附近上门

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聽附近上门 News has聽learned about the CTO and technical Co-Founder of . 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鈥攚e’ll call it Season 2.5鈥擫eonard 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鈥檚 hard when you鈥檝e been doing the same thing, in spirit at least, to think what else you would be doing. So it seems likely I鈥檇 be doing something similar, you know? Another startup trying to help people.

I think one thing that I probably wouldn鈥檛 do is start with a business that requires so much people coordination. There鈥檚 a lot of people out there鈥搕he taskers and the clients鈥揳nd real-life is really challenging. So it鈥檚 a really hard problem. I think I鈥檇 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鈥檙e going to build and just speculate on it. I鈥檇 much rather be with a team building it and seeing what it looks like. Planning is a necessary step, but I鈥檓 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鈥檚 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鈥攕tep 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鈥檝e been acquired by IKEA I鈥檝e been flying back and forth to Sweden and the Netherlands and lots of other places. I鈥檓 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鈥檚 a joke I have whenever I start talking about a book. Basically, I鈥檓 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 聽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鈥檚 going to work or not. It comes and goes. We raised a bunch of money, and we鈥檙e trying to do this thing. Success usually means getting acquired or something like that. But for me it鈥檚 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鈥檚 college, they took trips that they wanted to take, they paid their rent鈥攅ven 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鈥檛 see a path forward. If somebody says 鈥淲hat next Brian?鈥� and I don鈥檛 have the answer. I like to have the answers.

What buzzword is exhausted?

I think that maybe 鈥渂ig data鈥� is over. I鈥檓 not sure we have 鈥渂ig data.鈥� Maybe we have 鈥渕edium data.鈥� It鈥檚 really what you do with that. We could store extra stuff probably and have 鈥渂ig data,鈥� but it鈥檚 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鈥檝e been listening to and went to Hamilton. I want to work in a way that I enjoy that. So I鈥檓 thinking Thomas Edison鈥攖he inspiration and perspiration kind of idea. You know things are hard, and you might have an idea, but it鈥檚 really about the execution of that idea.

What impact do you want to leave behind?

That鈥檚 straight out of Hamilton there!

TaskRabbit鈥檚 mission is making everyday life easier for people. The future of work is inevitable, and we鈥檙e in the position to decide what that looks like. I鈥檒l 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鈥檓 gone, if not already, I鈥檝e 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 鈥淚 went up the stairs,鈥� 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鈥檛 really progress鈥攊t was forcing technology onto a situation. I think something we鈥檝e done at TaskRabbit is we鈥檝e 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.

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