Getting Through a Startup's First Year (and finding your one thing)

This past week, we held both our board meeting and team leader meetings in successive days in our sunny Miami office. (By "sunny", I mean literally solar-powered — our new Miami office hadn't had blinds installed yet so we improvised with some disposable tablecloths hung with masking tape.)

It was an important set of meetings because it marked the one-year point since our first as a company. The good news is that we just finished up the most successful period of our startup's history since launching in Fall '14. With that, we were able to turn the page on 2015 and chart the course for 2016, and feel the wind starting to blow behind our backs.

It was a time to do a check-in on what we've accomplished, take a pulse of where we are, and set our priorities, plans and targets for the upcoming year. We also had a healthy discussion of the lessons — and in particular the mistakes — of 2015. I've used it as an opportunity to reflect.

I feel like we've gained the wisdom as a team to understand our team competencies relative to our opportunities. I looked back to where we were last year. Instead of targets based on hopes and feel, they're now based on data and a solid foundation. Instead of jumping in quicksand, we're ready to start jumping from a springboard.

Deep Thoughts

I came away with some musings I wanted to share — both to our team who stuck it out together through this first year, and to other startups finding their way. I'm also writing this to myself, in case I forget it. (It's my third startup with HealthCare.com, and I've repeated the same first-year mistakes in thinking each time. Whenever the fourth startup is — hopefully not for a long time — I need to remind myself to read this post.)

When you start a company, everything is an open field. Your vision is expansive, and it's not limited by your ability — and more often, inability — to execute on them. You're not clouded by practicalities. You assume that every idea you put out will work. You forget there will be unexpected challenges that will divert you for days, weeks or even months. You assume you'll be able to sell your vision to others — investors, clients, partners and potential hires — and that they'll buy in and find as much excitement as you have. You assume that every person you bring onto the team will know what to do, develop mastery, and meet the high expectations you had for them. Lastly, you assume that you'll know what you're doing as a founder and manager — and this is probably the biggest assumption.

Here's the reality that no one tells you (or perhaps you know, but subconsciously ignore). During that first year:

• Your ability to execute is at its most nascent
• Your team is the most inexperienced it'll ever be in working together
• Your credibility with users, partners and clients is non-existent
• You don't have any data to support any of your assumptions

You're a babe in the woods during that first year. When you're the most vulnerable is when you need to be the most resilient and the most focused.

Find Your One Thing (During Year 1)

I don't want to make it sound dire. My only advice is that a startup's objective during this first year — hopefully it can be done in less than a year — is to work like mad to figure these things out. Spend less time plotting world domination, and more time learning how to do stuff and how to be efficient with your time. And don't do too many things.

Figure out what you're really good at. Use that as a basis for your existence as a company, and try to strip away all of the things that aren't part of this.

I'll leave this post with this scene from City Slickers that says it better than I possibly could:

Curly: Do you know what the secret of life is? [holds up one finger] Curly: This.

Mitch: Your finger?

Curly: One thing. Just one thing. You stick to that and the rest don't mean shit.

Mitch: But, what is the "one thing?"

Curly: [smiles] That's what you have to find out.