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How To Build A Goddamn Empire with Entrepreneur Ali Kriegsman · QUESTION EVERYTHING

• 0:00
  Speaker 1: The following podcast is a dar Media production.
• 0:03
  Speaker 2: Do you want to start a company but have no
• 0:05
  Speaker 2: idea where to begin, or do you have dreams of
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  Speaker 2: becoming an influencer while the Life with Marianna podcast is
• 0:11
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  Speaker 2: influencer and co founder of the Clean skincare line. Summer Fridays,
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  Speaker 2: advice for you to live your best life. Make sure
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  Speaker 2: to tune in and subscribe to my podcast and follow
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  Speaker 2: me on Instagram at Marianna underscore Hewitt to see what's
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  Speaker 2: coming up each week so you don't miss an episode.
• 0:39
  Speaker 3: Big things happen when you're pretty, pretty bold, pretty clever,
• 0:44
  Speaker 3: pretty strong. I'm Danielle Robe and each week my guests
• 0:48
  Speaker 3: and I have conversations that put a new spin on
• 0:51
  Speaker 3: pretty This is pretty smart. Entrepreneur Ali Kriegsman wants to
• 0:59
  Speaker 3: help you build a goddamn empire.
• 1:02
  Speaker 4: Those are her words, not mine.
• 1:04
  Speaker 3: She's the co founder of Bulletin, a venture back retail
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  Speaker 3: technology startup.
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  Speaker 4: She was named a Forbes thirty Under thirty recipient.
• 1:10
  Speaker 3: And one of the most creative people in business by
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  Speaker 3: Fast Company.
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  Speaker 5: I'm a ruthless salesperson, self taught publicist, marketer, and growth strategist,
• 1:19
  Speaker 5: and have experienced scaling both D two C and B
• 1:21
  Speaker 5: to B companies. As a creative I've conceptualized and launched
• 1:25
  Speaker 5: six pop up stores, dozens of ad campaigns, influencer marketing programs,
• 1:30
  Speaker 5: and built and evolved Bulletin's brand voice over the past
• 1:33
  Speaker 5: five years.
• 1:34
  Speaker 3: Her book is both a relatable how to guide and
• 1:36
  Speaker 3: a candid personal diary of how to build a brand
• 1:39
  Speaker 3: and run a business. She doesn't gloss over any of
• 1:43
  Speaker 3: the hard stuff.
• 1:44
  Speaker 5: I entered entrepreneurship with a completely warped vision of what
• 1:49
  Speaker 5: entrepreneurship was. I had read books like Girl Boss and
• 1:53
  Speaker 5: Lean In, where it just kind of portrays a very glamorized,
• 1:57
  Speaker 5: inaccurate version of entrepreneurship. That is the true, lived, real
• 2:01
  Speaker 5: experience that all of us go through every day today.
• 2:04
  Speaker 3: We chat about it all, including when and how to
• 2:06
  Speaker 3: fake it till you make it, imposter syndrome, raising capital,
• 2:10
  Speaker 3: building a brand story and I asked her if Girl
• 2:13
  Speaker 3: Boss culture helped her or hurt her. She shares the
• 2:17
  Speaker 3: pros and cons you might not expect when growing your business,
• 2:20
  Speaker 3: and how glamorizing entrepreneurship on social.
• 2:22
  Speaker 4: Media hurts everyone, especially women.
• 2:27
  Speaker 3: Ali, you wrote a book called How to Build a
• 2:29
  Speaker 3: Goddamn Empire. You call it both a relatable how to
• 2:32
  Speaker 3: guide and a candid personal diary.
• 2:35
  Speaker 4: We're going to get into all of it.
• 2:37
  Speaker 3: One thing I really really love an admire about you
• 2:40
  Speaker 3: is you're not afraid to get candid. You kind of
• 2:42
  Speaker 3: live in the mess of everything, which is the exact
• 2:46
  Speaker 3: opposite of what I thought your book would be about.
• 2:49
  Speaker 5: I know, all right, it's it's a trojan horse. I
• 2:53
  Speaker 5: guess you're going to buy it for the girl Boss
• 2:55
  Speaker 5: vibes and then open it and realize it's something a
• 2:57
  Speaker 5: little bit different than what you expected.
• 3:00
  Speaker 3: Well, you know, it was so funny because I want
• 3:02
  Speaker 3: to be candid with everybody. When we connected, I almost
• 3:06
  Speaker 3: I was like, I don't know if this is a
• 3:08
  Speaker 3: right fit for Pretty Smart, because I'm like anti girl
• 3:12
  Speaker 3: Boss culture. We aired Lee Stein's episode and she's kind
• 3:17
  Speaker 3: of like the anti millennial pink, which is the esthetic
• 3:20
  Speaker 3: of girl Boss culture. And I said, we got to
• 3:23
  Speaker 3: hop on the phone, and as soon as we spoke,
• 3:27
  Speaker 3: not only did you surprise me because you too were
• 3:31
  Speaker 3: pushing up against sort of this glossy entrepreneurial image. But
• 3:37
  Speaker 3: you also made some good points that changed my mind
• 3:40
  Speaker 3: about things, and so I hope that we can kind
• 3:44
  Speaker 3: of debate and get candid today.
• 3:46
  Speaker 5: Yes I am, I'm a little nervous, but I'm excited.
• 3:50
  Speaker 5: I also just did an event with Lee Stein last night.
• 3:52
  Speaker 5: I met her through her kind of antique girl boss ethos,
• 3:57
  Speaker 5: and I read her book Self Care and related to
• 4:00
  Speaker 5: those characters a little bit more than I wish I did.
• 4:05
  Speaker 5: But I'm a huge fan of hers, and I think
• 4:07
  Speaker 5: she and I share a very similar perspective. So ready
• 4:11
  Speaker 5: to dive in and yeah, eager to get as candidate
• 4:13
  Speaker 5: as we can, and hopefully I won't embarrass myself or
• 4:17
  Speaker 5: get canceled.
• 4:17
  Speaker 4: We'll see none of the above.
• 4:19
  Speaker 3: I was startled by how smart you were, but I
• 4:23
  Speaker 3: want to, like, I kind of want to start from
• 4:24
  Speaker 3: the beginning. So you started a company called Bulletin, and
• 4:28
  Speaker 3: you then sort of stepped away from it. So take
• 4:31
  Speaker 3: me back to when you started Bulletin. How old were you,
• 4:35
  Speaker 3: why'd you start it, and how'd you get going?
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  Speaker 4: Yeah?
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  Speaker 5: Well, first, thanks for having me and excited to talk
• 4:42
  Speaker 5: about the book and talk about Bulletin. This is just
• 4:45
  Speaker 5: a great opportunity and I appreciate it a ton. I
• 4:48
  Speaker 5: started Bulletin when I was twenty four. I was the
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  Speaker 5: number one sales executive at the startup where I was working,
• 4:55
  Speaker 5: and I had been on financial aid in school. I
• 4:58
  Speaker 5: write about it in the book, but my fam went
• 5:00
  Speaker 5: through a series of medical crises and emergencies, a horrible divorce,
• 5:05
  Speaker 5: and I basically went from admittedly like a super privileged
• 5:09
  Speaker 5: LA life to a life that I didn't recognize and
• 5:12
  Speaker 5: one that was definitely a bit more scrappy.
• 5:15
  Speaker 1: And that meant that making.
• 5:17
  Speaker 5: Six figures as a salesperson was mind blowing to me.
• 5:21
  Speaker 5: At this startup, I was able to help put my
• 5:23
  Speaker 5: brother through school, pay off my own loans. The money
• 5:27
  Speaker 5: that was coming into my account commission wise was like
• 5:30
  Speaker 5: more money than I had ever seen in my life.
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  Speaker 1: I had gone from making.
• 5:33
  Speaker 5: Ten dollars an hour to getting like twenty thousand dollars
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  Speaker 5: commission checks put in my bank account every quarter. That
• 5:39
  Speaker 5: being said, even though I thought, because of what happened
• 5:43
  Speaker 5: to my family and our financial situation, that I'd really
• 5:46
  Speaker 5: be seeking that financial stability it wasn't enough for me,
• 5:49
  Speaker 5: and I was really unhappy at my job. My sales
• 5:52
  Speaker 5: job was just starting to feel extremely repetitive. And my
• 5:56
  Speaker 5: friend Alana, who worked at the company with me, had
• 6:00
  Speaker 5: the idea of coming up with a shoppable newsletter where
• 6:03
  Speaker 5: you could learn about cool emerging designers and shop their
• 6:06
  Speaker 5: work throughout the newsletter and then on our e commerce site.
• 6:09
  Speaker 5: So it was just a fun side project. I said yes.
• 6:12
  Speaker 5: I was like, oh, maybe this will be a chance
• 6:14
  Speaker 5: to do something a bit more creative, build out my
• 6:16
  Speaker 5: writing portfolio. And we started working on it on nights
• 6:19
  Speaker 5: and weekends, and then I just became obsessed. I mean,
• 6:22
  Speaker 5: I kind of saw Bulletin as my way out of
• 6:24
  Speaker 5: this nine to five, very regimented, kind of routine sales job.
• 6:29
  Speaker 5: And I won't go into all the crazy details of
• 6:31
  Speaker 5: our pivots, but we ended up applying to a program
• 6:35
  Speaker 5: that ended up giving us twenty thousand dollars, and in
• 6:38
  Speaker 5: exchange for that twenty thousand dollars, had to quit our
• 6:40
  Speaker 5: full time jobs where we were making, you know, in
• 6:43
  Speaker 5: the massive six figures and dedicate ourselves to building Bulletin
• 6:47
  Speaker 5: full time. So we ended up taking that leap of
• 6:50
  Speaker 5: faith I became the second full time at Bulletin in
• 6:52
  Speaker 5: early twenty sixteen, and we ended up doing pop up
• 6:56
  Speaker 5: markets to supplement the e commerce newsletter. We ran pop
• 6:59
  Speaker 5: up market in this massive eighteen thousand square foot parking
• 7:02
  Speaker 5: lot in Williamsburg for ten months straight, every single weekend,
• 7:05
  Speaker 5: working seven days a week, setting up the tents and tables,
• 7:08
  Speaker 5: taking them down on Sunday nights. We eventually pivoted from
• 7:11
  Speaker 5: pop up markets to permanent stores. We opened a total
• 7:14
  Speaker 5: of five stores in New York City over the course
• 7:16
  Speaker 5: of two and a half years. All of those stores
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  Speaker 5: were independently profitable. We built a beloved consumer brand that
• 7:21
  Speaker 5: was actually very rooted in the girl box ethos, which
• 7:24
  Speaker 5: I know we'll go into. One of the most popular
• 7:27
  Speaker 5: articles on Bulletin by Fast Company was like feminist retail
• 7:30
  Speaker 5: tech company. Bulletin is like reinventing brick and mortar retail.
• 7:34
  Speaker 5: I'm like, what is a feminist technology company? We ended
• 7:37
  Speaker 5: up building and launching our own wholesale marketplace at the
• 7:40
  Speaker 5: end of twenty nineteen.
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  Speaker 1: That's the business we've been running ever since.
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  Speaker 5: We connect independent brands all around the US and Canada
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  Speaker 5: with thousands and thousands of independent retailers also in the
• 7:51
  Speaker 5: US and Canada that are looking to source inventory for
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  Speaker 5: their physical or online stores. So we used to run
• 7:57
  Speaker 5: our retail stores and we it heard from so many
• 8:01
  Speaker 5: brands that it was super expensive and cumbersome to expand
• 8:04
  Speaker 5: their distribution. Me and Alana felt like it should be
• 8:07
  Speaker 5: just as easy to get a retail partner as it
• 8:09
  Speaker 5: is to launch on Etsy or Shopify.
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  Speaker 1: Why is this so hard?
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  Speaker 5: And we decided to build a tech platform that basically
• 8:14
  Speaker 5: connected brands with these new distribution partners all over the US.
• 8:18
  Speaker 5: And yeah, we just entered Canada last year, so it's
• 8:21
  Speaker 5: been a winding journey. And I think that's kind of
• 8:23
  Speaker 5: what my whole feel is. That's what my book is about.
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  Speaker 5: I think a lot of the most famous female entrepreneurs,
• 8:31
  Speaker 5: even if it's you know, the founder of Spanx or
• 8:33
  Speaker 5: Whitney from Bumble, they started out with the idea and
• 8:37
  Speaker 5: that's the idea and the business that they're still running today.
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  Speaker 5: But for most entrepreneurs, regardless of your gender or how
• 8:43
  Speaker 5: you identify, it's such a much more complex and rocky road.
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  Speaker 5: And you don't find product market fit immediately, you don't
• 8:49
  Speaker 5: start scaling immediately. People don't fall in love with you immediately,
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  Speaker 5: and that leads to a lot of anxiety, depressive episodes,
• 8:57
  Speaker 5: self doubt, imposter syndrome.
• 8:59
  Speaker 1: And I feel like so many of our.
• 9:01
  Speaker 5: Entrepreneur role models that we all know, those household name founders,
• 9:05
  Speaker 5: aren't talking about that, and so sometimes it feels like
• 9:09
  Speaker 5: other founders have some sort of playbook or intelligence or
• 9:12
  Speaker 5: insight that we don't have, when really I think that
• 9:15
  Speaker 5: most entrepreneurs, even the most well known and famous ones,
• 9:18
  Speaker 5: go through this rocky road and they're just not talking
• 9:20
  Speaker 5: about it. So we all feel alienated, but at the
• 9:23
  Speaker 5: same time, we're all going through the exact same thing.
• 9:26
  Speaker 5: But I think the story of Bulletin's crazy ebbs and
• 9:28
  Speaker 5: flows and pivots is directly what informed the book and
• 9:31
  Speaker 5: my message about accepting mess, accepting failure, and letting.
• 9:35
  Speaker 1: It be part of your journey.
• 9:36
  Speaker 3: I have so many questions, first of all, for people
• 9:42
  Speaker 3: like me who don't understand some of the buzzwords.
• 9:46
  Speaker 4: Yeah, would you say that?
• 9:47
  Speaker 3: So Bulletin now as it stands, connects brands that are
• 9:51
  Speaker 3: selling really unique things cards or T shirts, whatever, and
• 9:56
  Speaker 3: it connects them with brick and mortar retailers or online retailers.
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  Speaker 5: So Bulletin's platform connects independent brands that are selling everything
• 10:04
  Speaker 5: from stationary and cards to your point to apparel, beauty accessories,
• 10:09
  Speaker 5: and connects them with independent retailers in the US and
• 10:12
  Speaker 5: Canada that are looking for that inventory. So if you
• 10:14
  Speaker 5: think about the tiny shops on Melrose, or some of
• 10:19
  Speaker 5: the independent retailers in Santa Monica, if you think about
• 10:22
  Speaker 5: even like Arawon, like an independent grosser, those retailers use
• 10:26
  Speaker 5: Bulletin to get that stuff on their shelves.
• 10:28
  Speaker 1: That's probably the easiest way to put it.
• 10:30
  Speaker 4: That's so smart.
• 10:32
  Speaker 3: You said something in your book, starting a business can
• 10:35
  Speaker 3: just mean monetizing a hobby, and that's something you can
• 10:37
  Speaker 3: do on your own terms and on your own time.
• 10:40
  Speaker 3: It sounds like yours kind of started out as a hobby,
• 10:42
  Speaker 3: even though you had a business plan. How do you
• 10:45
  Speaker 3: know when it's a hobby versus a full blown business.
• 10:48
  Speaker 1: I think there's usually an inflection point.
• 10:51
  Speaker 5: I think that if you start out pursuing your entrepreneurial
• 10:57
  Speaker 5: effort as a hobby, you'll notice if you like it
• 11:01
  Speaker 5: a little bit more than you should. I think for me,
• 11:04
  Speaker 5: like reading is a hobby or cooking dinner is a hobby,
• 11:08
  Speaker 5: but I'm not becoming obsessed with the ingredients or like
• 11:12
  Speaker 5: making a certain dish like so much better every single.
• 11:15
  Speaker 1: Time I make it.
• 11:16
  Speaker 5: I'm interesting, you know, writing reviews about all of the
• 11:20
  Speaker 5: different books that I'm reading on Sundays. And I think
• 11:23
  Speaker 5: when something goes from like hobby to obsession and something
• 11:27
  Speaker 5: that you want to constantly optimize and do better as
• 11:30
  Speaker 5: time goes on, that to me is the signal that
• 11:33
  Speaker 5: there might be a business here, or there might be
• 11:35
  Speaker 5: a way for you to monetize this and get a
• 11:38
  Speaker 5: lot of fulfillment.
• 11:39
  Speaker 1: Enjoy in this hobby.
• 11:40
  Speaker 5: I think that for a lot of people, they pursue
• 11:43
  Speaker 5: that hobby on a part time basis as a side
• 11:45
  Speaker 5: hustle or something they chip away at, or maybe it's
• 11:49
  Speaker 5: there in between jobs and it's something that they're just
• 11:51
  Speaker 5: giving a try. I think there's a certain inflection point
• 11:54
  Speaker 5: where you either see so much demand that kind of
• 11:58
  Speaker 5: continuing to do this dance full time plus side hustle
• 12:01
  Speaker 5: just is not going to set you up for success.
• 12:04
  Speaker 5: You're kind of gonna is this an explotives allowed for
• 12:07
  Speaker 5: the situation? Totally, You're gonna fuck up. You're going to
• 12:10
  Speaker 5: fuck up your side hustle. If you're turning people away
• 12:14
  Speaker 5: because they love what you're doing, but because of your
• 12:17
  Speaker 5: full time job, you can't meet the demand, I think.
• 12:19
  Speaker 1: That's one signal.
• 12:20
  Speaker 5: I think the second signal is more personal, and it's like,
• 12:23
  Speaker 5: how miserable are you not doing this thing? So for
• 12:26
  Speaker 5: me with Bulletin, I fell so in love with these
• 12:28
  Speaker 5: small businesses and these brands and learning about them and
• 12:31
  Speaker 5: telling their stories that I kind of knew deep down
• 12:34
  Speaker 5: that we might not be able to scale this like
• 12:36
  Speaker 5: cute newsletter that we had started. But I was ready
• 12:39
  Speaker 5: to go off the deep end because I knew that
• 12:41
  Speaker 5: I'd be working with this customer no matter what, and
• 12:45
  Speaker 5: the idea of building something from nothing just became something
• 12:47
  Speaker 5: really attractive to me.
• 12:49
  Speaker 1: And I was so over my sales job.
• 12:50
  Speaker 5: So I think there's kind of like two cues of
• 12:53
  Speaker 5: when to go full time and.
• 12:54
  Speaker 1: Turn it into a full blown business.
• 12:56
  Speaker 5: One is, is there so much demand and you can't
• 12:59
  Speaker 5: meet it because you're just so overwhelmed by your full
• 13:01
  Speaker 5: time job. The second one would be are you just
• 13:04
  Speaker 5: so over your full time job that like you don't
• 13:07
  Speaker 5: really want to focus it on it anymore, You're not
• 13:09
  Speaker 5: giving it all of the heart and effort that you
• 13:10
  Speaker 5: did when you first started. Those two things can only
• 13:13
  Speaker 5: happen when hobby becomes obsession and that hobby becomes something
• 13:17
  Speaker 5: that you want to improve rapidly over time.
• 13:20
  Speaker 4: That's fantastic advice.
• 13:21
  Speaker 3: Uh. You know, I ask questions a lot of times
• 13:25
  Speaker 3: based on viewership and who the audience is, but also
• 13:28
  Speaker 3: like things I'm wanting to know.
• 13:30
  Speaker 4: And it was cool for me to hear you.
• 13:33
  Speaker 3: Talk about obsession versus interest, because there's a huge difference there.
• 13:38
  Speaker 4: You're right, that's a really great signal.
• 13:40
  Speaker 3: Another quote from your book that I loved was everybody
• 13:43
  Speaker 3: has and I'm going to fucking quit moment. And you know,
• 13:47
  Speaker 3: as you mentioned, Bulletin pivoted so many times, there were
• 13:50
  Speaker 3: different iterations of the business. How did you decide you
• 13:53
  Speaker 3: were going to pivot versus fucking quit?
• 13:57
  Speaker 5: I mean, there was a moment in twenty sixteen where
• 13:59
  Speaker 5: I like kind of tried to fucking quit and it
• 14:03
  Speaker 5: ended up roping me back in. And I think a
• 14:05
  Speaker 5: big part of overcoming that first pivot from the newsletter
• 14:09
  Speaker 5: and the e commerce site to launching these pop up events,
• 14:12
  Speaker 5: which were so labor intensive and stressful, and we were
• 14:15
  Speaker 5: working seven days a week. I think I was really
• 14:18
  Speaker 5: burnt out. It wasn't what I had signed up for, right,
• 14:21
  Speaker 5: Like I wanted to write and I was now running events,
• 14:24
  Speaker 5: and I was like, this isn't like I didn't leap
• 14:26
  Speaker 5: a faith into the ABYSS to be running events. I
• 14:31
  Speaker 5: leaked into faith into the ABYSS to be writing. And
• 14:34
  Speaker 5: I think the other thing is like just data and signal.
• 14:37
  Speaker 5: Like our stores worked, they just didn't scale.
• 14:40
  Speaker 1: We couldn't go.
• 14:41
  Speaker 5: From three stores to thirty stores. We didn't have the personnel,
• 14:44
  Speaker 5: we didn't have the capital. But there was this nugget
• 14:47
  Speaker 5: of brands are really struggling to get into retail stores.
• 14:51
  Speaker 5: They keep complaining about how expensive it is to do
• 14:54
  Speaker 5: trade shows and how expensive it is to do showrooms,
• 14:57
  Speaker 5: and they're gaining so much about selling with as a retailer.
• 15:01
  Speaker 5: How do we help these brands connect with more retailers
• 15:04
  Speaker 5: that aren't bulletin So I think, because we're so obsessed
• 15:07
  Speaker 5: with this customer and we know them so well, like this,
• 15:11
  Speaker 5: maybe we're delusional and there those don't work out in
• 15:13
  Speaker 5: the end, But like there always has seemed to be
• 15:16
  Speaker 5: some sort of signal pulling us in a new direction
• 15:19
  Speaker 5: that's more scalable and more optimized and more profitable and
• 15:23
  Speaker 5: more manageable.
• 15:23
  Speaker 3: I love the idea of creating something and being your
• 15:26
  Speaker 3: own customer. It's kind of why I created the podcast.
• 15:29
  Speaker 3: I was like, I want to do These are the
• 15:31
  Speaker 3: people I want to hear from, and these are the
• 15:33
  Speaker 3: questions I want to be asking. You said, no one
• 15:36
  Speaker 3: is spared the roller coaster ride of uncertainty and defeat
• 15:39
  Speaker 3: of mastery and euphoria. There's so much magic when you're
• 15:43
  Speaker 3: building something, and so much misery. And I know you
• 15:47
  Speaker 3: mentioned talking about these highs and lows. How come no
• 15:50
  Speaker 3: one talks about them? And how can we better prepare
• 15:55
  Speaker 3: ourselves and other people for them? Is it just about
• 15:57
  Speaker 3: like letting them know that that's normal.
• 16:01
  Speaker 1: That's such a good question. And I think there are.
• 16:03
  Speaker 5: A few different reasons why entrepreneurs or people that are
• 16:07
  Speaker 5: building something from nothing don't talk is openly about the
• 16:10
  Speaker 5: shitty times.
• 16:10
  Speaker 1: I think one of them is as women.
• 16:14
  Speaker 5: Objective studies show that women are held to different ethical standards,
• 16:18
  Speaker 5: and we are measured on our accomplishments versus our potential.
• 16:22
  Speaker 5: And so when you're out there and you're putting yourself
• 16:25
  Speaker 5: out there to your customers, or on Instagram, or you're
• 16:29
  Speaker 5: in business meetings or you're talking to potential influencers or partners.
• 16:34
  Speaker 5: There's this sense of I have to be fully buttoned
• 16:37
  Speaker 5: up and there can be no mess, and everything needs
• 16:40
  Speaker 5: to seem and be perfect, because no one's going to
• 16:42
  Speaker 5: want to invest in me if they know there's a
• 16:44
  Speaker 5: part of my business I haven't figured out yet. No
• 16:46
  Speaker 5: influencer is going to want to work with me if
• 16:49
  Speaker 5: they realize that I had a really bad day and
• 16:53
  Speaker 5: I mentioned that on the call. No customers are going
• 16:56
  Speaker 5: to want to shop for me if they realize that
• 16:59
  Speaker 5: there's a glos which with my fulfillment center and that's
• 17:02
  Speaker 5: the reason why all of their orders are late. Rather
• 17:05
  Speaker 5: than just owning up to it and being honest, I
• 17:07
  Speaker 5: think that a lot of women entrepreneurs in particular, feel
• 17:11
  Speaker 5: like they're somehow invalidating themselves or setting themselves up to
• 17:15
  Speaker 5: fail if they communicate about the depressive episodes or the
• 17:19
  Speaker 5: anxious moments or the hard times.
• 17:22
  Speaker 1: I think that.
• 17:24
  Speaker 5: What we really need to do is become more vocal
• 17:28
  Speaker 5: about those things because for me, and I'm curious how
• 17:32
  Speaker 5: you feel too, I entered entrepreneurship.
• 17:36
  Speaker 1: With a completely warped vision of what entrepreneurship was.
• 17:40
  Speaker 5: I had read books like Girl Boss and Lean In
• 17:44
  Speaker 5: where it seemed like it just kind of portrays a
• 17:46
  Speaker 5: very glamorized, like inaccurate version of entrepreneurship that isn't the true, lived.
• 17:52
  Speaker 1: Real experience that all of us go through every day.
• 17:55
  Speaker 3: I'm glad you mentioned imposter syndrome because I think it's
• 17:58
  Speaker 3: a really buzzy.
• 17:59
  Speaker 4: Word right now, and I loved your chapter on it.
• 18:03
  Speaker 4: You wrote an entire chapter on it.
• 18:05
  Speaker 3: Can you kind of break down what imposter syndrome really
• 18:08
  Speaker 3: is and how it personally affected you?
• 18:11
  Speaker 5: The definition of imposter syndrome is it basically labels that.
• 18:15
  Speaker 1: Nagging voice inside so many of us.
• 18:17
  Speaker 5: Most people experience imposter syndrome that says you're not good enough,
• 18:21
  Speaker 5: you don't know what you're doing, You're a fraud, and
• 18:24
  Speaker 5: someone's going to find you out. A lot of people
• 18:27
  Speaker 5: feel this when they have moments of success. So like
• 18:30
  Speaker 5: I was on the Today Show and a big voice
• 18:32
  Speaker 5: inside me was like, why the fuck do they want
• 18:34
  Speaker 5: me on the Today Show? Like what do I have
• 18:36
  Speaker 5: to say? Why does anyone want to hear from me?
• 18:39
  Speaker 5: I think a lot of people feel this way. In
• 18:41
  Speaker 5: their darkest moments too, where if they lose out on something,
• 18:45
  Speaker 5: or they get rejected by an investor, or they miss
• 18:47
  Speaker 5: out on a big partnership opportunity, they think that it's
• 18:50
  Speaker 5: because something's wrong with them or something's wrong with their business,
• 18:53
  Speaker 5: so they don't deserve it, when in reality, life is
• 18:56
  Speaker 5: just a series of random events and people like making
• 18:58
  Speaker 5: their own decisions doesn't mean that your craft or something's
• 19:01
  Speaker 5: wrong with you. I think what's so interesting about the
• 19:04
  Speaker 5: way imposter syndrome has been phrased to date is it's
• 19:08
  Speaker 5: kind of similar to like hysteria way back when, where
• 19:13
  Speaker 5: it's like, this is a problem that women have that
• 19:15
  Speaker 5: we need to solve.
• 19:16
  Speaker 3: Yes, that's bugging that's what's bugging me about it.
• 19:19
  Speaker 4: You're right, yeah, it's.
• 19:21
  Speaker 5: But that's not what it is. Imposter syndrome happens. It's
• 19:24
  Speaker 5: it's the sensation is exacerbated when people feel underrepresented in
• 19:28
  Speaker 5: their context.
• 19:29
  Speaker 4: We say that again, that's so, that is it.
• 19:32
  Speaker 5: Imposter syndrome is exacerbated when you feel underrepresented in your context.
• 19:38
  Speaker 5: So this looks like black students at a majority white
• 19:42
  Speaker 5: college feeling increased depression and anxiety and feelings of fraudulence.
• 19:47
  Speaker 5: This feels like women in STEM feeling like they don't
• 19:51
  Speaker 5: deserve to be there because they look around and they
• 19:53
  Speaker 5: don't see any other women at their level.
• 19:56
  Speaker 1: It looks like Latino women.
• 19:58
  Speaker 5: And black women in corporate America at the C suite
• 20:01
  Speaker 5: level or the director of VP level and realizing that
• 20:06
  Speaker 5: no one else looks like them at that tear, and
• 20:08
  Speaker 5: so they feel anxious.
• 20:10
  Speaker 1: They feel like they have to prove themselves.
• 20:11
  Speaker 5: They feel like they're on this constant chase to kind
• 20:15
  Speaker 5: of keep that seat. But that's the cause of imposter syntome.
• 20:18
  Speaker 5: It's not because women have something wrong with us or
• 20:21
  Speaker 5: we're born and feeling like impostors. It's it's literally because
• 20:25
  Speaker 5: we've been trained since we were young that women don't
• 20:29
  Speaker 5: take companies public. Only twenty women have taken their company's public,
• 20:33
  Speaker 5: most recently Whitney Wolf.
• 20:34
  Speaker 1: Jessica Alba's about to.
• 20:35
  Speaker 5: Be number twenty one, or it might be twenty one
• 20:37
  Speaker 5: and twenty two, but it's around there. We don't we
• 20:40
  Speaker 5: like the most famous founders we know are like Jeff Bezos,
• 20:43
  Speaker 5: Elon Musk, and like Jack Dorsey and Mark Zuckerberg. Where's
• 20:48
  Speaker 5: like Sheila Zuckerberg, you know, like, it's not that something's
• 20:52
  Speaker 5: wrong with us straight out the womb where we feel
• 20:54
  Speaker 5: like frauds and we feel like we don't deserve it,
• 20:56
  Speaker 5: and this is like we need to go to a
• 20:58
  Speaker 5: workshop to like break the spec.
• 21:00
  Speaker 1: We need to do some journaling to break the spell.
• 21:03
  Speaker 5: It's like, no, we need more women represented in all
• 21:06
  Speaker 5: these different tiers of leadership. We need more women taking
• 21:09
  Speaker 5: their companies public. We need the media to put more
• 21:12
  Speaker 5: women from the center and make them part of headline
• 21:15
  Speaker 5: business news stories so that younger women have exposure to that.
• 21:18
  Speaker 5: And then we really need to focus within that subset
• 21:21
  Speaker 5: on bipop women in particular, because that exacerbating feeling is
• 21:25
  Speaker 5: even worse for them. Yes, so that everything you're saying
• 21:29
  Speaker 5: about it, like what you said about imposter syndrome, kind
• 21:32
  Speaker 5: of becoming this buzzword that's starting to feel very icky.
• 21:35
  Speaker 5: I think it's because it's almost like self care. It's
• 21:38
  Speaker 5: like getting co opted to something that it isn't and
• 21:41
  Speaker 5: it's not women's problem. To solve imposter syndrome, like men
• 21:44
  Speaker 5: and businesses and governments need to put women in more
• 21:48
  Speaker 5: positions of power and leadership in a very visible way,
• 21:51
  Speaker 5: and then we'll actually feel represented, and we won't continue
• 21:54
  Speaker 5: to feel the sense of like, I don't belong here,
• 21:56
  Speaker 5: What am I doing here?
• 21:57
  Speaker 1: Why did someone give me this opportunity? I don't deserve it.
• 21:59
  Speaker 3: There's an element here too that I'm wondering what you
• 22:02
  Speaker 3: think about. I think there's perceived capability that men are
• 22:07
  Speaker 3: afforded when they walk into a room, and that triggers
• 22:12
  Speaker 3: imposter syndrome for women or anybody of a marginalized group.
• 22:17
  Speaker 3: So hearing you say that we need to see more
• 22:20
  Speaker 3: people doing that will inevitably change perceived capability.
• 22:26
  Speaker 4: Yes, yes, okay.
• 22:28
  Speaker 3: So imposter syndrome is sort of followed up by a
• 22:31
  Speaker 3: fake it till you make it mentality most of the time.
• 22:33
  Speaker 3: And you the chapter about this, and you give ten
• 22:36
  Speaker 3: pieces of really great advice. Three of them really stuck
• 22:39
  Speaker 3: out to me. Put it on LinkedIn, always bring a
• 22:41
  Speaker 3: business card, meet fancy people, and name drop them, which
• 22:45
  Speaker 3: I thought was very funny because most people would not
• 22:49
  Speaker 3: say put it on LinkedIn. They'd probably say, like, put
• 22:51
  Speaker 3: it on Instagram, And then a lot of people would
• 22:54
  Speaker 3: say a business card that's outdated, and then meet fancy
• 22:57
  Speaker 3: people and name drop them. It's like, no, that's ghosh.
• 23:00
  Speaker 3: You made great cases for all of these. Can you
• 23:03
  Speaker 3: dive into a little bit.
• 23:05
  Speaker 1: Yeah.
• 23:05
  Speaker 5: So with the LinkedIn one, that's where people go to
• 23:10
  Speaker 5: check out your professional history. So like I have LinkedIn Premium,
• 23:13
  Speaker 5: I can see who's stalking me. It's a little bit expensive,
• 23:16
  Speaker 5: but it's totally worth it. And when I meet investors,
• 23:20
  Speaker 5: they go to my LinkedIn. When I talk to potential partners,
• 23:23
  Speaker 5: they go.
• 23:23
  Speaker 1: To my LinkedIn.
• 23:25
  Speaker 5: LinkedIn I think is kind of this like dirty networking
• 23:28
  Speaker 5: place that people don't want to pay attention to anymore.
• 23:31
  Speaker 1: It's kind of like how.
• 23:32
  Speaker 5: Millennials and above, well millennials in below feel about Facebook,
• 23:36
  Speaker 5: where it's like, oh my god, the notifications, the.
• 23:38
  Speaker 1: Content, it's too much.
• 23:40
  Speaker 5: But if you would put your new job on LinkedIn,
• 23:43
  Speaker 5: if you got promoted, and you would put your promotion
• 23:46
  Speaker 5: on LinkedIn, if you changed companies and you would put
• 23:49
  Speaker 5: that on LinkedIn, if you're working on a side hustle,
• 23:52
  Speaker 5: you should definitely put it on LinkedIn. People are looking
• 23:56
  Speaker 5: for you, they might be looking up keywords, they might
• 23:58
  Speaker 5: be vetting you and looking at your LinkedIn.
• 24:00
  Speaker 1: And if you're in conversation with a potential.
• 24:02
  Speaker 5: Partner about sponsoring an event that you're doing for your
• 24:05
  Speaker 5: side hustle, and they go to your LinkedIn and your
• 24:08
  Speaker 5: side hustle or that business isn't listed, They're going to
• 24:11
  Speaker 5: question how seriously you're taking it. I think a lot
• 24:13
  Speaker 5: of these, like the suggestions in the book are like
• 24:16
  Speaker 5: centered around the fact that people will only take what
• 24:19
  Speaker 5: you're doing as seriously as you take it yourself. So
• 24:21
  Speaker 5: that's a big part of it, is like if you're
• 24:24
  Speaker 5: taking this thing seriously and you're putting it on LinkedIn,
• 24:26
  Speaker 5: then you're training someone else to take it seriously as well.
• 24:30
  Speaker 5: The second one of a business card, I think this
• 24:33
  Speaker 5: is very similar. I think that I write this in
• 24:36
  Speaker 5: the book, someone's probably going to throw it away. I'm
• 24:38
  Speaker 5: not acting like someone's going to take your business card
• 24:40
  Speaker 5: and be like, oh, let me put this in my
• 24:42
  Speaker 5: outBut of business cards. But I remember when we made
• 24:46
  Speaker 5: business cards for Bulletin. We Alta and I had to
• 24:49
  Speaker 5: go to south By Southwest for work for our full
• 24:52
  Speaker 5: time jobs, and we just like didn't work on that
• 24:55
  Speaker 5: at all and just ran around south By self must
• 24:57
  Speaker 5: giving out our business cards. And that was such a
• 25:00
  Speaker 5: a transformative moment in me taking the business seriously. Like,
• 25:04
  Speaker 5: if you're going to be meeting people at events or
• 25:06
  Speaker 5: out in the world, and you never know who you
• 25:09
  Speaker 5: can meet.
• 25:09
  Speaker 1: Like, really, I've met so many people.
• 25:11
  Speaker 5: In passing have that business card because again, it's training
• 25:14
  Speaker 5: them to take you seriously. And the off chance that
• 25:17
  Speaker 5: you bump into someone at a club, at a bar,
• 25:19
  Speaker 5: at a restaurant on the street who could have something
• 25:22
  Speaker 5: to offer you or a connection that they can broker
• 25:25
  Speaker 5: for you, give them that business card because it also
• 25:28
  Speaker 5: gives them like an esthetic sense of your brand and
• 25:31
  Speaker 5: what you're about.
• 25:32
  Speaker 1: It's a moment to take something from.
• 25:34
  Speaker 5: A conversation where there's no visuals to like, oh, the
• 25:37
  Speaker 5: weight of this card and the design and the branding
• 25:40
  Speaker 5: and the font, like it kind of helps give someone
• 25:43
  Speaker 5: more color about you and what you're about.
• 25:45
  Speaker 1: And I would say the last one, which I.
• 25:47
  Speaker 5: Know is totally ghosh, And I was thinking of not
• 25:49
  Speaker 5: putting it in of meeting with fancy people and name
• 25:51
  Speaker 5: dropping them, they don't need to be like the most
• 25:55
  Speaker 5: most fancy people. But I think so often people don't
• 25:59
  Speaker 5: realize is that, like because of social media, our whole
• 26:02
  Speaker 5: world is governed by social proof. Like when Glossier launched
• 26:06
  Speaker 5: and they decided to work with real women and like
• 26:10
  Speaker 5: influencers instead of models.
• 26:13
  Speaker 1: That moment of social proof on social media.
• 26:15
  Speaker 5: Them doing that strategy completely changed the landscape for brands
• 26:19
  Speaker 5: and how they market, and so much of it is
• 26:21
  Speaker 5: about social proof and showing who else likes this, who
• 26:24
  Speaker 5: else believes in this, And the same thing goes for
• 26:27
  Speaker 5: you as a person and as a business owner. If
• 26:29
  Speaker 5: you've partnered with a cool company, even if it was
• 26:32
  Speaker 5: a year ago and you're dusting your old side hustle
• 26:36
  Speaker 5: off and trying to pick it back up again, mention
• 26:38
  Speaker 5: to that potential new partner that you partnered with that
• 26:40
  Speaker 5: person a year ago. There's no shame in the fact
• 26:42
  Speaker 5: that it was a year ago. Even if you're a
• 26:44
  Speaker 5: small business and you maybe haven't broken connections with like
• 26:48
  Speaker 5: famous influencers or like anyone that anyone would know by name,
• 26:52
  Speaker 5: you as a small business being able to come to
• 26:54
  Speaker 5: a potential partner or sponsor or employee and say, yeah,
• 26:58
  Speaker 5: I've done work with these five other small businesses. Here's
• 27:00
  Speaker 5: what we did together. It gives signal to people that
• 27:03
  Speaker 5: you know what you're doing, people like working with you,
• 27:06
  Speaker 5: and you're already kind of in the throes of making
• 27:08
  Speaker 5: this thing happen.
• 27:09
  Speaker 1: So someone's just coming along for the ride.
• 27:11
  Speaker 5: But I think that point about like meet fancy people
• 27:15
  Speaker 5: and name drop them, don't overextend it. Don't say that
• 27:18
  Speaker 5: you're like friends with Donna Tulla Versauci if you like
• 27:21
  Speaker 5: brushed shoulders with her in an elevator, but you know.
• 27:25
  Speaker 3: Like no, but it's perceived credibility.
• 27:28
  Speaker 5: Be comfortable speaking to your your supporters and your circle
• 27:31
  Speaker 5: and people that have supported you and given you that
• 27:32
  Speaker 5: validation in the past, because it's going to open someone
• 27:36
  Speaker 5: up to feeling comfortable to partner with you or validate
• 27:39
  Speaker 5: you as well.
• 27:39
  Speaker 3: I think about it in terms of like when you
• 27:41
  Speaker 3: just meet a person in the world and you have
• 27:43
  Speaker 3: a mutual friend, you feel immediately closer than just a
• 27:46
  Speaker 3: random connection. And that's how I perceived what you were saying,
• 27:48
  Speaker 3: which I think is great advice.
• 27:52
  Speaker 4: There's a quote that I really really.
• 27:54
  Speaker 3: Loved because I want to get into money. You say,
• 27:56
  Speaker 3: let's talk about taking money and making money, and I
• 28:00
  Speaker 3: don't know a ton about money, so it's hard for
• 28:02
  Speaker 3: me to talk about it, and you really broke it down,
• 28:04
  Speaker 3: which I think so many people are looking for that information.
• 28:09
  Speaker 3: You said often when you're in scrap mode and being
• 28:11
  Speaker 3: super budget conscious it can be hard to assign an
• 28:13
  Speaker 3: internalize value to things that don't directly impact your bottom line.
• 28:17
  Speaker 4: What did you mean by that?
• 28:18
  Speaker 5: There are certain things in life where you put money
• 28:22
  Speaker 5: in and you get money out very directly. Whether that's
• 28:25
  Speaker 5: you doing let's say, paid Instagram ads to promote this podcast,
• 28:31
  Speaker 5: You're going to lose money for a little bit. But
• 28:33
  Speaker 5: once you find the sweet spot of your copy and
• 28:36
  Speaker 5: your esthetic and the design and the messaging and the
• 28:40
  Speaker 5: call to action, by month three or four, depending on
• 28:43
  Speaker 5: how much you're spending, you'll be able to do a
• 28:45
  Speaker 5: math problem of like, put ten thousand dollars into this
• 28:49
  Speaker 5: and get forty thousand dollars out. That's kind of the
• 28:53
  Speaker 5: nature of like direct investments that build more incremental value
• 28:58
  Speaker 5: and more money.
• 29:00
  Speaker 1: There are other investments that you have to make as
• 29:02
  Speaker 1: a business.
• 29:03
  Speaker 5: Owner where you're spending money and you're not projecting an
• 29:07
  Speaker 5: immediate return on that investment. So an example that I
• 29:11
  Speaker 5: gave in the book is we worked out of the
• 29:14
  Speaker 5: most like rogue crazy places in New York for the
• 29:18
  Speaker 5: first few years building Bulletin. Like we'd work out of
• 29:21
  Speaker 5: a cafe and pay our interns in sandwiches and coffee
• 29:24
  Speaker 5: and get kicked out like every single time because we
• 29:27
  Speaker 5: overseae our welcome. We worked in a coworking space. We
• 29:31
  Speaker 5: like basically shared an office with the Magnesis and Fire
• 29:34
  Speaker 5: Festival team. Like, we had a crazy series of co
• 29:40
  Speaker 5: working spaces and coffee shops, and eventually we were like,
• 29:44
  Speaker 5: we need our own space, and so we ended up
• 29:47
  Speaker 5: deciding to take the apartment in the back of our
• 29:50
  Speaker 5: Nolita retail store. It was super small and cramped. The
• 29:54
  Speaker 5: ceilings were like much lower than a normal ceiling, and
• 29:58
  Speaker 5: the entire office smelled like Pepperona all the time because
• 30:01
  Speaker 5: Prince Street Pizza was right next door to our store,
• 30:04
  Speaker 5: and like the meat smells, the cured meat smells would
• 30:07
  Speaker 5: just like waft into the apartment. We had an ant infestation.
• 30:10
  Speaker 5: But it was super cheap. I feel like that office
• 30:13
  Speaker 5: was like two thousand dollars a month or something, and
• 30:16
  Speaker 5: we went from like four to five to six to
• 30:19
  Speaker 5: eventually eight women working out of that office, and it
• 30:23
  Speaker 5: was really hard for me and Alana to like accept
• 30:26
  Speaker 5: that our employees were kind of miserable and invest in
• 30:30
  Speaker 5: a more expensive office because you can't quantify how much
• 30:34
  Speaker 5: harder your employees will work.
• 30:36
  Speaker 1: If you get a new office.
• 30:37
  Speaker 5: You can't quantify how much more revenue that will drive
• 30:39
  Speaker 5: in our store, which.
• 30:40
  Speaker 1: Has nothing to do with the office.
• 30:43
  Speaker 5: It won't tell us how much more money we'd make
• 30:46
  Speaker 5: on e commerce. But it was an investment that we
• 30:49
  Speaker 5: had to make in our employees to show them we
• 30:52
  Speaker 5: care about your well being. We care about you liking
• 30:54
  Speaker 5: where you're working, we care about you having space, we
• 30:57
  Speaker 5: care about you not smelling like you know, meaty pepper
• 31:00
  Speaker 5: every single day.
• 31:01
  Speaker 1: And I remember investing in that new office.
• 31:03
  Speaker 5: It was way more expensive than the back office in Nolida,
• 31:07
  Speaker 5: and it was like I could have thrown up for weeks,
• 31:09
  Speaker 5: Like I was just like, oh my god, we're like
• 31:11
  Speaker 5: spending so much money in this office. But you have
• 31:14
  Speaker 5: to make that investment as a business owner and know
• 31:17
  Speaker 5: and accept that you're optimizing for something else. You're not
• 31:21
  Speaker 5: always going to be able to optimize for money in,
• 31:23
  Speaker 5: money out, and if it's in your budget to like
• 31:25
  Speaker 5: elevate or glow up, as I say in the book,
• 31:28
  Speaker 5: aspects of your business that might have more long term
• 31:31
  Speaker 5: gains or long term value, like employee satisfaction, like not
• 31:34
  Speaker 5: getting horrible glastdoor reviews, like employee retention, and like those
• 31:40
  Speaker 5: things are quantifiable. If we had any of our employees
• 31:43
  Speaker 5: leave because of the Pepperoni office, it would have cost
• 31:45
  Speaker 5: money to hire recruiters, money to train those new people,
• 31:48
  Speaker 5: and it would have cost us time. So that's kind
• 31:50
  Speaker 5: of what I mean about that, is like there are
• 31:52
  Speaker 5: so many instances as an entrepreneur where you can like
• 31:55
  Speaker 5: put money in be boop op, do some math, and
• 31:57
  Speaker 5: you know how much you're making after. But most of
• 31:59
  Speaker 5: the time time er making investments in things that don't
• 32:02
  Speaker 5: have immediate payoff, immediate monetary payoff.
• 32:05
  Speaker 3: And sometimes it's you're just walking with faith because you
• 32:10
  Speaker 3: don't know if that ever will be a payoff, but
• 32:12
  Speaker 3: you kind of have to just trust your instinct on
• 32:14
  Speaker 3: that one.
• 32:14
  Speaker 4: It seems so.
• 32:16
  Speaker 3: In twenty nineteen, two point eight percent of funding went
• 32:19
  Speaker 3: to women led startups. In twenty twenty, that number actually
• 32:22
  Speaker 3: fell to two point three Yep, Can you give us
• 32:25
  Speaker 3: a glimpse into what it's like as a woman to
• 32:28
  Speaker 3: try and raise capital, because it seems like a horrendous
• 32:31
  Speaker 3: process for anybody, let alone someone who's part of that
• 32:34
  Speaker 3: two point eight percent.
• 32:36
  Speaker 5: When you're a woman founder in Silicon Valley in the
• 32:40
  Speaker 5: venture capital space.
• 32:42
  Speaker 1: You know all the data, like you know.
• 32:45
  Speaker 5: Going into a conversation with an investor that you that
• 32:49
  Speaker 5: if you get this check, you're.
• 32:50
  Speaker 1: In the two percent of something.
• 32:52
  Speaker 5: You know that Harvard Business Review did a study around
• 32:56
  Speaker 5: venture capitalists and how they interview male founders versus how
• 33:00
  Speaker 5: they interview women founders. When they interview male founders, they
• 33:04
  Speaker 5: ask how big is this opportunity? What about your team
• 33:08
  Speaker 5: is going to help you win? Why is this a
• 33:10
  Speaker 5: billion dollar business? How are you going to get to
• 33:12
  Speaker 5: be a billion dollar business? When venture capitalists interview women
• 33:16
  Speaker 5: or listen to a women pitch, they ask, why aren't
• 33:20
  Speaker 5: you going to fail? Why do you have what it
• 33:22
  Speaker 5: takes to make this a billion dollar business? There's so
• 33:25
  Speaker 5: much more skepticism laced into every single question.
• 33:28
  Speaker 1: And I highly recommend that anyone listening.
• 33:30
  Speaker 5: To this googles the Harvard Business Review study because they
• 33:33
  Speaker 5: literally followed different like founders and tracked this different language.
• 33:40
  Speaker 5: Yea fascating as a female founder, you like know these
• 33:43
  Speaker 5: things Because Silicon Valley is historically a boys club, ninety
• 33:49
  Speaker 5: percent of venture capital goes to white men, So I
• 33:52
  Speaker 5: think that means at the outset, you're always a bit
• 33:55
  Speaker 5: sensitive and prickly. You always are kind of looking out
• 33:58
  Speaker 5: for these signals that someone is demeaning you or undercutting you,
• 34:02
  Speaker 5: or framing a question with skepticism or more skepticism than
• 34:06
  Speaker 5: they might demand. Other studies have shown that women have
• 34:09
  Speaker 5: to present more data in order to get that check.
• 34:12
  Speaker 1: Men win and get checks because of their potential.
• 34:15
  Speaker 5: Women get checks because of their traction, their revenue and
• 34:19
  Speaker 5: the data that they're able to share.
• 34:20
  Speaker 3: Perceived capability, yeah, perceive competence.
• 34:23
  Speaker 1: Yeah.
• 34:24
  Speaker 5: So as a woman, it's like you already go into
• 34:26
  Speaker 5: the meeting being like, Okay, I have to have like
• 34:28
  Speaker 5: my folder, my mental folder of like every single number,
• 34:31
  Speaker 5: every single metric. You're like literally training like Rocky style,
• 34:35
  Speaker 5: like grilling your co founder on all the numbers. You
• 34:39
  Speaker 5: know that the chances of you getting the check are
• 34:42
  Speaker 5: super low, Like you kind of I this is like
• 34:45
  Speaker 5: a fun fact about me. But before my senior year
• 34:48
  Speaker 5: of college, I did the Voice and there was only
• 34:51
  Speaker 5: one spot left on the whole show and I knew it,
• 34:53
  Speaker 5: and I went up to singing for Christina Aguilera and
• 34:56
  Speaker 5: she was the only one with a spot. And it's
• 34:58
  Speaker 5: like that feeling of doing that perform of being like, well,
• 35:01
  Speaker 5: the chances of this happening to me are like very slim.
• 35:04
  Speaker 4: Uh wait, now I need you to sing for us.
• 35:08
  Speaker 1: I'll sing at the end.
• 35:09
  Speaker 5: Really, oh my god, I'm the same feeling of like
• 35:12
  Speaker 5: you're defeated from the very jump okay. And so as
• 35:16
  Speaker 5: a woman, you no one tells you how to be
• 35:20
  Speaker 5: with investors, but you kind of know that you're not
• 35:23
  Speaker 5: supposed to be hyper feminine. So when Alana and I
• 35:26
  Speaker 5: would go pitch, we would wear like Elizabeth Holmes style
• 35:29
  Speaker 5: black turtlenecks, we would barely wear any makeup. We'd pull
• 35:33
  Speaker 5: our hair back in buns. There's kind of this like
• 35:35
  Speaker 5: subtle effort and like internalized misogyny, where you, as a
• 35:39
  Speaker 5: woman are like I have to remove my femininity from
• 35:42
  Speaker 5: the equation. I have to get them to see me
• 35:45
  Speaker 5: as like a founder and business person and like ignore
• 35:48
  Speaker 5: the fact that I'm a woman. I've heard so many
• 35:50
  Speaker 5: stories of women getting hit on. I have a founder
• 35:55
  Speaker 5: who's very close to me, who was connected with an
• 35:58
  Speaker 5: investor over LinkedIn and and they basically got like.
• 36:02
  Speaker 1: Sexually harassed at this first meeting.
• 36:04
  Speaker 5: All of the misogyny that exists in the world and
• 36:06
  Speaker 5: the way that women are held to different standards. VC
• 36:09
  Speaker 5: is just a microcosm of that. And I think because
• 36:12
  Speaker 5: these investors have so much power, and the power dynamic.
• 36:16
  Speaker 1: Is so imbalanced.
• 36:18
  Speaker 5: Being a woman in venture capital, you just you feel
• 36:22
  Speaker 5: like the cards are so stacked against you, and the
• 36:24
  Speaker 5: expectations are so much higher and what you have to
• 36:26
  Speaker 5: deliver on is so much higher that it's a very demeaning.
• 36:31
  Speaker 1: Process from start to finish. This is much harder.
• 36:34
  Speaker 5: Let me just add for women of color, Latina founders
• 36:38
  Speaker 5: got less than one percent of venture financing. Black female
• 36:41
  Speaker 5: founders got less than one percent of venture financing. So
• 36:45
  Speaker 5: for me, I'm at least able to sit across from
• 36:47
  Speaker 5: an investor at a firm who's a white guy, who's like, oh,
• 36:51
  Speaker 5: we like yeah, because we're both white, I feel that
• 36:54
  Speaker 5: level of familiarity and comfort. Whereas women of color come
• 36:59
  Speaker 5: into those rooms and that feeling of being distant from
• 37:03
  Speaker 5: the person across the table, being unrelatable, being unfamiliar is
• 37:07
  Speaker 5: just so much more exacerbated, and that makes their pitch
• 37:10
  Speaker 5: process all that much harder and defeating.
• 37:13
  Speaker 3: Thank you for giving us a lens into that. I've
• 37:16
  Speaker 3: never talked to anybody who's pitched like a woman. I've
• 37:19
  Speaker 3: talked to men, I think male founders who have done it,
• 37:21
  Speaker 3: so it was cool to hear your perspective. So when
• 37:23
  Speaker 3: I started this podcast, I really wish that people would
• 37:27
  Speaker 3: have told me to bank some episodes.
• 37:30
  Speaker 4: There's a lot of things I wish people would have
• 37:31
  Speaker 4: told me.
• 37:32
  Speaker 3: I tried to do research, but like, it's difficult to
• 37:34
  Speaker 3: give someone advice.
• 37:35
  Speaker 1: I think, what does it mean to bank an episode?
• 37:39
  Speaker 3: Like to pre record a few episodes so that you're
• 37:41
  Speaker 3: not scrambling.
• 37:42
  Speaker 4: Like the week of every week?
• 37:44
  Speaker 3: Oh god, God, you know, if you have some like
• 37:46
  Speaker 3: and you have some leeway or a runway. I'm sure
• 37:49
  Speaker 3: there are a lot of things that you could give us,
• 37:52
  Speaker 3: But I'm wondering if one sticks out in your mind
• 37:54
  Speaker 3: as something you really wish people would have told you
• 37:57
  Speaker 3: before you started a company.
• 37:59
  Speaker 5: I wish someone had told me that you're not going
• 38:01
  Speaker 5: to do what you like to do when you start
• 38:04
  Speaker 5: a business. If you grow and it goes well, you
• 38:07
  Speaker 5: end up delegating so much of the things that inspired
• 38:11
  Speaker 5: you or motivated you to start the business in the
• 38:13
  Speaker 5: first place. A lot of people, if they just run
• 38:16
  Speaker 5: a small business and they want to keep it small
• 38:18
  Speaker 5: and quaint, there's no shame in that. My book, How
• 38:21
  Speaker 5: to Build a Goddamn Empire, the title is kind of
• 38:22
  Speaker 5: deliberately cheeky because I truly believe your empire should be
• 38:25
  Speaker 5: as big or as small as you want it to be.
• 38:27
  Speaker 1: But if you're doing.
• 38:28
  Speaker 5: Something small, like maybe you keep doing a lot of
• 38:30
  Speaker 5: what you're doing, but if you're growing, you will no
• 38:33
  Speaker 5: longer be doing the hobby or the obsession that brought
• 38:37
  Speaker 5: you to start that business in the first place.
• 38:40
  Speaker 3: How would you define girl boss culture before we get
• 38:42
  Speaker 3: into it?
• 38:43
  Speaker 5: Okay, I'm going to spin a web and hope it's okay.
• 38:47
  Speaker 5: And you and I talked about this when we first chatted, Like,
• 38:50
  Speaker 5: I think there are varying definitions. I don't know that
• 38:52
  Speaker 5: anyone has like put it in Miriam Webster.
• 38:54
  Speaker 1: Yeah.
• 38:55
  Speaker 5: I think girl boss culture is a few things. I
• 38:59
  Speaker 5: think there are a few pills to it. I think
• 39:01
  Speaker 5: one of it is everything's going to be great because
• 39:04
  Speaker 5: you're great, you're a girl boss.
• 39:06
  Speaker 1: It's kind of that toxic positivity that's like.
• 39:09
  Speaker 5: Just because you exist and you're pursuing your dreams, everything
• 39:16
  Speaker 5: is going to manifest itself right in front of you.
• 39:19
  Speaker 5: I think the second layer of it is a lack
• 39:23
  Speaker 5: of giving credit where credit is due to other people.
• 39:25
  Speaker 5: I think it's a very not self centered, but very
• 39:29
  Speaker 5: kind of like indulgent, indulgent perspective where you think about
• 39:35
  Speaker 5: so many incredible businesses that launched and launched their way
• 39:39
  Speaker 5: into the spotlight and scaled that were started by women,
• 39:43
  Speaker 5: as I said, over the past few years, and I'm like,
• 39:47
  Speaker 5: I want to hear about their head of growth. I
• 39:50
  Speaker 5: want to learn about like the president that they've been
• 39:52
  Speaker 5: working with from the very beginning, Like I want them
• 39:55
  Speaker 5: to show us who's running their customer service. And I
• 39:58
  Speaker 5: feel like the kind of cult to personality around the
• 40:02
  Speaker 5: founder and them being the genius and the mastermind that
• 40:05
  Speaker 5: unlocked all of this opportunity. Let's give credit to those
• 40:08
  Speaker 5: founders because they clearly are masterful and they're very smart,
• 40:11
  Speaker 5: and they worked very hard. But it takes a village
• 40:14
  Speaker 5: to build something. It's not just one girl boss in
• 40:16
  Speaker 5: her bedroom, right. It takes a lot of people and
• 40:18
  Speaker 5: getting buy in and support from a lot of people
• 40:21
  Speaker 5: to make something successful.
• 40:23
  Speaker 1: I would say the third.
• 40:24
  Speaker 5: One is definitely like more aesthetic, like it is the
• 40:29
  Speaker 5: millennial pink, which my book is. It's kind of very femme.
• 40:34
  Speaker 5: It's very frilly, and it kind of interplays with words
• 40:38
  Speaker 5: like girl boss, sheeo, female founder in a way that
• 40:43
  Speaker 5: to me feels a bit infantilizing, Like why do we
• 40:47
  Speaker 5: need a list of one hundred most like inspiring women.
• 40:50
  Speaker 5: There is no list of one hundred most inspiring men.
• 40:53
  Speaker 5: Why are we using the word sheeo? It makes it
• 40:56
  Speaker 5: feel like the word ceo is only reserved for men.
• 40:59
  Speaker 5: So there's this kind of like playful infantilizing like aesthetic
• 41:03
  Speaker 5: and vocabulary that gets mushed together and use to kind
• 41:08
  Speaker 5: of push this this girl Boss narrative.
• 41:10
  Speaker 3: You know, when we were on the phone, you made
• 41:12
  Speaker 3: me realize that not all of girl boss culture is bad.
• 41:17
  Speaker 3: I think I was overlooking the fact that it's an evolution.
• 41:22
  Speaker 3: And so we had the Audrey Gellman of the Wing,
• 41:26
  Speaker 3: and Emily Weiss right from Glossier, and the woman who
• 41:30
  Speaker 3: started Away and all these founders that were on the
• 41:33
  Speaker 3: covers of magazines, and it was the first time we
• 41:36
  Speaker 3: were ever seeing women in charge brand it that way, right,
• 41:40
  Speaker 3: And so we're now allowed to kind of benefit from
• 41:45
  Speaker 3: the next version of whatever that is becoming because because
• 41:50
  Speaker 3: they were them exactly so exactly exact point way would you.
• 41:54
  Speaker 4: Helped me realize?
• 41:55
  Speaker 3: Because I was like, I feel like all of these
• 41:58
  Speaker 3: people built company were really self indulgent with how they
• 42:04
  Speaker 3: built them and the press around them, and then didn't
• 42:08
  Speaker 3: really live out their values in a lot of ways.
• 42:11
  Speaker 3: And I also realized I was being hypocritical because we
• 42:14
  Speaker 3: don't say that about men, like women don't have to
• 42:17
  Speaker 3: be pristine just because they're female founders. Yep, So you
• 42:20
  Speaker 3: really helped me unlock a lot of things. Do you
• 42:23
  Speaker 3: feel like girl boss culture set you up for failure
• 42:26
  Speaker 3: or success?
• 42:27
  Speaker 4: More so?
• 42:28
  Speaker 1: I truly? I mean I think it set me up
• 42:30
  Speaker 1: for success.
• 42:30
  Speaker 5: Like when I sent Sophia Amaruso, who coined the term
• 42:34
  Speaker 5: girl boss it was the title of her book and
• 42:36
  Speaker 5: her show, a copy of my book, I thanked her
• 42:39
  Speaker 5: because even though I felt alienated in many ways by
• 42:45
  Speaker 5: the version of entrepreneurship that those businesses and the press also,
• 42:49
  Speaker 5: like I think journalists have a lot of they shouldn't
• 42:52
  Speaker 5: be accountable here too. Fully, even though I felt alienated
• 42:55
  Speaker 5: by that version of entrepreneurship, when I read girl Boss
• 42:58
  Speaker 5: in twenty fourteen, it was like part of my founder journey,
• 43:01
  Speaker 5: Like I feel a certain way about it now, but
• 43:04
  Speaker 5: at the time I did find it on the whole
• 43:08
  Speaker 5: inspiring and it was really cool to hear from this
• 43:10
  Speaker 5: business owner about her journey taking something bootstrapped from zero
• 43:15
  Speaker 5: to twenty eight million dollars. Ultimately, what these founders did
• 43:19
  Speaker 5: was very difficult. I mean, for these women to have
• 43:22
  Speaker 5: raised the capital that they raised in this competitive venture
• 43:26
  Speaker 5: capital environment that doesn't favor them to grow their companies
• 43:31
  Speaker 5: to the hundreds of millions of revenue. I almost feel
• 43:34
  Speaker 5: like I can't really shit on those people. I haven't
• 43:37
  Speaker 5: done hundreds of millions of dollars of revenue yet. And
• 43:41
  Speaker 5: I think at the end of the day, in many cases,
• 43:44
  Speaker 5: those women built those kind of like indulgent brands around
• 43:48
  Speaker 5: themselves because that's what that's what they were told.
• 43:51
  Speaker 1: To do, or that was a playbook that would seem
• 43:53
  Speaker 1: like it worked.
• 43:54
  Speaker 5: Like think about women when they get interviewed on the
• 43:58
  Speaker 5: red carpet versus men. Women are asked like who are
• 44:01
  Speaker 5: you wearing? Like what's your makeup, what's your hair, what's
• 44:03
  Speaker 5: your dress? And I think that these women exploited the
• 44:07
  Speaker 5: system and kind of leaned on becoming influencers and you know,
• 44:12
  Speaker 5: pushing certain products and brands and a certain aesthetic and
• 44:15
  Speaker 5: a certain taste, because it would expand their following, and
• 44:19
  Speaker 5: expanding their following would expand their customer base. Like that
• 44:22
  Speaker 5: was the formula for so many years, and so many
• 44:25
  Speaker 5: founders are still doing that.
• 44:26
  Speaker 3: But it comes full circle to what you said earlier,
• 44:28
  Speaker 3: which was that women aren't really afforded the opportunity to
• 44:32
  Speaker 3: ask questions to look like they don't have it all together,
• 44:35
  Speaker 3: and so in a lot of ways, Audrey Gellman and
• 44:38
  Speaker 3: Sofia Moroso had to look like they had it all
• 44:41
  Speaker 3: together to think it to they made it, to get
• 44:44
  Speaker 3: in those rooms and so on and so forth. So
• 44:46
  Speaker 3: I agree with you, I just I'm more excited for
• 44:50
  Speaker 3: the next phase. Okay, So I do a few rapid
• 44:54
  Speaker 3: fire questions.
• 44:55
  Speaker 1: Okay, you wrote.
• 44:57
  Speaker 3: This book over the course of three years, which I
• 44:59
  Speaker 3: thought was very interesting.
• 45:01
  Speaker 4: What did this book teach you about yourself?
• 45:04
  Speaker 5: That I can do impossible things? I remember getting this
• 45:07
  Speaker 5: book deal. My mom was in New York. She lives
• 45:10
  Speaker 5: in LA so we're never together, and I got the
• 45:12
  Speaker 5: call from my agent and I just started hysterically crying
• 45:16
  Speaker 5: outside with her holding my hand, and we were so excited.
• 45:19
  Speaker 5: But then I was like how the book Am I
• 45:21
  Speaker 5: going to do this while building a business at the
• 45:23
  Speaker 5: same time? And I wrote super early morning, super late nights.
• 45:27
  Speaker 5: Basically gave up like every weekend, big chunks of my
• 45:30
  Speaker 5: weekend for two and a half years. And anytime you
• 45:34
  Speaker 5: go into something difficult, it feels like you're climbing Mount Everest,
• 45:37
  Speaker 5: and you're like, when is this book going to be done?
• 45:39
  Speaker 1: Like I have so much more to do, But yeah, it.
• 45:41
  Speaker 5: Taught me that I can do impossible things and I
• 45:43
  Speaker 5: shouldn't be afraid of impossible things.
• 45:47
  Speaker 3: You interview thirty other female founders in the book. What
• 45:50
  Speaker 3: was the most mind shifting interview for you?
• 45:53
  Speaker 5: Okay, I'm going to bring up Jasmine Man's again because
• 45:56
  Speaker 5: this was genuinely the most mind shifting interview. Another one
• 46:00
  Speaker 5: of her quotes in the book is sometimes you don't
• 46:02
  Speaker 5: think that you have the tools and that you can't
• 46:05
  Speaker 5: be the master of your own business, of your own future.
• 46:09
  Speaker 1: But you have the tools and you're the master.
• 46:12
  Speaker 5: I think that especially for people that deal with imposter
• 46:14
  Speaker 5: syndrome or I know you ask like two people for
• 46:18
  Speaker 5: advice before you make decisions, but I think so many
• 46:20
  Speaker 5: people ask twelve people and they feel like so much
• 46:23
  Speaker 5: indecision with every big choice they make. I think like
• 46:26
  Speaker 5: really realizing that you have the lived experience.
• 46:29
  Speaker 1: And the toolkit and the.
• 46:33
  Speaker 5: Potential at your disposal to like do something crazy and
• 46:36
  Speaker 5: do what you want.
• 46:37
  Speaker 1: I think that's that was a big kind of pivotal
• 46:39
  Speaker 1: moment for me.
• 46:41
  Speaker 4: Definitely.
• 46:41
  Speaker 3: Okay, how about a book that changed your life, something
• 46:44
  Speaker 3: you think everybody should read.
• 46:46
  Speaker 5: I'm going to plug Self Care by Lee Stein, genuinely
• 46:50
  Speaker 5: because the way that it criticizes Grolbost culture, self care,
• 46:56
  Speaker 5: like all of these things that I think so many
• 46:58
  Speaker 5: of us are putting a critical ed over after the
• 47:01
  Speaker 5: pandemic and post twenty twenty. She's just so masterful, and
• 47:05
  Speaker 5: I aspire to write fiction as incisively and as as
• 47:10
  Speaker 5: much detail as she does.
• 47:12
  Speaker 4: So love that great.
• 47:13
  Speaker 1: I will recommend it always.
• 47:15
  Speaker 4: I'm with you on that.
• 47:16
  Speaker 3: I always say comedians are able to pinpoint things in
• 47:20
  Speaker 3: culture that we all experience and just they see them
• 47:22
  Speaker 3: in a different way.
• 47:23
  Speaker 4: And she did that for me in her book.
• 47:26
  Speaker 3: She put words to things that I felt but couldn't articulate.
• 47:31
  Speaker 1: It's a genius piece of writing.
• 47:33
  Speaker 4: It really is.
• 47:34
  Speaker 3: Okay, now we have the PSQ, I'm going to pick
• 47:36
  Speaker 3: a question at random. Okay, okay, oh, this is such
• 47:40
  Speaker 3: a good one. Okay, tell me something about yourself that
• 47:43
  Speaker 3: sounds made up but is one hundred percent true.
• 47:46
  Speaker 5: I feel like I already told you that I did
• 47:48
  Speaker 5: the voice, so that that's like definitely.
• 47:51
  Speaker 3: But I think that's the answer. I feel like now
• 47:53
  Speaker 3: is the time that you can see.
• 47:56
  Speaker 5: Okay, al ready if I'm not putting on do some
• 47:59
  Speaker 5: ad or adele cover.
• 48:01
  Speaker 3: Oh my god, that's like taking on Whitney.
• 48:03
  Speaker 4: Hell yeah, I'm so embarrassed.
• 48:05
  Speaker 1: Okay, let's do this, Nick, I'm singing on a podcast. Okay,
• 48:10
  Speaker 1: when the race blowing your food and the whole.
• 48:20
  Speaker 6: Okay, I'll put off you race, make you feel mine.
• 48:32
  Speaker 3: Oh my god, I can't believe that someone was born
• 48:36
  Speaker 3: with that brain and that talent.
• 48:38
  Speaker 4: Leave something for the rest of us.
• 48:40
  Speaker 1: Okay, I don't sing it. I don't sing anymore.
• 48:43
  Speaker 5: But okay, here's here's my fun fat Oh my. I
• 48:45
  Speaker 5: actually came out with a four song EP in twenty
• 48:49
  Speaker 5: eighteen titled with the Weight of Heartbreak, and I think
• 48:54
  Speaker 5: it's very good.
• 48:55
  Speaker 1: I think it's very good.
• 48:56
  Speaker 5: I wrote it and produced it with this guy named
• 48:58
  Speaker 5: Ryan who left newr But the band is called Ladylike.
• 49:02
  Speaker 5: The album is with the Weight of Heartbreak, and I
• 49:05
  Speaker 5: wrote every single.
• 49:06
  Speaker 3: Song and can we find it on iTunes or Spotify?
• 49:09
  Speaker 1: It's on Spotify on iTunes.
• 49:12
  Speaker 3: All right, Well, I know what I'm listening to in
• 49:13
  Speaker 3: the car ride home from this.
• 49:15
  Speaker 4: This is amazing.
• 49:16
  Speaker 5: If you hate it, if you hate it, like, please lie,
• 49:19
  Speaker 5: please find me.
• 49:21
  Speaker 3: You know I can't do that. I was honest with you,
• 49:24
  Speaker 3: but I have a feeling it's going to be great.
• 49:25
  Speaker 3: Your voice is incredible.
• 49:27
  Speaker 1: Thank you.
• 49:28
  Speaker 3: Okay, last question, smartest decision you've ever made.
• 49:33
  Speaker 5: Cutting toxic people out of my life?
• 49:36
  Speaker 3: Yeah?
• 49:37
  Speaker 1: Is that allowed to be an answer? Of course. I
• 49:40
  Speaker 1: think every few years I change. I learned something new
• 49:45
  Speaker 1: about myself.
• 49:46
  Speaker 5: My perspective on the world and my role in it
• 49:48
  Speaker 5: changes and evolves. And you know, sometimes you learn new
• 49:53
  Speaker 5: things about people or about yourself that require you just
• 49:57
  Speaker 5: press delete on the relationship.
• 49:59
  Speaker 1: And I've gotten very comfortable doing that. So I'm proud
• 50:03
  Speaker 1: of that.
• 50:03
  Speaker 5: There's definitely been periods of my life where I just
• 50:06
  Speaker 5: want to be liked. I don't want drama. I choose
• 50:10
  Speaker 5: the path of least resistance. But I'm really glad that
• 50:13
  Speaker 5: I've invested in my ambition, my sense of self, like
• 50:18
  Speaker 5: who I think I am, what I think is right,
• 50:20
  Speaker 5: and not let other people like convince me out of
• 50:23
  Speaker 5: feeling those things.
• 50:25
  Speaker 3: Snaps for Ali. Thank you for your time and for
• 50:29
  Speaker 3: enlightening me. I love when people change my mind about things.
• 50:33
  Speaker 3: I love being wrong, and you've done that every time
• 50:36
  Speaker 3: we've spoken.
• 50:36
  Speaker 4: So thank you, thank you.
• 50:38
  Speaker 5: And it's not that you're wrong, it's that you can
• 50:40
  Speaker 5: have your own feelings and opinions. I can have my own,
• 50:43
  Speaker 5: and we can both refine them together. I don't believe
• 50:46
  Speaker 5: in this like black and white, right and wrong. Like
• 50:49
  Speaker 5: you're entitled to what you think and believe. I'm entitled
• 50:51
  Speaker 5: to the same, And I think more people just need
• 50:53
  Speaker 5: to share those thoughts and feelings openly and we'll probably
• 50:57
  Speaker 5: build a better world. Okay, I don't know why this
• 51:00
  Speaker 5: went all hockey, but thank you for having me to Neil.
• 51:20
  Speaker 3: All right, today is a good day to have a
• 51:21
  Speaker 3: good day.
• 51:22
  Speaker 4: I'll see you next week.