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Episode Drop

#104 Dressd: Red Carpet or Red Ocean? finds us swimming in an industry where many companies have failed: clothing rental. Is Capri the founder to make it work? And if so, will the investors be able to overcome their fears to make it happen?

Vol. 1 Issue 5

Female founders have it rough. Unless they have a dude co-founder. According to TechCrunch "All-women teams raised 1.9% of VC funds last year, a percentage that skyrocketed to 17.2% when the team was mixed-gender. This trend has remained consistent for at least a decade."

Capri is a solo female founder, so based on that stat her chances of getting meaningful investment are slim. Capri also classifies herself as an introverted creative-type.

There's a moment in Episode 104 where Pitch Panelist Jillian Manus says, "Women have a disadvantage walking into a room, period, right away. And if you don't exude a level of sincere confidence and be able to put all your value out there... I think that you are going to lose a lot of people."

Charles Hudson responds, "I went in so quick because I'm like, 'I've seen this pattern - this human behavior pattern before.' Our portfolio's half female. We have a bunch of really smart female founders who just don't do the alpha thing."

I was hooked. What one VC saw as a weakness another saw as a strength.

I talked with Charles about this after Capri's pitch. He told me he invests in female founders like this all the time - founders who are maybe soft-spoken or unassuming. To some, these women are easily written off. It reminds me of how Neal described Capri, "Incredible founders have a way of hiding their power level.” But Charles sees what others don’t, and I have to wonder if VCs also pattern match for themselves.

Charles is an introverted Enneagram 9. You often don't hear a lot from him in The Pitch room, but when he talks everyone listens. You know Charles will have something powerful to say.

Jillian on the other hand wants to "feel that energy of a true inspirer who's gonna just get everybody lifting the team." Do you know who that sounds like? Jillian. She's the extroverted Enneagram 3. It's fascinating that each of these VCs is looking for people like them.

Last week I got on a call with Capri to get her input on all of this.

Do you feel like you were timid in the room and is that normal for you?

Yes, Jillian came up to me after the pitch and, and she said something to the effect of "You seemed really nervous and you weren't smiling. You didn't really introduce yourselves to us properly." And I was like, "You're totally right."

Unlike a demo day with an audience and a presentation, these investors are in the room to have a conversation. Capri said she needed to work on her interpersonal skills to really bring investors into her pitch.

I can attest to the fact that Capri was very nervous. I walk every founder to the door of the studio and send them in to pitch with a word of encouragement. Every single founder is nervous. When I held the door for Capri she actually stopped and turned around and told me, "I'm so nervous!" I reassured her that these are just normal people and she should pretend like she was meeting them at a dinner. Just shake their hands and introduce yourself. In she went.

Remember, most pitch meetings happen on Zoom calls these days. Founders aren't driving up Sand Hill Road to pitch in person. Covid cemented a new normal of pitching from the comfort of your home - your safe place. Now, add in the fact that a founder on The Pitch is pitching multiple VCs at once, and it is going to be recorded for all the world to hear.

So yes, Capri was timid, but she also said,

I think I'm good at pitching and good at persuading people, but it's not this... loud, boisterous personality that typically comes from me.
I think a lot of female founders tend to have a different personality than male founders, as well. We typically tend to be more introverted, reserved, creative types, as opposed to the more outgoing, outspoken type. But I think it's on the part of investors, as well, to realize that you get what you invest in, right? And there's a reason why male founders continuously raise hundreds of millions of dollars and then have to lay off their entire team.
It's because they don't manage capital responsibly. It's because they oversell themselves and almost lie to you in the fundraising process. And I've seen it. I've heard male founders tell me, "Oh, just tell investors this. Oh, just tell investors that your round is oversubscribed when it's not."

Capri puts it back on the investors.

Investors continuously get blindsided or bamboozled or infatuated with male founders who tell them what they want to hear. I think they need to realize that maybe they should want to hear something else.

Do you feel the pressure to portray something other than who you are?

Yeah, totally. All the time. All the time. And you know what, I find it really difficult because I do sometimes try to put on a show, or at least, change my personality.
I'm not gonna do the more dishonest things of fundraising that I just don't agree with. But I will sometimes chug a bunch of coffee, for example, before I go on a pitch meeting just to have a more outgoing personality. Then after six meetings in a day, I'm completely destroyed mentally and physically, and it's really hard to run other aspects of my business. I think I do struggle with the fundraising process for that reason. I think investors expect to see a certain type of person on the other end of the call.

Capri says she’s reading Built To Last: Successful Habits of Visionary Companies. Jim Collins and Jerry I. Porras studied the most visionary companies of the last century and they found there isn't one leadership-style or personality-type that makes a company successful. Debunking the myths they write, "A charismatic visionary leader is absolutely not required for a visionary company and, in fact, can be detrimental to a company's long-term prospects. Some of the most significant CEOs in the history of visionary companies did not fit the model of the high-profile charismatic leader - indeed, some explicitly shied away from that model."

I like that this myth has been debunked. As an introverted female founder I can relate to Capri.

Here’s to all the introverted female leaders out there. May you find freedom from others’ expectations and confidence in your unique ability to lead well.

Cheers, Lisa Muccio

Coming Up Next

Next week we are bringing you our last food product of the season. If you want to “Taste The Pitch” with investors, we have a special Pitch Pack that's Granola Guy approved. "Who's that?" you ask. You'll have to listen to Episode 105 to find out.

The Pitch News

This 3-min read by Pitch Panelist Charles Hudson is timely advice for the current episode and the current investment environment: Why Principles are more Important than Rules in Times of Great Uncertainty
The Pitch team had a big discussion about including a lemmings analogy in this week's episode. Producers and host were polling friends to determine if lemmings are widely-known or a niche cliché.

And just for fun here’s a lemming game found by our friend Benji (read: lemming expert.) You’re welcome. Lemmings: The Puzzle Adventure on the App Store
If you or someone you know is raising between 500K and 4 million dollars for a startup, you can apply to pitch on our show. We like all types of businesses - software, hardware, and consumer products. Pre-revenue is fine, but you do need to have some version of a live product that investors can demo. Pitches will be recorded live this June in San Diego, CA. Applications close April 30th.

Apply to be on The Pitch

Dressd is Looking for…

Investors
- Successful founders who have built in consumer, e-comm, marketplaces, p2p selling, resale, sustainable fashion tech, or fashion tech
- People who've built a viral referral engine into their product or helped scale a marketplace
- Strategic partnerships in the fashion industry, the festival industry, the cosplay industry, or event management
- People who have successfully scaled a company without any ad spend
Introductions to
- Faculty members - especially activities directors - at U.S. high schools. They are launching a program to give back to high schools when students rent prom dresses.
- Sororities to help expand their sorority program across the country

More information here on How to Invest in Dressd.

The Social Scene

To see video clips from all of Season 9 - including Dressd - follow The Pitch on Tik Tok, Instagram, Twitter, LinkedIn, YouTube, or Facebook.

That moment when I finally saw the faces I’ve been listening to for years 🙌🏻 😆 -Matthea Rentea on Tik Tok.

Shout Out

Thanks to Mark Phillips for stopping in our little Florida town this week to have lunch with me and Josh. You helped us lift our heads up from the daily grind and encouraged us to look ahead. You brought perspective and connected dots we weren’t able to see. Thank you for making the time and pouring out. Josh and I appreciate you!

The Pitch Insider

The Introverted Female Founder