Marco Zappacosta
4 min readSep 30, 2015

Building Thumbtack: Six Years, Forty-two Rejections, and a Singular Obsession With Solving One Big Problem

A few years ago, Thumbtack was just a handful of people working out of a rented house. We were excitedly chasing a dream without any pay, my co-founder was sleeping in a closet, and there was this constant existential fear of running out of money.

Benefits of not working in an office: no shoes, no socks, no problem (2009).

We were determined. We wanted to make hiring a plumber as easy as buying a book online and we weren’t going to take “no” for an answer. Well, at least not the final answer.

When we attempted to raise our Series A in Fall of 2011, we got rejected — not once, not twice, but 42 times! It was pretty brutal. With our bank account close to zero, we started discussing how we were going to let go of the entire team. But even in the face of defeat, we could see our dream off in the distance. There was just a mountain (and a desert, and maybe a lava pit) in the way.

Fast-forward to today: we’re announcing a $125 million investment on top of last year’s round of funding, which we’ve barely touched. Our feelings range from holy-shit-what?! to sincere gratitude. We not only survived, but now have a war chest to keep building toward this audacious dream.

It’s Not Just About The Numbers
We now have more than 200,000 active, paying professionals, millions of customers, and powerful recognition from investors. But big numbers don’t come close to what I see in person, every day.

I was at breakfast with 70 of our pros on Friday, listening to their stories. They truly see us as partners in their success, and we’re so unspeakably proud to help them realize their dreams.

Meeting with D.C.-area pros at Thumbtack Connect in September 2015.

What if every electrician, caterer, and piano teacher could stop worrying about the constant hunt for new clients — if pros could just focus on what they love to do. And what if everyone had shorter to-do lists and could spend more time on the important things: their families, their passions, their happiness.

Those what-ifs are why we get up in the morning. That’s the world we’re excited to build.

Still Obsessed With Solving The Same Problem
We have a lot of work to do, but the end-goal is the same. We’re building a one-stop-shop for confidently and easily hiring any local professional. What’s in the works:

Hyper-intuitive matching: We’re much more like a dating service than a directory. We’re matching two very unique sets of requirements: aligning the specific needs of one individual with the skills and availability of another. There are so many stipulations: location, timing, materials, budget, preferences, and more. It’s a hell of a challenge.

We’re tackling it pretty well for millions of customers already, but we can do better. We need an even more granular matching algorithm that’s shockingly perceptive.

An end-to-end experience: We want to be able to help with a project’s entire lifecycle. The more tools we can provide (payments, scheduling, invoicing, business management, etc.), the faster and easier our customers can get their projects done and the more our pros can focus on what they do best: providing an incredible service.

We’re Just Getting Started
Today, we generate $1 billion in revenue for independent small businesses every year and have more paying pros on our site than both Angie’s List and Yelp combined. All of this, and yet we’ve only scratched the surface.

Local services is a $700 billion market in the U.S. alone. It’s no wonder players like Google and Amazon have recently gone after the same space. There’s a lot of opportunity here. But in the end, it’s going to come down to whoever can best solve this very tricky problem. And with money in the bank, offices full of smart people, and enthusiastic pros and customers by our side, we feel damn good about our odds.

P.S. If you like problem-solving and creative thinking as much as we do, we’re hiring. Join us.