Year One Lessons of Entrepreneurship

A little over a year ago, I got on an airplane and flew from Albany to Colorado for the purposes of a meeting of the minds with Stephanie. We had done some work together via the Erb Institute and the energy of it was still flicking around us like static electricity.

I was a bit nervous. I knew (and I now know Stephanie knew too) that we had to have a Put-Up-or-Shut-Up conversation in order to go forward. Four days, many flip chart papers and sticky notes, Fort Collins craft brews, shared meals and excited exclamations later, and we had agreed to start a business, wolf & heron, with a set of core values, a focus on influence, and the desire to change the way people think and act.

At the start of Year Two with Year One (caps definitely intended) in the books, we can’t believe how far we’ve come, and how little we knew about what we were taking on when we decided to set out in the first place. In the spirit of one of our core values, Exploration, we like to look inward and backward before we look forward. So, what did I learn?


1. Oh partner, my partner.

I respect the partnership we have created. Yes, we challenge each other (it’s healthy). Yes, we’re in different time zones. Yes, we also share many passions and skills (we make sense together). Being an entrepreneur is mentally taxing. Together, we can navigate those ups and downs much better than we could on our own. When I’m low, she brings me up and vice versa. And our creativity is multiplied by each other. Ideas need to be shared. Aside from the business benefit, Stephanie is someone I trust and adore and as we sometimes joke, someone whom with I can’t wait to co-write a book about our partnership.

2. Routines can be fun.

One of the first cultural decisions we made as a business was to not let the paperwork or bureaucracy or - yuck, routines - get in the way of our desire to enjoy life. The weekly strategy meeting was dubbed “Weekly Awesome.” Stephanie’s ringtone on my phone is, “All I do is Win.” Our KPI tracker is called, “Fun with Numbers.” Our sales pipeline spreadsheet is weirdly beautiful and satisfying. And all of that helps us enjoy the day to day, even when we’re not immersed in the joy of product development or delivery, but end up spending hours on the little things that also need doing.

3. Experimentation is everything.

This is best piece of advice we heard from everyone, and finally internalized. The Lean Startup says it much better than I can, but testing our ideas quickly without putting all our eggs in one basket is one of the most critical things we’ve figured out how to do. Our goal last year was to learn and adjust. And we did. For this year, we have a much-more-finely-tuned business model and plan, with a hard core focus on selling our programs into businesses.

4. Begin as you aim to continue.

At first blush, this may seem like the opposite sentiment of “experimentation is everything,” but it’s something I say to Stephanie every time we’re asking ourselves, “should we do this?” We might be only two people right now, and a baby company, but that doesn’t mean we shouldn’t be operating, at least from a mental space, like we’re wearing big-girl pants and representing what we want right from the beginning. That means being ourselves, being inclusive, being intentional about giving, and setting up a CRM system that will allow us to grow even though it’s probably more than we need right now.

As we look ahead, we have developed a spreadsheet universe with detailed goals and key metrics for next year, but essentially it boils down to a few priorities.

  • Continue to do what we do really well - make amazing experiential professional development programs.
  • Invest more time in creating and selling enterprise professional development solutions - scaling our existing workshops to meet our customers’ needs.
  • Go big or go home. We’re stretching the stretch goals and showing up like a boss.

What did you learn this year? How are you taking that through to your 2018 planning?

-- Kara Davidson, co-founder, wolf & heron