My First Startup Failed — 5 Lessons I Learned to Get it Right the Next TimeBuild the damn solution.

I’m super proud to say that I write this as the full-time CEO of my own startup, TableOne (I left my day 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 a separate post.
I want to highlight my first startup, Den, that failed. I know there are millions of founders out there with opinions and lessons learned. Still, I figured I’d share my reasons behind why it failed with the hope that it can help someone who may be where I was only 18 months ago.
First and foremost, what was Den? We were 5 guys who wanted to build a temporary storage network for your stuff (backpacks, jackets, gym bags, luggage, you name it) in major cities utilizing the extra space in hotels.
Think Airbnb for your jacket when you’re out 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 retail storefronts as storage locations, like random convenience shops and UPS stores.
Our thesis was that this type of service was a need but wasn’t widely used because of the psychological disconnect between dropping off your valuable items in a place you didn’t normally associate with safety or security. In contrast to the spots they used, hotels were also open 24/7.
At that time (Summer 2022), hotels were still emerging from COVID-19 and operating at partial capacity with loads of unused space. We thought it could be a match made in heaven to pair travelers and residents with these hotels and create an elevated version of an already existing experience — people would get access to temporary storage they trust, hotels would create a secondary revenue stream to supplement their bottom lines in a post-COVID world, and bing-bang-boom everyone would be stoked.
Product screenshots from the Den app
We built Den for 9 months, had verbal commitments from 16 hotels to run our pilot, had a couple of funding conversations, and even got a YC interview. Unfortunately, it wasn’t going anywhere, and I knew it was time to pull the plug and move on to other things (always listen to your gut if you’re feeling this). It was hard to accept; after all, it is your brain-child, and you put so much time and effort into it.
What I learned from it all, however, changed my life and has helped me to succeed in building my second venture:

1. Until what you’re building is in front of people, it is an idea and nothing more

I know everyone says this, but ship. Ship fast, ship often, ship anything. 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 versions out to real, unbiased potential users.
In the case of Den, we shipped TestFlight versions out to ourselves. We ended up creating an echo chamber of confusion as a result. Some days, we loved the product we were looking at; other days, we hated it. We’d go back and forth for weeks on what iterations should look like, but you know who we never asked? The people that were apparently going to use it.
If I could do it again with Den, before I even attempted to build an app, I would’ve spent a day creating a landing page that read “Airbnb for your jacket.” I would’ve built a simple sign-up flow into the site and left my number for people to contact me or me them. I’d maybe run an Instagram ad or two, have some friends spread the word, then camp out one October Friday night at my buddy’s apartment in the West Village, fielding jackets from people at bars to see if this is something people actually were looking to use. And guess what, if no one uses it? It probably means it’s not something I should go after.

2. Build solutions, not products

The first lesson ties nicely into this second one: build a solution to a problem instead of just packaging up a product as a potential solution. A huge thing I now realize with Den is, yes, wanting to drop my jacket off somewhere is a desire I’ve had a few times, but was it a solution I’d consistently pay ~$20 for? In all honesty, probably not. That was my issue, and even though I knew this deep down, I wanted to keep the dream alive. I wanted to keep building a product.
Looking back, the way I navigated this in my head was I tried to talk about Den only to close friends and family. If they loved me, they’d never roast my idea flat out (though s/o to my Mom for being honest with me anyway).
Your idea has to get scrutinized for it to get stronger. You have to put it in front of people and have them tear it apart for it to get better. Nothing good, effective, or useful is ever built with a fragile ego.

3. Try to do everything yourself before hiring anyone

This is the one I’m most passionate about, and frankly, it is the mistake I see other founders make most often. Whether you are technical or not — if you aren’t wireframing, trying to put together a landing page, or not attempting to do any of the gritty pieces required to build your startup BEFORE outsourcing, then you don’t give enough of a shit about what you’re building.
The idea stage of a startup should be like a virus within 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 bring it to 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 struggling to get those ideas out of you, how will you ever communicate that to someone else to do for you?
My background is in the product, so for Den, I did barebone wireframes and created a pitch deck at the beginning. From there, I gave away equity in my company to have people come 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.” Bullshit. 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 afraid and had such a rigid idea of what I was capable of.

4. A bigger team DOES NOT indicate success

I’ll be honest with you all. I wanted to grow the Den team so that I would feel less alone, so I called up some of my talented friends. When you have 4 other people working with you, the task is a lot less scary but also a lot harder. More cooks in the kitchen = more red tape to cut through.
Everyone had to be on board with decisions, there always needed to be a discussion, and that ate into momentum like nothing I’ve ever seen. We were a startup with the agility of a government agency.
To me, having a big team sent out 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, whomever you hire should bring something to the table and have their own superpower. The show 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 get-go. Don’t just hire to fill the silence.

5. Stop chasing validation

You know exactly what I’m talking about because we’re all guilty of wanting it: Funding conversations, YC applications, Forbes 30 under 30, and so forth, and what have you. Anything that makes you (and others around you) think you’re moving the needle when truly you aren’t.
I think the most ironic part was being so preoccupied with trying to get those people to notice me that I wasn’t doing the one thing that would actually get them to notice me:
Building the damn solution.