Over the course of my more than 15 years as a CTO, I’ve learned many technical lessons. But the lesson that has mattered the most, and has had the greatest impact on the teams I’ve led, is this: strong teams are built by strong managers leaders.
That idea didn’t come from the world of tech alone. My approach to leadership has been shaped largely by four major sections of my life:
- Leading in business as a CTO and Founder
- Decades of coaching and training in martial arts
- Serving as a leader in the military, including in combat
- 4+ years as a volunteer fireman
Each of those environments is wildly different. But despite the differences in stakes, intensity, and context, one truth has always remained the same: people perform their best when they are supported, challenged, clearly guided, and given the space to grow.
And that becomes possible only when the right environment is present. The right environment shaped by strong leadership.
A Brief Series Origin Story
A few years ago, I started recording internal training sessions for the teams I was working with. These weren’t meant to be polished productions. They were practical conversations about the real work of managing people: setting expectations, communicating clearly, giving feedback, and developing your own leadership style.
I created them because I found myself repeating the same lessons to new managers, senior leaders, and even peers. So I turned those lessons into a series of straightforward, actionable sessions that could be reused, shared, and built upon.
Over time, the collection grew. And as I continued using them, talking about them, and sharing the ideas, I realized something: Everyone could benefit from this information.
Why Now
Leadership is often learned on the job; trial by fire. Most people become managers because they’re good at their job — not because they’ve been trained to lead. And while companies talk a lot about “developing managers,” they often invest very little in actually doing it. Many decent managers become that way by saying, “I don’t want to do what X shitty boss did” and then doubling down on that. While this sometimes works, it can be fairly limited as it’s typically rooted in fear. I want to democratize this information. So I’m opening up these trainings for anyone who might benefit from them.
My goal is simple: If even one person improves because of these videos, then sharing them is worth it.
The First Three Videos
To start, I’m releasing the first 3 videos that I recorded. There are all between 30 and 60 minutes long.
There isn’t actually any order that everything should be viewed in. Each session can stand on its own. But there are at least 20+ more videos that I’ve already recorded over the last few years that are coming as soon as they edited. They’ll all appear on the YouTube Playlist when they are ready.
Who These Trainings Are For
This series is for:
- New managers stepping into leadership for the first time
- Experienced managers who want to sharpen their approach
- Leaders who want to build healthier, more effective teams
- Anyone curious about developing their own leadership style
I’ve spent much of my adult life leading and coaching people in one form or another, whether in high-pressure environments or in day-to-day team settings. These videos are an attempt to pass along the practical, real-world lessons that have consistently helped people grow.
Closing Thoughts
You don’t become a better manager by accident. You become one intentionally, through learning, self-reflection, and practice. If these sessions help you build stronger relationships, set clearer expectations, or lead with more confidence, then this project has done exactly what I hoped it would. I’m not perfect, and I don’t have all the answers. These lessons were learned, unfortunately for me and many who worked for me, through a lot of trial and error. But with a little bit of progress all the time, I hope that you can avoid some of the same mistakes that I’ve made over the years.
Thanks for reading, and I hope you find the series useful.
Check out the People Manager Trainings page for all the videos or check out the YouTube Playlist.
