Hello again, lovey humans,

Most people collect career titles. Michael Saitow collects first principles. This is his story.

The Early Lesson

Before Michael was a CIO, he was a freestyle skier and a ski coach. He worked with youth athletes and elite competitors, including Olympic-level talent. Those years on the mountain taught him something that would outlast every job title that followed: success is less about raw ability and more about preparation, attitude, and knowing how to laugh when things go sideways.

That lesson followed him everywhere. It followed him into emergency medicine. Into endurance sports too. Michael has spent twenty five years on the trails doing ultramarathons, mountaineering, long backcountry treks. And a year-long backpacking trip, he walked into a fifth-generation, family-owned beverage company called MS Walker. And he stayed for over two decades.

Building the Machine That Builds the Machine

When Michael joined MS Walker full time, the company had roughly 100 employees and $80 million in revenue. By the time his chapter there reached its final pages, it had grown to over 675 people and more than $550 million — through organic growth and nearly a dozen acquisitions.

If you meet Michael, you can see immediately that he's not interested in trendy, he's all about the first principles. Just as his skiing and trekking had taught him, preparation and building strong foundations are key. As with all the great wisdom traditions, establishing the physical and mental discipline ultimately leads to liberation from suffering

It wasn't about trends. It was about survival, clarity, and designing from the ground up.

Peeling the Onion

What we notice when interviewing a lot of accomplished operators, is that they are less interested in what they know, and more interested in what they assume. Recognizing that there is distance between what he knows and what he needs to still learn helps Michael stay grounded. As Michael says, "You keep peeling the onion when you'd rather stop." It's the discipline to test the known and the assumed. To stay curious enough to keep looking when the answers don't come easy.

That same mindset fuels his endurance life. Ultramarathons and alpine expeditions aren't hobbies for Michael. They're the physical expression of the same principle: keep learning, keep going when the comfortable thing would be to stop, and keep looking for the fun in everything. When you meet Michael, you immediately recognize that playful curiosity.

If you've ever spent time around endurance athletes, you'll know there's a particular quality they share with the best founders and technologists. It's not toughness, it's something closer to a tolerance for discomfort combined with an unreasonable belief that there's always another way to see the problem. Michael has that quality in abundance.

Why Michael Is a Second Harvester

Michael's story isn't the dramatic twist or the burnout we've shared before. There's no single moment where everything shattered. His is the second harvest that unfolds steps by step, like his marathon running. It's the story of someone who has spent decades showing up, peeling back layers, and refusing to let comfort become the ceiling.

From the outside, the resume might look like a winding road: athlete, medic, technologist, entrepreneur, advisor. But Michael now sees his life pulled by one thread. That thread is his discipline to start from first principles every single time, even when the shortcut is right there.

That's the thing about the second half. It doesn't always announce itself with a crisis. Sometimes it arrives as a recognition that the skills you've been building your whole life were never about the job. They were about you.

Michael realized, like many of us do, that he didn't need to find something new. He needed to recognize that the thread connecting everything together.

You can find Michael on LinkedIn at linkedin.com/in/michael-saitow.

More stories like this soon.

— Richard & Devon