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Start Your Business Startup Basics

Want to Launch Another Business? What You Need to Know

image for loreanto/Shutterstock
loreanto/Shutterstock
  • Running multiple businesses at the same time is possible, but it takes a special team and a supportive board of directors.
  • Understandably, time management is the most challenging aspect of running multiple businesses.
  • To manage your time effectively, consider hiring a personal assistant or, at the very least, hiring great team members and delegating work.

Starting and running a business can be extremely challenging. From marketing strategy to financial challenges to time demands, few things about running a business are easy. For some people, this doesn't matter. For some, the thrill of launching and successfully running a business beats out all the demands that come with the journey.

Some people are born with the entrepreneurial bug. For these people, the excitement and grind of starting and running a business are so motivating they want to do it repeatedly.

While some serial entrepreneurs will launch, build and exit the companies they start, others want to continue running their first venture while working on the second (or third, fourth, etc.). It can certainly be done, but it takes a lot of hard work and dedication to each of your businesses.

We spoke with entrepreneurs who run multiple businesses about their experiences and what other business owners should know about owning multiple small businesses.

As you've probably learned from your current business experience, entrepreneurship requires wearing a lot of different hats. You need to be organized and know your priorities to stay on top of things – and that's just for one company. Your biggest priority as a multibusiness entrepreneur is prioritization itself, said Emily Miethner, CEO and founder of FindSpark and MGC Social, and owner of two Long Beach, New York, food trucks.

"Knowing how to effectively split your time to ensure both businesses thrive is definitely a skill," Miethner said. "It's important to have the systems and processes in place – and, of course, the team – to ensure you can scale and handle both."

"I go by the philosophy [of getting] the challenging things done first during the day," said Loren Ridinger, co-founder of Market America and SHOP.com, and founder of Motives Cosmetics. "Once those are done, I can then enjoy the rest of the day and be creative." 

Time management is one of the toughest challenges of running multiple businesses. You need to determine when you'll spend time on each business and how you will delegate different business tasks. It's nearly impossible to run multiple businesses without an excellent team helping you manage your responsibilities. In some cases, it may even help to hire an assistant to help you keep track of your different responsibilities. 

When running multiple businesses, you want to spend time on important work. You don't want to focus on juggling your schedule or scrolling through old emails. Try to streamline processes and develop some type of routine to block out all the additional noise that comes with running different businesses.

This means a few things. First, does your physical business location make sense? Second, are you in a good place geographically to recruit and hire top talent? Third, when can you be at the physical business location or office for your businesses? 

One of the most obvious challenges of opening a second business is not being able to be in two places at once. When you're at one business, you can't be at a different location, which means you must make sacrifices. If you're running small e-commerce brands out of one office space, the location concern isn't as big. 

Office location matters as you consider expanding. Growing your business may require more employees and an office expansion. It's easy to forget about business location, but it's a critical part of opening a second business. Traffic can even become an unexpected concern depending on where your business is located.

This comes with starting any business, but you need to go through the basics of planning out a new business, which can be challenging when you're already running another operation. You need to determine a handful of things when opening your second business, and it can be helpful to put these into a written business plan. 

  • Legal structure – Will your business be a limited liability corporation? Will you opt to form a partnership instead? There are several different business structures in play, and it's important to determine the best option for your new venture, especially when it comes to reducing liability and keeping your personal assets protected.
  • Marketing strategy – How will your new business attract customers? Who are those customers? Will social media marketing play a role in the strategy? Expect to spend significant time figuring out how to market your new product or service.
  • Financing – Will you need business loans? Will you enlist the help of investors? Will you create a crowdfunding campaign? 

There are other aspects of a business plan that should be considered, like your organizational structure and revenue drivers. Creating a business plan isn't just for serial entrepreneurs, though. Even if you're running just one business, you need to know about your target market, revenue channels and financing expectations.

Whether your businesses are related to each other or in different industries, they have at least one thing in common: you. Even if the connection is not obvious, consumers and business partners can easily discover that you're at the helm of each company, so you'll want to keep your values consistent. Mathieu Massa, CEO of Mr. Hospitality, who owns and operates multiple restaurants and nightlife destinations, said to make sure that strategies in one business do not conflict with those of the other business(es).

"If you're running a business in which your sales speech focuses on protecting the environment and, on the other hand, you start a business that does completely the opposite, you immediately lose credibility," Massa said. "Find out what your core values are and develop them in all your ventures."

Serial entrepreneur Nick Matzorkis, who co-founded Union Square Media, agreed that your businesses should complement one another, especially in practical ways.

"When I have multiple businesses, I ... mold and manage them in such a way they benefit one another in supporting and helping each other grow," Matzorkis said. "[This can be done] by reducing costs – e.g., sharing common accounting or IT departments, sharing office space, or even shaping simultaneous companies to parlay off of each other's cash flow by benefiting from complementary seasonality trends, for example."

Some of the entrepreneurs we spoke to emphasized diversifying their income channels. Running different businesses is a way to bring in money from different sources, but that doesn't mean your brands need to be complete opposites or work completely separately from one another. By sharing workspace or IT staff or working toward similar missions, you may find even better success as a serial entrepreneur.  

It takes a significant amount of work to run one business, let alone multiple companies. However, it doesn't have to mean more work for you if you hire the right people to help you out.

"We've worked very hard to find the right people who are exceptional leaders, and because of that focus, there is awesome synergy between our brands," said Brian Scudamore, founder and CEO of O2E Brands, the parent company of home service brands Wow 1 Day Painting1-800-GOT-JUNK?You Move Me and Shack Shine. "All of our managing directors work closely together [and] share best practices, wins, and culture tips. Having four businesses led by the right people is actually a lot easier than just having one."

"I am a very hands-on person and like to be a part of all the decision-making for all of my brands, [but I have] the team and support behind me to help me execute my daily tasks," Ridinger added.

It's not easy to find great talent, either. Your business needs to develop strong recruiting and hiring practices to find the right fit to join your startup or growing business.

Once you find these talented team members, let them shine. Don't micromanage. You brought team members on for a reason, so trust them to do their jobs. It's not a bad thing to delegate.

"One of the biggest challenges for me was letting go of the reins a bit," said Tom Baber, owner of a Money Mailer and an IHOP location. "When I first started branching out, I was micromanaging in order to feel in control of every aspect of every business, which is just not possible. To be able to step away a bit and focus on other aspects, it's critical that you build a team you trust, which was another challenge."

Finding the right team takes time, and hiring is one of the most important considerations when running multiple businesses. You need workers you can trust.   

"To successfully run multiple businesses in tandem, you need to delegate to competent members of staff and remove yourself from day-to-day processes," said Adam McIntyre, a graphic designer and entrepreneur. "For many startups and early-stage businesses, this can be challenging. Hiring competent staff can be expensive, and likewise, it can be difficult to find staff members with the same drive and ethos as yourself."

While it's not easy to hire great employees, it's far from impossible. You need to perform a detailed search to find the best employees, but using things like employee referrals can help make the process a bit easier.

Before you can think about staffing your new venture, your original employees should be on board with your decision, especially if it means they'll be working for both companies, said Dan Gordon, co-founder and head brewer of Gordon Biersch Brewing Co. and Aurum Cider Co.

"Make sure you have the support of your team when making the move and have all of the resources you can muster so the probability of success is great," said Gordon.

Serial entrepreneurs need good team members to succeed, so it's important to value their input and treat them well. If you have different teams at different companies, take time to support and recognize team members at both organizations regularly. It's important to remember that you aren't the only person involved with the day-to-day grind of certain business activities.

Many of our sources said that one of the perks of owning multiple businesses is the opportunity to gain new knowledge and perspectives on how to approach certain business strategies.

"The best part of running multiple businesses ... is learning different methods of marketing, running and building teams, pricing – everything, really," Miethner said. "There are a lot of elements from each you can experiment with on the others. It creates great perspective. For instance, working in the food trucks always reminds me how important customer service and sales are, even though doing both on a food truck is extremely different than what we do through [a professional service organization like] FindSpark."

There are even lessons to be learned when you're working in a similar industry. Gordon noted that, even though both of his companies are in the brewing industry, he faced some production challenges because of the scientific fermentation differences between beer and hard cider.

Learning about new industries and meeting different people may even stir up ideas about future businesses to start.

You may be excited at the prospect of launching your next business, but you don't want to bite off more than you can chew. As with any venture, you need time to devote to this new startup to make sure it succeeds – meaning that your first business should be self-sufficient enough for you to step away from it.

"I decided to take on my second venture, Wow 1 Day Painting, after 1-800-GOT-JUNK? was well established," said Scudamore. "1-800-GOT-JUNK? had been built into an international, $100 million business, and we had proven systems that we could leverage in our next brands – a centralized call center, booking and dispatch software we'd created in-house, marketing systems, and PR know-how."

If you feel the overwhelming entrepreneurial urge to start something new, some of our sources advised simply going for it. For instance, Matzorkis said he never consciously set out to start a new company – he recognizes and acknowledges ideas and opportunities as they come to him, and if he has the resources and the passion for it, he moves forward.

"I've never started a business simply because I saw it as a good business opportunity alone," Matzorkis said. "For me, any new business must be more than just a sound business model for me to maintain the focus and drive needed to guide it to success. This personal guideline is of importance to me when choosing to launch and operate multiple companies simultaneously."

"I don't think entrepreneurs wait for a green light," Gordon added. "You get an idea and just run with it, regardless of whether it fits into your readiness mode."

While Gordon's point is spot on, it's also important not to create a second business in hopes of miraculously generating more cash flow to use for your first business. Don't leap into something without some financial plan for success.

"Be careful you don't jump too quickly to open a second business," said Stacy Tuschl, small business growth coach, founder of the Foot Traffic formula, and host of the Foot Traffic podcast. "First, ask yourself, why do you want to do this? If the first business isn't bringing you enough income or you aren't enjoying it, I would suggest fixing that problem before creating another one. If your first business isn't a well-oiled machine, it is time to slow down and maximize Business No. 1 first. Just remember Rome wasn't built in a day, and acquiring too many businesses too soon can hurt your business rather than build your empire."

Bennett Conlin

Bennett is a B2B editorial assistant based in New York City. He graduated from James Madison University in 2018 with a degree in business management. During his time in Harrisonburg he worked extensively with The Breeze, JMU’s student-run newspaper. Bennett also worked at the Shenandoah Valley SBDC, where he helped small businesses with a variety of needs ranging from social media marketing to business plan writing.