Milwaukee to Chicago Century Ride and Entrepreneurship

On 19 October 20204 at 7:30 am, I set out on a Century ride from Milwaukee to Chicago on my trusty Aqua Kona Sutra touring bicycle with two great friends, Jody Jankovsky and Stephen Boyle. They were both in better physical condition than me and I warned them I might be slow. It is good to ride in groups for there is safety in numbers. This wasn’t my first time on a long ride or even taking this specific ride, yet it was going to mark a major milestone in recovering from a major health scare a few years back.

I think of this ride and my journey in building a sustainable business. The parallels are grand.

I started Wiglaf in May 2002 but redirected the endeavor in January 2008. We moved from “quantitative marketing”, a term which meant something to me but nothing to the market, to “pricing”, a simple and more focused practice. The shift towards pricing was a major business development yet it wasn’t the first time I had embarked on a new intellectual and business journey.

Starting in Milwaukee, we rode through the city streets to reach some open country as we entered Racine on the MKR and Oak Leaf trails. Signal directions to the team. Cross tram tracks at an angle. Realize when Google Maps was leading us down an inappropriate path and use the sun itself to guide us south. It is a simple straight shot south from Milwaukee to Chicago, I joked it was all downhill. We laughed barely at my bad joke. Both cities are on the Michigan Lakeshore and at the same elevation.

Starting a new chapter for Wiglaf had some similar predictability. First, discuss the endeavor with my life partner Yvette to ensure we were both ready for this endeavor. Second, roll out of new branding: add “Pricing” to the name, create a new logo, make a new website, and explain what problems I solve to new people in a dedicated manner.

Around mile 60 in Winnetka, I began feeling fatigued. From this point forward in the ride, I knew I could hop on a Metra train to002 take me into Chicago. Every time I reached a Metra station, I would pass it and tell myself “Not yet, keep going.” Mile 66.6 and I thought “I am two-thirds there, let’s see if we can hit three-quarters. Mile 75 and it became “That’s three-quarters, let’s get to four-fifths.” I kept that math in my head till mile 80. The math kept my mind amused so I could ignore the fatigue.

Likewise in entrepreneurship. I find myself pushing through barriers only to find a milestone, then push past that milestone to reach for the next one. Each accomplishment quickly became history and it is time to focus on reaching the next one.

In business, every quarter starts anew with the opportunity to improve over the last quarter or the same quarter last year. Each initiative’s success leads to the next initiative but with an easier path to reach its goal. Some might call this a flywheel effect, we used to talk about network externalities, but that was too much of a technical economic term and was no match to the marketing communication juggernauts of Silicon Valley.

At mile 80, I entered CTA land, Evanston, and then Chicago. I no longer needed a Metra to get home, I could simply catch the L or put my bike on the front of a bus. I was exhausted but fully relaxed mentally. Riding for hours is an exercise of meditation. No worries in my head after eight hours of quiet meditation while passing through forests, by the lakeside, and down low-traffic street. Just fatigue and determination. Safety however continued to be a high priority, and when you’re tired it becomes a importance increases. Being a safety-conscious rider living in a city, I tend to be a little vocal and use hand signals. Part of this is to signal to drivers and pedestrians my existence so we avoid an unnecessary accident. Part of this is to make sure that when, and it will happen, I get cut off or engage in conflict, I stay in good cheer and perhaps put the other party at ease. To hit this latter aim, I wave and say hello to strangers, pedestrians, and people waiting to cross the street. One time, I greeted a man with “Good Afternoon” and he responded, “Good Afternoon, how you doing.” I confessed cheerily and declaratively “I am TIRED.” He laughed and replied, “Keep going, you’ll make it.” That was all the encouragement it took to ensure success.

As a bootstrap entrepreneur, I am well aware of the need to engage other willing supporters in my endeavor to help reach the goal. A graphic designer of talent. A security-minded web hosting service. A marketing communications manager driving engagement. A software development team to build simple tools for pricing professionals. And of course, fellow consultants to help get the work done. Then there are the truly external organizations such as DePaul University where I teach, and the Professional Pricing Society where I speak. And the publishers that help me get my books out. Entrepreneurship, even solo entrepreneurship, isn’t solo work. You have to ask for and receive help from others to reach the goal.

We completed our ride and planned on visiting a gym for a much-needed shower and much much-desired visit to a whirlpool before eating a much-deserved high-protein and calorie steak dinner. The gym was closed. I was distraught and ready to give up but one of my riding companions asked about alternatives. Thankfully, a solution was found. We showered and dined. No whirlpool but victory nonetheless.

Even in the last few moments before achieving a sustainable business, entrepreneurs will have setbacks. But, with a good support network, the well-deserved victory is achievable.

Love, Patience. Kindness. Defiance. Confidence. Endurance. Friendship. Joy. Learning. Shift gears and move forward. Both century cycling and entrepreneurship will push you out of your comfort zone and both will help you grow. Engage others willing participants in your endeavor and success is never guaranteed but becomes a more realistic expectation.