The Wilderness: Fieldnotes from One Entrepreneur’s Journey through Startuplandia

Part 1: The Origin

Almost a decade ago I began “commuting” from Reno, Nevada to Silicon Valley.

This commute included an 8-hour train to San Francisco, where I’d drop of my backpacking pack at a hostel then jump on the Caltrain to Palo Alto to make my night class at Founders Institute. I made this trek weekly from October to January, fueled by youthful vigor and excitement at the prospect of building something that matters and the dream of joining the ilk of successful bay area founders. 

January of 2011 I incorporated Zirtual, a startup born out of my own experience of working with virtual assistants to help manage online businesses.

That summer I was joined by my cofounders Collin and Erik and for the next four years we went through a blur of ups, downs, growth, investment, and ultimately a well-publicized crash landing when we couldn’t pull together more funding. On a Sunday evening that still haunts my nightmares, I sent an email to hundreds of employees telling them not to clock in the next morning. We had just enough money in the bank to cover payroll—and options of selling, or getting more funding seemed doubtful in my emotionally exhausted, anxiety-ridden mind.

Luckily, the company was saved from the startup graveyard at the 11th hour by Startups.com and still lives on as part of their portfolio—but we sold the brand for just enough to cover some outstanding payroll taxes, and then our legal entity when into something called an “assessment for the benefit of creditors”, which basically means neither Zirtual’s founders, nor investors, nor employees, saw a dime from that painful “exit”.

That was the fall of 2015.

Part 2: The Wilderness

In the world of entrepreneurship, I’ve observed two types of people.

The first are those who start a business or two, sometimes successfully, sometimes not, then at some point in their careers parlay their ambition and entrepreneurial thinking into successfully leading from the inside at an already existing company. Some will become CEOs, other managers or creatives. Often these types of hires are extremely valuable as they have experienced being both a boss, and having a boss, and have seen the ins and outs of scrappy startups and more mature firms.

Then there are the people obsessed. Those whose yet-to-be-realized ideas haunt them like demons they cannot exorcise.

This group take greater risks, often foolishly. But occasionally those follies are perfectly timed or lady luck smiles upon them and they become the success stories splashed across magazines. The foundational tales of the startup bible.

But mostly, they fail. Again, and again. They suffer sleepless nights, weeks, years, grappling with how to realize their idea. During the bad times, they sacrifice health, hygiene, and relationships. These truly obsessed people often eventually do find success; if for no other reason than they will not — cannot — stop trying.

But it is not the easy, safe, or sane, path. It is only the one taken by those who (knowingly or not) are driven to birth an idea and they cannot stop until it is realized. This painful, fret path is all they can do — because their work, is their art, and like any true artist—they cannot stop creating.

For this second group, the time in-between creating—the time when you must take on other work to pay the bills, is painful. But what is far worse, is when you’re in-between ideas. This is what I call the wilderness. The entrepreneur feels of their next big idea how romantics think of their soulmate—they know it’s out there, somewhere, they just have to keep up the faith. Occasionally they catch glimpses of it or are inspired—but then like a fever dream it escapes them again.

The wilderness can last months, years, decades. Sometimes, all that keeps them going is exactly what makes them an entrepreneur—they cannot stop and know, eventually, if they walk through the wilderness long enough—they’ll stumble upon a clearing.

 

Field notes for surviving the wilderness:

  • Accept you are in the wilderness.
  • Explore, get curious and go broad with the ideas you chase trying to find yours.
  • Help others – be a sounding board for those who are actively working on their ideas. 
  • Persevere.

 

Part 3: The Clearing

I was in the wilderness for four years, almost to the date from when I lost my last startup love. 

In a coworking space in London, at a low point—my idea finally came to me. And unsurprisingly, it had been in front of me the whole time. But I couldn’t see it.  The hard realization was that I needed to struggle, to be completely broken and then to rebuild slowly and grow as a person—to be ready for my idea to finally show itself.

In the wilderness, I was lucky to have some awesome roles, including working with Calm.com when they were just a dozen people and traveling the world with a co-living startup called Roam. I launched a recruiting agency, Avra Talent, to help early-stage startups hire their first fifty people, with the goal being to (a) pay the bills and (b) interact with interesting startups that would hopefully inspire me to find my next thing. 

For the longest time I’d been obsessed with the idea that there is an ideal role for each person and an ideal person for each role, but what that solution was—I hadn’t the foggiest. That’s why I continued to narrow down my work while I was in the wilderness from Operations to Recruiting, to launching the agency so I could work hand-in-hand with hiring managers and founders to see their pain points. 

I’ve recently found out this invention of mine isn’t unique, and in fact it has been used by many entrepreneurs in the past—the term they use is “Labs”. I great story around how the founder of Gigster used this model to find his next thing is here.

Part 4: The New, New Thing

In 2020, we’ll be launching Inde, a platform that matches remote professionals with employers looking to hire the best talent, regardless of geography. Inde combines a thorough vetting process with unbiased career guidance to help professionals find a job they’ll love, and employers find the perfect fit for their role.

I’m both incredibly excited, and deeply tired (the wilderness takes it out of you!). But we have an exceptional team and I couldn’t be more blessed to be able to build something from the ground floor with them.

The last half-decade has been some the hardest years of my life, both personally and professionally, but I am so grateful that I was able to persevere through the pain and force myself to keep open to situations, people and opportunities. Growth is hard. Life is hard. But the one thing no one can take away from you is the learning you gain from each experience. Each difficult situation, a divorce, a bankruptcy, losing a job, a death, is a choice—it can either break you, or be part of the hardwon experiences that make you… 

And try your best to keep an open heart, through it all… that’s where the magic happens.