Mar 8, 2022

50 Pieces of Advice from Women Entrepreneurs

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Capstone Celebrates National Women’s Small Business Month with Advice from Female Founders & CEOs

During National Women’s Small Business Month, we want to recognize the many women entrepreneurs who have continued to lead a growing share of U.S. businesses, with women-led companies climbing from 4.6% of businesses in 1972 to 42% in 2019, according to American Express’ most recent State of Women-Owned Business report.1  Despite unique challenges, including being 63% less likely to receive venture capital financing than their male counterparts (Columbia Business School2), the number of women-owned businesses increased 21% between 2014 and 2019 alone to ~13 million, compared to a 9% increase in all businesses over the same period.

Notably, women CEOs running small and mid-sized enterprises (SME) have far outpaced those at larger organizations and are setting the stage for future generations. In 2021, just 8.2% of Fortune 500 companies were being run by women—and that’s the record high.3 The figure rose from 2020 with the additions of Karen Lynch as CEO of CVS Health (NYSE:CVS), Roz Brewer at Walgreens Boots Alliance (Nasdaq:WBA), and Thasunda Brown Duckett at TIAA (also marking the first time two Black women are CEOs of Fortune 500 businesses). Despite the gradual shift at the Fortune 500, progress is being made and 79% of women entrepreneurs surveyed reported feeling more empowered today than they did five years ago, according to Visa’s 2020 State of Female Entrepreneurs Report.4

Advice to the Next Generation from Women CEOs

As we look ahead to the future landscape of the middle market, we asked our network of C-suite female executives, "What advice do you have for the next generation of female business leaders?" Here’s what they said:

  1. Step up. Speak up. Take credit for your work and look for mentors where you can find them. Hang with powerful women.
  2. Choose your prospective investor audience carefully and understand their expectations.
  3. Develop a robust network; become a technical expert; hire people who are good in the areas you are not.
  4. Be strong, work hard, and never give up.
  5. With the need for change on many levels of our society including business, politics, etc., now is the best time for women to influence and lead businesses.
  6. Take yourself seriously or others won't. Tell your personal story to add credibility to what you are currently doing and striving to do in future. Proudly take a seat at the table, any table. Know you have something to offer that is unique and important. Know that you are not alone, but also that you as an individual stand on your own very valid merits.
  7. Work hard, be resilient and don't get caught up on the "glass ceiling."
  8. Speak up, push in, don't hold back. And when you get discouraged, do it again.
  9. Own your power.
  10. Advocate for flexibility for working mothers. Very challenging to balance mom and work-life balance. To have both makes for a happy long-term driven employee striving for the company’s greatest achievements.
  11. My advice is for business leaders of both genders. It's all about the work and the relationships. Keep those two things at the top of the list.  Know what you don't know, and don't be afraid to ask for help from people who do know. But, don't mistake your inexperience for incompetence. You can always figure it out. And, don't mistake expertise for infallibility. An expert is just someone with more experience than you. It doesn't mean they always know the answer either.
  12. Assume acceptance. Be fearless and if you have a good idea, do not let it go.
  13. Keep a sense of humor.
  14. Make sure everyone at the top level has a stellar reputation and a strong network of people they can raise capital from. Everyone needs to participate in raising and everyone at the top needs to put their own money in the game if they want to be in leadership.
  15. Be clear on your vision. You’ll get a lot of conflicting advice and people trying to tell you what to do. Stay clear.
  16. Use "I" more. Explicitly, though humbly, call out successes, accomplishments, and strong decisions that you made.
  17. Do your homework and be prepared and then go after things, get into the meetings, make the contacts you need to because nobody is ever going to invite you. You have to do it.
  18. Don't approach the marketplace as a woman in business but as a businessperson. Be professional and always strive for excellence, not perfection.
  19. Learn to say no and be confident early.
  20.  Ignore any slights you may feel. Take the high road. And work hard at your business - show that you are a "real" business. There are lots of female-owned food companies, so the industry is used to us being dominant figures everywhere.
  21.  Believe in yourself. If you think you can or you think you can't, both will be right. Don't be afraid to dream big and chase hard.
  22.  Find your own confident voice, and spend the time to find the right partners, investors, teammates that will respect and support a female CEO.
  23.  Guilt is a useless emotion.
  24.  Practice respect, integrity, and character.
  25.  Don't ever let anyone else speak for you.
  26.  Do you. Find a network to learn and gain as much knowledge (both men and women). Seek out people that are smarter than you in areas of skills you do not have, they will make you soar.
  27.  Don't be intimidated, you are a powerful woman, and you can accomplish anything. And don't be afraid to ask for help.
  28.  Be purpose driven and trust in your own abilities.
  29.  Work hard, be passionate, and listen intently to people whose opinion you value.
  30.  Band together to see each other’s visions. You will all require the same services in business. Find ways to pool together not pull apart.
  31.  Tools to stay the course: Perseverance, Determination, Will power, Tenacity, Reach out and ask for help, be humble, most of all be yourself!
  32.  Believe in yourself. Find allies in your industry or related industries. Mentor other women. Steer clear of gossip. Treat others the way you wish to be treated and don't tolerate anyone who doesn't respect you.
  33.  Mentor all.
  34.  Don’t apologize and be authentic.
  35.  Know the details and make your voice heard.
  36.  Listen to your gut. If it feels right do it if it doesn't don't. Women have great intuition, and they should hone that ability.
  37.  Be yourself and seize every opportunity that comes your way - not every generation has that freedom.
  38.  Surround yourself with the smartest people you know and be honest with yourself about your shortcomings and the things you hate to do and hire the best people you can find to do those things!
  39.  Gender nor race can keep you from your goals. Do everything in your power to obtain and gain the knowledge you need to be successful. Do not be prideful but rather strategic. Ask for help when needed, surround yourself with people that motivate, cultivate and stimulate your passions.
  40.  Listen but don't bend.
  41.  Be direct, be bold and be yourself. Don't try to fit into a narrative that is not yours.
  42.  Play to your strengths. Don't try to be someone else.  Don't play someone else's game.  Hold your vision.
  43.  Don't expect to be held back because you are a woman. Expect to excel because you are a woman and if you are held back, adjust accordingly.
  44.  Just do the best you can. Find mentors and partners to shore up your weak points and get other points of view.
  45.  Learn hard skills—finance, law, etc. that will provide you with the specific skills needed to run the business outside your special interest or you will find it much more difficult to succeed.
  46.  You have no natural boundaries or impediments unless you believe you do. There is no substitute for hard work.
  47.  Build your network of people who can advise you and help move you up the ladder. The word I live by is PERSISTENCE.
  48.  Work hard to produce quality and establish your record as an ethical, knowledgeable producer in whatever area you work and service.
  49.  Be very clear about what you want and work to craft an opportunity that allows you to work in ways that work for you.
  50.  Don't quit even if you fail.

Updated March 8, 2022. 


  1. American Express, "The 2019 State of Women-Owned Businesses Report,", accessed October 6, 2021.
  2. Columbia Business School, " Why Aren’t Startups Founded by Women Getting More Funding?,", accessed October 6, 2021.
  3. Fortune, "The female CEOs on this year’s Fortune 500 just broke three all-time records,", accessed October 6, 2021.
  4. Visa, " Visa Champions a New Decade for Women’s Empowerment,", accessed October 6, 2021.


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