Disrupting city transportation with technology: Drew Crofton from Sidecar

Drew Crofton Sidecar

Drew Crofton, Sidecar

Los Angeles

Interview by Laura Piety


A Rverie Conversation with Drew Crofton, manager of Strategic Initiatives at Sidecar, a smartphone app that matches everyday people in their own car with people nearby for shared rides. 

My name is Drew Crofton and I’m the manager of Strategic Initiatives at Sidecar. You’re probably wondering what strategic initiatives means?

Yep.

It’s a combination of strategy, operations and marketing. I’m based in LA but it’s a nationwide focus.

What has been your work experience prior to working at Sidecar?

I worked in investment banking after college and did finance for a large bank that went under during the financial crisis. It was a good foundation, but at the same time I wanted to get out of the industry because it was pretty unstable. I ended up going to grad school at University College London in England where I got a Masters in International Public Policy. 

People are usually confused about how that particular subject translates into what I do today, but the main crossover is the areas of analysis and quantitative and qualitative research. I used those skills in my Masters to strategize about countries and governments, but today I use the techniques to strategize for companies. 

I used those skills in my Masters to strategize about countries and governments, but today I use the techniques to strategize for companies.

After graduating I moved back to the States and worked for a market research and strategy company based in LA called Kelton Global. I was there for 2 ½ years. The role included a lot of traveling and organizing focus groups for big brands such as Dominos, Target and Nordstrom. As a result I’ve been to nearly every major city in the Continental United States!

I got into the startup sphere about 2 ½ years ago. I’ve always been interested in the tech world, and actually started my own website business in college, so when a friend reached out to me to let me know the startup, Wheelz, was hiring, I was immediately interested. Wheelz was in the car sharing space. By the time it was acquired I was fully immersed in transportation and technology, and got connected to Sidecar.

Sidecar

There’s been a lot of press around ride-sharing and people intentionally choosing to live without cars. Why is this important and how is it transforming the face of our cities?

There’s a lot of emerging trends about car ownership, public transport and even attitudes about cars. Much of this was brought on by the recession. It used to be the American thing... you turned 16 and your parent bought you a car. Now with a global recession, parents with financial difficulties and homes being foreclosed on, there's a whole group of kids who never got that car. And the kids actually realized they can get on without one, from choosing to bike, being more local or grabbing a ride with others. 

It used to be the American thing... you turned 16 and your parent bought you a car. Now with a global recession, parents with financial difficulties and homes being foreclosed on, there’s a whole group of kids who never got that car.

A car can be freedom, or a burden. There’s been a shift around what freedom actually means. Yes, it can mean the freedom of getting from Point A to Point B… but with that comes a car payment, gas, parking, insurance… drinking and driving.

There are also emerging trends that show more people are returning to urban environments and cities from the suburbs, back to the centers of NYC, LA, San Francisco and Chicago etc. As more people return to the city center there are less places for people to park, and new technology companies have sprung into action to help. There’s Relay Rides, Get Around and Zip Car to share your physical car. Sidecar was the first company to introduce on-demand peer-to-peer ride sharing. You’re not giving your keys to someone else, you’re having someone hop in your car with you.

There are emerging trends that show more people are returning to urban environments and cities from the suburbs.

How has technology paired with heritage as the move towards the center of the city interacts with older transportation infrastructure?

In urban planning there’s something called the last mile, which means a train or bus can get you near where you need to go, or your house, but not right to the doorstep. This is where technology and Sidecar can really fit in and create more options and opportunity to get around. It fits well with the existing bus, train and transportation infrastructure as well as biking and walking. It’s all about increasing options and accessibility.

How do you see people connecting in urban communities in the future? How will people be able to foster community through technology?

think on-demand location-based technology that connects people with shared interests or a shared outcome - like getting from point A to point B can definitely help facilitate community. 

In San Francisco for example, we have people who turn Sidecar on as they drive from Oakland or San Jose to the Peninsula. As a Sidecar driver you can pick up someone in your neighborhood who is going to the same destination as you.

We’ve heard tons of stories of people getting to know each other on those drives. Some drivers have exchanged numbers and make business contacts. Sometimes I drive as an actual Sidecar driver as well. I picked up a passenger who had just returned from Korea. He was craving an In-N-Out burger and wanted to go to a drive thru. I hadn't had lunch so I suggested we should just go in and eat there. I made a friend. He was running another company, I gave him some advice and he gave me some business advice too. We’ve stayed in contact ever since. 

How is Sidecar different from other similar companies?

Sidecar uses real local drivers, just everyday people in your neighborhood. Some of the other services use professional drivers, black cars and SUVs, or taxis. Another big differentiator is that we have ‘destination’. Both passengers and drivers can say where they’re going so you can be matched with people going the exact same way as you. We’re also a rideshare marketplace so drivers actually set their price. If you’ve got a bigger car that uses more gas, you can charge a little more, if you’ve got a compact car you can charge a little less. We give full control to the driver. We also give full control to the passenger. The passenger can pick the exact type of car they want, it shows all the cars available in the area, their ETA and ratings. They can even see the face of the driver and photo of the car. There’s full transparency at every step.

You’ve personally been involved in a number of entrepreneurial companies. What advice would you give to someone wanting to start something themselves?

My advice would be to start small. A lot of people get this idea in their head... "If only I had 14 programmers and $10million in venture funding..." But you should figure out how you could set it up this week. Start small. Use friends and family. 

A lot of people get this idea in their head... “If only I had 14 programmers and $10million in venture funding...” But you should figure out how you could set it up this week.

There’s a great book called The Lean Startup. It’s all about starting small, testing, getting a feedback loop and continually iterating. That’s how you can build something big without spending lots of money creating something people don’t want. 

Whenever I have an idea, people push back at me saying, "How can you hack it together in a cheap and dirty way? Then go and spend the money and build it out."

A lot of people start something by doing it small and by hand. Think about Amazon’s Jeff Bezos.  He literally had the books in his garage and was shipping them out by hand. He didn't start with a warehouse. Don’t put the cart in front of the horse. 

Can you give an insight into a typical day at a startup?

The most typical thing about a start up is that it never stops. You have a lot of passionate people, but because you're a start up you're under-staffed, under rescued and everyone works their butt off. But, it's really rewarding because you see direct results from your actions. It’s not like a large, 50,000 person company where you’re a cog in the machine. You want to write an email? You write it and send it to all your customers. It’s pretty quick.

I tend to wake up and check emails. A lot of our programmers work late into the night and as Sidecar functions 24/7 there are always emails first thing about what happened last night, or programming issues. I then check my Google Alerts to see where our company, and our major competitors, are mentioned online. I check out the news on Valley Wag and Tech Crunch. After emails and intel, I work on anything from analysis, brainstorming our next promotion, figuring out marketing plans, or a little bit of ops. There’s a lot of Google Hangouts too!

You’ve had a lot of experience in different contexts and countries. How have you discerned each next step and what advice would you give to someone trying to carve out their career path?

There are two things. 

Firstly, know you end destination - where, who and what you want to be and do. Keep that in the back of your mind. 

At the same time, be able to live in the tension of not knowing what’s going to happen a month from now- especially if you’re working at a startup where products and contexts can pivot so quickly. Full disclosure… if you choose to work at a startup, you have to be ok with a lot of ambiguity and be able to live in the tension of the unknown!

I also think employing discernment at each step and seeing what doors open is important. I tend to find the same conversations happen again and again if you’re supposed to take notice.

I also think employing discernment at each step and seeing what doors open is important. I tend to find the same conversations happen again and again if you're supposed to take notice. 

Some people call it chance, I tend to call it signs that I should be moving one way or another. But, I know where I want to be and what I want to do.

I want to work at a company of organization creating a better culture that leaves the world a better place than when I came. Impacting cities is also important for me. Right now I’m in technology and transportation and I love it, but knowing my end goal gives me the filtered focus to decide my future steps.

 

For more information visit https://www.side.cr

 

Image credit: Yvonne Goll (top) also courtesy of Sidecar