What I wish someone told me before I started a second business
I wish someone had told me that the hard part is not finding time for the second business. It is that the first business does not pause just because you are distracted. Problems there do not wait politely while you are heads down on something new.
What actually made the second business survivable was making the first one boring, in a good way. Documented processes, a team that did not need me for every decision, clear ownership. Only once that existed did adding something new become possible without everything falling over.
If you are thinking about starting something new while already running a business, that is the one thing I would tell you to fix first.
Making the first business 'boring in a good way' is underrated advice. I tried to run two things in parallel before the first one had solid processes, and the result was both things running at about 60%. Documented processes and a team that doesn't need you for every decision sounds like an operational goal but it's actually a prerequisite for any kind of growth. The interesting question is how you knew the first business was actually ready — was there a specific threshold you hit (revenue, headcount, systems maturity) or was it more of a gut call?
Honestly more of a gut call than a clean number, though a few signals lined up. Revenue had flattened rather than dropped when I stopped micromanaging it, which told me the business could hold steady without me in every decision. The bigger tell was that my team started solving problems before I even heard about them, and when I checked in I was usually the last to know rather than the first. Headcount and revenue mattered less than whether people were making calls I would have made anyway. Once that was true most of the time, I figured the downside of starting something new was manageable.