Great Deals Get Killed by Bad Structure, Not Bad Numbers

Acquisition Collective

Learn how to raise capital, structure better deals, and avoid the hidden traps that kill most acquisitions.
In this episode, Judd Goodrich from MainShares breaks down how capital actually gets raised behind the scenes—and why most deals fail after the LOI.
From overpaying for solid businesses to ignoring post-close transition plans, this conversation is a crash course in what makes or breaks investor trust and deal success.
We talk about how to:
✅ Avoid overpaying—and why a 5x multiple is a deal killer
✅ Raise smarter capital with investor-aligned structures
✅ Stress test your returns with realistic EBITDA assumptions
✅ Navigate SBA vs. non-SBA financing (and why it matters)
✅ Build trust with investors through risk transparency
✅ Fix broken pro formats and unrealistic IRRs before it’s too late
✅ Create operator-aligned transitions that actually work
✅ Spot the governance terms that can destroy your cap table
If you're an entrepreneur, investor, or business buyer raising capital or structuring deals, this is a must-watch.
00:00 Who is Jordan and what is MainShares
02:00 Why good deals get rejected (hint: overpriced)
04:15 What investors really care about in a deal
06:30 When to involve your capital partner (LOI vs. post-LOI)
09:00 The 3-part framework: Management, Alignment, Structure
12:00 How bad debt structures ruin great deals
14:45 Why clean transitions win investor trust
17:30 Stop pricing off last year’s inflated EBITDA
20:00 Realistic IRRs and the truth about payback periods
24:00 How preferred equity and investor protections really work
28:00 Why most capital raises fall apart at the last mile
30:00 Governance red flags: dilution, veto power & more
34:00 Building a platform for transparency and investor confidence
38:00 Two types of capital raises: self-directed vs. brokered
41:00 The top reason deals get rejected on MainShares
45:00 Why structure (not spreadsheets) wins capital
47:30 What successful fundraisers do differently
50:00 The transition trap that kills most deals
53:00 Building trust with clear risks + mitigations
56:00 How overbidding destroys deals—and reputations
58:00 Final tips for founders raising capital the right way
→ Join our community - https://www.acquisitionscollective.biz/
→ Follow for more - @AcquisitionCollective
→ Instagram - https://www.instagram.com/acquisitioncollective/
→ TikTok - https://www.tiktok.com/@acquisitioncollective
→ LinkedIn - https://www.linkedin.com/company/acquisitions-collective
Follow Judd on
→ LinkedIn - https://www.linkedin.com/in/judd-goodrich
#Acquisitions #RaisingCapital #BusinessBuying #DealStructuring #InvestorTrust #IRRReality #BusinessFunding #Entrepreneurship #SMBAcquisitions #DueDiligence #BusinessValuation #SBAFunding #PrivateEquity #DealFlow #FounderJourney #FinanceTips #AcquisitionStrategy #BusinessPodcast #MainShares #ScalingSmart #BusinessOwnership #CapitalRaising #SmallBusinessFinance