How common is that though throughout Silicon Valley or the tech industry to just pick up the phone and call another founder, another CEO, another head of a part of a business in order to learn from them? I'd say it's the norm in my experience. Now, I might be, my sample might be a little skewed because those are the kinds of people that I spend more time with. And I don't hear from the ones who aren't doing that. Right. But it is, I would say it's the norm from my experience.

is like top and top top people. I had a one of the, I won't say his name because he reached out to me privately on Twitter yesterday, but one of the top tech companies in the world, CEO, DM me on Twitter to ask me about our planning process because I mentioned it in the podcast. And like, he was curious, you know?

So like that's, that is the norm is people reaching out and learning. And the reality is if you don't do that, you're going to stall out. Like there's nobody smart enough to know all the things. Nobody in the world. How do you feel when that CEO reached out to you and asked for your advice, your help? I thought it was super cool. Our planning process is, I'm proud of it, put a lot of work into it, but it's also kind of a mess.

So I also thought it was funny. I shared it with the team that runs it. Hey, you guys, look at this. We're getting better, but we're still very much evolving. And we're not, it's funny to me that that CEO wanted to learn from us. He can't learn from us. We have good ideas, but we haven't solved it. And even our planning process, I copied it from Salesforce and Amazon and Google and I blended the three processes that they use and made it more flex porty.

So I don't think we invented anything there, but maybe it's useful. I want to shift gears for one sec before we get right back to it. You had your first child last year. Is that correct? I did. Yeah, in September. How did becoming a dad change your life? my daughter has some health problems that she's working through she's going to be fine but

it was been exhausting so I had to really reevaluate my priorities and I think I would have had to anyways but it was only working half time for like a quarter last year and that really eye-opening I think realizing how fragile babies are I mean they're they're resilient but at the same time like those children, none of us would be alive without our parents loving us. And that is true for every single human on planet Earth. Like you did not. And that I thought was a kind of eye-opening. We see San Francisco, all sorts of homeless people, jug addicts, like criminals.

And you're like, well, there's somebody out there. That person has a mom somewhere who loved them by definition or they wouldn't be here. I thought that was like a new perspective for me. Give me a little bit more empathy. I mean, it's kind of sad too. but help me reflect a little bit. And then, yeah, I'm just like overjoyed. My daughter is the cutest thing in the world,

so I love spending time with her. She's only six months old right now. So she's still, you know, she's not like talking or anything yet, but she's still just so fun. She's so cute. How does it change how you lead and manage your team? You're the people that directly work for you

because I feel like there's so much carryover. I know she's only six months, but still like it just like changes you instantly, I feel like, as far as you mentioned empathy, and I think that's definitely one of the feelings. But how does that impact you as a leader at work? We've always tried to be a great place to work for parents. You know, best people and everyone wants to have kids.

Like not everyone, but like most people are going to end up having kids. And if you don't create a great workforce, a great place to work for people who want to have kids or have car kids, like you're going to lose in this world. So, but I didn't have firsthand experience in how to do that. I was the only member of our executive team that doesn't have kids. So we were already doing some of those things. But it definitely eye-opening for me. The biggest probably thing was actually going, my wife going through pregnancy and

watching how hard that was for her. And she works at J.P. Morgan. And so watching how challenging that is. And J.P. Morgan is a great, great place for parents. It's a great culture for that. But thinking like, wow, it's really tough. So how do I create kind of like environments of we haven't changed things as a result of my personal situation. But we for example created even before I had the baby policies to allow women to like ease back into the workforce after they've had a baby working part time and taking a little bit less salary, but maybe work three days a week or two.

You know, like allow for flexible situations that are good for the, you know, let them define how they want to work. So I thought that that reinforced for me, like, wow, those are really important. That working from home was so valuable for her during COVID. We were all working from home. And during her pregnancy, working from home, like she would feel nauseous and just being like, okay, I'm just go lay down. That's okay. And at the office. So like thinking more, I'm thinking more about that, those types of things for how to help pregnant women and new mothers, especially.

New dads, too. but I haven't like solved any of these things but definitely makes me reflect a lot more on it of how do we create that environment. Yeah. Just a couple more things, but I have to ask you. I talked to David Epstein yesterday. He wrote Range and I've heard you talk about generalists versus specialist. Yeah. And David is definitely one of my favorite recent books.

And I got to record them a few times since he's published the book. How do you view generalists? versus specialist and when, especially when hiring and building a team and building a culture of when to value a generalist versus specialist, if there is a separate time or I'm all generalists, I'm all specialists. What do you think about that? I just think generalists are underrated in our culture. All of the education system, as you go progress further and further, what you do is become more and more specialized. And, you know, a history major, a history PhD is not someone who knows more about history than me. It's someone who knows everything about the year 1790 in France

or in Paris, like in very, you know, you just get more and more focused on one thing. I mean, I think, and that's fine. Actually, there's value in being a specialist, but I think our society has over-emphasized that. And therefore, there's untapped value in being a generalist and someone who can cross domains and disciplines. And some of the best ideas come when you take an idea from one discipline and bring it to another. And it's just crucial. You know, Richard Feynman, famous businessman, spent like two years as a biologist and did some incredible breakthrough work as a biologist

just because he was able to bring mental models and actual mathematical models out of physics into biology. And so I think there's a lot of examples of that, a lot of, even Flexport is that. It's like I was an entrepreneur coming from the e-commerce space. recognizing that freight is broken and that, you know, like an outsider view of that can be really valuable. But very rare, and I think one of the things that you want to find in leaders is the ability to cross over between technology and sales, between sales and people, and HR and culture, knowing some basics of the law, knowing basics of finance and accounting, Like, these are, being really well-rounded in the business world is exceedingly rare.

People are afraid of things they don't know instead of being curious about it. I also read that you are multilingual four or five languages. Is that right? You speak four-five languages? I have spoken five or six languages fluently at various stages of my life. Currently, my Chinese is super rusty, so I'm afraid to, like, claim it. But I can impress them like little old ladies in the grocery store with my Chinese sometimes. So is there a practical purpose behind that or are you just curious?

It was, I don't think you should study languages for practical purposes. Because of opportunity costs. Like you're going to, unless you're married or want to be married to someone from a different, who speaks a different language or your family, right? But other than that, practical reasons probably don't, the opportunity costs, you better off studying computer programming. or something. No, for me, it was joy. I enjoyed learning new cultures and meeting people. I'm like, I don't know. I'm not actually good at learning languages, but I just have fun at it. You tend to get good

at things that you enjoy. How do you do it? Do you immerse yourself in like a country that speaks that language? Read books. What's your way to do it? I have a methodology that in, it's all the things. So first off, you read a grammar textbook, like at least a whole, just read the whole book, you know the basics of that language, sort of Spanish 101 or something. Read the book. Two is flashcards. Now there's mobile mobile app flashcards that are really good.

Memorize is a great app for that, Duolingo. Three is read the newspaper. Four is get a tutor. These days that's easier than ever. You can find one on Skype or whatever. There's different apps for these. Just discussion.

You have to experience pain to learn something like a language. It's like going to the gym. You're not going to get strong if you don't go through the pain of working out. And I think a lot of people think like language learning is going to be just easy and like oh software is going to make this easy and like if it so you have to teach yourself to like the pain right like you probably when you were playing

football like learn to enjoy that pain of working out it wasn't it didn't feel like pain even though it sort of is right um and that that's a mental not everyone can do it i think when we're just born in different ways like i'll probably never get the same amount of pleasure as your brother from like hitting someone really hard or something, right? That's not, that's not fun for me, but he, he enjoys it. And I think so, but you can reprogram your brain to like things. And so you've got to throw yourself into off the deep end and embrace the uncertainty and the pain and the embarrassment when learning a language. Like everyone's going to think you're really stupid. And no one wants to be stupid. Like I get on a bus and I can't even have a conversation with a bus driver about where it's going.

most people that is just like so horrifying they could not possibly allow their ego to suffer this kind of like this person thinks I'm an idiot and but if you can you know you get to the point where that's fun like I enjoy it I would just laugh you know and find some funny jokes and say one thing and people it's very hard to be really funny in another language in fact if you learn too much of another language all of a sudden they're testing you for like this person genuinely interesting and funny and like that's like almost impossible But when you know a little bit, it's like really easy to be funny because you just sound like an idiot. So I just enjoyed the process. Yeah, I speak Spanish and Portuguese pretty well. Chinese, I'm losing it day by day. French and Italian, I can like have fun. Wow. I just sense a huge amount of humility there because you have to not be scared of looking like an idiot.

I don't sense that you are at all. And that probably helps you in a number of other areas of your life. One more question before we go, man. young person coming out of college, smart, ambitious, giver, they're a good, curious person. They want to make an impact. What are some general pieces of life slash career advice you'd give to that person? Two or three things that I think are most important is one is get out of debt. If you have student debt, which is like, I think the biggest problem in our society in the United

States is just how much student debt people are burdened with. And it's like, no wonder capitalism is less popular. is like 50% of the country has no chance of ever owning any capital. They've got too much debt. And why would they be excited about the model of free market economics? So getting out of debt is a terrible way to live. I see a lot of people make bad decisions because they just have to make those monthly payments. And so get any job, there's nothing wrong with that, making sure you're paying down your debt.

And these interest rates, like my student loans when I graduated from school were like 8%. That's not cheap debt. I assume interest rates are much lower now, but still, that's an 8% guaranteed return. So don't invest in the stock market until you pay down your debt, because that's a guaranteed return, which stock market returns are not guaranteed at all. Second would be reading books, you know, and the difference between who you are today and who you'll be in five years is almost entirely made up of the books that you read. And there are some hacks for reading books, by the way.

Find a podcast with the author. and maybe it's a little bit easier. You can do it while you walk or whatever. Audible, it's good. But search YouTube for almost any author if you can't bring your, for nonfiction. If you can't find, if you can't bring yourself to read the book or I've got so many books I want to read. I don't have time to read all the books that I want to read. That's one of my hacks.

I'll just search the YouTube 20 minutes. And you can listen at one and a half to two X speed too. So in 20 minutes you can get 80% of the value of reading the book for a lot of stuff. So I think, you know, be curious. you can be shocked. Like, most people don't read anything at all. Like, the average American does not read a book every year. And so if you're, it's not that hard if these things compound too, you know, you read, read a book every month. Like, pretty soon you know more. And if you, I've read eight books in a week, on a Saturday just by watching eight YouTube videos for 20

minutes each. Like, so, you know, you can actually, success compounds would be the last lesson, is that it'll feel like you're not making a lot of progress. But those little wins you've got to celebrate because the success does compound. And don't expect to go straight to the end and be super, super famous or successful. It's like little wins, little wins, benefit, you know, celebrate the little wins. Keep building on them. And you'll find that over the long, you know, you stay added after many years, you'll be surprisingly successful.

consistency is one of the least sexy attributes of very excellent people at their craft i mean steve martin was an overnight success it took him 10 years of doing stand-up comedies in bars sometimes with with less than 10 people and what do you know 10 years later he's selling out arenas that's all it took it's because he consistently showed up every day and i think and you set yourself up in a way that you can't blow up like you know i assume he had some side income something so that he could maintain that and going all in is overrated. Like having a nice, consistent

process so you can't lose. Like, when I was starting, my earlier company is pre-flexport, I got a job teaching the GMET, which is the course to get into business school. I got a job, and it wasn't, like, these are flexible things, right? It's like tutoring.

I got a flexible hour position helping people with their website to drive traffic. And I got, and my third job was doing writing case studies. for business school cases in Africa. And so I had three part-time jobs. And then that was enough to start making my payments

on my student debt. And then it was like, hey, I don't need my company to be this big giant success. I'm just gonna do it because I like it. And, you know, I knew if I stayed in the fight long enough, I'd be successful. So it's like, how do you set yourself up for long-term success in a way that you enjoy

every day of the process and not like, oh, betting all in, and not needing anybody's permission. I never needed someone to give me permission to do my life the way I wanted to do it. Love it. Ryan Peterson, man, thanks so much for investing your time with me today. I got notes for hours with you, man. I would love to potentially do another one down the road.

I'm done. This is a great conversation, Ryan. So appreciate all the hard work. And you're doing the right thing is helping people learn and develop themselves. Oh, thank you. It means a lot, man. is there a place you'd like to send people to learn more, maybe, whether it's about Flexport or something else online?

You know, actually one of the things I'm most proud of is Flexport.org, which is our nonprofit group that does logistics for humanitarian and relief logistics. I think it's one of the best forms of philanthropy out there because when a lot, like normal nonprofits have to spend like 30 or 40% of their budget raising more money. It's kind of like a bit of a Ponzi, you know, like raise money to raise money. And when you do logistics as philanthropy, it's like 100% of the money, it goes straight towards helping goods by definition get delivered where they're needed. So I think it's going to be a pretty powerful impact.

And I'm really proud of like the way we use our superpowers. We can ship anything anywhere. We're doing it for refugee camps. We've got programs right now to get stuff for warm clothes and stuff for Texas. All these people have their houses flooded, shipping mattresses down there. Like, you know, there's always a problem somewhere in the world. So flexport.org, you can learn more about the stuff we do there. Love it, flexport.org.

Thanks again, man. I'd love to continue our dialogue, man, as we both progress. Cool. We'll stay in touch. Awesome. Thanks, man. What a great combination of depth of thinking, curiosity, high intellectual wattage, and just a kind person.

I really enjoyed speaking with Ryan Peterson. And a big shout out to my good friend, Jonathan Butnik, who is, a sales professional at Flexport. He first made me aware of Ryan and then told me that I'd want to talk to him. And Jonathan is exactly right. I'm so glad I had this one. A few takeaways from my notes. When he said that raising money is similar to your love life,

meaning you have to earn it. And it needs to be a win-win agreement. I completely agree. And I think that's also ties into when he spoke about the professional. of selling when you are working to convince someone else to back you or to believe in you these need to be win-win mutually beneficial relationships just like your love life and then the thought of velocity speed in the right direction you could tell this is important to Ryan and it reminded me of when I spoke with Jim Collins and when he defined leadership and he said

Leadership is the art of getting people to want to do what must be done. And so excellent leaders first know the direction. They know what must be done. And then they have a way to inspire others to aggressively go in that direction. I see the similarities between what Jim defines as excellent leadership and what Ryan values in velocity. And then the question Paul Graham likes to ask, Paul Graham, one of the greatest investors in history, what would happen if everything goes right? Meaning he looks at investments from an upside perspective, the potential.

Whenever I was hiring for leadership roles, one of the questions I like to ask is how high is their ceiling? Perhaps they don't have enough experience right now for some, but I care more about their potential, their upside and their ceiling. And I think just like investing in a company, it's how we invest in people. And as we make hiring decisions, look for opportunities with really high upsides and really high ceilings, believing that if things go right, it could be a bona fide winner. Once again, thank you for continuing to spread the message. and telling a friend or two, you should listen to the Learning Leader Show. This episode with Ryan Peterson

will really help you become a more effective leader. And because you do that, and because you also write reviews on Apple Podcasts and rate the show, hopefully five stars, 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 much.

Talk to this soon. Can't wait.