Late one evening at Hy’s Steakhouse in downtown Vancouver, entrepreneurs Kate Bouchard and Ada Slivinski were deep in conversation over drinks.

Like many long dinners at the city’s famously old-school steakhouse, the discussion wandered—from purely personal updates to marketing, and strategy, and ideas about how businesses and leaders can navigate the complex cultural moment we are in.

By the end of the night, Bouchard realized something: the conversation they were having was exactly the kind she wished more people could hear.

That realization eventually became Branded Assets, a new podcast where the Vancouver entrepreneur unpacks the realities of building companies, understanding modern brands, and navigating the power dynamics of business.

“My goal for Branded Assets is to educate, elevate, and create space for women to feel informed, confident and culturally fluent when it comes to these topics,” Bouchard says.

Bouchard is no stranger to entrepreneurship.

For years she was best known locally as the founder of Loba, a wellness tech startup that built a smart supplement organizer. The product landed distribution at Best Buy Canada and earned recognition from The New York Times’ Wirecutter.

But behind the scenes, the journey was far less polished than the headlines suggested.

Bouchard raised hundreds of thousands of dollars, invested heavily herself, and spent years navigating venture capital conversations, manufacturing hurdles, and the startup pitch circuit—all while pregnant and later postpartum.

“I was in the media, and I was on the tech and startup pitch circuit for about two years, most of that while pregnant and postpartum,” she says. “Which was a trip, to say the least.”

Ultimately, Loba shut down. But the experience left Bouchard with a deeper understanding of the financial and structural realities founders face.

“I learned so much during the time that I was building Loba,” she says. “I was exposed to venture capital, angel investing, intellectual property, cap tables. I participated in incubators. I spoke on panels.”

It also revealed some of the deeper challenges women founders encounter when raising capital.

“Unfortunately, I also saw a lot of the worst of what it is to be a woman raising,” she says. “Let me tell you, the system is not set up for us to succeed, especially if we have young children.”

Those experiences—and the lessons she wishes she had known earlier—form the foundation of the podcast.

“There is so much that I wish I knew before starting Loba,” Bouchard says. “And now that I’ve been through it, I want to take all of those lessons and insights and share them.”

One of the podcast’s most candid moments comes when Bouchard explains how she financed her entrepreneurial journey.

There was no venture capital windfall at the beginning—just personal assets and a willingness to take risk.

“There is no trust fund, no tech bro boyfriend,” she says. “Just some gutsy moves, a mortgage, and honestly a whole lot of risk.”

After leaving the corporate world, Bouchard used equity from a Vancouver condo to access more than $100,000 in capital through a remortgage. The funds helped pay for Loba’s product design and early software development.

“I will never forget walking out of the bank after remortgaging my apartment… with that cheque in hand,” she recalls. “Messaging my spouse and saying, ‘Are we really going to do this? Am I making the right decision?’”

In Canada, she notes, startup financing often comes with a reality founders don’t always talk about: personal guarantees.

“If you sign a personal guarantee, the bank can come after your personal savings, your home, any other assets,” she explains. “And it doesn’t matter if you’re incorporated or not.”

Eventually, Bouchard decided to wind down Loba when the financial risks began colliding with a new stage of life.

“I had a baby just as Loba was getting to market,” she says. “All of a sudden I had these obligations—daycare, family—and I had met the ceiling of my risk tolerance.”

While Branded Assets includes personal founder stories, it also explores how brands succeed—or fail—in today’s cultural landscape.

That’s where conversations like the one at Hy’s come in.

Slivinski, who sold her PR agency and now works as a growth strategist and senior advisor to CEOs, joined Bouchard on the podcast to dissect the cultural forces shaping modern brands.

Among the topics: why luxury brands are leaning away from AI-generated marketing, the struggles facing dating apps like Bumble, and how consumer buying behaviour is shifting.

“Dating apps aren’t just tech products,” Bouchard says during their conversation. “They’re connected to culture.”

Slivinski agrees—and argues that deeper social shifts are reshaping entire industries.

“People are not dating anymore the way they were even five or ten years ago,” she says. “The Economist actually refers to this as a ‘relationship recession.’”

Another emerging theme is how purchasing decisions increasingly happen in private spaces rather than public social media feeds.

“Sales are happening in the group chat,” Slivinski says. “If I’m looking for something, I’m asking someone I trust—not just clicking an ad.”

At its core, Branded Assets is designed to recreate the kinds of conversations founders and operators often have behind closed doors.

Some episodes feature vulnerable founder reflections. Others offer tactical advice. And some lean into what Bouchard jokingly calls “billion-dollar gossip”—breaking down the brands and cultural signals shaping modern business.

Across all of them, the goal is the same: transparency.

“There are so many stories of founders betting it all on themselves,” Bouchard says. “But what we usually see are just the glossy headlines when a startup hits it big.”

The reality, she argues, is far more complicated—and far more instructive.

Sometimes it means taking big swings.

And sometimes, she says, it means learning from the ones that miss.