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Running Two Companies: 6 Questions to Ask Yourself Before Taking Up the Challenge

In this guest article, entrepreneur and dual-CEO Misha Rudominski offers his expert advice on running two companies at the same time.


“Don’t run two companies at the same time.” Those discouraging words from Elon Musk were the only words I could think of after I got the offer to lead my second company. “Just don’t do it,” he said.

But if I’ve learned one thing as a CEO, it’s to trust your gut and follow your personal sense of drive. So I did the exact opposite of what Elon recommended. Now I’m the CEO of two companies: nect WORLD, a startup changing approach to personal connectivity among professionals, and Space Logistics Ukraine, a company providing on-demand launches of pico-satellites and joining SpaceX in the mission to make space closer and more affordable. It’s certainly a challenge, but do I regret it? Not for a minute.

As an entrepreneur, you’re probably attracted to tackling big challenges in the world. And sometimes one project isn’t enough. If you find yourself weighing the possibility of leading two businesses, here are some things to consider before joining the dual-CEO club.

1. What’s your drive?

There’s no denying that achieving success, whatever the challenge, is deeply satisfying. But the hard truth is that ‘achieving success’ in itself is not a suitable drive in business. And it certainly won’t take you very far if it’s solely what motivates you to run two businesses.

Why? Success is an end goal. Success is something looming on the horizon, and when you reach it, you see new horizons ahead. If you are not excited about the journey of taking your product to market (read, the day-to-day activities of making your product viable), it will be overwhelming and simply not worthwhile.

While developing the nect MODEM, for example, I never got tired of working on the product itself, even when we didn’t get the results we expected. I knew we were rethinking the way people connect to the internet, and the journey itself was exciting.

Similarly, my passion for space and engineering means I’ll never get bored of my work at Space Logistics Ukraine. The work is just too fascinating. It was true in 6th grade when I started attending a modeling class; it was true at the University of British Columbia during my Mars Colony project; and it’ll be true as CEO of Space Logistics Ukraine. Are there challenges along the way? Of course. But it will never feel like work to me.

My advice is to only take up a dual-CEO role if both of the projects equally inspire you to push yourself beyond your limits.

2. What stages are the projects in?

There is a big difference between running two businesses and running two startups. The early stages of a startup might require your exclusive involvement and much strategic decision making. You also need to take time to find a reliable team that you may further rely on.

Serial entrepreneurs Elon Musk and Jack Dorsey are great examples. While they successfully run two companies now, their projects didn’t start simultaneously: Musk launched SpaceX in 2002 and joined Tesla in 2004; Dorsey founded Twitter in 2006 and Square in 2009.

The company I am invited to lead is now at the stage nect MODEM was a year ago. While this project still requires much of the CEO’s attention, there is more clarity and less stress in growing it. The bottom line is: you have a better chance of succeeding in dual CEO roles if at least one of the projects has already reached relative stability.

3. What have you achieved so far?

This question might sound like a job interview. And you better take it that way! Try to be skeptical of your own abilities (if your inner imposter voice is not already doing it for you), and give yourself arguments to prove that you can bring value to both companies you’ll run.

  • Have you developed a good understanding of the given product or niche?
  • Have you managed to prove any business?
  • Have you assembled a talented, engaged team and established processes that led them to work effectively together?
  • Have you ever leveraged your professional network to build support for a project?

Making a list of your achievements will help you regain confidence and focus on your core strengths and the ways to apply them in new business. At the same time, it’s an opportunity to be frank with yourself — if you don’t have achievements in the core areas of a CEO, maybe it’s better to postpone the decision and focus on one company at a time.

4. What’s your leadership style?

When it comes to running more than one company, it is not only about how many companies you manage, but about how you manage the teams.

You can adopt a laissez-faire approach when running several companies at the same time, at least for a while, but your businesses will need deep involvement and leadership at some point or eventually they will go off the rails.

Visionaries who lead by setting the destinations and communicating the goals might be the best candidates to a dual-CEO club. At the same time, the experience of running two companies will unlikely be rewarding if you have a coaching or affiliative leadership style that requires a lot of time and mental presence. Thus, know yourself and apply your strengths where they fit best.

5. Can you set priorities?

Prioritization is defined as deciding on the relative importance and urgency of your tasks at hand. The unspoken part of prioritization is how you deliver on your commitments. When you juggle two or more businesses, doing this becomes a dual challenge. And I know what it means, as I have combined launching my startup and being part of an accelerator with studies at the university.

You cannot be immersed in both companies’ work full time, all the time, so you need to know how to cut your involvement to the necessary minimum. The ability to set priorities lets you be there to take the most urgent and strategic decisions. This is the essential quality for anyone embarking on the dual-CEO journey.

6. Are you resilient to stress?

Assuming responsibility for decisions when the whole business is on your shoulders is stressful. This is true for one business. This is more than doubly true for two.

How do you get around this? I personally always concentrate on one issue at the time. For me, multitasking is not effective and multiplies stress and fatigue, and recent research shows I’m not the only one. If any situation or discussion turns overwhelming, I take a break for a short stay-alone moment. Because it’s not about how resilient you should seam, it is about your ability to maintain full control of yourself and the situation.

Another strategy I use is intentionally training myself to be more pessimistic. In fact, optimism — sometimes not-so-optimistically called one of the ills of modern society — can be at odds with achieving your goals. Instead, it’s much more practical to anticipate obstacles and proofs of Murphy’s law than get discouraged and stressed out by something that went not as expected.

Are you prone to this kind of thinking, or are you easily discouraged when the outlook suddenly turns less than rosy? If any unexpected obstacle or decision makes you stressed, and you have not developed reliable coping strategies, running two companies is probably not for you.

The Bottom Line

Running two companies is not something to take on simply for the sake of increased revenue or an additional title. It’s something to embark on only when your passion for the project just won’t let you say “no” and because you know you can bring value to it. If these are true for you, I, a dual CEO, will be glad to welcome you to the club.

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