Lady Business: The ordinary money slog vs. fundraising while female; Why Drybar's Alli Webb wants to meet Michelle Obama

Hello and welcome to Lady Business, a weekly newsletter about women, the business world, and all the ways they overlap. You can sign up for Lady Business and read previous issues here. This is the forty-eighth issue, published November 1, 2018. 
 

Ordinary People

This newsletter is, by name and by intro, obviously focused on the realities of being a woman in the business world. And we’re in a boom time for headlines about that! Just this week: Google walk-outs, an epidemic of corporate diversity lip-service, record numbers of women running for office (please vote Tuesday), and one of the few women in federal power right now deciding that campus sexual assault isn’t a thing. (Please, please vote Tuesday.)
 
So there are plenty of specific challenges for women in business, more for women of color and queer women and trans women. But this newsletter is also, perhaps more quietly, interested in the fact that many aspects of business are universal. Leadership, management, finances, expansion, success or failure--these are often complicated by our sex and our identities, but it’s not like lady leaders spend their time only thinking about #MeToo while guys get to focus exclusively on stock price. (Well. I’d love to see a study of how much mental energy men vs. women have expended on fixing workplace harassment, but I digress.)

This is one reason I so enjoyed talking about fundraising with Jennifer Fitzgerald, the co-founder and CEO of New York–based insurance startup Policygenius. Fitzgerald started the company with a (male) subordinate at McKinsey, and she does have some fundraising-while-female war stories; even though she’s clearly the boss, one potential investor would only talk to her male cofounder during a pitch meeting. (“I've been in the business world for a long time, and I'd never seen anything like that before,” she recalls.)

But the bulk of Fitzgerald’s experience wasn’t that being a woman made fundraising hard; it was that asking people for money is hard for almost anyone:

I wish we had done more research on it, because we went into it with a little bit of hubris and a lot of naiveté. When you see company after company raising money, you get the outside-in perception: "It's not that difficult if they can do it." Which is not the case. We were two ex-McKinsey consultants, neither of us was technical, and we wanted to tackle insurance--every strike was against us. It was a very fruitless and frustrating few months.

…So we got off the VC track and just raised our seed round with a bunch of small checks from friends and family. Our target was $1 million. We fell short; we raised about $750,000, among about 50 different small investors. Which is a painful way to do it, but we had to get it done. 

Spoiler alert: She eventually raised some bigger checks, totaling $52 million, and made it onto Inc.’s 2018 Female Founders 100 list.
 

The Lady Business Interview: Alli Webb

 
As I mentioned last week, I sat down with Drybar co-founder Alli Webb at Fast Company’s Innovation Festival. Webb, who co-founded her chain of more than 110 blowdry salons with her brother, Michael Landau, told me about bad hair days, new projects, her dreams of meeting Michelle Obama -- and why she regrets some early Drybar design decisions.
 
Before you started Drybar, you and your brother had a track record of going into business before -- and it went really badly. Why do it again?
It's funny how that was an important thing for us to have gone through, because it made us know what not to do. We were very young -- I was in my early 20s, and we weren't doing something we loved. We were fighting. We were not happy. … But my parents weren't huge fans of me going to cosmetology school. They didn't really see it, but my brother did, and he was always very supportive of that. He really gave me the confidence to take the plunge and go to beauty school against my parents' better wishes. Even though they paid for it, they weren't into that decision. But, who's laughing now?
 
I hope you give them lots of Drybar products for the holidays.
Yeah, everybody gets [some]. I have two boys who are 11 and 13, and there's a lot of -- don't listen to this part John, who is our CEO back there. Sorry to put you on the spot, John! -- there's a lot of bribing that goes on for teachers. "Yes, give them whatever they want. It's fine, just for the grades!” Just kidding.
 
You often point out that your brother has no hair.
He loves when I do that.
 
But there are a lot of women-focused brands where male investors and male executives don't get the consumer. Anything from hair, to makeup, to fashion, to bras and tampons -- men say they have to ask their assistants, or their wives. Have you seen a change over the course of Drybar’s eight years in how men respond to female-focused business opportunities?
100%. I think there's been such a shift. I remember when we were first raising institutional money -- and we have great private equity partners now -- but I remember those early pitches, and going into talk to a room full of men in suits, and they did not understand me. And they didn't understand the business. At that point we only had maybe 10 or 11 stores, so we certainly weren't as established as we are now, but there was definitely this "I don't get it." Blank stare. I still hear that from my friends who are starting their businesses, that it is frustrating to walk into a room full of men. No offense to the men, but men don't get it. But I think that the climate is changing, and there's so many more investment groups and companies that are popping up that are female-led, and female-focused. I think the playing field is leveling out.
 
What’s your biggest piece of advice for women these days?
I could give lots of advice. I have lots of opinions. But I think the biggest thing is in terms of personal happiness, of doing something that you really love. I struggled for a long time, trying to find my thing. We didn't start Drybar until I was around 35, so you're never too old, for starters. But also, I've talked to so many women who are thinking about starting their own businesses, they have a great idea, but “there's too many things I don't know." Of course there are risks, and financial risks, and it's scary, and you have to have a lot of support from your family. It's a lot, but if it's a job that you want, or a career that you wish you were in but you're not, just do it. Do what makes you happy. It's so cliché, but I really believe in that. The last eight years have been so much work, but I don't think of it like I'm clocking into a job. It's all I think about, and it makes me excited, and want to get out of bed in the morning.
 
Is there anything that you had to say goodbye to as Drybar scaled and expanded? Anything that you miss from the very early days?
It was my idea to make these shops all white. Maybe not my best idea. They're very hard to keep clean, so we've gone to a beige chair, because probably everybody in here is wearing jeans, and we learn that blue jeans, the fabric [rubs off]. We used to have really funny meetings, "Can we ask everybody to wear a towel when they sit down? Is that weird?" Because we can't keep white chairs not looking crappy, because they get denim marks on them. But I was sad to not have white chairs, because when we open a brand new shop and everything is crisp and new, I love it so much.
 
You’re investing in other entrepreneurs, and working on a new business, and running a podcast. Do you have a dream guest?
If we're really dreaming, I think I'd like to have Michelle Obama or Oprah. Or Michelle Obama and Oprah. I grew up with watching Oprah. I've never actually met her. I have been at some of Michelle Obama's talks, but she's so bad-ass. She was just talking about how important voting is, and it was so impactful to me that she was telling young people: "You wouldn't allow your parents to post on your Instagram page, right? Or to pick out the sneakers you're gonna wear." And you're like, "God, no." "But you would allow them to make voting decisions for you?" She's just so awesome.

What do you when you have a bad hair day?
What? I don't have bad hair days! … Just kidding, I do. But I really try not to. I do feel pressure to have good hair all the time, and I try not to leave the house without good hair. …Even before Drybar, I was a big believer in you never know who you're gonna meet when, that you always should be at your best. That's kind of my life philosophy.

Lady Bits

--“This is not a thing. You can be chairman and CEO without having your website say “Chairman and CEO.” There’s no, like, legally binding effect of the website. It’s a website.” Bloomberg’s Matt Levine on some of Elon Musk’s latest antics. Related, congrats to Musk for getting his name dropped on The Good Place!

--"To be specific, Sandy, will you marry me this summer?" I’ve beaten up a bit on the Supreme Court of late, so will admit to being charmed by this story of how late Chief Justice William Rehnquist once proposed to his future colleague Sandra Day O’Connor – and how, despite her rejection, he remained her friend and supportive colleague. “Indeed, Rehnquist is said to have been one of those who privately suggested O'Connor to President Reagan as a potential Supreme Court nominee in 1981.”
 
--Programming note: Lady Business will be off on a reporting adventure next week. In the meantime: Please, please, please vote.
 
Thank you for reading, commenting, and subscribing to this newsletter! Please tell your friends to sign up here, let me know what you think about this week's issue, and what else you'd like to see me write about: maria.aspan@gmail.com