Lessons Learned from Building a Company

October 2020

women elbow bumping

Image: Getty Images

Last week I wrote a piece on LinkedIn about the seismic changes in cybersecurity since I hitched my journalism wagon to that field 20 years ago.

I talked about what constituted a “content producer” back then. I noted how easy it was to break into the industry as both a practitioner and paid observer. And I discussed some of my most amusing moments to illustrate how far we’ve come as professionals.

What I didn’t delve deeply into was the relationship I formed with one of those early media leaders. That would be my current business partner, Maureen Joyce.

Call me shallow, but the first thing that impressed me about Maureen when I started at Information Security magazine wasn’t that she’d co-founded a successful magazine. It was that she had this awesome office space with a huge, inviting couch and funky office art. I didn’t spend nearly as much time as I wanted talking to her and her small creative team. But it was enough so that when the magazine was acquired and moved offices, with me already moving to the West Coast, I made sure to spend time with Maureen whenever I visited our new employer’s headquarters in Needham.

Years passed and we both moved on. Then a little more than seven years ago Maureen approached me with a business proposition: to help launch a custom content company that specialized in technology clients. She already had a name and a tagline and a branding concept, and that’s how Twirling Tiger Press, Inc. was born in September 2013. We later rebranded as Twirling Tiger Media to better reflect our content marketing services after repeatedly being mistaken for a printing company.

Many startups never make it to this age, so I thought I’d hypothesize why we have. Perhaps these tips will help other small companies live long and prosper.

Share the same vision, but not the same skills

Many startups arise from ideas for a great solution without really considering how that solution fits into the big picture. That’s why a vision statement is so important—one that’s universally adopted and periodically reevaluated. It’s just as important that each leader bring different strengths and weaknesses that complement, rather than compete. Maureen is a visionary. I’m an implementer. She dreams big; I’m more pragmatic. She manages her creative teams differently than I do our stable of writers and editors. It works, even if our work styles (even work hours) are dissimilar.

Bring in an outsider

One of the best things we did early in our early tenure was hire Victoria Cabot of Velocity6 to coach us in the Entrepreneurial Operating System®. This framework allowed us to chart both ambitious goals that hued to Maureen’s personality and establish practical steps that wove well with mine. When you are deep in the weeds, you can easily veer in different directions with target clients, sales goals, marketing campaigns, and so on. Leaders dead-set on one role may resist moving into another now required. And problems may fester until they alter corporate culture and talent flees. We also were fortunate to have had mentorships with Blue Cross Blue Shield of Massachusetts and the Small Business Administration’s SCORE program. Having an outsider that understands company dynamics and facilitates candid conversations is invaluable.

Plan for the inevitable

Our attorney advised us to plan for the divorce as soon as we married, because once the honeymoon wears off you’ll be glad to have such an exit strategy in place. We were so busy building the company, hunting for new clients and creating exceptional content for existing ones that we pushed this off for years. And then we discovered we had different ideas for what “the end” looked like. It created friction that would have been avoidable if we’d followed that lawyer’s advice. So, know going in how to handle when (a) a partner passes away; (b) a partner leaves; or (c) both partners part ways and shut down the company.

‘Give’ where needed

When you are a woman-owned business you are going to have family issues that require immediate attention and a temporary shift in priorities. Maureen and I both lost our mothers early in the company’s formation, when it was difficult to set aside work without a mature HR infrastructure in place. I then had to handle unanticipated issues upon my father’s passing. Maureen is about to embark on another major life change as she sells her current home of 30 years and awaits the buildout of a new one. Having moved many, many times myself, I know how disruptive a relocation can be under the best circumstances, so I also know to provide my business partner more breathing room on projects—even if she claims otherwise.

There are more lessons, but these four can provide much-needed buoyancy when you or your company appear to be drowning. No relationship runs smoothly long term, and that includes business relationships. Heed my advice, and without delay. You may not have a greater opportunity to do so than you do right now.

Be well,