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Why All Entrepreneurs Should Consider Starting Another Company

September 18

9 min. to read

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Even if you are on the top of the world there is always more beyond.

As evidenced by CEOs, presidents, c-level executives, creatives, and especially entrepreneurs across the professional world, a key ingredient for success is restlessness

Restless entrepreneurs stay sharp. They push themselves to explore new fields, experience new industries, and try new managerial approaches – all in the pursuit of bettering themselves and their teams. They’re always working to improve. 

Entrepreneurs do this in a variety of ways.

One of the most common way is starting a second company. 

This may seem counterintuitive, but when your first company or project is hitting its stride, that’s the best time to consider your next move. The hard work is done  you’ve made it through the early-hustle stages, you’re reaping the rewards, life is a bit less hectic. To stay still now would be to stagnate. 

I’ve experienced this first hand. 

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After my first company, Skylum, started to gain serious momentum, several of my partners branched off into new projects. One opened a bar-restaurant, another formed a band. In time, I recognized: they were all searching for a way to stay restless. 

Personally, I’d long dreamt of creating a new product – I called it Photolemur – but I’d hesitated, mostly because the idea didn’t fit neatly into what we were already doing at Skylum. It demanded a new team, potential VC funding, new strategies—and I didn’t want to distract from, or damage, Skylum’s brand.

The more I thought about Photolemur, however, and the more excited I became about the idea, I realized that it could stand alone as a separate company—and that it probably should. I decided to give it a try.

Looking back, building two companies at the same time was ambitious. But the experience was invaluable.

It made me a stronger CEO. It made me a stronger communicator. And it taught me certain things about how to manage two large, ambitious projects at once.

Here are the lessons that proved most important. 

Tangibly separate your time for each company. 

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Countless studies agree: multitasking is inefficient. 

That means instead of trying to run two companies literally at the same time, it’s better to create a system that forces you to divide your time. When I was building Photolemur, I would designate specific days to focus purely on Photolemur tasks. Fridays, for example, were typically my Photolemur days. As best I could, I wouldn’t work on tasks related to Skylum on those days. (But in blocks of time I reserved for Skylum projects, Skylum commanded my attention.) 

It wasn’t easy—but no goals worth pursuing are. 

Strictly planning and managing my time was the only way I could get things to work.

When I didn’t, everything became a mess. I imagine it’s like this for everyone. You can’t be in two places at once. You have to give yourself completely to one team, then shift gears to the next.

It’s tough, but when running any company that’s growing fast, managing your time won’t be your biggest problem.

You’ll have to divide resources, too. 

This is, in fact, a key challenge. Running two companies amounts, essentially, to leading, managing, and supplying double the amount of teams and people as you had to before. You have to ensure every employee on both sides of the new equation has the support, attention, and compensation they need to be effective.

The key to this is cautious planning and purposeful budgeting

It’s hard, but it’s possible.

Photolemur hit $1 million in revenue in what felt like a blink of an eye––and we made that happen without taking any resources from Skylum. 

You can’t do that if you’re not allocating your resources properly. 

You need teams you can rely on. 

The improper allocation of resources, of course, has another side effect: it can poison the production of your teams. 

Uncompetitive compensation, for example, drains motivation. And unmotivated teams are, most of the time, ineffective teams. Simply put, you won’t be able to run two companies without effective teams. 

Or, at least, I wouldn’t have been able to do it. I had remarkably dependable people around me. They meant I didn’t have to be as involved in any given process on a daily basis. I could trust that they would keep their respective engines running. That was critical – and worth investing in.

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But with your teams you also need to be transparent.

In managing my disparate teams at Photolemur and Skylum, I found right away that transparency was paramount. It was always better to be over-communicative. Sure, sometimes I’d find myself explaining new processes, structures, and systems five or seven times, but it was worth the effort because it fostered trust. 

Admittedly, it was a bit easier in my case, because I was able to house Photolemur and Skylum in the same shared office, which allowed Photolemur to maintain a certain intimacy with Skylum. That made the old employees feel as if they were still in the loop. At the same time, a shared office let me provide the kind of attention and care that my new teams needed.

Overall, although imbued with challenges, starting a second business will allow you to take risks, grow as a person, and will supercharge your personal development.

Starting a second company forces you to push your personal envelope in ways you never can with your first. I know it allowed me, at least, a new kind of creative freedom, as well.

And it was thrilling—at Photolemur, we would experiment and pursue projects and goals that were simply too risky for Skylum. 

Plus, it might pay off in more ways than one—Photolemur and Skylum have now joined forces, making us a more powerful, efficient, diverse company on the whole.

Once you’ve fought and bled to make your first company a success, it’s tempting to rest on your laurels and stop trying to develop. But those that really want the most from their business, from their career, and from themselves will push to work harder, to keep growing – to keep creating

Written by

Alex Tsepko

CEO of Skylum, Co-Founder of Photolemur

Alex is the CEO of Skylum, a passionate photographer, an AI fanboy, a family man, and a LEGO builder. Alex learns from everyday life and gets inspiration from people he meets while traveling the globe. Together with 130 incredibly talented humans, Alex is building Skylum — a next-generation global photography company for a new generation. And they’re having the time of their lives!

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