I run six businesses under Linkedd LLC. Not six ideas, not six side projects gathering dust — six businesses that are live, taking customers, and need something from me most days. People ask me fairly often how that's even possible, usually assuming there's some secret system or a team behind the curtain. There isn't. It's just me, and the honest answer is less about a system and more about giving up on some assumptions that work fine with one business and break the moment you have more than one.

Most business advice assumes you only have one business

Nearly everything you read about running a business — focus on your niche, know your customer inside and out, obsess over one product — is written for someone with one thing to run. That advice isn't wrong, it's just scoped to a world I don't live in anymore. When you have multiple businesses, "focus" doesn't mean picking the one true priority and ignoring everything else. It means figuring out, every single day, which fire actually needs you today and which one can wait until tomorrow without anything breaking.

I learned this the hard way in the first few months after starting my second business. I kept trying to apply single-business thinking — carve out a full day for Business A, then a full day for Business B — and it fell apart almost immediately, because businesses don't take turns being on fire. A client email needs answering today whether or not it's "Business A's day."

The real constraint is attention, not ideas

Everyone assumes the hard part of running multiple businesses is coming up with the ideas or getting each one off the ground. It's not. Ideas are cheap. What's actually scarce is my attention, and specifically my undistracted attention — the kind where I can think clearly about a real decision instead of just reacting to whatever's loudest.

Once you accept that attention is the bottleneck, a lot of decisions get simpler. You stop asking "should I start this seventh business" and start asking "do I have enough spare attention to give this the minimum it needs to survive." Most of the time, honestly, the answer is no — and that's fine. A business that isn't getting attention doesn't grow. It doesn't even hold steady. It quietly rots, and you don't notice until a customer complains or the revenue dips and you go look and realize you haven't touched that business in three weeks.

Every new business starts back at zero — no matter how many you've launched

This one surprised me more than it should have. I assumed that by my fourth or fifth business, I'd have some kind of shortcut — that experience would compress the timeline. It compresses some of it. I'm faster at the mechanical stuff: setting up the LLC, getting a site live, wiring up payments. What experience does not compress is the part where a brand-new business needs consistent, patient attention before it has any momentum of its own. That part takes as long as it takes, every time. There's no veteran discount on the early grind.

What I've gotten better at is recognizing that phase for what it is and budgeting for it honestly, instead of assuming this time will be different because I've done it before.

How I decide what gets worked on today

I don't run a rigid schedule that assigns fixed hours to each business — I tried that and it broke constantly, which I get into in more detail in how I actually split my day across six businesses. Instead I run a simple daily triage, and it comes down to three questions, roughly in this order:

  • Is something actually broken right now? A customer issue, a payment failure, something that's actively costing money or trust. This wins every time, no matter which business it's in.
  • Is there a decision only I can make that's blocking progress? If a business is stuck waiting on me to approve, decide, or unblock something, that jumps ahead of work that's just "nice to make progress on."
  • Which business has gone the longest without real attention? If nothing's on fire and nothing's blocked, I default to whichever business has been quietly neglected the longest, because neglect compounds and I'd rather touch six things lightly than one thing deeply and let the rest slide for two weeks.

That's it. It's not glamorous, and it's definitely not a productivity system you could put on a slide. But it's honest about what actually happens when you have more demands on your time than time to give them.

A simple framework for prioritizing across ventures

If I had to boil it down further, I think about each business on two axes: how much attention does it need right now to not lose ground, and how much attention would it reward if I gave it more. A mature business with steady customers often needs surprisingly little — just enough to keep the lights on and catch problems early. A brand-new business is the opposite: it needs a lot and will keep needing a lot until it has its own gravity. The mistake I made early on was treating all six businesses as equally attention-hungry, which meant the mature ones got attention they didn't need at the expense of the new ones that did.

None of this makes running multiple businesses easy. It's genuinely harder than running one, and I'd tell anyone considering it to go in with clear eyes about that — which is a big part of why I put together a full guide on how I actually run six businesses solo, walking through the systems, the mistakes, and the honest tradeoffs in a lot more detail than a blog post allows. If you want the ongoing version of this — what I'm actually doing week to week, not just the theory — the membership is where I post that.

If you're weighing whether to add a second business at all, I wrote a whole piece on that specific question: should you start a second business. And you can always see everything I'm building at Linkedd LLC.

Frequently asked questions

What's the biggest mistake people make when they try to run multiple businesses?

Applying single-business thinking to a multi-business schedule — trying to carve out a full dedicated day for each business instead of triaging based on what's actually urgent or broken that day. Businesses don't take turns being on fire, so a rigid schedule breaks almost immediately.

Is the hard part of running multiple businesses coming up with ideas?

No — ideas are cheap. The real constraint is undistracted attention. Once you accept attention as the bottleneck, the question shifts from "should I start this next business" to "do I have enough spare attention to give it what it needs to survive."

Does experience make each new business easier to start?

It compresses the mechanical setup — forming the LLC, getting a site live, wiring up payments — but it does not compress the amount of patient, consistent attention a brand-new business needs before it has its own momentum. That part takes as long as it takes every time.