Minds Capital Podcast Skipping $2m EBITDA Deals ("The Messy Middle")
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Dec 17, 2025 Dan Tamkin, co-founder of Resurgent Capital Partners, is a turnaround investor with a tech-savvy background. He discusses why the lower-middle market offers better value creation than failed VC ventures. Dan emphasizes avoiding $2M EBITDA deals, which often yield poor economics and founder frustration. He highlights the strategic focus on acquiring small businesses outright or pursuing larger deals and reveals insights on managing technical debt as an asset. His experience with the Sonent turnaround showcases the importance of emotional intelligence in dealmaking.
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Why Fallen Venture Assets Disappoint
- Venture 'fallen' assets are often hard to convert into real equity value because hope keeps VCs from marking them down.
- Turning a venture asset into a cash-flowing PE-style business frequently fails to create meaningful enterprise value.
First Deal: Freight Brokerage Turnaround
- Their first platform was a freight brokerage with high customer concentration that survived Midwest flooding.
- They flipped it during COVID for a market multiple, delivering a 52% IRR and early credibility.
Avoid The Messy Middle
- Avoid the 'messy middle' of deals that are too small to create meaningful carry and too large to DIY.
- Target either small deals you can own outright or bigger deals that produce multiple expansion above ~5x EBITDA.