Choosing what Startups to Invest in

For entrepreneur and investor Bette Bentley, investing has never been about chasing trends or betting on shiny products. It’s about people.

Bentley has built a reputation for backing founders first, believing that the right person can evolve a product, pivot a strategy, and build something enduring—while the wrong person can derail even the most promising idea.

“I invest in founders, not products,” Bentley often says. “Products can change. Stories, grit, and vision don’t.”

As the Co-manager of the private equity fund Brian Bentley LLC, Bentley uses her gut and intuition when investing in brands.

The Founder Comes First

Bentley is drawn to story-driven founders—people who didn’t wake up one day wanting to start a company, but who were pulled into entrepreneurship by a problem they couldn’t ignore. She looks for lived experience, emotional clarity, and an almost obsessive connection to the problem being solved.

She believes the most successful brands are built when a founder’s personal story is inseparable from the business itself. If the founder can’t articulate why the company has to exist—and why they are the one to build it—Bentley doesn’t invest.

Proof in Her Own Portfolio

Perhaps the clearest example of Bentley’s investment philosophy is Skimpies, the underwear brand she founded and invested in herself. What began as a personal solution to a daily frustration grew into a category-creating DTC brand, driven entirely by organic storytelling and community.

Under Bentley’s leadership, Skimpies became a viral success with no paid ads, built a fiercely loyal customer base, and earned backing from national retailers—proving her belief that authentic founder-led brands can outperform traditional marketing playbooks.

“I would never ask another founder to do something I haven’t done myself,” she says. “Skimpies is my proof of concept.”

Brands With Cultural Pull

Bentley’s investment portfolio reflects her instinct for brands that tap into culture, not just commerce. Her portfolio includes AirUp, Poppi, multiple restaurants, and independent films—often backing projects that sit at the intersection of storytelling, community, and lifestyle.

What these investments share isn’t a category or business model, but a clear narrative and founders who understand how to build emotional connection alongside revenue.

She’s particularly drawn to companies that grow through word-of-mouth, community, and authenticity, rather than relying solely on paid acquisition or hype cycles.

A Long-Term View

Bentley is not a short-term investor. She looks for founders who are building with patience, resilience, and a long-term vision—people who see their companies as living, evolving stories rather than quick exits.

Her approach blends creative instinct with operational respect: intuition paired with execution.

“The numbers matter,” Bentley says. “But the story tells me whether the numbers will still matter five years from now.”

Investing as Storytelling

At its core, Bentley’s investment philosophy mirrors how she builds brands: lead with truth, back people with conviction, and trust that when the story is strong enough, the audience—and the returns—will follow.

In a startup world obsessed with speed and scale, Bette Bentley is quietly proving that belief in founders may be the most valuable investment of all.