Minds Capital Podcast Skipping $2m EBITDA Deals ("The Messy Middle")
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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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.
Run The Exit Math First
- Do the math on equity creation before committing to lower-middle deals; small EBITDA growth often yields minimal carried interest.
- Recognize management fees and taxes will significantly shrink partner proceeds on $2M-level deals.
Multiple Bands Matter
- Multiples cluster by EBITDA bands: 0–2x, 2–5x, and 5x+.
- To capture multiple expansion you must push the company through a band, so entry around ~4–5 EBITDA is strategic.