The Exchanges

Q Absolutely. I do want to start, though, today with a slightly macro perspective of a discussion that we've had before where you've stressed the difference between linear and non-linear businesses, but you left me on that cliffhanger. So let's start with that. How do you define linear and nonlinear, and how do they kind of fundamentally differ?

A So I think a nonlinear business tends to have a nonlinear or a binary outcome. Either it works or it doesn't work. The businesses maybe aren't interesting at the small scale, so they could take years to take off, waiting for a lucky break, and then they, but they tend to have a strong network effect. So when they do take off, they accelerate quickly, and examples might include, you know, hit-driven businesses like video games, music, social networks, Some pure marketplaces like eBay and some other ones, maybe like Instagram or Pinterest, which took a few years and then kind of hit and took off. And a linear business, on the other hand, can have a variety of outcomes, can be assessed successful at different scale, different levels of scale. And so that could be things like medical device sales or real estate, or even SAS products that are created and sold. And the way those work is the more energy and time you put into selling this item or creating and selling it, the more business you create. And oftentimes it's a B to B type of business. And so it ends up being fairly linear at first, You put an extra day or effort, you know, an extra hundred calls in, you're going to get some number of customers that buy. And so you can kind of scale the business through hard work. And what we kind of thought was the best of both worlds is what's going to fit us. Cause I always came from a ba…

AI assessment note: “a nonlinear business tends to have a nonlinear or a binary outcome”

Q Before we kind of discuss that kind of culture of experimentation, the final element on fundraising I do want to touch on, we had Anu and Ali from YC Continuity Fund on the show. I'm intrigued, why did you choose YC as the chosen kind of lead series B investor of choice?

A Yeah. So one, Anu and Ali are fantastic. Two, I think we felt like there was a really good opportunity to get kind of the best of two worlds. There's a growth fund, those partners, as well as the organization general has very, very deep ties into many of the growth stage companies across Silicon Valley and across the world. And so we would be able to get a lot of great experience and insights from those companies through the YC network. And the partners have a lot of experience scaling and buildings. They can help us understand that. So we felt like we got that benefit, which is what we needed entering kind of a growth phase. But the DNA of YC is about deeply helping companies succeed. And it's a service mindset. And sort of, as I mentioned, I want to lean into the resources. I want to lean into the investors that we're working with so we can get the most out of them and give our company the best chance at growing. As you mentioned, it's an efficient way of doing it because it's already a group we're working with. And so I felt like because of that DNA that YC has as an incubator and its founding, we could feel that. And I have never worked with a group that this quickly was, you know, so quickly into our relationship with them has done so many proactive things to kind of help us. The Gia, who runs recruiting over there, is fantastic. She's been very hands-on in a couple of maj…

AI assessment note: “there was a really good opportunity to get kind of the best of two worlds”

Q No, I'd love to get the ball rolling, though, by discussing a little bit about you, and tell me, Dan, when you were a little boy, did you always dream of reinventing the world of supply chains, and how did Convoy come about?

A When I was little, I was, well, I appreciated supply chain because it paid me 10 dollars an hour during the summer. I worked, my family had a mom and pop kind of office supply distribution business around the Northwest. And so I worked in the warehouse. I'd pull boxes down from shelves. I'd load vans and small trucks, and then even started doing some driving when I was, you know, later in my teenage years and in college. But that was more, I get paid during the summer, set up money for clothes and going on dates and things like that. Did not think that was going to be my career, but later on did a bunch of things in transportation, actually. I did some work with the Panama Canal, did some work Related to manufacturing and maintenance programs for airlines related to their parts distribution and maintenance. And then ultimately, I was at Amazon, actually, before I started Convoy. And you were asking, kind of, how did this come about? Honestly, I witnessed pretty powerful supply chain transformation happening via Amazon and how that can change industry. And, you know, consumer expectations are going up. Businesses have to react, increasing the flexibility of their supply chain so they can manage inventory costs, get things to the, you know, the right person at the right time as quickly as people expect. Which is, which is pretty fast these days. So we dove in because we thought w…

AI assessment note: “Did not think that was going to be my career, but later on did a bunch of things”

Q Absolutely. I do want to start, though, today with a slightly macro perspective of a discussion that we've had before where you've stressed the difference between linear and non-linear businesses, but you left me on that cliffhanger. So let's start with that. How do you define linear and nonlinear, and how do they kind of fundamentally differ?

A So I think a nonlinear business tends to have a nonlinear or a binary outcome. Either it works or it doesn't work. The businesses maybe aren't interesting at the small scale, so they could take years to take off, waiting for a lucky break, and then they, but they tend to have a strong network effect. So when they do take off, they accelerate quickly, and examples might include, you know, hit-driven businesses like video games, music, social networks, Some pure marketplaces like eBay and some other ones, maybe like Instagram or Pinterest, which took a few years and then kind of hit and took off. And a linear business, on the other hand, can have a variety of outcomes, can be assessed successful at different scale, different levels of scale. And so that could be things like medical device sales or real estate, or even SAS products that are created and sold. And the way those work is the more energy and time you put into selling this item or creating and selling it, the more business you create. And oftentimes it's a B to B type of business. And so it ends up being fairly linear at first, You put an extra day or effort, you know, an extra hundred calls in, you're going to get some number of customers that buy. And so you can kind of scale the business through hard work. And what we kind of thought was the best of both worlds is what's going to fit us. Cause I always came from a ba…

AI assessment note: “So I think a nonlinear business tends to have a nonlinear or a binary outcome.”

Q Regardless of kind of linear or nonlinear in status, I mean, one thing that's strikingly apparent is the importance of timing. Mike Daubert at Amplify said on the show that timing kills more companies than runway. So why is timing so crucial, do you think? And how's that been kind of prevalent with Convoy?

A Yeah, that's a really, really good question. You know, someone I used to work with always described to me as surfing. He's like, you can go out there and paddle Really hard. But if you're between waves, it doesn't really work. And I think the way I was envisioned envisioned it, I think I was with him once he was talking about buying a convertible in Seattle. And I was like, well, it's great to have a convertible, but it's not that fun when it's raining. So, you know, the timing of when you pull the roof back is going to make a big difference. Maybe Seattle is not the right spot. So I think timing is everything actually in building a company and a startup because if it's not the right time, it's not going to take off and it's not going to be reinforced. People will be getting excited about it. It's going to raise money. All these things are going to be headwinds. So I think that With Convoy, timing was crucial, and the reason it's working really well is on the trucking side, in 2014, approximately 2015, drivers started getting smartphones with a data plan and GPS. And, you know, most of the U.S.-based phone carriers started offering their free phone, the two-year upgrade phone, as a smartphone. And then on the demand side, the shipper side of our business, you know, as I mentioned with Amazon and with a lot of other companies pushing on distribution times and delivery times for …

AI assessment note: “With Convoy, timing was crucial, and the reason it's working really well is”

Q No, I'd love to get the ball rolling, though, by discussing a little bit about you, and tell me, Dan, when you were a little boy, did you always dream of reinventing the world of supply chains, and how did Convoy come about?

A When I was little, I was, well, I appreciated supply chain because it paid me 10 dollars an hour during the summer. I worked, my family had a mom and pop kind of office supply distribution business around the Northwest. And so I worked in the warehouse. I'd pull boxes down from shelves. I'd load vans and small trucks, and then even started doing some driving when I was, you know, later in my teenage years and in college. But that was more, I get paid during the summer, set up money for clothes and going on dates and things like that. Did not think that was going to be my career, but later on did a bunch of things in transportation, actually. I did some work with the Panama Canal, did some work Related to manufacturing and maintenance programs for airlines related to their parts distribution and maintenance. And then ultimately, I was at Amazon, actually, before I started Convoy. And you were asking, kind of, how did this come about? Honestly, I witnessed pretty powerful supply chain transformation happening via Amazon and how that can change industry. And, you know, consumer expectations are going up. Businesses have to react, increasing the flexibility of their supply chain so they can manage inventory costs, get things to the, you know, the right person at the right time as quickly as people expect. Which is, which is pretty fast these days. So we dove in because we thought w…

AI assessment note: “Did not think that was going to be my career, but later on”

Q a lot of things, but fundamentally, the scaling. I do want to break that into a few components, being the company itself, Yourself as CEO, and then maybe broader the team, but if we start on the company, obviously customers key to scaling. You said to me before that the first are always the hardest. Why do you think this and kind of what experience led you to that conclusion?

A Trucking is a pretty traditional industry, and folks that work in the supply chain industry have been doing this for a while. We're not bringing them something they've never purchased before and saying, here's this thing you need. We're saying, you've been purchasing this for a long time in a way that's less efficient, and we can give you more value. And so, That means they already have a status quo and they have to trust us to change what already works for them. And so getting the first few customers to make that decision is really critical. And so we did everything from, you know, thinking about how to build credibility with investors, how to really understand and go deep on individual customer needs to figure out what would work for them. And then putting a lot of time and sort of just building personal trust to lead into some of those first deliveries. And, you know, it was great. The first customer we ever had, they shipped one pallet. Actually, this was back before we were doing full truck. We were just getting started. We wanted to test the, you know, the technology and they videotaped it and they thought it was great. They were excited about it. They were excited to kind of be the first company to use it. So that was really kind of a cool experience. And again, then we got a first few, we got it rolling a little bit, and then it actually became a lot easier at least to …

AI assessment note: “they already have a status quo and they have to trust us to change”

Q What moment in your life has served as an inflection point and maybe changed the way you think?

A Several times, I think in my life, people have really pushed me to see the value of options. As a kid, it's kind of easy to ignore that. I didn't go, I don't want to put the time into to prepare and to do this thing that might lead to future options. But I had three or four people, you know, my uncle, my parents, one of my teachers really push on me to say, what matters is having more options in the future. And I remember at Yale, my dean said specifically, you know, between these two jobs you're looking at, pick the one that lets you do the other one in the future too. One was more of a one-way door, one was a two-way door. And I think that option value mindset was probably the most influential in terms of the decisions I've made in my life that have led me to have more and more options.

AI assessment note: “at Yale, my dean said specifically, you know, between these two jobs you're looking at”

Q The other interesting element of scaling is the scaling of yourself as CEO. I've spoken to over 300 of some of the biggest tech CEOs in the world, and all of them have the commonality of struggling to scale themselves as CEO. How do you think about this, and how have you seen your role develop and change with the scaling?

A I think about it a lot. It's extremely important. We've gone fast, so our company is not even three years old yet. We've been able to scale to over 200 people. We've raised, you mentioned, eighty million dollars. We have hundreds of customers. We're doing a lot of business. What we've done has happened really fast from the moment we incorporated this company, and so I feel like I've lived four or five startups at this point within Convoy. Thinking about what my role is early on, I am the chief recruiter and the chief fundraiser and the chief visionary, because without getting people on board, there is no product. There is nothing to go build. And then my job became chief product officer. And I was doing a lot of product work early on to get V one out the door. And then I became chief salesman and I had to go out and convince a bunch of customers that this was something they were really excited about and go talk to truck drivers and really understand them and figure out how we can be helpful in a build for them. And that cycle doesn't stop. And it's about just stepping back and asking yourself, where can I be the most helpful? What can I do that is going to give this company the most leverage? And where have we not hired yet? And as we hire more and more extremely competent, great people at all levels of the company, including senior leaders, my role continues to change. And I s…

AI assessment note: “Thinking about what my role is early on, I am the chief recruiter”

Q Absolutely. I do want to touch on your time at Amazon there because you also worked at Google and Microsoft. I have to ask, from working with such behemoths, what were the kind of cool takeaways, maybe operationally from being inside, that have influenced how you run Convoy today?

A I've learned from all of them. You know, they've all spent a lot of time figuring out how to build a really successful business, but they're all very different. And so, I think the one that certainly influenced me the most, primarily because I was doing it right before I started Convoy, was Amazon. And some things I took away from there were being very deep into the metrics and details Of each of the businesses, each of the teams, even as the company grows, creating a structure to do that, you know, having a set of core values that you don't just use to talk about the business to recruits, but they use every single day in meetings and in reviews and in hiring and these values, you kind of go back and back, you know, you go back to over and over again. Those are a couple of things I took away from there. You know, I think, you know, early on when I was at Microsoft and Google, there were different sort of focuses on how do you launch a product? Microsoft spent a lot of time thinking about, Hey, how do you take a product to market and launch it? And Google thought a lot about obsessing over a customer experience and always trying to be creative and clever and innovative around what you can give somebody that's better than what they've done before from a product or kind of a software experience perspective. And so I think different things stood out to me from each of those, and I …

AI assessment note: “being very deep into the metrics and details Of each of the businesses”

Q What's been the biggest challenge? If there's been a core kind of inflection point or struggle for you in that scaling, what would you say it's been?

A I think there were, there are two specific things. One was just the initial fear of, am I even going to be good at this? Wow. Being a CEO startup, founding this company, a lot of people are taking a risk and putting their livelihood in my hands or taking, you know, I have a lot of responsibility for them. So I think part of it was really proving to myself that this was going to be the right fits. I think that that It's felt pretty natural. It's actually felt like it did well. And I credit that to the fact that in my history, I've done a ton of different jobs. I never went deep on any one thing, which bothered me for a really long time. I always ask myself, I wish I could just go deep. Wouldn't it be easier if I just picked one thing and did that? But I tend to do a lot of different things. And then now in this job, I'm like, oh, well, that all turned out well, because that's actually exactly what I needed for this job. So that was kind of part one was that just rationalization of this is the thing I should be doing. And I'm going to, and I'm going to just go full steam into getting everybody fired up about this. The second part that's been challenging, you know, as we've scaled the company is really knowing who else is scaling and who else needs to develop more and isn't ready yet. And that's really hard because one, everyone that joins convoy, I think the world of, and, you kn…

AI assessment note: “there are two specific things. One was just the initial fear”

Q How did that injection affect your mentality towards capital efficiency?

A I don't think that it did. I think that generally my DNA is very frugal, and I try to be very efficient with spending money personally and, you know, and in this business. And we've always had a sense of we have to earn it. I mean, one of our core values is earn the results. We're not entitled to say, look at all this money we have. Now we can relax and spend less efficiently and We think about it as, now we have a chance to go do something bigger. So I certainly don't think it's changed our mindset around efficiency. Potentially, we've been able to take more risk in terms of things we can go test and experiment, but those are just additions to the budget, and we want to run them all efficiently.

AI assessment note: “I don't think that it did. I think that generally my DNA is very frugal”

Q We mentioned earlier the experimentation element in the scaling process. You've stated before the importance of having that culture of experimentation. What does that really mean? And how does one create a culture of experimentation where one's also not fearful of failure?

A Yeah, I think that, so what does culture really reflect? Culture reflects the values you set up in advance, but it also reflects the people you hire. You can say a whole lot of things, but if you hire people that don't reflect the cultural values that you believe in, you won't have that culture. And so one of the ways you create a culture of experimentation is you hire a lot of People who have been part of organizations and companies that do a lot of experiments. And then that, that can be both the type of person from where they come, like the company they come from, but also the type of person that they are. And so investing more heavily in folks with a data background, a data science background is extremely valuable. And so we were able to do that early on, bringing in folks with a data background. We've only since improved and beefed that up. And then hiring people that came out of pretty strong product management cultures where it Experimentation was very valued and that we're in very data centric organizations like Amazon, for example. And so I think, you know, one talking about it a lot, saying that we value it, making it part of the process. Step one, that you got to hire people though, that really believe in it coming in because you're right. It is risky. And if they're not viewing it as valuable, they're actually nervous about it. They're just going to naturally not do…

AI assessment note: “one of the ways you create a culture of experimentation is you hire”

Q What's been the biggest challenge? If there's been a core kind of inflection point or struggle for you in that scaling, what would you say it's been?

A I think there were, there are two specific things. One was just the initial fear of, am I even going to be good at this? Wow. Being a CEO startup, founding this company, a lot of people are taking a risk and putting their livelihood in my hands or taking, you know, I have a lot of responsibility for them. So I think part of it was really proving to myself that this was going to be the right fits. I think that that It's felt pretty natural. It's actually felt like it did well. And I credit that to the fact that in my history, I've done a ton of different jobs. I never went deep on any one thing, which bothered me for a really long time. I always ask myself, I wish I could just go deep. Wouldn't it be easier if I just picked one thing and did that? But I tend to do a lot of different things. And then now in this job, I'm like, oh, well, that all turned out well, because that's actually exactly what I needed for this job. So that was kind of part one was that just rationalization of this is the thing I should be doing. And I'm going to, and I'm going to just go full steam into getting everybody fired up about this. The second part that's been challenging, you know, as we've scaled the company is really knowing who else is scaling and who else needs to develop more and isn't ready yet. And that's really hard because one, everyone that joins convoy, I think the world of, and, you kn…

AI assessment note: “I think there were, there are two specific things. One was just the initial fear”

Q Absolutely. I do want to touch on your time at Amazon there because you also worked at Google and Microsoft. I have to ask, from working with such behemoths, what were the kind of cool takeaways, maybe operationally from being inside, that have influenced how you run Convoy today?

A I've learned from all of them. You know, they've all spent a lot of time figuring out how to build a really successful business, but they're all very different. And so, I think the one that certainly influenced me the most, primarily because I was doing it right before I started Convoy, was Amazon. And some things I took away from there were being very deep into the metrics and details Of each of the businesses, each of the teams, even as the company grows, creating a structure to do that, you know, having a set of core values that you don't just use to talk about the business to recruits, but they use every single day in meetings and in reviews and in hiring and these values, you kind of go back and back, you know, you go back to over and over again. Those are a couple of things I took away from there. You know, I think, you know, early on when I was at Microsoft and Google, there were different sort of focuses on how do you launch a product? Microsoft spent a lot of time thinking about, Hey, how do you take a product to market and launch it? And Google thought a lot about obsessing over a customer experience and always trying to be creative and clever and innovative around what you can give somebody that's better than what they've done before from a product or kind of a software experience perspective. And so I think different things stood out to me from each of those, and I …

AI assessment note: “some things I took away from there were being very deep into the metrics”

Q Speaking of kind of the door opening, the door also opened in another way being fundraising. You've raised over From many friends and actually former guests on the show, we mentioned, uh, Anu at YC there. Tell me, what was your strategy for choosing the right investors and the ball composition? Let's start on that.

A Yeah. I mean, if I, if I go back to the beginning, I think as most early entrepreneurs would say, especially this is my first startup. And so first and foremost was just getting investors, um, you know, building a story that was compelling to somebody that would give us money. I think once we, once we quickly realized the type of business we were going after was different than a Aren't tech companies for the most part. And so they're not aware of, or even influenced by many of the notable tech investors and tech names. And so what we found when we're going to, let's say, you know, it could be the middle America, it could be Eastern Washington or an area where someone's building a manufacturing plant. We need to build credibility with them when they need to trust us. Cause they're going to start, you know, they're going to give us the product of their, their labor, and they're going to trust their, the experience that their customers have receiving their products in our, in the trucks that we're, that we're sending over. And so There's a lot of trust that had to be built up, and we actually thought about our investors as a way to build that trust. And so when we were able to get investors that had built significant companies to come be a part of Convoy, that lent a lot of credibility and trust to our customers where they could say, okay, the founder of Amazon or the person who, …

AI assessment note: “we actually thought about our investors as a way to build that trust.”

Q Before we kind of discuss that kind of culture of experimentation, the final element on fundraising I do want to touch on, we had Anu and Ali from YC Continuity Fund on the show. I'm intrigued, why did you choose YC as the chosen kind of lead series B investor of choice?

A Yeah. So one, Anu and Ali are fantastic. Two, I think we felt like there was a really good opportunity to get kind of the best of two worlds. There's a growth fund, those partners, as well as the organization general has very, very deep ties into many of the growth stage companies across Silicon Valley and across the world. And so we would be able to get a lot of great experience and insights from those companies through the YC network. And the partners have a lot of experience scaling and buildings. They can help us understand that. So we felt like we got that benefit, which is what we needed entering kind of a growth phase. But the DNA of YC is about deeply helping companies succeed. And it's a service mindset. And sort of, as I mentioned, I want to lean into the resources. I want to lean into the investors that we're working with so we can get the most out of them and give our company the best chance at growing. As you mentioned, it's an efficient way of doing it because it's already a group we're working with. And so I felt like because of that DNA that YC has as an incubator and its founding, we could feel that. And I have never worked with a group that this quickly was, you know, so quickly into our relationship with them has done so many proactive things to kind of help us. The Gia, who runs recruiting over there, is fantastic. She's been very hands-on in a couple of maj…

AI assessment note: “we felt like there was a really good opportunity to get kind of the best of two worlds.”

Q a lot of things, but fundamentally, the scaling. I do want to break that into a few components, being the company itself, Yourself as CEO, and then maybe broader the team, but if we start on the company, obviously customers key to scaling. You said to me before that the first are always the hardest. Why do you think this and kind of what experience led you to that conclusion?

A Trucking is a pretty traditional industry, and folks that work in the supply chain industry have been doing this for a while. We're not bringing them something they've never purchased before and saying, here's this thing you need. We're saying, you've been purchasing this for a long time in a way that's less efficient, and we can give you more value. And so, That means they already have a status quo and they have to trust us to change what already works for them. And so getting the first few customers to make that decision is really critical. And so we did everything from, you know, thinking about how to build credibility with investors, how to really understand and go deep on individual customer needs to figure out what would work for them. And then putting a lot of time and sort of just building personal trust to lead into some of those first deliveries. And, you know, it was great. The first customer we ever had, they shipped one pallet. Actually, this was back before we were doing full truck. We were just getting started. We wanted to test the, you know, the technology and they videotaped it and they thought it was great. They were excited about it. They were excited to kind of be the first company to use it. So that was really kind of a cool experience. And again, then we got a first few, we got it rolling a little bit, and then it actually became a lot easier at least to …

AI assessment note: “they already have a status quo and they have to trust us to change”

Q Can I ask Dan, how do you respond when experiments go wrong?

A Well, I'd say one thing is an experiment never goes wrong. An experiment has an outcome, and we learn from it. And the outcome could be the thing we thought was going to work, worked, or it could be the thing we thought was going to work, didn't work. But in either case, we now have more data and information, and we can go make a smarter decision, or we can run a better experiment. And so I think that's first and foremost having a culture where there's no such thing as a failed experiment. There's just different levels of data. One thing we do that's fun, though, is when we do different types of experiments, especially ones that have more UI or more, we can, we can frame them more clearly to the employees. We put them up on a wall in our office, and we'll have, like, the three treatments, or the three different things we're going to test, and we'll ask people to vote on which one they think is going to win, and then they can win, like, a gift card. You know, like, we have, like, prizes and stuff, so.

AI assessment note: “an experiment never goes wrong. An experiment has an outcome, and we learn from it.”

Q Can I ask from an internal perspective, how did you think about board composition?

A Yeah, we wanted, I think some people kind of lean in To their investors and their board and think, okay, I'm going to approach this. I'm going to get a lot of value. I'm going to work with these people really closely, and I want to have a great relationship, and I want to use their experience to get a lot for my company, and some people kind of lean out and say, this is a necessary evil of building a company, and I was much more in the first camp. That's why we ended up having quite a few investors. I received some advice early on. Dan, you have to choose. Are you going to lean in, and is this going to be something you nurture and develop? Are you going to get a lot of value from this over time? If you're not going to, don't worry about having as many people, but if you're going to lean in and get that value, then consider everyone that's investing as a resource and really play into that. So the board was the same, where we really wanted to have people around the table who had seen a lot of different things, who had built companies, who had gone through this journey before, and who were really well connected and networked, so that across many dimensions of this, from the quick question of, hey, when you built your company, what happened here? To, hey, we're scaling at this point, who else do you know that's done that? We would get a lot of really high quality answers. So the bo…

AI assessment note: “the board composition came very much down to people that we felt would be really, really valuable”

Q Speaking of kind of the door opening, the door also opened in another way being fundraising. You've raised over From many friends and actually former guests on the show, we mentioned, uh, Anu at YC there. Tell me, what was your strategy for choosing the right investors and the ball composition? Let's start on that.

A Yeah. I mean, if I, if I go back to the beginning, I think as most early entrepreneurs would say, especially this is my first startup. And so first and foremost was just getting investors, um, you know, building a story that was compelling to somebody that would give us money. I think once we, once we quickly realized the type of business we were going after was different than a Aren't tech companies for the most part. And so they're not aware of, or even influenced by many of the notable tech investors and tech names. And so what we found when we're going to, let's say, you know, it could be the middle America, it could be Eastern Washington or an area where someone's building a manufacturing plant. We need to build credibility with them when they need to trust us. Cause they're going to start, you know, they're going to give us the product of their, their labor, and they're going to trust their, the experience that their customers have receiving their products in our, in the trucks that we're, that we're sending over. And so There's a lot of trust that had to be built up, and we actually thought about our investors as a way to build that trust. And so when we were able to get investors that had built significant companies to come be a part of Convoy, that lent a lot of credibility and trust to our customers where they could say, okay, the founder of Amazon or the person who, …

AI assessment note: “investors can help us earn credibility with customers”

Q Regardless of kind of linear or nonlinear in status, I mean, one thing that's strikingly apparent is the importance of timing. Mike Daubert at Amplify said on the show that timing kills more companies than runway. So why is timing so crucial, do you think? And how's that been kind of prevalent with Convoy?

A Yeah, that's a really, really good question. You know, someone I used to work with always described to me as surfing. He's like, you can go out there and paddle Really hard. But if you're between waves, it doesn't really work. And I think the way I was envisioned envisioned it, I think I was with him once he was talking about buying a convertible in Seattle. And I was like, well, it's great to have a convertible, but it's not that fun when it's raining. So, you know, the timing of when you pull the roof back is going to make a big difference. Maybe Seattle is not the right spot. So I think timing is everything actually in building a company and a startup because if it's not the right time, it's not going to take off and it's not going to be reinforced. People will be getting excited about it. It's going to raise money. All these things are going to be headwinds. So I think that With Convoy, timing was crucial, and the reason it's working really well is on the trucking side, in 2014, approximately 2015, drivers started getting smartphones with a data plan and GPS. And, you know, most of the U.S.-based phone carriers started offering their free phone, the two-year upgrade phone, as a smartphone. And then on the demand side, the shipper side of our business, you know, as I mentioned with Amazon and with a lot of other companies pushing on distribution times and delivery times for …

AI assessment note: “With Convoy, timing was crucial, and the reason it's working really well”

Q We mentioned earlier the experimentation element in the scaling process. You've stated before the importance of having that culture of experimentation. What does that really mean? And how does one create a culture of experimentation where one's also not fearful of failure?

A Yeah, I think that, so what does culture really reflect? Culture reflects the values you set up in advance, but it also reflects the people you hire. You can say a whole lot of things, but if you hire people that don't reflect the cultural values that you believe in, you won't have that culture. And so one of the ways you create a culture of experimentation is you hire a lot of People who have been part of organizations and companies that do a lot of experiments. And then that, that can be both the type of person from where they come, like the company they come from, but also the type of person that they are. And so investing more heavily in folks with a data background, a data science background is extremely valuable. And so we were able to do that early on, bringing in folks with a data background. We've only since improved and beefed that up. And then hiring people that came out of pretty strong product management cultures where it Experimentation was very valued and that we're in very data centric organizations like Amazon, for example. And so I think, you know, one talking about it a lot, saying that we value it, making it part of the process. Step one, that you got to hire people though, that really believe in it coming in because you're right. It is risky. And if they're not viewing it as valuable, they're actually nervous about it. They're just going to naturally not do…

AI assessment note: “one of the ways you create a culture of experimentation is you hire”

Q Can I ask from an internal perspective, how did you think about board composition?

A Yeah, we wanted, I think some people kind of lean in To their investors and their board and think, okay, I'm going to approach this. I'm going to get a lot of value. I'm going to work with these people really closely, and I want to have a great relationship, and I want to use their experience to get a lot for my company, and some people kind of lean out and say, this is a necessary evil of building a company, and I was much more in the first camp. That's why we ended up having quite a few investors. I received some advice early on. Dan, you have to choose. Are you going to lean in, and is this going to be something you nurture and develop? Are you going to get a lot of value from this over time? If you're not going to, don't worry about having as many people, but if you're going to lean in and get that value, then consider everyone that's investing as a resource and really play into that. So the board was the same, where we really wanted to have people around the table who had seen a lot of different things, who had built companies, who had gone through this journey before, and who were really well connected and networked, so that across many dimensions of this, from the quick question of, hey, when you built your company, what happened here? To, hey, we're scaling at this point, who else do you know that's done that? We would get a lot of really high quality answers. So the bo…

AI assessment note: “board composition came very much down to people that we felt would be really, really valuable”

Q Can I ask, you spoke about kind of board chemistry there. I think, you know, an interesting time is always when some element of friction is added. I'd love to hear about a time when maybe you've not gone with a board suggestion. How did you communicate this, and kind of what's the advice for founders on maybe not taking the suggested board path?

A Yeah, I would say a couple things is, on that, the key point there, I think is, you know, the advice Take the decision and own the outcome of the decision. Your board is giving you advice. It probably sometimes feels like because everyone on the board is often more experienced than you or has had more success to date in their career, that what they say is what you should do. And that if you don't do it and you go back and you're not successful, then they're going to hold it over your head. I think that the, the opposite is actually true, which is, Hey, they're probably really busy. So they might not remember what they said. They're saying it off the cuff. They're saying it based on a lot of experience. But they're not seeing everything that you're seeing, and whatever outcome happens is your responsibility. They're not going to say, well, you know, I did give you that advice, so therefore it didn't work. It's definitely on me. It's your decision. So you just need to always remember that you have to live with it, so you need to make the decision, and they're seeing this part-time, you're seeing this full-time. In terms of the decisions and some things, I mean, we've had some pretty significant discussions about pace, the types of categories we go into, and from time to time, someone will suggest something that's Just, you know, would be really distracting. It's like, Hey, why do…

AI assessment note: “Take the decision and own the outcome of the decision.”