Building Sail—A Year of Failure

Jesus Christ. This is tough. How do you summarize the most important thing you did, in the most life-changing year of your life?

This is a letter to myself and my teammates, reflecting about my life in 2019 with regards to building Sail, an app where friends can build habits with each other. There are going to be two main sections.

One, product and YC lessons. Two, team and life lessons.

If you need more context, here was an update I wrote 5 months into building Sail, and here was a reflection about our YC interview experience.

Product & YC

Product and YC is easy — we’ll start there.

We spent 6 months reading books, doing “user research”, and debating best design. Then, the big day came. After 6 months of blood, sweat, arguments, and tears, we finally launched. And proceeded to accumulate a whopping 0 users.

Ryan said it best, we spent “6 months lightly jogging in circles”.

Takeaway 1: Don’t talk so much. Just build it. See what happens, because you can’t predict the future. Your first version is going to suck, so do it quick.

The second we found out about YC interviews, my mind went crazy.

“We should do X feature! Hm, maybe Y feature! Let’s make a tournament, and get a bunch of users, and prove to YC that we have users and show them our numbers and show them how impressive we are!”

Spoiler: YC was not impressed.

They didn’t care about our 100 users. They wanted to dream big, and imagine an awesome future. The tournament was kind of a good idea, but that clearly was not the feature that was going to propel us to 1B users. We couldn’t even convince them that our base product value was awesome enough for users to want our app.

Should have started there.

Getting 100 users in a week was kind of cool? But not impressive at all to VC’s and said nothing about the sustainability of our product.

“My mom loves Fitbit with her friends, why the hell would she use your app?”

- Michael Siebel to Us, 2019, YC Interview

Takeaway 2: Know what’s important. You can validate something quickly, but if you don’t spend a little time thinking about what is most important to validate, you’ll just be wasting your time.

So we spent a year scrambling around, trying to figure out what the hell to build (and to my great credit, not doing very much building). The app just never seemed awesome, to anyone. Maybe the tournaments could have been great, but deep down, I knew the reality. Sail’s initial MVP just didn’t feel that awesome.

So, we made little adjustments, argued about stupid things like boxes and streaks, and never built anything of substance.

To my actual credit, after the tournament idea, I must have subconsciously known we were going down a stupid fucking path, because I wrote a long thing about how we should pivot and double down on a social media-like angle. However, no one could read through my incoherent paragraphs of thought, even if they wanted to. Which they didn’t — I barely even wanted to read my own shit. Communication and momentum were just too poor, definitely need to improve on both those fronts in the future.

Good news is; I think I am being more clear and focused in terms of product vision now that I’m working with Tim & Angad. Go me.

Takeaway 3: Communicate candidly, build fast for momentum, and don’t lie to yourself when your idea is shit. And then do something about it.

At the end of the day, we built a habit app that you could invite friends to, with much difficulty. The UX was bad, and our killer feature was that you could kind of tell when other people did their habits, too. And, chat them. Not that killer.

After the first 6 months, we should have known that tiny changes wouldn’t have changed shit. Nicer UX wasn’t going to make our bad app amazing — we didn’t solve the problem of habits aren’t fun with a focus that was laser sharp.

Although I will say, nicer UX would have probably gotten us more users and definitely would have made more of them stay for longer.

Takeaway 4: Solve one problem INCREDIBLY well. Don’t lie to yourself when you aren’t solving that problem. I should really learn design.

—

Team & Life

Oh boy.

First of all, I fucked up with Kevin. He was our first designer, and worked with us for the first 6 months before we silently agreed that we shouldn’t work together anymore.

I wanted to believe that he was going to output some great stuff, but he didn’t. I should have recognized when he didn’t, and taken over design and removed him from the team. Instead, I was too scared to take on the full responsibility of design, so we kind of half and half did it until I got sick of months of little to no progress. I never even truly communicated my concerns to him. We just sat in weekly meetings, over and over again, re-setting audacious goals; never hitting them.

There must have been an issue in the way I set our system up, or communicated what we needed across to him, and somehow cut his motivation in half. I’m not entirely sure what happened, but I do know that he is capable of working really hard and doing good work. I just never figured out how to get him committed to doing so with our product.

Either way, should have kicked him out months earlier. It was a huge mental drag on me, and meant I was actively letting myself lose to my fear of being responsible for design. Even worse, it slowed Young and Ryan (eng) down and whittled down our overall team’s trust and momentum.

Dead in the water.

“ ”

- Our lack of communication, 2019

Takeaway 1: Don’t over hire. Do as much as you can with as few good people as possible. Communicate candidly. Fire when needed. Please. Learn. Design.

About 8 months into the project, we brought in Cindy, our next designer.

She was much more organized, consistent, and thoughtful about her design. Literally, the opposite of me. Scary, but just what we needed!

It was amazing to have that consistency. We chugged along, it felt good, pumped out designs, things looked a little better.

While our output did speed up, we butted heads — a lot. At first, small issues, but more philosophically later on, too. We did not agree on the idea of speed VS quality, or even what the product vision was. I am all about speed, and eventually believed that our product should be focused on the social rewards of doing a habit, rather than the habit itself. She is all about quality, and believed that we needed to enforce the regimental aspects of habit building; sticking to a schedule, being punished for failing.

It’s important to note that I’m sure both ideas would probably work if a great team executes well with focus. You would at least learn much more committing to one route, building quick, and being honest with the results. I just stubbornly believed that my ideas would work better.

I didn’t know how to convince her, she didn’t know how to convince me. This meant that we never made any real product decisions. We just… compromised somewhere in the middle. The worst way to build product. Not to mention, I didn’t talk to enough real, hyper-targeted users, and the user research I did do wasn’t substantial. Partly because no one used our app or paid for it. Hmm…

Even worse, we still managed to talk a whole lot while never making product decisions—let alone build.

I think I needed to be more biased about bringing people on the team. Cindy is great and I truly do love her as a human, but god damn it was impossible for me to work productively with her for this particular product, in our particular stage, with our (lack of) certainty and progress. Maybe another time and another product.

The good thing is, this time I tried to make sure we gave feedback more explicitly, at least one time amongst the four of us. There wasn’t great enthusiasm around giving each other feedback, which I was truthfully not super happy about. This whole year-long-experience was an experiment with self-growth for me, and I was (maybe unfairly) trying to push that agenda across to everyone.

At the end of the day though, I heard from and chatted with everyone on the team one-on-one. The candid conversations helped me step back and see what might be causing the dynamic of our relationships. Still struggled to solve anything at that point, as both of us were dug very deeply into our respective trenches of thought.

Takeaway 2: Move fast and learn something; compromise and learn nothing. It’s more important for us to be right, instead of me to be right. Be biased with who I work with. Work with few people. Candid conversations are critical. Just learn design lol.

I think it’s important to point out that these takeaways in the context given probably get me to a local maximum — shit is already not great, I gotta move forward, so hey I should have not worked with anyone and fire anyone who I suck at working with. Duh, that will be easy. But that also does nothing to help me avoid the shitty situation in the first place.

My hypothesis, for now, is to really trust my gut on who I choose to work with. Especially designer-wise, it feels like I cannot for the life of me work well with designers. Very different than my experience working with engineers. Either way, be picky and feel really good about my teammates.

—

When our team started working on Sail, we weren’t even sure we would finish building it. When we started watching Startup School lectures, Young literally told me “Haha, YC would never fund a stupid habit app like us, anyway.”

I replied “Haha, yeah. Probably not.”

Takeaway 3: Don’t shoot yourself in the foot before the first step.

After all was said and done, after we walked away from Sail, Young said something to me while I pitched him my next idea and asked for his feedback.

He said “It’s easy to poke holes in ideas. Anyone can poke holes in ideas. Who the hell thought it was a good idea to live in a stranger’s home, or sit in a stranger’s car.”

What a fucking great reminder of why I should not give too many fucks about what people say, but give very many fucks about what users do.

Takeaway 4: Poking is easy. Sometimes, you just have to build and see.

In this past year, I got a taste of committing to something that I felt was both against the norm and a great life decision. I think most people initially viewed my taking of a gap year as risky or even undesirable, so to commit and to see it pay off truly handsomely is probably the real win here. Especially considering I had no set plans for all of 2019 until February… of 2019. LOL.

I was fortunate enough to experience two very different and perspective-shifting internships, took a stab at YC and snagging $150K, made incredible lifelong friendships and teammates, learned to build slightly better product, and now feel more confident about the decisions I make.

I hated myself, I doubted myself, I worked fucking hard, and I loved myself. Kind of a dope way to spend a year.

“How the fuck did we get here.”

- David to Young, 2019, YC interview

Takeaway 5: Trust my own decision-making process. If I’m going to fuck up and hate my life, I’d rather do it on my own terms than blindly follow someone else’s projection of themselves onto my life.

Takeaway 6: I really love working with people I consider my teammates.

Takeaway 7: I really hate working with people I consider my teammates.

Takeaway 8: Do this more.

Takeaway 9: I absolutely cannot wait to prove everyone wrong.

It’s been roughly four months since we stopped working on Sail. We’re in the midst of COVID, and life is insanely different than what it was just one year ago. I’m very privileged to still be able to write and reflect on my experiences during this time.

Now, I’m working with Angad and Tim, who have never really built a side project coming from a “startup” perspective before. To date, we have tried validating 3 different products in the past 4 months. We were invited to interview not once, but twice for YC this past batch (not sure if this has happened before… we kind of cheated the system and ended up only being allowed into one of the interviews haha), and are launching our current product now and building much more in the next few weeks. We’re trying to solve a real problem VERY well while being honest to ourselves.

We’ll see what happens!

—

While I’m really, really excited for the future, I also love reminiscing about the past. This past year was incredibly special for me. Sail was an outlet for all of my leadership, creative, and product juices. A sandbox to play in and get fucked up by the 25-year-old middle school bully. Perhaps one of the best, worst, and most important years of my life.

Thank you for believing in me and sacrificing just as much as I did, if not more, along the way.

P.S. Still very convicted that habit building with a social-first and fun approach is going to dominate the market one day. Let me know if you’re building it!