20 Things to Consider Before You Quit Your Job and Start Your Own Company

There’s a certain sexiness associated with starting a company: The freedom to set your own hours; the allure of building something from scratch. Still, there’s a lot of uncertainty (and often fear) that comes along with abandoning a secure paycheck and the traditional nine-to-five gig.

Here, three former marketing executives share the lessons they learned from launching their own startups and how they knew they were ready to take the plunge.

1) Tell people about your idea. After leading the marketing team at DoSomething.org for five years, Naomi Hirabayashi was ready for something new. The former CMO of the social change and community service organization knew she was passionate about making social action accessible for young people and having meaningful conversations. So, when she and her coworker Marah Lidey came up with the idea for a daily, self-empowerment text service, they started telling friends and family about it. Hirabayashi, now cofounder and co-CEO of the service Shine Text, encourages other wannabe entrepreneurs to take this first step, even if it means just emailing the idea to a friend or brainstorming over drinks at happy hour.

“When you have conviction behind [your idea] and start putting momentum behind it, it starts to snowball into something that becomes bigger than you,” she says.

2) Test your concept to see if there’s a need. After discussing the idea with their peers, Hirabayashi and Lidey decided to run a test. They sent daily texts to 70 people within their network and conducted weekly surveys to better identify which SMS content resonated with users the most. A few months later they launched a public beta test. After experiencing “a lot of organic pickup” Hirabayashi and Lidey decided to turn their side project into a full-time gig.

“If we never took the leap, we would never know what it could be,” Hirabayashi says.

3) Find a complementary partner. When it comes to cofounding a business, choosing the right partner is crucial. In fact, Ashley Daly—former SVP of global marketing for marketing platform and service provider Experian Marketing Services—says it’s one of the most important decisions an entrepreneur can make before launching the company. 

Daly cofounded corporate gifting marketplace and service Sercy with a former colleague from Experian. She describes the business partnership as “complementary,” meaning they each brought a different skill set to the table. Daly encourages other entrepreneurs to find partners with harmonious skill sets, rather than identical ones.

“If you’re very similar, then that’s going to become combative and it’s going to become one person trying to trump the other,” she says.

4) Define each partner’s role. While partners may share the title of cofounder, it’s essential that each person has a clear understanding of his or her unique role. Defining these roles, Daly says, helps establish expectations and holds each person accountable for hitting key milestones.

5) Communicate openly and make decisions based on the betterment of the company. When launching a company, it’s important for entrepreneurs to remember that they’re no longer single entities, Hirabayashi says; they’re now part of a greater whole. That’s why it’s vital for them to check in with one another regularly, she says. And when disagreements do arise, they need to listen to each other and make decisions based on what will advance the business, Daly adds.

“It’s not personal,” Hirabayashi says. “It’s what’s the best thing for the baby?”

6) Understand that not every partnership will work out. An entrepreneur’s personal life doesn’t pause when she launches a business. Daly recommends finding a partner who can withstand personal interruptions and proceed as necessary—a lesson she learned after she and her original cofounder decided to part ways.

“Times will be hard, harder than you ever expected,” she says.  “You will need people in the foxhole with you on the same page ready to take on whatever comes your way.”

7) Switch from thinking reactively to proactively. When people work for an established company, most of their tasks are reactive, says Romy Newman: They’re responding to customers’ emails, answering coworkers’ questions, measuring deliverables, etc. But after Newman left her post as head of digital advertising for The Wall Street Journal and cofounded  Fairygodboss—a job listing and company review site designed for women—she found her inbox empty, signaling that if she wanted to drive interest, she would have to reach out proactively.

8) Realize that you no longer have departmental support. When Daly worked at Experian and needed a new piece of creative, she could simply turn to her marketing team to crank it out. Now that she’s running her own business, she has to do these tasks herself, resulting in her dabbling with tools she hasn’t touched in years.

“Suddenly things that used to be so easy for me to accomplish are now taking so much more time because I’m having to relearn a lot and without this fantastic team around me,” she says. “That’s been one of the most challenging things. I tend to move very fast and having to pause to try and figure out how to make something work or create another layer is frustrating.”

Newman also says not being tied to a particular department gives her freedom to explore business areas that were traditionally outside of her domain.

“I’m getting involved in every aspect of the business, and that’s so exciting,” she says. “I’m learning so much every day because I’m so proud.”

9) Leverage available resources. Running a business is a learning curve, and Hirabayashi encourages other entrepreneurs to access all available resources.

“Google is your best friend,” she says.

Indeed, Newman and her cofounder knew SEO would be a key component for promoting their online business. But after they realized they couldn’t afford to hire an SEO agency, they scoured the internet for articles and videos and learned how to do it for themselves.

Hirabayashi cites websites like Quora and books like The Lean Startup as some of her favorite resources. She also recommends listening to TED Talks, cold emailing experts, and grabbing coffee with those who are willing to lend advice.

10) Gain sales experience. Newman considers sales experience the best skill she brought over from The Wall Street Journal—a skill set she advises all entrepreneurs to develop no matter what their discipline is.

“[Sales] teaches you how to communicate,” she says. “It teaches you how to network and create connections with people; it teaches you how to persuade; and…it teaches you how to hear no and handle rejection.”

11) Understand the power of messaging through the right channels. There are several ways Shine interacts with its members. It sends Facebook Messenger or SMS messages daily, depending on the user’s preference, and sends emails weekly. While Hirabayashi acknowledges the power of email, she considers SMS a better channel for Shine because it allows the brand to communicate with users the same way they communicate with each other.

“We think the power of messaging is the most important for the product because it’s kind of baked into your every day by coming to you like a friend,” she says.

12) Realize that time is what you make of it. Both Daly and Newman agree that having the flexibility to set their own schedules is the biggest benefit of running their companies. And even though they’re now able to pick up their kids from school and determine their work hours, they still end up working more—just on their own time.

“Even though I have more flexibility, it’s also completely 24 hours a day,” Newman says. “There’s no longer really any such thing as a vacation. I’m working when I can work all of the time because I want this thing to succeed so badly.”

13) Set ambitious goals. When Newman cofounded Fairygodboss, she and her partner knew they had to grow their user base. What they didn’t realize, however, was how quickly they would meet their target goal. Newman says they grew Fairygodboss’s audience from 17,000 users per month in January to 74,000 users in August—acknowledging that she and her partner should have set more ambitious goals in the beginning.

“You have to be really aggressive with your own expectations and hold yourself to it,” she says, “because it’s sort of as big as you can dream it.”

14) Weigh your funding options. Money can be a touchy subject. There are so many ways to secure funding, and it’s important for entrepreneurs to weigh them all. For instance, Daly recommends considering the pros and cons of having an investor. On the one hand, investors provide ample advice and a gateway to a large network, she says; on the other hand, they expect a return. She also advises startup newbies to look at how much of their own money they’re willing to invest and how much of their company they’re willing to give away, which can be done through equity or shares.

Newman says it’s important for entrepreneurs to consider whether they’re able to take a salary. She also says asking family and friends for funding is an option. However, Hirabayashi says money shouldn’t be entrepreneurs’ sole deterrent from starting a company.

“You don’t have to have a rich uncle or aunt to do it,” she says.

Having a contingency plan (such as the willingness to freelance), she says, can provide a little security if things go south; however, she discourages entrepreneurs from relying on this plan too heavily.

15) Forecast your company’s future. Entrepreneurs can throw money at advertising all they want. But unless they figure out how the product can grow an audience on its own, they won’t be successful, Newman says.

16) Don’t ignore the small details. Entrepreneurs have several big-picture items to manage, but remembering the smaller details is essential, too. Daly recalls struggling to choose the right email service provider and testing a few trial runs. But when she and her partner failed to realize that their trial period had expired, they stopped receiving emails and were unable to recuperate the lost ones.

“Sometimes it was more of the smaller details, but important ones, that we had kind of missed,” she says.

17) Consider the right legal team. There are a lot of legalities associated with starting a business. Daly recommends hiring an expert who specializes in startups, especially those within a specific domain, like technology or e-commerce. Doing so, she notes, can help entrepreneurs establish the right guiding principles and operating models.  

18) Understand the value of not compromising. It’s always important to listen to partners’ and investors’ viewpoints (see tip number five); but if entrepreneurs are strong in their convictions and they believe their decisions are what’s best for the company, then they should stand their ground. 

“Stay strong; stick to the plan; be flexible; but don’t be afraid not to compromise.” Daly says.

19) Be flexible. At the same time, entrepreneurs need to understand that their business strategy, offering, or operating model may evolve over time.  

“What we’ve heard from other people is ‘whatever vision you had is going to change,’ and that’s so true,” Daly says. “It continues to evolve and get modified.”

So remember, sticking to one’s guns and being stuck in the past aren’t the same things.

20) Don’t be afraid to take risks and believe that you can succeed.  For most of her career, Daly has had secure jobs. Now, that she’s building her own company, she says it’s hard not to fear the unknown. Still, she encourages entrepreneurs to go after what scares them the most and to seize the opportunity if the timing and the market is right.

“Don’t be afraid to be strong,” she says, “and don’t be afraid to believe that this is going to be successful.”

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