0:05  
Hello, hello, you're listening to paradigm shift, a podcast about people building future and pivotal moments in their journey. I'm Ashish. And I'm joined by my co hosting. And today we're speaking with Sandra Daniels, who's the co founder of Thumbtack.

0:19  
So really excited to have Sandra with us today, Sandra co founded thumbtack in 2008. And help scale it to hundreds, maybe 1000s of employees now, and a 3.2 billion valuation, and recently transitioned out of day to day work after 13 years of the company, Sandra and I also had the chance to work together several years ago on growth in product at thumbtack, and I say the hyper growth stage of the company. So we'll definitely talk about that today as well. So Sandra, really excited to have you on a couple of things we think will be really fun to cover are like the early story of Thumbtack. I know like it was a really interesting founding story. And then it'd be great to get into the different phases of the company's growth over 13 years and how you've seen both the company evolves, and yourself and your your co founders. So maybe a good place to start is maybe you can just tell us a little bit about you and what CommTech does and how you guys got started building the marketplace.

1:08  
Great, Zane, Ashish happy to be here. So rewinding way back from an early age, I felt lucky about the opportunities I've been given, it was nothing super out of the ordinary, but I thought, okay, if I work hard and make some good decisions here, then I can make an impact, I can pay it forward a little bit. And so the first route that took for me was in college, in addition to studying engineering, so history, politics philosophy, followed that up and went to law school, I'd grown up outside of the DC area, I thought it was going to be in DC doing politics my whole career and married my high school sweetheart, we were both from that area didn't even crossed her mind that we would leave that area. While I was in law school, I kept in touch with a couple friends who'd gone a similar direction for similar motivations. They're working at the White House at the time. And we said, well, politics is one way to make a difference. But there's another way to make a difference, which is technology. So for a year, we had weekly phone calls, where we brainstormed ideas of things we could start successful create opportunity for people. And what we ultimately landed on was the idea for some tech, so happy to share a lot more about thumbtack, and what it has been what it is today, but at a very high level Thumbtack is the only app homeowners need to take care of their homes. So we help you maintain your home from beginning to end. We have regular maintenance schedules for our cars. But we don't have anything like that for our home. Our home is our biggest assets. Thumbtack is the platform that helps you maintain your home. Yeah, and so today, you know, 900 plus employees, we've raised more than $500 million. I think the latest valuation was $3.2 billion. So it's reached some scale today. And it's been quite a journey over the last 13 years with thankfully more highs than lows, but plenty of both in between. Yeah, what

3:07  
an incredible journey definitely want to talk a lot about Thumbtack. Before we get into that, what was the draw to politics? I know there's a lot of folks that come back from my time there that had like a bit of a political background, like where did that come from? Was it from growing up in the DC area? Something else?

3:21  
I'd say the founders, a lot of the early some tech team, we're all very human oriented, we care about making an impact in the real world. With normal people, I'm happy to tech products are built for the 1%. But what motivates me is building things that change the lives of everyone else. There. Lots of big, meaty problems out the world, I grew up with an awareness that I was one of the lucky ones in a big world of 6 billion people. And so what I wanted to do is, like I said, pass that forward, I feel like I have a responsibility to pay it forward. And so I still think today that there's really two big levers if you want to make an impact. One is technology. Two is politics. So the founders had very Jonathan and Marco both had very similar sensibilities and outlooks. They're impact driven, they're human oriented. And that's what kind of drew us all together. And you know, what, some tech it was not instill, I would say is not the sexiest tech problem in the entire world. It is a very human centric, people oriented, hops centric in many ways, business now, technology. We're one of the leading technology companies in the world, and we use technology to make our marketplace efficient to connect homeowners to service professionals to power service professionals businesses. But at the end of the day, you know, if you're wanting to work on the absolute latest cutting edge deep science research in the world, some tech, they're probably better place to go than Thumbtack. What has attracted people to thumbtack, in many cases, is the impact that we make on the lives of real people in the real world. So that is what is a common thread among all of us from the very beginning.

5:29  
So how did you guys meet? I think you went to school. But Jonathan, and you met Marco, maybe through him? What's the story there?

5:34  
Yeah, Jonathan, I played soccer together in undergrad club soccer team. And then Jonathan started a political advocacy organization in his junior year of college. It was for one of the geekiest topics you could ever imagined. And it was around social security reform back in 2003. In 2004, he started an advocacy organization for college students for social security reform, a geeky friend, Marco joined him in that venture, Jonathan actually left school for a little bit to work on it, I thought he was nuts, to put a pause on his school and graduate late because of it. But he did that. And both of them ended up getting really interesting roles at the White House out of that in becoming part of that whole conversation. So then, once that conversation wound down in DC, the organization did as well. Jonathan came back finished up school. And then the three of us got to know each other, primarily through that political advocacy organization that Jonathan built. And after that wound down, we got together and like I said, started brainstorming about new things. We were brainstorming, not just tech companies, we were considering political advocacy organizations, nonprofits, but what we eventually ended on was Thumbtack. People imagine these startup ideas as serendipitous moments. You're Jack Dorsey here in a park, in San Francisco, you slide down a slide, and you get the idea for a short messaging service, you go back to your office and code it up. That is great, if that happens to you. But for the 99% of the rest of us, that is not how it startup ideas happen. Many of the great ideas of our time have been very deliberate the result of structured conversations and structured thinking over the course of months in years testing and learning into a business or product. And that was definitely the case for us at Thumbtack.

7:49  
That's great. Would you mind expanding on that? Because I think that's absolutely true. It's really hard to come up with good ideas. Clearly something you did worked. So what do you think contributed to going through that process and ending up with a good outcome?

8:01  
Well, I used to think that all the good ideas were taken, that was impossible to build a good idea in the world, I used to believe in the efficient market hypothesis, there was $100 bill on the sidewalk waiting to be picked up, it's not even worth bending over to pick it up, somebody else has already picked it up, my view on these things has completely changed. There's so much opportunity out there so many problems, tackle and relatively few great business builders, operators going out to build them. And so whereas previously, I'd thought so much of entrepreneurship and creativity and building new things in the world, it's about serendipitous moments, brilliant genius ideas. Now, I think of innovation as much more of a deliberate process where you basically start building something in a big market, and you just hang a shingle, and you put your idea out there, and you put it into the market, you get a few early customers, you hear from them, you iterate, you go deep on the things that are working for customers, you avoid the things that are not working for your customers. And you just build building blocks, one on top of another. And I think oftentimes people are scared away from entrepreneurship by this idea that they think they have to have brilliance, or a new insight. But in fact, many of the great companies of our time are just one additional rev on top of something that's previously been built, that has been executed extremely well.

9:41  
So going back to those calls. How did you guys structure those and what were some ideas you ruled out? You remember? I mean, I can never remember all the ideas I've rolled out and if you don't, but I wonder if there's any that come to mind?

9:53  
Oh my gosh, there were so many. I mean, I remember some of the names at least that we ruled out from tack time strapped was our original name. The whole thing was kind of born of economic wonkiness, we thought there was a lot of inefficiency in the labor marketplace connecting consumers with Service Pros. We thought the ways that people were connecting were really old school was Yellow Pages being delivered to people's doorsteps, people stapling and moving company flyer to a telephone pole or thumb tacking their yoga business card to a bulletin board. We said, that's not how this could be done in the future, we thought, it's going to be improved. We're going to help people save time. Let's call it time strapped, we thankfully ditched that super early for what turned out to be a much better name, thumbtack there was a personal finance software, we said, hey, all of our financial accounts are spread across these different sources, our bank account, our college loans, are mortgages. Wouldn't it be great if we had a piece of software that connected them all, centralize them all in a dashboard. And then we could make money perhaps by offering better rates on these different products. We had the business plan together. And then literally like the next week, mint.com launched, and they soon after one TechCrunch 50, which back in the day was kind of the royalty tournament in startups. And we said, well shoot somebody else who really executed on that idea, much better than we did. But on the other hand, at least we're on the right track. So in retrospect, even though it felt terrible at the time, we're happy that that happened, because it turns out thumbtack was a much bigger product than that one turned out to be.

11:54  
So you guys came up with the thumbtack idea? How did you get your first few customers? How did Jesus ever like put it out there and build confidence in the idea?

12:02  
Well, we looked at the other great marketplaces at that time, Craigslist, eBay, Amazon, and we said, okay, they have a couple things in common. One, they have all the liquidity in the world, all the supply all the demand to their products, UI is look pretty ugly. So the lesson we took from that is that at least at the beginning of the company's life, we are going to focus above all else on building the Quiddity in the marketplace. So the first whole stage of the company's life it was, you know, half a dozen of us. Many of us were living in a townhouse above the Castro, which is a neighborhood in San Francisco together, we focused on nothing except how do you sign up hundreds of 1000s of small businesses at scale for little or no cost? We tested all kinds of different channels. What we eventually landed on was primarily email marketing. So we sent a bunch of emails to plumbers, carpenters, and dog trainers, we said, hey, here's a new platform you can use to find business, check it out, sign up, we'll start sending you business. So we got excellent at that world class at that. And we solve the supply problem. Then, for the next 18 months or so we shifted our focus exclusively to solving the demand problem. How do you sign up millions of consumers at scale for zero cost. And what we hit on there was SEO. So we were kind of wandering in the wilderness for a long time, we didn't know how we were going to generate demand. And one day, one of the founders was at a bar below our townhouse, and randomly sat down next to someone that he struck conversation with founder was telling them about Thumbtack. And the guy he sat next to set, let's take a look at some Google search results, like house cleaner, San Francisco or mover, Atlanta. And my founder said, Okay, I don't know why. But sure. Let's look at that. And the guy said, Have I think you all have a big opportunity in SEO? And my founder said, What's SEO and CIO turns out this person, one of the world's experts in SEO, search engine optimization, Art Science, getting your website's listings to the top of Google search results. And this person became one of our first angel investors and basically architected our whole SEO strategy with us. So for the next two years or so we became world experts in SEO. Again, I had never heard of SEO before we started thumbtack, and then I became a world expert in it during that period. So that is really what powered the consumer side of our marketplace. And one thing I will say that you might have heard in both those stories, building the supply side and building demand side is you know, for these growth startups, almost always it is not If a variety of different marketing channels that you use to build users, instead, it's one single marketing channel that works for your company. And you just mind it as deeply as possible. If you've struck oil, keep digging deep. So

15:21  
first channel was Craigslist. Am I remembering that correct? And then and then SEO was sort of like the big breakthrough a second channel,

15:27  
Craigslist for the supply side. So it was Craigslist before email marketing? Yes. So there was a period, you know, back in 2008, to 2012 13. It was kind of like a golden era for these marketplaces coming online. He was a lot of us working together the Uber guys a Lyft. Folks before they were called Zimride, Airbnb, we knew of all of each other, at least, if not personally, then through kind of the tight knit marketplace, circles. We were all going after similar channels. So yes, that was during the period when Craigslist just being kind of verticalized or disaggregated. And a lot of us were kind of picking off pieces of the Craigslist verticals. And so yeah, a lot of us were using Craigslist to bootstrap among channels.

16:11  
So one of the question about the early days in your personal story, so you were at law school, right? You went to Yale Law School, which is probably the top law school in the country. And contract was at this really early stage. And I think the demand wasn't quite solved yet. There was a bit of a bumpy road in the beginning, but you made the decision to to give up your law career and jump into some tech full time that tell us about that. What led you to that decision?

16:36  
Well, figuring out how to take the leap from a quote unquote, normal job to a job that your parents will think you're crazy to take. It's not even a job at all. It's a startup that will almost certainly fail. It's a huge reason that I think more startups are not formed. Because there's huge barriers to entry. People think it's a big risk, and it is for many people. And more importantly, people don't know how to like fund it or finance it. A lot of people have school loans that they have to pay back. They need to have steady income at thumbtack we went for, I think it was two and a half, three years earning. It was like $20,000 a year or something. It was just again, the team lived together in a townhouse The company paid for the townhouse. And there was just like basic living expenses on top of that. So the other founders went out to San Francisco from day one. I couldn't do that. Because I was married, I had a kid on the way I needed to earn an income. And so what I did is, I said, Okay, what is the number one highest paying job I can get out of law school to I can take an earn and save up enough money to then go for 1824 months without an income. So for me, that was a law firm job. I went in, I started in November of 2009. The day I started, I put a note on my refrigerator that said you will leave this law firm on January 31 2011, which was the amount of time that calculator would need to stay there in order to save up enough money to go without income for a couple years. And I did that I worked at the law firm during the day I worked at thumbtack as the first customer service rep at nights on the weekends in helping build our CS infrastructure. And then I left the last week of January 2011 happened to be the same week my kid was born, we had a six month transition period work to work remotely. And then we moved out to San Francisco. So you know, for me, the bigger risk was actually not taking the leap and joining thumbtack, I knew I would always look back on myself if I didn't take that leap. And think, man, what if I knew I could always go back and earn an income if I needed to. I told my wife, we will be back in DC in 12 or 18 months if and when some tech fails, don't worry about it. Some tech kept not failing. So here we are still in San Francisco, you know, a decade plus later. But that's how I made the transition. My advice to folks who are looking to make a similar transition is take the leap, take the risk, it's not as risky as you think. It's definitely not as risky as your parents think. Just be as creative as you possibly can to figure out how you're going to fund it, because that's really your only barrier to taking the leap.

19:36  
That's great advice. So you moved to San Francisco, you built up the supply side, then you built up the demand side. And it sounds like at that point, you basically had product market fit like you were ready to scale this up. Could you describe that scaling phase of the company and what that looked like in terms of user metrics and challenges we were facing?

19:55  
Yeah, So stage one of the company was building up supply stage two was mostly about building up demand. But before we get to stage three, scaling, let me finish out stage two. So there was a period when we had built the supply side of the marketplace, we built the demand side of the marketplace, things were going great. We thought we had found product market fit. This was during the period when Facebook, Twitter, Pinterest were all out raising tons of money based on user growth exclusively no revenue. We thought we were hot stuff, we went out to raise our Series A round. And to make a little bit of a long story short, we ended up talking to 4045 VC firms, they all said, No, we were running out of money. We were getting towards the holidays, we had a team of 100. Plus, in the Philippines at the time, we were writing layoff plans for them. We were writing layoff plans for ourselves. And then to the eternal credit, Chad Katz, Chaplin saw a good thing, and made a huge bet. And we raised our Series A. So even though it turned out great with a great partner, we were traumatized. And we said never again are we going to put ourselves in a position where we have to raise money in order to succeed. So we finished out stage two of the company's life by focusing on nothing but a revenue model. So we iterated through a handful of revenue models through a commission based revenue model, a subscription based revenue model, but what we eventually found was a form of what we call a pay per lead revenue model. That worked extremely well. So we went out to raise a series B round, about nine months, or a year after that, and Sequoia invested. So here we were, we had gone three, four or five years wandering in the wilderness, nobody paying attention to us, 610 of us living together in a townhouse. And suddenly we raised from Sequoia, so whereas previously would raise three, four $5 million, then in the next 18 months, we raised about $150 million from Sequoia Tiger global capital G in quick succession. So that launched us into stage three, Scaling. Scaling was, on the one hand, really exciting, because it's fast growth, people were paying attention. On the other hand, it was frustrating. And I'll explain why in a minute. To us scaling meant building out the infrastructure, it was like migrating from static servers and Dallas to AWS, moving from a monolithic code base, built in PHP to a more service oriented architecture and various coding languages, building out our design systems and foundation, our brand refresh our people, culture, foundation, recruiting. So you know, during this period, we were scaling from five to 100, software engineers. And it was exciting, like I said, But you know, for nine months, I had five or six values fit interviews a day for software engineers, there were entire quarters where we shipped nothing to production, because we were building out our infrastructure. So that is why pieces of it were frustrating.

23:03  
So definitely want to talk more about that. But just going back to the fundraise story for a minute, you had 42 ejections, which sounds super traumatizing, you finally had an investor willing to take a chance on you. What was the primary reason that you got passed on so much? Was it like a revenue gap? Or like an unproven pay per lead revenue model? Do you remember what the primary sort of like feedback was? And the concern was,

23:28  
I think we had two strikes against us. One was no revenue. Two was unknown, unproven founders, so none of us had a track record. We had no reputation. This is the first thing any of us had built. So people were willing to take a flyer on proven folks with no revenue, even if they had user growth, people were willing to take a flyer on companies with revenue growth, even if they had founders without experience, but we were both and interestingly, not only were we inexperienced founders, none of us are technical founders. So that kind of hung over our heads. For many years. When we went to talk to VCs, they said, Oh, you don't have like, you know, software engineer on your on your founding team. So that was an additional kind of, like, cultural strike against us, I would say. So it was those things kind of combined that I think made people hesitate to invest in us in the early days.

24:22  
And in what do you think God Jed over the line eventually was it had you guys like figured out a way to like, prove a little bit of revenue, traction, oh, by then had not

24:30  
proved revenue traction. I think he just saw that the market we were going after was absolutely gigantic. Local Services is one of the last remaining areas of the economy that has yet to come online in a significant way. You look at hotels, taxis and transportation, dating ecommerce. Even back then these were like 40 5060 plus percent internet penetrated local services, still less than 10%. Internet penetrated is transacted overwhelming through word of mouth. So you're asking neighbors or parents at your kids school or friends who just got married for introduction to these different service professionals. And he thought, gosh, if these guys can do even 10% of what they're saying they can do this will be a winner,

25:14  
right? And then the model clicked, and you were off to the races, and you had incredible growth and that dog Sequoia to invest. Do you remember what that was like? And whether landing atop we see changed the perception and ability to recruit and, and stuff like that? Was it an unlock in any ways? Or? Or is it really like not that big a deal?

25:33  
Yeah. So I would say, perhaps the biggest mistake we made or misperception we had in the early days was the power of story and narrative. All of us are just so execution oriented. We only focus on real results, rather than kind of like vanity metrics. That served us extremely well, because there were so many other marketplaces for local services. Back in the day, there was, you know, people were telling us, oh, you need to become like, you need to build Uber for house cleaning, or Uber for whatever, oh, you need to like build another version of Groupon. We stayed so focused on what we knew our customers cared about most. These other ideas and products were sideshows. So over the long term, been extremely focused, execution oriented, only caring about real results and real growth in the real world that served us well. However, it made us kind of ignore the power of story and narrative, we did not really engage with PR and media, much in the early days, other competitors did, and that served them very well. Similarly, kind of had a chip on our shoulder about the brands of VC firms, and the power that that would bring. And, you know, over the course of time, I've learned at least I personally was wrong on those things. When school invested, it legitimated us in the eyes of future potential investors. It kind of erased this narrative around first time unproven founders. And it made potential hires, it kind of like, introduced a whole new level of potential hires, who took some tech seriously as a place to work. And I think we landed a bunch of amazing folks who ended up working at top tech and significant part of because of kind of like the Sequoia name that had invested in us.

27:36  
And the growth was there too, right. I know, when I joined, I think the having sort of like that good backers mattered. But also like, the team was great. The company has grown really fast.

27:46  
Oh, with all the say, without the goods, it doesn't matter. Yeah, who invest in you or what the names are, or what the vanity metrics are. You can't build a team and you can't build a great company. So we had the goods. Yeah,

28:00  
that was an enormous amount of money, right, in the context of a history of what you had raised before then. So what was the goal of those rounds of funding? And what was the money intended to be used for?

28:10  
Yeah, previously would raised eight $9 million Koya. Net round, I think we raised something around $12 million dollars. And it was like 30, and 100 million within 18 months. So like I said, what we kind of spent our time doing was building the infrastructure. And a big part of that was, I'll never forget, our Series C investor came to us founders, and he said, kind of congratulations. Now it's time to grow up. And for us, that meant a couple things. One was building out an exec team. So for the next 1824 months, we spent a lot of our time hiring, VP design VPN, VP, ops, VP people on and on. And then the second thing that meant for us was hiring executive coaches. So we did that. We hired a team of two coaches. And going through that process during our infrastructure. Stage three was one of the most powerful processes I've ever been through. coaches come in all different flavors. And we've worked with many different coaches over the course of time. But these first couple, they were very analytic. They had a survey, they had developed in house 125 questions and asked all about how you work. They said, Okay, give us the names of 810 12 people in the world who are closest to you, both personally and professionally, we're gonna administer the survey to them, gave them the names, they administer the survey. And I'll never forget, they pulled me into a room after they got the survey results. And if I was ever previously under any illusions about what I was good and not good at before, then well, they were entirely shattered. during that session. Each of the founders went through that process. And it was an extremely powerful process, because for the first time really, I think we could admit to each other that none of us was perfect. We all had our strengths. We all had our weaknesses. The best we could do is identify and celebrate our strengths, talk openly about and support one another and compensating for or improving on our weaknesses. And it could structure to our founder relationship that allowed us to work through kind of any crap that came up in the day to day. You know, one of the things that blows up startups is founders getting pissed off at each other. Here we are 13 years later. And the founders were on a whatsapp thread where we communicate almost every day still, about stuff, the business stuff in our personal lives stuff in the industry. And I think one reason for that is because we're all very long term focused, we knew the idea we're going after is generational in nature, we want to build an iconic tech firm that was stood the test of time. And so this was the work at least of decades, if not a lifetime. And when you're operating on that timeline, you know, the things you can get pissed off at each other about in the day to day or the week to week, or even the year to year kind of wash away. But the other reason, I think we've stuck together as insignificant part because of that exercise, that structured exercise we went through where we could like, have structured conversations about the disagreements, and be more vulnerable and open with each other. That's huge.

31:24  
And thanks for sharing that. I think this is an issue on a lot of people's minds, like, especially at the early stages, we can be really tough. So, you know, what advice would you have to early stage founders who are struggling to resolve differences? And what are the some of the things that you all incorporated that you think have led to the relationship lasting and being so healthy?

31:45  
To me two things really helped. One is just when I said coaching, so I always advise founders to get coaches. And it's not just for you personally, but it's really for the founders to start and then expanding, it's the whole leadership team. Ideally, you find a coach who can do kind of like a strengths and weaknesses assessment of each of the leaders of the company individually, and then like help you all think through together about where the gaps are, how to fill them, how to like slot people into the right roles, you know, one result of this conversation for us was like, Oh, I personally had a lot more structure afterwards to think about what my right role was at the company. And you know, what the other two founders are best at where they draw their energy from. And we all got much more comfortable with the roles that we were in after that, I think that's one thing you know, where founders can oftentimes I think get annoyed with each other is when each of them thinks they can do it all. And they can do each other's jobs. And so the most healthy thing I think you could do is do a real assessment around who's good at what, and dividing responsibilities accordingly. The second thing I would say is put on blinders as much as possible to the outside world. One advantage I think we had way back in the day was the tech world was totally different. You know, we started some tech, nobody was going into tech. Nobody I knew was moving from the East Coast to San Francisco. tech CEOs were not on the cover of magazines. Tech was not part of the cultural zeitgeist like it is today. Nobody was talking about it today. It's kind of like the center of the cultural zeitgeist. And so it's really easy to get distracted, really easy to look at people raising big rounds, really easy to kind of like, feel bad about your own progress when you see the headlines. And so as much as possible, like put on blinds, we used to keep a spreadsheet. In the early days, where each row was a competitor, we used to monitor TechCrunch funding announcements really closely. But then after 18 or 24 months, what we found was this is just a total distraction that companies that we thought were hot stuff, have fizzled out companies that we had never heard of, in a different part of the world are kind of the winners coming out of nowhere. And so the best thing we can do is just focus on what we can control, which is ourselves and how we execute internally and the decisions we're making. So that would be my other piece of advice. Just ignore what's going on outside in the world. Focus on what you can control.

34:19  
That's a great reminder, especially right now when it's like we're in this like really hot market. So one of my observations, Sandra has been how your role has evolved continuously as the company has faced new challenges and been in different phases of its growth. How have you thought about where to have the most impact? We'd love to hear about how you approach that. Yeah, so

34:39  
I built many things at Thumbtack. Over the course of time, I helped build our early operations teams Philippines, and then built and led a lot of our growth marketing in SEO SEM. In particular. Then I moved on helped build a lot of the foundation of our people culture values, V one of people analytics One of our formalized DEI efforts, and I led a recruiting team for a couple years, and I didn't expect recruiting. So really, what I did was identify my strengths, what brought me energy, what my zone of genius was. And for me, that's, I'm a builder. I'm an operator, I love taking things 01 I love building systems, processes, operations, technology to make things more efficient. And so I took on important strategic initiatives at the company that could use a leader who had those strengths in them. And then once I got them to some scale, after 1218 24 months, I handed him off to a pro. So that is what I did over the course of time. And it worked out really well. It kept me energized about being at the company, for 13 years, it was awesome for the company, to have somebody with those skills to go and point at new initiatives and build things. So it was really just a matter of like, having a great conversation over the course of time with the other founders about like, alright, sander, what do you like doing? What are you good at? And what does the company need? Right now let's like find the center of that Venn diagram in point you're at it. And it sounds

36:15  
like that was the the rest of the of the secret to keeping your the company for 13 years to it's very, it's I think it's relatively uncommon for co founders to work together that long. And it sounds like that was key to you staying focused and excited to be on the journey for over a decade.

36:31  
Exactly. You know, I'm like a creative, curious person, all of us are and got to mix things up every two, three years. And so I would have gotten had I just been pigeon holed in a single role or a single function or whatever. For a long time, I think I would have gotten, you know, burned out long ago. But learning new skills, taking on totally different responsibilities, departments kept things interesting. Tell us a little

36:55  
bit about building a great culture that allows people to sort of like realize their potential to do their best work. How did you approach that at Thumbtack? Well,

37:04  
for better or worse, company's culture is derivative of basically its founders personalities. And so like I mentioned before, US founders I would say, are very human centric, we were down to earth, pragmatic, mostly self aware, and pathetic. And so a lot of our culture flows from that, you know, we have cared a lot about building a culture, where people feel at home where they can bring their full selves to work, where they can, where they have a high sense of inclusion and belongingness, but can also learn a lot about themselves. We personally have always been curious about, okay, what are we good, not good at? And how can we get better. And so we had a culture from the very, very early days, that was really focused on being the best versions of ourselves, and being open about the things that we're good at, and celebrating those things that we're not good at, and talking openly about those and building deliberate processes to improve the things that aren't working. I mean, literally, like, you know, we started doing 360 reviews of each other in the first six months of the company's life when we were like, you know, 23 or 24 years old or whatever, not because we had heard that it's something we should do. But it's because we were already doing that in our personal lives. And we were excited to get feedback about stuff we weren't good at, from our friends, and these people we were working with, and then we would get that feedback, and we would build it into action plans. So okay, here is a one pager on what I heard, are my strengths where I heard my weaknesses. Here are the one max two action items I'm going to work on over the next six months to try to address my weaknesses. Here are the names of three friends at the company who are going to be my stakeholders, I'm going to meet with monthly to check in and be my accountability partner on whether I'm actually doing this and reminding me that I should be doing it. And then I'll see what progress I make in six months. And it's that kind of growth mindsets, fearlessness, about our ability to get better and improve, I think has long permeated our culture.

39:42  
That's amazing. Love that. So reflecting back on the hyper growth phase, it's a challenging time for most companies and frustrating to as you mentioned, what are some things you think contacted really well through that phase? And what are some things you wish you'd maybe done differently?

39:57  
We were excellent at going slow in the right way. So I think we're excellent at going slow, which is both our greatest win, and our greatest weakness during that period. So we really set the foundation in the right way we built the right infrastructure. For, you know, the next decade, during that period, we put all the right systems process technology in place. So that was smart. We've always been really smart about it deliberate about sequencing the core, one thing that needs to happen next, for the company to make it to the next stage, at that period, it was infrastructure. The flip side, you know, our greatest strengths are always our greatest weaknesses. So that was our greatest strength was also our greatest weakness, you ask, What would I have done differently? Well, I probably would have split out during that period, a piece of the company to really experiment much more aggressively on product revenue model, we got to the end of that infrastructure period after three, four years, and the business was growing, and it was doing great. But we had kind of punted on some existential questions about Kay, How scalable is this product in this business model. And we thought to really make this product and business models scalable, to bring it to make it truly delightful to make it the one app that homeowners go to, to care for their homes to drive, repeat. and word of mouth use, like our current product and business model is probably not it. So I think we waited a little too long probably to really address that head on internally. So that's why I would have done differently, had had a little bit of at least a piece of the company that was experimenting much more aggressively on new products and business models.

41:42  
So Senator, you recently transitioned out of the company, we'd love to hear what led to that decision and what you're up to these days.

41:49  
So what motivates me today is what's always motivated me, which is making a real impact in the world, unlocking economic opportunity for folks, I think the greatest impact I can have is creating jobs for folks. And so in addition to that mission, and core motivation, I thought a lot about alright, you know, thumbtack was my first decade plus, where can my next decade plus be? I went through a whole exercise in 2020, around thinking about what am I good at what to draw energy from, I used to book design your life, that I recommend to everybody who's potentially go into a transition period that kind of walks you through some very specific exercises, to try to draw these things out of yourself in a structured way. And what I basically said is, is I love building an operating, so I'm gonna start want to continue starting new things. So I started a couple new things. In the meantime, one is recruiting technology company, it's called scaled. If you need help, recruiting, let me know, and you may be able to help. But what motivates me there is that the recruiting industry is huge. There was nothing more important that I did at thumbtack and hire people. It's the founders number one job for a decade plus, and a lot of the recruiting market feels kind of old school inefficient. And so I thought, okay, I can maybe go out there and bring some innovation to the recruiting industry. So starting with that, and then kind of as a another fun project with my best friend from high school, started a mobile dog grooming business in the Bay Area. And it is fun, and it's fun project on the side. But I really think that one of the most important issues facing the United States over the coming decades is the gap between what the modern economy needs and the skills of the labor force. And even though it sounds a little bit silly, we in this particular vertical have found a great way to take kind of like people who aren't trained for a high income earning skill and can make maybe 30 $40,000 a year, and within eight weeks, turn them into somebody who can make $100,000 a year plus grooming dogs. And so I think there's a huge opportunity in this particular vertical. But I think there remains a huge opportunity across all the skilled trades, to train people up, create a trade school for a modern trade school for the skilled trades. So this is the type of thing that motivates me and gets me going. That's great.

44:33  
So Sandra, we have three questions that we ask every guest on the show, and the first is around superpowers. You shared a lot about what you enjoy working on. And so maybe it's a perfect venue to expand upon that. The superpowers are things that feel like play to you but work to others, something that you're really good at. Other things that you've identified yourself that as superpowers and things you like to lean on.

44:57  
And it's a few different types of business builders. Like visionaries and communicators, on the one hand, you know, others are our product, lead builders, I think there's a third type of builder that is under discussed, which is like an operations systems, Team efficiency builder, where you're kind of like, just maybe like a CEO type, where you might not be the greatest visionary in the world, you might not be the greatest product visionary in the world. But holy cow, like give yourself a market and put a stake in the ground. And you can just execute day after day reliably and build a great foundation that ultimately generates huge innovation. And that I think, is my superpower, that latter type of business builder. And that's what I spend my time focusing on.

45:51  
The second question is around turning points, are there people over the course of your career that have given you breaks that you're grateful for

45:57  
so many, the first people that come to mind are my parents, very lucky to have been born to great loving, stable parents, who supported me kind of the entire way, they certainly did not spoil me. But they kind of exposed me to the world. Beyond where I grew up. My mother worked in international development her entire career. So when I was a little kid, I was traveling to Zambia and Zimbabwe and Ghana and India and seen firsthand kind of how unusual the place I was in where I was growing up. And then relatedly, I think they showed me that there's kind of like a world of ambition and opportunity out there that exists kind of like beyond your place, your home where you grew up. And, you know, you can take whatever path in life you choose. But if you so choose, you can go after that. And so they let me dream big. So that I would say is kind of like the core of it all.

47:02  
That's huge. The third questions around books you mentioned, design, your life was impactful for you other other books that have had an outsized impact on the way you think about your work in life, different books

47:13  
resonate at different moments. Design your life was an important one. However, honestly, the books that I spend most time with are our fiction. And I think fiction gets a bad rap. in tech. Again, building businesses is a human endeavor, both working with and building a team, you have to be empathetic, relate to people understand the shoes that they're walking, and be able to put yourself in the shoes of others. And then it's also knowing about your users and your customers and being able to put yourself in their shoes. So there's all kinds of books of fiction that are really character profiles. So the life a little life that was published a few years ago is one of the most amazing character profiles I've ever read. But fiction generally.

48:02  
That's fantastic. Sandra, this has been a great conversation, and we've learned a lot, and thanks for coming on. Thanks for having me.