St. Ignatius College Prep Recognizes Chesley Taft Partner Greg O’Leary for Business Achievement – Five Maxims That Shaped His Success

We are proud to share that on November 13, 2025, St. Ignatius College Prep—one of the most respected preparatory schools in the nation—honored Chesley Taft Partner Greg O’Leary with its Alumni Award for Excellence in Business. This recognition reflects not only Greg’s professional accomplishments but also the integrity and leadership he has demonstrated throughout his career. 

During his acceptance speech, Greg shared five business maxims that have guided his approach to leadership, decision-making, and relationship-building over the years. At Chesley Taft, we fully subscribe to these ideals and thought we would share them with you.

Business Maxims – Greg O’Leary, Chesley Taft & Associates

1.      When you least expect it, expect it. Take nothing for granted.

2.      Do the right thing, the right way. It is difficult to do and usually requires more work—but it is well worth it.

3.      Excellence in business is 5% luck, 15% brains, and 80% hard work. I have never met a successful person who does not work long and hard. There are simply no shortcuts to excellence.

4.      When in doubt, check it out. A useful way to avoid trouble before it presents itself.

5.      If it’s too good to be true, it’s too good to be true. No free lunch; everything has a cost.

Greg’s achievements—and the principles he shared—reflect the foundation on which Chesley Taft was built: character, clarity of purpose, and genuine care for the people who place their trust in us. We are honored to celebrate Greg and grateful to share his maxims with you, which continue to guide our work on behalf of our clients.

*This award was granted independently by the portfolio manager’s alma mater and is unrelated to investment advisory services or portfolio performance. No compensation was provided. Past recognition does not guarantee future results.