The author failed with “Den,” his first startup, and shares the reasons in the hope that it can help someone who may be where he was just 18 months ago.
I’m very proud to be writing this as the full-time CEO of my own company, TableOne (I left my job last Monday). We still have a long road ahead of us, but all of that and how we got here is a story for another post.
I want to highlight my first startup, Den, which failed. I know there are millions of founders out there, with opinions and lessons learned. Still, I thought I would share the reasons why it failed in the hope that it might help someone who may be where I was just 18 months ago.
First off, what was Den? We were 5 guys who wanted to create a temporary storage network for your stuff (backpacks, jackets, gym bags, luggage, you name it) in big cities using extra hotel space. Think Airbnb for your jacket when you’re at a bar and don’t want to hold it or tie it around your waist. If you’ve ever heard of Bounce or LuggageHero, we wanted to be them. The only difference is that they used storefronts as storage locations, like random convenience stores and UPS stores.
Our thesis was that this type of service was necessary, but not widely used because of the psychological disconnection that comes with leaving your valuables in a place you don’t normally associate with security. In contrast to the points they used, hotels were also open 24 hours a day, 7 days a week.
At the time (summer 2022), hotels were still emerging from COVID-19 and were operating at partial capacity with tons of unused space. We thought it could be a perfect match to pair travelers and residents with these hotels and create an enhanced version of an already existing experience: people would have access to temporary storage they could rely on, hotels would create a secondary revenue stream to supplement their bottom line in a post-COVID world, and bing-bang-boom everyone would be thrilled.
We built Den for 9 months, had 16 hotels verbally commit to piloting it, had a couple of conversations about funding, and even landed an interview with YC. Unfortunately, we weren’t getting anywhere and I knew it was time to pull the plug and move on to other things (listen to your gut if you feel this way). It was hard to accept – after all, it’s your idea and you’ve put a lot of time and effort into it.
However, what I learned from all of this changed my life and has helped me successfully build my second startup:
I know everyone says it, but ship. Ship fast, ship often, ship all. Momentum is such a tangible thing when building a startup, and the only way to keep that spark alive in your team is by shipping your builds to potential, real, unbiased users. In Den’s case, we shipped TestFlight builds to ourselves. We ended up creating an echo chamber of confusion as a result. Some days, we loved the product we were seeing; other days, we hated it.
We went back and forth for weeks about what the iterations should look like, but you know who we never asked? The people who were apparently going to use it.
If I could do it again with Den, before I even tried to build an app, I would have spent a day creating a landing page that said “Airbnb for your jacket.” I would have created a simple sign-up flow on the page and left my number for people to contact me or them.
I’d maybe post an ad or two on Instagram, ask a few friends to spread the word, and then camp out on a Friday night in October at my friend’s apartment in the West Village, collecting jackets from people at bars to see if this is something people actually want to wear. And guess what, if no one wears it?
It probably means it’s not something you should pursue.
The first lesson ties in perfectly with the second: create a solution to a problem rather than simply presenting a product as a possible solution.
I realize now that with Den, yes, wanting to leave my jacket somewhere is a desire I’ve had a few times, but was it a solution I’d pay $20 for?
Honestly, probably not. That was my problem, and even though I knew it deep down, I wanted to keep the dream alive. I wanted to keep building a product.
In retrospect, the way I handled this in my head was that I tried to only talk about Den with close friends and family. If they loved me, they would never have held my idea against me (although I am grateful to my mother for being honest with me anyway).
Your idea has to be scrutinized in order for it to become stronger. You have to put it in front of people and have them tear it apart in order for it to become better. Nothing good, effective or useful is built on a fragile ego.
This is the one I’m most passionate about, and frankly, it’s the mistake I see other founders make most often. Whether you’re technical or not, if you’re not wireframing, trying to build a landing page, or trying to do any of the pieces required to build your startup BEFORE outsourcing, then you don’t give a shit about what you’re building.
The idea phase of a startup should be like a virus inside you. It’s all you can think about, talk about, and you’ll do whatever it takes to get it out of your body and into life. Not trying to do any of these things means you don’t have a clear enough picture in your mind of what you want to create or what problem you’re solving. And if you’re having a hard time getting those ideas out of yourself, how are you going to communicate them to someone else to do it for you?
My background is in product, so for Den I did basic wireframing and created a pitch deck at the beginning. From there, I gave away equity in my company to people to come in and do everything else. Technical development, design, operations, partnerships… all because I thought, “I’m a product guy, I can’t do any of that other stuff.” Lie. The reality was that I didn’t want to do the other stuff; I didn’t want to get my hands dirty because I was scared and had such a rigid idea of what I was capable of.
I’m going to be honest with you all. I wanted to expand the Den team to feel less alone, so I called on some of my talented friends. When you have 4 other people working with you, the task is a lot less scary, but it’s also a lot harder. More cooks in the kitchen = more bureaucracy.
Everyone had to agree on decisions, there always had to be debate, and that sapped momentum like I’d never seen before. We were a startup with the agility of a government agency.
For me, having a great team sent a virtue signal to everyone that you, as a founder, were successful. But honestly, it was completely unnecessary and did nothing except stroke my ego. When you give away equity, whoever you hire should bring something to the table and have their own superpower. The series Silicon Valley touched on this well when Richard had to fire Big Head for being a self-proclaimed “master of none.”
Think about who and what you need and communicate those expectations from the beginning. Don’t hire just to fill the silence.
You know exactly what I’m talking about because we’re all guilty of wanting it: Funding conversations, YC applications, Forbes 30 under 30, etc., and whatever. Anything that makes you (and those around you) think you’re moving forward with your startup when you’re really not.
I think the most ironic thing was that I was so worried about getting people to notice me, that I wasn’t doing the one thing that would actually get them to notice me: Build the damn solution.
