Venture Unplugged: Leah Busque Solivan Founding And Selling TaskRabbit

Leah Busque Solivan is the founder of TaskRabbit and a Partner at Fuel Capital. TaskRabbit is an on-demand services company that can help you with everything from building Ikea furniture to standing in line for you at the Apple store. In this conversation, Mayra Ceja and Leah Busque Solivan discuss

  • Her humble beginnings as the first Tasker on TaskRabbit and eventually sold it to Ikea

  • Her personal challenges with founder stress and how it put in the hospital right before her last fundraise

  • How she’s helping entrepreneurs as a venture capital investor.

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Mayra Ceja
Hi Leah, thank you so much for coming on Venture Unplugged.

Leah Busque
Thanks for having me.

Mayra Ceja
And now you're somebody I always wanted to interview because I think you can share a lot about what it's like to go from the founder journey to the VC journey. And I think being on both sides of the table, you really have a lot of insights you can share with our audience. But before we get started, why don't I provide a little bit of background for our audience, and you can fill in any gaps that I might have.

Leah Busque
Great.

Mayra Ceja
And then we'll jump into questions. So you're the founder of TaskRabbit an on demand platform service where you can hire people to do almost anything from furniture to standing in line for you at the Apple store. TaskRabbit raised $50 million from top Venture Capitalists such as Floodgate, Shasta Ventures, and LightSpeed. And it was eventually acquired by IKEA in 2017, and most recently you joined as a partner at Fuel Capital, right?

Leah Busque
That's correct, yeah.

Mayra Ceja
Did I miss anything?

Leah Busque
Yes. Lots in between. Lots of details in between.

Mayra Ceja
Okay, perfect. So we'll go over them in our detailed questions.

Leah Busque
Okay, good.

Mayra Ceja
So before we get started, one of the things that I'd like to learn from my guest is taking them back a little bit towards childhood. As a child, did you ever dream of building any company?

Leah Busque
Not really. I mean, I grew up in a very tiny town in Shirley, Massachusetts. Population was 4,000. Kids went to school in one school building, kindergarten through eighth grade, super tiny. My mom was a stay at home mom. My dad was in the air force for over 30 years and so I wasn't really exposed to entrepreneurship as a child.

Leah Busque
Now, having said all that, I do remember distinctly this memory I have when I was probably about eight years old, asking my father what the highest title in a company was, and he told me it was being a CEO, a chief executive officer, and I remember starting my first company that was called Pollution Solutions, which was a recycling company for my elementary school. And I set up offices in our basement and all my cousins and my sister had jobs, and I was very organized and I ran it like a company.

Leah Busque
And so I think there was something innate in me from a very early age, where I had ideas and I had a vision and I wanted to execute them, and so that was my first CEO job.

Mayra Ceja
It sounds like you were very ambitious from the start. And so I guess that brings us to, flash forwarding a little bit to that first year when you decided to launch TaskRabbit. Walk us through that story.

Leah Busque
Yeah, so I was a Math Computer Science major in college and then I started at a small startup that was acquired by Lotus and acquired by IBM. So I ended up at IBM as a software engineer, and I was working their programming mostly in C++. And I was there for about eight years and I had this idea for TaskRabbit while I was at IBM. And I remember it was February of 2008 it was cold and snowing outside. I was living in Boston at the time, and I was getting ready to go out to dinner and meet some friends for dinner when I realized I was out of dog food.

Leah Busque
And I thought there's got to be an easy way to get this dog food. This is such a simple problem, why isn't there a simple solution? Well, the iPhone had just come out, four months earlier. So it was a brand new device that people had started carrying around 24/7. There was no App store. Facebook was still mostly in college, but kind of breaking out into more mainstream. But as an engineer and as a technologist, I got really excited about mashing up new emerging technologies around social networking, location based services, and mobile technology.

Leah Busque
And so when I was out of dog food that night, I thought there's got to be someone at the store this very second. I should be able to use this new device to connect with them. And that was really the genesis of the idea. I ended up quitting my job at IBM four months later, built the first version of the site, got it launched in Boston, and it kind of snowballed from there.

Mayra Ceja
Walk us through that first year. What was that like? How quickly did you grow? What were the main challenges there?

Leah Busque
Well, the first year was really hard because I left IBM in June of 2008, by September of 2008 we hit a really tough economic downturn. The stock market had crashed, people were being laid off left and right. I had just left this cushy job at IBM and I was thinking, what did I just do? What am I doing? But it turned out to be the best time to start a company like TaskRabbit because it really enabled a new workforce and a new way of people to make money and a new way of working.

Leah Busque
And so that first year was really, really hard because it was difficult to raise money. In fact, it took me about nine months to get $150,000 raised, from two angel investors in the Boston area. I recruited the first 30 TaskRabbits to start the site, but I really was the original TaskRabbit and I had this little Vespa scooter I'd ride around Boston-

Mayra Ceja
That's amazing.

Leah Busque
Doing jobs for people.

Mayra Ceja
I love that.

Leah Busque
Yeah. So really was very bootstrapped, maxing out credit cards, running around like a crazy person, but just really understanding how people wanted to utilize the service and then also on the other side of the marketplace what the taskers needed to become successful. So I look back on that time and because I was so hands on and because I was the TaskRabbit, I really understood how to build the service and the company.

Mayra Ceja
As the company grew what do you think was a key decision that you made early on that really set you up for success?

Leah Busque
Well, a lot of decisions that I made early on, I think I look back, they turned out to be serendipitously, miraculous decisions. They led to bigger things that I could never have planned on my own. One of those decisions was how I decided to go out to the West coast. I was 28 years old. I had never set foot on the West coast in my life. I was an East coast girl.

Leah Busque
And so I heard about an incubator program that Facebook was running in the summer of 2009 called FB Font. And I heard about it from the CEO of Zipcar, Scott Griffith, who kind of had taken me under his wing. He was letting me work out of the Zipcar office for free in the Boston area for that year. And I applied to this incubator program and got in and I thought, "How am I really going to go to the West coast and do this startup bootcamp?".

Leah Busque
And it was a big decision, but I decided to do it. And it turned out we were one of 25 companies invited to attend. Most of the other companies were already local to the bay area, so we were one of the few that were traveling back and forth across the country. But it was an incredible experience. It's really what got me connected to some amazing advisors, and then eventually investors who helped me get a seed round of funding done for TaskRabbit

Mayra Ceja
Marketplaces are really hard. How did you hack the whole chicken and egg problem?

Leah Busque
Well, it's definitely a chicken and the egg problem, but with TaskRabbit I very quickly figured out, and if you don't have taskers on the platform, there's no one there to do the jobs, and so you really do have to see the platform with one side of the marketplace first. And that was the tasker community. Once I got the tasker community set up, I really had to set expectations with those founding TaskRabbits to say, "Listen, you're not going to see hundreds of jobs immediately. It's going to be a slow build, particularly in a new market." And so setting expectations, because if the TaskRabbits didn't get enough work, they would cycle out and become disengaged.

Leah Busque
So it was a constant balancing between the two sides of the marketplace, but it always started with the tasker community, and I think that was a real insight that we had as a company, was to focus on the taskers, focus on enabling them to be successful because we knew if they were successful then we could add more business onto the platform.

Mayra Ceja
A lot of founders in these marketplaces have a lot of data on their customers. You happen to have very unique data. You're actually getting to know what people are asking other people to do. What are some interesting stories that you learned from your customers?

Leah Busque
Well, early on we weren't sure what people would want to use the site for and the service for, and so I really wasn't sure, would it be dry cleaning pickups, grocery deliveries, IKEA furniture assembly. It turned out once we get enough data, we could start to see pockets of interesting categories. The number one revenue driving category was IKEA furniture assembly for such a long time, like from the very beginning, so actually in the end when IKEA acquired us, it wasn't that much of a surprise as I look back.

Leah Busque
But there was this long tail of jobs that always occurred on the site and we had to get really good about grouping them and theming them so people would know what to use us for. Because when you tell someone you can get anything done on TaskRabbit, their mind goes blank. They have no idea what to use you for. And so we had to think about focusing in on home services and what are the categories in home services that would become really popular.

Mayra Ceja
Looking back in the history of TaskRabbit and you being there, what do you think was the inflection point where you knew this was working? Yeah, I mean I think I have this whole philosophy around winning versus success, where I define winning as points on the board, revenue, milestones and success incorporates winning. It includes revenue in milestones and metrics, but success also includes values and purpose and impact.

Mayra Ceja
And I think from a very early stage at TaskRabbit, I knew that we were going to be successful. I didn't always know that we were going to win in the space or completely dominate the industry, but I knew based on the interactions that were happening on the site that we would be a success.

Mayra Ceja
And I'll tell you a story that kind of illustrated that early on. We were only live in two markets, just Boston and San Francisco. And there was a woman in San Francisco that posted a job because her son was living in Boston, 20 years old. Unfortunately, he was going through chemotherapy treatment at Mass General Hospital, and she couldn't fly across the country to be with him during the treatment. So she hired a TaskRabbit in Boston to visit him everyday in the hospital for a week. To bring them a healthy meal and a cozy blanket, sit with him for 30 minutes every single day and then call her afterwards and give her the update on how he was doing.

Mayra Ceja
Now, the tasker that picked up the job in Boston happened to be another mum. And so the bond that these two moms formed across the country was just really incredible. And I think it was at that moment that I realized what we had created went far beyond just jobs, tasks, scenarios, that it really was redefining who your neighbors are and who you can rely on. And at that moment I knew we were going to be successful.

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Mayra Ceja
That's an incredible story and I think right, it just makes all the daily tasks that you've had and the uphill battle, right, just that much more rewarding. So with that said, you have been a little bit public. I did do some research and I was looking at your medium post. I think you have been a little bit public in terms of the challenges of fundraising, your D round and some of the emotional stress that just launching a company takes. Can you talk a little bit about your experience with that?

Leah Busque
Yeah, I mean it's definitely not for the faint of heart. It is a total grind and it is very stressful. I think for me it was, I found the most stress and anxiety and the pressure from the people, not only the employees and the team members that were working so hard for the platform, but for the 60,000 plus TaskRabbits that were earning a living on the site every day. And so certainly keep me up at night just wanting to ensure that everyone was having a positive experience.

Leah Busque
The last round of funding we did, I've said it was the hardest round of funding and that was a surprise to me. It was like we needed $3 million and it was a very small amount of financing that we needed to get to profitability. But at that stage of the company it would've been easier to go out and raise a $50 million growth round and not just a smaller, $3 million get us to profitability round.

Leah Busque
And so it was a real, it was a real grind. We met with hundreds of investors and it was very stressful, and at one point I remember we were like two weeks away from not making payroll and it took a toll certainly on me and specifically my body. I mean my body completely almost shut down. I ended up in the hospital in the emergency room with a stress induced colitis and my colon almost burst and I was in the hospital for five days being pumped full of antibiotics to solve the internal issues caused by stress.

Leah Busque
And at the same time I was on the phone with investors in the UK and London trying to get this $3 million round close. In the end I did, I got it done and I got it closed and the company went on to be successful and profitable, and that's ultimately what made us so appealing for IKEA to acquire us. But I think so many times, there's this stress in this underbelly of running a startup that not many people talk about. Because I know for me at the time I didn't share those stories because I didn't want to look weak. I didn't want to look weak to my investors or my team members or my employees or have anyone question how the company was doing.

Leah Busque
And so I think now being on the other side and being an investor, I have so much empathy for founders who are raising money, who are running companies, who are building and scaling. And I think as an investor it's important for me to be able to say, "Listen, you have to take care of yourself as a founder. You have to prioritize your health as a founder. And that's what makes not only you sustainable, but your company is sustainable as well.".

Leah Busque
And so that's been a real focus for us at Fuel. Both Chris and I are really behind this philosophy and this belief that we don't only invest dollars, but we really invest in the people. And so we've been running events around Founder Health and Wellness. We're calling these events Refuel, which kind of goes along with our brand at fuel.

Leah Busque
And in fact, we're running our first ever founder retreat in October, which is going to be two days and one night completely dedicated to our founders health and wellness. So taking a little bit of a different approach, I think so many times founders feel so much pressure from their investors just to perform. But the reality is, as an investor, it's important for you to just say to your founders too, like, "I care about you and your wellbeing as well.".

Mayra Ceja
So you transition over the conversation right now into Venture Capital, which brings me to my next question. After years of operating a business, why did you decide to transition on to the investing side?

Leah Busque
It wasn't an obvious decision at first. I mean, I had run TaskRabbit for almost a decade. It was a decade of my life. I knew that I didn't want to go back and operate again. I feel like TaskRabbit was my first baby, my first child. I had seen it grow up. It was now graduating and off to college and didn't need me anymore, which as the founder was really fulfilling to build something that lives beyond you.

Leah Busque
And then since then I've had two more real children, like human, the real need children. And so I thought, I want to utilize all these experiences and skills that I've developed over the last 10 years, but I don't think I want to start another company. I don't want to have a fourth baby. And so, I got pulled in the direction of Venture by a lot of different people and a lot of different funds.

Leah Busque
I had over the years pitched hundreds of investors and most of them said no to TaskRabbit, but I had kept strong relationships with a lot of those people. And I realized that, as an engineer, what I really missed was being able to stay at the forefront of technology. And I had just put my head down in one company, in one business for almost a decade and I kind of missed out on the new technologies that had emerged. I completely missed out on the wave of AI and VR and Blockchain was something new and up and coming. And as an engineer I was very interested in those technologies.

Leah Busque
And so I thought, "You know what? Venture Capital is a great way to kind of be able to dig into a lot of new areas all the time and constantly learn new things, which I love. And then I think the second thing I realized is my favorite time at TaskRabbit was when we were under 20 people and we were small and just getting started and really innovating. And so the idea of early stage investing and really partnering with early stage founders at that really critical early moment of inception was really interesting to me.

Leah Busque
And so now I get to kind of relive those days over and over over again through our portfolio. And then getting to work with Chris, who's built an amazing platform at Fuels, just been really fulfilling.

Mayra Ceja
Now for those of you in the audience that don't know, Chris, Chris is your partner Chris Howard, who's amazing and I want to thank him for originally introducing us. Now, if I recall correctly, Chris told me there was a funny story about how you guys originally started to decide if you guys were going to work together, involving coaching sessions.

Leah Busque
We did a lot of things before we decided we were going to work together. Specifically, I knew at some point I wanted to go into Venture and then I knew at some point I wanted to focus on early stage. But then the question was, is like, "Who do I want to work with every single day?" And joining a venture fund is a huge commitment. It's decades long. I had spent eight years at IBM as a programmer. I had just spent 10 years running TaskRabbit. I was looking for something that would be the next phase of my career for a couple of decades and beyond.

Leah Busque
So when Chris and I met, we were matched up by Megan Quinn, who's a growth investor at Spark. And she knew that Chris was looking for a partner. She knew that I was talking to Venture Funds. And so Chris and I met over coffee one morning in our neighborhood, and we really just hit it off. And so we started meeting for coffees, every couple of weeks and then once a week. And then I started coming to his office a couple of days a week and it organically grew from there.

Leah Busque
But one of the tools we used is this tool called the Hogan Assessment. And it's something I had to use at TaskRabbit when I was hiring Stacy as my COO and some other key hires in the company. And the Hogan Assessment is really a personality test and you answer a bunch of questions and then you can debrief with an executive coach who can talk to you about how your personalities are complimentary and how they match up when things are going well, when things are not going well, areas that you, and values that you share, and other areas where you may be really, really distant on.

Leah Busque
And so Chris and I did this assessment and we sat down with Chris Holmberg, the Executive Coach to do the debrief, and we found that we had a lot of complimentary values and that also we had different skillsets that would be complimentary. For instance, he tends to like to be a little bit more behind the scenes. And I don't mind kind of coming and chatting with you right on this podcast, and so that's very complimentary.

Leah Busque
But we have strong values around how we want to work with founders. We have values around how analytical we are in decision making. We have values that are shared around just a financial manageability and sustainability. And so that was a really, really helpful process that I've used now a couple of times to pick the right partner. And so it's something that I'll probably continue to recommend and continue to use for these types of things.

Mayra Ceja
What is the most often advice you give, you find yourself giving to founders?

Leah Busque
Most often I'm telling founders to not overthink, not over analyze, not get paralyzed by perfection. Many times people can get so paralyzed by wanting their ideas to be perfect or wanting that code to be perfect or the experience to be perfect before they put it out there, that they just never put it out there. And so really it's something that I learned at TaskRabbit because I was the same way in the beginning, but just really pushing yourself to a zone that feels uncomfortable, but that enables you to get feedback, the good and the bad, so that you can iterate and operate quickly and make improvements.

Mayra Ceja
How has your perspective changed now that you're sitting on the other side of the table?

Mayra Ceja
I don't know if my perspective has changed, but I'd say I'd certainly have. I've learned a lot. For instance, one of the biggest surprises for me being on the other side of the table is as an entrepreneur, as a founder, I was always so worried about the competition in my space. I was worried about, when we first launched TaskRabbit, I was worried about Handy and Zara Lee and there was one called Aid In Anything and there was like a million errand running apps that I'd be really stressed out about.

Mayra Ceja
But now on the investor side, I realize that there's, sure the categorial competition that a founder has to face, but as an investor there's also this portfolio that I'm managing, and so founders in the portfolio have to think about who else, what other companies are in that same portfolio as them and as their investors are managing their portfolios, how are they making decisions and trade offs between time spent in companies, dollars going to companies, how are they making prorata and follow on decisions in companies.

Mayra Ceja
And so what I didn't realize as a founder is that the portfolio dynamics of my investors portfolio actually really matter, maybe just as much as sort of the competition out in the marketplace as well.

Mayra Ceja
What are the lessons that you've learned from building TaskRabbit that you most often share now with founders?

Leah Busque
Well I think there are a couple things. I think one is just really pushing yourself again around iterative development. We had a really good AB testing framework at TaskRabbit that we'd utilize to make decisions on workflows and experiences. And we would say, if we can increase user conversion by X percent, like this test worked and then we like roll out new code, I think that's all fine and good.

Leah Busque
The one challenge with iteratively building that way is that you really have to believe that you are building the right product. And I like to use the analogy that you're on the right mountain. I think about, iterating a product that way is scaling to a peak, and you want to improve, improve, improve until you reach the top of that peak. But what you have to understand is are you on the tallest peak or is there an entire mountain range behind you that is taller and bigger and more interesting.

Leah Busque
And so for us at TaskRabbit, one of the things I learned is, in 2014 we're optimizing and scaling and things were going well, but I wasn't sure that we were on the tallest peak, and we had to make the tough decision to boldly leap to a brand new mountain range and throw away all of the code and kind of start from scratch with this new mobile first, bookings platform and kind of get rid of the auction-based bidding model, which was a lot of friction for customers.

Leah Busque
And it was a bold move and it was a lot of work, but in the end it was the right call for the business, because then we were able to be on this new mountain range in this higher peak and really build and scale the company to that taller peak.

Mayra Ceja
What have been some of the investments that you've recently invested on that you're most inspired by or are proud of?

Leah Busque
Yeah. Well I'm really excited about some recent investments in the direct to consumer space. There's this company called Arjun, which is completely redesigning women's work wear, which you think about, "Oh, there's Banana Republic and there's J.Crew." But actually work wear for women has always been an afterthought, right? In those stores and those retail environments, it's like they have their core lines then they like throw in some blazers, but Arjun is really thinking about how women work, what they need to be confident and comfortable and be bold in the office.

Leah Busque
And so I really love Sally Christians and the founder and what she's doing with Arjun, so that's what I'm really excited about.

Mayra Ceja
Ah, that's great. That sounds great and now I'll have to check that one out too. Now, before we jump into a rapid fire question, I want to ask you one of my favorite questions. When was your last peak moment of happiness?

Leah Busque
Oh, probably this morning when my kids woke up.

Mayra Ceja
How much do you sleep?

Leah Busque
Not enough.

Mayra Ceja
A number, ballpark.

Leah Busque
Gosh, maybe seven hours a night.

Mayra Ceja
What was the last good book you that you read?

Leah Busque
In The Middle Right Now, Michelle Obama's.

Mayra Ceja
I love that book.

Leah Busque
She's pretty incredible. Yeah.

Mayra Ceja
Definitely, one of my favorites. What is your biggest life hack?

Leah Busque
I hack my calendar in a way where it is color coded by type of meeting and type of category so that at a quick glance I can tell what I'm doing in any given week. Am I doing a lot of interviews or investor meetings or pitches or am I on school pickup duty, whatever it is, and so it just kind of gives me a sense of trying to balance all of the things that I'm juggling in a given week.

Mayra Ceja
Do you believe in God?

Leah Busque
I think that I believe in, I wouldn't call it God. I think there's a lot of different ways to be spiritual.

Mayra Ceja
What was the last thing that made you think about quitting?

Leah Busque
Oh, think about quitting. Probably when my body broke down and I was really sick.

Mayra Ceja
Do you believe you're lucky?

Leah Busque
Yes.

Mayra Ceja
What is the worst piece of advice you ever got?

Leah Busque
Wait until it's perfect.

Mayra Ceja
Do you meditate?

Leah Busque
I do.

Mayra Ceja
Who are founders that you admire?

Leah Busque
Founders that I admire. Katrina Lake at Stitch Fix. James Reinhart at thredUP, John and Logan at Zimride or at it used to be Zimride, at Lyft. Yeah.

Mayra Ceja
What is one thing that you believe in that most people don't?

Leah Busque
I deeply believe in having gut instincts and gut reactions and following your gut on many things.

Mayra Ceja
What is your favorite song?

Leah Busque
Right now my three year old is really into Despacito and he can actually shake as little hips a little bit, so that's probably it.

Mayra Ceja
What's the biggest misconception that people have about you?

Leah Busque
I get underestimated a lot because of my size, because I'm tiny and petite and people think I'm just really friendly and sweet.

Mayra Ceja
What is your favorite thing to do when you feel demotivated?

Leah Busque
Go to SoulCycle.

Mayra Ceja
How would you describe high school Leah?

Leah Busque
Completely awkward.

Mayra Ceja
What is your superpower?

Leah Busque
I can read people.

Mayra Ceja
What do you want to be remembered for?

Leah Busque
Making people lives better.

Mayra Ceja
Thank you, Leah for coming on Venture Unplugged today. It has really truly been a pleasure to hear from you. You were so candid that I think you shared a lot of insights with our audience that I hope inspires them. Thank you so much.

Leah Busque
Thanks for having me. It's so much fun.

Mayra Ceja
Thank you.