Live outside
the box.
Dear Business Builder, Friend, Human,
Somewhere along the way, we were told we’d have to choose.
Build something big or live well.
Be ambitious or be present.
Success or joy.
Pick one. Pay the price. They call it "growing up."
I don’t buy that.
And I’m not interested in pretending I do.
My mission is to explore and enable a way of living and building where health, wealth, freedom, depth, adventure, and relationships compound together rather than compete. I don’t believe extraordinary outcomes require burnout, broken relationships, or putting real life on layaway until “retirement.”
That story is convenient.
It gives us an excuse not to follow our dreams.
It just isn’t true.
Through the companies I partner with and the rooms I help create, my work is about removing false tradeoffs between ambition and presence, success and joy, ownership and freedom. I work with people who want to build meaningful things without hollowing themselves out in the process.
I’m designing my life as a case study of what becomes possible when you stop optimizing for appearances and start optimizing for what actually matters. Not dropping out of the world. Just refusing to play games that make it smaller.
I grew up in a family of high achievers.
Attorneys. Accountants. Doctors. Educators.
The whole thing.
And then there’s me: the first person in generations without a degree. Not as rebellion. Not as regret. Just reality.
I’ve always been wired differently. I could lock in completely on what energized me and hit a wall on what didn’t. I questioned rules by instinct and struggled with anything that felt empty, performative, or divorced from real impact. That tension never went away. It just became a compass.
I started building early. I launched my first business in college (before I dropped out), found my way into property management, and eventually into private equity real estate. By my early twenties, I’d helped acquire and manage more than a dozen top-performing assets in a $1B+ portfolio. Next thing I knew, I was managing 100+ rental units and a multi-million-dollar budget entirely on my own.
No staff.
No safety net.
No one coming to save me.
When the corporate path I was promised quietly disappeared (in the midst of COVID), I walked away and started over in Atlanta; a city where I didn’t know anyone. It wasn’t glamorous. It was disorienting. And it forced me to get honest about what kind of work, and life, I was actually building toward.
That reset eventually led to building a business with my wife. What started as her college capstone project became a restaurant marketing company that has served over one hundred restaurants with a small, distributed team. But the most meaningful outcome isn’t revenue or growth.
It’s that we earned our freedom.
Since starting the business, we’ve spent over 100 days a year traveling and with family. Our life comes first. The business exists to support that, not the other way around. Somewhere along the way, I also realized I had fallen into a role I didn’t yet have a label for: stepping in at key moments, asking better questions, shaping strategy, and simplifying systems.
Then, we made another decision that clarified everything.
We moved to Bend, Oregon.
Not because it’s a “hot market.” Not because it optimizes for networking density or upside optionality. We moved because ski culture beats hustle culture. Because fresh mountain air matters more than whatever opportunities we might be missing in a bigger city. Because mornings that start outside make everything else work better.
Today, I work with people who share my values and have ideas I believe in, helping them redesign the game they’re playing before they scale something that owns them. My work lives in decisions, structure, incentives, and focus.
I’m not interested in doing more for the sake of doing more. I care about leverage, sustainability, and building businesses that actually make life better for every stakeholder.
I’m building a body of work, and a life, that compounds across the dimensions that matter most. If this way of thinking resonates, we’ll probably get along just fine.
Sincerely,
Thomas
Dear Builder, Friend, Human,
Somewhere along the way, we were told we’d have to choose.
Build something big or live well.
Be ambitious or be present.
Success or joy.
Pick one. Pay the price. They call it "growing up."
I don’t buy that.
And I’m not interested in pretending I do.
My mission is to explore and enable a way of living and building where health, wealth, freedom, depth, adventure, and relationships compound together rather than compete. I don’t believe extraordinary outcomes require burnout, broken relationships, or putting real life on layaway until “retirement.”
That story is convenient.
It gives us an excuse not to follow our dreams.
It just isn’t true.
Through the companies I partner with and the rooms I help create, my work is about removing false tradeoffs between ambition and presence, success and joy, ownership and freedom. I work with people who want to build meaningful things without hollowing themselves out in the process.
I’m designing my life as a case study of what becomes possible when you stop optimizing for appearances and start optimizing for what actually matters. Not dropping out of the world. Just refusing to play games that make it smaller.
I grew up in a family of high achievers.
Attorneys. Accountants. Doctors. Educators.
The whole thing.
And then there’s me: the first person without a degree in three generations. Not as rebellion. Not as regret. Just reality.
I’ve always been wired differently. I could lock in completely on what energized me and hit a wall on what didn’t. I questioned rules by instinct and struggled with anything that felt empty, performative, or divorced from real impact. That tension never went away. It just became a compass.
I started building early. I launched my first business in college (before I dropped out), found my way into property management, and eventually into private equity real estate. By my early twenties, I’d helped acquire and manage more than a dozen top-performing assets in a $1B+ portfolio. Next thing I knew, I was managing 100+ rental units and a multi-million-dollar budget entirely on my own.
No staff.
No safety net.
No one coming to save me.
When the corporate path I was promised quietly disappeared (in the midst of COVID), I walked away and started over in Atlanta; a city where I didn’t know anyone. It wasn’t glamorous. It was disorienting. And it forced me to get honest about what kind of work, and life, I was actually building toward.
That reset eventually led to building a business with my wife. What started as her college capstone project became a restaurant marketing company that has served over one hundred restaurants with a small, distributed team. But the most meaningful outcome isn’t revenue or growth.
It’s that we earned our freedom.
Since starting the business, we’ve spent over 100 days a year traveling and with family. Our life comes first. The business exists to support that, not the other way around. Somewhere along the way, I also realized I had fallen into a role I didn’t yet have a label for: stepping in at key moments, asking better questions, shaping strategy, and simplifying systems.
Then, we made another decision that clarified everything.
We moved to Bend, Oregon.
Not because it’s a “hot market.” Not because it optimizes for networking density or upside optionality. We moved because ski culture beats hustle culture. Because fresh mountain air matters more than whatever opportunities we might be missing in a bigger city. Because mornings that start outside make everything else work better.
Today, I work with people who share my values and have ideas I believe in, helping them redesign the game they’re playing before they scale something that owns them. My work lives in decisions, structure, incentives, and focus.
I’m not interested in doing more for the sake of doing more. I care about leverage, sustainability, and building businesses that actually make life better for every stakeholder.
I’m building a body of work, and a life, that compounds across the dimensions that matter most. If this way of thinking resonates, we’ll probably get along just fine.
Sincerely,
Thomas
