Optimist Ventures in Asheville and Their Novel Startup Funding Mechanism: SPA Notes
Jeffrey Kaplan of Optimist Ventures and Venture Asheville on rebuilding Asheville after Helene, and why the SPA is a funding mechanism for non-venture scale startups.
This week we sit down with Jeffrey Kaplan, CEO of Optimist Ventures and Director of Venture Asheville, to dig into one of the most unusual funding mechanisms we’ve come across: the SPA note.
It’s roughly a third company-talk (how Asheville’s startup ecosystem works and how it’s recovering from Hurricane Helene) and two-thirds founder-and-funder lessons (why VC math doesn’t fit an ecosystem builder’s job, and how Jeffrey designed a fund to back “singles and doubles” instead of swinging for unicorns). If you’ve ever wondered what comes after the SAFE note for Main Street businesses, this is the episode.
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Who is Jeffrey?
Jeffrey Kaplan earned his master's in entrepreneurship at the University of Florida, where he stayed on at the entrepreneurship center running co-curricular programs (a disabled veterans program, a women's entrepreneurship summit, a business plan competition, a student incubator) and TA'ing graduate and undergraduate courses.
He's had a couple of startups of his own, one in Charlotte, one in Asheville where"one did okay, one was a pretty big failure", but says he's learned he thrives more on the intrapreneurship side, with structure, accountability, and a budget, as long as the institution lets him be entrepreneurial.
After moving to Asheville, he worked at the software development agency Anthware under John Jones before landing at Venture Asheville, where he's now been eight years. At Venture Asheville he runs the Elevate mentorship program (built on MIT's Venture Mentoring Service), the financing initiatives, and the ecosystem events.
How we met…
Jeffrey has been a key connector for the NC Tweener Fund's statewide expansion. When the fund became the North Carolina Tweener Fund in February, Jeffrey helped me and the team get to know the startups out west. Think: Asheville, up into the Boone area, and beyond, and has sent a steady stream of great companies our way.
Listen/Watch Our Interview:
Most of us know Asheville as beer city, foodtopia, a playground for retirees and 14 million visitors a year. Jeffrey opens by updating that picture. Eighteen months out from Hurricane Helene, which hit on a Friday in late September 2024, the data is starting to come in. The long-term employment hit was about half that of COVID. Decades of population growth stopped in 2025 and even declined for the first time, but the in-migration that remains is now strongest among 25-to-34-year-olds: prime working-age professionals, not retirees. Jeffrey walks through what’s back (Biltmore Village, the River Arts District, High Wire’s new year-round pickleball courts) and what’s gone forever, and lands on a word he keeps coming back to: optimism.
From there, we steer into the heart of the episode: Optimist Ventures and the funding mechanism Jeffrey invented, the SPA note. The origin story is its own lesson in adaptation. Optimist began as a half-million-dollar grant from the Dogwood Health Trust. Then Helene hit, and within the same week a founder in the program, Ginger Frank of Poppy Popcorn, called wanting to commit $100,000, but to a grant program, not a fund. Rather than walk away, Jeffrey spent days thinking until he landed on a hybrid: half the capital as grants and philanthropy, half in a for-profit vehicle for accredited investors, with every for-profit dollar matched by a donation.
Boom: enter the SPA or shared profit agreement.
The conversation closes on what’s next, whether this model can scale to Charlotte or Raleigh, and a heartfelt ask about how the rest of the state can help Asheville finish its recovery.
Highlights
Moneyball the Portfolio: Instead of chasing one home run, Jeffrey set out to build a book of “singles and doubles”… companies that just need to survive six years.
The VC / Ecosystem-Builder Dissonance: An ecosystem builder is measured on jobs and revenue creation, not outlier exits.
The SPA Note, Decoded: A “Shared Profit Agreement” combines a SAFE capped at 3.6% of a $1M valuation with a shared earnings agreement.
The Investor Pitch: Every LP dollar is matched by a donation. But the real sell is community impact.
Applied Technology vs. Developing Technology: The program defines “tech-enabled” broadly.
The Funding Runway: Approximately $225M is flowing into the region through HUD programs, with $17M dedicated to small-business grants.
A Curriculum Built on Competencies, Not Basics: The accelerator is built around entrepreneurial competencies, including opportunity recognition, resilience, and network-building.
The North Carolina Hallmark: “It’s not a zero-sum game. We’re all trying to grow the size of the pie.”
The best founders, and the best fund builders, figure out the structure nobody else was willing to be patient enough to design. Jeffrey did exactly that. Enjoy the conversation.
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