A conversation with Darryl Kirsh, Founder of Fiddlehead Ventures
You started your career in venture capital, then spent decades in corporate restructuring and private equity (especially in Brazil) before returning to early-stage investing. What made you transition back to VC?
I never really left early-stage investing. Even while running turnarounds, I was always intrigued by technology, especially deeptech, and kept investing as what we now call an “angel investor.”
After 20-plus years of 8 a.m. cash-flow meetings, deciding who stays, who goes, and what assets to sell, I decided it was time to hang up my “restructuring guns” and go back to my roots. I wanted to migrate from personal angel checks to a small, focused early-stage fund.
How has your turnaround experience shaped your investment thesis?
Seeing where companies go wrong across sectors and stages gives you pattern recognition. Every startup goes through transformations; in turnaround work we call them restructurings, in ventures they’re called pivots.
We run two theses:
Forward Thinging : the traditional VC crystal-ball work of betting on what will be relevant 10 years from now, with focus on the overlooked niche heavy emphasis on the management team.
Deadpool : distressed investing in companies on the ropes or already shuttered, where the product, IP, or assets are still valuable.
In Deadpool deals, we care far less about the existing team (they didn’t make it work) and far more about placing those assets with a team that can. Sometimes that’s a merger, sometimes building a new team around the asset.
Is there synergy between the two?
Yes, in the sense that any Forward Thinging investment can stumble and require restructuring. But we don’t typically source Deadpool opportunities from our own portfolio: we more often find them in other funds’ portfolios or on the open market, sometimes via bankruptcy auctions.
What verticals do you focus on?
We lean heavily into deep tech, especially biotech and life sciences. One specific area is animal health, which offers shorter regulatory paths and large, growing markets.
The latest investment thesis that we developed (and are very excited about) is looking at drugs developed for humans that failed late-stage trials (stage 2) but had strong pre-clinical results in animals. For example, a parasitic vaccine developed for humans over 45 years is now showing compelling results in livestock and pets, without competing in an overcrowded human health market.
How do you balance “offense” (Forward Thinging) and “defense” (Deadpool)?
We prefer smaller, niche markets where a company can dominate quickly, hit $5–10M in revenue, and become an attractive acquisition target, rather than chasing massive markets that require huge capital and face heavy competition.
Where does AI fit in?
We’ve invested in AI, but are wary of the crowded “pure AI” space. Our preference is applying AI to low-tech industries that have been overlooked. Like a lumber retailer using AI to generate quotes in minutes instead of hours. The goal is time-saving, tangible ROI, not shaving seconds off a developer’s day.
You’ve led turnarounds, supported pivots, and seen many founders up close. What’s a piece of advice you’d give to your younger self?
Everything takes longer than you think. Often twice as long as your five-year plan suggests. In early stages, sales are highly manual and relationship-driven. Customers must believe in the people as much as the product.
Can relationship-building be learned?
Absolutely. I’ve seen scientists/ technical founders transform into their company’s best salespeople once they realize they can’t delegate that role early on. They’re the most qualified to talk about the product and build trust.
