Reflecting on My Failure to Build a Billion-Dollar Company
By: Sahil Lavingia
Tags: Leadership, Startup, Business, Venture Capital, San Francisco

It doesn’t look too bad, right? It’s going in the right direction: up.

But we were venture-funded, which was like playing a game of double-or-nothing. It’s euphoric when things are going your way — and suffocating when they’re not. And we weren’t doubling fast enough to raise the $15M+ Series B (the second major round of funding) we were looking for to grow the team.

For the type of business we were trying to build, every month of less than 20 percent growth should have been a red flag.

But at the time, I thought it was okay. We had money in the bank and product-market fit. We would continue to ship product and things would work out. The online creator movement was still nascent; the slow growth wasn’t our fault. It always looked like change was right around the corner.

But now, I realize: It doesn’t matter whose “fault” it is; we hit a peak in November 2014 and stalled. A lot of creators absolutely loved us, but there weren’t enough of them who needed our specific product offering. Product-market fit is great, but we needed to find a new, larger fit to justify raising more money (and then do it again and again, until acquisition or IPO).

For the type of business we were trying to build, every month of less than 20 percent growth should have been a red flag.

In January 2015, after our final double-or-nothing hail-mary, our bank balance dipped below 18 months of runway. I told my 20-person team the road ahead would be a tough one. We didn’t have the numbers to raise a Series B, and we would have to work really hard over the next nine months to get even close. To that end, we deprioritized everything except features that would directly move the needle. Many were not core to our business, but we needed to try everything we could to get our monthly processed volume to where it needed to be.

If we succeeded, we would raise money from a top-tier VC again, hire more people, and pick up the journey where we’d left off. If we didn’t, we would have to drastically downsize the company.

In those nine months, when the whole team knew we were fighting for our company’s life, not a single person left Gumroad. From “this is gonna be hard,” to “yep, turns out it was,” every single person worked harder than ever.

We launched a “Small Product Lab” to teach new creators how to grow and sell. We shipped a ton of features, including weekly payouts, payouts to debit cards, payouts to the U.K., Australia, and Canada, various additions to our email features, product recommendations and search, analytics to see how customers are reading/watching/downloading the products they’ve purchased, and add-to-cart functionality. And that was just between August and November.

Unfortunately, we didn’t hit the numbers we needed.

Slim down or shut down?

Looking back, I’m glad we didn’t hit those numbers. If we’d doubled down, raised more money, and appeared in the headlines again, there would have been a very real possibility of even more spectacular failure.

With that off the table, our options were:

Shut down the business, return the remaining money to investors, and try something new.

Continue with a slimmed-down version of the company to aim for sustainability.

Position the company for an acquihire.

Some of my investors wanted me to shut down the business. They tried to convince me that my time was worth more than trying to keep a small business like Gumroad afloat, and I should try to build another billion-dollar company armed with all of my learnings — and their money.

I tended to agree with them, to be honest. But I was accountable to our creators, our employees, and our investors — in that order. We helped thousands of creators get paid, every month. About $2,500,000 was going to go into the pockets of creators — for rent checks and mortgages, for student loans and kids’ college funds. And it was only growing! Could I really just turn that faucet off?

If I sold the company, it would be mostly for our stellar team — and I would no longer be able to control the destiny of the product. There were too many acquisition stories of companies promising exciting journeys and amazing synergies to come — and ending with a deprecated product a year later.

Selling was certainly tempting. I could say I sold my first company, raise more money, and do this all again with a new idea. But that didn’t sit right with me. We were responsible to our creators first. That’s what I told every new hire and every investor. I didn’t want to become a serial entrepreneur and risk disappointing yet another customer base.

We decided to become profitable at any cost. The next year was not fun: I shrunk the company from twenty employees to five. We struggled to find a new tenant for our $25,000/month office. We focused all of our remaining resources on launching a premium service.

In June 2015, a few months before our layoffs, our financials looked like this:

Revenue: $89,000 for the month

Gross profit: $17,000

Operating expenses: $364,000

Net profit: -$351,000

A year later, in June 2016, our monthly numbers looked like this:

Revenue: $176,000 for the month

Gross profit: $42,000

Operating expenses: $32,000

Net profit: +$10,000

It hurt, but it meant creators would keep getting paid. It also meant that we were in control of our own destiny.

From skeleton crew to lifestyle business

It got worse from there.

Gumroad was no longer the venture-funded, fast-growing startup our investors and employees signed up for. As everyone else found other opportunities, the skeleton crew fizzled from five to one.

I was basically alone. I didn’t have a team, nor an office. And San Francisco was full of startups raising gobs of money, building amazing teams, and shipping great products. Some of my friends became billionaires. Meanwhile, I was running a “measly” lifestyle business. It wasn’t what I wanted to do, but I had to keep the ship from sinking.

Now, I understand some people would dream to be in that position. But at the time, I just felt trapped. I couldn’t stop, but there was only so much I could do as an army of one.

For years, my only metric of success was building a billion-dollar company. Now, I realize that was a terrible goal.

I shut off the rest of the world. I didn’t tell my mom about the layoffs — she had to read the article and tweets herself to find out. My friends were worried, but I assured them I was neither depressed nor suicidal. I left San Francisco for long stretches at a time, thinking that some travel would give me adequate distance. It only made me more lonely.

Every day, I woke up and took care of all of Gumroad’s support queries. I tried to fix all of the bugs I could. Often, I had to ask for help from former Gumroad engineers. They were all employed by then, but they always found time to help. Once all things Gumroad were taken care of, I tried to go to the gym, and if I had the willpower, work on a side project (a fantasy novel). Most days, I failed.

To me, happiness is about an expectation of positive change. Every year before 2016, there was an improvement in my expectations — in the team, the product, or the company. This was the first time in my life when the present year felt worse than the last.

Living in San Francisco was already a struggle. When Trump won the election, I ended up leaving for good.

New beginnings

Then one day, everything changed. Again. I’m wary about sharing this part of the story, because I don’t know if there is anything to learn from it. But it happened, so here it is.

On November 27, 2017, I got this email from KPCB, our lead investor:

I am following up our conversation a few months ago. KP would like to sell our ownership back to Gumroad for $1. Can we discuss this week?

Mike had left KPCB to start a new company, and KPCB didn’t want the operational headache of appointing a new board member. Plus, it helped their taxes. In one fell swoop, our liquidation preferences (how much we would have to sell for before dollars started going to employees) went from about $16.5M to $2.5M. All of a sudden, there was a light at the end of the tunnel. Small, dim, and far away, but present. There was a path to an independent business, not beholden to the go-big-or-go-home mentality I signed up for when I raised money.

One investor joined them. We’ve bought back a couple more, since then. I keep the rest of the investors up-to-date with a brief email every few months.

The future came into focus: I could grow a small team, slowly buy back our investors, and build Gumroad into a meaningful business focused on our creators. We would never become a billion-dollar company, and that started to feel okay. Certainly, the thousands of creators selling on Gumroad wouldn’t mind.

Finding new forms of impact

The eight years I worked on Gumroad were full of personal ups and downs. There were months where I worked 16 hours a day, but there were also some months where I worked four hours a week. Here’s one way to picture that time: