Optionality doesn’t show up when a buyer calls.
It’s built much earlier through how a company is financed, how it grows and the decisions made long before any transaction is on the table.
TechExit.io recently sat down with JD Saint-Martin, Founder of Chronogolf (acquired by Lightspeed) former President of Lightspeed and now Managing Partner at Boreal Ventures, to unpack what it takes to build that kind of leverage.
Having built, sold, and then helped scale the business within Lightspeed, JD has seen the full lifecycle and one idea stood out: the best outcomes are designed, not timed
Key takeaways:
- Optionality is created through disciplined operating decisions, not timing
- Strong acquisition outcomes are built through long-term relationships
- Customer health is the foundation of valuation
It’s easy to assume growth leads to a strong outcome.
In reality, buyers focus on durability, how revenue holds up, how predictable it is, and how the business performs under pressure. Founders who understand that early build differently.
Optionality Starts With How You Build
Chronogolf wasn’t built around chasing large rounds or optimizing for short-term valuation. Instead, the company focused on staying flexible and in control.
“We raised small rounds… to maintain maximum optionality and limit dilution.”
That approach kept the business close to cash-flow positive and reduced dependence on external capital. As a result, decisions could be made based on opportunity rather than urgency.
When acquisition discussions eventually emerged, the company wasn’t trying to create leverage in the moment. It already had it.
This is where many founders get caught off guard. Optionality is often thought of as something you gain when multiple offers appear. In practice, it’s something you earn by building a company that doesn’t need to accept any of them.
Relationships Shape The Outcome Before The Process Begins
Chronogolf’s acquisition by Lightspeed didn’t begin with a formal process or outreach. It developed over time through a partnership that was already delivering value.
“We became partner of the year… every year from 2016 to 2019.”
By the time acquisition conversations began, both sides had a clear understanding of how the products worked together and how customers were benefiting. That familiarity removed much of the friction that typically exists in M&A.
JD also made a point of maintaining strong relationships across the competitive landscape.
“I knew all my competitors on a first name basis… we’d compete during the day and grab a beer at night.”
That proximity provided insight into how the market was evolving and ensured that when opportunities arose, they were grounded in real understanding rather than speculation.
For founders, the takeaway is practical. Acquisition readiness is not only about financial performance or legal structure. It’s also about building relationships early, long before a transaction is being considered.
Growth Without Retention Creates Risk
From JD’s perspective, working across both operating and acquisition roles, one of the most common issues he sees is a disconnect between growth and customer health.
“The kiss of death is when companies focus on adding logos and neglect the health of those customers.”
It’s possible to grow quickly while underlying retention weakens. That imbalance often remains hidden until growth slows.
“Once that happens, you realize it’s a depreciating asset.”
Buyers are increasingly focused on this dynamic. Rather than relying on top-line metrics, they analyze how customer cohorts behave over time and whether those relationships are expanding or contracting.
Companies that show consistent expansion and retention create confidence. Companies that rely on constant acquisition to sustain growth introduce uncertainty.
In that sense, valuation is not just a function of revenue. It reflects how durable that revenue is.
The Right Exit Accelerates What Comes Next
When Chronogolf was acquired, the company was still early in its growth trajectory.
“It was doing five or six million in ARR… we didn’t feel like this was the end of the journey.”
The decision to sell wasn’t about stepping away. It was about positioning the business for its next stage of growth.
Within Lightspeed, that growth accelerated. The golf division expanded significantly, reaching roughly $50 million in revenue and establishing a leading position in its category.
This reframes how founders should think about exits. Rather than viewing them as endpoints, they can be part of a broader strategy to unlock scale, distribution or product capabilities that would be difficult to achieve independently.
The critical question becomes where the business has the best chance to grow, not simply whether it can be sold.
Building The Power To Choose
One of the clearest insights from the conversation is how early these decisions begin.
JD believes founders should think about outcomes before they become urgent.
“Arguably, you should think about that before you start the company.”
This doesn’t mean building with the sole intention of selling. It means understanding the ecosystem you are operating in, who the relevant partners and acquirers are, how value is created and what makes a company strategically important.
From there, the focus shifts to building a business that keeps those paths open.
This is where the idea of optionality becomes tangible. It’s not about indecision. It’s about creating enough strength and flexibility to make decisions from a position of control.
Final Thought
The companies that achieve the strongest outcomes are rarely optimized for a single moment. They are built with discipline, clarity and an understanding of how value compounds over time.
That discipline shows up in capital strategy, in customer retention and in the relationships developed long before a deal is ever discussed. By the time an opportunity appears, the groundwork has already been laid.
This is exactly what TechExit.io is built around. It’s not about helping founders chase transactions. It’s about helping them build companies that are worth acquiring and structured to choose when and how that happens.
Through sessions with leaders like JD, founders develop the skills behind real optionality. They learn how acquirers think, how value is assessed and how to operate in a way that creates leverage over time.
In the end, the difference is simple. Some founders are deciding whether they can take an outcome. Others are deciding whether they want to.
TechExit.io: Learn how to acquire or get acquired. Join us in our newest TechExit.io Calgary as we continue exploring how founders can build companies that command strong outcomes in today’s market.