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What nobody told me about starting a business was that successful people actually fail. A lot.
Starting a business is hard work. If you hear about a company that was an overnight success, either the founders had unlimited financial resources to outsource all of the work to experienced lieutenants or they had a really good PR department.
My first business was a website development company that I started when I was 12.
It was 1999, and the web was still just a fun thing that I could be creative on. Money wasn’t a focus – the only things I really spent money on at that age were books and Lego sets. My real motivation was to get challenging projects that helped me improve my coding skills. The business never really went that far, but I continued to build websites for random projects that I created for myself over the next decade. The skills I built during this time would end up being invaluable in the future.
Fast forward to 2009. I had just graduated from college in the midst of a global economic meltdown, and was in Washington, DC working for a government contractor.
I saw friends with 6 figure salaries right out of college get laid off after just a few months on the job, and I saw the ugly unemployment figures for people my age. By contrast, the day-to-day within the government agencies we worked with as very much ho-hum, low urgency. There was such disconnect between how government actually worked and the people who relied on it for support, as well as an apparent disposability of individual people within the corporate world. The time I spent in DC forever turned me against trusting the government or an employer to take care of my long term financial security. Employment was for when I needed to pay my bills as I figured out how to shape my skills into a scalable business.
I started my second business later in the year, as the technical co-founder of a three-man startup team that sold carbon offsets to middle America online.
I still think the concept has a lot of growth potential. But two months into the project, I discovered that while I had built an app prototype, complete with algorithms, one of the cofounders was completely uncommitted while the other just didn’t do much at all. My stake was only 15%, but I was expected to do all of the work to actually build and ship the product. I could have pulled a Zuckerberg and spun out my own thing, but I ultimately didn’t care enough about carbon trading for it to be worth my time. Needless to say, the startup died when I decided to call it quits, and the breakup was ugly.
My third business was just a total failure of execution across the board.
It was an app called ThoughtEngine that analyzed your emails, suggested follow-up actions, and automatically built to-do lists for you with due dates. Again, the concept still has a lot of potential. From the start, though, I made every wrong decision possible. No cofounders, relying entirely on (very cheap) offshore hired guns, no marketing plan, a laughable crowdfunding campaign, building with HTML5 instead of a native app. Pick a startup mistake, and I made it. The end product was garbage. Enough said.
The real story for the vast majority of founders is that there are sleepless nights worrying about whether you have enough runway, product shipping deadlines, fussy clients, and keeping your teammates motivated.
The reason why failure is so common is that there is no standard set of guidelines for success. And the advice you get is bad, or at best, contradicts what someone else equally as smart has said. In the end, you have to rely on instinct to navigate ambiguous situations. But instinct, like any skill, is honed through trying and failing.