In that situation, lots of other entrepreneurs might take time off to travel, or become an "entrepreneur in residence" at a college or investment firm.
Pepper decided to become a part-time Uber driver. (Uber is a transportation service that lets you summon a range of vehicles, from taxis to SUVs, using a smartphone app. The drivers are all freelancers.) He's done almost 50 rides so far, in his Jeep Wrangler and his Tesla Model S electric sedan. Often, he picks up Uber passengers after he has dropped his kids off at a Cambridge private school. Yesterday, he said he drove seven hours non-stop, until his wife called and asked him to "stop Uber-ing."
I asked him what he's been learning. He also shared a short video, which you can see below.
Q. So what made you want to do this?
A. I've always had this impulse to just leap, to keep things interesting, do things that might provide a different perspective. My friends are like, you are absolutely out of your mind. But I've always told people, if I wasn't in the burrito business for the last 17 years, it would have been transportation.
Q. So you started driving right after you'd resigned from Boloco.
A. I got into an Uber with a guy named Shabih. This guy was the first guy I spoke to on the first day of the rest of my life. I didn't give it five seconds thought. It was October 7th, after a three-hour meeting with my investors the day before. He told me he would get $250 if he referred a new driver to Uber. So my goal was to get my guy $250. It would feel good, like good karma. Even though I was tempted to blow it off, I wound up going to a company training session in late October, at a Holiday Inn in Dorchester. They never looked at my car.
Pepper talks about the training session in a blog post he's writing about the experience:
We were instructed on the basics of being an Uber driver. It lasted 20 minutes. What followed was the most brilliant 40 minutes of Q&A I’ve witnessed. Whatever it is that was actually asked, I came away from that short session with only a few takeaways. I hope it was intentional.
1. Never, ever try to call Uber with problems… because they don’t even have phones and there is very little if any reason to talk to them.
2. The customer is always right; and on that note, default to giving them a 5.0 rating.
3. Uber takes their rating system very, very seriously. Stay above a 4.5 rating and you’re fine. Fall below and you face removal from the system. No stories. No excuses. No phone calls.
As I got ready to leave the “training” program a few minutes early (I had a date with my wife), they snapped my mug shot, issued me my phone, a minute of friendly chit chat, and off I went.
Q. Did you sign up because you wanted to learn about Uber?
A. Whatever business I do next, there's a lot to learn from their model. Wherever possible, they leverage skills we already have — people already know how to drive. They set very, very clear expectations as to what constitutes success, and then they follow through with the metrics. There are no stories [from drivers] — they don't want to hear why this customer was wrong, or that customer was crazy. There are these things that are rigid and effective, but I think they could really effect the world of restaurants and retail.
Q. I assume you've been following the debates about Uber's surge pricing [when they increase fares at times of high demand, like during a rainy rush hour.]
A. What you've got is a very fluid, liquid market. If they create these barriers, like surge pricing, there's going to be less trading. We assume they've got it all figured out. But like anything, there's trial and error. It's still not tried and true. The [surge pricing] is really area-specific now — drivers can see on their phones that there is surge pricing in effect in particular areas of the city.
Q. You write a lot about the ratings that customers give drivers, and how they made you pretty anxious.
A. Right now, the review process of employees is pretty broken in corporate America. Most of us have read Jack Welch's book about how GE was so diligent about ranking people. But it's hard to give fair and just performance appraisal. At Uber, they're not evaluating drivers in that way. The drivers are being evaluated by someone who sees the full experience from start to finish. There's no conversation to have, no discussion. It's very compelling. People know moment to moment that they're being evaluated. It becomes a norm, not a stress point. The good people surface to the top, and the people who can't deliver consistently good service don't make it. But they definitely expect the customers to weed out the bad drivers.
They take a risk on the first 40 rides. They say, we're not going to look at your ratings. If you're at a 4.2 or 4.3 [out of 5 stars], I don't think you're going to get kicked off the system then. I'm at 46 rides. After 40 rides, that's when they say, you're below 4.5 and you're out. [Other drivers have confirmed this to me.]
Q. You write in your post about the one night you decided to drive — drunk people, couples making out in the backseat, getting a bit lost in Bay Village.
A. That was a week ago yesterday. It brought me to my knees. I was at a 4.3, and if you're at that level, you're done. That night, most of my passengers had been drinking heavily.
A. I have two different cars. I didn't use one until after that night. I was using a Jeep Wrangler. Today I did 15 or 16 rides in my Tesla. (A Tesla Model S is pictured at left.) The social dynamic is totally different. In the Tesla, it's an equal conversation: "What's going on here? You have a Tesla and you're driving an Uber." For the last 23 rides, I have a perfect 5.0 score.
Q. Were you ever scared or worried about who was in your car?
A. I was never scared. It has felt awkward sometimes, when people are super-silent and you're trying to read it. I'm used to being in the backseat [as an Uber passenger], and I'm often there with my laptop clicking away — I've got to get some work done real quick. But I do sometimes think, "Maybe I need to fill this space with chatter." [Pepper says he has spent more than $5,500 using the Uber service as a passenger.]
Q. Tell me about what you've been making.
A. I was out yesterday, and I missed the peaks [when Uber charges a higher rate]. I made $190 working 7 hours, minus Uber's 20 percent. That's about $21 an hour. I went on at 8:30 AM and was done at 3:30 PM. Maybe it was a big day, because it was the day after a snowstorm. I did get some rides when surge pricing was on — one for 2 times [the normal fare], and one for 1.25 times [the normal fare]. Sometimes it doesn't feel very good when you're actually doing it, but at the end of seven hours, it added up.
Q. Does it feel like it would be a good job?
A. It's very free. You can do nine hours, and stop on your own time, and not work the next day. There's value to that flexibility. They're guaranteeing $20 an hour at times, and I happened to make about that even when there wasn't a guaranteed rate. I worked when I wanted to, and didn't work when I didn't want to. That sounds pretty good compared to working at a fast food restaurant, making $10, and not being very in control of your life.
Q. Did your passengers believe that you had been the CEO of Boloco? Did they think you were doing "Undercover Boss" or something?
A. I told them that I'm doing it because I wanted to do it. I'm pretty transparent. Sometimes I told them it was an experiment to understand the way the business works.
Q. Are you going to keep doing this forever?
A. My goal was to get my guy $250. But it feels really productive to take my kids to school and get paid to drive home. I get to see the other side of a consumer technology business that I really like — I'm motivated and inspired by it. But I'm also taking away from my ability to meet with people, or write the book that I want to write — all these other productive things I want to do.
But I will admit that I enjoy it, and I have met some super-interesting people. I probably have ten people who reached out to me afterwards, wanting to talk to me about their startup or whatever. The story of Boloco often comes up — one of my license plates says "Boloco." I'm not hesitant to give out a free burrito [coupon] here and there.
I think going forward, I might still dabble in it... I have a meeting coming up in Kendall Square, and I may Uber back. I may get in the car and see what happens.
About Scott Kirsner
Scott Kirsner was part of the team that launched Boston.com in 1995, and has been writing a column for the Globe since 2000. His work has also appeared in Wired, Fast Company, The New York Times, BusinessWeek, Newsweek, and Variety. Scott is also the author of the books "Fans, Friends & Followers" and "Inventing the Movies," was the editor of "The Convergence Guide: Life Sciences in New England," and was a contributor to "The Good City: Writers Explore 21st Century Boston." Scott also helps organize several local events on entrepreneurship, including the Nantucket Conference and Future Forward. Here's some background on how Scott decides what to cover, and how to pitch him a story idea.
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