Proust Goes Tech With Brian Leonard, CTO Of TaskRabbit

Brian Leonard hasn’t purchased a t-shirt in years.

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Why? His closet is stocked full of 100-plus (mostly) startup t-shirts that he has accumulated working in tech. That’s not the only thing Crunchbase News has learned about the CTO and technical Co-Founder of TaskRabbit. He went a summer without wearing shoes (apparently the freezer aisle in the grocery store is very cold), he’s a lucky charm for baseball teams (in every city he’s moved to in the past fifteen years the team has immediately won the World Series), and he loves Vietnamese food.

In this episode of Proust Goes Tech—we’ll call it Season 2.5—Leonard spoke about his lack of patience, his admiration for his wife, and the historical figure he most admires.

What would you otherwise be doing right now?

It’s hard when you’ve been doing the same thing, in spirit at least, to think what else you would be doing. So it seems likely I’d be doing something similar, you know? Another startup trying to help people.

I think one thing that I probably wouldn’t do is start with a business that requires so much people coordination. There’s a lot of people out there–the taskers and the clients–and real-life is really challenging. So it’s a really hard problem. I think I’d get started on an easier one for the next one, and then see if it could grow into a harder one.

What is your main fault?

Impatience. I took a long trip in Vietnam as a vacation. Even then, I was trying to impatiently optimize every moment. My wife reminded me of that several times.

What do you most desire in a tweet?

A good tweet has a good pun.

What is your idea of misery?

My idea of misery is a whole day of meetings where we talk about what we’re going to build and just speculate on it. I’d much rather be with a team building it and seeing what it looks like. Planning is a necessary step, but I’m always impatient to get started putting it into true existence.

What do you appreciate most in your friends?

I really appreciate with my friends that we can be real with each other with our challenges, with our joys, and not always be up and to the right like so much of Silicon Valley culture.

What is your chief characteristic?

Seeing something that should exist in the world. That’s a very visionary sort of thing. But my chief characteristic is seeing that and understanding and coming up with the steps to try it out iteratively—step by step. I think that the vision changes as we learn things, but the ability to always take a step in the right direction.

What skill do you wish you possessed?

Since we’ve been acquired by IKEA I’ve been flying back and forth to Sweden and the Netherlands and lots of other places. I’m an elite member in the frequent flyer programs all of the sudden, and I wish I possessed the ability, like our CEO Stacy. She seems to be able to take a redeye and arrive and be good to go. I wish I possessed some more ability to travel without the effects. But I get worn down very quickly.

What is your most impactful book?

There’s a joke I have whenever I start talking about a book. Basically, I’m heavily influenced by whatever the last book I read is. So recency bias or something like that.

A book I recently read, which I think really applied to TaskRabbit, was called Play Bigger:How Pirates, Dreamers, and Innovators Create and Dominate Markets by some category designers. It was about how to create your own category and then work to be the king of it.

What defines success for you?

With startups, you never know if it’s going to work or not. It comes and goes. We raised a bunch of money, and we’re trying to do this thing. Success usually means getting acquired or something like that. But for me it’s like, even if we fail, we would have distributed that money effectively to people doing the real work. There are people in San Francisco with real skills, not just typing skills, people who can actually build things with their hands. They paid for their children’s college, they took trips that they wanted to take, they paid their rent—even in San Francisco. In the process, we also helped a bunch of people who needed things done, and made their lives better, too. So seeing that is a success in my mind.

When is confidence lost?

I think confidence is lost when you can’t see a path forward. If somebody says “What next Brian?” and I don’t have the answer. I like to have the answers.

What buzzword is exhausted?

I think that maybe “big data” is over. I’m not sure we have “big data.” Maybe we have “medium data.” It’s really what you do with that. We could store extra stuff probably and have “big data,” but it’s really about how you act on it.

What virtues do other people have that you do not?

I really admire my wife and how organized she is. I more or less take things as they come, as evidenced by this interview; I make it up as I go along! Her organization and preparation more or less allow us to be effective as a family unit. I think everyone needs to either have that virtue or find somebody that does.

Which historical figure do you most admire?

I’ve been listening to and went to Hamilton. I want to work in a way that I enjoy that. So I’m thinking Thomas Edison—the inspiration and perspiration kind of idea. You know things are hard, and you might have an idea, but it’s really about the execution of that idea.

What impact do you want to leave behind?

That’s straight out of Hamilton there!

TaskRabbit’s mission is making everyday life easier for people. The future of work is inevitable, and we’re in the position to decide what that looks like. I’ll be really proud if the model that we come up with continues to change how work is done in this world.

I also hope… by the time that I’m gone, if not already, I’ve instilled in [my children] a sense of helping others and working hard and, in general, just being good people.

What is the biggest problem tech is failing to solve?

There are so many people in Silicon Valley in general that equate technology with progress. We have a fitness program at TaskRabbit. Every day that you go up the stairs you put a tick market next to it that says “I went up the stairs,” and you get points and you can do stuff with those points. And it was progress when we made an app for that, but no one really used the app. So that wasn’t really progress—it was forcing technology onto a situation. I think something we’ve done at TaskRabbit is we’ve tried to find the right places to use technology, but also allow human-to-human relationships to play out amongst the people who are using our product.

Illustration Credit: Li Anne Dias

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