Does having multiple owners cause broken deals?

I've lost a deal because the headline number sounded great until one of the owners realized that splitting the proceeds in two left him a little short of retirement. You definitely ant to understand their individual goals and outcomes post deal. In the same deal, one of the owners was ready to retire as he was 10 years older than the other. The other started questioning what he'd be doing with the rest of his days besides dropping the kids off at school. I'd spend a lot of time speaking with them individually, instead of together, if I had to do it all over again.

I agree with the above comments that it adds complexity and some level of transaction risk. As others have stated, you can mitigate this with good communication, e.g., including all three signatures on the LOI, asking about motivations for each, developing 1:1 relationships. Another consideration is how active each of the three are in the business. If having three sellers means you need to backfill three roles instead of just one, you should consider that in your transition plan.