I spoke with a number of multi-business entrepreneurs.
This is what I learned.


Over the years, I’ve been lucky enough to spend a good amount of time with a good number of entrepreneurs. What a crazy bunch. A particular breed are those who run multiple businesses at once – and manage to stay (seemingly) sane too. These fine men and women come in all shapes and ages; some dominating several industries as others having built an empire on the back of their personalities.

You’ve heard about them. You might even be one yourself. As technology has lowered entry-barriers and given leverage to anyone willing to learn, a high school-student today could easily task out the work equivalent of a dozen companies just a few decades back. While our tools are sharper, running multiple businesses itself isn’t anything new. From Steve Jobs (Apple, Pixar) to Elon Musk (SpaceX, Tesla, The Boring Company) and Jeff Bezos (Amazon, Blue Origin) to Jack Dorsey (Twitter, Square); they’ve all been in the headlines sharing their experience on running multiple sizeable businesses. 

“I wouldn’t recommend running two companies”  is what Musk has famously said, only to find himself launching The Boring Company just a few years later. So what is it that keeps multi-business entrepreneurs hungry and motivated doing what they do? And how do they do it? 


26% of entrepreneurs juggle more than one business

While statistically, one out of every four entrepreneurs is juggling multiple businesses, in reality the distribution varies drastically across age and region. Operating two or more businesses simultaneously seems to be more common in younger age groups. Specifically 47% of under-30’s and 35% of age 30-39, compared to those over 60’s (15%). However, looking at larger datasets across 50 economies and all continents, we find that the youngest age groups are actually less likely to be starting their own businesses. Something that often gets buried under all the startup glory and exponential opportunities bonanza.

Therefore, much more important than age, enabling factors play a huge role in whether or not someone decides to dip their toes in the startup ocean: availability to financing, social and cultural factors, alternative job opportunities and access to social security, just to name a few. 


“If you chase 2 rabbits at once, you’ll end up getting none.”
– Russian proverb

Now, don’t get me wrong. I’m fully aware of the conflicting schools of thoughts surrounding this topic and have been a curious observer of this myself. Anyone who has ever so much as tried to found their own business knows how much commitment, tenacity, patience and perseverance just making things work in one company can take, not to mention two or more at the same time.

On the other side of the table, the more optimistic ones would see the opportunities in running multiple businesses. Scaling already built networks and channeling ambition into figuring things out; ability to put their various talents and interests into good use and the pure delight of learning.

But this article isn’t about arguing whether or not juggling multiple businesses is a good idea. It’s about sharing experience from those who’ve already done and actively do it today. The founders I’ve spoken to, who shall remain nameless, all own, control and operate (i.e. have an active executive role) two or more businesses across a wide range of industries and locations. 

This is what I’ve learned.  


It’s not glamorous

This title earns its spot as #1 simply because most entrepreneurs who operate multiple businesses fly under the radar. This is not to say their companies or offerings aren’t visible on the market, but they’re not your high-flying-in-the-headlines-type of brands on a mission to disrupt 10 industries and save-the-planet-kind of businesses. 

Quite contrary in fact, if you’d single out just one of their companies, it wouldn’t necessarily look like much. They’d be profitable, small-medium sized businesses operating in a specific market serving a specific type of audience. But when you combine them all together, suddenly you have a multi-million dollar portfolio of diversified assets owned and controlled directly by you. 


Share the load 

“I could never do it if it was just me.” 

Easy #2. Not one multi-business entrepreneur I’ve spoken to has said anything else but this. A clear indicator of the level of interdependence and trust placed on their teams. One founder running four businesses in four different industries tells me they split the load between his co-founder, each being in charge of two companies, both strategically responsible for all four. Another person managed three companies all by himself for two years, and to “save [his] marriage, family life and sanity”, finally hired managing directors to take care of the separate entities. 

While the importance of partnering up has been echoed over and over again, I’d be lying to say I don’t regularly also hear the opposite. ‘Don’t partner up if you don’t absolutely have to’ are pretty close to the exact words I frequently hear experience-shared by entrepreneurs. Although never in the context of operating multiple businesses. While people problems do top the list of reasons why especially early-stage startups fail, in the case of running multiple companies, sharing the responsibility and credit in this case has shown itself as a clear asset. 


“Eat your frog in the morning” 

Literally what I was told.

Translation: do whatever is most critical to achieve your goals first thing in the morning. It’s not always the easiest or most fun, but the most critical. Everything else is nonsense. Choose the battle worth your fight. 

And of course, the operative keyword here is ‘choose’. 

Entrepreneurs face a gazillion challenges on a daily basis. From client to cash and staff to bureaucracy, there’s always a conflict of priority and some crazy fire waiting to be put out. Therefore, the ability to consistently choose what’s critical over what’s seemingly urgent over time is something I find to be true throughout my own experiences as well. And as the former U.S president D. Eisenhower famously said “what is important is seldom urgent and what is urgent is seldom important”, entrepreneurs managing multiple businesses shall follow suit by choosing to work on their business, not necessarily in their business.  


Don’t rely on a single revenue stream 

In other words, diversify. This one is particularly interesting because in legacy business models a company’s value proposition typically relies on a single point of sell. And the rest is tweaking, optimizing and maximizing the profit margins of that.

These multi-business owners however swear in the name of building multiple sources of income and company revenue streams, with one saying seven streams is the average you want to be looking for. 

One founder who’s built their personal brand across sectors (professional athlete, academics, VC-backed tech startup, advisor to governments and best-selling author) manages these sectors in parallel while traveling the world. While seemingly unrelated fields, the combination of these arm him with a versatile set of knowledge that have helped him leverage uniqueness and competitive advantage in each area. While this person has followed his passion and made strong pivots from one domain to the next, another person (5 companies: manufacturing, hospitality resort, interior business, investment fund and a food/beverage company) let opportunities do the talking and simply followed the market. Identifying what was trending globally and localizing wherever the waves were already moving. 

My takeaways? Do find your personal interests but align them with real market needs. Understand macrotrends yet localize your offer. Don’t be afraid to diversify across industries, markets or sectors. 


Batch things up

Regardless of how different or diversified your businesses are, they will likely share the same functions: accounting, HR, compliance, administrative work and so on. Centralizing these necessities and batching up tasks can save what could easily lead to a loss of… I don’t know, say, a good portion of mental health, resources and time.

The founders I spoke to all batch up something. One’s personal assistant is the same person in all his businesses, making it easier to strategize schedules and logistics in a more holistic way. Another founder has synchronized the accounting and legal work of his two companies to one team. You’d be surprised how many entrepreneurs I know literally move with their offices, relocating their homes no further than a few minutes walk door-to-door from work. Jack Dorsey, the CEO of Twitter and Square, does this too. He juggles his day by spending his mornings at Twitter and afternoons at Square, batching both company locations to be across the street from each other. 


Asynchronous maturity levels

“If you’re operational in multiple companies, make sure your businesses are on a different stage from one another. Don’t launch your second business before your first one is stable. Look, there’s a huge difference between raising 3 children a few years apart versus having triplets today.” 

This one is hard to argue against. If you look into these multi-business entrepreneurs’ history books, you’ll see a clear chronological order of which came first and how things evolved from there. But as things rarely go as planned, it’s important to stay agile. One founder I spoke with started his first business (food & beverage) ten years ago only to realize that the work they outsourced for designers and website builders wasn’t the quality he was willing to pay for. To save money, he started to learn coding and design himself. Fast forward to today, and he now runs a global IT company servicing big brands from tech production to digital strategy – alongside his original brand, now a chain of restaurants. Building the second business was only possible due to his first one being already operationally stable at the time. 

Remember Airbed & Breakfast?

More famously, Airbnb temporarily launched another business before evolving into the full ecosystem it is today. What many tend to forget is back in 2008, its founders Nathan Blecharczyk, Joe Gebbia and Brian Chesky had run out of money. Out of desperation, they started packing the cheapest cereal in supermarkets into self-designed boxes priced 40$/piece in an effort to fund their original idea (letting people sleep on other people’s air mattresses) that was now dying.

The cereal was never supposed to be the main business but the boxes were sold out in days and made more money than Airbed & Breakfast ever had. As bizarre as it sounds, the founders got attention by shipping boxes to tech journalists. And the press ate it up. They even got selected by Y Combinator despite their unsuccessful interview by literally handing a box of cereal to Y Comb founder who awkwardly thanked them yet listened through their cereal story – and the rest is history. 


Ground yourself to one thing, every single day 

I learned this from an entrepreneur with 2 businesses while traveling on average 320 days a year. 320 days. Consecutively for the past 10 years. I’m amazed he even managed to find the time to sit down and have lunch with me. 

He schedules his calendar roughly one year ahead of the time; coordinates his travel plans according to time zones so he can avoid the worst jet lag and hit the most important meetings and conferences. And he travels together with his life partner wherever he goes. When asked about his ability to sustain this lifestyle, his answer is simple: 

“You need to be religious about one thing a day, every single day. What I do is a 60-minute sports window at the same time. Everyday. No matter the time zone or the physical location. Never compromise on that one thing, whatever it is in your life.” 

Curiously, Elon Musk might just agree. One of the most upvoted questions during Reddit AMA (Ask Me Anything), Musk was asked “what daily habit do you believe has the largest positive impact on your life?” 

To which Musk simply answered: “Showering”.

In all seriousness, designing what otherwise may slide into ‘one big blur’ around one particular window a day does more than just ground you. It sets your entire daily rhythm around it from eating to sleeping, especially if it’s physically demanding. It can also serve as personal space. In different versions, I’ve heard this being manifested as meditation hour, eating one meal a day, training with musical instruments or something as simple as taking a walk around the block. 


Final thoughts 

Perhaps one of the more arresting thoughts I’ve gained from these conversations is that there doesn’t seem to be a clear logic to why someone is managing multiple businesses. I’m not even sure it would be entirely fair trying to rationalize this as it seems more like an evolution of life rather a deliberately planned career path. 

Therefore, rather than asking ‘why’, perhaps a better version in this case would be asking ‘why not?’ because the one thing that shines through is the unmatched level of ambition and optimism from these people. 

So much so, in fact, that the ability to build, learn and apply a broad range of skills and interests into real problems is likely to be the real purpose. And that itself is inspiring.

The hustle is the journey and the journey itself is both the prize and price.

At this level of determination of simply ‘making stuff work’, it’s hardly driven by financial incentives or anything material. To many, it seems nothing less than a full identity.

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Identifying as a multi-hustling entrepreneur yourself? Technology does help. Learn more about Smart Companies and how they might just make your life a tad easier. And as always, feel free to drop us a line, comment, feedback or thoughts at future@korporatio.com