Can ChatGPT write a founder’s story for them? What does life after exit look like? And how do you get men to back a fertility solution? 

On January 13, four founders took the stage at the MaRS Discovery District for TechTO Together to share hard-earned lessons about fundraising, storytelling, life post-acquisition, and winning at every stage of entrepreneurship.

Jackie Hanson, Sprout Family

Jackie Hanson believes storytelling is a founder’s most powerful tool.

When pitching Sprout, her fertility benefits platform, Hanson used stories to make the problem hit home for investors who might not see it right away. 

For Hanson, real-world examples of the hurdles people face accessing fertility care made the issue feel real and urgent, even to those unfamiliar with it.

“You have to put investors in a position where they can understand: ‘OK, I have a friend that’s gone through this, or my wife went through three rounds of IVF. This is a really big problem, and I want to help solve this,’” she said.

Hanson’s fireside chat explored her transition from investment banking to entrepreneurship, her focus on finding aligned investors, and her strategies for building a business in an underserved market.

Watch the conversation here.

Eldon Sprickerhoff, eSentire

Entrepreneurship isn’t for the faint of heart, just ask Eldon Sprickerhoff.

The founder of eSentire, startup consultant, and author of Committed took the stage to deliver a harsh truth: no AI software, no shortcut, and no hack can replace the lived experience of building something great. 

During his session, Sprickerhoff urged the audience to avoid the trap of instant solutions in the ChatGPT era.

“ChatGPT has read every book, but has no idea what it’s like when shit falls apart,” he said.

Sprickerhoff’s core message? Entrepreneurship is hard, embrace it. He said founders must become their own “chief survival officer,” which means prioritizing endurance and subsistence at all costs. 

Watch Sprickerhoff’s session here.

Corey Gross, Sensibill

What does life after acquisition look like? Sensibill founder Corey Gross has answers.

When his startup was acquired in 2022 by Austin-based Q2 Holdings, Gross wrestled with the same questions that haunt many founders: “Is the process painful? Should I stay on? Am I giving up my baby?”

Gross reassured the audience that post-exit life isn’t as intimidating as it seems. The opportunity, he said, lies in how you as a founder redefine your purpose and sense of self after you sell.

“I was the receipts guy, the expense management guy, the Sensibill guy,” he said. “But when you get acquired, that isn’t who you are anymore. It’s who you were, and now you’ve got to figure out who you want to be.”

Watch Gross’s full session here.

Alwar Pillai, Fable 

To Fable founder Alwar Pillai, fundraising is like a speed-dating session that ends in marriage.

When her startup closed over $30 million CAD in funding last October, she faced a pivotal choice between a Silicon Valley investor focused solely on billion-dollar exits and a growth equity firm prioritizing sustainable outcomes.

The fundraising journey, Pillai explained, is rarely a straight line. Success depends on finding investors who genuinely align with your product and vision, which often means having tough conversations.

“It’s a long-term partnership,” she said. “So you need to be able to ask some difficult questions to your investors.”

In her session, Pillai shared more key strategies for finding the right partners, including aligning on growth goals early and conducting thorough two-way diligence.

Watch Pillai’s full session here.

Images courtesy Sean Pollock for TechTO. Check out the full calendar of TechTO events here.

The post ‘Is there life after acquisition?’ Canadian founders get candid at TechTO first appeared on BetaKit.