Failure’s a real bitch isn’t it? And it’s a topic we don’t talk about nearly enough.
I experienced my first jolting failure in 2017: the end of the road for my travel startup. That moment served as a critical stepping stone on my personal journey. Five years earlier, the thrill of launching my first startup baby into the wild blue yonder was like nothing I had experienced before. Although I was in the product launch room at Zillow, that was a different animal—I was a 22-year-old intern at the time. Not a founder bringing a new product to market.
My travel startup journey entailed two full product launches. Oh Hey World enabled travelers to check-in upon arrival and share that with friends and family. We missed the Foursquare craze by a few years, and didn’t solve any real problem aside from travel bloggers updating their current location on their WordPress blogs.
We re-branded to Horizon for the second launch and answered “why use it?” question with “to find a place to stay.” The platform enabled home sharing, swapping, and exchange among friends, friends of friends, and communities. We were too early for the flexible living movement, faced monetization challenges, and only insanely deep marketing allowed us to penetrate a user’s trusted circles. (Note: I’m now an investor in Myplace, a modern private home sharing platform).
My underlying mission with both was to enable people to see and understand the world with their own eyes. Contrary to popular belief, money is not the primary reason people don’t travel. It’s fear, and you can only counteract fear with community.After five years, Horizon had reached nearly 15,000 total users. While not a small number, for a marketplace business in a travel industry that sees more than 900 million international arrivals yearly, it was pretty close to deafening silence.At the end of the day, I failed at building a consumer internet company with a worldwide customer base. We built the product, but I wasn’t able to secure the capital needed to build the team, nor unearth the viral marketing components needed to scale cost-effectively.
After shuttering Horizon, I spent a year in a dark place while processing one of the hardest emotional setbacks in my life. I had lost my meaning and identity. After getting over the loss of personal capital, burnout, self pity, and not being able to give my mother a clear answer to her “what are you doing?” question, a moment of clarity struck:Being the public figure for a global internet company wasn’t my life’s calling. I loved travel and believed deeply in the power of travel to change lives, but I had no passion for sales, dealing with the media, nor an ad model and its associated time suck economy. Convincing as many people as possible to stare at a screen was not going to be my life’s work.
A new approach was in order. One that in some regards is the complete opposite of Oh Hey World and Horizon. I reached back into what I loved most about working at Zillow: building community. Being surrounded by incredible people and providing them an invaluable ability to connect with like-minded individuals. Something small, not big.
There, I said it. It was my Jerry McGuire moment.
Geek Estate Mastermind was born for the industry I knew best: property tech. I called it the GEM.
IGNORING GREAT ADVICE
Rather than build a business with rank-and-file core values, I decided that to do right by me. A list of things I won’t do was in order. Things that would either compromise me or make my idea blend into everyone else’s.
No hiring a sales team; suckering members into a recurring charge isn’t part of the recipe for community.
No sponsored events if it means slinging anyone’s wares.
And throw self-promotion straight out the window.
Rather than accept podcast interviews, I would go deeper in one-on-one settings. For me, the written word is a more effective and enjoyable outlet.
Over the years, many have told me these are all dumb strategic decisions. If we did even one of these things, no doubt we could sell more memberships.
Instead, my “won’t do” list affords me the mental bandwidth, energy, and focus to do what I love most: relationship building, product and business strategy, and creative writing. It’s why I’m able to devote eight hours a week to a single essay and turn away paying applicants who aren’t the right fit.
As a result of sticking to my gut, the GEM community numbers more than 600 members and continues to grow—not with the hockey-stick growth expected from a tech rocketship, but at a 20% yearly clip with profitability, quality, and longevity at its core.
SUCCESS FROM WITHIN
Success is about continued focus—the absence of all unnecessary noise. Chasing everything without constraints leads to half-assed results. Picking up every penny and betting you can turn it into three is a fool’s errand.
The GEM wasn’t an overnight creation; it was 10 years in the making. Geek Estate Blog launched inside of Zillow way back in 2007. It floundered for years, having readership but falling short of being a business.
After a skipper’s view of the tradeoffs required to grow a consumer internet company, my personal monopoly would mean leaning into my core values rather than accepted paradigms. It would mean nailing the paid community that sits behind the Geek Estate Blog.
I would need to consistently show up, day in and day out, and focus on delivering the best product possible. I would need to do all of the unscalable things members appreciate—and love doing them. And, I would need to care more about our customers than anyone else, a character trait my mentor Jim Marks lived and breathed.
SHOES SHOULD FIT SNUGLY
There is immense power defining success for yourself.
And I mean immense.
It brings clarity, removes FOMO, illuminates your personal path and—perhaps most importantly—it makes you comfortable in your own skin.
I tried to make fit a media model that had worked for Zillow, rather than assess my own specific passions, expertise, and aspirations. In chasing success as defined by others, I never noticed the kernel required in plain sight all along, nor its associated monetizable unlock opportunity.
Through this journey, I’ve learned the antidote to jolting failure. Stay true to yourself, make your core values the north star, and do something you enjoy. Joy is a better happiness ingredient than money, at least that’s what I’ve found.
PS: A huge huge thank you goes out to Marc Davison for pushing me to present the story to Turn On’s audience. I rarely rarely do public speaking engagements (or podcasts), but I’m certainly glad I succumbed to the pressure. I feel honored to have shared the stage with so many incredible presenters.