Today marks the end of the first week of Gain Compliance as a real company. By “real company”, I mean that the founding team has been in the same office, working full-time, with money in the bank, as an incorporated, tax-paying entity, etc. This is the most recent in a series of defined milestones. For example, looking backwards:

  • Last Monday, our first day of operations.
  • Previous Friday, we had a funding close.
  • Two weeks ago, I started the move into our new office space.
  • Four weeks ago, I circulated legal documents for our funding solicitation.
  • Nine weeks ago, I formally chose legal counsel and signed the engagement letter.
  • Ten weeks ago, I had a fairly-formed business idea and started the first draft of a business plan.

In retrospect, it’s been a whirlwind, and to an outsider might look like it’s gone predictably and smoothly. With the perspective of three prior startups in my history, this assessment is generally accurate, but materially incomplete. What’s missing — the part of the process that routinely is glossed over — is all the work, effort, stress, and angst that fills the space between the milestones.

The fuller story looks more like this:

On May 6th, I left a job and a company that I adored. It paid well, and it was going well. Great team, great product, great role, etc.

On May 7th, I was unemployed. But, I had two friends with complementary backgrounds who shared an interest in a founding a startup, and we were kicking around several ideas. The principal accomplishment of the first month was essentially discarding two initial concepts in favor of third: a software solution for data quality issues for the U.S. insurance market. (That’s another part of the entrepreneurship tale that isn’t typically shared: the best plans often focus on highly technical, and, in reality, fairly boring, niche markets.)

In the past three months, I have spent countless hours on idea research and refinement, and I have told the company story hundreds of times. I’ve been conducting market and product discovery, meeting with accountants and lawyers, and pitching potential investors for money. And, I’ve heard “no” more than a few times.

It’s been consuming and stressful. While there are certainly highs in the process, there are also many lows.

To fast forward from business idea to actually starting the company, the milestones make for a good investor and public story. The true founders’ story is always a lot messier. (Incidentally, my two favorite books on this are Mission in a Bottle and The Hard Thing About Hard Things which highlight the stress of a startup over and above the outcome.)

Contrary to the simplified stories of successful startups, I wouldn’t describe the startup process as glamorous in any way. Still, to me, it’s incredibly fulfilling and exciting, and there is nothing else I’d rather be doing.

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