Issue #24: A conversation with a co-founder
I talked to over a dozen potential technical co-founder candidates and Rylan ended up being the perfect person.
I was first introduced to Rylan Hawkins in early October. David Tsai, co-founder and CTO of GoodShip, made the initial introduction. David and his co-founder, GoodShip CEO Ryan Soskin, had both worked with Rylan at Convoy and absolutely raved about his leadership, engineering chops, and experience. At the time that we met, there were grumblings that something was going to happen soon with Convoy. There were rumors flying around that an acquisition was about to happen but no one knew who would be buying them.
Convoy had a few different businesses: they had their freight brokerage, which is where all the grief has been historically targeted, they had a product called Convoy For Brokers, that allowed other brokers to connect directly with Convoy’s carrier network and leverage its technology, and they also had Convoy Go, which was a drop trailer program that they were building out that allowed carriers to run power-only moves within Convoy’s network, something shippers really appreciated given the flexibility that comes with a drop trailer network. Rylan was the General Manager for Convoy for Brokers and Convoy Go.
When Rylan and I first talked about potentially starting Cargado together, Rylan wasn’t willing to entertain the idea of leaving Convoy. He was one of the earliest engineering hires and had been there for over seven years. He had seen the company grow from a startup and wasn’t willing to walk away until he knew where it was going. When I was building Forager, my CTO, Matt Weber, told me once that he’d be there til the end of Forager, whether it was through an acquisition or to turn off the lights at the end. Thankfully, we were acquired, but I saw that same trait in Rylan, that he was going to stay through an acquisition or to turn off the lights. I was willing to wait for that to conclude. It ended a few weeks later with Convoy winding down and Flexport picking up the tech.
We’re at the point now, with this new funding, where we’re ready to start building an engineering team. Our team started with Rylan and three former Convoy engineers. The team is tight-knit and has a ton of amazing freight experience, blended in with Rylan’s Microsoft experience and previous time starting his own company. Another one of our team members has brought some lessons learned from his time at Google before Convoy, but we’re ready to expand.
I figured I would change it up a little bit and bring Rylan into the conversation for this newsletter.
Matt: I remember, the first two weeks after everyone was onboarded, we basically spent the whole time on Zoom talking about technical decisions and lessons learned from everyone’s time at Convoy. I feel like that enabled the team to move as quickly as it has and to launch our first product 4.5 months after doing that work. Can you talk about what kind of decisions were made in that two-week timespan?
Rylan: This is something that speaks to the heart of a really natural tension that exists in the earliest phases of a startup: how do you balance short term and long term velocity. Those first couple weeks we spent talking about the core technical decisions we were going to rely on for many years to come. There were the easy things like what cloud provider do we want to use (for us that was AWS primarily because of the team’s familiarity). But there were also harder decisions too, like what Pub/Sub technology and pattern do we want to use to meet our requirements of auditability, analytics and async production processing.
Of course, we could have spent months looking at every option out there, and we could have also just gone with what we were familiar with, but we needed to tow the line. Some of the ways we did that was timeboxing the effort and working in parallel. So while the engineering team was thinking about these decisions, we were designing visual prototypes of our initial product and showing it to prospective customers. On familiarity, choosing the familiar option gets you speed in the short term, but you also can’t be afraid to use newer technology. Most companies select a technology and stick with that for a long time, while in the meantime new solutions are cropping up all over the place that are better ways of doing things. This is often why startups can compete with larger incumbents because the platform they exist on is just fundamentally better.
I will say wherever possible, we try to live a mantra we learned at our previous companies of innovating deliberately. There are so many things a company has to get right, you must choose where you want to truly differentiate and when to simply choose to buy instead of build. There are so many companies with amazing platforms out there right now that makes building a company so much easier. We don’t need to reinvent user authentication or A/B experimentation or multi-channel notifications or in-app chat. There are entire companies focused on how to design those experiences and all the features you might need, and their price point will almost always be lower than yours to build given the scale at which they operate.
I will say though, we were in a unique position to be able to spend the time we did getting our technology choices right. Our team already had a lot of experience in the industry, we’d already spent many hours with customers and had deep insights into what would work and what wouldn’t. Others may not have the luxury to focus on their foundational choices when the more existential question of product market fit is unanswered.
Matt: And what about how we make product decisions today? I feel like I see you enabling Steven, Jonathan, and Teagan to make their own decisions but can you elaborate on how that works?
Rylan: Well again this is another place that you have to balance as a leader. Amazing folks, like we have, means you have to give them autonomy and ownership or else they’ll go somewhere else. We hire people for their ideas and their judgment, so, of course, I want to capture the best of those and use them. I find that working at a startup is attractive to many because of the ability to just go and own something and do it repeatedly across a large swath of areas. This is because in the earliest stages there is an infinite number of things to do, so everyone has to just trust that everyone else is doing the most important things, and because all our employees get equity they care more about growing the value of the company which results in more reward than just getting recognized for their work.
On the other side of the coin though, the earliest decisions we make are some of the most lasting ones, the ones at the bottom of the stack that are really hard to untangle later. So this is why I also dive deep with the team to establish the patterns that everyone else will follow and the engineering culture that will last for the life of the company. Some of the cultural items are things like prioritizing simplicity, where simple solutions can be harder to realize, but have more lasting value than complex ones because of the ability to easily understand and innovate on top of them.
I also believe heavily that one of the most important things in engineering is building good interfaces. This is because interfaces are often one-way doors instead of two-way doors, meaning they’re hard to change later on and thus deserve more consideration before shipping. Interfaces are the things other systems rely on, so when you get it wrong you find it's harder to untangle across all the places that rely on that interface.
Matt: Okay, now a hardball question. When you think about building an engineering culture, especially one that’s remote, what do you think are the most important aspects of doing that successfully?
Rylan: There are many things here, but top of mind is the importance of periodic connection in real life. One of our investors really pushed us to do once-a-quarter offsites where we work, eat, reflect and brainstorm together. This has been invaluable and something I look forward to every time we have one. We spent our most recent time in Monterrey with customers and partners, watching them work, sharing a meal and just sitting in their office learning about how they run their business. We also got to eat incredible food together and just be people, not just co-workers. It’s those times that create connection and stories that bind us together, which helps a lot in the day to day.
Matt: Alright, well we know no two engineers are the same. But there’s definitely a prototypical engineer we want to bring onto the team. What kind of experience are you looking for? Tell me what your ideal engineer embodies.
Rylan: I think I can best answer this by talking about the attributes of the incredible team we have already and what I value so much in them. Here is a list:
Strong product and customer empathy. They know when something doesn’t feel right or doesn’t allow the customer to get what they want. This might be a user experience thing or a functional thing.
They think both short and long term. They recognize the need to ship, but they know when something is consequential and sets a standard that will be hard to change later. They cut themselves off if they realize something isn’t worth the ROI right now.
They think about reusability. They build for what’s needed right now but open up the possibility to reuse some functionality later.
They think about each other and who might have a point of view on a problem even if it’s different. They consider who might need to know something and talk to them to share their knowledge.
They think concretely with examples and in code, but they also take a step back and recognize when the team is falling into bad patterns or not being strategic enough or not prioritizing something more fundamental to make things easier or faster.
They have functional knowledge of the systems they use, from programming languages, design patterns, infrastructure systems, browsers, common APIs, and available SaaS options in the wild.
They think about the company's business model and strategy in addition to the systems and code.
They reflect on their learnings in the past and the scar tissue they’ve built up.
They take pride in their craftsmanship.
They write things down and always follow up, so when I or others delegate or help make a decision we know it will get done without having to check in again.
Matt: We’ve been building a product for about six months now. What lessons have you learned from that and what would you share with other early stage founders about building software at the earliest stage?
Rylan: I think the past six months have reminded me of one of the things I believe, but can be easy to get distracted and forget. It is the importance of having direct engagement between product and engineering folks and customers. They need to hear, see and be around customers. It creates so much empathy, understanding, connection and motivation that it pays off very quickly. It helps retention, it helps surface the best ideas and helps everyone prioritize quickly.
Matt: Last question – what do you see as the biggest technical challenge we’re going to tackle in the next twelve months as a team?
Rylan: What’s so great about logistics is that it’s just such an interesting and complex problem. It’s complex and interesting because you’re trying to reflect all the ways people operate and move things in the real world. So what makes it fun is that we get to use a lot of the most interesting tech out there and apply it. We get to go deep on great product engineering, machine learning, apply AI in particular areas where it makes a difference, build well-designed data pipelines, intuitive user interfaces, build securely, consider our foundational infrastructure and ultimately think strategically. We hire people who can both consider the deep technology and the business elements at the same time. This is what makes it such a challenge and also so rewarding.
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So yeah, we have this new influx of capital. We’re going to be smart about how and when we spend it, but we do have some budget for additional engineering talent. You can find all the roles posted here!
This was a very good article. Thank you for sharing, Matt and Rylan.