Signals I Pay Attention To

On a clear night, the stars matter because there is darkness around them. If the sky were packed edge to edge with light, no single star would register. It would be bright, but meaningless. What makes the stars visible is not their abundance, but the space that holds them.

I’ve come to notice something similar with signals. Signals don’t amplify through addition. They emerge through subtraction. Clarity rarely arrives by adding more - more information, more opinion, more activity. It arrives when enough noise is removed for something to separate itself. What remains after subtraction is usually the signal.

What follows are some of the signals I’ve come to notice and pay attention to over time. Not rules or advice—just patterns that tend to emerge once the background clears.

Energy

Of all the signals I pay attention to now, energy is the most important.

In the heat of an interaction or a decision, I still find it easy to get caught up in facts - pros and cons, logic, timing, surface appeal. But over time, I’ve learned that those details are rarely decisive. The signal that matters most comes afterward.

Every interaction, opportunity, or decision leaves a residue. It either adds energy or it takes it away. There’s no neutral. The effect may be subtle, but it’s always there. Do I feel more awake, or slightly depleted? More energized or less energized?

I don’t try to assess this in the moment. I notice it later, often without commentary. That after-effect has proven more reliable than whatever rationale I could assemble at the time. So the primary signal I pay attention to now is energy - not intensity or excitement, but the net balance it leaves behind.

Urgency

Another signal I pay attention to is urgency - not as a fact, but as a form of communication.

I’ve noticed that when someone pressures me to make a decision within twenty-four hours, my interest usually drops rather than rises. I often find myself quietly amused when that same offer resurfaces a couple of days later, still very much available. By then, whatever urgency existed has evaporated entirely.

I don’t find it offensive or alarming, just informative. When everything is marked urgent, nothing actually is. The mailbox fills with envelopes stamped “urgent,” and they cancel each other out.

A friend of mine has a simple rule: he only responds to the second email someone sends. Not out of indifference, but as a filter. If something is truly urgent, it tends to resurface on its own.

Taste

One place I notice signal very clearly is taste, something I’ve written about before as I ate my way through San Sebastian. I’ve always loved espresso and cacao. What draws me to both is that they are already complete, just as they are. The flavour is fully formed in the bean itself - shaped by air, altitude, humidity, soil and time. Nothing needs to be added.

For that reason, flavored coffee or flavored cacao has never held much appeal for me. It feels like diffusion - something layered on top of a signal that was already pure. When the base is strong, additional flavor doesn’t clarify it. It blurs it.

Competence

Another signal I pay close attention to is competence on a topic. I consider myself an autodidact. I learn most things on my own, and over time I’ve noticed that the fastest way to understand a new subject is to look for signals of competence and influence.

Today, there’s very little friction to expressing an opinion. Anyone can publish a post, a tweet, or a thread. Volume is cheap. What’s harder to fake is influence on other thoughtful people.

When I want to understand a field, I pay attention to who everyone else is quoting. Not who’s loudest—but who keeps appearing across independent sources. In artificial intelligence, for example, you can read thousands of takes. Or you can notice that conversations keep circling back to neural networks and to Geoffrey Hinton. That repetition isn’t accidental.

A simple trick I once read—and still use—is this: take any three books on a subject, flip to the bibliography, and see which names appear most often across all of them. That person is usually the signal. I start there.

Bubbles

I’ve also come to find the structure of bubbles fascinating. Not prices, but signals. There’s no better place to see this than in meme stocks.

What happened with the GameStop stock in 2021 and later dramatized in the film Dumb Money (it was no foreign film but was still excellent) wasn’t just a market event. It was a memetic one. Ideas spreading faster than understanding. Signals amplifying each other.

I notice a familar pattern. When the cleaning lady mentions a stock in passing, a bubble is beginning to form. When the cashier at the grocery store checkout casually mentions the same stock, a bubble in full swing. When the cleaning lady, the cashier and the Uber driver are all talking about the same stock, its only a matter of time before the bubble bursts.

Music

A final signal I love is music.

Silence can be described as auditory perfection. Every note, musical phrase, or piece is competing with silence—and silence is a very high bar. Most don’t clear it.

Most people can name a song or a piece that didn’t resonate with them. It wasn’t offensive. It simply wasn’t better than silence. Only what earns that interruption is worth listening to.

The same is true with writing. An empty page is perfect. Every word competes with it. Most don’t win.

I’ll stop here.

There are more articles about my various experiences on my writing page.

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.

How We Doubled a Software Company in the Two Years Before Exit

Many people have asked how to prepare a software company for an eventual exit, what the process looks like end-to-end, and what it takes to double a business over a two-year period while maintaining profitability. I’ve heard these questions from founders, operators, private equity professionals, and friends, so I thought I’d share the experience as it actually unfolded.

If there’s a useful insight here for someone building or scaling a software company, then writing this will have been worthwhile.

This isn’t a playbook or a formula. It’s simply what happened — a two-year journey from a strong foundation to doubling the company while staying profitable. Let’s begin.

A Quiet Question at the End of 2019

At the end of 2019, I was enjoying running the company. I wasn’t looking to step away, but I began thinking more seriously about optionality. A simple question surfaced:

Do I want to run this company indefinitely, or might I one day want to sell?

I wasn’t sure of the answer yet. But I did know one thing: if I were ever going to sell, I didn’t want to sell at a plateau. I wanted the company to be operating at its best.

At the time, we were an enterprise software company that had not taken on venture capital, private equity, or debt. This meant that by necessity we had to be extremely capital-efficient.

We served professional services firms — accounting, consulting, and especially large law firms. We had over a thousand enterprise deployments and a strong presence among large law firms globally. Top-line growth was in the 15–20% range, and EBITDA margins were in the mid-60% range. The company was healthy. Nothing was broken.

We were well regarded and trusted by our customers. Over the years, private equity firms and strategic buyers reached out periodically. I never returned those calls — I was focused on building the business.

But I told myself that if I ever did decide to explore a sale, I wanted the company to be in the best possible position.

That led to a private and ambitious goal: double the company’s topline revenue over two years while maintaining profitability.

To understand why this was challenging, it helps to look at the Rule of 40 — a common software benchmark where a company’s growth rate plus profit margin should equal 40. For example, 20% growth and 20% profitability would meet that standard.

At the time, we were already operating well above that threshold. The goal was to push much further — toward a profile that combined roughly 40% growth with mid-60% EBITDA margins.

It was an aggressive target, but one I felt was worth pursuing.

The Conference in December 2019

A few weeks later, I flew to a conference. Travel always gives me clarity — I step out of my routine, and the noise falls away. Travelling is actually one of my favorite ways to solve a strategy problem or any challenge for that matter. One afternoon, I took a notebook into a quiet conference room at the hotel and closed the door.

Over the course of a few hours, a clear strategy began to take shape.

Only later did I realize that what I had written closely resembled a private-equity style growth plan. I wasn’t trying to emulate one. The approach simply emerged from focusing on the most effective growth levers available, using only what the business already had and without taking on outside capital or debt. That constraint forced discipline, efficiency, and focus.

Below are the six steps that ultimately helped us double the company while staying profitable.

1. The Wave Platform — Our Keystone

Our user interface was solid and functional, and it had served us well. As the product suite matured, it became clear that a more cohesive and modern UI/UX would help modernize the look and feel of the software and tie the entire platform together. At the time, we had six products, all built on a single enterprise software foundation.

Around this period, Salesforce released Salesforce Lightning. We used Salesforce extensively for customer relationship management, sales operations, and customer care, so I paid close attention. Lightning introduced a new user experience. The most interesting part wasn’t the interface itself — it was the strategy behind it.

If you wanted access to Salesforce’s newer modules, you had to adopt Lightning across the board. Once you did, everything else followed.

That approach stood out to me.

Steve Jobs once said:

“Good artists copy; great artists steal.”

I don’t believe in stealing, but I do believe in borrowing strong ideas and adapting them thoughtfully. We decided to create our own version of that approach — a single, unifying initiative that could anchor the rest of the strategy and give the product suite a shared identity following the redesign.

I spent some time thinking about what to call it, until one name felt right:

Wave.

The Wave Platform.

It felt clean, energetic, and symbolic — like momentum moving through the organization and across the product line.

We hired UI/UX designers, re-skinned every module, and rebuilt the user experience from the ground up. The legacy interface became “Classic.” Everything new would live on Wave.

Wave became the user experience reset the company needed, and it provided a clear foundation for the initiatives that followed.

2. Build the Seventh Product (Resource Allocation)

We had six enterprise modules in our strategic people-management suite. As part of the broader growth plan, we decided to add a seventh. One of the advantages of vertical market software is that it’s often easier to introduce additional products within the same vertical than to take a new product across many different markets.

Before deciding what that product should be, I spent time speaking with customers about their most pressing operational challenges. The same theme came up repeatedly.

Resource allocation — staffing the right people on the right projects at the right time. For professional services firms, this is the core of the business: assembling teams to do billable work efficiently and predictably.

This was before the COVID pandemic.

Resource allocation emerged as a clear opportunity, and we chose to build the new product natively on the Wave platform. In retrospect, the timing proved to be significant.

Shortly after we launched internally, COVID hit. Large law firms with hundreds or thousands of professionals suddenly shifted to fully remote work. Staffing projects — already a complex task — became much more difficult.

The new product addressed a problem that had quickly become more acute, and customer interest increased accordingly.

3. Migrate Customers to the Cloud

Another pillar of the strategy was modernizing our delivery architecture.

We deepened our partnership with Microsoft and committed fully to Azure. Over time, we built a multi-location Azure deployment, introduced a cloud program with multi-year contracts, and transitioned customers — including legacy on-prem and subscription users — to the cloud.

This shift helped:

• improve performance and security

• simplify infrastructure

• increase reliability

• better align contracts with delivered value

• support the product roadmap ahead

It also created a more scalable commercial model, with the Wave platform delivered through our Azure cloud environment.

4. Update the Price Book

With Wave in place, a new product built, and cloud migration underway, it was the right moment to rebuild our pricing model from the ground up.

We introduced:

• new modular pricing

• new product packages and bundles

• cloud incentives

• a full-suite adoption model

A clean, disciplined commercial reset.

5. Charge for Implementations

Historically, implementations were bundled into our annual SaaS (Software as a Service) subscription fee. This made sense early on, but with growth accelerating, it was time for a change.

We shifted to charging implementation fees as a percentage of annual subscription value. This improved:

• margins

• delivery scoping

• customer outcomes

And it funded many of the new hires we needed for the growth plan.

6. Rebuild the Entire Go-To-Market Engine

To support the broader strategy, we strengthened every part of the go-to-market function:

• hired a senior marketing leader

• hired a demand generation manager

• built an outbound SDR (Sales Development Representatives) team

• upgraded sales talent

• redesigned the sales compensation plan

• implemented a modern GTM technology stack

• rebuilt the sales methodology

Together, the above six steps supported the goal of doubling the company’s revenue over a two-year period.

With these pieces in place, the organization was aligned around the Wave platform, the new product, and the cloud program.

Internal Alignment: Launching Wave Inside the Company

Before sharing The Wave Platform more broadly, we introduced it internally.

We held an all-hands meeting to walk through the direction of the company and the changes ahead. The team understood where we were going and what we were building toward. It marked the beginning of a multi-quarter, multi-year effort that would require patience, focus, and discipline.

It reminded me of the well-known marshmallow test: the work happens now, and the reward comes later. This phase of the journey was about delayed gratification and committing to a longer-term goal.

February–July 2020: Preparing to Execute the Strategy

As mentioned earlier, our financial year ended on July 31. That timing provided a natural lead-in before formally starting the initiative to double the company. There was a clear ramp-up period.

One of the first steps was a webinar for customers and prospects in February 2020, shortly before COVID. It was an opportunity to introduce Wave, along with the new product structure and bundles. Attendance was strong, and the timing proved fortunate — a month later, when COVID disrupted everything, it would have been much harder to convene that audience.

From February through July 2020, we focused on preparation internally:

• officially launching Wave with the new branding and transitioning prior products to “Classic”

• presenting the strategy to customers and prospects

• aligning engineering, sales, marketing, operations, and implementation

• completing technical work on Wave

• building the cloud program

• updating pricing

• strengthening the go-to-market engine

By the end of that period, the plan was in place, the organization was aligned, and we were ready to begin executing.

August 1, 2020 — Pedal to the Metal

Our financial year began on August 1, 2020, and this marked the point at which the two-year clock officially started.

The objective was clear: double the company’s revenue within two financial years, by July 31, 2022.

From that point forward, execution became the focus. Across the business, we saw steady progress in several areas:

• adoption of the Wave platform

• cloud migrations

• demand for the resource allocation product

• top-of-funnel pipeline

• contract value

• customer expansion

By July 31, 2021 — the end of the first year of the strategy — the core elements were in place and performing as expected. The company was growing, and momentum was beginning to build.

One lesson that became clear during this period was that growth of this kind is non-linear. There is inertia to overcome early on, followed by a phase where progress compounds more quickly.

The doubling trajectory was visible, but it required continued focus and consistent execution.

End of 2021 — To Sell or Not to Sell?

By the end of 2021, I was about a year and a half into the two-year strategy. The core elements were in place, and the plan was unfolding as intended.

To sell or not to sell — that was the question.

Toronto had reopened briefly for Christmas after an extended COVID lockdown. I remember returning to the gym during that short window. Shortly after New Year’s, the Omicron variant emerged and the city went into lockdown again.

I booked a one-way ticket to Miami. I needed warmth, running weather, and some distance to think clearly.

We were roughly three-quarters of the way through the doubling plan. The Wave platform was gaining traction, the new product was being adopted, customer retention remained strong, and sales performance was steady.

At the same time, software company valuations were particularly strong.

The timing felt aligned.

I returned the call to the investment bankers who had reached out over the years and said,

“Guys, it’s showtime.”

At that point, I decided to formally explore a sale of the company. We began working with the bankers on the preparation process, including historical performance, the product roadmap, and forward-looking plans. It was a rigorous exercise, and it offered a new perspective on the business I had been focused on building day to day.

The Final Six Months — Pressure and Precision

Once the sale-of-the-company process began, the pressure increased noticeably. Private equity firms and strategic acquirers were now reviewing performance closely. As mentioned earlier, doubling a business is rarely linear, and the final six months required sustained focus and execution to stay on track.

Performance was being monitored frequently, and there was little room for error. Customer retention and growth needed to remain steady throughout this period.

I found that pressure clarifying. It sharpened priorities across the organization and reinforced the importance of execution. The team responded well, and we continued to deliver quarter after quarter.

In the final two quarters of the year — ending April 30 and July 31 — the sales team met their targets very closely. I remember a meeting about two weeks before quarter-end where I used a Michael Jordan analogy. Jordan won his championships in Game 6 rather than pushing things to Game 7, viewing it as a way to reduce unnecessary risk.

We aimed to close the quarter early for the same reason, but that didn’t quite happen. Going into the final week, I remember saying, “We’re going to Game 7.” The team stayed focused, and the quarter came together in the end.

Hitting the Goal

By the end of the second year, on July 31, we had doubled the company’s revenue. The result was very close to the original target.

Top-line growth reached approximately 40%, while EBITDA margins remained in the mid-60% range. In practical terms, this put the business well above the Rule of 40 benchmark.

The outcome reflected the cumulative effect of a series of focused decisions over time. Progress compounded gradually, and the results aligned closely with the original goal.

The company was subsequently acquired by Roper Technologies, a long-term owner of mission-critical software businesses. Looking back, I’m comfortable with the decision and how the process unfolded.

A Team Effort

Although I’m the one writing this article, the outcome was very much a team effort. Across engineering, implementation, support, marketing, sales, product, and operations, people showed up consistently and did the work required to make the plan real.

What made the difference wasn’t individual heroics, but alignment around a shared goal.

Clarity Comes From Stillness

The entire two-year journey began in a quiet conference room with nothing but a notebook and a simple question:

Do I want to run this company indefinitely, or might I one day want to sell?

Looking back, the process of growth was as meaningful as the outcome itself. The work required patience, discipline, and sustained focus, and I found that journey deeply rewarding.

An added benefit was the clarity it brought. The path helped me think more clearly about what I wanted to do next, and the conversations that followed during the sale process naturally opened the door to the next chapter.

Sometimes the most important decisions begin in silence.

Visting my writing page for more articles on entrepreneurship but also on life too.

Three Days and Three Stars - San Sebastian

For as long as I can remember, I’ve enjoyed fine dining — not simply as places to eat, but as places where craft, imagination, and emotion come together on a plate. San Sebastián, Spain, is one of the few places in the world where this level of culinary artistry feels so concentrated. In the best kitchens, food becomes more than food. It becomes art: a form of expression, a creative language, a way for a chef to communicate a lifetime of passion in a single, fleeting moment.
Food, for me, has always been one of the most delicious forms of art.

Michelin stars aren’t merely awards; they’re acknowledgments of a creative mission in the world of fine dining. Chefs are bestowed Michelin stars — one for excellence, two for exceptional craft, and three for a level of artistry only a small handful of restaurants in the world ever reach. As of 2025, there are 157 restaurants globally with three Michelin stars.

San Sebastián, a small city on the northern tip of Spain, remarkably has three Michelin three-star restaurants, one of the highest concentrations of top-tier dining anywhere in the world. At some point, I realized I wanted to experience all three in a single trip — not as indulgence, but out of curiosity. What would it feel like to encounter three different expressions of culinary art on three consecutive nights?

So I planned it deliberately: three days, three nights, three Michelin stars — a short, intentional immersion into a world of culinary craft that exists in only a few places on earth.

San Sebastián felt like the right place for that kind of exploration. It’s a coastal city shaped by the ocean and framed by green hills, reminiscent of Florence in how the water meets the old town, just smaller. It’s only a four-and-a-half-hour train ride north of Madrid, yet it feels entirely different the moment you arrive.

This isn’t how I live day to day. Experiences like this make up a very small fraction of my year. But every so often, that one or two percent offers a chance to pause and reflect. I was coming off an intense chapter of focused work — one I’ve written about elsewhere — and wanted a change of pace that felt thoughtful rather than rushed.

A City Between Two Beaches

Two beaches give San Sebastián its geography and its personality. La Concha, an elegant, west-facing crescent, calm and classic. Zurriola, to the east, more open and energetic. The Old Town sits between them, compact and walkable.

A river separates the Old Town—narrow stone alleys, pintxo bars, and history—from Gros, a creative neighborhood of pastel homes and coffee shops. Crossing the bridge between the two reminded me of Florence: a city divided into distinct areas, architecturally unique.

The Basque people were warm and welcoming—proud of their culture, their food, and their unique language, Euskara. Traveling solo made those interactions feel more immediate and immersive.

A Balance of Routine and Freedom

I enjoy travel where I can keep parts of my routine while giving myself the freedom to explore fully. In San Sebastián, that meant staying at the Hotel Maria Cristina, a beautiful historic landmark, and beginning each morning with some form of movement.

When I travel solo, I tend to divide my day loosely into thirds. Mornings are for breakfast and a workout. Afternoons are for lunch and exploring on foot. Evenings are for dinner and, when possible, something cultural or local. It’s a simple structure, but it allows me to experience a city fully without losing the grounding elements of routine. It also makes frequent travel feel sustainable rather than disruptive.

In San Sebastián, the gym I joined for a few days was AltaFit Donostia, a modern, welcoming space with everything I needed. On the mornings I ran, I followed routes around Monte Urgull, looping along La Concha and weaving through the streets of the Old Town. It reminded me of running the Seawall around Stanley Park in Vancouver—just on a much smaller scale.

Exploring a city on foot — including through running — has gradually become one of my favorite ways to understand a place.

Afternoons were slower. I wandered the Old Town and spent time in cafés. Simona stood out—bright, relaxed, with good food and a view across the water. Dripper was more of a small espresso bar and the kind of atmosphere that invites an hour of reflection or planning.

It was an ideal rhythm: routine in the morning, exploration in the afternoon, and in the evening, meals that lingered. One night, before my first dinner, I walked along Zurriola and looked back toward the Old Town. The pastel buildings were catching the last light of the day, glowing softly. It was a simple moment, but one I still remember.

Basque Cuisine as Art

Basque cuisine is shaped by both the sea and the mountains: fresh fish, charcoal grilling, seasonal vegetables, and a respect for simple ingredients handled with care. The region has long been known for culinary innovation, which helps explain why so many influential chefs come from here.

I’m not a food expert, but I appreciate art — and in San Sebastián, art shows up in many forms.

One note before describing the dinners. There are many excellent food writers who document every course in detail. This isn’t meant to be that. The meals unfolded slowly over a few hours, but what stayed with me wasn’t any single dish. It was the pacing, the atmosphere, the warmth of the people, and the way each place expressed itself. What follows are impressions, not a catalog.

Three Evenings, Three Stars

A typical tasting menu lasts two and a half to three hours—unhurried, intentional, quietly immersive. All three restaurants sit just outside the city center, reached by short taxi rides into the wooded hills or along the coast. Each evening felt distinct, as if you were briefly stepping into a different world.

Night One: Akelarre

“Akelarre” comes from the Basque word for “witches’ sabbath,” a reference the restaurant leans into subtly. When the butter arrived, it was stamped with a small mythical creature—half human, half animal—pressed into the surface. It sounds simple, but it was among the best butter I’ve ever had, and an early signal of the care behind everything that followed.

The dining room is contemporary—wood, glass, open space—and intentionally quiet. The tasting menu, around a dozen courses, leaned gently toward the sea. One dish diners often remember is Akelarre’s playful, ocean-inspired creation, understated rather than showy.

Night 2: Arzak

Arzak is named after its founder, Juan Mari Arzak, one of the pioneers of modern Basque cuisine. Today, the restaurant is led by his daughter, Elena Arzak, who carries the legacy forward with her own voice and perspective.

The space feels like an intimate modern home—less wood, more warmth and history. Upstairs is their flavor and spice laboratory, with hundreds of ingredients, where combinations are tested like creative ideas in progress.

The menu, roughly ten courses, blends innovation with tradition. Dessert arrived looking like a small abstract sculpture—delicate, surprising, and memorable. I had the chance to meet Elena briefly; she was warm and focused, attentive to the dining room while ensuring everything moved with quiet precision.

Night 3: Martín Berasategui

The restaurant that bears his name is even more contemporary: wood, large windows, and an open concept designed not to distract. The room recedes so the plate can lead.

The pacing was steady and assured, each course arriving with quiet confidence. A layered eel dish—often mentioned by diners— was delicious. The atmosphere felt joyful but calm, as if the entire team was moving in sync.

When the food takes the lead

What struck me across all three restaurants was how little noise there was. I’ve noticed this pattern at the best restaurants I’ve been to: when the room steps back, the food steps forward. The result isn’t dramatic—it’s immersive. And it allows the food on the plate to speak for itself.

A City That Leaves a Mark

San Sebastián still carried the afterglow of its film festival, which takes place each September. I’ve always had a soft spot for film festivals, especially ones that celebrate foreign films—the kind that slow you down and ask you to pay attention. Between the walks, the cafés, the hills, and three very different dinners, the city revealed itself gradually—through small details, warm gestures, and the steady presence of the sea.

I was reminded of a line I once read in a critic’s review of Jiro Dreams of Sushi, the documentary about the three-star restaurant in Tokyo:
“The only tragedy is that Michelin does not—and never will—give out a fourth star.”

After three days and three stars in San Sebastián, I understood exactly what he meant.

There are more articles about my various experiences on my writing page.

Why I Love Vertical Market Software Companies

Why Vertical Market Software Matters

A few years before I was ready to sell my company, Roper Technologies’ Head of M&A called me directly. He said something I never forgot:

“Whenever you’re ready to go, give us a call.”

At the time, I didn’t fully grasp why one of the world’s most sophisticated acquirers of vertical market software—industry-specific, mission-critical systems—would reach out so early. Roper is an S&P 500 and NASDAQ-100 company known for buying deeply specialized software businesses and holding them forever. Their philosophy centers on customer intimacy, workflow depth, and long-term defensibility.

He explained that Roper had heard very positive things about our business—specifically our reputation, our focus on a single vertical, and the closeness of our customer relationships.

Years later, Roper ultimately acquired the vertical software company I operated. That experience shaped how I think about specialization, defensibility, and why vertical market software companies compound in ways horizontal companies often do not.

This article explains why.

Horizontal vs. Vertical Software: The Real Distinction

What is vertical market software, and how is it different from horizontal software?

A helpful way to understand the distinction is through marketing tools. Products like HubSpot or Marketo solve a functional problem — helping marketing leaders execute campaigns — and they work across nearly every industry. That makes them horizontal systems, designed to support a job function regardless of the business itself.

Vertical market software solves problems that only exist inside a specific industry. Examples include construction project management, dental practice scheduling, restaurant point-of-sale systems, logistics and dispatch platforms, law firm billing, and professional-services staffing and performance software. These systems are built around industry-specific workflows, regulations, and operating realities.

Horizontal software solves broad functions, often organized by job description — marketing software, accounting software, sales management software. Vertical software goes deep into a single industry and models how that industry actually works. That depth is what makes it vertical market software.

TAM vs. SAM: Why Vertical Markets Are Smaller, More Accessible, and Far More Winnable

Horizontal software companies enjoy massive TAMs (Total Addressable Markets) because nearly every medium to large organization has a sales leader (Salesforce), a marketing leader (HubSpot or Marketo), and an HR leader (Workday). But capturing these horizontal markets requires enormous capital, global distribution, and highly generalized products capable of satisfying thousands of edge cases across dozens of industries. Even the very best horizontal vendors often top out at owning 30–40% of their market.

Vertical software is fundamentally different. The TAM is smaller, but the Serviceable Addressable Market (SAM)—the portion of the market you can realistically reach—is often most of the TAM itself. Specialization becomes the advantage. You’re solving painful, industry-specific workflows that horizontal systems cannot serve well, and information travels quickly inside a vertical.

This creates a dynamic where a vertical software company can realistically dominate its market in a way horizontal vendors rarely can. In many industries, once you become the system used by the top firms, the rest of the market follows naturally.

In a horizontal market, it takes massive capital to capture even a small percentage of TAM.
In a vertical market, specialization becomes the force multiplier—and you can become the market.

That was my experience. When I operated a vertical software company, we were fortunate enough to reach well over 90% of the legal market segment we served—something that would be nearly impossible in a horizontal category. That level of penetration wasn’t achieved through massive marketing spend; it emerged from domain expertise, credibility, customer intimacy, and vertical word-of-mouth.

Vertical TAM may be smaller, but the cost to win it is dramatically lower. You don’t need to boil the ocean—you need to serve one industry better than anyone else.

And once the top players adopt your solution, the viral loop begins. People move between firms and bring the software with them. New managers ask for the systems they already know. Job descriptions begin to require experience with it. In a vertical, once a few leaders adopt your product, the rest of the market pays attention—and often follows.

When you own a vertical, you don’t just win customers. You become part of the operating fabric of the industry.

Multi-Product Expansion: The Most Underrated Advantage in Vertical Software

At one point, I attempted to expand into new industries. Even with a strong product, the cost of entering a new vertical was extraordinarily high. Every industry has its own vocabulary, compliance rules, internal politics, and buyer psychology. Repeating our success elsewhere would have required significant venture capital or debt financing—something I deliberately chose not to take on.

What did work—elegantly and reliably—was expanding inside the vertical we already understood.

The economic buyer already trusted us for our beachhead product. The functional champions for additional modules already existed inside the firm. And customer acquisition cost dropped dramatically because expansion revenue didn’t require acquiring a new logo.

Here’s the core lesson I learned:

It is far easier to sell multiple products into one vertical than it is to sell one product into multiple verticals.

That focus allowed us to scale efficiently and sustainably. Over time, we built a suite of seven products within our vertical market. In fact, the seventh product we introduced was one of the six strategies I used to double the company prior to exiting—an outcome that would have been far more difficult, if not impossible, had we pursued horizontal expansion instead.

Why Horizontal Vendors Struggle to Enter Vertical Markets

Horizontal vendors consistently underestimate how difficult it is to succeed inside a vertical. Their products are designed for breadth, not depth. Their sales and marketing teams speak in general business terms rather than the language of the industry. Their implementations lack domain nuance, and their roadmaps prioritize broad applicability over vertical specificity.

Vertical buyers sense this disconnect immediately.

Even excellent horizontal platforms struggle with this mismatch. Vertical buyers want precision, industry accuracy, and a deep understanding of how their world actually operates. When that understanding isn’t there, no amount of scale or brand recognition can compensate.

Marketing in a Vertical: Speaking the Industry’s Language

Marketing inside a vertical is fundamentally different from selling a horizontal product. Each industry has its own vocabulary, conferences, associations, and cultural norms, and vertical buyers can immediately tell whether a vendor truly understands their world. Horizontal companies often arrive with generic messaging, and industry insiders recognize the disconnect instantly. In vertical markets, language, references, nuance, and credibility all matter. This is why specialized vendors consistently outperform generalists: they speak the industry’s language fluently.

Customer Intimacy: An Important Moat

In the vertical software company I operated, one philosophy guided us from the beginning: know the customer deeply—not just the workflows, but the people. I wanted our implementation and support teams to understand the personalities, communication styles, and operational priorities of the individuals they worked with. That level of familiarity built trust, accelerated adoption, and surfaced insights no horizontal vendor—with thousands of generalized customers—could replicate. Over time, customer intimacy became a structural moat. You can’t fake domain understanding, and it’s one of the qualities sophisticated acquirers like Roper Technologies look for—one of the reasons they ultimately became interested in our company.

The Complexity of Vertical Product: Where Features Become a Moat

Vertical software is rarely simple. These systems evolve into deeply nuanced operational platforms with hundreds of screens, dozens of role types, intricate permission models, and hundreds of specialized reports. This complexity reflects the reality of the industry, not poor design. Vertical software users are extremely picky—and that is a good thing. They want software that mirrors their exact workflows and operating assumptions. A great vertical product fits the customer like a hand in a glove. Once they experience that level of precision, switching becomes extraordinarily difficult. This is where complexity turns into defensibility.

Plugging Into the Vertical Ecosystem

Every vertical has its core systems—the operational backbone everything else depends on. In professional services firms, for example, two accounting platforms dominate the industry: Elite and Aderant. These are the true systems of record. By building deep integrations into both, we gained visibility into staffing, utilization, workflows, relationships, performance inputs, and the real operational patterns inside each firm. And the deeper the integration, the harder you are to remove. Over time, you begin to wrap around the system of record like an octopus, touching everything.

What Is a System of Record Anyway?

A System of Record (SOR) is the authoritative, indispensable source of truth for a company’s most critical operational data. If a business were forced to cut every system due to budget pressure, the system of record would be the last one unplugged. Vertical vendors don’t need to be the system of record—though ideally they are—but they do need to be inseparable from it. That tight coupling creates enormous stickiness and long-term defensibility.

Viral Distribution Inside a Vertical

One of the most powerful dynamics in vertical markets is how naturally a product can spread within the industry. People move between firms and bring the software they’re familiar with. New hires ask for the system they already know. Job descriptions begin to require experience with it. And teams introduce it organically to new colleagues. Adoption becomes less about selling and more about becoming part of how the industry works.

Pricing Power & Price Elasticity

Vertical market buyers are willing to pay more because their use cases are highly specific and their pain points are acute. An economic buyer in a vertical is not choosing between ten broadly similar tools; they are choosing between a generic solution that only partially fits and a vertical solution that matches their workflow exactly.

That distinction dramatically increases price elasticity. Vertical software buyers care far less about feature counts and far more about whether a system eliminates real operational bottlenecks—staffing errors, compliance failures, utilization inefficiency, lost billable hours, revenue leakage, and project breakdowns. These are not theoretical problems; they are expensive ones.

Champions inside the firm—HR, recruiting, talent development, and workflow owners—feel this pain directly. When a product meaningfully improves their day-to-day work, resistance to pricing drops. They are not buying “software”; they are buying relief from a high-friction workflow that no horizontal system can solve properly.

Because vertical products remove real financial and operational pain, buyers willingly pay for accuracy, specificity, and depth. And once a system becomes embedded in core processes, the cost of switching quickly exceeds the cost of staying—reinforcing pricing power over time. Those dynamics strongly influenced how I think about durable value creation, and they carried directly into how I approach investing at Upward Trajectory Fund.

AI and Vertical Software

AI is unquestionably displacing certain categories of software, and no one fully knows where things are going. My view is that in most industries, AI will sit on top of vertical market software rather than replace it. Vertical systems often contain enormous complexity — sometimes hundreds of database tables, hundreds of screens, and thousands of features — all built around the real-world workflows of a specific industry. It is far more practical for AI to become a layer that enhances these systems than to rebuild the entire vertical stack from scratch.

We don’t know which companies will ultimately stand up against AI, but vertical software has one advantage others do not: it is more than software. It is the relationships, trust, and long-term customer intimacy built inside a specific industry. That combination gives vertical market software a better chance of enduring in an AI-driven world.

Why I Will Always Love Vertical Market Software Companies

Vertical software is where specialization becomes an advantage, where customer intimacy compounds over time, and where complexity turns into defensibility. It’s where capital efficiency thrives, word-of-mouth accelerates adoption, multi-product expansion feels natural, and switching costs harden almost by themselves. Even in an AI-driven world, vertical software isn’t replaced — it is amplified. These companies quietly run the world’s industries and create durable, meaningful value not through hype, but through depth.

That is why I love vertical market software companies.

My writing page has more articles on various topics.

How Running Became a Passion - Without Me Realizing It

I never set out to become a better runner. For most of my adult life, running was simply something I enjoyed — a couple of easy runs each week folded into a broader fitness routine that was centered on strength training. It was familiar, uncomplicated, and restorative.

Then the COVID pandemic arrived.

Gyms closed. Routines dissolved. Life contracted into a much smaller radius. Like many people, I found myself pushed outdoors for exercise. I was fortunate to have a small functional gym in my basement (thank goodness), but running quickly became the most consistent part of my days.

What surprised me wasn’t that I ran more — it was how running quietly transformed from a casual habit into a genuine passion. Not overnight. Not intentionally. But slowly, almost without my realizing it.

Within two years, running had eclipsed weightlifting as my primary sport — something I would have told you was not possible before COVID.

Around the same time, I bought a Garmin Fenix watch.

That’s where this story really begins.

This article is a personal reflection on how running quietly became a passion during COVID — and how, along the way, I began paying attention to small improvements that eventually led to a meaningful drop in my 5K time.

Biometric Tracking: A Double-Edged Sword

The Garmin Fenix watch tracks everything: heart-rate variability, VO₂ max, sleep, steps. But one metric quietly hooked me — predicted 5K time.

After each run, I’d check it out of curiosity. And every time, it showed something in the 21-minute range:

21:20
21:15
21:18

Eventually I found myself thinking:

“What if I can get this thing under 21 minutes?”

Then:

“How do I get it under 20?”

Then:

“Now can I get it to 19 minutes-and-change?”

It became an experiment — nothing competitive, nothing public — just curiosity and tinkering. And the more the watch responded, the more enjoyable the process became.

It ultimately took about 18–24 months — from early 2020 into late 2021 and early 2022 — to bring my predicted 5K run time into the high 17s.

At my peak, Garmin predicted my 5km run time at 17:52.

Not a race time — just the model — but directionally accurate based on my pacing, VO2Max and running efficiency.

Running became a quiet demonstration of a familiar idea:

We overestimate what we can do in the short term and underestimate what we can do in the long term.

Understanding the heart rate Zones

Endurance training is often framed around heart-rate zones — not as jargon, but because physiology responds differently at different intensities.

Zone 1 (≤60% max HR): recovery
Zone 2 (60–70%): conversational aerobic base
Zone 3 (70–80%): moderately hard — the so-called no-man’s-land
Zone 4 (80–90%): threshold; controlled discomfort
Zone 5 (90%+): VO₂ max; very hard

Most recreational runners spend years in Zones 3 training. It’s excellent for health.This is what I did too.

But if the goal is to meaningfully improve your 5K time, the adaptations that matter mostly live at the extremes:

Very easy (Zone 2)
and
Very hard (Zone 5).

Polarized Training: The Structure Behind the Improvement

At a certain point, I began researching how elite middle-distance runners train. That’s when I learned about “polarized training”, a structure with decades of evidence behind it. Essentially you cut out most of your zone 3 and zone 4 training and instead work at the ‘polar’ ends of the heart rate zones - Zone 2 and Zone 5.

More specifically you spend 80-90% of your running time in zone 2 and 10-20% of your running time in zone 5. Almost no time is spent in zone 3 or zone 4.

Zone 2 builds the engine (aerobic base):
Mitochondrial density, stroke volume, capillary growth, fat oxidation, lactate clearance, aerobic durability.

Zone 5 raises the ceiling (VO2Max):
Peak oxygen uptake, cardiac output, fast-twitch aerobic capacity, plasma volume, maximal aerobic power.

Zone 3 is productive… but plateaus:
Excellent for general fitness, not ideal for breakthroughs.

Polarized training develops both ends of the system — a strong engine and a high ceiling.

After reading about Polarized training a lightbulb went on for me. I wondered if my prior training style (lots of zone 3 and 4 running) was why my progress had plateaued. I figured I had nothing to lose and would givepolarized training a try.

Norwegian 4×4: The Hard Sessions That Made the Difference

Zone 2 training was quite easy for me to grasp - run at an conversational pace for a long time (60-90 minutes). Zone 2 training is easy and you feel great after. However Zone 5 training was more of a black box to me - if I was supposed to spend 10-20% of my total training time there, how did I structure the ideal program?

When I begin researching zone 5 training, also known as VO2Max training, I learned about Norwegian 4x4 training. This came out of a study from Norway where researchers had athletes exercise for four minutes at VO2Max heart rate, followed by three minutes of active recovery. They repeated the bouts four times. So in total the people exercising spent 16 minutes at VO2Max pace in each workout. The results were profound - the most cited study shows that VO2Max improves by ~8% in just 8 weeks. Over 12 weeks VO2Max can improve up to 13% for non-trained individuals. VO2Max improvements are non-linear. There are ebbs and flows. I experienced this first hand. As I read more, I learned that VO2Max improvements tend to be non-linear. That matched my own experience — progress came in waves, not straight lines.

My hard-day structure revolved around Norwegian 4×4 intervals:

4 minutes hard
3 minutes easy
Repeat 4 times

These sessions are not for the faint of heart.

You spend much of the four-minute effort near your VO₂ max, and there’s a reason this format is ideal for improving 5K performance:

Four 4-minute intervals equals 16 minutes faster than your 5K pace.

A well-known study compared 4, 6 and 8-minute VO₂ max intervals.

The outcome was clear:

4-minute intervals produced the best improvements relative to recovery cost.

I tried six-minute intervals once, just for “fun”. By the end of the workout, I had done 24 minutes at VO2Max pace. Don’t go there. Not worth it. I do not recommend!

I returned to 4×4 quickly.

These Norwegian 4x4 sessions, paired with consistent Zone 2 work, moved my predicted 5K more than anything else.

The Weekly Schedule That Worked

The structure that brought my predicted 5K time down was pretty simple. One day I would do strength training, the next day I would do either a Zone 2 run or a VO2Max run. Rinse and repeat. So a typical week would look like this:

Week 1

• Monday — Long run (Zone 2)

• Tuesday — Full-body strength

• Wednesday — VO₂ max (4×4)

• Thursday - Full body strength

• Friday — Long run (Zone 2)

• Saturday - Fully body strength

• Sunday — VO₂ max (4×4)

Week 2

• Monday — Full-body strength

• Tuesday — Long run (Zone 2)

• Wednesday — Full-body strength

• Thursday — VO₂ max (4x4)

• Friday — Full-body strength

• Saturday — Long run (Zone 2)

• Sunday - Full-body strength

Repeat.

If I needed a rest day, I skipped the strength day — never the run day.

Periodization and Mesocycles - important for systemic Recovery

Later, I began to understand the role of periodization and mesocycles — concepts I hadn’t thought much about at the beginning. Up until then, my training had been fairly linear: similar effort, week after week. Over time, I noticed that progress came more easily when periods of harder training were followed by deliberate pullbacks.

What I eventually learned is that periodization simply introduces rhythm into training — intentional waves of effort and recovery rather than constant intensity. That framing helped explain something I was already experiencing: the biggest gains tended to show up after the quieter weeks, not during the hardest ones.

A mesocycle, as I came to understand it, is just a short block of training — usually a few weeks — with a particular emphasis, whether that’s aerobic volume, VO₂ max work, or something else. Nothing complicated. Just a way of grouping effort into manageable chapters.

Over time, I settled into a simple four-week rhythm that worked well for me:

Three weeks of steady work, followed by one lighter recovery week.

I found that breaking the month up this way made the harder stretches feel more sustainable — and the recovery weeks more satisfying. Even during the “push” weeks, I learned that stepping back for a day or two when needed was part of the process, not a failure of it.

Most of the real adaptation seemed to happen during those quieter periods — a pattern that mirrored much of the rest of the experience.

Gear I Used

I kept gear simple:

Garmin Fenix watch + Garmin heart rate chest strap
(The strap is far more accurate than wrist HR.)

Hoka Shoes
Long Zone 2 runs — soft, forgiving, perfect for 90-minute sessions.

Nike Vaporfly Shoes
VO₂ max interval runs — light, responsive, ideal for speed.

Now that I had the training program in place it was all about finding great places to run.

Toronto: Where My Structure Took Shape

Throughout 2020 and much of 2021, I stayed in Toronto - it was during COVID so we were all stuck anyway.

Long Runs

My long runs followed a similar ritual:

• I’d drive down to the Distillery District

• Start at Balzac’s Coffee

• Run down to the waterfront

• Head west on the waterfront bike path toward Humber Bay Shores

• 35-45 minutes out, 35-45 minutes back

I did this 2x per week:
one 75-minute run and one 90-minute run.

The waterfront bicycle path is exceptional — wide, open, safe and perfect for steady-state running. As long as you stay in the slower cyclist lane, you can comfortably share the path

Running became a form of meditation.

VO₂ Max Runs

My hard sessions happened either down on the waterfront path I mentioned earlier or at Queen’s Park close to University of Toronto campus — its an 800–900m loop I grew to appreciate.

Recovery in Toronto

I’ve always believed in recovery. I have a standing red-light therapy unit at home, and I used it regularly — especially during heavier training periods.

Miami: A Temporary Escape, Not a Lifestyle

In the winter of 2021, Toronto was still under strict COVID lockdown. There was nowhere to go, little open, and a long winter ahead. The city reopened briefly around Christmas before the Omicron variant arrived and restrictions returned.

I decided to spend some time in Miami — it was in the same time zone, and I had heard positive things from a few clients who lived and worked there. I rented a short-term place in Brickell and continued running as part of my daily routine.

It wasn’t a lifestyle shift. Miami felt more like a temporary sanctuary during an unusual period.

Almost unexpectedly, it became the most consistent and enjoyable stretch of running I’d had up to that point.

Zone 2 Runs — South Beach to Sunny Isles

My favorite runs during that period were long Zone 2 efforts after work. Brickell sits on the mainland, and the beach is just across the bridge, connected by a north–south boardwalk that stretches for miles — from South Beach through Mid-Beach and North Beach, past Surfside and Bal Harbour, all the way up to Sunny Isles.

I’d usually start near the southern end of South Beach, around 5th Street and Collins Avenue, where the Art Deco buildings line the street — a style I’ve always been drawn to. From there, I’d run north along Ocean Drive and onto the pedestrian boardwalk, moving steadily through each neighborhood until eventually reaching Sunny Isles. Depending on the day, the run took around 80–90 minutes.

It was during those long, unhurried runs that I began to realize how much I enjoyed discovering a city this way — moving through it slowly enough to notice details I’d otherwise miss.

I’d often end the run in Sunny Isles, stop at Treesome Natural Foods Café, apologize to the staff for being drenched in sweat, grab something simple to eat, and head back. By the end of the run, it had become a familiar routine rather than a destination.

Some evenings I’d start at sunset and finish in the dark. During that stretch of COVID, the rhythm of those runs felt unexpectedly peaceful.

VO₂ Max Runs — North Beach to South Beach

For the harder days, the boardwalk was perfect. I’d head to North Beach do a 10 minute Zone 2 warm-up and then to the 4x4 intervals running south along the boardwalk. Finishing with a 10-20 minute zone 2 cooldown and wind up in South Beach, go to the Whole Foods and then head back to Brickell.

Recovery in Miami

Although I already had an Equinox membership in Toronto (Yorkville), I extended it to the Brickell location while I was in Miami. It became part of my routine during that stretch, particularly for recovery.

I also joined the UFC Gym in the Design District specifically for their recovery lounge, which included a cryogenic chamber, NormaTec compression boots, and a full-body red-light bed. I didn’t work out there — I only recovered there.

Having access to those recovery tools made it easier to sustain the higher training volume during that period.

Miami was never meant to be permanent. It was simply a temporary chapter during an unusual time.

The Two-Year Arc

From the outside, progress can look neat and orderly. Internally, it felt much quieter.

A series of small, steady improvements that accumulated over 18–24 months — the kind of progress you barely notice until one day you do.

That’s one of the quiet joys of running: even as an adult, improvement is still possible, often arriving without fanfare.

Some of my favorite memories from that period are the long Zone 2 runs where I’d have catch-up calls with friends, family, and colleagues. During a particularly demanding stretch at work, those runs became a natural place to reconnect — I’d tell people, “Call me between 6 and 7:30 — I’ll be out on a long run.”

A few moments that still stand out:

• Long waterfront runs in Toronto that felt meditative

• Queen’s Park intervals in the cold

• Sunset runs in Miami ending under the night sky

• Watching VO₂ max inch upward one decimal at a time

Running became a quiet companion.

Where I Am Now

Today, I’m no longer chasing a particular time. That chapter served its purpose.

Lately, I’ve been thinking more about the idea of minimum effective dose — not how much training I can tolerate, but the least amount required to maintain fitness and feel good over the long term. That shift has changed how I approach running.

These days, I usually run twice a week for about an hour, and a couple of times a month I’ll include a Norwegian 4×4 session. It’s enough to stay connected to the practice without turning it into a project.

The passion remains — calmer now, woven into the rest of my life.

Running carried me through COVID, through Toronto winters, through Miami escapes and a very busy time at work. Running is still one of my favorite ways to clear my head if I am working on solving a complex problem.

It remains one of the clearest parts of my day.

A Quiet Ending

Looking back, I’m not sure I fully appreciated it at the time, but running ended up being one of the most stabilizing forces during the process of exiting my company. It created a daily rhythm when many other variables were in flux.

This isn’t a training guide. It’s the record of what happened when a hobby I enjoyed intersected with a pandemic, a Garmin Fenix watch, a handful of routes in Toronto and Miami, and the slow compounding of small improvements.

Some of the most meaningful chapters begin without a plan. Running was one of those chapters for me.

Who knew tinkering with a sports watch would have led me down this path.

Visit my writing page for more articles on other aspects of life.

What I Do When a Problem Won’t Move

I’m partly writing this for myself — for the next time a problem won’t move. Because it will happen again. It always does.

When I was running my company, I’d sometimes hit a problem that simply wouldn’t move. Getting a new product off the ground. Entering a new market. A hiring decision. A strategy question with no obvious path forward. I’d be at my desk, banging my head against the wall trying to figure it out, and nothing I did seemed to unlock it.

I assumed the problem needed more effort. More analysis. More grinding. It rarely did.

Over time — largely through experience — I realized something else: the difficulty wasn’t the problem itself, but the process I was using to think about it.

And once I noticed that, everything shifted.

The Structure of a Stalled Problem

No matter what the problem was (the content), the way I got stuck looked almost identical every time.
No one got stuck quite as thoroughly as I did — I became surprisingly good at it.

When I stripped away the business details about the problem itself, I realized I was usually looping in my head in one of two ways:

1. A Visual Loop

I’d be replaying imagined scenes or “what if” scenarios — like watching the same movie segment over and over.

2. An Auditory Loop

More often, I’d be running an internal dialogue with myself: Should I do this or that? What if I’m wrong? What if this backfires?

Different challenges, same underlying pattern — I’d end up looping in my mind, either visually or auditorily.

And what mattered wasn’t the specifics of the situation — it was the channel I was stuck in.

Once I understood that, the solution became simpler:

• If I was stuck in an auditory loop, I needed to do anything that pulled me out of my head and into movement or sensation.

• If I was stuck in a visual loop, I needed to do anything that interrupted the internal movie.

Everything that follows grew out of that realization.

1. Switching the Channel

Our office building had a gym on the basement level with a great steam room. I worked out there most days anyway, but every so often, when progress on a problem stalled, I’d go down at midday, bring my gym clothes, and sit in the steam room for fifteen minutes. This was quite an effective stress reliever when I was in the process of scaling up the company.

It was one of the simplest ways to get out of my head and into my body.

Heat, breath, and sensation interrupted whatever mental loop I was in. They replace inner noise with something immediate and physical. And once the loop breaks, clarity has a way of surfacing without any deliberate effort.

Running worked the same way. Rhythm, breath, movement — they dissolved mental knots in a way thinking never could.

Even a brisk walk around the block often did the job. Anything that shifted the channel was usually enough.

2. Surrounding Myself With Excellence

After a day of getting nowhere on a problem at the office, I’d sometimes find myself buying a last-minute ticket to something that evening.

One of the benefits of being in Toronto is that there’s always something happening. Koerner Hall. Roy Thomson Hall. The Four Seasons Centre for the Performing Arts. The Art Gallery of Ontario. Random pop-up events. You can decide at 6:45 p.m. that you want to hear a pianist at 8:00 p.m. and actually make it happen.

I wasn’t doing this to be cultured. I simply noticed that these performances pulled me out of whatever loop I was in.

There was always a moment — watching someone completely absorbed in what they were doing — when my internal dialogue would quiet. I’d become drawn into their mastery, their discipline, their years of repetition. And almost through osmosis, I felt influenced and inspired by their excellence.

It also reminded me that anyone who has achieved mastery has been worked through stalled problems many times before. No one escapes that part of the process. I noticed this when watching an excellent foreign film as well.

And once I was absorbed in what they were doing, I wasn’t in my head anymore. All of my attention was on the performer. I suspect my unconscious mind started working on the problem the moment I got myself out of the way.

3. Stepping Away Entirely

Another thing that worked for me was travel.

Sometimes it meant going to a new city altogether. Other times it was as simple as exploring a different part of Toronto. Either way, it snapped me out of autopilot.

In a new environment, my attention naturally shifted. I’d find myself figuring out the metro, scanning street signs, navigating unfamiliar streets, looking for a café I’d never been to, noticing small details I’d normally overlook.

It got my brain working differently.

I found that when I stayed in the same routines — same route, same cafés, same environments — I was also using the same mental apparatus to think about the problem. If that apparatus wasn’t producing answers, staying inside it rarely helped.

But when I went somewhere new, even briefly, my brain switched modes. It began using different pathways. And often, the solution to the problem lived in that different pathway.

Even short trips — Madrid to San Sebastián, for example — reset everything. Running through Retiro Park. A chocolate shop. A train north. Ocean air. Small rituals in unfamiliar places.

When my internal pattern changed, the problem rearranged itself.

The Meta-Pattern

Looking back, the three approaches — switching the channel, surrounding myself with excellence, and stepping away entirely — all did the same thing.

They broke the loop.

They changed the mode I was in.

They gave me enough distance for clarity to surface naturally.

And the moment I stopped trying to solve the problem from inside that pattern, the problem often solved itself.

When All Else Fails

When nothing else worked, I slept on it.

John Steinbeck once wrote:
“A problem difficult at night is resolved in the morning after the committee of sleep has worked on it.”

That matched my experience almost exactly. The solutions I couldn’t force during the day often arrived unannounced the next morning — as if some quieter part of me had kept working long after I had stopped.

Uh-oh — I think I’ve just come down with a case of writer’s block. I’m trying to find the best way to finish this article, and I’m stuck in my head.

Hang on a second. I hear Seong-Jin Cho is coming to town to play some Chopin. I think I need to follow my own advice and buy a ticket right now.

I’ve written about several other topics. Visit my writing page for a complete list.

Roper Technologies — A Company You Probably Haven’t Heard Of, Built to Compound

People often ask me, “So who bought your company?”

And when I say, Roper Technologies, I usually get the same puzzled look:

“Who?”

It makes sense. Roper isn’t a household name. They don’t advertise, they don’t dominate headlines, and they don’t behave like a company that wants attention. Most people outside certain corners of the vertical market software world have never heard of them..

And yet, at the time of writing, Roper Technologies is an S&P 500 and NASDAQ-100 company with a market capitalization of roughly $65 billion.

They are one of the most quietly exceptional businesses in the public markets — admired by operators, respected by investors, and studied by anyone who cares about long-term compounding. What makes Roper extraordinary isn’t just its size or financial performance, but its philosophy: quiet excellence, deep customer intimacy, operational autonomy, and a compounding flywheel built on free cash flow.

This is why Roper stands out — and why I think they’re one of the most unique companies in America.

What Roper Actually Does — in Simple, Human Terms

Roper is not a typical tech company. They don’t build consumer apps, operate social platforms, or chase hype cycles.

Instead, Roper owns dozens of mission-critical vertical market software businesses — companies that quietly power the essential workflows of hospitals, universities, water systems, laboratories, legal practices, engineering firms, and other industries most people rarely think about.

These businesses aren’t glamorous. They’re indispensable.

Once installed, their software becomes deeply embedded in a customer’s operations. Replacing it would be disruptive, risky, and often unthinkable. That’s the common thread in the companies Roper chooses: niche dominance, essential functionality, and long-standing customer relationships.

Roper favors businesses where customers don’t merely use the product — they depend on it.

The Snowball: How Free Cash Flow Builds More Free Cash Flow

If there’s one idea that explains Roper’s entire engine, it’s free cash flow — the money left over after a business pays its bills and reinvests in itself.

What’s free cash flow, really? It’s simpler than it sounds. If a business brings in $100 and pays everyone — salaries, rent, servers, all the essentials — whatever remains at the bottom of the bowl is the dough it actually gets to keep. That’s free cash flow: the money a company can use however it wants. Free cash flow is the free dough.

For most companies, growth requires spending: more people, more offices, more marketing, more everything.

Roper grows by generating more free cash and then deploying it with extraordinary discipline. The model is beautifully simple:

Roper acquires a profitable niche software company.
That company produces free cash.
Roper uses that cash to buy another great company.
That company generates even more.

The snowball grows — steadily, quietly, predictably.

It’s a compounding loop: free cash flow → reinvestment → acquisition → more free cash flow.

Over time, this becomes a self-reinforcing flywheel. The machine strengthens simply by continuing to operate. Some observers describe Roper as “a free cash flow compounder disguised as a software conglomerate.” Once you understand the model, the description feels exactly right.

From Industrial Tools to Vertical SaaS Empire

One of the most impressive aspects of Roper’s story is its evolution.

Decades ago, Roper was primarily an industrial tools company. Over time, something subtle but remarkable happened: they began selling off hardware businesses and reinvesting that capital into asset-light, high-margin, recurring-revenue software companies.

This transition wasn’t loud or dramatic.
It was patient.
It was deliberate.
And it reshaped the entire business.

Today, a large majority of Roper’s value is driven by software. Many commentators describe the company as:

“A software empire inside an industrial shell.”

Once you see the transformation, you realize how rare it is: a public company steadily reallocating itself toward durability, cash flow, and long-term resilience — without ever needing to announce a “reinvention.”

They just quietly became excellent at something better.

Customer Intimacy: The Moat You Can’t See

When I met Roper’s head of M&A during the sale of my business, one concept surfaced again and again: customer intimacy.

Roper doesn’t just buy companies that sell software. They buy companies where the software is trusted, relied on, and incredibly hard to replace.

Their ideal business has:

• long-standing customer relationships

• deep integration into the customer’s daily workflow

• switching costs that reflect genuine reliance

• a reputation for reliability and partnership

This is why churn is low.
This is why margins are high.
This is why revenue is predictable.

And it’s why some vertical market software companies fit Roper so well.

Our business, for example, had strong margins, recurring revenue, and unusually deep customer relationships in our niche. It was less about size and more about alignment — we operated with a philosophy similar to theirs, which made the fit natural.

The Federated Model — How Roper Stays Big by Acting Small

One of the most unusual things about Roper is the size of its headquarters.

Despite being a $65B company, their corporate office in Sarasota is small — intentionally small. They don’t centralize decisions. They don’t impose heavy processes. They don’t fold acquisitions into giant corporate structures.

Instead, Roper operates a federated model, meaning:

• each company keeps its own CEO

• each company maintains its own culture

• decisions are made close to the customer

• headquarters acts primarily as a capital allocator and strategic steward

It’s like a group of independent states sharing a common treasury and philosophy.

This approach preserves what made each company special in the first place. Autonomy, accountability, and closeness to the customer remain intact — and excellence is protected rather than diluted.

Roper vs. Danaher vs. Constellation (The Clear, Simple Comparison)

Three companies are often admired for their acquisition philosophies: Danaher, Constellation Software, and Roper.

Here is the simplest way to distinguish them:

Danaher

• Very process-driven

• Uses a centralized operating system (DBS)

• Imposes consistent methods across all subsidiaries

• Still more industrial in nature

Constellation Software

• Ultra-decentralized

• Buys hundreds of very small vertical software companies

• Reinforces autonomy to the extreme

• Reinvests almost all cash flow

Roper

• Buys fewer, larger, more mature vertical software companies

• Combines autonomy with thoughtful oversight

• Focuses intensely on free cash flow

• Patient, selective, and structurally stable

If Danaher is “operational discipline,” and Constellation is “decentralized volume,” then Roper is “curated excellence with compounding cash flow.”

The Rise of the Mini-Constellations

In recent years, I’ve noticed a growing trend among founders who have sold their companies. Many are now trying to build smaller versions of Constellation or Roper — acquiring niche software businesses, keeping the teams in place, and rolling them up into long-term investment vehicles.

It’s an appealing strategy. These companies are often profitable, defensible, and operationally simpler than large horizontal software platforms.

The challenge is that the space has become crowded. Many small software companies now receive a steady stream of inbound calls from would-be acquirers. For founders, the conversations start to blur together. The scripts sound familiar. The offers feel increasingly interchangeable.

Roper stands apart as one of the few organizations that has executed this strategy successfully at true scale. One key differentiator is discipline: Roper tends to acquire fewer, much larger, more mature businesses — companies with established cash flow, deep customer relationships, and staying power.

Why Roper Stands Out

Roper is the opposite of the loud, growth-at-all-costs mindset that has dominated tech for the last decade.

They value:

• autonomy over micromanagement

• durability over excitement

• relationships over rapid scaling

• recurring revenue over risky bets

• long-term compounding over short-term optics

They don’t need to be famous. They don’t need to be flashy. They simply need to stay excellent — and excellence, given time, compounds.

Roper is a reminder that some of the greatest businesses in the world aren’t the ones everyone has heard of — they’re the ones quietly getting better, year after year, while the rest of the world is busy looking elsewhere.

Compounding Excellence

When I started Upward Trajectory Fund, the purpose was straightforward: to compound capital over the long term. But I also wanted a tagline that felt more aspirational — something that captured not just the strategy, but the standard. That’s how Compounding Excellence emerged. Looking back, I suspect the seed of that idea was planted during my journey working with the team at Roper through the sale of my business. Their philosophy showed me that excellence isn’t something you declare — it’s something you build patiently, through disciplined choices that accumulate over time. What you nurture compounds. And when excellence compounds, the results speak for themselves.

For more articles about entrepreneurship and other aspects of life too, visiting my writing page.

Foreign Films: One of My Favorite Ways to Learn About The World

Every September, back when I was running my company, I would take a week and a half off work and disappear into the Toronto International Film Festival (TIFF). TIFF always starts on the first Thursday of September and ends on the second Sunday — a ten-day marathon of stories from around the world. It became a ritual for me. A reset. A quiet celebration. And eventually, one of my favourite ways to learn about the world — through foreign films.

When I first started attending TIFF, I’d dabble — a foreign film here, a foreign film there. But over the years, something shifted. Each time I logged in to book my tickets, I noticed my selections tilting more and more toward international cinema. At some point, almost without realizing it, foreign films became the majority of what I watched.

And since I’m no polyglot, the more subtitles, the better.

One of the best festivals I ever experienced was 2023, when Hollywood was shut down by the writers’ and actors’ strikes. Most people were disappointed — no red carpets, no studio premieres, no celebrity appearances. But I felt like a kid in a candy store. Cameron Bailey and the TIFF programming team scrambled to fill the lineup with films from around the world, and it became the most foreign-film-heavy TIFF I’ve ever attended. I didn’t miss the celebrity culture for a second.

Watching three films a day for ten days is a kind of immersion. Some people perform sentiment analysis by feeding thousands of tweets into a model to understand how a culture is thinking. For me, watching foreign films back-to-back at TIFF does something similar. You begin to feel the emotional pulse of the world that year — its anxieties, its humour, its moral struggles, its family dynamics, its dreams, and its disillusionments.

It’s like taking a trip around the world without leaving Toronto.

One thing that fascinates me about foreign cinema is the sheer determination required to make it. Directors often spend years fighting for budgets, negotiating censorship, or pushing through political resistance just to get their story out into the world. And there’s a strange paradox I’ve noticed: the more repressed or culturally constrained a society is, the more explosive and daring its films often become.

Two cultures that immediately come to mind are Iran and South Korea.

Iranian Cinema

Despite heavy artistic restrictions, Iranian filmmakers routinely produce some of the most emotionally rich and morally sophisticated films in global cinema. What makes Iranian cinema so compelling is its restraint — meaning is often conveyed through implication rather than declaration, through silence rather than spectacle.

A Hero (2021) — Directed by Asghar Farhadi

The film explores truth, reputation, and moral ambiguity with remarkable subtlety. Small decisions carry enormous weight, and the story unfolds in shades of grey rather than clear victories or villains — a hallmark of Iranian storytelling. It’s a powerful example of how creativity finds a way to surface even under pressure.

Korean Cinema

Korean cinema is equally remarkable, though its intensity expresses itself differently. Born from a conservative society navigating rapid economic growth, social stratification, and enormous performance pressure, Korean films often feel tightly wound — precise, urgent, and emotionally charged.

Parasite (2019) — Directed by Bong Joon-ho

The film blends dark humour, class tension, and suspense with surgical control, revealing how inequality quietly shapes daily life. It’s both entertaining and unsettling — and emblematic of a broader Korean cinematic tradition that isn’t afraid to interrogate power, status, and survival. As with Iranian cinema, Parasite is just one entry point into a much deeper body of work.

Over time, as I watched more films from more countries, I realized that at the heart of every great story — regardless of culture — is the same structure. Years ago, I read The Writer’s Journey, which simplifies Joseph Campbell’s The Hero with a Thousand Faces. Campbell’s book is brilliant but dense; Vogler’s version makes the ideas more accessible.

When you strip away setting, language, genre, and style, every hero / character arc story reduces to a simple architecture:

A protagonist
A challenge
An internal struggle
A transformation
A return

Two films in particular capture this beautifully — and they remain two of my favourite foreign films of all time.

The Secret in Their Eyes (2009)

Directed by Juan José Campanella

Set against the backdrop of a decades-old unresolved murder, the film follows a retired Argentine legal investigator as he revisits a case that never truly left him. Beneath the mystery lies a much quieter story about regret, restraint, and unrealized love.

The protagonist, played by Ricardo Darín, begins the story somewhat timid — professionally, romantically, morally. He writes a letter that begins with the words “I fear” (tengo miedo) and, in a single moment of courage, changes one letter so it becomes “I love” (te amo). That tiny shift represents the entire character arc. He becomes someone new — not because the world changes, but because he does.

The Lives of Others (2006)

Directed by Florian Henckel von Donnersmarck

Set in East Berlin during the Cold War, the film centers on a Stasi officer tasked with surveilling a playwright and his partner, immersing the viewer in a world of constant observation, suspicion, and quiet control.

Over time, the officer slowly transforms from a dutiful instrument of the state into an empathetic protector of the very people he is assigned to watch. Through exposure to art, intimacy, and moral consequence, he regains his humanity. It’s one of the greatest portraits of internal change I’ve ever seen.

What Foreign Films Have Taught Me

And that, ultimately, is what foreign films have taught me: while cultures differ wildly in how they express emotion, humour, family, hierarchy, or conflict, the underlying human journey is the same everywhere. We are all wrestling with fear, courage, love, desire, identity, and meaning — just in different languages.

By no means am I a film buff or a critic. I simply love learning through immersion, and foreign films offer a remarkable window into the inner life of a culture. They’re not a substitute for travel, food (such as places like San Sebastian), or meeting people from that culture — those are still the best ways to understand the world. But foreign films come surprisingly close.

After watching many foreign films, they remain one of my favourite ways to learn — about others, about the world, and sometimes about myself.

Elsewhere, I’ve written about other formative chapters, including the process of selling my company.

To read more of my writing, visit my writing page.