The invention of the automobile started out as a simple technology that solved a transportation problem for people, but quickly came to dominate transit and many other elements of people’s lives around the world. To accommodate the growing popularity of cars, cities rushed to develop their infrastructure and planned their layouts based on this technology, leading to congestion and other issues. With the introduction of new technologies, such as car sharing, ride sharing, e-hailing, and micromobility, today’s cities and their needs look vastly different from the past, introducing the need for governments to quickly adapt in order to undo a lot of the damage that’s been done by building cities around cars.

Of these technologies, micromobility—a category of light-weight transportation designed for individual use, such as bikes and scooters—has generated a lot of interest in recent years. According to McKinsey, micromobility operators have attracted a strong customer base roughly two to three times faster than either car or ride hailing due to the speed of trips compared to car-based trips and the freedom of fresh air. Consumers aren’t the only ones benefiting from micromobility. The economics benefit industry participants—it’s a lot easier to scale up micromobility assets compared to car-based sharing solutions—and micromobility options are taking cars off of city streets, thus reducing congestion and creating sustainable transportation options for communities around the world. Though there are significant upsides to micromobility, the market also introduces new challenges for stakeholders, specifically cities and operators. 

William Henderson, founder and CEO of Ride Report, built his career as an early employee at product-focused companies like Apple and Square. Upon leaving Square in 2013, William knew he wanted to start a company and decided to work on a market that he was deeply passionate about, which led him to micromobility. The moment scooter sharing started taking off in the US, William realized there was a new model for government regulation that would require new technology, and so Ride Report was born. Ride Report, a solution that empowers cities with tools to help them make transportation more equitable, efficient, and sustainable, has monitored more than 100,000 unique vehicles in 2020 alone and has partnered with over 70 cities worldwide to help prioritize people-friendly communities and a robust transportation system built for everyone.

We recently sat down with William to discuss his vision for Ride Report, leadership insights he picked up from Jack Dorsey as an early employee at Square, and why his team is his biggest inspiration.

Unusual: Can you give us a little background on yourself?

William: My background is in engineering, but I didn’t actually go to school to be an engineer. I studied math and philosophy in school and graduated without many of the skills needed to be in the tech industry. Early in my career, I was particularly drawn to Apple due to its product-centric nature and managed to find my way there after a lot of pounding on the door. At Apple, I realized I wasn’t a big company person at all, but this experience was really important for my growth—I saw what it was like to build a great product, and most importantly, had the opportunity to work on a team that not only sweat the details, but was constantly thinking empathetically about the user. Around the time I was ready to start looking for my next opportunity, I was lucky enough to meet Jack Dorsey and hear about Square when the company was still operating out of his apartment. Intrigued by the idea, I joined Square as one of its first engineers and led the mobile team that delivered the original credit card acceptance and point of sale applications on iPad. Pretty soon after launching these apps, Jack had me spearhead the consumer division, which I ran until I left in 2013. This division acted like a company within Square and gave me a lot of core startup experience, as well as relevant domain knowledge around payments, data security, and data privacy that has proved to be valuable at Ride Report. 

Square was the classic, crazy startup ride. We went from 10 to 1,000 people in three years and faced a lot of challenges in a difficult product space. By the time I left, I knew that I wanted to start a company and whether I liked it or not, this was who I was—leading a team and building products. But I also understood that if I was going to get back on the crazy startup rollercoaster, it had to be for a mission that I really cared about—something that was core to what I believe and what I want to fight to have exist in the world. That’s what led me to the micromobility market. I was in this place where I wanted to work on something, but I didn’t know what the product idea was. I picked the market first, which is a little bit unusual. I didn’t say, “Oh my gosh, I have this brilliant insight into micromobility.” Micromobility didn’t exist at the time. I picked a market I knew I cared about, built things, and hung out with potential customers. Basically, I just dwelled in that market for a while before I really figured out what I wanted to do. I like to say I was in the right place at the wrong time. I found if you are willing to wait around in the right place long enough, your time will come. And that’s exactly what happened. As soon as we saw the emergence of the new dockless models, scooter sharing, and bike sharing in China, we knew that this was our calling and micromobility was going to be really important in this country. We didn’t predict the actual form factor—that definitely caught us by surprise—but the moment that scooter sharing started taking off in the US and we saw a new model for government regulation, we knew that this was our big moment and we jumped on it. At that point, we had a few customers and a small team, and we were able to just go after the opportunity full throttle.

Unusual: Can you tell us a bit more about Ride Report and its mission and vision?

William: If you look at where we are as a society, we have one mode of transportation—the personally owned car. The car started out as a simple technology that solved a critical problem for people, but it quickly came to dominate transportation and many other elements of our lives. Making and selling cars became an economic tool for our country and building the infrastructure that cars run on has had a massive impact on how our cities are laid out and what our foreign policy looks like. Today, cities have a very specific set of problems they are trying to solve. They’re trying to undo a lot of the damage that’s been done by building everything around cars and create cities that are more people-centric. Cities are also trying to combat congestion and the fact that automobile infrastructure really doesn’t scale past a certain point. The energy efficiency of a car will never be that great because you’re driving around two tons of metal just for one person, which makes them a major driver of climate change. 

At the very highest level, Ride Report is trying to help cities imagine what their infrastructure should look like in the 21st century. We want to help cities take back control of their streets. We believe that transition has to happen independent of whether Ride Report exists, but our goal is to accelerate that evolution by giving cities smart API-driven tools to regulate micromobility. Through Ride Report, cities are able to regulate with a lot more control, but also in a way that’s much more efficient for the micromobility companies. These same tools capture revenue, so that cities are able to finance maintenance and reallocation of space to more efficient modes of transportation. This is a huge problem right now where every city is facing a crisis because they rely on the gas tax. The gas tax is going to drop off a cliff as vehicles are electrified and become more fuel efficient. Additionally, the gas tax has a lot of strings attached and doesn’t allow cities to really have complete autonomy in terms of how they re-imagine their cities and their streets. Our mission is to accelerate the transition to a more sustainable, equitable, and efficient transportation system.

Unusual: Did you always know you wanted to be an entrepreneur and when did you know you were ready to start your journey?

William: Yes and no. I’ve always been someone who just creates products. Even before I really knew what I was doing, I was making things. I remember releasing products when I was just sitting around in high school. No one used them, but I made them anyway. I made websites for each product I created to try and emulate the companies that I admired. But I didn’t know I wanted to start a company until I was leading a team at Square. One of the biggest things I learned from Jack Dorsey and will always remember him saying to me is, “You’re a product person—you can’t change that. But you can’t stay as involved with the product as you are right now. If you’re going to scale as a leader and scale this team you’re leading, you’ve got to be able to step away.” He taught me to think about a company or team that you’re leading as a product. What are the inputs and outputs? Who is using it? And what can you do to use that same attention to detail and empathy to improve the environment of the team, how it’s structured, and the processes it uses to communicate and collaborate? That really stuck with me and by the time I got done at Square, I had some pretty specific notions for how I wanted to run a company differently from Square and what that would look like.  

Unusual: What has been the hardest aspect of entrepreneurship that nobody warned you about or that you just were not expecting?

William: The hardest thing is staying out of react mode. When you first get started, it’s a good thing to react to everything because you’re still learning and the team is really small. In those early days, the quicker you can respond to a new opportunity or a new challenge, the better. But as you start to scale the team and vision and go out to fundraise, you’re suddenly not just thinking about what you’re doing tomorrow and next week, but need to think months or even years out. You can’t stay in react mode. As a founder and a team leader, you need to make that transition pretty early in order to spend your time more intentionally and be really thoughtful about what you need to do, even when nobody is asking for it. What do you need to do right now to make sure you can be where you need to be in six months or a year down the line? I’ve put a lot of systems in place to help me plan. As an example, I treat my calendar as a product, which is another thing I learned from Jack. Jack would have one day a week where he just focused on marketing, one day a week where he just focused on products, and another where he just focused on the team. I don’t do exactly the same thing, but what I took from his exercise is that he’s very intentional about designing how he uses his time—he didn’t just let his calendar fill up and then hope that it was the right stuff. I also do a lot of writing for myself. Some of it I share, some of it I’d never share, but I start off every single week with that practice and think about my goals for the company and myself. What do I view as my job? What are the responsibilities of my job and how would I rate myself in each of those responsibilities today? This exercise helps me gain a sense of what’s most urgent, not in terms of what’s the loudest thing I can react to right now, but what’s the most pertinent when it comes to where I want to be or where I want the company to be at the end of the quarter and at the end of the year. Each week I plan my week around that objective or set of objectives. Taking this time every week has been a grounding and powerful exercise—it puts me in a totally different mindset for the rest of the week.

Unusual: Who is your biggest influence or inspiration and why?

William: My employees. We are a very values-driven company and put everything we believe and how we are upholding these beliefs into a public handbook. Anyone who is interested in applying to the company ends up reading it and it usually is a major reason why they apply. Then they show up and start looking for ways to make the company even better. And a lot of the time, that means doing things that I never would have thought of or asking me to do things better in a way I might not have done on my own. 

After both of our fundraising rounds, I shared our term sheets with the company. Obviously, it was very exciting to have a term sheet, but the team went off and started kicking the tires. They started by looking at the investors’ websites, who else they invested in, what they care about, and how they put what they say they care about into practice. I love that they didn’t just say, “Ooh, we have a term sheet!” Instead, they said, “Is this good enough for us?” It really was awesome—both times they came back and said, “Wow, these investors are amazing. We didn’t even think there were investors like this out there and they chose us.” Both times were incredible moments—to feel like I had such good alignment between what I cared about, what the team cared about, and what our investors cared about. This team really is a huge source of inspiration and growth for me.

Unusual: What is the biggest tip you’d give aspiring entrepreneurs just starting out in their journey?

William: I have a different tip depending on which stage of the journey they are on. If they are really just starting out, don’t have a team, and maybe don’t even know which market they are in yet, I suggest keeping a list of ideas. I call this list “the shelf”. Every entrepreneur is different, but someone who is a product-centric entrepreneur like myself probably already has a list they’ve been keeping. At some point they’re going to decide, “Hey, I want to start my own thing.” The first week after I left Square, I took my list and decided to build one idea every week for eight weeks. At the end of each week I reevaluated to see if I wanted to keep working on the idea. If I didn’t want to, I started another idea the following week. This method works for me because it’s always clear after a week if I’m excited about something. If the idea feels like it has potential, I keep working on it and if after a week I’m not excited, I give myself permission to start something else and maybe pick back up on the idea further down the road. By proceeding this way, I have found you go with whatever idea has momentum and lo and behold, a lot of times the thing that has momentum for you will also get other people excited.

Unusual: What’s your biggest fundraising tip?

William: My biggest tip is to tell a story and start with yourself. When I was first preparing to raise money, I was so intent on making the case for the business and the market opportunity that I forgot to tell the story about why I’m so passionate about what we’re doing at Ride Report, who I am, and what I value. It turns out that at an early stage, your story is going to be the most compelling part of your pitch to investors. At the early stage, you haven’t figured out all the other stuff, but if you can get an investor to see through your eyes and share your passion in the first 20 minutes of the meeting, it’s so much easier to get through the rest of your pitch. And if you do get through the rest, you know you have an investor who actually cares about your mission and shares some of your values or your passions versus someone who just sees a big financial opportunity. It took me a while to get this right. 

To be honest, I think I was perhaps intentionally avoiding speaking about why I was so passionate about this market and why it mattered so much to me. When I started in this space, there was no market, but I still went for it. Most investors were not paying attention to micromobility during this period and even in the summer of 2018 (when we were pitching) there was a lot of skepticism. At some level I was also worried that investors would see my passion as a liability—that I would be seeing the world as I wanted it to be rather than as it was. Because of these concerns, I was really intent on trying to prove the market opportunity and led with this in my pitch versus leading with my passion and dedication to the market. However, once I made the switch to leading with my story and passion, I saw a huge difference.

Learn more about how Ride Report is making micromobility work