(Picture: Paddling in sea kayaks in Sydney, Australia)

Strategy 4 Saturday Blog (<4 minute read)

Thanksgiving, five years ago, marked a turning point in my life. A decision loomed, and it was anything but easy.

Crossroads 

I found myself at a crossroads. Should I accept an exciting opportunity at a strategic planning software firm to spin off and lead their global consulting firm? This offer came directly from the founder, as we paddled in sea kayaks in Sydney, Australia. Our company had earned its reputation as the #1 software for strategy execution, but we uncovered a critical insight: while the software was excellent for tracking execution, its true power depended on the quality of the strategic plan itself. Without the right plan, the tool wasn’t fully utilized.

Over three years, our US office achieved remarkable growth, expanding our enterprise clients twentyfold. As our sales and support teams thrived, I began facilitating strategic planning sessions across the US and the Caribbean. The work was impactful, and I loved it. Now, I had the chance to take this mission global, serving thousands of clients.

But there was a tradeoff. I had four kids deeply involved in sports—three would go on to play collegiately. Global travel would mean missing a significant chapter of their lives.

What If? 

Then a new idea emerged: what if I ventured out on my own? What if I started a consulting firm dedicated to helping clients design effective strategic plans and execute them with purpose?

From my wife’s perspective, the idea of another startup was daunting. No clients. No steady income. Four kids to support through college. Yet deep down, with faith and conviction, I knew it was the right decision.

And so, 40 Strategy was born.

The name came from a startling statistic: most companies spend only 2% of their time on strategy—that’s just 40 hours a year per person. 40 Strategy exists to change that, providing expertise and guidance to help organizations focus on strategy more effectively.

Now, five years later, we’ve beaten the entrepreneurial odds. 40 Strategy continues to thrive, facilitating strategic planning processes and keeping our clients accountable. But the journey has been filled with unexpected twists and lessons starting with our launch in January 2020:

  • COVID.
  • A burst appendix.
  • Partnering with private equity firms.
  • Leading company turnarounds.
  • Growing clients’ revenues and profits.
  • Maximizing business cash balances.
  • Improving business owner confidence.
  • Launched a podcast.
  • Writing a book, Lost at CEO.
  • Running a marathon.
  • Starting a 2nd podcast.
  • Building meaningful partnerships.
  • Developing great relationships.
  • A double hernia surgery.
  • Seeing my kids compete in sports across the country.
  • Opening my 2nd CPA firm under the name 40 Accounting.

It hasn’t been easy, but it’s been immensely rewarding.

This Thanksgiving, I’m profoundly grateful for the past five years. Thank you to my family, friends, staff, clients, and partners who have supported this journey.

Here’s to the next five years—making a difference.

Happy Thanksgiving to you and your family!

PS – Five years ago, my son Tyler made a major decision to pursue his education at the US Naval Academy. Last weekend, we watched our son Tyler play in his last college sprint football game at West Point. It was a bittersweet moment but so grateful to have the opportunity to watch him play four more years. On Thursday, we learned that he has been appointed to be a Navy Pilot after he graduates. Congratulations, Tyler, we are proud of you!

(Picture: Sarah & I, with our Navy Pilot, Tyler)

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