#107 Founding CRO at Flexport, Ben Braverman: The Power of Genuine Curiosity

Sales gets fucking boring if you are not a genuinely curious person. If you aren't actually curious, like, hey, how does a toilet company work? Hey, how are sweatpants made? If you don't care about the answers to these questions, you're going to have to find all kinds of funky ways to motivate yourself to be a good seller. If you can be intrinsically motivated by understanding how the world works, and if you can do that day in, day out, there's sort of an unlimited well of potential because you don't get tired of going on the road. You don't get tired of going to people's offices. You don't get tired of calling them a second, third, fourth time because you've tapped into something more genuine than just, hey, I'm trying to sell you some shit.

Hi, I'm Jubin, operating partner at Kleiner Perkins, and I'm excited that you're tuning into Grit, a podcast that sits down with amazing leaders every week to discuss what it takes to create, build, and scale world-class organizations. The goal of this is not for it to be a highlight reel of how successful my guests are, rather a candid exploration of how hard it is, both personally and professionally, to build history-making companies. Speaking of incredible companies, we don't do sponsorships on the show. So if you're inspired by the stories of my guests, my call to action is to reach out and let's find a great home for you in the Kleiner portfolio. So you're late. Yeah, because you had to go to the Gucci store.

I had to buy all new clothes.

And you hadn't bought clothes in 2 years? Have you gone outside? Have you been in the public?

I've been in Wyoming.

Like, are you doing anything?

I'm skiing. I'm doing Zooms. We moved to Wyoming at the beginning of the pandemic. It is not a place where you need to wear fancy clothes. Not a place where I'm giving a lot of talks. Saastr doesn't have any events there. And so I haven't needed to wear nice stuff. A lot of my, I think the nice stuff I own is packed away even. And I was wearing different nice stuff when I was CRO of Flexport. You know, I was traveling around, I was meeting traditional businesses, wearing sport coats, suits, suits. Like, I wouldn't wear a suit, but I was wearing like slacks and a sport coat generally. For this part of my life, it feels like that's a little too formal to go give a talk on growth.

It is too formal. Yeah, but don't you have like t-shirt and jeans that you could have worn? No, instead of going to the bougie store.

Dude, I'm wearing— if I stood up right now, you felt the pants I'm wearing, they're made of whatever material— if you went to like a clown college, the pants I'm wearing are the same pants those guys are wearing. And the same fit. Because they're tremendously comfortable, I can move like Bruce Lee in these bad boys, but I don't look the best. So I went in, I got pants that fit. I was telling you, my body is bigger than the Italians want human men to be. So I have to go to this store, I tell them before I come in, "Look, my legs are bigger than your pants. Whatever you're gonna be able to find, just lay it out before I get there, and eliminate everything where if I'm giving you that heads up, eliminate everything that you think is gonna be too small." And here I am thinking, "Well, maybe Ben's dressing up for me." No, no, no.

I thought maybe, maybe you wanted to look good for an audio-only podcast.

No, I mean, listen, I do wanna look good now. I got a haircut yesterday. That was, I mean, partially for you. Uh-huh. But no, this is for, so I actually, the worst public engagement I've ever done was a disaster event. And so tomorrow is my redemption.

What do you mean your worst?

At some point when I was like actively CRO of Flexport, I agreed to give a talk at Saastr.

I watched it.

And then did not prepare for it at all.

I thought it was good. Is this the one where you talked about the 4 stages of growth and then the first stage It was like the 0 to 1, and then you realized on stage that nobody is at the 0 to 1 stage of their growth trajectory.

Yeah, same talk. Yeah, I think that it's that one. It was one of those moments where you're like, oh, you should prepare for things, particularly for things in front of hundreds or thousands of people. It's funny, like I'm the kind of person that I remember the losses so much more clearly than the wins. I was telling Ryan, you know, founder of Flexport today, I basically don't remember any of the good investments I've made. The two bad investments I've made in my life, like as a venture investor or an angel, like I feel physical pain. Like I feel like the kind of shame and embarrassment that I assume like a gambling addict feels, right? I have the kind of brain that just gravitates towards let's learn from the losses and like the wins. Okay, great. That's wonderful. But let's really learn from the losses.

My team and I are in a funny tug of war right now because especially with the podcast as it's grown in pretty serious popularity, which is weird to see, but an unexpected but cool. I'm only soliciting negative feedback. All I want is like, what can I do better? And now it's gotten to the point where my ego is just too fragile to keep taking all of the, like, like there's just too many things.

How do you get people to give you real negative feedback?

Well, so the people on my team love doing it. They do actually. They do love telling me negative feedback because how do I get people on my team to give me, I just constantly solicit it. And I think in some way, I give them negative feedback. And so it's almost like a tit-for-tat because the way that I behave around them is also looking for improvements in them. It's not just me. And so I kind of try and be authentic in that way. Like, you know, like I see dead people, I just see problems. I see problems in others and I see problems in myself. And so I just want to improve them.

There's a growing movement on Reddit and 4chan right now. The hypothesis is that the modern man is so physically ill-equipped to deal with combat or violence that they have to be ultraconformist. I have no idea if this is true. This is just like, this is like a theory that is circulating the internet right now. And I think if you want to be super direct with other people, it may be you have to study like the combat arts and get to the point where if in the state of nature you could survive on your own. Because at some part of your brain, like, you know whether that's true or not. Like, you know if you would be capable of surviving in the state of nature. And if you know you couldn't, how direct can you really be with another human being?

Absolutely. I, and I, my ego is more fragile than I thought. And the thing is, I think the other way that I try and approach it is that I start, even today, I'll give you an example. This happened like 15 minutes ago where I have a rule of thumb with my prep docs for my guests that they can't go more than 2 pages because if it goes more than 2 pages, it's not a conversation. It's like me going through the doc. Right. And so what I've been experimenting with a little bit more is how short can I make the prep doc in the allotted time that we have? And so I asked the team, hey, I had the Sweetgreen CEO on, that prep doc was shorter. Here are the things that I saw that I thought were better and worse about it. Specifically, here's all the things that I thought could improve. And then that kind of like sparks the fire of like, I've been meaning to tell you like this, this, and this, you know? I don't know. I don't know if that works or not, but I try and lead with it.

How, how often do you do this?

It's a weekly. I mean, I sometimes I batch a few in a week, but it's released weekly. So it nets out to at least once a week.

And this is a tremendous amount of work to actually process one of these and put out a good one.

It takes 25% of my time in my job. I say that while also today, we had, cuz we had a pretty short turnaround from yesterday saying like, hey, I'm in town. Me being like, all right, let's do it today. You know, my run this morning, I listened to a podcast anyway, but I was just listening to your podcast. Now, is that prep? I don't know. I guess like I enjoyed the podcast. I've actually already listened to it, so I was just listening to it again for fun.

I'm honored.

But it is still work.

It's work.

It's work.

I, I'm sure you know Harry Stabbings, right? Yeah. If you call Harry at any hour of any day, he will answer the phone. I think because running a media company and doing venture in parallel, it's totally rational and they're symbiotic and they feed each other. And like, if you can do them both well, it's incredibly powerful, but it's so hard.

So hard.

God bless you for doing it. Thanks.

Thanks for having me. I'm excited. And this is also why there's a graveyard of podcasts, because the stat is like 60-something percent of podcasts don't make it past episode 2 because most people love the idea of the podcast, but the actual execution in earnest is very difficult. It's really hard.

Do you have like a nephew or something behind the scenes? It's like banging this out for you.

And the other problem is it's very difficult for me to outsource the prep because the prep guides so much of what I want to talk about. Now again, it is kind of a self-fulfilling prophecy because I get to know people that's very important for my job and my prep is studying amazing leaders. I reach out to people that I want to talk to and the people that I want to talk to, I want to learn from. And so for me to have the opportunity to do prep on you, it's like I should be doing that anyway. That's making me a more effective coach for our portfolio.

That's incredibly nice of you to say and charitable.

So anyway, I'm glad to have you here, late or not. It's a pleasure. I wanted to ask you something that struck me in all the conversations that I had, in all of the videos that I watched, in the podcasts that I listened to, is that you are unabashedly yourself. You do not give a shit. You are just you. I wonder, has it always been that way?

You know, when I was in grade school, I got in trouble because I would just wander off. I would tell the teacher I was going to the bathroom or I was going to do something, and I would just disappear from the campus entirely. I wasn't doing it to be difficult. I've always sort of had to do what I was going to do. And I think everybody is, honestly, if you listen to the voice in your head, we all kind of have to do what we're compelled to do. And I just feel really lucky that for the most part, I'm compelled to do things that are positive and useful and valuable, at least in the financial And I'm super lucky that I worked for people who, like my first boss ever in life was an Austrian guy who had taken a company public in Germany and had it all fell apart and moved to the US. And he hired me when I was like a 19-year-old college dropout. And then my next boss after that was Amada Kuhn, who's now the founder of Mercury. And he knew that I had this really non-traditional background and hired me to do sales anyway, made me his head of sales really quickly anyway. And so I think I just was super, super lucky that I had people early on who were just like, no, you can, you can be you. Like, just go do you. If you're performing and you're generating the kind of numbers that you're generating, be you. That's almost like hitting the, hitting the professional lottery, honestly.

As you kind of embark on new frontiers of your professional life, let's say when you joined Flexport as the CRO and like employee 3, and all of a sudden you're talking to logistics people, or head of supply chains, or whatever it is that are— they come in suits.

Yeah.

It's a very different thing.

Totally.

You go into that world. Did you ever feel pressure to be somebody different?

Yeah, I felt tremendous pressure. I told you before we started recording, I gained like 50 pounds in the course of being— You look good. Thank you. Thank you so much. I'm trying to lose most.

You look better than you did at the Saastr talk. You definitely lost like 30 pounds at least since then.

There you go. See, not being CRO anymore, I'm just trimming right down. But if— sorry, what was the question?

The question was like when you go into a customer meeting for the first time where you're in a new environment, do you feel pressure to conform to that environment?

I got so excited that you mentioned my weight loss. I got totally, totally lost in the conversation. I found it was a superpower, this idea that we were outsiders. And again, like so much of confidence is being honest with yourself about what you are and what you're not. And we were really honest with ourselves that we did not know logistics or supply chain. Nearly as well as our customers did. And I think if you try to walk in and convince them of anything otherwise, you're going to fail spectacularly because people are smart, right? And they can tell if you know less about something than they do. And in our case, there was just no way that we could claim after, you know, my case, I was, I was doing ad tech for years before Flexport. I could not claim I was a logistics expert, certainly not in the first year. But if you walk into someone's office and you're like, look, isn't it weird that Google and Bloomberg invested in this freight forwarder? Isn't that like, isn't that like a weird situation? Aren't you somewhat curious about why they did that? And that's the context. And then, by the way, you're the expert in the room. Like, I have come in as an outsider to your industry. We've raised some money from folks who normally back software companies. We hired people who normally work at software companies, and we need you. We desperately need you, Mr. or Mrs. Expert, who's sitting on the customer side. Like, we need you to tell us about your day, what you care about, how you're gold. And if you're willing to do that, we actually have people that can build better software, we think, than the folks who would normally be building for you in your industry. And people found that like earnest, honest approach. I think they were refreshed by it. Immediately puts everybody at ease. We're like, okay, this person isn't trying to sell me anything. They just came to my office to learn. And very quickly then we would take what we learned, we'd go build either a V1 or a prototype, or at least like show them the beginnings of what we could build, whatever they were asking for. And that was like an amazing way to build these relationships where like maybe you weren't going to sell something as quickly as you actually wanted to, but you were going to earn a lot of trust. And actually, it was kind of hard as the years went on to lose that playbook, like to not be able to walk into their office and go, look, I'm a total novice. Explain to me how this works. Because that question is very disarming and very effective.

Makes total sense. And before I get too deep into everything that you've done, I generally start these things the exact same way. In this case, it's a delayed start, but that's okay. There's no playbook here. I'm going to read your background back to you.

Sure.

And then maybe we'll fill in a few blanks and go from there.

Sure.

All right. So you were at Vassar College but did not graduate.

Yeah, I went to Vassar because I was supposed to go to Tulane and Katrina hit. This is '05.

How old are you?

I am 35.

Dude, you're young.

I'm young. Yeah. Basically, I wasn't going to go to college. And then Tulane was like, look, if you submit your SAT scores, we will— you'll get a scholarship and you can basically come for free. I was like, okay great, New Orleans, let's go baby, let's have some fun. I was going down to New Orleans, my first day there Katrina hits. We're on a bus to Jackson, Mississippi, and I start emailing colleges that I'd interacted with before on the bus. And Vassar had rejected me, and I literally, I had been waitlisted at Vassar, they'd rejected me, this is like part of me deciding I didn't wanna go to college in the first place. So I emailed them back, basically a hustle, about hey, I'm a Katrina refugee, I need a place to matriculate for 6 months, whatever. So I went there for one semester. All the other Katrina kids that went to Vassar stayed, and ultimately I just, I decided to leave. But yeah, that's how I ended up there.

Wow. I didn't know that story. And I have more questions about this, but I'm going to continue on and then come back and revisit it. You went to Hays App as like your first kind of sales gig for a year or so. Then you went to URX, which I think is the company that you had mentioned was the founders that you'd work with that are now at Mercury, right?

No, that's Hazap.

That's Hazap.

Okay, cool.

And then you went to URX. Yeah.

And that office was across the street from—

No kidding.

Yeah.

Have you been in this office before?

I've never been in this one. No.

Well, welcome.

But it was literally 136.

I'm super curious. Has this area—

This area has always been sort of a little oasis in SoMa.

So weird, right? Then you went to URX. It was ultimately acquired by Pinterest. You spent not even a year there.

Yeah, generally.

Then you joined what was at the time a tiny company, barely a company called Flexport.

Yeah.

As like employee number 3, sub 5, right? Did you start as the chief revenue officer?

Yeah. If you, if you take a big enough pay cut, you can ask for a title. And in this case, Ryan was still making the decision about what title he was okay with. And I just put it on LinkedIn, CRO, and it was like, all right, fine. That's hilarious. And he lived with it. And luckily we grew fast enough that it started off as sort of an outrageous title and it became less outrageous over the years.

It's hilarious. So you did that for almost 6 years, 5 and a half. Then you became the chief customer officer, basically when the ride was like over-ish for you on the transition out, kind of like figuring out what was next.

Yep.

Spent about 2 years-ish doing that. And then you started what's called the Flexport Fund, basically a fund within the company investing in adjacent technologies. For those listening that do not know Flexport, last valuation in February of this year was raised at $8 billion, 15 rounds raised total, over $2 billion of capital. Put into this company, Founders Fund, Andreessen, etc., etc.

Yeah.

Can you give like the 30 seconds, like what does Flexport do?

Yeah, Flexport is what you call like a full-stack business in the sense that we are both a software company and a service provider. And the way our customers experience us is, let's say you're Lululemon, you produce really high-quality goods all over Asia, Vietnam being one of your hubs. You need a partner who can pick those goods up and we're talking about huge quantities of goods, shipping containers, airplanes full— who can pick those goods up, correctly export them from Vietnam, get them onto an airplane, onto a boat, move them around the world, again, correctly process the shipment into the country where they're going to be sold. So effectively, you have cargo that needs to be picked up. Flexport stitches together the 10 or 15 discrete services from the pickup, the regulatory services, the tax prep, compliance, all these things that have to happen for goods to move around the world. and we stitch it together for our customer such that when they log into the Flexport platform, they have God mode. Like they can see the world, they can see their, their shipments moving in real time. They can search by product. Effectively everything they need to know about their supply chain is at their fingertips. And it's a UI that feels like software that was built for them. It doesn't feel like it was built in the '90s, which most of the alternatives were. And the real, like the genius of Flexport is we figured out how to basically sell SaaS to a customer who desperately needed it, but who had no budget for it. And what I mean by that is If you picture one of our clients, we have a client who spends about $40 million a year with Flexport. They're one of the largest toilet importers in America. So like toilets, maybe an unsexy business, incredible customer for us, like literally $40 million a year in spend. On that $40 million in spend, you know what their software budget is?

Small. I'm going to guess tiny.

I think it's zero. I think I literally think it's a $0 software budget to manage $40 million in global transportation and then all of the repercussions of like if that supply chain works or if it doesn't. That is very typical of a cost center. Like, by definition, if you were working in supply chain transportation, for the most part, you were considered a cost center in your organization. And even though without you, your business literally will stop, you have no budget for things other than your core commodity, which is, in our case, buying transportation services. We figured out, though, like, this is an amazing business as it is. Like, every legacy forwarder prints cash. You know, you had Will Urban on before. He came from Expeditors. One of the big publicly traded forwarders, they just spit out an enormous amount of cash every year. Their employees have one of the biggest bonus pools of any company you've ever heard of. Their shareholders get enormous dividend. Freight forwarding is an amazing business. You can actually afford to give away to your customer what would otherwise be a SaaS platform if they're willing to buy more of their freight and transportation services from you. And before Flexport, what a company would do is they would maybe buy from 2, 3, 4, 5 vendors they would pull in all their data in Excel and they would collate it. With Flexport, the bargain we're striking with them is, look, you're only gonna buy from one vendor. From that vendor, you have access to every airline, every ocean carrier, every truck, so you're not actually limited, but you aren't gonna be sourcing from 4 or 5 forwarders anymore because that means your data's gonna be split. When you buy from us, you're gonna buy as much of your service from us as humanly possible. You're not gonna spend a dollar more. It's gonna, whatever your budget was with the legacy guys, it's gonna be the same budget with us, maybe hopefully a little bit less, but even worst case will be the same, but you're gonna get this incredible platform and dedicated team built into the program. And that bargain just works super well.

The company, like this was in 2018, was named the 8th fastest growing company in the US. 3-year growth of this, that doesn't even make sense, 16,000%. And by the way, 16,000% in 2018 was not on a small base of revenue. That's not going from $100 to whatever, $16,000 or whatever the math is. Like it's, That's a, that's crazy.

No, I mean, people ask me if I'm gonna go do another CRO gig and the reason I probably won't is I don't think you can follow this one. Like, I think I'm, I'm competent. I'm, I'm good at what I do. Maybe one of the best at what I do. I don't think you can just will a company or I don't, I don't think you can even with discipline, will, smart people for it to come together to grow this fast. It's an act of God.

It will never be as good. And it's funny cuz we're in some of these companies at Kleiner. And I go and give talks to generally the go-to-market or the company, and I tell them like, you might be having the best ride of your life. And by the way, I bet you it doesn't feel like it. And so like that dream that you had growing up of like being at one of these ripping companies, I legitimately think you're experiencing it. And I'll benchmark the revenue of the best companies and how long it took them, and I'll show them where they are. And I'll say like, look, it took Okta 7 years to get to $100 million. It took this company— and obviously your revenue's a little bit different because it's not pure SaaS in that respect. And so I try and explain like, you're in it, but boy, they have no idea. I had no idea. Like when I was operating, I didn't— I never even hit a home run. Like maybe double here or there, like nothing crazy. Anyway, it's hard to tell the forest from the trees when you're in the midst of it, isn't it?

I think the biggest mistake I made as an investor so far in my life anyway, is undervaluing my own experience at Flexport, where when things are working that well, it feels like a miracle. Like, we literally, we were like a cult. We would walk around in the first years of Flexport, just look at each other and go, every day, 5 good things happen at Flexport. It just felt like we were figuring so much out. The customer demand was unbelievable. There were more meetings on the calendar. Like, literally, like, it's the only time in my life where I've seen salespeople just complaining, I have too many meetings, I can't handle this many customers. And you're right, in the moment it feels brutal because you can never scale fast enough to keep up with it and you never feel like you're living up to the opportunity. But yeah, in retrospect you're like, oh my God, this was a once in a lifetime thing.

I've heard you say that if you could give advice to your younger self, you would have said enjoy it more.

For sure.

What do you mean? Like, as it relates to this?

You know, we're not curing cancer. Ultimately, we are doing things that we try to make the world better, But the stakes are financial. They are not existential. No one's gonna live or die based on the work we do at most of our startups. The best we can do is try to create value for the world, create an environment that everybody enjoys, certainly do no harm in the universe as best you can. But if you take things seriously to the point that it impacts your health, like I told you, I put on a bunch of weight, or it impacts the way you treat other people where like it's just really easy to snap at people or, you know, give negative feedback in a way that's not super loving or whatever it may be. When you're justifying it by, hey, we're under all this pressure, once in a lifetime opportunity. And all that may be true, and the pressure is like actually a motivator and very helpful, but I don't think I will ever get to go through a ride like Flexport again, or at least mathematically it's unlikely. You know, in retrospect, you wish you just savored every moment of this once in a lifetime ride. You know, maybe that's just sort of how you have to rationalize it because in the moment that stress does drive you, and that stress does drive you to work probably more than you ever would otherwise. So I actually don't know what the right— I don't know if I actually could have enjoyed it more.

That's kind of what I was actually scratching at is like when you're in it, it's impossible to not just see the opportunity as a highly ambitious person that hates to lose, like you mentioned earlier, and not want to take advantage of it every second of every day. And obviously there's repercussions to that. And I think it's especially easy to say, and obviously I've had very many successful people reflecting back on their success say similar things. It's like when you have nothing, generally speaking, like you are way more desperate. Like when you look back, obviously that desperation has changed.

Most of the time I was CRO of Flexport, I had literally $0. I mean, yeah, because living in Texas was expensive. I had young children. Every month, whatever came in went out. And that is an incredibly motivating way to live your life. I mean, there's a stat, I have no idea if it's true, but people claim that baseball players in the year after they have their first child, their batting average goes way up. Because like all of a sudden they need it to work. When you have nothing, like you said, you really need it to work.

Yeah. When I first started in sales, my dad always used to tell me, go buy a car that you can't afford. It's a different approach, I guess. And you had nothing to fall back on. Like you didn't even have a degree. Like ultimately, did you make it through Vassar?

No, no. I took one semester of mostly philosophy and physics classes, the two things I really like. My grades were pretty good, you know, thankfully. But I felt like deep in my soul that I was not in the right place at the right time and took off. But no, I did not have much to fall back on. I've never felt like I had much to fall back on, and I do think it's been helpful.

When you took off from Vassar, where'd you go?

I went back to Ohio briefly. My father was born in 1931, so 1931 was a very different time. When he was 8 years old, or I guess 10 years old, his job was to run around Boston, Massachusetts all night. So he stayed out all night smoking cigarettes, 10 years old. Writing down every airplane he saw in the sky, because it was World War II. So he had dementia by this point, so this is now, this is way past World War II, this is 2003, 2004. He has dementia, so I come back from Vassar, try to figure out what's going on, realize it's like pretty bad, and I'm not at all mature enough to deal with it, and so I embrace Buddhism. It's like, you know, like a lot of people embrace some sort of religion when their life gets difficult. In my case, it was Buddhism, which Buddhism is a religion that lets you pretend it's a philosophy, and maybe it is a philosophy, I'm not at all the expert here, but it's like if you're not a religious person and you desperately need to find God, it's sort of a nice on-ramp to it. So like, just for anybody out there, maybe this is a good way to find some sort of religion. In my case though, that's what I embraced, and I went to India, and I volunteered, and I meditated, and I got kicked out of the volunteer program, and wandered around, and you know, just ultimately did the thing that I think a lot of people do at that point in their life, where they try to find out what matters to them, what they value. And then it became clear that it was time to come home and we had to take care of sort of the end of things with my dad. And then I just started to, I started working. I felt this incredible impulse to go to California. I just felt like if there was one place that was going to accept a person with no degree and a lot of energy, it was going to be like the Bay Area of California, Silicon Valley, baby. And so I really, I came here with nothing and I just, you know, continued to sort of work my way into lucky situations. But yes, that's how it started.

I have heard from your team that you describe yourself as an outside dog, not an inside dog. Can you explain that?

It's so funny. So Roy Bahat from Bloomberg Beta, who I had breakfast with this morning— thanks for breakfast, Roy— he literally said this to me this morning. He said, you know, when you figure out what you're going to do next, just be aware, like, you are an outside dog. You're not an inside dog. Don't take an inside dog role. And I think what he means by that is if I feel truly compelled to do something, I have to do it. I don't really have a choice in the matter. And I think within the context of a large organization, you can't think that way and you can't act that way. You've got to be a part of this larger organism. In the case of being CRO of Flexport, I really believe great CROs are on the road. Great CROs are in front of their customer. They're sitting next to their reps. They're in the shit, right? If you spend too much time in the office as a CRO, And I don't mean like go off on your own. I mean, go off with your teams, spend every waking minute in front of customers with the people who work with you. If you aren't doing that, you'll lose the team. And whether it takes 6 months or 6 years, I don't know. But eventually the team will no longer believe that you can do the thing that they can do. And if the people who work with you don't believe that, why would they want to work for somebody who couldn't even do the thing they can do?

When you were in San Francisco, how did you find Flexport?

I met Ryan at Dubose Park.

Ryan is the founder.

Ryan Peterson.

Dubose Park is the park in the Mission.

Yeah, Dubose Park is a park near the Mission. It's like a dog park. I saw Ryan wearing a YC hoodie, which his— it was actually his brother's. His brother, shout out David Peterson, another amazing founder, founder of BuildZoom, among like a number of other companies. He was wearing his brother's hoodie. We both had giant dogs. Our dogs were playing. I just said, what's up? I was leading sales at that point for Hazeapp. Maybe URX, I don't remember. Leading sales for one of them. I said, hey, I work for a YC company, you're wearing a YC hoodie, what's up, man? And it was like we fell in love. Like truly, it was like a heterosexual love story where he was working on this idea that felt bigger than any idea someone had told me about. And Ryan was one of the first founders I'd ever met who'd made any money. And I don't mean like paper wealth, and this is back in 2010. This is before a lot of the great companies had gotten liquid. Ryan was making real money. About a year, and it was— I got fired 200 feet from here, literally. And I was kind of fat then too, so for those of you out there, if you're gonna get fired, don't ride your bike to work. There's no lower moment in a man's life than getting fired and then having to get on a bicycle and bicycle your way away from your office as your coworkers look out at you. That happened to me literally like 100 feet from where Joe and I are recording this, and I called Ryan from the bicycle. Like literally from the bicycle, like 200 feet from here. I said, hey man, it's over for me at URX. I either have to go like do something else seriously or it's time for me to join you. And at that point he was still finalizing some of the licensing and he was like, look, I don't even know if we're ready to start selling. I think we legally can. I don't know if we're even ready to execute the service, but fine, I'll hire you. And he hired me as a test. And then a month later he said, okay, fine, we'll do this.

And then how long from when he hired you to when you closed the first deal?

Fast. Fast, fast, fast.

Like you knew it was on?

Dude, I knew with such clarity that this was like the opportunity of my life. I like basically went on a vision quest in between him offering me the job and me starting. I went on like a crazy vision quest on my own in the woods of Tahoe and just spent like a full day alone visualizing this whole thing. From what we were gonna do on day one through building the whole company, what it was gonna look like, what it was gonna feel like, how scary it was gonna be. I knew. I just fucking knew this was the one. And then we just went at it. Yeah.

And how long from the first deal to when you hired somebody?

I hired Justin Shafer, who you know, really quickly. When we turned on sales, like when we started actually trying to sell things at Flexport, it was immediately clear to me that our list was endless and that if we were willing to work through the list aggressively enough, even if your conversion rate's super low, if your market's this big and you're willing to work hard, you can generate a tremendous number of leads and opportunities. And so like very quickly my day was jammed and that's when it was time to, you know, hire a first seller. And again, like these serendipitous things just happen. A founder who I've literally not spoken to since, I haven't heard anything about since, God bless him, I hope he's doing well. He just happened to send this note like, hey, had this guy apply for my company. I don't think he's really a fit for us. He was kind of being condescending about it. But, you know, he's from logistics. I think he might be good for you. Justin's an amazing guy. He'd been basically like whatever the degree before you become an MLB player, like AAA or AA. I think AAA.

Yeah.

He'd made it to AAA with the Mets, and then he destroyed his shoulder. And his, by the way, his older brother's like still a great pitcher. Genetically, they're so close, but Justin just didn't quite have good enough tendons. Fortunately for me that this is the case. So Justin had ruined his shoulder. He'd gotten a job for a company called Worldwide Express. Worldwide Express, basically UPS has such a good business that the bottom like billion or so of their revenue, they won't even sell themselves. They're just like, look, we can't sell this many small customers, we're gonna let partners basically own the bottom long tail of UPS business. Worldwide Express is a massive reseller of UPS service. Justin was hired to do door-to-door sales for them. He was knocking on warehouse doors, selling people parcel service rather. When we met him, he was a very non-traditional first hire. He'd been doing sales for a year. It was not necessarily the most rational first person to hire, but when you meet him, you just can't help but want to spend time with this guy. He's like so coachable and he's such an athlete in his personality type that it was just obvious that whatever pace Flexport put up, Justin was going to run with us. And so I think I hired him, I don't know, within 2 or 3 months of starting.

So he told me about this story and he told me that some random guy named Ben calls him from this random company named Flexport. And he had either accepted or was in the throes of like a pretty serious job that he was going into or something like that.

They had offered him some huge promotion. That's exactly what it is. They were giving him a branch.

They were like, oh yeah, to open an LA office. Like this was the break of his career. And he said he had a 10-minute phone call with you and he hung up and he looked at his significant other and he said, well, I think I'm going to this company called Flexport.

That's so nice. Yeah, I love Justin.

What did you say to him?

I think I told him the truth. I told this to a lot of people.

You just tried to communicate your energy for the opportunity.

I just said, look, I think this is the one. I think if you put yourself into this one, it will actually change your life. I said this to a lot of people over the years, and for like everybody who, who put in the work, it ended up being, I think, true. This company, it radiated for everybody who put the work in. This was, this one was gonna be worth it.

Do you ever think about the extra pressure that puts on you in the sense that now it's not just your career, but it's also the promise that you make to others in their career with their families that they came because of what you said? Doesn't that ratchet things up a little bit?

You know, I actually think it's a hack. The only organizations I've ever really run were growth organizations, but I assume this is the case for every org. If you do this math for everybody on your team where you're just like, look, what would it take for the next 4 years to change your life? Like whether you're an SDR, whether you're VP sales, like what would we have to do together here for the next 4 years to just change the trajectory of your life? And then you figure out a plan to do that together. And you do that for everybody on your team. That's how you build a winning team. There's no magic to it. It's just you run that process with everybody and you earnestly try to deliver on the promise when you agree on it. And then if it doesn't work out, it's a sad thing. When it doesn't work out with a seller, I think there's like this, there's this notion with sales leaders that you're supposed to be super tough and you got to cut fast. And it's all true. Like when someone doesn't work, you know, within the first hour, generally. When you sit in a meeting with someone and you don't feel good in your body sitting next to them, You know it's not gonna work. But that should make you sad. It should make you feel like you fucked up deeply, that you brought this person into your organization, and you've gotta help them find a way out with some honor and dignity. And the people that are gonna stay, you owe it to them to try to change their life the same way the business, if it succeeds, will change your life. And obviously the orders of magnitude aren't always gonna be the same, but I just found that was the way that I was the most engaged, and like the way that people actually felt the most connected to what we were doing.

When you started, there was what, $2 million, sub-$2 million of revenue?

How much? Way less. Way less. No, it was hundreds of thousands of dollars a year. And as you alluded to, the way Flexport revenue works, because we are a services business, so like 2021, we did $3.3 billion in top line. Freight forwarding in general is about a 20% take rate business. So, you know, in our case, our take rate was a little bit lower last year, but like roughly 20% take rate, $3.3 billion in top line.

Whereas a great software business could have like a 90% take rate. Right.

So it's the equivalent. If you're trying to compare apples to apples, you would compare our net rev.

Yeah.

So like, let's say $500 million a year of net rev. That's the equivalent size software business. When I joined, it was hundreds of thousands a year of top line. So like, like you're saying, $10. So like, yeah, so like tens of thousands a year of software rev equivalent.

And then from that point to your end of year 1, how quickly are things going at this point?

You know, I think we did $2 million in 2014 and then 10xed it the next year and then 5xed it the year after and then 5xed it. You know, it's each year just felt like its own journey in a sense that year one we were figuring out the motion. We were onboarding customers that candidly, many of them today, like we wouldn't even allow them to sign up for the service because they were just so small. They needed so much help. In many cases, they were one-time shippers. It was someone testing out a new business. Like, at our scale now, it's just really hard for us to serve the biggest companies in the world and also every first-time shipper. But we started at the bottom. We treated everybody like they were gonna be a whale. And in some cases, we were fortunate and these companies grew with us. When things really changed is when we figured out the mid-market. So when I mentioned we have like a toilet importer who spent $30 or $40 million a year with us, it turns out there's a lot of those companies out there. Out there. And that was the big unlock when we figured out, okay, there's a mid-market customer who can spend like in a traditional software sale, like a mega enterprise, and it has a 6-month sales cycle. And when we figured that out, we basically created what we call the gold list. We're like, look, there's a couple thousand companies that are exactly— they are our Goldilocks perfect fit companies. We are going to dedicate everything we have to onboarding this list. And that's when the growth got like insane.

And for those first couple of years, like from what I've heard 3 or 4 years as the CRO with a team that's now growing pretty consistently, you're still out in the field.

Oh, yeah.

Is that right?

I was in the field until my last day as CRO.

And I guess the reason that I say this is, obviously, again, the growth is incredible. That's hard. Did you have a wife?

Yeah, God bless her. So my wife, the first 2 years we had a kid, basically raised our daughter alone.

You were not there.

I was there on the weekends. On the weekends I was asleep because during the week, the play we would run, which I highly recommend— I mean, maybe not at the same pace, but I do think this is an incredibly effective way to spend your time if you have a large distributed sales org. You go to a city, you spend the day with your team in front of customers, you spend that night taking that customer out, you spend the next day in the office with that team working on whatever that office needs to work on. That night you take the team out for dinner. So you're able to accomplish customer-facing and internal-facing so much in that 48-hour block. But in our case, we had offices pretty quickly in San Francisco, LA, New York, Chicago, and we just kept opening offices because our customers wanted us to be local. Transportation is frankly a hyper-local business. There's different rules to even pull a container out of the Port of Oakland versus the Port of Long Beach versus the Port of Newark. Your customer needs to believe you have your hooks into all these things. The only way that we felt like we could ramp up our team was to be there physically with them. And so you were talking about Justin Shafer earlier. You know, Justin, I think, adopted this mentality and he grew more AEs, you know, account executive, individual contributor salespeople. When I say grew, I mean he hired and then got them to basically the ability to hit their quota independently. He grew more AEs than anybody else in the history of the company because he was willing to go on the road. When he'd hire somebody new, They would go to every meeting together around their whole territory for months.

He told me a crazy story about when you were trying to figure out the upmarket, when you went to Florida and crossed Alligator Alley. Do you know what I'm talking about?

Yeah, he— Justin got some sort of horrible virus on that trip and was vomiting outside of the meetings.

Yeah, like you did 2 on one side of Florida, you took the red-eye, got there at 5 in the morning, took 2 on one side of Florida, 2 on the other side of Florida.

I didn't— I'm bad at geography. I didn't realize Florida's actually a big state.

And then you flew back in time for dinner.

Yeah.

First of all, like, doesn't this burn you out? I just don't know how else to ask you. Like, easy to say in hindsight, it's what we had to do. Easy to say like, this is a good playbook, 48 hours. But like doing that, actually doing that is so hard. And like, yeah, what are you sacrificing? Like obviously you put on weight to your point, like your family, they're no joke, huh?

No, I mean, I think the only way you can do it long-term, a lot of standup comedians won't work Sundays because they're like, look, Thursday through Saturday, that's when we earn our living. Sunday through Wednesday, I'm home with the family. There's a few like famous standups who've said this is their model. I think you've gotta figure out something similar. And the way that I sort of run my life now is I kind of work in these sprints. Like this week I'm in San Francisco, my family's back in Wyoming, I'm grinding it out. I'm in meetings all day, every day, go down to L.A. Friday, work until Saturday morning, basically, and then fly home and then I'll be with my family for a few days. Then I'm going to go to D.C. and grind it out for 3 days. And for me, this works super well where I feel like I can just work so much harder on those few days where I'm sort of free to do my own thing. And then when I'm home, I can be way more present with them and we can do things that are a little more off the grid.

I actually aspire to be more like that. Naval talks about how humans are meant to work like lions. We hunt and then we chill and then we hunt again. And I think I do actually do sprints. And generally my sprints happen when I'm traveling. Like generally when I'm on the road is where I can hunt like a lion.

Your brain switches, your brain goes, you're going, you're, you feel like you're a hunter.

Did your wife get it?

Yeah. I mean, it wasn't easy. You know, her mom lived with us for 3 years during this time.

And you were making money to your point.

No, I wasn't making the money yet. That's the other thing. If somebody wants to buy secondary in your company, you almost certainly shouldn't sell it to them. That's one of the great paradoxes of building a company. It's almost impossible to get liquidity, and if you can get it, you shouldn't take it because for the most part, people don't want to buy secondary in startups, even good ones. So if you have the opportunity to take liquidity, even if it's really tempting and it changes your life, just know you're doing it most likely at a price you're going to regret massively in the future. So I put it off as long as I could, I could just feel that the stock was not done appreciating. But at some point you just— I had to start taking a little bit.

For the family.

Because I had to show like there's a purpose to this. Yeah.

And to reward the sacrifice that your family is making, right? At least in some small part.

We were living in 900 square feet with 2 kids. It's crazy.

Crazy. She might be the star of this show after all.

She's very disciplined. And without— yeah, without her, this would not have been possible.

Let me ask you this. As you look back and this is how I feel, so I'm curious if you feel the same way. Do you remember the 5Xs and the 4Xs and the 8Xs and this insane, insane growth? Or is it more vivid in your memory doing the Florida trips and doing the team events and doing the 48 hours with the team?

I'm very much a score takes care of itself kind of guy. One of the things I need as a sales leader is to have great counterparts who are more metrics-driven and analytical because I generally believe if you hire great people, you understand how much activity those people need to undertake every day, they're doing it and people are happy and your playbook is a good one, you're gonna hit the goal. You know, whether you do 4x or 6x, you don't really have control over it. Like you, you make as good a list as you can, you hire the best people you can, you motivate them to work as hard as they can, and then you tweak the playbook as you get feedback from the team. That's literally all you can do. And so, no, I just feel very fortunate that we were in these positions where the growth was coming. But no, I couldn't tell you like this year we did this multiple, this year we did that multiple. I have no idea.

Is there anything you would have done differently to make sure you're filling your own cup during those times? Like, obviously exercise, exercise, exercise. So Mark Roberge, you know who Mark is? Employee 3 at HubSpot, founding CEO.

Of course. Yeah, yeah, yeah.

So he's probably— I'm sure he's at Saastr. Actually, I know he's at Saastr because I'm seeing him tomorrow. Very similar story. A family in Boston, absolutely grinding it out and like unlimited leads, you know, like the same story. And he would leave the office every day, I think at 2 o'clock and go get a run in for 1 hour every day.

Smart.

Like every single day. And I think he would leave at 3:30 on Wednesdays and Fridays to go put his kids to bed. And then he would get, you know, his extra 6 hours from 9 to 1, whatever it is.

This is a smarter person than me.

But that's what you would have done. I would have done exercise is the thing you would have absolutely dialed into.

Yeah. And for me, it's turned out to just be lifting weights, which I had never done before the last couple of years. I've gotten super into it. The idea that I did Flexport without having a physical outlet for the stress, it's now obvious, like, yes, of course you got super fat without an outlet for that level of stress. Something bad is going to happen to your body.

When times did get tough, when you lose a deal or whatever, how did you put on a brave face for the team?

I didn't always. There's one moment where two AEs were fighting over an opportunity. This is like before we had clearly defined territories, and I sort of lost my temper. I was like, look guys, do you not understand the scope of what we're doing here? This is a generational business. And you guys are fucking around over a lead. Like, what the fuck are we doing? And I think, again, like, maybe that was the right thing for those folks to hear in that moment. But I don't like remembering myself in that way where I was like sort of out of control in my— in terms of temperament. But yeah, that's probably the one thing I would change.

Makes sense. How did you scale yourself ahead of this company? Meaning one of the challenges that I think is the hardest thing to accomplish at high-growth companies companies is that they're high growth, meaning that this company is growing exponentially. You grow linearly. How did you stay ahead of the curve so that the CEO or the board didn't just top you?

Yeah, I mean, it's a constant battle, right? If you were in your first sort of big-time role, just know you're earning it every day until your last day, especially when things are working. It's one of those things that sort of counter to what you would expect, that the more a company is working and the more it's clear that it sort of is a once-in-a-generation opportunity, the more likely it is you're going to get replaced.

Because the better talent that the company can recruit. Totally.

All of a sudden, the best people in the world will take the job. And all of a sudden, like all the folks who are on the cap table are really invested in this thing working.

And they know all the best people. You think Founders Fund didn't know the best people?

100%.

Yeah.

And so you just sort of have to embrace that. I think the thing that allowed me to survive specifically And it only was possible because I spent that year with Ryan before he hired me. We had enough trust between us, like, that he at least trusted me as an intellectual sparring partner on the business. He may not have trusted me as a sales leader, but like, he at least trusted me enough as someone that he could talk about any aspect of the strategy of the business and I could engage with him. And that level of trust allowed me to be less afraid of losing everything. Even if I wasn't going to be his sales leader anymore, the time we spent together working on the business was valuable enough in its own right that I could survive and that I wasn't going to lose all the stock and whatever else. And that then allowed me to just sort of go, okay, in every situation I'm going to do what's best for Flexport. If that means hiring people that are threatening to me, I'm going to do it. You know, if that means having to go tell Ryan or tell the executive team, hey, I need more mentors, I need you to ask our LPs or our cap table, ask them to introduce other sales leaders. Like I just had to do vulnerable shit constantly to get better. But ultimately it's because I felt like Ryan wasn't going to kick me to the street if I wasn't going to be a sales leader anymore.

Yeah, there's implicit trust there.

Yeah.

Can you tell the story, speaking of mentors and people that you went to go see, about when you went to go see Parker at Zenefits? Yeah. Parker Conrad, now CEO of KP Company, Rippling. Parker, by the way, one of the— turns out one of the greatest, I think, CEOs we're ever going to see in Silicon Valley. Do you agree with that?

I think Parker changed my life in like the 2 hours I spent with him. I don't even know if he would remember this meeting. It was sort of peak Zenefits. It was right when David Sacks was coming in, right when like shit was getting real at Zenefits. And he still, because of his friendship with Ryan, our founder, he took the time and hung out with, he invited us to his office, which is down the street, and he walked us through what Zenefits was doing, what he and Matt Epstein and Sam Blond figured out in terms of high-volume outbound. I knew what outbound was before this conversation, but Parker is the first person who broke down sales for me in a way that the whole thing just felt like you could put your arms around it, where it was sales wasn't this thing you hoped for an outcome. Sales was just a series of processes. Sales was a series of processes that if you executed a good playbook for each of them, the score would take care of itself and your reps would have more meetings than they could possibly handle. You know, Parker is, he's one of these guys who has such intense energy and such a unique demeanor that you just can't help but sort of like be captivated and like almost want to take notes as he's talking. And we left his office knowing like in our bones that if you built an outbound machine, you had total control over your destiny. And that was something that hadn't clicked for me before where it was like, I kind of believed in marketing, I kind of believed you could get people to sign up. And Parker made us realize, Oh sure, that's nice if that happens, but you can actually just go get all your customers. Like you can just make a plan and go get every customer on earth that matters to you. And if you're really good, you can make a list and stack rank it and go get them in order. And that was like life-changing.

And to be clear, Flexport's business was minimum 90% outbound.

Minimum.

Yeah. Like even today.

Unless something goes catastrophically wrong in someone's supply chain, generally they're not calling brand new vendors trying to bring you in. Conversely to that, though, our customer is generally not contracted with someone else in a way that is ironclad.

Can I ask your perspective on all this PLG stuff? Yeah, very curious what you think. We are starting to see more counterexamples to PLG than I think people are a little comfortable with, if I'm being honest. Meaning this company called Wiz, cloud security company, went to $100 million in 18 months. Yeah, fastest anyone's ever done it in SaaS like that. All outbound, all outbound. You know, you look at the Riplings and the Zenefits and stuff, you look at Flexport.

Ramp.

Ramp. Yeah.

Ramp is generating more opportunities per SDR than any company in history. I don't know that with certainty because I haven't talked to every company. I think it's probably true, though.

So let's unpack this one layer further. And for those in the audience that are uninterested in sales, I'm sorry, but what was the key insight that you took from Parker that day about outbound?

List construction is everything. To this day, Flexport We have a gentleman named Brian Lee who went to Dartmouth and I assume got very close to a perfect score on the SATs, whose full-time job is managing the list and managing the territories and assignment of the list. If you have a list that is organized, enriched, and by enriched I mean it has all the data you would need to actually attack that, that customer, the names, the phone numbers, the email addresses, ideally an org chart, whatever you can get. If you build a list and you invest in it, it will make everything that you do after that list construction better and easier, from the phone calls that your sales development reps have to make to when your AEs have to close deals. All of it will be easier if you invest in list construction.

And there is a lot of traditional thinking that says, oh, well, the BDRs or the inside sales reps or the reps can create these lists.

Absolutely not.

Yeah.

So what we figured out is the rep should have the ability to find net new leads. And if they add it to the database, if we don't have it in our database, the rep can add it themselves. Otherwise though, we are assigning the list. It is our job to arm you with a list that tells you in order who you should go after and why. And sure, like you're smart, you're probably smarter than our system. You can reorder the list. You can go look. I actually think these are the best 10 that I was assigned this month. But ultimately, the amount of work it takes to build the list, get it enriched with contact information, and organize it, if you're asking your reps to do it individually, you're taking 25% of your time. And by the way, you're introducing tons of chaos into your system.

Now, would it be fair to say that this works uniquely well in lower ACV, bigger patch systems? Meaning like, if you have unlimited TAM, whereas like there's just way more accounts that you can go after. It's a higher velocity motion.

Yeah, 100%. But I actually think even if your list is small, you just can't run the machine as hot. You should still run the machine. You just can't push it the way you can if your list is as big as ours.

How would leaders at Flexport earn more equity?

You know, the—

I was fascinated when I heard this.

And you mean in the sales org specifically?

I mean in the sales org, sales managers.

So like the way that we figured out was most effective to compensate sales leaders in terms of equity was for every net new seller they added to their team. So when someone— you hired a new seller and you ramped that person, because what we figured out is like an individual at Flexport can be insanely productive because one individual can have multiple account managers paired with them. So like, you know, one individual might drive 10 times more revenue than the next best rep in the company. And so it's incredibly valuable. Each time we built a new rep who was capable of hitting quota, you made the business dramatically better. So we said, okay, what would it take for our sales leaders to care as much about creating net new reps as they do about hitting their number? Because like hitting your number is pretty important. If you don't hit your number, you get fired. So how do we get you to care as much about cultivating talent as you do about hitting your number. And the only way we figured out is a really generous equity kicker every time one of these new reps hits their annual first-year quota. And like Justin Shafer, he did it more than anybody else. I won't sum it up on air. I won't embarrass the guy, but like he earned a life-changing amount of money by ramping new sellers in a way that I don't think he would have ever dedicated the time to do if we didn't have this equity plan.

That's not that complicated. Like, that's actually like pretty smart. I don't know how else to say that.

People don't like giving sellers equity because they feel like they're already, quote unquote, overcompensated in terms of cash. And I think it's one of the biggest mistakes sales orgs make at all stages, like especially early stage companies in particular where you don't have a lot of money. Your sales leader can afford to take a hit for a year on cash. Make them. You don't know how to pay them yet. You don't know how much your business can do in revenue. You don't know what your quotas should be. If you hire a sales leader early on in a company's life and you try to compensate them in dollars, you have misaligned incentives from day one. The only thing that I think makes sense for your core team is to have a significant equity component. Otherwise, you just can't trust them to make decisions on a timescale that's any longer than whatever their quota is based on.

How often are you burning the system down and rebuilding it? Meaning, like, in those crazy days, how much are territories changing? How frustrating is— how much work is it to build a system and then literally by the time you've built it and you've implemented it, a quarter later, you're like, oh God. Now, obviously a caviar problem.

Yeah.

But how often do you have to feel like you have to rebuild the company from the ground up again?

I think we were really fortunate that the core motion of build the list and attack the list in a specific fashion that worked to this day. Like if you look at the text of our phone conversations in 2022, I'm sure they're more sophisticated. Our sellers are much, much better armed than they were in 2014. But the core motion of get all your data in one place by doing all of your transactional shipping with this company, that play still works. What didn't work though, and what was so hard is comp plans, territories. When you're growing as fast as we were, you're like a different company every single year. And the quotas have to go up by so much every year because your brand is getting better. People's books of business are growing organically. But communicating that to people is so brutal, especially because, you know, we're all experiencing hypergrowth for the first time. The quotas feel impossible every single year by definition. This was all new for me as a CRO. It was new for most of our sellers 'cause they were mostly first-time or second-time AEs. Just having to deal with that amount of change in quota size, in how the territories were aligned, and what was expected of people every year, it's a brutal change management project. And I think if I could to go back, I would've overinvested in sales ops. I would've opted in to make less money personally and had a larger sales ops budget just to make these changes more palatable for the team.

Yeah, that makes total sense. I've heard you're a bit of a talent spotter. I bet you that what a lot of people are gonna think when they listen to this, especially founders, is how do I find the next Ben?

Yeah.

Let's assume it's not you, but someone that sure looks and feels a lot like you and is maybe the skinny version of you. Like, what? What are you looking for? What should they be looking for?

For those of you who are listening, your host does an incredible amount of research before he records these. All the folks he talked to from the Flexport sales org have something in common, which is this genuine curiosity about the world. Sales gets fucking boring if you are not a genuinely curious person. If you aren't actually curious, like, hey, how does a toilet company work? Hey, how are sweatpants made? If you don't care about the answers to these questions, you're going to have to find all kinds of funky ways to motivate yourself to be a good seller. If you can be intrinsically motivated by understanding how the world works, one, your customer will relate to it. They will go, oh, this person is excited to be in my office learning from me. And that's kind of a joyful experience for a person who doesn't get to feel that way often in their job. And if you can do that day in, day out, as you know, you interviewed Justin, you interviewed Marianne. There's one named Julie Harris who embodies this. There's sort of an unlimited well of potential because you don't get tired of going on the road, you don't get tired of going into people's offices, you don't get tired of calling them a second, third, fourth time, 'cause you've tapped into something more genuine than just, hey, I'm trying to sell you some shit. And whether or not you start in this mentality or you sort of Jedi mind trick yourself into it, I don't know that it matters, but if you can find a way to be intrinsically curious about the world, in a way that's directed in your sales job. I think it's the only path to durable success, and I think it's the number one trait I would look for. It's just like a pathological level of curiosity.

I couldn't agree more. I have a very strong belief that the underpinning of improvement is curiosity. And if you cannot be curious, both curious about the outside world, but I actually think equally as important, curious about yourself, that you can't cultivate the self-awareness that you need. You can't cultivate the learnings from the outside world in order to actually improve. And I actually think that the reason that all those people, including yourself, that you just mentioned were so good is because they get better faster.

Totally.

And I think the only reason they get better faster is cuz they're curious about everything, including themselves.

It's so interesting you say that cuz Justin used to talk about, you know, his baseball career. There's nothing that's— you're more— where you're more scrutinized than being an athlete. Like you are literally— they're measuring you physically. They're measuring how tall you are, how much you weigh, how fast you can throw, how fast you can run to a base. And Justin got to a point where he was excited by that. He was excited by the idea that he didn't know how fast he could throw. He didn't know what he was capable of. He didn't know how he compared to his peers. But just the idea that he was going to get to compete and be a part of it, that's what drove him. And getting to see that play out in the workplace, obviously very different than on a baseball team, but I think it's the same vibe.

It's funny because everybody, when I talk to them, says that you're so natural. You're so natural as a salesperson. The more I sit with you, the more I believe that you, similar to me, have a natural reservoir of energy. However, I don't think you're actually that natural. I think you just get better faster than most people, and I think you have the energy to just improve. I really do. And I think you just have more energy that's sustained over a longer period of time. And I bet you that this version of Ben does not resemble the Ben of 2014. Now I think that there's— everyone would say they still recognize you. You still have the same energy. I just think you kept getting better faster than most people, which is why on your resume you can take Flexport from zero to a billion without getting topped. Most people do not have that. Nobody has that. Maybe Chris Degnan from Snowflake. There's nobody that has that. And I think it's because you improve more quickly. Is that fair? Like, do you think that's a fair observation?

I think it's totally fair. Um, I'm very into stand-up comedy, so it's my second stand-up analogy during this podcast. When you listen to interviews with stand-ups and you show them their tape from the beginnings of their career, they're mortified. Like, they feel physically sick when they see themselves perform. When I think about everything I was doing early in my career as a seller, as a— and particularly as a sales leader, like, as a seller, I always felt like I was extremely natural. Like, it was just, you know, I was almost like on a mission from God to do this job. But becoming a sales leader and having to balance the egocentric role of being a seller, which is like, hey, this is my show, I'm the actor in this movie, to being something that's more behind the scenes, just so you're more of an enabler. That transition is where I had to like basically destroy myself and rebuild.

I completely get it and I totally agree and I feel the same way. My favorite definition of sales is that it's the transfer of enthusiasm from one person to another. I don't think that you or I have difficulty transferring our enthusiasm. I do think that is intrinsic. Yeah, I do think all of the other stuff is very much learned. It's very much learned.

I think it can be hard if you have that talent. It's why so many great sellers can't make the leap. If your value as an individual comes from, as you said, like giving other people enthusiasm, it's very addictive. And sometimes you don't want to give that feeling away to your team. And I think in my case, like, that would be a fair criticism of me in my early years where I wanted to stay in the sale as like an individual for too long, to the point where, like, for the first 2, 3 years of Flexport, I was still on the scoreboard, like, as an individual. Like, my name was on there with deals, which I would never do again.

There is a tweet that you put out. I don't know when it was. It says, everyone excellent at their craft starts from a place of deep insecurity. Can you explain that? It's like a theory that you have.

Michael Phelps is maybe sort of not an example of this where like, yes, he is just genetically meant to be a swimmer. But I think for most of us who are just like genetically average or slightly above, slightly below, whatever it may be, so much of your success is just built around how much you're willing to do and how much you're willing to change yourself. And like acknowledging the fact that we all start out kind of shitty. That's the reality of being a human. We start off unskilled. It takes us years to learn to speak or walk or do anything. And then to be really good at any of those things takes you 10 years. We are a slow burning firework. If you're willing to put the work in, the outcome can be spectacular, but you just have to acknowledge the fact that you are not going to be good at anything when you start doing it. If you don't embrace that idea and if you don't lean into it, you're almost certainly lying to yourself, and then it just becomes impossible to get better at anything. At least that's what I've experienced.

Do you ever have the feeling like when everybody is telling you you're doing a great job, the way that I experience it is, A, it's almost like I can't listen to it. Like I have to just compartmentalize that and immediately find, I can't hear this. What is the thing that we could do better? That's number one. And number two, when I'm not hearing that, even if I am, I have this almost fear. It's not that I'm going to get fired, but that I'm going to get caught. Like I'm going to get busted for like not knowing my stuff. On a given day in a given conversation. And when I reflect back on a conversation that I had earlier, I just think, man, she knows, he knows, you know, like they're going to find out. Do you ever experience that?

Yeah. I mean, I think you're describing imposter syndrome, right? To some degree. Oh yeah. Yeah.

I mean, imposter syndrome is just one variance of insecurity.

Yeah. I met with literally, like, I'm not being hyperbolic. I think I met with over 100 sales leaders in the first 3 years of Flexport. Sometimes under the guise of I was interviewing them, sometimes I was reaching out to learn, but I literally think I asked 100 people, how do you run a sales org? Do you know how embarrassing that is if you're already a CRO to like reach out to other adults and say, how do you do your job from beginning to end? Sometimes I would be blown away and sometimes I would go, okay, this is, you know, you get this out of any book, whatever. But when you synthesize 100 of those meetings, you've actually learned an incredible amount. But every one of them was embarrassing. Like, I was embarrassed 100 times asking other sales leaders how to do the job I already had.

You should have started a podcast. You could just hide under the guise of a podcast. I could have coached you up.

It was too early, man. I didn't know how lucrative these things were.

I have a couple more questions, then I'll get you out of here. On the fund stuff, running the Flexport Fund, I get hit up by so many CROs Hey, Juben, I'm ready to come to venture. Is Kleiner hiring? What can we do?

Yeah.

Curious from your perspective, is it what you thought and do you like it less or more than operating?

We have to be really honest with ourselves about what the best part of venture is. And it's that, first of all, the model of 2 and 20 is unbelievable. It's unparalleled. I mean, unless you're a hedge fund and you're like, like some of these great hedge funds, by the way.

2% management fees, 20% carries. Yes.

2% management, 20% carry.

20% carry for the audience, meaning equity in the business.

Yes. So effectively, let's say you have a billion-dollar venture fund. On 2 and 20, you effectively get 2% of that fund every year as a fee. So you get $20 million a year as a fee. That's used to operate your fund. But a lot, you know, a lot of people hear 2 and 20 and they think that fee is one time. No, no, no. That fee is every year for the life of the fund. And then the 20 refers to— so you have a billion dollars at work. Once you've paid back your investor's initial billion, it's as if you put $200 million at work and you basically— so if you 5x the fund, so let's say you 5x a billion dollars, you pay back your investors' billion first, then you have $4 billion, that's pure profit. You literally keep 20% of that, of that probable you've created. Now, 5xing a large sum of money is very hard, but effectively, you know, this is a system has been designed where tails you win, heads you win. Like there's just no real way to lose as a VC assuming you're, following the law, you're being honorable, you're treating your LPs well, especially with the returns of the last 20 years where the returns were just astronomically good for a lot of folks, it feels like a rational business to be in. And it feels like, unlike as a CRO where you're so concentrated, where it's just like you literally live or die based on the performance of one single company in the universe, it feels like you're more diversified. Having said that, the time to liquidity in venture is so much more brutal than anyone who is a CRO realizes. Most people who want to leave being an operator, they don't understand that even if you crush it, like you absolutely blow it out of the water with your first fund, it's going to be very small. It's going to be a very small amount of money. It's going to take you 5, 7, 10 years to raise an amount of money that you thought you were going to be able to raise on day one, potentially, if you're doing it as an individual. And if you go to— if you go join someone else's fund, All of a sudden then you're doing internal enterprise sales. You're effectively having to sell deals internally. You're trying to figure out what your position is. You're trying to figure out what the fund wants you to be. There's some funds that want people to be really aggressive. There's some funds that expect people to do 1 deal a year, which I think is very hard for operators to get excited about. The actual day-to-day of being a VC, I think for some people, will be very frustrating even though the model is so appealing. The idea that you have a diversified portfolio, the idea that even if it's not your own funding, you're getting a piece of it, that you're benefiting from this really generous structure that is 2 and 20. There's a lot of reasons that people get pulled in. I don't think all of them have really thought through what it means to spend 10, 15, 20 years building an institution in venture. It's, you know, I think you can build a company in 6 years. I really do. I think you can build a company from founding to real valuable outcomes for the founders in 6 years. But I don't think you'll get fully liquid on that company for, 10, 12, 14 years. And so as a venture investor, you've really got to be in this game for two decades. Like if you're not willing to sign up for two decades of work, I think you're going to find that you probably would make more money and be more fulfilled as an operator.

Yeah, I generally agree with you. I'm excited to have this conversation with you in two years. You started in venture like a year ago, like mid-'21, right?

Yeah. Hilarious time.

Yeah. Probably the worst time, admittedly, to start deploying. Going cash.

The absolute worst time imaginable.

Yeah. And so you're probably thinking your first 9 months, how many checks do you think you wrote? 30? 40?

More. More.

You're a genius, right? Like, you are getting marked up. You're probably following Kleiner, Sequoia, Founders Fund, just whatever good name. And you can just use your energy to sell. You can just sell your way onto the cap table.

Totally.

And you're like, I'm good at this. I am good at this.

Yeah, I think we were all aware even during 2021, even as we were investing in these companies, it didn't feel right. Like 2021 felt off.

Yeah.

For those of you who weren't in this mix, companies would raise a full round of venture funding in 2021 in a week. And I don't mean like they would get a commitment in a week. I mean the diligence process, wiring, paperwork, things were happening in 7 days, 10 days. That's not enough time for anybody to do their job. That's not enough time for anyone on the buy side of these transactions to evaluate these companies well. And I think if you look at the 2021 vintage, even of the best venture funds in the world, they all paid higher multiples than they ever have historically, and they are likely going to have lower returns than the rest of their funds. I think I'm very lucky that I got to experience 2021 with a really small amount of money. We were doing mostly $100K checks. We have markup on a lot of the deals. Thankfully, even though we were investing at an expensive moment. I was talking to a friend who has a really massive private equity fund the other day, and he was joking with me that 2021 was the busiest year of his life because he was selling everything that wasn't nailed to the fucking floor. They literally, they divested out of everything where they could find a buyer. He just said, look, even if we were wrong by a degree or two, even if the market had more to run, we knew that these multiples, you know, these multiples on revenue these companies were being valued at, We knew these multiples were historically abnormal to a degree that we had a fiduciary obligation to sell everything that wasn't bolted to the fucking floor.

That's crazy.

And I, you know, he did very well last year. And I think I'm very lucky I got to see the cycle with a small amount of money. If you deployed $1 billion or hundreds of millions of dollars just in 2021 and you don't have time diversity in your fund, it's going to be a long road back. We were also on the Flexport Corp Dev side. There was nothing to acquire for this reason. Everyone was able to raise money at valuations that made them unacquirable. Even if they would have made, been a good fit for Flexport to potentially acquire them, roll in the tech, roll in the team, whatever, it was literally impossible to get any deals done for the, basically, you know, in large part for the last couple years, but really over the last, call it 12 to 18 months. I think we're starting to see the pendulum shift. Like, we're now starting to have top-tier VCs reach out to us proactively. Like, hey, what do you think about this company? Because they're not putting another dollar in.

Uh, last one. Something that has struck me is that when I was talking to Will Urban, who took the CRO role, took the baton from you, you were very gracious in that transition process. And you were very self-aware in the sense that you knew your time was up. Yeah. And you knew your time was up, not necessarily because you lost the Flickr, but because you knew that the company had outgrown you. One of the other things that I just— obviously the news of Flexport of late is that it sounds like Ryan Peterson, the CEO, did a similar thing. Flexport just hired the number 2 or 3 guy at Amazon, the top logistics person maybe in the world, to come be the CEO, and he was very gracious about it. He led the process.

Ryan, to his credit, it started as a COO search, and if you look at Flexport today, The one thing that we've got to make sure we are better than the market at is ops. It's operational cost to serve. And like, we're dramatically better on customer experience. We're dramatically better on customer happiness. Where we are either at parity or even a little bit worse is operational excellence. Ryan brought in the actual best operator on earth, and he did so in a way that, you know, the only way you bring on the best operator on earth is you step down. You don't get Dave Clark to come in as CEO. It's not a thing that happens in this universe ever. So Ryan did what the company needed, which is the one last piece Flexport has to prove is that we can be operationally the best forwarder in the world. He brought in the leader that is most likely to make that outcome happen. In my case, I think it was sort of related to this. Flexport, like, growth is not the issue anymore. There's enough demand for what we do. Our product is really differentiated. Customers are really happy. The market's really fricking big. At some point though, you need a leader who can deliver service, who can actually manage customer expectations across billions a year of turnover, who's seen, in Will's case, like 40 years of this specific market where like, I can't tell the buyer at one of the big hard drive manufacturers, for instance, that I've managed a $300 million a year air freight account before. I can get them to Tesla Export, I can get them to buy in, But they're never going to believe that, that a team that I'm managing is going to be the best in the world at delivering the service of moving $300 million a year of air freight. And I met Will. I actually brought Will in as a consultant because I was trying to level up on the freight forwarding side where it was like we were selling these monster enterprise deals. I was at a point where I just needed to know more about how the operations worked globally and what my customer understood about how air freight works leaving Dubai versus Singapore versus, you know, whatever the Gateway maybe. So we brought Will in as like a subject matter expert. We would spend like days in a meeting room with Will just asking him, hey, how does this work? How does this work? How did XSpiders do this? How did XSpiders do this? Why can you do this air freight product out of this region, not that one? And at some point I just realized, you know what, the person who's gonna operate this business right now comes from this industry. And you know, it just made sense. And so at that moment I went to Ryan and like we were, you know, had the conversation And I was expecting to leave then, candidly. And at that point I was, I was like very ready to go do another CRO role. I just kind of felt like, you know what, I want to go prove I can do this again. And Ryan said, look, you've built a lot of new products here. Just stay on, build new stuff, just keep building. So we built one new product over the last 2 years called Flexport Flow, which was like ultimately one of the reasons Shopify made the investment they did. They put $400 million in about a year ago. That was sort of a thing that me and a guy named Steve Bozisevic incubated to basically deliver goods directly from factory into fulfillment without stopping at a DC in the interim. What that means is basically you're removing a stop along the way for cargo and you're allowing people to route a lot more in real time as goods leave their factory versus having to build stockpiles of inventory and then break it up. So at any rate, built that product. But yeah, my time as CRO was over, or at least I felt like it was, and it was. and I wanted to keep helping Flexport. The only way to make those two things congruous was to just embrace Will and like get super excited about Will, because if I didn't, then I couldn't stay on at all. A friend of mine calls it pissing in the soup. A startup is this magical experience where everyone kind of has to believe and be positive because you're creating new things every day. And if you introduce any negativity into that mix, You are pissing in the soup. You're ruining dinner for everybody. And I just felt like, you know, I'm not going to be that guy. I mean, if I'm going to stay here and I'm going to, I'm going to keep building things, I'm really going to make sure I'm not that guy.

What a great story. And Flexport was lucky to have you and is seemingly in a really great place now. So congratulations, man. That was really special.

Thanks so much for having me, man. I appreciate it.

I always close these things out the same way. The first is I don't think you're hiring, but I imagine the company is hiring.

Oh yeah. If you are an engineer that is looking to work on something that has immense global scale, um, to give you a sense of like the GMV moving through Flexport, it's in the tens of billions. In the coming years will be hundreds of billions of dollars worth of stuff that we are physically responsible for moving. The scale of what we're building, I think, is pretty unique. So if you are an engineer and you're looking for something sort of novel, highly recommend you check out Flexport. But yeah, that's the main thing we're looking for.

Last one, when you hear the word grit, what comes to mind?

Carol S. Dweck, she wrote the book Grit. No, I'm serious, someone gave me that book when I had kids. They gave me the advice that they said, look, the one skill you can actually impart on your children is the ability to persevere and like the ability to not be super bummed out by failure. Everything else is pretty much inborn, but like you're gonna teach your kids what their relationship with failure is gonna be. You can either tell them every time something goes wrong, great, that's awesome, this went wrong, let's dive in and do it again. You can either be that parent, or you can be the parent that goes, oh, fuck, we ruined this, this broke, whatever. How you relate to problems with your kid is going to determine their ability to overcome problems on their own. And I think like that actually made me a more effective just like adult when I realized, oh, I can use the same tricks with myself. But when I think of grit, I mostly think of like how to raise your kids.

Ben Braverman, thank you.

Thank you for having me.

That's it. Thanks for listening. If you're just discovering the podcast, we have a lot more episodes from organizations like Snowflake, Twilio, Slack, LinkedIn, Box, etc. If you want to keep up or support the show, the best way to do so is by following us on Spotify, subscribing on Apple, and leaving a review. Also, we love feedback, so feel free to email us: grit@kleinerperkins.com.