Business Development · Business Strategy

Advice on running two companies at once?

Darren Naylor

February 9th, 2016

I've been running my first startup for a few years now but I've also had a second idea on the side for a while now that I won't be able to forgive myself for if I don't pursue. I'm at to the point where I've been taking several meetings with potential technical cofounders so that I can get a prototype up and running. The idea is validated, I have an awesome designer on board, and we have early adopters ready to test.

Now while that's all great and grand, I'm wondering if it will be possible in the future to be involved with both in some way or if it will require me to choose. I'm one of those over ambitious types that doesn't need much sleep, but I can see how this could become a challenge.

So I'm wondering if its best to fully choose one at some point? Step into an advisory role in one and focus on the other? Sell one and entirely focus on the other? Etc etc. 

Would love to hear if anyone has been in a similar situation and what the different outcomes have been.




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Simon Chatfield Owner at The Chatfield Group

February 9th, 2016

It's not going to be easy running two companies at once, I have done it. The success of each is going to be determined by how ready they are to be run by themselves or the team you have built. 

I would say that if you can successfully be 'away from the office', whatever that term may mean for your business, for an extended period 2+ weeks where you be assured that the wheels won't fall off and/or you wont come back to a heap of problems then you're probably ready to take on new challenges. If you don't have the proper people or processes in place and it would scare you to be away for that long then the company isn't ready for your divided time.

Good luck.

Darrel Raynor Project & Ops Turnarounds, Interim CIO/COO, improve performance of dept or teams. Speaker, Trainer, Consultant, Staffing

February 10th, 2016

Let's hit this from an Ops tuning perspective... I do company turnarounds and start-up processes, hiring, and anything that does not require the big vision or heavy tech expertise. These usually start out full-time, then trickle down, as planned, to nada. So once you have the processes set and have taken the big actions, you should be able to run two firms at once.

Here are a few tips:
1. Do not share employees/founders between the two.
2. Do share vendors/outsource between the two.
What this means is keep your people focused on what they do for that one firm. Seek to use shared vendors for HR, marketing, advertising, and anything else that is not core to your business. You will save much time working with the same people.

Set recurring meetings with your various teams at each firm so that they all feel they are getting your dedicated attention. Have each Team or person setup a spreadsheet or some type of todo/project system entry that you and them jointly manage. We use Asana but even a Google spreadsheet will do. Have them (and you) put all topics each of you want to talk about when you meet, yes, this is a rolling agenda. Simple and complex questions go here... If you (or they) can answer a question, just do it in the file, no talking needed... The complex issues, people issues, strategizing, etc. can be done in person. Insist everyone write down their questions and other topics. Do not be immediately available except for real emergencies. 

Ping me for more. This is not too much different than managing say, a tech team in Austin and an Ops team in Philly :)

Joshua Kundert Virtual Assistant

February 10th, 2016

Why not consider bring on an assistant, someone virtual that you could decide tasks that you want to delegate out to free up some of your time. That way  business one will be taken care of in part and you could also have the virtual assistant help with getting the 2nd business going.

Eric Sullivan CEO at FoundationLab

February 10th, 2016

I think there are a few things to consider. One option would be to train up someone to take over your current business so you can invest time into the new one. Obviously there are a lot of factors with compensation/equity that could come into play here to entice someone.

The other thing to consider is that down the line if you do take on investment for either of the ideas if you haven't already that investors are going to want your undivided focus. So if that is on your radar something else to think of.

Darren Naylor

February 10th, 2016

Thank you all for your input, it's greatly appreciated.

I think hiring remotely for ops in my current company will be what allows me to do both. I'll be able to oversee and help when needed, but won't have to be involved in the regular time consuming day to day tasks. 

I feel like it's sort've a jump to see if I fly time for me, so it's bought on a good amount of thought and anxiety. But hell, that's what we're here for, right?

Darrel: I'll pm you separately with a few questions.

Thanks again, guys.