Jul 11, 2022 · 1h 15m · how-i-built-this
TaskRabbit: Leah Solivan
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, host Guy Raz interviews TaskRabbit founder Leah Solivan, who shares how a snowstorm errand dilemma inspired one of the earliest peer-to-peer gig economy marketplaces. Solivan details the technical evolutions, harrowing pivots, fundraising hurdles, and operational restructuring that turned a grassroots errand board into a profitable enterprise acquired by IKEA.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 33.1% of the talking time here. How this is scored →
Guy as informed peer 4.0 Guest teaching 1.9 Guest disagreement 0.4 Guy pushing back 0.6
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 58:05 Pushing back on small-transaction assumptions
Leah refutes Guy's assertion that commission models on cheap errands were unsustainable, clarifying task sizes averaged $150 with 20-30% margins.
Hardest push from Guy ▶ 57:39 Guy challenges commission revenue sustainabilityGuy interrupts the narrative to question whether taking a simple marketplace commission could ever yield long-term profitability.
Biggest teaching moment ▶ 32:49 Explaining the 2008 recession's labor tailwindLeah educates Guy on how the financial crisis actually created an immediate surplus of skilled professionals eager to become Taskers.
Guy holds their own ▶ 13:59 Guy citing earlier dot-com delivery failuresGuy brings historical dot-com expertise by challenging Leah with failed predecessors like Peapod and Kozmo.com.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Preview: Realizing TaskRabbit's Need for a Mobile Shift | 0 | 0 | 0 | 0 | Introductory monologue and teaser clip. Host provides narrative context with zero direct interactive debate. | |
| Early Life, Dance, and Discovering Computer Science | 4 | 2 | 1 | 1 | Guy asks about Leah's early exposure to programming, playfully checking if she was a computer nerd building PCs. Leah clarifies she learned hands-on building PCs with her high school boyfriend. | |
| Working at IBM and Confronting Corporate Ambition | 4 | 1 | 1 | 1 | Guy contextualizes IBM as a safe corporate haven, while Leah describes how being labeled 'too ambitious' signaled it was time to move on. | |
| Exploring Entrepreneurial Ideas and Early Side Projects | 3 | 1 | 0 | 0 | Leah recounts early side projects like an anonymous real estate critique blog and dog walking sites, leading up to the snowy night dog food dilemma. | |
| Defining the Technological Convergence Behind Peer-to-Peer Errands | 5 | 3 | 1 | 2 | Guy pushes on existing delivery competitors like Peapod and Kozmo. Leah explains how convergence of mobile, location awareness, and Facebook's social graph created trust. | |
| Mentorship from Zipcar CEO Scott Griffith | 4 | 2 | 0 | 0 | Leah describes cold-emailing Zipcar CEO Scott Griffith and the weekly brainstorming mentorship that followed. | |
| Mid-Episode Break: Launching RunMyErrand Amid Economic Turmoil | 3 | 2 | 0 | 0 | Leah details customer discovery at Zoomies coffee shop and securing a closed beta with the Charlestown Mothers Association. | |
| Operating the Early Marketplace and Personal Errand Runs | 5 | 2 | 1 | 1 | Guy asks if she anticipated the broader gig economy wave. Leah emphasizes she was purely engineer-driven and focused on executing early jobs herself on a scooter. | |
| Resigning from IBM and Implementing the Bidding Engine | 4 | 1 | 0 | 0 | Discussion of quitting IBM with $27k in retirement savings and setting up the early eBay-style bidding mechanism for tasks. | |
| Citywide Expansion During the 2008 Economic Collapse | 5 | 3 | 1 | 1 | Guy notes the terrifying timing of launching during the September 2008 Lehman collapse. Leah counters that the crash created a flood of highly qualified workers seeking income. | |
| Guerrilla Marketing and Securing the Initial Angel Tranche | 4 | 2 | 0 | 0 | Leah describes guerrilla marketing stunts and the nerve-wracking angel round that fell from $250k to an initial $50k tranche. | |
| Discovering fbFund and Commuting to Silicon Valley | 4 | 2 | 1 | 1 | Leah explains accepting fbFund's reduced $15,000 offer against Scott Griffith's advice because it opened Silicon Valley access. | |
| Pitch Coaching and Shifting Focus from Technology to Value | 4 | 2 | 0 | 0 | Leah recalls bombing her initial pitch at fbFund, transitioning from technical jargon to customer value, and flying back across the country to secure Tim Ferriss as an advisor. | |
| Overcoming Boston Market Resistance and Preparing the West Coast Move | 4 | 2 | 0 | 0 | Leah explains why Boston's DIY culture pushed them to San Francisco and why the RunMyErrand moniker felt commanding and restrictive, necessitating the rebrand to TaskRabbit. | |
| Overcoming Sand Hill Road Rejections and Closing Series A | 4 | 2 | 1 | 0 | Leah describes pitching Sand Hill Road with a broken hand, dealing with bizarre VC interruptions about house cleaning, and closing $5M with Shasta Ventures. | |
| Appointing Eric Grosse as CEO and Raising Series B | 4 | 2 | 0 | 0 | Leah and Guy discuss the strategic choice to recruit Eric Grosse as experienced CEO to raise an $18M Series B, while noting the company was still too early for classic scaling. | |
| Marketplace Economics and Missing the On-Demand Mobile Shift | 6 | 3 | 1 | 3 | Guy presses Leah on the viability of taking small commissions on low-ticket errands. Leah corrects him by stating average task size was $150 with healthy 20-30% unit margins, while acknowledging they fell behind mobile-first competitors. | |
| Resuming the CEO Role Amid High Burn and Strategic Misalignment | 4 | 2 | 0 | 1 | Leah reflects on returning as CEO, managing high cash burn, and executing painful layoffs while six months pregnant under extreme medical stress. | |
| The Booker T Product Overhaul and Direct Booking Backlash | 5 | 3 | 0 | 1 | Guy notes how frustrating the old bidding interface was. Leah details the high-risk 'Booker T' pivot to direct instant booking tested in London despite loud domestic backlash. | |
| IKEA Partnership, Achieving Profitability, and Acquisition | 4 | 2 | 0 | 0 | Discussion of IKEA furniture assembly being the dominant use case from day one, leading to an in-store retail integration and eventual 2017 acquisition. | |
| Founder Legacy, Hard Work, and the Role of Serendipity | 4 | 1 | 0 | 0 | Closing reflection on founder emotional detachment post-sale and the classic How I Built This question balancing luck versus relentless execution. |
Statements from this episode (26)
Leah Solivan disengages from problems others can solve just as well
“I only like to work on problems that I feel like I can uniquely solve. And if I feel like there's someone else who can also do it and do it just as well, like, I become very disengaged and very bored and uninterested in working on it”
Solivan: Bought RunMyErrand.com on GoDaddy for $6.99 on the spot
“I typed into my iPhone into GoDaddy, runmyerrant.com, and the domain name was available for six 99. So I bought it on the spot,”
Solivan: Facebook's social graph creates sufficient trust for peer-to-peer services
“And so I saw Facebook as a way to leverage the social graph to build trust between people. So if I could tell you that, You know, you need your dry cleaning picked up, and the person that was gonna pick up your dry cleaning was two degrees of separation from y…”
Solivan: Mashing up social, location, and mobile enabled new marketplace platforms
“I saw those three technologies, social, location, and mobile, and I, that was what was interesting to me at the time. It was like, I can mash up these three technologies and create a new platform that no one has launched before.”
Solivan: First pivotal advisor reached for TaskRabbit was Zipcar CEO Scott Griffith
“The first person that was sort of pivotal that I reached out to was Scott Griffith, who was running Zipcar.”
Solivan onboarded the first 30 RunMyErrand runners via in-person interviews
“Yeah, I met everyone face-to-face to start, because I was terrified that, you know, there was going to be a trust and safety issue early on. And so I met them all at Zumi's Coffee Shop, thirty-minute interviews, and I brought on 30 of them to start the site.”
Solivan: Did early TaskRabbit errands personally on a scooter
“I ended up being the one doing a lot of the early jobs. I had this little scooter that I rode around Boston, a Charlestown area, and I would do a lot of the early jobs myself, and so I would then get, like, first-hand knowledge of what it was like to be A task…”
Solivan: Cashed out $27,000 IBM pension to fund RunMyErrand
“So I had 27,000 dollars in my IBM pension program that, you know, we could withdraw with a penalty because it was your retirement. But I was like, whatever, let's just withdraw this money. And so I gave myself like six months to make something happen.”
Solivan: 2008 Crisis Flooded TaskRabbit With Laid-Off Professionals Seeking Errand Work
“It was overwhelming. And the, I mean, the skill sets, and the talent, and these people were educated, and they'd gone to college, they were pharmacists, they were lawyers, they were teachers, they were being laid off. And they were looking for new ways to make…”
Solivan: RunMyErrand closed a $50K angel tranche in March 2009
“And the investors say, let's start with 50 K. We'll give you 50 K. Let's see how you do. So we start with 50 K. That was March in 2009.”
Solivan: Boston Was Only TaskRabbit's Tenth-Largest Market at Scale
“Even at scale with TaskRabbit, Boston was like number 10 market. For us.”
Solivan: Facebook Offered $15,000 for Equity to Join fbFund Incubator
“So we get the offer from Facebook to come out to do the incubator program. It's 15,000 dollars. And it's for a chunk of the company. It's like, you know, a few percentage points of the company.”
Solivan: Received a two out of ten on first fbFund pitch
“So day one, they get us to stand up, introduce ourselves to And give our 32nd pitch. And they, it's like 20 companies. And then we get rated on how well we did on day one. Out of 10. I got like a two.”
Tim Ferriss became RunMyErrand advisor and made introductions to Floodgate and Baseline
“And I asked him to be an advisor. And on the spot, he says yes. And he says, and I want to introduce you to my good friends that are investors, Ann Miraco at Floodgate, and Steve Anderson at Baseline Ventures.”
Solivan: Boston's DIY culture hindered TaskRabbit, requiring a San Francisco move
“I think the culture of Bostonians is a very do-it-yourself mentality. And so that was some friction for this type of service, and I felt like if we could just get to San Francisco, where, you know, it's the tech company capital of the world, like, this is the …”
Shasta Ventures offered TaskRabbit a $5 million Series A term sheet
“And so then they put together a five million dollar term sheet.”
Solivan: TaskRabbit Hired an External CEO Too Early to Scale
“I think when I look back, it was more about timing because the business was too early. To bring in someone that was a step away from the core vision, and the business still needed me to really drive the momentum forward. He was brought into scale. It was too e…”
TaskRabbit Raised $18M Series B Led by Lightspeed
“And it was the largest round that we raised. It ended up being eighteen million dollars led by Lightspeed.”
Solivan: TaskRabbit averaged $150 task sizes with a 20% to 30% commission
“You know, the main revenue stream was the commissions, and the average task size at that time was about a 150 dollars.
And so it, the number, the numbers worked.
We took anywhere between 20 and 30% of a task, and that was, you know, net profit to us.”
Solivan: TaskRabbit users averaged one post monthly, limiting scale
“And so the lever in the model was always this repeat usage metric. Like if you could get someone to post two tasks a month or one time a week,
That was the huge lever in the model that, like, really made all the numbers work.
But on average, people were postin…”
Solivan: TaskRabbit was burning probably over $1M monthly in 2012
“I mean, at that point, I think we were burning probably over a million dollars a month.”
Solivan: TaskRabbit laid off around 20% of its 80-person staff in 2013
“So it ended up being about 20% of the team. At that point, we were probably 80 people, and so it was under 20 people that we transitioned out.”
Solivan: TaskRabbit's direct booking model doubled metrics in London pilot
“Thank God we launched this new product in London, because we saw it work. We saw the mobile product work, this on-demand booking platform. It worked. The metrics doubled, the repeat usage, and we're like, ok, this works.”
Solivan: TaskRabbit had 1 million users and 60,000 taskers during direct-booking pivot
“Now we need to take a million people in the US and 60,000 taskers that are on the platform, and we need to transition them to a completely new way of working.”
Solivan: TaskRabbit would have abandoned direct booking without London pilot validation
“Thank God we launched that London product, because if we hadn't, we would have been completely overwhelmed by that vocal minority, and we could have pulled back. We could have completely decided not to move forward, just based on the feedback, because it was s…”