Lessons on Confidence, Criticism, and How to Thrive as an Underestimated Founder from Sara Blakely

Village Global luminaries Sara Blakley and Reid Hoffman, in conversation with Lisa Skeete Tatum

Last week, over 100 amazing female founders and funders from across the country gathered in Palo Alto to discuss this question: What’s it like to feel underestimated? And how can we build a network to help each other go farther in our entrepreneurial journeys and defy the odds?

We at Village Global were honored to host the event. We invited two of our LP luminaries, Sara Blakely, the founder of Spanx, and Reid Hoffman, the founder of LinkedIn, to kick off the day with a fireside chat moderated by Lisa Skeete Tatum, founder of Landit. We named the event Underestimated because as Sara once said, “People have often asked me what’s the best thing about being a girl in business, and what’s been the hardest? My answer is the same… being underestimated.”

Over a hundred entrepreneurs were nominated to participate in the event in Palo Alto

Being Underestimated Can Work In Your Favor

“In the beginning of Spanx,” Sara said, “being underestimated made it more challenging. But it also works so much in your favor. The competition didn’t take me seriously for a long time. And I think it’s really fun to prove people wrong.”

Reid said he loves to invest in founders that others may be misjudging: “The entrepreneurs I’m most likely to invest in are the ones that have gone and seriously tried, maybe failed, and are really hungry to play again because the market underestimates them.”

In a sense, all entrepreneurs are going to be underestimated in the first couple years of the journey, because if you’re pursuing a big, bold idea, a lot of people will not understand or agree with your strategy. “You can’t accomplish extraordinary things without doing something contrarian,” Reid told the group, “It goes from — everyone thinks you’re crazy and then suddenly everyone thinks what you’re doing is obvious and brilliant.”

Be Confident That You’ll Figure It Out

Spanx founder Sara Blakely met with a small group of Village Global founders backstage

In a small roundtable discussion with 7 of Village’s female founders and network leaders, Sara implored our founders to assert themselves: “Men get promoted on potential and women get promoted off results and part of it is because women want to wait to ask for the promotion or ask for the raise etc. until they feel like they are so prepared. They think to themselves, ‘I’ve got all the experience I need. I’ve already done this, I’ve already done that, and really good at that.’ Whereas men are much more confident to just be like, ‘I’ll figure it out. I’m going to take the leap.’”

Balancing the Feminine and Masculine

“I talk a lot about the feminine and masculine energy and leadership styles,” Sara said, “We all have masculine and feminine inside of us. The feminine energy and what the women are bringing is really important — intuition, vulnerability, collaboration. My mission is to elevate women and elevate the feminine is because I feel like it’s been so suppressed on the planet and when it’s more balanced, the world is going to be a much better place for all of us.”

Feedback Is a Gift — Seek It Constantly

Reid encouraged the founders in the room to demand feedback on how they can improve. “Feedback is a gift,” Reid said.

Sara shared an memorable story of receiving valuable, unsolicited feedback. She began her career selling fax machines door to door and one of her early prospective customers began to raise his hand seemingly at random. She’d be mid-sentence…and then his hand would go up. Here’s Sara:

I was so freaked out. I was like, does he have a nervous twitch that nobody told me about it? I started fumbling in my pitch and he stopped me and he goes, “Sara, I just want to mention this to you. You’re a great salesperson. Every time you say ‘I know’ it’s super distracting to your message.’
I had no idea that I was saying you know, you know, you know all throughout my pitch. I was so grateful. I went back to the office and told everybody, “Every time I say ‘you know’ — hold up your finger, let me know what I’m doing.”

Two amazing women from outside Silicon Valley joined us in Palo Alto to share their stories in front of the group.

Kat Cole’s improbable rise from working as a Hooters Girl to running a billion-dollar brand in under two decades is an incredible story of grit, service and hustle.

Intuition is a Magical Thing But Also a Mathematical Thing

Kat Cole, President, Focus Brands

“I think intuition is a bit of a magical thing,” Kat said, “But it’s also a mathematical thing when you can increase your exposure to data points. You’re just becoming much more informed and when you get used to seeing patterns and understanding when something is a consistent pattern versus a one off, it moves up in your priority of what to act on as a leader.”

When You’re Criticized, Assume For a Moment the Criticism is Accurate

You will be criticized your entire life as a young person, as a woman, as an entrepreneur,” Kat said, “You will be criticized daily, weekly, monthly, annually. The minute you’re criticized, assume for a moment first that the criticism is accurate. Actually have that be your first behavior and it is fascinating when you learn to shift the mindset of when you’re criticized, whether it’s by complaints from a customer and employee and investor. Assume it’s right, because then the pushback that you give is either, “Holy crap, they’re right and I’m not going to put my foot in my mouth. I’m going to be a part of the solution.” Or it is, “No, I stand my ground. I do what I do for this reason.” And you focus on communicating the why instead of debating the what.

Honor Your Roots But Don’t Let Them Define You

“My mom would write this on a card: Don’t forget where you came from, but don’t you ever let it solely define you,” Kat said. “Maybe where you start your business is a place to honor, but the very thing that will honor where and how you started will change radically over time.”

Sophia Amoruso is the founder of Nasty Gal, an eBay store she launched in 2006 at the age of 22, and author of #Girlboss, which has become a worldwide movement.

Don’t Compare Your Hustle To Their Highlight Reel

Sophia Amoruso, Co-Founder & CEO, Girlboss

“Everybody looks like they’re killing it,” Sophia said. “Your peers are going to raise money faster than you and be in TechCrunch sooner than you and they’re going to have the ring and they’re going to have the house and they’re going to have the baby. But behind the scenes, their babies are crying, the roof is leaking, and they are crying. It looked like I was winning at Nasty Gal. It really looked like I was winning…until I wasn’t anymore. So you never know what’s happening under the hood.”

they say to fake it till you make it. And I mean, I’m faking it right now. This is again, like the longest talk I think I’ve ever given, which is so crazy and it doesn’t make you a fraud.

Be Underestimated By Others, But Never Underestimate Yourself

“One of the most important lessons I’ve learned in the past few years is that we have to compete with ourselves, not with other people. Let others underestimate you. Let that be your fuel, but never underestimate yourself. Rewrite success on your own terms.”

Throughout the day, we were thrilled to have amazing women like Heidi Roizen, Selina Tobaccowala, Sonia Arrison, Elizabeth Weil and others moderate the brunch table conversations among the founders and VCs in the room.

We are eager to continue the conversation and of course, find and fund underestimated founders everywhere!

Are you an amazing entrepreneur working on a big idea?