Most founders spend years trying to create options.
The difficult part isn’t creating them; it’s knowing which one to take when circumstances change.
At TechExit.io Vancouver 2026, Swish Goswami, Co-Founder of Surf and current Head of Growth & Marketing at Boardy, joined Gena Custode of Roynat Capital to share the story behind Surf’s acquisition journey. What emerged was a reflection on changing markets, failed transactions and the decisions founders face when the path they expected suddenly disappears.
Throughout the conversation, one idea surfaced repeatedly: optionality isn’t something that appears during an exit process. It’s built through years of decisions that create flexibility when conditions inevitably change.
Key takeaways:
- Optionality is built long before an exit becomes a possibility
- Acquisitions can accelerate value creation as well as growth
- Trust, transparency and diligence matter long before closing day
When The Plan Changes
When Surf surpassed $2 million ARR, the company’s trajectory appeared clear. The team was preparing for a Series A raise, acquisitions had accelerated product development and the business had built meaningful momentum.
Then the market shifted.
Investor attention moved toward AI, fundraising became more selective and the assumptions supporting the next stage of growth began to change. As Swish described it, Surf found itself in “a weird middle point,” beyond what many seed investors wanted to fund but not yet where Series A investors expected it to be.
Nothing was fundamentally wrong with the business but the environment around it had changed and that distinction mattered.
Rather than forcing the original plan to work, the team stepped back and started evaluating a broader set of possibilities. The conversation became less about raising capital and more about identifying the path that would create the strongest long-term outcome for employees, shareholders and customers.
Those discussions eventually led Surf toward acquisition conversations. Not because options had disappeared, but because maintaining flexibility had become increasingly important.
Building Value Sometimes Means Buying It
Long before Surf was discussing its own future with potential acquirers, the company was using acquisitions as a growth strategy.
The acquisitions of Social Rank and Player were not driven by a desire to get bigger but by time.
Like many startups, Surf had more opportunities than engineering resources. Product ideas continued to emerge, customer needs evolved and the roadmap kept expanding.
Building everything internally would have required years, thankfully acquisitions offered another path.
As Swish explained, if a transaction could be completed in a matter of months and eliminate a year of development work, the economics became difficult to ignore.
The lesson extends beyond M&A strategy. Acquisitions are often discussed as exit events, but many of the most effective acquirers use them as tools for accelerating product development, entering markets more quickly and creating value long before an eventual sale process begins.
The Deal That Fell Apart
By early 2024, Surf appeared to have found its next chapter.
A New York-based buyer had presented the company with a Letter of Intent and, over the following months, meetings turned into relationships and future plans started to feel increasingly tangible. Swish was travelling regularly to New York and the process seemed to be progressing exactly as expected.
Then the deal collapsed.
“I wanted to cry, basically.”
The disappointment was more than just losing a transaction, it was the months of momentum had been invested in the process and, with the benefit of hindsight, it became clear that some assumptions about the buyer had never been properly tested.
Like many founders navigating M&A for the first time, Surf had spent significant energy preparing for diligence. Far less attention had been paid to diligencing the buyer.
That experience changed how Swish approached every conversation that followed.
“In the same way that a buyer’s doing due diligence on me, I’m going to do due diligence on them to the nth degree.”
The questions became different. Rather than focusing on demonstrating knowledge or sophistication, the goal shifted toward understanding how the buyer actually operated, what incentives were driving decisions and whether genuine alignment existed beneath the surface.
Looking back, one of the clearest lessons from the experience was that the best deal isn’t necessarily the one attached to the largest number. Trust, incentives and expectations often have a greater influence on long-term outcomes than valuation alone.
Transparency Became An Advantage
The failed LOI created another challenge that many founders know well.
The team.
Acquisition discussions are often kept tightly controlled until a transaction is finalized but Surf took a different approach.
Employees were kept informed about what was happening, why conversations were taking place and what different outcomes could mean for the business. When the deal fell apart, the team received the same level of transparency.
There was no attempt to soften the reality of the situation. The company needed to regroup, move quickly and find another path forward.
That level of openness created trust at a moment when uncertainty could easily have undermined it. Several members of the Surf team would later join Swish at Boardy, reflecting relationships that remained strong despite the challenges surrounding the process.
Leadership often becomes most visible when things don’t go according to plan. This was one of those moments.
Why Optionality Matters
What makes Surf’s story interesting isn’t that the company was acquired. It’s that the company had choices.
By the time acquisition discussions began, the difficult work had already been done. Surf had customers, meaningful revenue, product-market fit and a business that had created genuine value in the market.
Those foundations didn’t guarantee a successful outcome. They did create flexibility.
When fundraising became more difficult, there were alternatives to consider. When the first buyer walked away, there were other paths available. When market conditions shifted, the business wasn’t dependent on a single outcome.
That theme appears repeatedly throughout TechExit.io conversations.
The companies with the most leverage are rarely the ones scrambling to create options during a transaction process. More often, they’re the companies that spent years building optionality before they ever needed it. The same discipline that makes a company attractive to an acquirer often makes it attractive to investors, partners and customers as well.
The transaction may happen at the end of the story, but the ability to choose is usually built much earlier.
Final Thought
One of the more interesting moments in the conversation came near the end.
After helping guide Surf through acquisitions, fundraising challenges and its eventual exit, Swish is preparing to build again.
The experience didn’t diminish his appetite for entrepreneurship. If anything, it sharpened his understanding of what creates resilience.
Markets change, fundraising environments shift and even well-advanced deals can fall apart. Founders have limited control over those external forces. What they can influence is whether they’re building a company strong enough to create choices when those moments arrive.
That idea sits at the centre of TechExit.io’s focus on value creation and optionality. The goal isn’t simply preparing founders for a transaction. It’s helping them build businesses that can attract capital, withstand market shifts and maintain the power to choose when opportunities emerge.
The strongest exits often begin long before anyone starts talking about an exit at all.
Not simply preparing founders for a transaction, but helping them build companies with the leverage, resilience and optionality to decide what comes next.
Those themes will continue in Calgary this October, where founders, operators, investors and advisors will come together to explore what it really takes to create long-term enterprise value in an increasingly uncertain environment.