Upward Trajectory Fund: The Next Chapter
After selling my company and taking some time to travel, I realized something quickly: I’m not wired for a life of doing nothing. There is joy in wandering a new city with no schedule at all, but eventually I found myself wanting something more—meaningful work, done well, on my own terms, and woven into a full life rather than overtaking it. Upward Trajectory Fund grew out of the realization
A question I heard often after the exit was: “Are you going to start another software company?”
It’s a fair question. But after giving it real thought, I realized the answer was no.
As an operator and CEO—especially at a lean company—you often work with your head down. You’re in the thick of it: solving problems, closing gaps, hiring, building, rebuilding. And when something shifts, you pivot. The work can be meaningful, but it’s inherently myopic. You need that level of focus to build anything durable.
After years of operating, I wanted something different.
I wanted to remain nimble—able to look left and right, not just straight ahead. I wanted peripheral vision: the ability to notice an opportunity sitting quietly in a corner of the market, rather than being locked into the urgent demands of a single product or roadmap.
Starting With a Blank Page
So I sat down with a blank sheet of paper and asked myself:
What do I want the next chapter of my working life to look like?
I wanted meaningful, mentally stimulating work that required deep focus and continual learning. I wanted to spend time with thoughtful, intelligent people with good values. I wanted a very small team—simple, high-trust, calm. And I wanted the flexibility to work from Toronto—my home base right now—or from London, New York, Hong Kong, or anywhere else in the world if the opportunity presented itself.
Before starting Upward Trajectory Fund, I tried to imagine what that might look like. I enjoy travel — including time spent in places like San Sebastián - and I wanted to bake that sense of curiosity and exploration into the next chapter, without making it the point. Could I spend a week in London and do a few hours of deep, intentional work in the morning — without disrupting the people I work with or the quality of the work itself? Could the same be true in Hong Kong or New York? That thought experiment helped me reverse-engineer the kind of organization I wanted to build: nimble, calm, focused, and able to function no matter where I am.
The goal was never to work from every trip. Quite the opposite. The goal was to build a structure where work fits naturally into a full life—where some days mean focused work in Toronto, and other days simply mean a quiet morning of reading or thinking in another city before closing the laptop and being fully present.
Upward Trajectory Fund is the vessel that allows that rhythm to exist.
Not long after I began shaping the idea, I was speaking with a contact at the bank about what I envisioned. After listening for a while, he said, almost in passing:
“Andrew… this sounds like a vessel. A container for the next chapter of your life, not just your career.”
I didn’t have the language for it until he said it, but that was exactly right. The idea clicked into place. Upward Trajectory Fund wasn’t just an investment platform — it was a structure for how I wanted to work and live.
A Founder First
My background is in software. I built an enterprise software company and spent years learning how to scale something lean, durable, and operationally disciplined.
What I did not have was a background in investing or private equity. That changed during the sale of my company.
Over eight months, I met with private equity firms from around the world. To my surprise, those months ended up being some of the most intellectually enjoyable of my career. I learned how they think, how they evaluate durability, how they model businesses, and how they protect the downside.
Their approach resonated with me—disciplined, patient, grounded in fundamentals. It made more sense to me than chasing future possibilities.
That experience shaped the direction of the next chapter.
Why Private Equity Fit My Temperament
People sometimes assume that because I built a tech company, the natural next step would be venture capital (investing in tech startups). I understand the logic, but the truth is that I’m a fairly risk-averse entrepreneur. I like things with history, pattern recognition, and evidence behind them.
Early-stage venture capital invests in future potential. Private equity invests in demonstrated track records.
Neither is better or worse—they’re simply different disciplines. Private equity just happens to align with how I think and how I like to work.
I also find it quietly fascinating to come across a great business in an unexpected place—an organization with strong leadership, a healthy culture, and a real customer problem solved consistently. That kind of quiet excellence appeals to my curiosity far more than chasing the next big idea. It’s one of the reasons why I was originally drawn to starting and scaling up a software company that was more focused on vertical markets vs trying to be all things to everyone.
What Upward Trajectory Fund Is
Upward Trajectory Fund is an investment platform designed to thoughtfully invest capital into durable businesses over long periods of time, and to compound that capital in the most efficient and disciplined way possible.
But equally important, it is the architecture of the work I want to do:
mentally stimulating
deep, uninterrupted work
learning something new each day
a very small team of capable, values-aligned people
clarity over noise
and flexibility built into the design
We are a very small team—by design. The work is real, thoughtful, and ongoing. And as I considered what would keep me engaged and learning in the years ahead, private equity emerged naturally as the center of gravity: a discipline grounded in fundamentals, durability, and long-term thinking.
Two Phrases With Semantic Density
Two ideas sit quietly at the heart of Upward Trajectory Fund:
Ancora Imparo — “I am still learning.”
Festina Lente — “Make haste, slowly.”
They say a great deal with very few words.
Ancora Imparo is a reminder to stay curious and have humility. Festina Lente is a reminder to move with intention, not haste.
Together, they shape how I want to invest, work, and live.
A Culture Built Around People
My previous company specialized in strategic people management. Over the years, I learned how incentives shape behavior, how cultures are built, and how fulfillment affects performance and retention.
Those lessons carried forward.
Upward Trajectory Fund is built around people who value judgment, curiosity, humility, and thoughtful pacing. A place where decisions are made carefully rather than quickly, and where quality matters more than quantity.
It’s the kind of environment where good decisions compound.
Compounding Excellence
“Compounding Excellence” isn’t a slogan. It’s the organizing idea behind the Fund.
I wanted a structure where improvement happens slowly and steadily—through better thinking, better habits, better relationships, and better choices.
Upward Trajectory Fund is the place where that can happen, professionally and personally.
A Life That Doesn't End With Work
I don’t believe in retirement. I believe in staying engaged, curious, and connected.
A meaningful life, to me, is one where work matters, learning continues, and there is space for travel, culture, and exploration—supported by a structure that lifts the years ahead rather than constraining them.
Upward Trajectory Fund is the vessel for that kind of life—a way to compound with purpose.
This is where the next chapter begins.
For more articles about my entrepreneurship journey or about life in general, visit my writing page.