- Yale undergrad
- White House
- Founded Thumbtack
Q. Tell us about your background.
A. Yep, so I grew up in the Midwest, and then moved out to Connecticut for Yale. I studied Philosophy, Politics and Economics, and then my first job was a self-made job. I started a non-profit in college, as you said, which was a student advocacy group on the issue of social security, which was very dorky, but I loved it.
And then after college, I moved to DC and worked in the White House, where I worked in the West Wing, covering economic policy — so financial markets, taxes, entitlements. And then after the White House, I moved to San Francisco to start a tech company with some buddies.
Q. Tell us how your career path has taken you to your current role.
A. Cool. So, when I was growing up, I was always a big political junkie, so when I applied to college and they asked you, “What do you want to be when you grow up and you graduate from college?” I said I want to work with the President’s economic advisors. That was my dream, which might be a weird dream, but I was really excited about it. I think economics is a very powerful tool to bring prosperity to millions of people, and I also love politics because it brought economics to the real world.
So when I was in college, I studied a major at Yale called PPE, which was philosophy, politics and economics. It was marrying both the politics and philosophy that I loved with economics. So, when I was in college, during the summers, I’d look for summer internships that could get me involved in politics because I knew no one in DC.
So, one summer, I worked as an intern at a think tank, which was basically just a combination of public policy and academia. Then the next summer, I applied to work as an intern at the White House, and I got rejected. Then I applied a second time. I got rejected the second time. In my third time, I was accepted, which was just awesome.
I took a semester off in the fall of 2004 to work in the National Economic Council of the White House. The National Economic Council develops all the economic policy for the President. So they have economists and policy makers who focus on all sorts of financial markets, entitlements, healthcare, social security, foreign policy. I got to work there for a semester, which I loved, and was completely fascinating for me. At the end of that semester, I was actually offered a job. They asked me if I wanted to drop out of school, which I thought about doing, but I decided to finish.
Instead, when I got back to Yale, I was very engrossed in the social security debate, so I started a non-profit that got kids involved in the social security debate. So, we had rallies and wrote op-eds and went to DC. It was a way for me to stay in politics while I was back at school.
After college, I went to DC to run that non-profit and then eventually, the White House made me another offer. I was very lucky and I went to work at the White House full-time.
Q. How did you transition from the White House to Silicon Valley?
A. So I always liked creating things. At the non-profit, what got me so excited was I could bring an idea to reality. So in the social security debate, it was lots of talk about people who were retired and what social security meant to them, but there was very little discussion about what it meant to people our age who were paying into the system. So as an entrepreneur, that seemed like a vacuum to me, so I wanted to make the debate more balanced.
So my idea was just to bring students to the debate and there was nothing more satisfying than having this idea and then, a year later, see ten thousand students across the country advocating on social security reform, which is a very wonky subject. So, it was a very satisfying, exciting experience for me. I decided that I wanted to do it again, and so, towards the end of my tenure at the White House, I got permission from the White House to start a company on the side.
I didn’t have very much free time, but I spent one night every week brainstorming startup ideas with a couple friends who’d been involved in the non-profit with me. And our only requirements were we wanted to start something for-profit, and we were thinking consumer web, but that was basically it.
And so every week, we’d brainstorm ideas for an hour, and lots of them were really bad ideas, but every once in a while, we’d have an idea that we were excited about, and one of us would start researching it, seeing what competitors there were, what the opportunities were, and we went down various roads. Many were dead-ends, but eventually we came to what became Thumbtack.
Q. Where did your interest in social security come from and how did it turn into the non-profit you ran after college?
A. So, my boss at the White House was the expert on social security. And so I worked with him, and he made me a devotee of his, basically, and he’s now trustee of the Social Security Administration, so he’s still working on social security.
After I left, there were two motivations – one was I was truly inspired by him and the system was broken, and I wanted to be involved in helping him fix it, but a selfish motivation was I really wanted to work at the White House again. I knew if I got involved, this could be a way I could impress my boss and show my devotion to this subject, and I hoped that in future years, he might look kindly on that and say, “Hey, you should come back and join us.”
So, I started by — I found a friend who was also interested in the topic and we started talking about it. We hired a friend to help make us the website. And then, the first thing we did was reach out to other groups we thought would be helpful.
There are a myriad of non-profits and advocacy groups in DC that are always there, and they’re often changing their name based on the new debates or new topics. But the donors tend to be the same and the people organizing tend to be the same.
And so, I sent an e-mail to dozens of people, and this is probably a trait of mine that’s been very helpful throughout my career: I’ve been very shameless in asking people for help. I sent a few dozen e-mails, and I’m sure most of the people ignored me, but a number of people responded and said, “Yeah, this is awesome. You guys want to start a student advocacy group. We’d be happy to help you.”
So, I went to DC, and there is a meeting in DC called the “Wednesday morning meeting,” and Grover Norquist puts it on. Some people talk about the right-wing conspiracy – about how organized the right is. This is actually like the definition of the right wing conspiracy. You walk into a room and, every Wednesday, all the important donors and advocacy and think tank people from the right wing meet in one room and they coordinate and they share their information. They talk about what issues matter to them.
And so, I was invited to speak at this meeting. I had no idea what I was walking into, but I just said “Hey, I’m Jonathan. I think social security is an important issue, but the youth aren’t represented. I would like to represent them with this non-profit I’m starting with a friend, and here’s what I’m looking for help on. I need someone to give us money so we can hire some programmers. I need e-mail lists so I can reach out to people on college campuses.” I listed 5 things.
And right after that meeting, a group of two dozen people came around me and said, “We want to help you.” And they all offered various things that helped us, and so that was the very beginning of getting us kick-started. And from there, it was just marshalling the resources and taking advantage of all the help we were offered.
Q. What was the mission of your non-profit?
A. So, there are two problems with social security. One is that its finances are broken and it’s running out of money, and two –this is a more subjective problem I think it has – but there is no ownership in social security, so you pay into the system and the money is handed to the next generation.
But I believe the system would be better and more empowering if people put their money into an account that they actually own. So today, if someone dies and they have not collected social security, the money they’ve put in they can’t pass to their children. And they also can’t see the money they’re putting in, the return on investment on what they’re saving toward.
I thought at the time that this ownership component was probably the most important thing. But now, I think that the broken finances is probably the most important problem, so our group advocated for fixing the social security program in a way that was equitable for our generation, which basically meant that, in the past, social security has always been balanced just on the backs of young people, because older people tend to vote more. And so, it’s very easy just to always give more and more benefits to older people and raise taxes on younger people. So our proposal was that it should be a more balanced solution and all generations should share in the sacrifice.
So what we succeeded in doing was activating lots of students. We had ten thousand students on campuses in all 50 states who would write op-eds and hold rallies, and we went to the White House and had meetings there. We got to have conference calls with Karl Rove and other people, which at the time was really exciting for us.
At the end of the day, social security was not reformed. So in that, we failed, and social security still hasn’t been reformed and people are still fighting this battle. So, had things turned out differently, we could’ve played a part in the reform of social security, but unfortunately, we did not.
And that’s just a brutal reality of politics. It is such a huge machine. You can do everything right, but you cannot determine the final outcome.
Q. What did you learn from this experience about how to effect change successfully?
A. That’s a good question. I don’t know if there’s anything we could have done differently in the short-term.
The big players like the AARP have organizations that have hundreds of millions of dollars of revenue to spend on this sort of thing, so it’s not something we could compete with. I think in the long-term, the way to compete is to create a student advocacy group that’s not dependent on volunteers.
So, the AARP has hundreds of millions of dollars because they sell services and products to retired people, and then they use that money to hire armies of people to advocate on their behalf. But student organizations tend to be volunteers – like “Rock the Vote,” where they play to the best instincts of young people, but people’s best instincts are very unreliable.
And so, I think creating an AARP for young people, where you actually sold group memberships or supplies or products, I’m not sure exactly what, but you have a real for-profit business underlying it, and then you took those revenues and reinvested them in an advocacy — I think that’s a much more realistic model for getting young people involved and actually making a change.
Q. What specific things did you do to then become Deputy Associate Director of the National Economic Council?
A. So I think it’s some combination of perseverance and scrappiness, and some combination of knowing the right people.
When I first entered the political scene, I knew none of the right people. Like I said, I applied to the White House three times, and the first two times I was rejected, and the third time I was accepted.
I don’t know if it was because it was the third time, or because in the meantime, I had purposely looked around for people who had access to the White House, who had worked at the White House, or who knew people at the White House.
By the third time I applied, I had letters of recommendation from people who knew people in the White House, and I think that makes a big difference.
Having worked in the White House, it’s very much a meritocracy inside, which is a beautiful thing. If you make a line from the Oval Office to people’s offices in the West Wing, and you measure that distance, there is definitely a direct correlation with IQ, and that’s pretty cool.
But in order to get inside the White House gates, there is some element of being connected. There are, as you said, hundreds of thousands of people who would love to work there. There’s no way you can sort through all of those people without saying, “Oh, do you know this person?” “Oh, do you recommend them?”
And so, I think you have to be realistic and you have to do your best to make yourself known or meet people who know people, so you can get the right introduction.
Ultimately, you have to earn the position, but in terms of getting the interview, I think you have to be a little scrappy about it.
Q. Did you apply formally for your full-time job at the White House, or did you know enough internal people from your internship that it was just informal interviews?
A. Since I had my internship there, that was basically a semester-long interview. And I made sure I was the first one there, and I would be the very last person to leave. Even if I had nothing to do, I would stick around because I knew I was so close to an opportunity that I had dreamed about, that I was willing to do basically anything.
And so, I worked really hard. I made sure to become good friends with my bosses. And then when I returned to Yale, I stayed in touch in the meantime, and through the social security non-profit, I was able to stay more than in touch. I actually came to the White House a couple of times and got to meet with people again.
Then, when I graduated, I told my boss that I was looking for a position, and one opened up soon after, and I was brought in for an interview with his boss. But I think at that point, I basically had the job, because I’d proven myself to the person I was going to be working with, which is most important. And so, I think I could have still messed it up at that point, but I fortunately did not.
Q. What were your responsibilities day-to-day at the White House?
A. It depended a lot on the time and the year, based on whether Congress was in session or whether we were pushing for a bill.
My job consisted of a few things. One was policy work — so Excel and research and doing data analysis for my boss. Another part was events. So, when the President is advocating, for example, President Obama was advocating healthcare reform, he would have events all around the country to spread his message about why his bill was a good thing for the country. And those events are organized by a department in the White House, and they’re organized in conjunction with my department.
So, I would sit on the phone with Americans, and I would call them from the White House and say, “Hey, we’re calling from the White House. President Obama is interested in talking to you about healthcare. Are you interested in that?”
And people would often be stunned and say, “What house?” and we had to give them the phone number of the White House operator, and then they’d call back just to make sure that it was the real deal. And so, we were partly seeing if they’d be a good fit for the event, because these events are PR events, so you want them to reflect well on the administration, so you want to make sure that you’re on the same page.
So, I would do that sort of thing. And then, towards the end of the administration, I moved to the West Wing, which was very exciting for me. I was on the second floor of the West Wing, outside of my boss’s office. And I was kind of his aide. So I would do many sort of miscellaneous projects he needed.
At the end of the administration, it was the economic crisis, and in the summer, we had Fannie and Freddie, and then, Lehman, of course, in September 2008.
We had a Bloomberg terminal in the West Wing, and I became the expert on the Bloomberg terminal. So, I would get into work at 5:00 a.m. in the morning. I created a report on what had happened in the markets overnight, and I would get that to my boss and the other economic advisors, and it would also be sent down for the President to read in the morning when he got to his office.
So, that was cool. I was certainly not making any big decisions, but I got to be near lots of big decisions being made, which for me was very exciting. I got to sit in meetings with Chairman Bernanke and Secretary Paulson and my boss, who was the President’s economic advisor, and hear the discussions about what bills are being considered and what tactics are necessary to advance different bills.
Q. What was the most insightful or surprising thing you learned at the White House?
A. There are a couple people in the West Wing who I especially respected, and I asked them both, “What did you do to get where you are today?” and they both said something that is maybe not that surprising, but I think most people don’t appreciate. They both said, “We just read the reports that no one else read.”
So, there’s one person I worked with who reported on Fannie Mae and Freddie Mac, and he was widely known in the West Wing because he basically predicted Fannie Mae and Freddie Mac’s problems many months before everyone else did.
He was, like, “I just read the reports, and I read every detail.” And most people never did that. And so, basically, he said “I just did the work.” Most people were much too superficial, but he really dug in and knew it like no one else, and really learned and appreciated the depths of the data, and that goes a long way in the policy world.
It was not something I was especially excited about. To really have that expertise, you have to commit yourself solely to a single subject for many years, which I found a little too narrow for me, but if that is something you aspire to, I think it’s very good advice.
Q. When you say they dug in and did the work and read the reports, you’re not saying a couple months of reading about a subject; you mean dedicating your career to it, right?
A. Yeah, exactly. So, if you want to be a policy advisor on social security or on Fannie Mae or on agricultural policy, the guys who are good dedicate their entire life or decades. And maybe it doesn’t take that long to become an expert. It only takes a few years, but the guys who are really good have been doing it forever, and it’s pretty amazing.
Q. Would you say much of Washington is characterized by superficial analysis, like reading a Wall Street Journal analysis or a New York Times analysis but not much else?
A. Definitely. I think that’s true of all industries, though. I think it’s true in the startup world. I think it’s true everywhere. It’s true in journalism generally.
One of the amazing things working in the White House is being in the West Wing, and my boss would walk out, and I’d see him walk out. And then, I’d look up on CNBC and I’d see him walk in front of the camera, in front of the White House and he’d be talking, and then he’d walk back in. And they would be commentating on what decisions were being made in the West Wing or what was or was not being said, and they were often just completely wrong, and it was pretty comical to hear people on the news or in newspapers speaking with such authority about what was happening, and knowing for a fact that it was not true.
Q. So it sounds like to be an effective thought leader, you really have to decide what you’re going to commit to and spend years developing expertise on it.
A. Yeah, definitely. I don’t think it has to take forever. I think it just takes dedication for weeks and months. It doesn’t necessarily take decades, but I think most people don’t even put those weeks or those months in.
Q. You mentioned you worked in one part of the White House and then moved to the West Wing. What does it mean to “work in the West Wing” in Washington speak, and why is that significant?
A. In Washington, especially the White House, your proximity to the Oval Office is your proximity to power and to important decisions and to prestige. It’s the same on Capitol Hill. Your proximity to the majority leader or the Speaker of the House is your proximity to power. You often hear people say, “I work for so and so.” For me, it was very exciting because I got to be closer to lots of the big decisions and the big meetings.
So, in the West Wing, I think when I was there, there were maybe 60 people who worked in the West Wing, and then there’s the Eisenhower Executive Building, which is across the parking lot, which probably has a thousand. And then, there are two other buildings that hold a few more thousand people.
The closer you get to the West Wing, the closer you are to just happening to walk by Condoleezza Rice or the Vice President, or you get invited to the Rose Garden for a speech, or to the South Lawn for the Queen’s arrival.
And the proximity to just amazing things like that — it was a very special experience. I would wake up absurdly early every day, and I remember almost every day walking into the West Wing, and I’d say, “Wow, this is a moment I should cherish because it is just incredible.”
Q. What were your work hours like?
A. It was pretty long. I would wake up at 4:45 a.m., and I’d try to get to work at 5:30 a.m., and then this was during the financial crisis when I’d try to get there early to create economic reports. And then I stayed throughout the day and ate lunch and dinner there, and then I’d stay as late as my boss would, which would be normally 9:00 p.m. or 10:00 p.m. or 11:00 p.m. or midnight. And so basically, I did nothing but just go to work and then go home to bed when times were busy.
There were times that were slower. During August recess when Congress was out, you could go home a little earlier. And there were times where I was at work and I didn’t have a lot to do, but I had to be on call.
Sometimes I’d be sitting at my desk and I finished my projects and I wouldn’t have anything for a little bit, and then my boss would send me an e-mail and he would say, “Hey, I’m in the Oval Office. How many employees does Ford Motor Company have? You have five minutes, I’m about to tell the President.”
Or, he’d walk out and say “Hey, I’m not going to give this speech. I’m too busy. I have a conflict. Could you go speak to the Mississippi Banker’s Association.” I’d think, “Oh crap, I have no idea what I’m gonna say.” But then I’d have to figure it out.
And so those moments were, for me, very exciting because I really like being challenged and being pressured. And for me, under pressure, I focus and it’s not stressful, which is very exciting. And so, the West Wing really challenged me and made me do things I didn’t know I was capable of, but that’s a very satisfying feeling.
Q. Sounds like you even got some speaking opportunities too.
A. Yeah, very few, unfortunately, but a couple.
Q. What role does partisanship play in getting a job at the White House, or the West Wing, if at all?
A. There were no very liberal Democrats in the West Wing. And in Obama’s West Wing, there are no conservative Republicans. And so, you do have to be in the right group in order to be included.
That said, I didn’t find the West Wing very partisan in the way that I think Capitol Hill is. Capitol Hill has to represent more narrow interests. You have representatives or senators. And representatives often represent a few hundred thousand people. A single big army base or a single big company can have lots of influence.
The West Wing looks much more broadly. We represent the whole nation. So my boss saw his job – he would open the Wall Street Journal or the New York Times, and any economic issue was something he had to think about.
There were so many constituencies that both will love and hate you no matter what you do that there was this feeling– at least from all the people I was exposed to – that we should just do the right thing for the country.
And especially toward the end of the administration, President Bush was not especially popular, and so I think in some ways that was freeing, and people in the West Wing said, “Look, there are lots of people angry with us for different reasons.” The economic crisis was a surprise for lots of people in Wall Street and in DC, and so they said, “Look, we just have to do what we think is the right thing.”
And so, I found that very uplifting to see very smart people just trying to do what they thought was the right thing. In that way, it wasn’t partisan, but there weren’t a lot of Democrats around the table either.
I think there were lots of people who would consider themselves libertarian or moderate, which I consider myself. And I may disagree on social issues, but if you’re in the economic office, you just don’t talk about those things, and you just focus on the issues at hand.
Q. So, more of a “let’s get to the right answer” approach than “let’s increase the size of my pie for my district”?
A. Oh, yeah. There was definitely none of that. That would be seen as unpatriotic and inappropriate to talk about.
Q. What was your biggest life lesson from Washington that has influenced you?
A. The things I found uplifting were the meritocracy of the West Wing. If you were there and you knew the answers better than everyone else, you were going to be promoted, and you would have more responsibility.
There were people there who just knew their stuff in a way that, if you were in a meeting, people would just turn to you and say, “Well, let’s defer to this person on this topic because they know what they’re talking about.”
I saw that as very inspiring. Of course, you had to be able to get into that room, which took some scrappiness, but once you were there, there was no faking it. It had to be real, and I really liked that.
The other thing I found, which I don’t think I discovered really until the end of the administration, was that you really could create your own role for yourself if you want. People often just do what they’ve been dictated to or what their direct responsibility has been, as narrowly defined, but I think it’s true in other organizations and I think it’s true in the White House: if you really want to take on new responsibilities, you can just do it.
If you go out there and ask for more responsibilities or you just start to do it, if you do a good job, people are happy to give you more responsibility. And so, I think that’s a good life lesson, and something I’ve taken with me. Just be scrappy, and if you want to do more, go for it. If you do a good job, people are going to love you for it.
Q. You then left the White House. President Obama was elected. How did you then start what eventually became Thumbtack?
A. I started working on brainstorming for Thumbtack in 2007 or 2008, and as I said, I spent every week thinking about it.
Our first idea that we got excited about was what I call a financial integrator. I would go into my mailbox, and I would get a letter for my student loan and a letter for my credit card and a letter for other finances. And I thought, it makes a lot more sense if this was all combined in one system. And so, we started thinking about this idea more rigorously and we wrote up a business plan.
Then Mint.com launched, and they basically had exactly the vision we were thinking of. And so this was a very bittersweet moment for us because, on the one hand, we saw our idea and it was already built and they had done an incredible job, and it was clear they were just way ahead of us and it was too late.
But on the other hand, it was very validating. We had an idea for how the world should be. Some people we talked to were very skeptical about this idea, and so that validation was very encouraging. It was like okay, we were right. We were way too slow, but we were on to something.
So we kept brainstorming and then came around this idea of buying and selling time. It’s very easy to buy products online – on Amazon, eBay, a thousand other places. But if you ask someone “When was the last time you bought a service online?” Most people never have. And there are billions of dollars in services — from home improvement, house painters, dog walkers, roofers, to caterers and DJs, and none of these are online.
Often, you’ll walk around the city, and you’ll see flyers for a moving company thumbtacked to a bulletin board or a light pole. This seemed very antiquated to me and clearly not the future, and so we got excited about this idea and we knew I was leaving the White House in January of 2009, and so working toward creating the business so that I could jump off and join Thumbtack as a company.
My co-founder came out to the White House and he applied to be an intern at the White House one summer and we lived together. And so in our spare time, we talked about our idea, and then we just started going through all the steps that are necessary to create a business.
We created a business plan to help flesh out our thinking about what exactly we wanted to create, and we started thinking about the downside – the competitors, user acquisition, and lots of things we were idiots about, and we had no idea what we were talking about, and years later, we’d find out the true answers.
But, we’ve created enough momentum and we had enough excitement about it that my friend and co-founder graduated from school and started working on it full-time, and I joined him when I left the White House. And at that point, we only had some money from friends and family, and we went out and we raised a seed round from angel investors.
Q. How big was that round?
A. About half a million dollars.
Q. And you recently raised an institutional round for how much?
A. Four and a half million.
Q. And from serious, legitimate venture investors.
A. Yeah, not Mom and Dad. The first round was friends and family, and it was people who were investing in us as people because they believed in us, and this last round, they were investing in us as people as well, but they didn’t know us before and they believe in the idea, the traction, and what we’ve accomplished so far.
Q. You characterize Thumbtack as the Amazon of local services. Tell us how it works and who benefits when and where?
A. So, there are lots of places where you can find local services online right now, or find the names and numbers of people.
You can go to the Yellow Pages, which is just the Yellow Pages book that moved online, just names and professions and phone numbers. Or you can go to Yelp, which is basically like the Yellow Pages except they’ve added pictures and reviews. And there’s Angie’s List, which is very similar to Yelp, except it’s just for home improvement services.
The thing we thought was missing of all these was that all the work, the burden, was still on the consumer. So if you want to hire a handyman, you can go to the Yellow Pages and you can call a few dozen of them and most of them won’t answer the phone. Or most won’t be able to do your job. Most won’t return your phone call. And the same is true with Yelp or Angie’s List. You have to do all the work, and we didn’t think that made any sense.
At Thumbtack, you come and you tell us what you need. “I want a DJ for a party next weekend, and it’s got to be this type of music and it’s these hours, and he needs to bring his own equipment.” So instead of calling fifty people and finding out who can do it, what the rates are, Thumbtack reaches out on your behalf to fifty or a hundred different DJs, and we tell them what you’re looking for, and then if they can do it, they submit a bid.
So, instead of doing all this work, you just say what you need, and then a few hours later, you come back to Thumbtack and you have bids from 6 DJs. You can see their profiles. You can listen to their music and you can know how much they’re going to charge you.
And so, then, at that point, it makes sense for you to browse through them, decide who you want to work with and you can actually hire them. So, the goal of Thumbtack is to get you from the purchase interest to the purchase decision faster.
For right now, that means getting you quotes. One day, it might not even mean getting you quotes for some things like a locksmith. You don’t want to get quotes if you’re locked out of your house. I don’t want to wait five hours to see how much they charge. I want to open my phone and I want to say, “I’m right here in SoMA. Can Thumbtack send a locksmith?” And they’ll say, “Yeah, we’ll send a locksmith for a hundred bucks.” And I say, “Okay, send them now.” And that’s like a five-second transaction.
So, we’re not wedded to one single model. What we want to do is make it faster to buy local services, and we’ve started with what we call a “request for quote” model, but we think the future of services is probably many different types of models.
Q. So your approach is to move increasingly toward demand fulfillment and not just lead generation.
A. Yeah, there’s lots of lead generation businesses out there, and we ultimately want to be more than a lead generation business. We have a digital storefront where you can advertise your service and we send you new customers through that door. But ultimately, we want to be a back office behind that storefront. So we want to handle your payments and your invoicing, your scheduling, your CRM – all those things. At a high level, we want to abstract away all the business side for small businesses.
Like, an electrician or plumber, they have to be good at being an electrician or plumber. We can’t do that for them. But they shouldn’t have to be good at marketing and invoicing and payments and all these other things, but apparently, they have to be. And to be a good small business, you have to be an expert at a dozen different things. And so, we want to make it easier. We want to say, “Be good at your craft, and we’ll do everything else.”
Q. Tell me about your current role as co-founder and president of Thumbtack. What do you do day-to-day?
A. So, it has changed a lot when there was just a couple of us and we would do everything. As you grow bigger, your role changes and becomes more defined.
Today, my role is to lead all the operations. So, in the same way as our engineers build the electronic machine that runs the website, my role is to build the human machine. That means making sure we have the right people and they’re in the right places. That means training people to do new roles. It means if someone is not working in a certain position, helping them do a better job or moving them somewhere else. It means protecting and building our culture so that we all love working here and we’re all productive. It means creating processes — so how do we share information, how do we set goals, how do we have weekly meetings or quarterly meetings?
And so, coming up with all these processes, my goal is to create a human machine that is very productive and that we all enjoy working here and that no one else has to think about the machine. They can just do their work and be productive and create, and I just want to put in the processes that make that possible.
Q. It sounds like what Thumbtack is trying to do on a broader scale you’re trying to do within the company.
A. Yeah, definitely.
Q. How did you meet your co-founders?
A. One of my co-founders and I went to Yale together and played soccer together, and we have been friends for many years. And my other co-founder and I met during the social security debate. He actually came and joined me at the non-profit. He and I had a shared love of starting things, of creating this non-profit and we said, “We want to do this again.”
And so we stayed in touch, and I’m a little surprised actually we all ended up back together. It’s amazing. I feel very lucky, and so we had lots of intellectual shared interests and fortunately, we made it happen so that we could work together again.
Q. What do you find most exciting about your current role?
A. I think what I find most exciting is that we control our destiny in a very real way.
When we first started Thumbtack, that was the case to some extent, but we lacked lots of the tools. We didn’t have any money. We didn’t have any team members, and we really didn’t know what we were doing either. We were completely new to the startup world. We didn’t know how to acquire users. We didn’t know how to monetize.
But Thumbtack’s at a point now where we’ve figured out a fair number of things. We know how to acquire users. We know how to make money. We’ve raised money, so we have money in the bank, and we have a big team.
And so in many ways, the problems that have to be solved are problems that have to be just overcome by our own creativity. We can’t say we failed because we didn’t have enough money or we didn’t have the right connections. It’s totally up to us now.
There are a number of challenges we still have to overcome, but we have all the resources that are necessary. And so, if the problem can be overcome and solved, it’s on us. That’s very empowering. It means that you don’t have any excuses, but it’s also very satisfying if we do solve the problem because it’s all on us.
Q. What do you most wish you could change?
A. It’s a good question. That’s one of the things I like, is that if there’s something I don’t like, lots of it we can change.
One thing that you can’t really change is the speed. I sometimes wish things would go faster. I’m just very impatient because we have this very powerful vision for where we can be, and we’re very ambitious and we have lots of aspirations and we’re working our way there, but sometimes I wish we could just hit fast-forward and get there a little faster.
Q. What is the major bottleneck that, if you could remove it, would make you run faster?
A. Lots of it is learning. So, when we first started, the bottleneck was how do we get service providers to sign up? How do we get the handyman and the dog walker? And we literally had no idea, and we tried many different things until something really worked and now, we’ve signed up hundreds of thousands of service providers.
Then the next problem was how do we get consumers to come? And we really weren’t sure again, but we tried a number of things and made some big investments and we found a solution. And now, we have millions of consumers coming.
And so now, the next challenge we’re grappling with is how do we monetize at scale? How do we create a system that is fair for service providers and that scales across different channels?
And so, we think we have solutions, but it’s something that you can’t solve all at once. You have to try one thing and if it doesn’t work, you try another thing, and if it doesn’t work, then you try another thing and then eventually it works. And that learning is hard to expedite because you can’t try the second thing until you’ve tried the first thing because there’s information in the first test that informs the second test.
Q. Where do you ideally see yourself in the future, and how do you think what you’re doing today will help you toward that goal?
A. I’d love to continue working on Thumbtack for a while. I think it’s a very big opportunity, and it’s very easy to say the “Amazon of services,” but the Amazon of services is a $50 billion company, and if we truly could have that sort of opportunity, it would be very hard to walk away from, and it would be something that I could invest a decade in.
But I would love to do other startups. I think Thumbtack has been a great training ground to learn about how to start a company and I would love to do it again. I’ve made lots of good friends doing this, and I think, if we did it again, I might pay myself better at the beginning and I might not go through as much drudgery as we did in the beginning. But it’s been an amazing experience, so I’d love to do it again and again.
I’ve lost my interest in politics a little bit because, in the startup world, you just have so much more control over what you create and that is very intoxicating in a way that with politics, you have to be more tolerant of being a small part of a big machine, which can be satisfying and you can really effect change that way, but lots of your destiny is out of your control because the machine is just so big.
Q. What advice do you have for others who may be interested in exploring some of the career experiences you’ve had?
A. I think the most important thing is to be very scrappy, and even to be shameless about asking for help.
Whether it was at the non-profit or at the White House or even Thumbtack today, I have no hesitation asking a random person I don’t know for help. Or even for mentorship. When I was at the White House, I asked my boss, “How do I get your job one day? I think you have this amazing life path. I look up to you. Teach me how to do this.”
I did that many times throughout my career and people were very receptive. And you have to be open to the idea that you’ll be rejected or that people will just ignore you or just won’t help you sometimes, but it doesn’t matter. If you ask enough people, plenty of people are willing to help. Especially in Silicon Valley, people are very generous with their time, and if you just ask for help, you’ll get it. And that goes a long way, and most people just never ask.