Should a non-technical founder hedge against failure?

By Hayden Williams , written on November 10, 2013

From The News Desk

Recently I grabbed coffee with a founder whose startup is in a similar stage to mine. I reached out to him after he signed up for our networking platform. Because he had also started his career in finance I was interested to speak with him.

We shared the challenges we were dealing with, our product roadmap and plans to monetize our products. Towards the end of our conversation, we veered into the personal dilemmas early-stage founders face. He asked me, “What’s your plan if, worst case scenario, Treatings fails? Would you go back to finance, start another company or join an existing startup?”

It didn’t take me long to say what I wouldn’t do, namely return to finance. But I had a less clear answer on what I would do. It’s not something I’ve spent much time pondering. While I don’t know what I’d do, I told him, I wouldn’t have a fundamental objection to joining someone else’s company. He then gave me the following piece of advice: develop some expertise. "Startup CEOs don’t make for great employees," he said. "While we get exposure to every part of running a business that doesn’t necessarily translate into marketable skills.”

I thought about it and realized how right he was. I’ve loved experiencing all aspects of building a product and company. I’ve learned about product development, UX/UI design, copywriting and even picked up a bit of front-end coding. But, I’m not so experienced in any one of those areas that I’d be a desirable candidate for a specialized role at an established company.

This brings up the question: should a non-technical founder hedge against failure? Our goal with Treatings is to hit an inflection point before running out of money. But, even if we shut down tomorrow I wouldn’t have enough money in the bank to sit on my thumbs for months to figure out my next step. After bootstrapping Treatings for the last year, I’ll eventually need an income. The plan is to generate money from employer-branded Treatings pages that feature employees offering to get coffee with outsiders interested in working at the company.

No matter how confident I am that we have created a valuable tool to monetize Treatings, am I supposed to be thinking about a contingency plan just in case we’re proved wrong?

This predicament is unique to a non-technical founder. My co-founder Paul tackled the challenge of stepping into the role of CTO, despite having never developed a web application. He bolstered skills picked up in his academic and professional background in computer science to build our site. Through grit and sheer man-hours, he has developed a skill set that every tech company in New York is desperate to throw six-figure salaries and kegerators at.

As for me, though, I doubt many are rifling through LinkedIn for people who occasionally blog (about their bunk bed), know a little front-end code (can change button colors sometimes) and have experimented with copywriting (know every synonym for “networking” in the English language).

Of course, some startup CEOs come into the role with expertise that would make them marketable in a variety of specialized roles within a startup. But, for non-technical startup founders who came from a different industry, I think in many ways the role of startup CEO on a small team (two, in our case) is conducive to becoming a jack of all trades, master of none.

For this reason, the founder I spoke with dedicates an hour a day to front-end code so he can become more technical. One of the advantages of this habit is that the same skill that would make him more marketable in the event of his startup failing also makes him more productive in his current role.

Unlike him, though, I don’t have any kind of backup plan. In fact, all I’ve done is rule out leaning on the most profitable skill I have (willingness to bask in the glow of Excel and PowerPoint, creating bank merger models for an amount of time out of my control). At this point, I don’t feel the need for a backup plan. It’s not because I think having a hedge is a sign of weakness, and it’s not because I think Treatings is fail-safe.

I’d like to think that the marketable expertise I’m learning is the holistic skill of how to build a company. There are legal, product, business and team decisions that must be prioritized and dealt with. Most of what I’m learning is through trial and error, but I’m learning just the same.

Is this skill transferrable outside of starting your own company? Maybe it’s time to think outside the box.

With all the time I’ve spent in coffee shops over the last year, perhaps I could become a barista. Given Treatings is all about treating strangers to coffee, we’ve been able to conduct many customer interviews and other meetings in coffee shops, concealing the fact we have no office and a caffeine dependency. The problem with that, though, is I’ve never ordered off the country club menu (anything other than black/iced coffee). I wouldn’t know how to make a grande decaf no whip soy Frappucino. More importantly, I’m follicly challenged in the moustache department so wouldn’t even look the part.

With my bunk bed familiarity, perhaps I could brand myself as a feng shui expert for dormitories, summer camps and hostels. Kids and travelers have phones they need to protect and pillows they don’t want to lose from the devastating two-story fall off of top bunk. I’ve experimented with solutions for both. Paul and I have also MacGyvered some under-bunk bed clothing storage solutions that IKEA might be interested in.

Or, I could just embrace the grizzled, failed tech founder and troll around Meetups and other networking events, desperate to find others’ ideas to crap on. You know those people, whose eyes gleefully light up in conversation when they find a perceived weakness in your product or business strategy they can highlight.

There are just so many exciting options to choose from.

[Illustration by Hallie Bateman for Pandodaily]