Confessions of a Female Entrepreneur. 7 Tips from a Successful Businesswoman.


I am a female entrepreneur — a successful businesswoman. I want to share a bit of my journey to entrepreneurship with other women driven to become successful business owners themselves. I also include a few entrepreneur tips along the way.

successful female entrepreneurship

I have been in or involved with the technology industry for thirty years. For twenty-three of those years, I held B2B (business-to-business) marketing management positions where I took complex technology and made it easily understandable and relevant to non-technical business professionals. I worked for large, global organizations and small start-ups. I know how successful businesses run and have been hired because of my experience to drive business growth.

My work ethic and integrity enabled me to build an outstanding reputation across the industry and develop a large network of business colleagues and relationships that still thrive today.

With this level of experience, I could certainly become a female entrepreneur. Right?

Yes.

Undoubtedly, it would require a great deal of commitment and a lot of work. But no more commitment and work than I already demonstrated in my corporate positions. I always put 100 percent into everything I do. I’ve already been a successful businesswoman. I just haven’t worked for myself.

I have my entrepreneurship plan. The time has come. It’s time to execute that plan.

Reality-Based Leadership

Becoming a female entrepreneur wasn't something that popped into my head one day, and I decided to start a business the next. It was a vision and dream I had for well over a decade.

Finally, the stars aligned seven years ago, and the time was right to start my own business. Not only that, since I spent over a decade considering every opportunity and obstacle that could come my way as a small business owner, I was ready for any possibility. I had answers, solutions, and workarounds for every eventuality. Or so I thought.

I left my corporate position and started a marketing firm targeting companies similar to those I worked with in the past. By the end of year one, my goal was to have enough clients to keep myself and three full-time employees very busy. I would also hire specialists in specific areas of marketing to work on individual client projects. Of course, my company would also be making a profit.

What slipped my mind in all of this was that I would be much more than the business owner. I became a salesperson, a human resource manager, a business attorney, a marketing professional, a chief financial officer, an IT guru, and an office manager. As a solo entrepreneur, it never dawned on me how that would affect the speed with which I could promote my business, close new clients, complete client work, make money, and grow.

What has surprised me most about this journey that I have been on for almost seven years? How long it actually takes to build a profitable business. For example,

  • The number of times you must meet with a prospect before they become a client

  • How long it takes to build back-end technology to support your business operations

  • Finding the right people to work for you

  • How slowly large corporations move when making decisions on projects you have discussed with them for months

Of course, having spent many years in the corporate world marketing and selling to B2B clients, I already knew this, but it's a different story when you are the one responsible for all the individual pieces.

7 Entrepreneur Tips from One Female Entrepreneur to You

Is your dream to be a successful woman entrepreneur and build your own business? Well, be mindful of my story. When you think you’re ready, think twice. I don't mean to say that you shouldn't do it—quite the contrary. You should start your own business. It is an amazing journey. I have learned and grown so much, and you will too.

My advice is to go for it. But with these seven tips in mind.

female entrepreneurship. tips to be a successful businesswoman.

Entrepreneur Tip 1: You Need Money to Make Money

It’s no accident that I listed money as the first tip. Your expenses will grow and your savings will shrink at lightning speed.

Stay at your current job longer than you really want to and put as much of your paycheck as you can into a separate bank account.

Live frugally. Stop going to Starbucks, cancel your cable television subscription, bring your lunch to the office, sell the second car, and tell the lawn service you will be cutting your grass.

Do you have a working spouse? Great. You should both live on one salary and bank every bit of the other salary.

Remember two things:

  • Banks and investors will not give you money without customers so expect to have to finance your business on your own for the first two to three years depending on the type of business you start. Do you have enough money to grow your business, eat, pay the mortgage, and live for three years? If not, stay in your current job and stash away every paycheck you can.

  • Your expenses will grow faster than your business. Building a website, hiring an accountant, developing a product, buying computer equipment, and hiring someone to fix it when it breaks, all take money. Remember, this cash outlay will happen before your first customer ever pays you.

Entrepreneur Tip 2: There is Support for Small Business Owners

It is common for female entrepreneurs (and male entrepreneurs, for that matter) to deal with bouts of loneliness and uncertainty, especially when working at home alone or in a small co-working space.

And, women who stay at their corporate jobs, working on their business at night and weekends, often keep it a secret from their employer and co-workers for fear of being fired.

In either case, you may be in a constant state of self-doubt about whether you are doing the right things in the proper order, moving your business in the right direction, and if customers will want the product you are developing.

It is essential to get the encouragement and support you need to keep moving ahead. You can get this from:

  • Someone you know and trust who understands your business and could become an advisor

  • An agency, business group, or professional organization that provides online resources and education

  • A community of like-minded businesswomen who meet for professional training but also personal support, encouragement, and advice from others on this entrepreneurial journey

Here are some small business and women entrepreneur-focused resources you may want to check out.

Small Business Resources

  • US Small Business Administration (SBA)

    The SBA is a government entity that offers many resources, from business guidance and funding programs to federal contracting and local support. Local Small Business Development Centers (SBDCs) provide entrepreneurial training and counseling in your community.

  • US Chamber of Commerce

    The US Chamber of Commerce advocates for policies that help businesses create jobs and grow in a constantly changing economic environment. Members include small businesses, community-based chambers of commerce across the country, industry associations, and global corporations.

  • WBENC

    WBENC, the Women's Business Enterprise National Council, is a leading non-profit organization dedicated to helping women-owned businesses thrive. The organization has set the standard for women-owned business certification accepted by thousands of corporations and many state, city, and government entities.

  • CWE

    The Center for Women and Enterprise (CWE) helps women business owners and aspiring women entrepreneurs launch and grow their businesses by providing greater access to the resources, tools, and support they need. CWE works locally with women business owners in the New England states of Massachusetts, New Hampshire, Rhode Island, and Vermont.

  • International Trade Administration

    The International Trade Association is a US government agency led by the Under Secretary of Commerce for International Trade. It is your essential international business resource for practical exporting advice, trade data and analysis, individual country overviews, and much more.

  • IRS Small Business and Self-Employed Tax Center

    The IRS Small Business and Self-Employed Tax Center provides resources for taxpayers who file Form 1040 or 1040-SR, Schedules C, E, F, or Form 2106, as well as small businesses with assets under $10 million.

Entrepreneur Tip 3: You Can Run in Stealth Mode If You Have to

If you currently work at a day job while getting your business off the ground, your employer may be concerned that your priorities are split between these two responsibilities, and you are not giving 100 percent of your time and effort to the work for which they are paying you.

If they suspect a side hustle could be interfering with your work for them, they may go online to look for a website, blog content, or anything else with your name on it to see if you are involved in a new business venture. If your situation is similar, consider running your business in stealth mode for as long as possible.

For example, did you know that a company's About Us page is one of the top four most visited pages on any website? While many About Us pages include names and photos of the management team, you can create a pen name to represent yourself as the person running the business. You might want to call yourself the Fashionista, the Marketing Guru, the Hospitality Host, the Financial Sage, the Chef, or something similar. Create a pseudonym appropriate for your business and industry and use it on your website and email communications instead of your real name.

Similarly, the email address listed on your site does not need to contain your actual name. You can create an email address like info@yourcompanyname.com, hello@yourcompanyname.com, TheFinancialSage@yourcompanyname.com, or TheLegalLion@yourcompanyname.com, which customers can use to contact you.

Entrepreneur Tip 4: Have Potential Clients Waiting in the Wings

Get to know as many people as you can in the industry in which you will start your business. That’s easy if your new business is in the same industry as your current job. Developing a good reputation and long-lasting relationships will help your new business get out of the starting gate more quickly.

When I decided to leap into entrepreneurship, I reached out to colleagues and friends in the technology industry, letting them know I was leaving my current position and explaining my plans. Because of the relationships I built over time, various contacts immediately said they wanted to hire me.

The news of my plans also spread to firms I had not worked with for years, but they reached out to chat about possible opportunities as well. The fact that I could immediately put together a group of clients helped sustain me in the first two years of business.

starting a business is a long and challenging road quote

Entrepreneur Tip 5: Set Specific Business Goals and Deadlines

Juggling a day job, side business, and personal life can be daunting. When deciding which one you should focus on first, the day job and the personal life will usually win out. As a result, the entrepreneurship goals and dreams you carry around in your head never come to fruition.

Write a business plan which includes specific goals and deadlines that will enable you, if accomplished, to quit your day job and follow your dream. Attach measurable actions to each goal and have a mentor, peer group, or close friend hold you accountable for achieving those goals by the deadlines you have put in place.

Break these milestones into smaller, bite-size projects or tasks to be more easily attainable. Whether it is a small task like setting up a business bank account or a more extensive project like designing, writing, and launching your website, every goal you achieve and deadline you meet provides you with an ever-increasing sense of confidence. It brings you closer to the day when you become a successful entrepreneur.

Entrepreneur Tip 6: Passion Will Help Sustain You

Setting specific goals and deadlines is essential, but if the passion for your new business is gone, then the chance of success is slim. After eight months of working on your new business while still at your corporate job, ask yourself, “Do I have as much passion as I did when I first wanted to be a business owner?” If you do, keep going. If you don’t, consider if this journey is right for you.

Remember, you are still giving 100 percent of your effort to your day job and working on your new business at night, early in the morning, on weekends, and any other time you have available.

Do you slink home at night and want to flop on the couch and watch television, or do you rush home to uncover new business opportunities and jump out of bed two hours early to complete those items on your to-do list?

Entrepreneur Tip 7: Don’t Hire Full-Time Employees without Considering Alternatives

Believing you must hire full-time employees right out of the gate will quickly drain your bank account. There is an alternative—freelancers. Freelancers are the fastest-growing portion of the labor market and have come a long way from the traditional "temp" employee that we remember from ten or twenty years ago.

Today’s freelancers are well educated and have many years of experience. They include attorneys, accountants, marketing executives, management consultants, start-up specialists, and more.

Hiring freelancers to complete specific projects or provide strategic consulting services lets you take advantage of qualified professionals, paying for only what you need and nothing more. There are no additional expenses when the job is done, and the outflow of cash from your new business stops immediately.

Best of all, technology like Zoom, Skype, Slack, Teams, and other video, messaging, and meeting tools enable you to hire and easily communicate with the most qualified workers, whether they are down the street or around the world.

Women’s Entrepreneurship: The Bottom Line

So, after almost seven years of being a woman business owner, did I do the right thing? Am I happy I took the leap and started my own business? Absolutely . . . with a big BUT attached to it.

Had I known then what I know now, I would have stayed longer at my corporate job, developing and growing my small business in parallel before leaving my executive position. That would have helped to lengthened my start-up runway once I left to be a full-time entrepreneur.

My advice to you: Take some time to sit down in a quiet place and honestly evaluate your readiness—your personal needs, financial needs, and business goals. If you are genuinely passionate about this business, you will have the drive to build it while you are still at your current job. Then leave at the appropriate time.

Starting and growing a business is a long and challenging road, but so worth the ride to becoming a successful female entrepreneur.


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Lisa M. Masiello

I help real people turn ideas into businesses from scratch. I’m an author and business owner sharing clear advice, useful tools, and the kind of resources I wish I had when I started. No hype. Just help.

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