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What I’ve Learned Advising Women Entrepreneurs … And Being One

women entrepreneurs small business holmes@law

I’ve advised startups for nearly 20 years. In 2015, I became one. There’s nothing like taking your own advice to prove its value. Admittedly, launching a business is humbling. We cannot know everything we’ll encounter. But, here’s a roadmap to a few key things I’ve learned, both from advising entrepreneurs and taking that leap of faith myself.

1. It’s Scary. If you’re frightened, you’re normal. This will be hard. There are plenty of reasons not to put yourself out there, and be vulnerable to criticism or failure. But you’re capable. Face the fear head on. Someone is watching you and will be inspired that you tried. Most importantly, that someone is you.

To help put the risks in perspective, gather good information, and have a written business plan. It will evolve. It should. But you must have a launching point, a guide for what you want to achieve, and structure around how you’ll do it. Lots of shiny objects will try to distract you. Having a plan helps you keep on track.

2. You Will Face Setbacks. Good. They happen on purpose. It’s uncomfortable, but it’s how you learn your business and improve. One great way to combat the disappointment of setbacks is to write down why things didn’t go the way you planned. Be specific so you can adapt. Just as significantly, keep track of what went right. Your energy is better spent focusing on opportunities ahead than lamenting went wrong.

How else can you improve? People who succeed in business are excessively curious. If I’m driving, washing dishes or doing laundry, I’m listening to podcasts. I constantly learn, take notes, and apply them either on behalf of my clients or with my own business. Thankfully, you’re not the first person to encounter most of your challenges, and the folks who’ve been there are willing to share their thoughts about how to navigate around some of the common landmines.

3. You Need Help. We never want to hear it, but this is … not negotiable. If you’re like me, you’d prefer to believe that you can develop a stellar plan and do it all on your own. Give me a moment while I giggle at how wrong I was about that.

I’ve benefited from having a sounding board, a cheerleader and a tough guy. My daughter is my sounding board for marketing ideas, business strategy … and reassuring hugs. One of my besties (with whom I actually was a cheerleading captain once upon a time) seems to tell everyone she knows, whether in person and online, “You should call Jo!”. And another of my dear friends is a no-nonsense realist. From him, I expect a very pragmatic “what are the numbers?”. I need all of them. With that support, I have the clarity and encouragement to be cheerleader, advocate and strategist for my clients.

4. Ask Advisors for More. I get genuinely excited talking to clients about business strategy. I ask about marketing, sales and logistics plans, input costs and margin preservation. Creative services and freelancer clients appreciate that I help them map how to protect what they create, get paid consistently, and grow recurring relationships with their customers. I’ve gone on ride alongs, celebrated with clients at new store openings, danced at their homes over the holidays, and texted them during off hours to help with strategy.

Why? Because business is hard, and I’m an advisor. My goal is genuinely to live the firm’s slogan – Your Business Ally™. And, all of your advisors (legal, financial and otherwise) should earn your trust by listening to you, understanding your goals, and being able to think beyond the immediate issue to help you identify opportunities. Ask for guidance from your advisors, and require a business ally.

5. You Can and Must Stand Up for Your Value. It’s uncomfortable. Yes. But necessary. Your talent is a terrible thing to waste. And if you don’t stand up for your value, then your business may dwindle to a hobby. Pretend that you’re advocating for a child you love, a dear friend, or an important cause. That’s somehow easier than being a proponent for ourselves.

Anticipate that your customers will say “I’m not one of the big guys. How can you fit my budget?” Great. They’re interested. If that customer is within your target audience, have something of value to offer them. But also have an appropriate product that’s the right fit for when they grow and have more resources. Likewise, be prepared with a premium product or service for higher end clients who have a bigger budget now. Either way, mind your margins. Profitability matters.

Here are a few practical tips for the negotiation. First, know your market and points of distinction. Be objective about that. If your prices are fair then explain why, and get comfortable holding your position. Second, people will pay for quality. You’ve got to convey the value of what you offer. Third, be mindful that you teach clients how to treat you. If you undervalue your product or service, why shouldn’t they? Fourth, consider whether this presents an opportunity to get your foot in the door, and renegotiate better later.

OK, you’ve got this! You’re a boss! And, if you need some help, don’t hesitate to reach out. In the meantime, here's our Resource Page for professional women and female business owners.


JoAnn Holmes ("Jo") is the founder of HOLMES@LAW, LLC. She serves as Outside General Counsel to select, intimate management teams for midsize companies. Likewise, Jo provides strategic support for lean law departments.

Jo founded HOLMES@LAW to provide agile, result-driven legal solutions. Beyond risk management, we help identify opportunities. The firm's focus areas are business law and strategy, commercial contracts and global intellectual property management. We build long-term relationships as trusted collaborators, and our flexibility consistently yields great value for clients.

HOLMES@LAW is also committed to service work, including through supporting local schools and leadership groups, as well as domestic and international charities. Since its founding, the firm has dedicated more than 200 hours to community service.

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Holmes, How … about the Disclaimers?

Information shared by JoAnn Holmes and/or HOLMES@LAW, LLC ("We or Us") is for educational purposes only. It is not legal advice. Each situation is unique, so the information We share may not be relevant to your circumstance. Until you enter a formal engagement agreement with Us, We are not your legal counsel, and no attorney-client relationship exists. So, please do not share any confidential information with Us, and please only interact with Us if you agree to these ground rules. Thanks!

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