Deal Principle
Simplicity Wins
Complex deals rarely close smoothly. Every moving part is a potential failure point. The simplest path from deal to execution is almost always the best one.
Why Complexity Kills Deals
Every added layer of complexity — a third party condition, a contingency that depends on another contingency, a funding structure with five moving parts — is a new way for the deal to fall apart. And deals fall apart all the time.
First-time investors often overcomplicate things in an attempt to be creative or optimize every variable. Experienced investors have learned that the deal structure that gets to closing is better than the theoretically perfect one that never closes.
What Simplicity Looks Like in Practice
One lender, not three
Layering hard money + seller financing + gap funding sounds clever until one piece falls out and the whole thing collapses. Where possible, use one primary funding source.
Clean purchase agreements
Excessive contingencies signal a weak buyer. A clean offer with fewer contingencies often wins even at a lower price — and closes faster.
Defined exit before entry
Know exactly how you're getting out before you go in. Ambiguous exits create pressure and bad decisions mid-deal.
Fewer partners
More partners means more decision points, more opinions, and slower execution. Two people with clear roles beat five people with shared responsibility.
The Right Complexity Question
This isn't about avoiding all complexity — some deals require it. The question is: is this complexity adding real value, or is it solving a problem we created by not thinking clearly about the deal?
When I look at a deal structure, I'm asking: what's the simplest version of this that still works? Can we remove a condition, consolidate funding sources, or clarify the exit to make this more executable? Most of the time, the answer is yes.
If you've got a deal that's getting complicated, send it to me. Sometimes a fresh set of eyes can find a simpler path through.