Building Entrepreneurial Courage Within: A Raw and Real Conversation with ChairmanMe Founder Sarah Lacy

Mar 8, 2022

Fierce. Fearless. Focused. Do these words ever hold more true than for our closing fireside keynote at the 2022 International Women’s Week kick-off event, The F-Factor: Fueling Women Founders.

We sat down for an up-close and unapologetically raw discussion with Sarah Lacy, former founder of Pando.com and now CEO and founder of Chairman Me, on her courageous public battle with Uber regarding the misogyny within the company’s culture. This tell-all chat was moderated by Manjula Selvarajah, Journalist, CBC National Columnist, CBC Guest Host, and Speaker.

Sarah Lacy is an unapologetic feminist, mother, and supporter of women. She’s been a journalist for nearly 20 years, known for her fearless, outspoken reporting. She’s been profiled in publications as varied as the New York Times and San Francisco Magazine and is a sought-after speaker and guest on national TV and radio. Her newest book, “A Uterus Is a Feature Not a Bug: The Working Woman’s Guide to Overthrowing the Patriarchy,” is part memoir, part manifesto on the power of working mothers.

Sarah is blazing with knowledge, from escaping the toxic culture in Silicon Valley to opening up her own company to empower women from all walks of life. She brings lessons learned throughout her career and entrepreneurial journey to help women escape the invisible chains of patriarchy.

Keep reading to learn:

• Valuable tips for fundraising in a male-dominated industry
• What mistakes not to make as a young female founder
• How to find the courage within
• The importance of building a diverse team early on

You have had many courageous and public battles with the likes of Uber as profiled in Time Magazine and the New York Times with headlines reading, Uber Executive Said the Company Would Spend ‘A Million Dollars’ to Shut Me Up. What was going through your mind when you heard what was happening?

For journalists, it’s easy for people to vilify us as nameless, faceless people, but at this moment, I wasn’t a nameless, faceless person to Uber. I was costing them money, and that was not okay with them. That was where their humanity ended. Uber had a detailed plan of exactly what they were going to try to do. Everything they already tried to do to silence me that works with other journalists hadn’t worked with me. So they used my family against me to try and shut me up.

In the history of Silicon Valley, this was never done before. There were a lot of publications that tried to whitewash this when it happened, saying that this is normal business. I’ve been a journalist at the highest levels in Silicon Valley for 20 years. I can say it was never done openly at a dinner that was part of a rehabilitation tour for Travis Kalanick (former Uber CEO) to convince journalists that he wasn’t as bad as they thought. One journalist, Ben Smith, had the courage to defy the ‘off the record’ rule at the dinner party and write about it, whereas other journalists stayed in silence, using my family as collateral damage for their access to the company.

In 2019, you sold Pando.com, publicly declaring that you were quitting journalism because of the toxic culture and history of harassment and threats. What lessons have come through this journey that helped shape you as a leader?

One of the most important lessons is to know that journalists are not your friends. Without names mentioned, looking back at what’s been written about companies like Uber, male journalists usually want to be like Travis Kalanick and think they are his friends. However, there is a reason that typically, women are the real investigative journalism leaders in Silicon Valley because they are the ones to call sh*t out!

Women journalists have been conditioned to have their guards up in male-dominated situations. And it’s difficult to be a journalist when you live in a place like Silicon Valley because you develop bonds and friendships with people. But, you have to know that there is a line to be drawn and a quid pro quo of a relationship when the stroke of keys can cost a company billions of dollars or make them billion dollars. So, you always have to have a filter up, and it’s an exhausting way to live. I’m glad I was always aware of that and never lost sight of it.

After 20 years in journalism, you launched ChairmanMe, a community for and of working women. What change are you trying to create with ChairmanMe?

I’m trying to create the same change that I was trying to create with journalism. But instead of tearing things down and exposing the bad stuff, ChairmanMe seeks to build something incredible that’s the opposite of the rest of the internet for working women.

Way too many women right now are living a life someone else wants them to live. So at ChairmanMe, we help women achieve the life they want to live, whether through unity, mentorship, or finding the right expert or advice. We’re helping to give women the mysterious keys to the kingdom that men pass down through mentorship, promotions, and male-dominated networks that have been cut out for women.

What are common mistakes that women founders make?

I noticed with younger female founders under 40 the desire to only pitch to women. However, if I had only pitched women VCs, I would not be in business right now. Less than 3% of venture money goes to women, and I beat those odds because I fundraised from men. Men are writing the checks to keep us in business, not women.

I do think the increase of women who have the power to write cheques in Silicon Valley and the world is great, but the reality is, it’s still a minority. Those people frequently have smaller funds and don’t have the pockets to continue to go deeper in funding rounds. And as a female founder, you will need that because you will never have the same ease of raising money as a man.

Have you been asked to, in some ways, act like a man when you try to make deals to raise capital?

One of the big pieces of internalized misogyny is female exceptionalism, like taking pride in hanging with the boys.

Definitely. One of the big pieces of internalized misogyny is female exceptionalism, like taking pride in hanging with the boys. I fell into that earlier in my career. I was the trope of a cool girl earlier in my career. I was frequently the only woman in a room, but people were fine with that because I was like, ‘one of the guys.’

I do caution women against trying to play the ‘bro game.’ The truth is, it doesn’t work. Women do not have the latitude to play the broken game. You can’t run on your numbers, and you can’t exaggerate your numbers. Women have to understand that they are playing a different game than men.

Give us a couple of tips that you think will be valuable for women to practice when fundraising?

First off, your network is everything, especially if you’re a female founder. Some studies show that unconscious bias falls away if a woman is in a known quantity. When I was younger in my career, I went to everything. Go to every dinner even if you don’t feel like going because these are all potential missed opportunities. You never know who you’re going to sit next to. Build your contacts and build real relationships because you never know when a relationship will help you.

Secondly, it’s all about the story. You’ve got to be able to hone your narrative. Don’t sound like everyone else. Finally, I think women need to embrace being polarizing. Being polarizing is vital to your story or narrative that will hook someone to invest in you. Being nice is not enough to get investment dollars. Being polarizing is standing for something and being consistent and persistent in what you stand for, even when that’s not a convenient stance to take. Being polarizing draws the right people to you like the most powerful magnet on Earth.

Women need to embrace being polarizing. Being polarizing is vital to your story or narrative that will hook someone to invest in you.

Can you weigh in on how founders can build diverse teams?

When you think about the wealth gap—not the salary gap—between men and women, it involves taking risks at those early stages and who can work for equity. It becomes compounded. It’s hard to hire underrepresented folks to work for equity in the early stages of a startup. If you’ve been systemically underpaid, you can’t always take the risk to work at a startup. This makes it even harder to hire diverse early teens than you would think based on the percentage of people of colour who could be a CTO or women of colour who have experience of being a CTO versus white men.

However, it’s very important to build a diverse team from day one because you can’t change your culture later. If you don’t do it initially, when will you prioritize it later?

What qualities do you seek and look for in your own trusted advisors?

I want people who will be honest and provide useful honesty. I like honesty that is constructive, actionable and useful. And I want someone who will be honest when it hits a purpose.

Being nice to people is another quality. Tell people what they are also doing well. I feel like so many boards, and advisors only tell you what you’re doing wrong.

How can entrepreneurs find the courage within and build this muscle?

The first thing is never to underestimate the power that you have. No matter who you are, someone looks up to you. It might be your kids, younger people at your company, or your students if you’re a teacher. Everyone has people who look up to them. We all have moments in our life where we have power and influence.

Also, think about your privilege and how you can extend that privilege. So, for example, if you’re working at a big company and you’re a white woman, you can advocate way more than women of colour because you have way more privilege, and constantly calibrating that is important.

And lastly, fail playing your own game. If I were to fail playing someone else’s game and according to their values, I’m never going to know if being true to myself is what would have made me successful.

The pandemic has had a disproportionate impact on women. 1 in 4 women is considering exiting the workforce or scaling back on their career. According to Pitchbook, many women entrepreneurs put off plans to start companies in 2020. What can women leaders do to help create a more equitable and sustainable future for women as we emerge from the pandemic?

We all have something we can do to help women—every single one of us.

Find something within your power that you can do to achieve impact. For me, during the MeToo movement, where decades of stuff we had normalized was coming to the surface, it was holding space in my house with monthly dinners for female founders and VCs. It was a safe space to talk about what we were dealing with daily. The ability to give people a monthly safe space to go to when they were going through things was incredible.

Also, if you can hire people, hire women. Hire people of colour. Hire underrepresented groups. Look for them and hold positions open for them. Pay them well and fight for the budget to pay them well. If you’re writing cheques, write cheques to underrepresented groups. There are obvious things you can do if you have power. But if your job does not give you power, I bet you have a dime or space to provide. We all have something we can do to help women—every single one of us.

What advice would you give yourself back when you launched ChairmanMe or Pando.com?

I would tell younger me to keep talking because many people would tell me to shut up my whole upbringing. But my words are what bought my houses and millions of dollars in California real estate. I was good enough at my job as a journalist that people had to listen. Gaslighting women out of their words is one of the most insidious things patriarchy does to us.

In terms of ChairmanMe, enjoy the ride because you don’t know the ending. Even if ChairmanMe was to be put out of business tomorrow, we have made permanent and lasting changes in thousands of women’s lives.

Gaslighting women out of their words is one of the most insidious things patriarchy does to us.

Listen to the recorded session of the F-Factor: Fueling Women Founders on our YouTube Channel, along with other inspirational IWW 2022 events.

Make the most of IWW 2022 by checking our complete March calendar of IWW 2022 events.

Catch all the actionable insight and inspiration of International Women’s Week! We are excited to come together with collaborators from our region, across Canada and around the world for this empowering month. Dozens of partners are joining us to promote women in leadership, host and contribute to events, and engage participants from Canada’s Capital and anywhere on Earth.