Good Founders Have Unapologetic Confidence + Tenacity: YC Female Founders Conference

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I attended the Y Combinator Female Founders Conference yesterday, the first event of its kind for the incubator. It was an oversubscribed, standing-room only event that took place in Mountain View and arguably it signals a change that caught me off guard.

It wasn’t that it was controversial. It was incontrovertible. Women are no longer an immaterial minority but rather a growing asset to the startup landscape. Everyone (man or woman) should understand the implications.

  • Although the audience was women, the conference was not focused women-centric issues. The theme was creating successful startups — speakers gave business-focused talks about solving real problems, monetization, and culture. They represented quality companies like Homejoy, Eventbrite, and VMware. There were some discussions around children and how being a woman can affect your success. But these were chapters in the novel of a conference where the thesis was about how to be a successful founder, not how to manage the negative implications of being a female one.
  • When asked the number of women in the audience who were founders, the majority raised their hand. The majority also raised their hand in response to how many were engineers. I was shocked it was so high.
  • The attitude was electric and positive. I’ve never seen such an enthusiastic audience. When Jessica expressed in a particularly vulnerable moment that she was nervous about the talk, someone shouted, “It’s AMAZING!” You don’t get that kind of support from most conference attendees.

BOTTOM LINE: It is clear to me that whether or not you choose to support the tide, the presence of female founders and women has already changed discourse in tech. We represent an untapped resource that is now pouring into the startup labor force and thought leadership. This is going to have massive implications for innovation and financing as we start to see an emphasis on understanding work-life balance, a renewed focus on traction vs. gender, and new discussions around internal culture.

All YC had to do was to set up an event but nothing in particular to wrangle or embolden the community (though I support Jessica in making this an annual event!). The community of women in tech is strong.

We are already here. And we are executing like crazy.

Below are my favorite pieces of advice from the speakers and you can watch the video here:

Jessica Livingston, Founder of Y Combinator

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34.5% of YC female founders have significant others for cofounders – This was a powerful statement (an anecdotal stat from her knowledge of YC founders, she admits), because it signals a changing forecast of the future composition of founding teams. She points out that while men in tech tend to start companies with other men who are their friends/peers from school, women often don’t have that personal network of engineers. An increasingly powerful source of technical talent for women is in their family and significant others.

Running YC is like running a startup – It’s funny to imagine YC as a startup because, as an entrepreneur, incubator programs like YC and 500 Startups are the low-acceptance, high-caliber programs that sometimes feel institutional. Frankly, we forget that YC was started in 2005 by 3 founders, and Jessica was one of them. She talked about being the non-technical co-founder and doing the Ops grunt work that many early-stage non-tech founders do — like delivering AC units to one YC’s first batches in the sweltering Massachusetts summer. She’s as scrappy as any of us, and it leant her credibility in my book.

You can combine work and life — it’s possible, but difficult – The slide she shared above is her “work-life balance” photo. She gave a nod to other speakers Julia Hartz (Eventbrite) and Diane Greene (VMWare), who had kids in the early stages of their startups. Jessica dove into the topic with hesitation, admitting that she was afraid to be controversial. I’m glad she shouldered the discussion and spoke candidly.

She claimed that when you have children, you don’t want to spend 12 hours working — you want to spend time with your kids. It really flagged an important topic for me when I approach that decision. I want to run companies the rest of my life, and now many women in tech do. We needs to be thoughtful about how we create that balance and who we picks as our partners to do it.

Adora Cheung, Founder of HomeJoy

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The first 1,000 days of Homejoy were the “Dark Ages” – No employees, lots of credit card debt, and $100 of revenue monthly: this is what the beginning looked like. NO ups, only downs. I’ve had the pleasure of talking to Adora one-on-one, and it’s refreshing to see her just as candid on stage.

They went through 13 separate pivots — a therapist marketplace, a celebrity gossip website, a “soul-sucking” content SEO play, etc. It wasn’t until her frustration with her co-founder’s dirty apartment forced them to find a cleaner, and she stumbled on the building blocks for Homejoy. But it didn’t just blow up from there. She then got a job as a cleaner herself after getting rejected for 2 weeks of interviews for the process, commuted from South Bay to the city on the daily, worked 8 hour days cleaning, coded in the evenings, then slept in her car to avoid the morning commute.

Now she’s raised over $40M in funding, does millions in monthly revenue, and has 1,000+ cleaners on the platform.

The clear takeaway is TO ENDURE. I loved her authenticity, and she had the audience in stitches with the hilarious portrayal of her scurrying around SF as a cleaner, trying to avoid people she knew.

Jessica Mah, Founder of inDinero

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Don’t run a company you can’t be happy with – Jessica’s story of starting inDinero begins with such momentum (hot financing, hot press, hot tub in office), that we were all on the edge of our seat. All the vanity metrics were growing, press was coming in like crazy, and the team was pumped on being the next Intuit.

It wasn’t until her mentor and professor, Steve Blank, came to visit that he advised her, “Don’t be afraid to pivot.” Jessica took a hard look at the market size and their ability to make a product that their customers care about and are willing to pay for. And the numbers just didn’t add up.

Jessica shared on-stage a 6AM e-mail she sent to her parents after a sleepless night. She said she felt like Bernie Madoff on the outside and needed to make serious changes to fix what was broken on the inside. We all laughed at the angst, but it was also incredibly moving. She had the courage not to live with her cognitive dissonance and instead make a difficult choice to let everyone go and re-think the entire operation.

Don’t be cocky, be unapologetically confident (and avoid office hot tubs) – Ironically, that office hot tub was the symbol of ego during her talk. She explains a transformation of her team focusing on vanity to focusing on customers. An office that goes from hot tub to humility.

A female VC shared with Jessica how investors were put off by her “strong personality.” At that point, Jessica shows a slide with her co-founder and her happily arm in arm. It’s a reminder that no matter what people say, you have to focus on what’s important — your team, your values.

She ends saying that she’s no longer cocky. But she is unapologetically confident. This is one of the most important traits any founder can have. And Jessica rocks it.

Julia Hartz, Founder of Eventbrite

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She is married to her co-founder and never knew anything else – The first question I’m sure most people ask Julia is how she maintains “work-life balance” when she’s married to her co-founder. She addresses the answer up-front by explaining how she started Eventbrite with Kevin when they were engaged, and she literally doesn’t know their married relationship in any other context. That doesn’t mean she wasn’t thoughtful about keeping their personal relationship strong, but that transition wasn’t as abrupt because it was de facto.

I draw a strong parallel because I did 2 startups in college, the second one that I got into 500 Startups for and now do today. When people ask me about this elusive balance, I tell them I literally have no other way of living my life. I think it’s a scrappy attitude many founders share.

Measure the satisfaction of your internal team – Julia is intensely focused on culture — I saw her speak on an Orrick panel about it, and that’s where I first learned the unique name for her staff: “Britelings” (gives me sort of a CandyLand, bubbly feel). She uses the Net Promoter Score, which is traditionally used to track customer satisfaction, to track Briteling happiness in the company. It’s a fantastic idea for quantifying culture, and she does this on a monthly basis.

Fundraising Panel

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If you wait until you feel “ready” to fundraise, you’ll never fundraise [Jamie Wong, Vayable] –  This is the #1 reason I see founders stumble in the fundraising process. As Jamie points out, you never actually wake up and say, “Today is the day I’m ready to fundraise!” She emphasizes getting in and getting out. Plan it in advance, make it a quick process, and get back to business.

Fundraising is painful and personal, it’s normal [Danielle Morrill, Mattermark] – Danielle shared her frustration in an interesting way. She explained how she wanted to be able to “turn herself inside out” to show investors what she saw of the future — if she could do that, then of course they would invest. Instead, it’s frustrating to rely on a deck tell the story. When you fail to communicate, it’s highly personal for a founder. We tend to internalize these failures and hold onto it until after the financing is over.

When I first raised money, I felt that same sense of isolation. I echo Danielle’s sentiment of being able to talk to other founders about it — even when you don’t want to bother your co-founders for a hug (which, I think, is totally acceptable).

Eli Sharef, Founder of HireArt

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Have confidence (especially as a woman) – This is a piece of advice I wouldn’t expect to hear from in a normal founder discussion. It’s simply assumed.

Eli shared her authentic story of when she thought HireArt would fail. Post-YC, all her batchmates had raised money and she hadn’t raised a penny. Sitting in her car, she got the email from Sequoia rejecting her and cried. She felt the heavy responsibility for her team and the failure of her “experiment.” Her co-founders told her to keep going — after having 70 meetings, go out and have 70 more. And eventually she did find the right investor who believed in her. And it took swagger and confidence to do it.

Kathryn Minshew, Founder of The Muse

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She was turned down by 11 accelerators before getting into YC – After so many rejections, Kathryn thought she was done — but an advisor told her to take one last shot and apply to YC. At this point, Kathryn and her team had been turned down by every single investor in NYC (investors told them “women in theirs 20s is a small market”). The interesting thing is her mindset even when they had been rejected 11 times and were looking at getting into one of the hardest incubator programs in the country — that no matter what, they were going to keep going.

They got into YC, have now raised over $2M in financing, and have grown a community that measures in the millions.

Diane Greene, Founder and former CEO of VMWare

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The humblest one in the room is often the most successful – I find it telling that she led with a humble story of starting a women’s hockey team. The team ended up using the old uniforms with the male hockey team and joining with women from Dartmouth to start. She then dove into a brief tale of her being a windsurfer.  I dug around and found that she, in fact, organized the first Windsurfing World Championship in 1974 and she was in fact a champion windsurfer.

Her great humility is evident in her speaking style — she leaned against the podium and was conversational. But she’s clearly one of the most successful. She led VMWare as the CEO for 10 years and it’s now a company that does over $4B in revenue.

Elizabeth Iorns, Founder of Science Exchange

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The most frequent question you’ll get asked is “Why did you start this?” – Elizabeth takes a unique spin on why it’s important to solve a real and personal problem — she frames it in terms of the #1 question you get asked as a founder. You get asked the founding story by potential hires, investors, customers, press all the time, and your most compelling answer is the genuine one.

There’s still a great deal of work to be done. Women only represent 17% of all computer science graduates and only 3% of tech startups are formed by women (Kauffman Foundation). Grassroots efforts like Pyladies, Girls Who CodeBlack Girls Code, and even this conference are all indicators of the movement that we’re already in the midst of.

I am thrilled for this to be an ongoing event. Thank you, Jessica Livingston, for having the courage to pull off an event as graceful and thoughtful as this one.

For all the women out there, keep persisting and walking with confidence.

If you went to the conference, I’d love to hear your commentary on if the dialogue was useful to you!

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