In a world where venture capital often chases the same patterns, Kristina Simmons is betting on the power of the unexpected. As the founder and managing partner of Overwater Ventures, a $20 million fund investing in deep tech founders, she's built a career by taking chances on entrepreneurs who don't fit the standard Silicon Valley mold.
Simmons' perspective is shaped by her own unconventional journey through the startup ecosystem. From spearheading ecommerce at Lululemon to backing frontier tech at Andreessen Horowitz and Khosla Ventures, she's seen firsthand how a founder's unique background can become their greatest edge.
"My career path has let me see a very wide variety of companies (over 200 in fact), at very different stages, with different maturity levels, with different cultures and ambitions," Simmons says. "That combination changed how I both evaluate and, ultimately, support founders."
The Cost of Pattern Matching
While the venture capital industry prides itself on fueling innovation, Simmons argues that its overreliance on pattern matching often has the opposite effect.
"Pattern matching shows up when investors default to what succeeded in the past and assume it will signal what succeeds next," she explains. "That mindset sidelines outsiders, first-time founders, and people with unconventional backgrounds. It also slows funding for breakthrough ideas in new or unproven categories because they don't resemble established patterns."
For Overwater Ventures, that bias creates an opportunity to spot potential where others hesitate.
"Our team sees this as a competitive advantage," Simmons notes. "Many come from roles that fall outside the traditional venture profile, which helps us notice potential where others hesitate. That perspective lets us back founders and markets that are easy to overlook, but often hold the strongest upside."
Betting on the Unobvious
When evaluating early stage founders, Simmons prioritizes depth of understanding over surface-level credentials.
"At the earliest stages, I focus on how clearly a founder understands the problem they're tackling and why they're the right person to take it on (not just the technology or the solution)," she says.
That emphasis on substance over signaling is particularly critical in complex sectors like health, climate, and food systems, where Overwater Ventures concentrates its investments.
"People who move with pace stand out because they create momentum and find solutions before they have resources," Simmons explains. "I watch how they translate technical complexity into a path that customers and partners can adopt since that determines whether a discovery becomes a company."
Embracing the Unconventional
For founders who take non-traditional paths, Simmons' advice is to stay grounded in the unique strengths that inspire their vision.
"I tell founders to stay grounded in the strengths that brought them to the idea in the first place," she says. "There's no value in reshaping yourself to meet expectations that were never built with you in mind. Focus on execution and let momentum and results speak for you."
That conviction is essential when building companies in emerging or overlooked categories where progress often requires patience and a long-term view.
"The most encouraging signal is the new generation of founders choosing to take on complex, system-level problems," Simmons notes. "They're comfortable working in environments that require patience, technical depth, and a long view. That combination creates the conditions for the next wave of breakthroughs."
Hands-On Support From Day One
As an early stage fund, Overwater Ventures often leads a company's first institutional round. For Simmons, that's an opportunity to provide hands-on guidance when every decision carries an outsized impact.
"Founders should know that we take the lead early, move quickly, and stop at nothing to support our founders. Our goal is to help them commercialize at the right pace so we work directly on hiring, partnerships, product decisions, and GTM [go-to-market]" she says.
"During those first months, we operate as an extension of the founding team. That support helps set the company's direction at a stage when every decision carries outsized weight. In addition to operational and strategic support, we support our founders [in] developing their culture, their physical health and their mental health. We believe all of these things work together to build a high-performing team."
With that holistic approach, Simmons aims to empower a new wave of category-defining companies — by seeing the potential in founders others might miss.
"I'm seeing real velocity at the intersection of AI with biology, the physical world, and robotics," she says. "Those areas are moving from research into company formation fast."
For founders ready to build the future, that momentum is just the beginning.