How Do I Advise Female Entrepreneurs?

I was approached by two female entrepreneurs. They asked if I would be an advisor to them in their new business. I met them over two years ago when they pitched me on investing. I tried to help them by connecting them with an early stage VC. I figured if he invested, then I would invest behind him. He was more familiar with their market and business model than I was. He didn’t invest, so I didn’t either.

Will You Advise?

Back they came, asking me to be an advisor. They said their goal was to build a fast-growth technology startup. When they approached me this time, they told me they had already raised over $350k and had sales growing at 20% month on month. I was very excited about them and their market when I met them. I was now even more excited seeing their results.

We, along with their lawyer, met in a restaurant. He laid out the deal for me as an advisor to their company. It was a fair deal, and I thought I could help. I told them I needed to think and pray about their offer. Within a week, I called and told them I would help.

Something Haunting Me

Something I said at the end of that lunch kept haunting me. I made the kind of statement I say to everyone I advise, “If you work with me, we’ll be focused on building your business while serving your family. You only have one life.” As I prayed about them and their business, I found myself focused on their marriages and their relationships with their children.

I couldn’t shake this thought, Do I advise them to build a fast-growth business the same way I advise men? I didn’t know what to do with this. I have never advised female entrepreneurs. I understand the challenges men face in building a business and keeping good relationships at home with their wife and kids. But I don’t know about being a woman, wife, and mom.

Stick to the Business

I called their lawyer to tell him my concern. He said, “You are being asked to help them build a fast-growth business. You know how to do this, and they need this council. That’s why they approached you. Stick to this advice. Don’t consider their family as a constraint to their growth. That is their responsibility.”

I agreed with him when we talked. But after I got off the phone, the thought of growing a business at the expense of their families didn’t sit well with me. So I continue to pray about this in anticipation of our next meeting.

In the meantime, I was at a business dinner with a mix of executives, entrepreneurs, and VCs. A few of the entrepreneurs were women. One of them said, “Growing a business as the founder and a single mom is challenging.” When I heard this, I leaned in. On a break, I made a point of telling her about my concern with the entrepreneurs who asked me to advise them.

What About Mom Guilt?

She told me it has been difficult for her. She grew a very successful business from scratch but in the process lost her marriage. Her company grew quickly, but now she has to balance company growth and the demands of being a mom. She said, “I deal a lot with working mother’s guilt.”

I told her, “I never heard that term.”

I asked if she would meet with the two women who were in the early stages of growing their company. I said, “I don’t know what to say to them on this topic. But I know the family will be part of the formula in growing their company. It can’t be ignored. You’ve been there. Would you share your experience and give them and me advice?” She agreed.

For the last twenty-four years, I took an all-inclusive holistic approach when advising entrepreneurs of fast-growth startups. But they were all men, and I know that struggle. How do I advise female entrepreneurs?

Share Your Thoughts

I would appreciate your feedback. Since I wrote this, I discussed this concern with the two entrepreneurs. Let’s just say, I was schooled. I have also interviewed other female entrepreneurs. I am learning and look forward to sharing in another post. In the meantime, share your experience with our community.

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Please note: I reserve the right to delete comments that are offensive or off-topic.

12 thoughts on “How Do I Advise Female Entrepreneurs?

  1. The reason this is tough for you is because you are a different type of adviser. You actually care about their family. Most VCs and Advisers don’t. This makes your job incredibly more difficult and more rewarding at the same time.

    I find it interesting the generation gap of of perspective on this. In your formative years men were at business school, men were the top executives, men were more wise as a whole about business. In my formative years (aka now), I would say the table has switched where I am generally more impressed with women then men (as a whole of course, every situation should be individualized).

    So here’s my advice: treat them no different than you would a man. The advice is the same. The critique is the same. The communication might need to be slightly different based on the individual (but that is true even for men). But treat them the exact same.

    BUT here’s the kicker. There will be moments where what you are advising them will feel weird or different. And instead of thinking you need to change the advice because it doesn’t fit because they are a woman, step back and ask yourself, have I been advising the men wrong all these years.

    Best example is mom guilt. It’s a term society has accepted, but shouldn’t their be such a thing as dad guilt? If we are honest with ourselves, don’t we know there is a thing as dad guilt? Isn’t dad guilt a bit why you became a VC and left corporate? So maybe what is true when advising a woman about mom guilt that you are learning now, should have been part of the “advice” all along for the men as well.

    In business, what is true for women is true for men, and what is true for men is true for women. But sometimes it takes a new perspective to realize a blindspot.

    I am excited for you in this. I think this is going to be really interesting.

    • Thanks for the insights and advice. The feedback I got from the entrepreneurs was the same as yours. Advise me the same as you would a male entrepreneur. I have mom guilt but I also know they have dad guilt. All true!

  2. Charlie

    This is a very interesting question. I have only provided business advice to one woman entrepreneur. That was 25 years ago when she was considering starting her own consulting business. She has been very successful in her business. She gives me a lot of credit for the advice that I have given her over the years, but her success was due to her work, effort and decisions, not my advice. The concept of advising her on her family life never really came up.

    You are a skilled, experienced business person. You, however, are not a skilled experienced therapist, minister etc. Are you not assuming too much control over them when you give advice on their decision making about their family life.

    I think the only thing you can do, and this would be maximum important, is to bring the subject up and then let them decide their own balance between business and personal life. That is what you would do for a male entrepreneur. Why would you even consider doing something different for a woman.

    You have the ability to be a powerful witness to others. It would be very beneficial for you to witness to them your own struggles with business vs family and suggest that they consider that as an issue to be discussed with their spouse early in the development of the business, so they as a couple can decide on the issues they will confront in the wife being a hard charging entrepreneur.

    What more can an advisor do than show the pot holes in the road ahead, so people can be prepared to successfully persevere.


    • I love it when you say, “What more can an advisor do than show the pot holes in the road ahead…” Great wisdom for any advisor. Thanks for taking the time to share your thoughts with the rest of us.

  3. I have been blessed to have my own business for 22 years – something I started so I could have flexibility to work and have a family, i.e. be home so I could be there when my daughter (and husband) need me. Sounds great on paper, but the honest to God truth is it’s hard to juggle at times and I have certainly experienced working mother guilt over the years – But the flip side is my daughter sees me as someone who is her own boss, a provider for our family and able to choose who I work with and how much – I am not a traditional stay at home mother nor am I a corporate career woman – I am an entrepreneur and have created a lifestyle career that has worked well for me thusfar. The balance comes as long as I am following God’s path for my life, not my own.

    • I agree with you. These women, however, are aiming to raise outside capital, eventually VC, and build a hyper growth business. You have done well managing your time between family and business by designing a lifesyle business. This is a great solution for your goals. I’m confused on their goals.

  4. Charlie this is an important topic. In my opinion, regardless of gender, the family needs to be onboard with the entrepreneur.
    The family needs to:
    1) know and agree on the company’s goals.
    2) be willing to support the spouse’s time commitment to the company.

    I’m blessed that my wife has always been very supportive of me in my entrepreneurial endeavors and now she is part of a startup and it’s my turn to support her. Either way, the two above item must be agreed upon.

    • Thanks for sharing. This is great advice. Success and the associated sacrifices must be agreed between the entrepreneur and the spouse. This is a real solution because you lived it. Thanks.

  5. Charlie, I read your article/post and I couldn’t help but think about two aspects of your ‘concerns’
    1. sounds eerily familiar to the arguments I have heard from time to time from ‘bosses’ and the execs in companies express in granting promotions to women to upper level management positions over male candidates because of the impact on their children and marriage as the work demands increase…. or even to give a basic promotion for a female newlywed over a male newlywed because it was anticipated the female would get pregnant and leave the company where as the male would need to increase his income to support his growing family. This by the way was in fact the discrimination I experienced while at IBM.
    2. your example of the mom / entrepreneur that built a company but lost her marriage and now is the single mom…. plenty of failed marriages and fractured families have been attributed to male entrepreneur/ceos who prioritized building their business over family involvement and many children have grown up without father figures that have been more committed to their jobs/careers than their families.

    I believe your concerns are better placed on the balance of family obligations and the support structure within the family and marriage, than about the sex of the entrepreneur. If your concerns about the future of the family is really the priority vs the role of the female in the family, ask to meet with the spouses too. Find out how much they support the commitment the wives are making to the business and how they manage the support of the children to nurture, encourage, and spend quality time not just quantity time .

    When I do my workshops about the need for the business plan for startup entrepreneurs, I tell them their FIRST investor is their family… not just financially but with their time because as an entrepreneur vs employee—they will likely miss some important family events, children ball games and recitals, many dinners and bedtime stories. IF the spouse believes in the business as much as the founder, then they will be a team to work together so that the family unit remains intact during those stressful early days of growth.

    • Thanks for taking the time to share you thoughts and, more importantly, your experience. I know your have helped shape my thinking and will help shape the thinking of the other readers of this blog. Thank you.

  6. Charlie,

    I too was struck by your article and was interested in reading everyone’s responses. In being on the opposite end of the spectrum and starting my career I think the answer is more simply give the advice you were asked for. I know I would be offended if I asked for advice purely on career or job steps and received a response regarding my personal life but likewise if I genuinely asked a professional contact how to handle my family life I would be sad if they weren’t honest with me about their impression- and sometimes that advice will vary based on my gender. But I respect that you’re in a difficult role because you have a wealth of advice to give in different levels and I think it could be hard to not mix them. Regardless I think it’s good things to think about. Love you!

    • Anna, Once again you prove yourself to be a clear thinking professional. This is excellent advice and I agree with you. My struggle is with the definition of the problem. Am I confused because of my male bias or because of my Biblical world view?

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