How we went from bootstrapping to doing Y Combinator

YC interview invites are coming out! For many, getting into Y Combinator feels like an offer you can’t refuse. You’re now a part of an exclusive, illustrious club with the likes of Airbnb, Stripe, and Dropbox! Who’d say no to that?

But when Dalton called my twin brother Harry to tell us we were in, we weren’t sure whether to take it. We thought that YC was only for a certain type of company, and ours wasn’t like that. Today, 5 months later, we’re happy graduates of the Winter 2019 YC class. What changed?

We’re bootstrapping!

Rewind to October, 2018.

Harry and I had unsuccessfully applied to YC twice before. This time, though, we were set on bootstrapping.

We had already built BookWithMatrix and All the Flight Deals. They had good traction and were making enough for the two of us to live comfortably in San Francisco.

(We’re also very frugal people. You can find us at Popeyes at the corner of Divisadero and Hayes every Tuesday for their $2.49 fried chicken. It’s amazing. And amazingly cheap)

Harry and I planned to keep building small, niche projects like these. We would grow our current project and get to build whatever struck our fancy. The Indie Hackers community showed us it was possible.

Dropping the YC application in the mailbox

We applied to YC in October, 2018 almost on a whim. This was our third time.

Every time, we’d:

  • Realize the deadline’s coming up about 1-2 days before the application deadline
  • Frantically spend a few hours writing an application, record a video, and dash to submit

This time around was no different. We thought, “YC only wants companies that could be huge. What could be a billion-dollar company?” We applied with just an idea: to bring a version of the travel blogging site Mafengwo to the US.

  1. We loved reading trip blogs and itineraries as the starting point of our travel planning, and
  2. Millions of people in China do too (including our parents and friends who read Chinese), where Mafengwo is $2 billion company.

We sent it in, and then went back to working on our actual project at the time, a hotel price tracker.

“We got an interview!”

A month later, we hear that we’re invited back for an interview! All the while, we’d been working on this other project that has nothing to do with our YC application. We were not ready.

We immediately set out to talk to friends who used Mafengwo, the Chinese travel-blogging platform so that at the interview, we actually knew what we were talking about. We also scheduled practice interviews with Ruby and Max, two friends who had gone through YC before. (As an aside, if you get an interview invite today, definitely practice . YC interviews are 10 minutes. You want to talk succinctly and use them well.)

In the course of talking to everyone, we realized that:

  • It’s still our company: We feared that YC would force us down a hyper-growth path we weren’t happy to go. But as the YC partners remind us many times, it’s still your company. YC just owns 7% and has some really experienced, helpful partners. At the end of the day, you decide how fast to grow and how to fund your business.While YC would love for every company they fund to become billion-dollar businesses, there are many others that end up doing OK. For every AirBnB or Stripe, there are 10 companies that end up more like the Recurse Center, who said “We’ve had linear growth, but a constant good time.” YC understands that, and doesn’t try to turn your company into something it can’t be.
  • (That said,) this could be big: Unlike BookWithMatrix, the idea is not so niche it has to be bootstrapped. Even though we were working on the hotel price tracker , our friends loved the idea of planning trips from itineraries and blog posts. This idea had a large audience, and we were eager to build it.
  • We should optimize for learning: As first time founders, we don’t know what we don’t know. Sure, we’ve done growth, engineering, and product for Google, Stripe, and our side projects, but there was much about running a company, growth, and (if it came down to it) fundraising that we could learn.

I still remember one quote from Ruby which really stuck with me. I asked her:

How did YC change what you were going to do?

Everything we did, we’d have done eventually, but YC made it happen faster. We might have done something in 9 months anyways, but during YC, it happened in 3.

We then interviewed. We didn’t mention that we were working on the hotel price tracker; the idea itself in fact barely came up in the conversation. When we got the call from Dalton inviting us to the batch later that Tuesday, we were already starting to be convinced of how doing YC was the right choice.

After another round of calling founder friends who both had and had not done YC, all the reasons above really came together — especially the first, that it’s still our company. We called our parents and then Dalton back on Wednesday to accept. We were in!

The YC kickoff: “the same things, but faster”

The next day, we rented a Getaround and drove down on Thursday afternoon for the YC kickoff.

At the kickoff, we first had a brief talk by Michael Seibel about some logistics and the importance of starting work immediately, not just when YC actually started in January. “It’s a race to demo day!” Then we met our group partners, Dalton, Adora, and Solomon. Everyone intro’d themselves and talked some logistics.

Afterwards, as we were mingling, we came clean with Adora.

So, you know how we applied with this travel blog idea? We’ve actually been working on this other, hotel price-check tool and were thinking of wrapping that up in the next two weeks before switching to this blogging thing we actually applied with.

Adora set us straight.

Pick one. Don’t do both.

Deep down, we knew that was true. If we launch the hotel price-tracker, how can we say we’ll be done in two weeks? Just because we had some sunk costs and effort into it doesn’t mean that we had to finish it.

On the car ride home, we decided two things:

  1. We’d send out a Facebook post asking friends for their Google Docs, Sheets, and emails with travel plans and itineraries, and offer them free boba (bubble tea). At this point, we were still just trying to build a travel blogging tool, but we had an inkling that their Google Docs might be similar enough.
  2. We stopped working on our hotel price tracker, and started coding Travelchime immediately.

These were both undoubtedly the right decisions. The itineraries we got and the conversations we had delivering boba told us a ton how people really plan travel. And we really didn’t believe that much in the hotel price tracker, not to mention that it’s been done before.

YC hadn’t even started yet. But already, we were doing things we’d have done anyways, but much faster.

Want to learn more about our Y Combinator experience? We’ll blog about our Winter 2019 experience as the Summer 2019 batch passes the same milestones we did. Subscribe to our upcoming posts!