The weight she carried for a decade

Welcome to The Corridor. My guest today helped invent an entire category, and now she is building a firm to fund the next one. Leah Solivan left an eight-year run as a software engineer at IBM in 2008, founded what we know today as TaskRabbit, pioneered the gig economy, scaled the company to forty-four US cities, raised more than $50 million, and sold it to IKEA in 2017. Now she is an investor with Precedent VC, her early-stage firm backing founders who are first in and precedent-setting. She is a proud Latina with roots in Puerto Rico, and she always puts that front and center. Leah, welcome to The Corridor.

Thank you so much for having me. I'm excited to be here.

You had eight years at IBM, a stable engineering career, and then you walked away right as the 2008 crash began to build something no one had seen before. What did you see that everyone else was missing? And were you scared?

I left my job at IBM in June of 2008. The stock market and everything really started crashing in September, and I had already left. I wish I could say I had the foresight to see the opportunity, but it played out differently.

I had the idea for TaskRabbit, and I knew new technologies were emerging—social, location, and mobile technology were very new in 2008. The iPhone had come out only a few months earlier. As an engineer, I became passionate about building on those technologies to connect real people in the real world and get real things done. That was the premise, so I left IBM.

Then everything crashed. We entered the Great Recession, and then I was scared. I realized I had left a high-paying, stable job. I cashed out a $27,000 pension from IBM, and that funded the first version of the company.

But I also saw incredible people losing their jobs. Former lawyers and teachers were looking for new, flexible ways to find work. In September I thought: what I'm building could help. This is a new way of working and a way to make money. I was scared, but I thought I could create something for this new economy—which became the gig economy—that could make a real impact.

In 2008, letting a stranger into your home to run an errand was unthinkable. You had to build trust in the marketplace before anyone believed in using it. How did you do that?

If I had told you in 2008 to jump into a stranger's car and let them drive you somewhere, people would have thought you were insane. The same was true for TaskRabbit: invite a stranger into your home to organize your bookshelf? It wasn't going to happen.

There was enormous trust that needed to be built, and I saw technology as the way to do it. We could use the Facebook platform and social networking to build trust between people. If you hired Bob to install bookshelves, gave him a great rating, and you and I were friends, then I would feel comfortable hiring Bob too.

That was the early premise: how do you build trust between strangers using the new technologies available? It was an experiment at first, but it took off. Now you'll jump into a stranger's car with Lyft or Uber.

You built TaskRabbit for nearly a decade and then it was acquired. Everyone celebrates the exit, but people rarely talk about the personal side and the letting go. What did it feel like to let go after nearly a decade?

It felt like a weight I had been carrying for a decade had lifted. I had been in survival mode for a decade—and suddenly, I survived. It was over.

It was really hard. I vividly remember the board call where we voted to sell the company. The vote was obviously going to be yes, and I thought the call would take two minutes. This was 2017, before Zoom and before COVID.

The Series A investor got on, and instead of a quick yes, he launched into a beautiful speech about how proud he was of what we had built as a company and a team, and how proud he was to have been part of it. The Series B investor did the same. By the time it reached me, I was in tears. I realized this was closing a major chapter—not just for me, but for the team and the investors who had been on the journey.

When I hung up and the sale was official, I cried. Not because I was upset or sad, but because it felt like a weight I had carried for a decade had lifted. I had been in survival mode for a decade, and suddenly: I survived. It's over.

It gave me the freedom to jump to the investing side of the table, which I have absolutely loved. I realize now that I am built to be an investor backing the next generation of entrepreneurs. Instead of TaskRabbit being my identity as a founder, it gives me credibility as an investor. I love partnering with early-stage founders and offering any shared experiences I can from TaskRabbit.

You recently founded Precedent Collective out of Precedent VC to support investors from underrepresented backgrounds. Most people focus on getting more diverse founders funded. You went one level up, to who writes the checks. Why is the investor side the real leverage point?

The leverage point is who controls the capital. GPs at venture capital firms control which founders get funded. They make decisions through the lens and experiences they bring.

Go one level up and you realize that you and I are fundraising from limited partners. The same rules apply. Limited partners decide which venture firms have capital to deploy. The system revolves around who has the power, the capital, and the check-writing capability.

The more people we put into check-writing roles—as investors and limited partners—the more we change who builds companies and who gets funded. We all bring a different lens, experience, assessment, and network. That is the big leverage point in this system.

Why did you choose the specific thesis for Precedent VC? How does it connect to your background?

Precedent VC focuses on early-stage founders building the next generation of consumer companies—category-defining, precedent-setting businesses. I focus on consumer because I operated a consumer business with TaskRabbit, and consumer has been out of favor in venture capital for some time.

But we are at a massive inflection point. AI is changing consumer behavior faster than ever. This is the moment when the next group of iconic companies will be founded, and I want to be backing those founders now.

You're a proud Latina with roots in Puerto Rico, and you put that front and center. How has that shaped how you see founders and the bets you're willing to make that others might not?

The Spanish-speaking community is the largest population group in the country—more than twenty percent—with enormous decision-making and purchasing power. Founders building for that market with that lens are going to build massive businesses.

One company I've invested in is MeSalud Health. It offers employers a telehealth service for native Spanish speakers. Employees receive care in their language, while the employer pays because it wants to keep its workforce healthy and happy. It is an incredible business and a great example of the lens I bring as an investor. That company should be funded and built. It is important to bring your own experiences when assessing companies and markets.

Tell us about your podcast, Breaking Precedent, and why you started it.

It all started with the podcast. I interview leaders across industries who are shifting society in some way. There are business and technology leaders, but also artists, activists, and politicians.

I love innovation and moving industries forward. I see people breaking precedents and setting new ones, and I want to hear and elevate their stories. The podcast has become a book, Breaking Precedent, coming out next summer. The podcast and book also led to the fund, continuing that thread of work.

What is the one thing you would tell a Latino founder building now, especially from a background or place investors usually overlook?

Get connected. Get into a network and meet people. Find opportunities through organizations like Endeavor and through your own communities. For every person you meet, ask for one more introduction: great to meet you—who else in your network should I know? That is how you get plugged in and build your own network.

Thank you for sharing your story. That is the goal of this podcast: to share the stories of Latinos who are building and show that sí se puede. People have reached the places where we want to be. It comes back to networking, connecting with people who share your interests, and providing value to those relationships. You have done that throughout your career, and as a fellow Puerto Rican, I am proud to share your story with our audience.

I'm so proud to be here with you, Angel. Thank you so much for having me.