Rest in Pieces: How My Failed Skateboard Company Became a 20 Million-Tech Startup

I’m Harley, CEO & Co-Founder at Nooklyn, a Brooklyn-based tech startup fixing the experience of finding apartments and roommates.

I was born and raised in downtown Manhattan in a loft next to the Brooklyn Bridge. Just two blocks away from the loft was the infamous Brooklyn Banks — an iconic skate spot— and it was there alongside some of the most legendary skateboarders that my dream of opening my own skateboard company began. I imagined all the ads and videos we would film and the success that would come.
First, I needed a name for my company. I was in history class when I began adding “skateboard” to the end of every word in the dictionary until I landed on “substance.” Substance Skateboards — it clicked for me. Later that afternoon, I skated over to Staples and ordered a thousand yellow and black stickers from a hand-drawn sketch. I was so excited, but in hindsight, the name was problematic. The name had implications of addiction and in today’s world of information overload, a long company name is a slow death.

It was an exhilarating time to grow up in the greatest city and experience all of the entrepreneurial ups and downs. We handed out t-shirts and plastered stickers all over town before having money to purchase inventory. I hired a freelance designer, now a UX manager at Nike, to design our first decks and logo. The shirts and stickers created a buzz that turned into demand, and shortly after I secured my first order and the backing of an investor.

We started a team of talented skateboarders who shared the desire to be industry outlaws. We went to every skateboard event and sold our products just above cost from the back of our van. We organized contests and tours to promote Substance Skateboards, all while living on Pizza, Taco Bell, and cheap beer. We landed a few distributors, recruited sales reps and targeted East coast skate shops. All of this only delayed the inevitable failure.

After three years of hustle, I got the call from my investor. He was at a hotel drinking heavily and had forgotten I was coming. He told me he had to withdraw all future financing, but in a last effort to help, he had set up a meeting with the owners of a nearby ski shop. By the time we showed up to pitch, it turned into a makeshift intervention for my investor. Between my lack of experience and my investor’s issues with both substances, the company was over.

Substance Skateboards was a labor of love with razor thin margins and all of the liability of upfront inventory costs. We had little control over manufacturing and net-30’s were an industry standard curse. The team and I weren’t financially prepared for this failure. We were evicted from the house where some of the team and I lived. I personally invested over 100K and lost it all. I let myself down. I let my team down. This dream was over.

After this substantial failure, I landed a superintendent gig at a 140-unit building in Bushwick. I thought I knew what a day’s hard work meant until I had to deal with people’s actual garbage. I met Joseph Friedman, now Nooklyn’s COO, while doing some repairs at a vacant loft in Bushwick. Joseph needed to find renters and I knew a lot of people. Fed up with the garbage gig, I called Joseph and asked him if I could make a living renting apartments. Joseph explained in detail how it was possible to make over 10k per month renting apartments and his honesty and confidence was all I needed. Within weeks I was back on my feet (or skateboard) and renting apartments. Thank you, Joseph!

Injecting Substance into Nooklyn

Like Substance Skateboards, Nooklyn had scrappy beginnings focused on creating early revenue and demand. I started Nooklyn as a blog focused on keeping our apartment listings up-to-date. The first year my total investment was $10 for the domain. The first thing I did was add links to the Nooklyn blog from each of my free online apartment ads and then tested responses for different phrases. I targeted neighborhoods we could reach by bike or skateboard. I printed folders that looked like for rent signs so whoever walked out of our office was carrying around a “For Rent” sign.

In 2010, researching the real estate industry became my obsession. There was no shortage of generic and barely functional websites with lifeless design and dry, overcompensating descriptions. The biggest challenge of renting apartments was that the process was too inundated with scams, unsafe and anonymous websites, messy paper applications, and complicated payment processes. This gap in transparency was a serious issue for renters — and it was Nooklyn’s opportunity to change things.

A vital part of what makes Nooklyn different is our culture. The skateboarding world has a unique culture of community, family, and uses art to connect people from all over the world. I bought this kind of family culture with me to Nooklyn and it’s influenced every decision since. From day one, our goal at Nooklyn has been to find people a home that is just right for them. The process of navigating the real estate world can be a difficult and tricky one — and we’re here to help. We make it simple and enjoyable for everyone on and offline. Our priority in nurturing a supportive and family-like work culture can be seen in our results: We have helped more people find apartments with less staff than any other company I know of. We also have industry-leading retention rates with our employees.

We promote our Nooklyn culture in a variety of ways. After we’ve successfully put our renters into their new homes, we give them a curated welcome box filled with locally sourced products for their new home. We’re also involved with coordinating a large community-driven block party with The Bushwick Collective, a street-art non-profit. Jadakiss performed for 12,000 people at the last block party and Fat Joe performed the year prior. We believe that your home is more than your apartment — it is the neighborhood and community you live in. To highlight this, we take photos of thousands of local businesses to feature on our social platforms. Our website and app also helps prospective renters discover what restaurants, local hubs, and other neighborhood gems are close to their interested apartments. We decided early on to focus on the renter’s experience so we built a free roommate network. Our passion for community and home bleeds into our marketing and everything we do.

An important lesson I’ve learned from my time at Substance and Nooklyn is how to identify leaders, delegate and give away control. I hired Moiz K. Malik — now our third partner and CTO — initially as a freelancer to design our site. Now, Moiz oversees our engineering and design team. Without giving Moiz control over the product, my vision would still be a vision. I have met many founders who are adamant about holding onto control over aspects of business that aren’t their greatest strengths. Focusing on just the things that I’m good at and passionate about is the only way to stay motivated and scale effectively. Building a company is a long, difficult journey. Creating a company that has even a slight impact on an industry is even harder. If you want to limit your chances of failing, find great leaders, build a great culture and delegate.

Since January 2015, we’ve moved 16K renters, processed $36M in rental payments and scaled the company to over 250 people as of Oct 6th 2017. Our mission is to fix the experience of finding apartments and roommates. We’ve found great people who share our mission and the desire to build a lasting company. My failures have taught me to embrace obsessions, ditch labors of love, create early demand and focus on the consumer’s experience.

Put some substance into your startup.