How to Manage Multiple Companies at Once (And Still Feel On Top of It)

Key advice for serial entrepreneurs who find themselves working on multiple projects at a time.

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By Jennifer Spencer

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Although most entrepreneurs start with just one business, as they scale operations and build out a team, they're often able to start other businesses, too. Inevitably, this is the ultimate form of multi-tasking and must be done tactfully with the right infrastructure within each company. Just ask Joshua Gould — with four portfolio companies on his plate, he learned how to master this intensive form of multitasking early. He is now the CEO of both The Big Word Group and a new company called TBW Global.

We sat down so I could better understand how exactly he manages all of them from a high level and how other entrepreneurs can walk in his footsteps and build their own empires.

1. Groom a qualified team member to take over operations

Giving up primary control of a company you built is never easy, but it can be made easier by having someone you trust learning the ropes for a while beforehand. "It's noticeable who becomes your right-hand man within business operations," Gould says. "Take note of who puts in extra hours, prioritizes a relationship with you and seems generally passionate about what your business does."

Related: The Art of Simultaneously Managing Multiple Companies

The idea is that this right-hand man (or woman) will be groomed to take over operations once it's been decided that you'd like to start another company and relieve yourself of some leader duties. Communicate these intentions early so there are no surprises and everyone's on the same page. Then let them shadow you.

2. Have a "reporter" within each company

Regardless of if you have two or 10 companies, it's important that someone from each can act as the liaison to you and keep you abreast of all company updates. These can include current ad spends, client problems, week-to-week financials and any HR issues that need to be addressed.

Related: How to Split Your Time Effectively Across Multiple Companies

This way, you have someone always keeping a pulse on each company without your need to do the digging. At weekly meetings with the reporter, you can problem solve where needed or assess where you do need to get involved in the week ahead.

3. Make office visits or host team meetings once a week

Make your presence consistent by hosting weekly meetings with all pertinent team members or visiting their office space (if they work together in person). If your businesses operate out of the same city, consider putting all of them under the same roof in a large office building or by leasing space from a coworking studio such as Galvanize or WeWork. That way, you will always be right there to help and keep your hand in everything.

4. Continue to prioritize relationships

Finally, make sure to prioritize relationships with employees and team members at each of your companies. People leave companies all the time; it's best to have an idea of who would be a good replacement if your original "right-hand man" (or woman) left. "I advise getting coffee once a quarter with all the big team members from each of your companies," Gould says.

Related: Why You Should Never Start Just One Business

There's another benefit here: You'll also always have a transparent understanding on how things are going in the business on the ground floor. Although ideally you'd get this information from the liaison or reporter, a lot of what's going on in a business is indistinguishable from the numbers and metrics alone: It's in the culture, client relationships and other gut feelings that should be talked about. The closer employees feel with you, the more they'll feel comfortable sharing these nuances.

It's a juggling game, for sure, but as long as you keep a hand in each company and focus on the major relationships, you'll learn how to manage everything. It may be a learning curve at first as you move away from one business to start or manage another, so be kind to yourself and rely on your team members for help and intel.

Related: Running Multiple Businesses? This Is How Billionaires Apportion Their Time for Maximum Output.

Jennifer Spencer

Entrepreneur Leadership Network Writer

CEO of Energent Media

Jennifer Spencer is the founder of Energent Media, a digital marketing firm for tech startups. She is passionate about helping brands leverage content to share their stories with the world.

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