Newsletters

Structural Motivation

August 30, 2026

The Concept Structural motivation is about timing, not morality. It’s about what the system rewards immediately versus what it rewards eventually. Humans don’t optimize for “someday.” We optimize for “this feels good right now.” If the system gives instant pleasure for the wrong behavior and delayed benefits for the right one, willpower will lose every

Read More

2 Questions That Kill the ‘Email Goblin’ in Your Law Firm

August 30, 2026

What do Back to the Future, a law firm intake team drowning in leads, and the time I tried to “just work harder” have in common? None of them work without systems, focus and maybe even 1.21 gigawatts… Here’s my favorite thought experiment to figure out how to build systems and focus. Ask yourself the

Read More

When “The Plan” Stops Working

August 30, 2026

What do Ferris Bueller, Thomas Edison, and me staring at the scale like it just filed a motion to dismiss my happiness have in common? They all hit the same moment: the thing worked… until it didn’t. Ferris could charm his way through one more “sick day” until the principal basically went full Terminator. Edison

Read More

The Best Resume Can Be The Worst Hire

August 30, 2026

What do Warren Buffett, Captain America, and that employee I hired because they had an incredible resume, w ho was gone six months later, have in common? It’s not that all three prove skills don’t matter. They absolutely do matter. But it’s that character beats experience every single time. Let me be very clear. I

Read More

5 CEO Moves To Get Out of the Weeds

August 30, 2026

What do Michael Jordan , Michael Scott , and Jordan MICHAEL Ostroff in 2016 have in common? It’s not the Michael thing…and it’s not that all three are allergic to delegating. (Although two of us definitely were. And it’s not the guy with six rings…) Instead, it’s about getting out of the day-to-day and into

Read More

Org Charts

August 30, 2026

What do Nick Fury’s Avengers Initiative, a law firm where every decision has to run through the managing partner, and my old bullseye org chart have in common? They all look like leadership… but they quietly train everyone to wait for the hero (or want to be hero) to show up. The Avengers only thrive

Read More

Virtual Assistants and the Future of Legal Operations

February 13, 2026

A few months ago, I got into an argument with someone who said that firms needed to bring everyone back to the office. They had secret numbers they could not share about efficiency and such. And yes, you certainly can do that, but you do not have to. How do I know that? Because I

Read More

7 Ways To Decide “What Do I Charge This Client?”

February 13, 2026

You want to know what industry I think teaches me the most about my law firm? Feel free to take a guess. Ready for it? The restaurant industry, and here’s why. As much as we might want to be fancy, white-collar, ivory tower types, that’s not really where we sit. No one is going in

Read More

Telling Better Stories

February 13, 2026

What Do Steve Rogers, Steve Jobs, and I Have in Common? None of us ever won people over with data dumps. Captain America didn’t inspire anyone by reciting battle statistics. He led from the front with a great backstory and the iconic look. Steve Jobs didn’t launch the iPhone with a spreadsheet. He gave the

Read More

How My 75-Day Challenge Reinforced Business Growth Principles

February 13, 2026

It’s over, it’s over, it’s over! My 75Hard experience is over, and I want to go deep into it with you. To be honest, it confirmed everything I talk about when it comes to running a good firm. I took the same principles I share here, applied them to my health, and whoa, did it

Read More

Hit Me With Your

Best Spot!

I love being invited to events— especially when it involves the chance to help more people run a business they can be proud of while living a life that’s even better. Whether it’s your awesome podcast or the conference of the year, let’s chat about how I can help make it that much better.

Book Me To Speak

It’s Not Easy

Being Green.

And it’s not easy to build a successful business while maintaining a sense of control over your life, either. That’s why I’m here, to help you create the kind of life you will love to live. Yep, you can have your cake and eat it too. Who would want a cake they can’t eat? (even if I am more of a cookie/brownie type guy).

Book a Consultation