Uploaded September 2026 | Updated September 2026, 6 days ago
In 2019, Ujwal Arkalgud had an offer on the table from a private equity firm based in LA. The deal went all the way through technical and financial due diligence. At the eleventh hour, the buyer pulled out.
That near-miss forced a hard look at why. Founders usually pick one of two games without ever deciding to. Game one is building IP so specific and valuable that a strategic buyer has to acquire it, because they don't have the time or expertise to build it themselves. Game two is building a profitable, self-sustaining business that could keep running without the founder in the room.
Each game calls for a different approach to fundraising, spending, and where the money goes: toward product and proof of IP in game one, toward distribution, margin, and retention in game two.
His company was playing both without realizing it: talking like an irreplaceable, must-acquire product on one hand, while worrying about runway on the other. That confusion, more than anything else, is what he thinks killed the deal.
AI has made game one harder to win. Strategic buyers increasingly believe they can build what a startup built themselves, using AI, and Ujwal says he's heard that directly from prospective customers pitching against his own product.
His advice on timing is not to try to time an exit. Build relationships with the strategic buyers you'd eventually want to sell to, treat them like customers along the way, and let the timing sort itself out.
This one's for any founder who hasn't consciously chosen which game they're playing yet, because the choice gets made for you either way.
What do you think of what Ujwal had to say? Tell us by leaving a comment.
Watch more talks: youtube.com/c/TechTorontoOrg
Upcoming events: techto.org/events
Events calendar: luma.com/TechTO-Events
Newsletter — The read on Canadian tech: blog.techto.org
Membership: techto.org/memberships
#TechTO #TorontoTech #CanadianTech #Startups
In 2019, Ujwal Arkalgud had an offer on the table from a private equity firm based in LA. The deal went all the way through technical and financial due diligence. At the eleventh hour, the buyer pulled out.
That near-miss forced a hard look at why. Founders usually pick one of two games without ever deciding to. Game one is building IP so specific and valuable that a strategic buyer has to acquire it, because they don't have the time or expertise to build it themselves. Game two is building a profitable, self-sustaining business that could keep running without the founder in the room.
Each game calls for a different approach to fundraising, spending, and where the money goes: toward product and proof of IP in game one, toward distribution, margin, and retention in game two.
His company was playing both without realizing it: talking like an irreplaceable, must-acquire product on one hand, while worrying about runway on the other. That confusion, more than anything else, is what he thinks killed the deal.
AI has made game one harder to win. Strategic buyers increasingly believe they can build what a startup built themselves, using AI, and Ujwal says he's heard that directly from prospective customers pitching against his own product.
His advice on timing is not to try to time an exit. Build relationships with the strategic buyers you'd eventually want to sell to, treat them like customers along the way, and let the timing sort itself out.
This one's for any founder who hasn't consciously chosen which game they're playing yet, because the choice gets made for you either way.
What do you think of what Ujwal had to say? Tell us by leaving a comment.
Watch more talks: youtube.com/c/TechTorontoOrg
Upcoming events: techto.org/events
Events calendar: luma.com/TechTO-Events
Newsletter — The read on Canadian tech: blog.techto.org
Membership: techto.org/memberships
#TechTO #TorontoTech #CanadianTech #Startups
