Here’s How Serial Entrepreneurs Manage Multiple Startups

Your best chance of making it as an entrepreneur is to keep creating new opportunities for your various ventures to function in harmony.

Not-so-fun fact: For every startup that succeeds, another nine fail.

As an entrepreneur, you bet on yourself and your idea. If you’re a smart gambler, you know not to go all-in with the odds stacked against your success. Diversification is key; with all your eggs in one basket, you’re exposed to more risk.

While concentrating on a single business prevents you from becoming distracted or diluting your efforts, it also means relinquishing opportunities to build out complementary divisions or businesses to leverage your existing business.


Diversification is possible and profitable

Maybe your real dream is to create something even bigger with more impact: your own entrepreneurial empire.

Play the hand you’re dealt — and then some.


  • In just three years, Elon Musk started three companies. Nowadays, if someone asked what electric vehicles, solar-power systems, and space travel have in common, you’d probably reply: Elon Musk.

  • If you think Musk really needs to get a life, consider Richard Branson, who started more than 300 Virgin-branded companies — eight of them valued at $1 billion dollars.

  • Not to mention, Bill Gates “started Corbis while still at Microsoft as well as an investment company called Cascade Investment. Infact more than 50% of his wealth is from outside Microsoft.”

  • And Envato, “an Australian company, [run by a husband and wife team] not VC funded or anything runs Tuts+ network which is a tutorial service/website, about 10 freelance marketplaces…”


I’m not saying startup life is nothing but a numbers game, but I know firsthand that it never hurts to play the entrepreneurial field. When you are really small, you have to try different stuff to see what sticks.


Like Musk, I also started three very different businesses in my first couple of years. One took off, and I ditched the other two. Had I stayed focused on my first business and not been willing to try new things, I wouldn’t be anywhere close to where I am today.

For one thing, we never would have built one of our flagship programs and would have missed a huge untapped area of our market that is more interested in training and “do it yourself” than “done for you” services. These distinct businesses also grow symbiotically by generating leads for each other.


Double down in order to branch out

Getting one business off the ground is incredibly difficult. (Remember that whole “9 out of 10 businesses fail” thing?) Now, multiply that by however many businesses you plan to launch, and you’ve got yourself a recipe for a mental breakdown.

From a dude who’s been there, here are three tips for managing your various roles without folding on the first hand.


1. Don’t lose sight of the jackpot.

Remember your social life? Good, because it will likely only exist as a fond memory from here on out. But, stay with me — it’ll all be worth it.

The average business owner puts in an estimated 60 hours of work each week on one venture. If you pursue more than one, you’ll put in a lot more hours than that — but you don’t have to binge and do it all at once. You’ve got to compartmentalize the 24 hours in a day to keep your sanity intact.

If you’re a night owl, embrace it and work into the wee hours. If you have kids, you may even prefer that (just make sure to strictly enforce bedtime).

Weekends are also a golden opportunity to shoot the dice and see where your big ideas lead. Just be sure to apologize to your friends in advance for missing social engagements — startup-building on a guilty conscience is no fun.


2. Stack your deck.

While the safest hands are likely your own (you’re in charge for a reason, after all), you’ll never win without a strong team around you. Most important, you need a partner who can ante up and take responsibility for profit and loss while running day-to-day operations.

Ideally, your No. 2 can fill in where your own expertise is lacking. A great second-in-command contributes more substance and structure without challenging your leadership — much like Steve Balmer supported Bill Gates at Microsoft.

Over the past three or four months, I’ve put lot more responsibility into the hands of our leadership and management teams, as opposed to acting as a gatekeeper for everything.

Once revenue passes seven figures, you have to start giving up control and empower others to ensure the business continues to thrive — the onus is on you to make the calls that guide their efforts.


3. Know when to hedge your bets.

Most entrepreneurs are control freaks. But betting on your own moxie to perform a task you know you’re not suited for isn’t part of the bootstrap mentality; it’s your pride getting in the way.

You gotta know when to hold and when to fold by leaving the round and letting your team handle it. Any other approach will make you feel like a hack — or worse, make you broke.

Your time is too valuable to waste on tasks you suck at or hate, especially if you’re managing multiple companies. Say it with me: Outsource the rest to experts. I really can’t stress this enough.


Keep creating new opportunities

Your best chance of making it as an entrepreneur is to keep creating new opportunities for your various ventures to function in harmony. By playing your cards right, you will give each of your startups a puncher’s chance in the fight for prosperity.

Above all, keep your eye on the end goal in the face of a harrowing workload. Sure, you’re busting your butt everyday (and night and weekend), but you’re working on something meaningful — your own dreams, not those of somebody you’ve never met.

That’s a win you can celebrate every day.


This article has been edited and condensed.

Josh Turner, a Wall Street Journal best-selling author, is the founder and CEO of LinkedSelling, a marketing firm helping B2B companies utilize LinkedIn to reach dramatically more prospects and leads and to increase sales. Connect with @JoshBTurner on Twitter.


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