It's Portfolio Harvest Season

The Clock Is Ticking: Are You Ready

With 11 months to go in 2025, do you have clear visibility into your portfolio companies' trajectories? Will they need more capital to sustain growth, or is it time to consider an exit or strategic acquisition? And for your own firm—if you’re managing outside capital—what actions are you taking today to improve your TVPI, DPI, and MOIC?

These questions aren’t just hypothetical—they’re the difference between outperforming in a competitive market and falling behind. I’ve seen firsthand how quickly things can change and how crucial it is to stay ahead of the curve.

After more than 25 years advising the world’s largest financial institutions, I launched my venture fund, ready to dive into FinTech and InsurTech investments in 2019. But then the world shifted. COVID didn’t just disrupt the markets—it forced a complete rethink of strategy. By 2020, I pivoted to the sell-side, obtaining my investment banking license, and refocused on M&A and growth capital for scale-ups with enterprise values between $20M-$250M. I also started working closely with emerging managers navigating capital raising in an increasingly saturated market.

The lessons I’ve learned from these transitions are what I’m here to share—because in venture, timing and strategy are everything.

Are You Positioned to Win?

Managing a venture portfolio is like navigating an ever-changing landscape. Some companies are thriving, others are treading water, and a few might be quietly burning through runway without clear direction. This is where portfolio harvesting becomes critical. It’s not just about identifying winners—it’s about knowing when to double down, when to step back, and when to push for a strategic exit.

Even as a minority investor, your influence matters. The FinTech and InsurTech venture spaces are oversaturated. New funds are launching, but only those that can demonstrate real, tangible returns will secure the trust and capital of LPs. Don’t sit on the sidelines and wait for something to happen.

The Pressure Is Real: What Sets You Apart?

Here’s the hard truth: It’s not enough to have promising portfolio companies. LPs are increasingly focused on outcomes. They want to see how you’re improving TVPI (Total Value to Paid-In), DPI (Distributions to Paid-In), and MOIC (Multiple on Invested Capital). They want to see realized exits and tangible evidence of your strategic impact.

It’s been over 30 days since the 2024 books closed. By now, you should have a clear view of which companies need additional capital, which are primed for acquisition, and which might be better off exiting now rather than burning more resources.

Now is the time to take a hard look at your VC’s internal strategy, your portfolio’s trajectory, and your pipeline for the rest of 2025. Are you positioned to deliver the results your LPs expect?

What I’ve Learned as an Investment Banker

Over the years, I’ve observed patterns that separate top-performing venture firms from the rest. Success doesn’t come from passive management; it comes from being deeply engaged and willing to make bold, strategic moves.

I’ve seen firms hesitate to exit, clinging to potential that never materialized, and I’ve watched others capitalize on momentum, securing early exits that exceeded expectations. I’ve learned that exit timing is everything, and that being proactive—rather than reactive—is what turns good funds into great ones. You can also cash some chips, and do a secondary sale on your positions.

The most successful venture leaders aren’t just investors—they’re strategists, constantly recalibrating to align with shifting market dynamics and capitalizing on opportunities as they arise.

Let’s Reconnect

I’m launching this newsletter to reconnect with my network and offer actionable insights from the trenches. Whether you’re looking to scale your portfolio companies, prepare for strategic exits, or optimize your fund’s performance, I’m here to help.

The next 11 months could define your year—let’s make sure you’re positioned to win.

Tom C. Schapira
Founder and CEO
Imagine Capital Group
E: [email protected]
Website: http://www.imaginecapitalgroup.com

Securities Offered through Wellesley Hills Securities. Member FINRA/SIPC