“3 things I wish I knew if I was starting my HoldCo from scratch”
Have your first company need as little to no inventory as possible. Inventory is the most difficult asset to manage. It consumes cash. Inventory-light businesses are more consistent cash flow producers, and you need that cash flow to pay down debt and buy your next business.
Do not take on too much debt. Debt allows you to buy a lot more company today than you otherwise could. Some debt is OK. But too much debt will lead to lots of future cash flows being designated for repayment and an easier-to-kill business in the meantime.
Be careful how you negotiate any debt. We initially took a 5-year bullet payment loan with signed personal guarantees. I always say we were more lucky than good in the beginning. Things could have gone very differently on our first acquisition, and we would have been finished before we started.