Lindsey Taylor Wood: “Keep going”

Everything I do is driven by the idea that if women had more money they would have more power. And if women had more power we would live in a far more equitable, just, and inclusive world. That’s my north star. As a part of our series about strong female leaders, I had the pleasure of […]

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Everything I do is driven by the idea that if women had more money they would have more power. And if women had more power we would live in a far more equitable, just, and inclusive world. That’s my north star.

As a part of our series about strong female leaders, I had the pleasure of interviewing Lindsey Taylor Wood. Lindsey one of the White Ribbon Alliance for Safe Motherhood’s 20 Young Champions for Women, brings over 15 years of experience as a leader in the gender equality movement to The Helm — a lifestyle brand and venture firm elevating and investing in female entrepreneurs. Since 2018, The Helm’s venture fund has invested close to 1.5 million dollars in 11 of the most promising female CEOs in the country. This Spring, they launched an eCommerce platform that connects you directly with your favorite female-founded companies, products, and services. An expert in the empowerment of girls and women, Lindsey was the Founder & President of LTW, an impact studio with an emphasis on contemporary feminism. Her ability to use philanthropy and culture symbiotically, and with a gender lens, made her a sought-after strategist in the women’s rights movement. Along with LTW, Lindsey was on the founding team of Catapult, a crowdfunding platform for girls and women; worked for Women Deliver, a leading global advocate for girls’ and women’s health, rights, and wellbeing; contributed to a variety of campaigns centered on conflicts in Central Africa, as well as “The Enough Moment,” a book by John Prendergast and Don Cheadle; serves on the Board of Directors; and recently advised the Elizabeth A. Sackler Center for Feminist Art on the Brooklyn Museum’s seminal conference The Brooklyn Conference: Inspiring Social Change.

Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

After a decade in philanthropy focused on the advancement of girls and women, I became disenchanted with the lack of progress. I just wasn’t seeing the type of impact that I believed was possible and, given that, I couldn’t understand why philanthropy was the only way we were investing in equality. So, I spent a year trying to answer that question and arrived at a few key insights 1) only 2.2% of all venture capital went to women, 2) while men tend to invest, women tend to give, and 3) when women are at the decision-making table, more capital is directed towards women and minority built and owned companies. At that point, I set out to make it easy for women to invest in women. We do that in a variety of ways, including our venture firm and our eCommerce platform.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Funny is a strange frame when I think about mistakes… the pressure is so high stakes when you are starting out (and even now!) that I’m not at the point where I have enough distance from them to find them funny. Hopefully, that changes soon. I’ll report back!

OK, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO or executive that most attracted you to it?

I never set out to be a CEO. I wanted to create change in the world in the form of a company that didn’t exist, and here I am.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO But in just a few words can you explain what a CEO does that is different from the responsibilities of the other leaders?

Someone once told me that a CEO’s top three priorities should be vision, culture, and capital. More and more that rings true for me. It’s when you diverge from those that things tend to go sideways.

What is the one thing that you enjoy most about being an executive?

Having the privilege to build a values-driven company and to live everyday in the service of something I truly believe in.

What are the downsides of being an executive?

There’s a reason people say it’s lonely at the top. No one can ever understand what that truly means until they live it themselves. I think that founders and CEOs are held to an impossible standard by nearly everyone, and for those of us who are empaths and/or perfectionists, you have to be really careful about protecting yourself; women especially. I don’t think anyone has captured this dynamic more beautifully than Roosevelt’s “the critic who counts.”

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

Hmm… I don’t know if anything I’ve encountered is a myth per say… we all have our lived experiences. Every company, industry, stage, team, and/or investor community is different. If anything, I think I’ve realized through the experience of our founders and well as my own that the experience isn’t singular.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Oh, goodness. Everything! Only 2.2% of venture capital is directed towards women; it’s even less for women of color. You are held to a wildly different set of traction-oriented standards. You are more susceptible to scrutiny both internally and externally. Even advertising becomes as evidenced by companies like Unbound and Dame’s #campaign. These are the harsh realities.

What is the most striking difference between your actual job and how you thought the job would be?

I never anticipated how hard it would be to money and build a company at the same time.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

It’s tricky because you often see the mythologizing of success stories or the take downs but you rarely see accurate depictions of what it takes to build a company. And I offer that preamble because I wonder if part of the reason that people get so buried is that they don’t fully understand what it takes to ideate, capitalize, and execute on something that’s never existed in the world before. Founders have to be able to handle extremely high stress for extended periods of time. You have to feel energized rather than defeated by the unknown; the opportunity versus the obstacle. You have to be able to hear ‘no’ hundreds of times and still believe a ‘yes’ will come, and you have to be able to withstand judgment and feedback from various people all of the time. However hard you think it’s going to be, 10 times it. However much time you think it’s going to take to raise or build it, 10 times it. It’s not for the faint of heart.

What advice would you give to other female leaders to help their team to thrive?

Culture has been the hardest thing to get right and the thing I’m unwilling to compromise on. I care deeply about every single person on my team. My hope is that them knowing that motivates them. I’ve also noticed that when I’m in closer relationship with them, when I take the time for one-on-ones, to hold space for their needs and concerns, and to offer insight into my own scope of work and experiences, even if they don’t report to me directly, people are happier and more energized. I’m also in the process of hiring a coach for myself and one that will meet with our team in the New Year to help me better identify any areas where I can do a better job. I’m looking forward to seeing how that goes. But really, I’m still learning. And the only advice I can offer is something I’m trying to live more myself: you have to lead in a way that feels authentic to you.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are three people without whom this company wouldn’t exist. The first is Ruth Ann Harnisch, someone I’d worked with prior to starting The Helm. She was one of the first people to believe in me and to put her name and money behind me too, including being the first money invested into The Helm. The second is Shelley Kuipers. She’s an investor that has really, truly bought into this vision and has not only shown up in big ways herself but helped me to build an entirely new community of investors. The last person is our COO Juile Weber. She is the grounding force that keeps the train on the tracks each and every day. Her job is often thankless (as it relates to the outside world), but she’s the tie that binds for this company.

How have you used your success to make the world a better place?

In the year since we invested in our first 11 portfolio companies they have gone on to raise 27+ million dollars in capital. Those companies include Haute Hijab, a D2C lifestyle brand for Muslim women; Tia, a new model for women’s health care; and Rebellyous Food, a plant-based chicken alternative; among others. We’ve also launched an eCommerce site that elevates and sells 100+ female founded brands. In a world that wasn’t built for us, these companies are. They are changing the game. They stand for something. They lead with their values without compromising a financial return. The Helm’s ability to help propel them, even in the smallest of ways, drives me each and every day.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Keep going.
  2. Keep going.
  3. Keep going.
  4. Keep going.
  5. Keep going.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Everything I do is driven by the idea that if women had more money they would have more power. And if women had more power we would live in a far more equitable, just, and inclusive world. That’s my north star.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s the one I spoke to above: keep going. I know it sounds so simple, but I read an interview with Sweeten founder & CEO Jean Brownhill at a time when I really didn’t think I could keep going and it’s been my mantra, an actual chant in my head and in my heart that I return to on the days when it’s the hardest, ever since. At the end of the day, it’s all you can do. Keep going.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Oprah. Because, Oprah. But also because she was one of the first women who really understood her own worth and how to translate that into equity. It’s interesting, she’s so frequently viewed through the lens of talent and celebrity but rarely through the lens of business despite the fact that she’s a true pioneer.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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