Founders: Leah Solivan on building and selling TaskRabbit

Summary

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Business Daily – Founders: Leah Solivan on Building and Selling TaskRabbit

BBC World Service | Host: Sarah Rogers | Guest: Leah Solivan | July 28, 2026

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Episode Overview

This episode of the "Founders" series dives into the entrepreneurial journey of Leah Solivan, founder of TaskRabbit—the pioneering app that connects people with "taskers" for everyday jobs. Leah recounts how a simple need for dog food evolved into a transformational business and discusses the gig economy's impact, the intense personal demands of startup life, and her transition to venture capital after selling TaskRabbit to IKEA. The conversation is equal parts candid personal reflection and practical insight about building a tech startup from scratch.

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Key Discussion Points & Insights

Childhood & Early Influences (02:01–04:40)

• Family & Early Entrepreneurship

  • Leah describes her upbringing in Massachusetts; her father’s Air Force career, her mother as a stay-at-home mom, and a formative childhood curiosity about business.
  • At eight, she asked her father about the top job in a company, then started her first venture: “Pollution Solutions,” a recycling program at her elementary school.
  • Quote [02:19, Leah Solivan]:
    “I remember seeing starting my first company at that moment… I don’t really think we made much money, but I remember that vividly from childhood.”
  • She was also a devoted dancer for 25 years and harbored dreams of being an astronaut.

• Early Lessons in Money

  • Her parents gave her and her sister choices about allowance frequency, teaching her money management through practical examples.

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The Spark for TaskRabbit (04:40–06:37)

• Career Path & The “Aha” Moment
  • Leah studied math and computer science, joined IBM as a software engineer, and loved creating products at scale.
  • The idea for TaskRabbit came one snowy night in February 2008 when she needed dog food and wished for an app to connect her with someone at the store:
    • Quote [06:02, Leah Solivan]:
      “I should be able to connect with someone at the store at this very moment through this device. I bet there’s someone at the grocery store in the dog food aisle right now and I’m willing to pay them for their time.”

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Building TaskRabbit – Beginnings & Scaling (06:37–10:29)

• First Launch & Growth

  • The initial model was akin to eBay’s bidding system: taskers bid on user-posted jobs.
  • Started with 30 taskers in Boston (Charlestown), all interviewed in person; attracted high-quality applicants due to the 2008 recession.
    • Quote [07:26, Leah Solivan]:
      “I was completely flabbergasted by the quality of people... teachers, lawyers, physical therapists… looking for new ways, more flexible ways of making money.”
  • One of the original taskers, Mark Hedger, is still active on the platform.

• Raising Capital

  • Early fundraising was grueling given the recession; Boston investors passed, but she found backing in Silicon Valley.
    • Quote [09:40, Leah Solivan]:
      “You really do. You have to believe it in your bones… be willing to break through walls to make it happen.”

• Startup Life: The Demands

  • Leah describes being pulled in every direction—CEO, janitor, fundraiser, product lead, customer service.

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The Impact on Work: Gig Economy Leadership (11:38–14:21)

• TaskRabbit’s Influence & Controversy

  • TaskRabbit was among the first to shape the gig economy, offering workers flexibility but also sparking debate about job security and lack of benefits.
    • Quote [12:01, Leah Solivan]:
      “It’s a complicated thing… People just wanted to own the way they worked. But with that comes these institutional structures... no benefits programs or paid time off or insurance.”
  • Leah reflects on industry-wide challenges, and the need for regulatory adaptation and better benefit partnerships for gig workers.

• Consumer Risks & Liability

  • In the early days, TaskRabbit focused on less-skilled tasks to limit liability and built insurance programs to maintain user trust.

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Highs and Lows: Stress, Health, and Exit (15:29–17:40)

• Intensity and Burnout

  • The stress of fundraising and responsibility took a major personal toll; Leah suffered stress-induced colitis, hospitalized during a critical fundraise, ultimately closing the round from her hospital bed.
    • Quote [16:00, Leah Solivan]:
      “My colon almost burst due to the stress and pressure of this fundraise. I ended up closing the round from my hospital bed.”
  • The turning point came after years of cumulative strain, stewarding payroll, a growing team, and a newborn at home.

• Decision to Sell to IKEA

  • Selling to IKEA brought relief and a sense of timely transition for her physical and mental well-being.

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Life After TaskRabbit: Investing & Perspective (17:47–19:04)

• Health & Family Balance

  • With four children, Leah now emphasizes routines for nutrition, exercise, and mental health.

• Venture Capital Motivation

  • After TaskRabbit, Leah became a VC, motivated by a sense of “obligation to bring others along” and to offer empathetic support to new founders.
    • Quote [18:28, Leah Solivan]:
      “I really saw the opportunity to … become an investor who has a lot of empathy for founders… and to be able to really help this next generation of founders do the same thing.”

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Memorable Quotes (with Attribution & Timestamps)

• “I remember seeing starting my first company at that moment… It was called Pollution Solutions…”
  — Leah Solivan [02:19]

• “I should be able to connect with someone at the store at this very moment through this device. I bet there’s someone at the grocery store in the dog food aisle right now and I’m willing to pay them for their time.”
  — Leah Solivan [06:02]

• “You really have to want it, don’t you?”
  — Sarah Rogers [09:36]
  “You really do. You have to believe it in your bones… be willing to break through walls to make it happen.”
  — Leah Solivan [09:40]

• “It’s a complicated thing… People just wanted to own the way they worked. But with that comes these institutional structures... no benefits programs or paid time off or insurance.”
  — Leah Solivan [12:01]

• “My colon almost burst due to the stress and pressure of this fundraise. I ended up closing the round from my hospital bed.”
  — Leah Solivan [16:00]

• “I really saw the opportunity to … become an investor who has a lot of empathy for founders…”
  — Leah Solivan [18:28]

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Important Segments & Timestamps

• Leah’s childhood & first business inspiration: 02:01–03:27
• Early money lessons & family finances: 03:40–04:40
• The moment TaskRabbit was born: 05:35–06:37
• Piloting and scaling the platform: 06:49–08:39
• Fundraising challenges and moving to Silicon Valley: 08:52–09:49
• Day-to-day startup pressures: 09:53–10:29
• The gig economy’s pros and cons: 11:38–14:21
• Health crisis and selling TaskRabbit: 15:59–17:40
• Becoming a venture capitalist: 18:10–19:04

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Conclusion

Leah Solivan’s story is a compelling mix of entrepreneurial drive, personal sacrifice, and pioneering impact on how people work in the modern economy. The episode draws out not just her triumphs, but also the real emotional and physical costs of building a tech company at scale—and her genuine motivation to empower the next wave of founders. Listeners gain valuable perspective on both the business and human sides of start-up leadership.

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Transcript

[Sarah Rogers]

This BBC podcast is supported by ads outside the uk.

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[Sarah Rogers]

Hello, this is Business Daily on the BBC World Service. I'm Sarah Rogers. Today's founder is Leah Sullivan, the founder of TasRabbit, an app that connects people with taskers who they pay to help with everyday jobs like building flat pack furniture. Hi Leah, welcome.

[Leah Sullivan]

Hello. Thank you so much for having me on.

[Sarah Rogers]

Now, Leah, you started in tech before founding your own company. After a simple fr. You needed dog food and you didn't want to go out and get it yourself. Now, that relatable moment sparked TaskRabbit in 2008 and made you a pioneer of the gig economy before the mainstream. You built it into a global business, sold it to Ikea. But success, of course, did come at a personal price, which we'll talk about. Now. You're on the other side of the table as a venture capitalist and you've got a book coming out next year.

[Leah Sullivan]

Not much then, not much going on. Exactly.

[Carl's Jr. Announcer]

Yeah.

[Sarah Rogers]

So let's go back to before all that. Before you got the dog. You grew up in a small town in Massachusetts. What was family life like?

[Leah Sullivan]

My father had been in the air Force for 35 years. He worked at Hanscom Air Force Base in Massachusetts. And my mother was a stay at home mom. I have a younger sister who's two years younger than me and I remember being very interested in and very good just naturally at math. And that kind of led me to computer science in college and even way far back. I remember my father came home from work one night. I must have been, I don't know, eight years old. And I don't Know why I asked him this, But I asked him what the highest position was in a company. What is that called? And he said, it's being a CEO, a chief executive officer. And I remember seeing starting my first company at that moment. It was called Pollution Solutions, and it was a recycling program I set up in my elementary school. I don't really think we made much money, but I remember that vividly from childhood.

[Sarah Rogers]

How old were you when you asked your dad that question?

[Leah Sullivan]

I think I was probably about 8 years old. I was also really into dance. I was a ballerina. I studied dance growing up. I actually danced for about 25 years before I started TaskRabbit.

[Sarah Rogers]

That's really different from the girl who wants to be the CEO. Also want to be a ballet dancer.

[Leah Sullivan]

I know. I also wanted to be an astronaut. So there were a lot of things that I was interested in.

[Sarah Rogers]

Keeping your options open.

[Leah Sullivan]

That's right.

[Sarah Rogers]

Were you good with money? Who taught you about finances and money?

[Leah Sullivan]

I remember my parents decided to set up an allowance for my sister and I, and we would do chores, house chores, during the week. And it might be, you know, setting the table for dinner or, you know, cleaning our bedrooms, whatever it was. But they kind of posed this interesting question, which I still remember to this day, and they said, we will pay you $3 every week or we will pay you $5 every two weeks. And you can decide now. I think they were trying to see how smart we were or trick us, maybe. But I did the math and I realized, well, getting paid the lower amount, but every week frequency was better. And so that's what I chose. But I think those little lessons learned around money from saving, we're from acting fiscally responsible and just being really careful actually about money and how it was spent.

[Sarah Rogers]

You then went to college. Your first proper job was in tech. You were a software engineer for IBM, which stacks up because you were really good at maths. So you were on a really good career path. Why not stick to that?

[Leah Sullivan]

I really enjoyed my time there. I learned so much. I learned so much about how to build software that millions of people around the globe were using. And that's what really excited, actually, that I could create and build things that I knew other people were using and finding value in. And so I had the idea for what became TaskRabbit. And it was like a bug that bit me. And I wasn't able to let go of the idea. And so I did end up quitting my job at IBM four months later and built the first version of the site from there.

[Sarah Rogers]

So just talk to me a little bit more about that moment that you came up with the idea for Taskrabb.

[Leah Sullivan]

Well, it was February of 2008. It was cold, it was snowing outside, there was a big snowstorm, and I was going to meet friends across town for dinner when I realized I was out of dog food. And at the time, I had this 110 pound yellow lab named Kobe. And he kind of looked at me with his little puppy eyes and he says, we're out of dog food.

[Sarah Rogers]

Yeah, they do that.

[Leah Sullivan]

And really the key moment for me, the moment that lightning struck was when I grabbed my iPhone, because the iPhone had just come out a few months earlier. This was brand new technology that people were just starting to build on top of. So I grabbed my iPhone and I thought, you know what, I should be able to connect with someone at the store at this very moment through this device. I bet there's someone at the grocery store in the dog food aisle right now and I'm willing to pay them for their time. That was the moment where it all clicked, where I had the idea.

[Sarah Rogers]

So, I mean, it's massive now. It's in eight countries, something like 75 cities. But I want to know, what was the first version of it? What did that look like?

[Leah Sullivan]

Well, it looked a lot different than it does today. And the best in class user experience at the time was ebay. And if anyone remembers going on to ebay and bidding, bidding on products and items, that was the first version of TaskRabbit where you would go onto the TaskRabbit site, you would say, hey, I need my dry cleaning. Picked up that alert, would go out to the tasker base willing to do the job, and those taskers then would bid on your job and you would choose who you wanted to work with.

[Sarah Rogers]

And how many taskers did you have at that point? Because it couldn't have been too many.

[Leah Sullivan]

Well, you know, I started the site with 30 taskers in one square mile of Boston, a little neighbor called Charlestown. I put an ad on Craigslist saying that I wanted someone to run errands for me. And I was just overwhelmed with applications from people because in 2008, we're starting to go into the great recession. So the stock market was crashing, people were being laid off. I was completely flabbergasted by the quality of people that were coming to me and saying, I want to run your errands. But they were teachers, lawyers, physical therapists that had just been laid off from work and were looking for new ways, more flexible ways of making money. And so I interviewed over coffee to start the site. I picked the 30 that I thought I could trust to go into. Maybe not even my home, but my grandmother's home.

[Sarah Rogers]

Wow. Any of them still working with you?

[Leah Sullivan]

Yes, yes. There actually is one tasker from Boston.

[Sarah Rogers]

No way.

[Leah Sullivan]

Mark Hedger, who I interviewed. He was one of the first 30 taskers and he is still on the TaskRabbit platform today.

[Sarah Rogers]

So it's successful where you are. You've got these 30 people, but obviously you want to scale that up. How do you convince investors in 2008 to back you to get that going?

[Leah Sullivan]

Yes, it was a terrible time to raise money, a terrible time to start a business. There were more than one moment where I thought, I should just go back to IBM. This is not going to work.

[Sarah Rogers]

Really.

[Leah Sullivan]

I pitched every investor I could in Boston. Everyone said no. I then came out to the Bay Area, to California, to Silicon Valley. I had never been to the west coast before in my entire life. I was 28 years old and I remember looking around at the redwood trees and people sitting in coffee shops talking about their startups and their businesses and I thought, like, where am I? This feels like a very different place than Boston at the time. But I was able to raise money.

[Sarah Rogers]

You really need to want it, don't you?

[Leah Sullivan]

You really do. You have to believe it in your bones. I mean, you have to feel it and you have to be willing to break through walls to make it happen.

[Sarah Rogers]

At your busiest, what was a day to day in the life of Leah?

[Leah Sullivan]

Oof. At the busiest, at the height, it felt like a manic episode, honestly, because it was. You're just pulled in a million different directions. You're the janitor and you're the CEO that's fundraising. You're in back to back meetings with the team, you're talking to journalists, you're pitching investors. You're sitting with the product team and soundboarding new ideas. You're sitting with customer service and you're hearing all the complaints, all the things that go wrong all the time in a business that's scaling. And so it was a lot.

[Sarah Rogers]

You're listening to Business Daily on the BBC World Service with me, Sarah Rogers. And today I'm speaking to Leah Sullivan, founder of TaskRabbit.

[Whole Foods Market Announcer]

This is Summer at its peak. Whole Foods Market Summer Fruit Fest is your invitation to eat the season fresh, organic and bursting with flavor. Start your day with peaches and organic blueberries and yogurt. Build a grazing board with fresh fruit Prosciutto and artisanal cheese. Then fire up the grill with no antibiotics ever. Proteins and fresh produce. Savor the season. Shop summer fruit fest at Whole Foods Market.

[Carl's Jr. Announcer]

Maxing is so maxing right now, bro. Get ready for spicy chicken maxing because Carl's Jr. Is saving you big with a $5.99 maxed out double stack double stack double stack spicy chicken sandwich. Seriously, just $5.99 double stack spicy chicken. This is unreal value in the bromosphere. The new spicy chicken Max wallet friendly. Max Tasty only at Carl's Jr available for limited time at participating restaurants. Tax not included. Not valid for use within a combo or a combination with any other offered discount.

[Sarah Rogers]

It's often said that TaskRabbit helped create the gig economy. So work is being paid per gig, which is great for people that want flexibility and, you know, people want a side hustle. But the flip side of that is job security. Right. And no benefits. How do you reflect on being a pioneer of that?

[Leah Sullivan]

Yeah, it's a complicated thing because there are two sides of that coin. And, you know, when I was building TaskRabbit, of course we were focused on building, scaling the business, helping to create the gig economy. As you said, this flexibility and workforce. I remember doing these surveys of Taskers and what they valued the most. Do they value the money? Do they value the flexibility? You know, was it something else? It was always flexibility. People just wanted to own the way they worked. But with that comes these institutional structures that have been built around work, the history of work that doesn't allow for, let's say, benefits programs or paid time off or insurance. Right. And so there were all these things I knew that weighed on me, that weighed on us. It wasn't a perfect system. It's not a perfect model. It continues to evolve and change. And frankly, I think the gig economy at this point has been around long enough. I'm surprised some of these government systems and the way they're set up haven't been able to follow the trends of how work has evolved.

[Sarah Rogers]

And would you have done things differently or set up TaskRabbit different? Differently having that knowledge now, if you knew that that was going to be the direction that work was going to

[Leah Sullivan]

go in, I'm not sure there's much I could have done on my own. I think there's a lot of companies in the gig economy, including, you know, Uber and Lyft and airbnb and others. And, you know, we did all kind of band together and go lobby the government and talk through structures and programs that would be helpful. But I think it does take all of these businesses together to continue to push and offer solutions for change. A couple of things that we did that we could have done earlier and sooner were just fine. Benefit partners, Benefit programs to partner with for taskers and offer them discounts on health insurance. And maybe those were things we could have thought of from the beginning. But in the end, I mean, it really, it's a massive economy, the gig economy. And it's going to take everyone, I think, to band together to help solve some of these issues.

[Sarah Rogers]

And what about the flip side for consumers? They're welcoming people they don't know into their homes, but people perhaps taking on jobs they're not quite qualified for. Where's the liability if things go wrong?

[Leah Sullivan]

I'm no longer involved today, so I can't say today how they're thinking about this. But I can say when I was running TaskRabbit we were really focused on jobs that had less skills. So moving help, house cleaning, things that didn't require licenses or contracts. And so that was an area of focus for us because we did realize that some of these higher skilled, really professional jobs like plumbers, electricians, et cetera, that's probably not the best place to find these people. On TaskRabbit, we were focused on a much different service offering. But in the end, the liability did end with us. And so that's why we had to set up insurance programs and other safety nets so that consumers, so that clients could feel comfortable and confident using the service.

[Sarah Rogers]

Do you use it?

[Leah Sullivan]

Oh yes, I still use it to this day.

[Sarah Rogers]

Now you spoke a little bit earlier about the overwhelm of just doing everything. You did go on to sell TaskRabbit, but there was a big moment for you before that wasn't the life. I'm sure to everyone else seemed to be going really well. But the pressure of just scaling this business and making it a success, it does take its toll. Doesn't does it?

[Whole Foods Market Announcer]

Does.

[Leah Sullivan]

And you know, that sort of last round of funding that got us to profitability, which then put us in a great position to be acquired by ikea. It did come at a cost. It was a huge burden. It was very stressful. I ended up in the hospital with this stress induced colitis. We didn't know what it was, but my colon almost burst due to the stress and pressure of this fundraise. I ended up closing the round from my hospital bed.

[Sarah Rogers]

What was the moment where you thought, I've got to make Some changes.

[Leah Sullivan]

You know, I think it had been building over time. I think it was almost a decade of stress that left me at that moment. We were, you know, two weeks away from not making payroll. And at that point, we had hundreds of employees and a full cap table of investors and live in 44 markets, 60,000 people relying on TaskRabbit to make money. It was a lot of stress. My daughter was just like a year old, and so she was sleeping when my stomach pain was onset. And so I ended up calling a Lyft and going to the hospital by myself.

[Sarah Rogers]

And so that was from your hospital bed that you decided you were going to sell TaskRabbit? I mean, an amazing opportunity to a huge brand. IKEA. Was that a relief at that point?

[Leah Sullivan]

I think I felt everything at once, and I knew it was time to let it go. I knew it was time to transition. I knew it was probably good for me and my physical and mental health to transition.

[Sarah Rogers]

And how do you take care of yourself now? Of course, you've got four children and you want to set an example for them too, I imagine.

[Leah Sullivan]

Absolutely, yes. I've gotten much better about, you know, making sure you carve out time for eating well and exercising and, you know, having a good routine around mental health, too. In the end, as I look back, it was an absolute incredible journey that I'm so grateful for and feel so privileged to be able to have had.

[Sarah Rogers]

Yes, because you've switched to the other side of the table. You're not the one going out asking for money. You are being asked for money. As a venture capitalist, why did you decide to go into that? Why not? You've sold it to Ikea. You've got your work life balance back. Just enjoy the good life.

[Leah Sullivan]

You know, I think I've always felt a deep, and I'm going to use this word very intentionally, obligation to not only recognize and be grateful for the success that I've had, but to bring others along with me. And so I really saw the opportunity to move over to the venture capital side to become an investor, an investor who has a lot of empathy for founders, who has lived through a decade of founding, scaling, and exiting a business, and then to be able to really help this next generation of founders do the same thing.

[Sarah Rogers]

Leah Sullivan, I've really enjoyed speaking to you. Thank you so much for joining us and just giving us all that insight.

[Leah Sullivan]

Thank you so much for having me.

[Sarah Rogers]

Well, that's it for this episode of the Founders. From Business Daily. I'm Sarah Rogers. The producer was Nev McDermott. If you'd like to get in touch, it's email [e-mail].

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