593: Phoebe Gates: Building an AI Fashion Startup Backed by Kris Jenner & Sara Blakely

Summary

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Podcast Summary

Episode Overview

Podcast: The Foundr Podcast with Nathan Chan
Episode 593: Phoebe Gates: Building an AI Fashion Startup Backed by Kris Jenner & Sara Blakely
Date: October 3, 2025

In this dynamic episode, Nathan Chan sits down with Phoebe Gates, co-founder of FIA, an AI-powered fashion and shopping assistant app that has rapidly scaled to over 500,000 downloads and secured $9 million in funding from blue-chip investors like Kleiner Perkins, Kris Jenner, and Sara Blakely. Phoebe opens up about her entrepreneurial journey—marked by relentless prototyping, brutal feedback loops, and building in public—all while tackling the realities of privilege and carving her own founder identity separate from the Gates family legacy. Listeners will gain practical insights into starting and scaling a consumer tech company, building a standout personal brand, winning over top investors, and the future of AI in shopping.

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Key Discussion Points & Insights

1. Carving Out Her Own Identity – Privilege, Pressure, and Opportunity

• Acknowledging Privilege:
  • Phoebe openly credits her family's support and resources as pivotal to her entrepreneurial journey, including a paid-for Stanford education.
  • She addresses the "Nepo baby" label, seeing her background as a reality rather than a source of shame (30:04).

“The reality is, I am so inspired by both of my parents that I honestly think it’s a huge privilege...It’s about the privilege you’re given. Being honest, never hiding that...”
— Phoebe Gates, 02:27; 30:32

• Differentiating from the Gates Name:

  • Phoebe points out that building in fashion tech—a space her father isn't involved in—offered her both agency and a clean slate (02:27).

• Family Influence:

  • Cites the family mantra: “To whom much is given, much is required,” highlighting the responsibility to use privilege for good (31:14).

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2. From Prototyping to Product-Market Fit: The FIA Origin Story

• Experimentation & Failure:
  • Phoebe and co-founder Sophia began by testing a wide range of ideas, from a smart tampon to several B2B concepts.
  • Over 50 ideas and prototypes were trialed before landing on FIA.
  • The first FIA iteration—a desktop tool for secondhand shopping—was “horrible,” but retention was surprisingly good, encouraging further investment (04:10; 08:42).

“Every time we failed, we were like, well, that's kind of interesting. We learned something and we had the luxury of this because, mind you, we were also in college at the time.”
— Phoebe Gates, 06:34

• Iterative Development:

  • Used Figma to create early app designs and aggressively sourced feedback before building.
  • Recruited a young designer via Instagram DMs after being impressed by her portfolio (13:52).

• Pivot to Mobile:

  • User feedback revealed most shopping was done on mobile, not desktop, catalyzing a major platform shift (17:37).

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3. Aggressive User Feedback Loops & Building in Public

• Aggressive Outreach for Feedback:
  • Phoebe and Sophia DM’d over 20,000 people to recruit their first 200 beta users (15:22).
  • Segmented testers strictly between friends/family and strangers to avoid bias.

“We DM’d thousands upon thousands of people...over the course of probably two months, we had DM’d over 20,000 people. And mind you, we only got maybe 200 installs for this beta round.”
— Phoebe Gates, 15:22

• Feedback Nights:

  • Instituted biweekly "pizza and wine" sessions where 40 power users were invited in to roast the app, driving a culture of transparency and constant improvement (09:55; 19:25).

• Scientific Mindset:

  • Phoebe reframes founding as “leading a team of incredible scientists” and puts pride aside in favor of learning from data and users (17:37).

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4. Fundraising with Notable Investors

• First Funding:

  • FIA’s first check came from a Stanford professor who backed them after using their wonky prototype ($250k) (04:10; 19:42).

• Attracting High-Profile Angels:

  • Approached Kris Jenner and Sara Blakely for advisory roles, then converted them into investors; both were aligned with the company’s vision and user demographic (21:22; 22:25).
  • Prioritized strong female leaders for their cap table.

“That hack of approaching people as, ‘Okay, you’re so incredible...we’d love to bring you on as an advisor,’ and then you see...here’s the traction...‘I’m gonna put some more money in’ is really important.”
— Phoebe Gates, 23:38

• Institutional Backing:
  • Closed $8M from Kleiner Perkins to scale, public at episode release (20:00; 48:06).

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5. The Power of Building a Personal Brand & Founder-Led Marketing

• Why Build in Public?:
  • Decided in April 2025 to shift from traditional brand-centric ads to deeply authentic, founder-led storytelling and community engagement (25:14).

“We’re sick of brands, we’re sick of advertisements...we wanted to bring people in and actually get them as part of the journey...”
— Phoebe Gates, 25:14

• Content Creation as Value:

  • Launched a podcast to deliver value to potential users and foster loyalty before requesting downloads or engagement (31:51).

• Leveraging Influencer Collaborations:

  • Used social collaborations and founder accounts to amplify reach without large advertising budgets (27:10).

“As tech continues to become democratized, the thing that’s going to matter is distribution and personal brand.”
— Phoebe Gates referencing Gary Vee, 27:10

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6. Using AI to Gain Leverage

• AI in Day-to-Day Operations:
  • All employees are required to demonstrate how they use AI to automate and streamline their work (36:44).
  • Uses ChatGPT for research, interview prep, summarizing notes, critiquing marketing plans, and extracting insights from user data.

“I use AI for so much... if they don’t have an answer to that, that’s a huge issue because you’re just going to be slower than other people.”
— Phoebe Gates, 36:44

• Automation Interns:
  • Hired young automation interns tasked solely with maximizing workflow efficiency using AI.
  • Advocates for well-paid internships to maximize value and attract top young talent (38:55).

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7. Overcoming Major Challenges

• Most Difficult Moment:
  • After shifting to mobile, FIA’s onboarding was so broken during a user session that no one could access the app.
  • The team spent a month obsessively redesigning onboarding, calling it “the dark night” but learned the power of data-driven focus and resilience (43:42).

“It was like we had just spent, like, two months building this mobile application and not anyone could access it...We call that the dark night.”
— Phoebe Gates, 43:42

• Putting Ego Aside:
  • Phoebe discusses the ongoing challenge of separating her ego from feedback and content creation, and why humility fuels growth (39:42).

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8. Networking through Cold Outreach

• Cold Outreach Strategies:
  • Provides actionable advice: keep cold DMs/emails under two paragraphs, provide value upfront, and personalize every message (41:09).

“Providing someone value in that first email, then you can get them on a call and say...‘I would love to partner with you.’” — Phoebe Gates, 41:09

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Notable Quotes & Timestamps

• On privilege:
  “It’s about the privilege that you’re given. Being honest, never hiding that...But it’s also about, what are you gonna do with that privilege?”
  (Phoebe Gates, 30:32)

• On early failures:
  “The most sustainable subscription box would be a box you would just open and it’d be empty.”
  (Phoebe Gates, 06:34)

• On founder mindset:
  “My job as a founder is to be a scientist and to lead a team of incredible scientists where we’re just learning about our users and adapting to their feedback.”
  (Phoebe Gates, 17:37)

• On user outreach:
  “We DM’d thousands upon thousands of people. And so we would reach out to people and we would say, this is what we’re working on...Over the course of probably two months, we had DM’d over 20,000 people.”
  (Phoebe Gates, 15:22)

• On pitching investors:
  “We would love to give you free equity because we want to have you as part of this vision...And then from there, then she was so excited about the vision that she was willing to invest more capital.”
  (Phoebe Gates, 22:25)

• On advice to young, underestimated founders:
  “Being underestimated is a great privilege because it means you can play and you can learn in spaces where no one else can.”
  (Phoebe Gates, 46:33)

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Timestamps for Key Segments

• [02:27] – Phoebe on family influence and privilege
• [04:10] – FIA’s winding path: early failures and first prototype
• [09:55] – Real-time user feedback sessions ("pizza and wine" nights)
• [13:52] – The nuts and bolts of building FIA's first MVP
• [15:22] – Hyper-aggressive user acquisition via 20,000 DMs
• [17:37] – The importance of feedback, data, and a scientific approach
• [19:42] – First funding check and resource allocation
• [20:00] – Raising $8M from Kleiner Perkins and community building pre-launch
• [21:22] – Attracting high-profile investors (Kris Jenner, Sara Blakely)
• [23:38] – The “advisor first” strategy for landing investors
• [25:14] – Deciding to build FIA and her own personal brand in public
• [31:51] – Why founders should offer value before asking for downloads
• [36:44] – Using AI for leverage and requiring AI proficiency from hires
• [39:42] – The challenge of balancing founder role and public figure
• [41:09] – Tactical cold outreach advice
• [43:42] – The most challenging moment: broken onboarding experience
• [46:33] – How to harness being underestimated as a young founder
• [47:06] – FIA’s product roadmap: From checkout to discovery

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Conclusion

This episode is a masterclass in candid entrepreneurship, with Phoebe Gates delivering valuable tactical and strategic insights for founders at every stage. Key themes include the power of iterative prototyping, the necessity of humility, the utility of aggressive “build in public” and feedback-centric approaches, early-stage fundraising hacks, harnessing AI for leverage, and honest conversations about privilege.

Phoebe’s journey underscores that even with advantages, deep user empathy, relentless feedback, and a willingness to be egoless are the real ingredients of breakthrough startup success.

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For further insights and actionable advice:

• Check out FIA's podcast and follow Phoebe’s journey on social.
• Visit foundr.com/foundrplustrial for more resources and to join their entrepreneurial community.

Transcript

[A]

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[B]

Here are the stories. Learn the proven methods and accelerate your growth and future through entrepreneurship. Welcome to the founder podcast with Nathan Chan.

[A]

Let's start with the elephant in the room. We're here with Phoebe Gates. So you've built incredible brand, incredible company fee. You've only just launched like you are a serious hustler. This is a massive product. It's growing super fast. Really notable investors. We'll talk about that. But your dad is Bill Gates, so talk to us like what it's been like building and carving out your own identity separate from your family name.

[B]

Yeah, totally. I think for me, you know, growing up, I was super inspired by both of my parents. Right. I was 6 years old when my father retired from Microsoft. So I did get to hear some about his early days of building and what his time there was like, but I really got to see the two of them, frankly, found the foundation together and build that out. And I was always inspired by this idea of, oh, you can go create a company or you can build an idea, and you can have that be successful and then have a bunch of people that you get to work with that you love to build a dream. And so I think for me, you know, people are always like, oh, is it hard carving out your own name with your father being Bill Gates? And the reality is, I am so inspired by both of my parents that I honestly think it's a huge privilege. I mean, my college was paid for. I was able to go to Stanford, where I got the education to learn how to found a business, how to create, you know, the first prototype of our app. I wouldn't have been able to do that without the support of my parents and just the incredible amount of privilege that I have for being, you know, both of their child. I do think it is really nice, to be honest, that I'm a daughter. I think it would be a lot more challenging if I was a son building in B2B SaaS similar to what my father did. But frankly, I'm building in fashion tech, which is a very different space and not something my father's an expert in. And so that, I think, is also a huge privilege.

[A]

Yeah. So look, you've launched Fear. We recently connected, growing super fast. You only launched. We went public in April. And look, this, this. This. This product is really, really clever, what you're building as well. So I want to dive deep on how you built the product, how you came up with the idea. So take me back, Stanford. How did that influence building and, like, how you brought this product to life?

[B]

Yeah, I love this story, Nathan, because it's really a winding path. And I think for anyone who wants to build something, you know, the overnight story is me and Sophia whipped this up and we launched three months ago, and we already have half a million downloads. That's the great, you know, shiny of the iceberg. Right. But the reality is that me and Sophia met as college roommates. We argued over clothes all the time. We knew we wanted to start something together. We were really interested in a bunch of different pain points. We started out by building a prototype of a smart tampon. We looked at different B2B applications. We looked at everything, and we had so, so many failed ideas that didn't even make it past, you know, the first prototype stage. In fact, the first version of FIA was actually for a class project, and we created A desktop version where you could instantly find an alternative secondhand. And that prototype was so bad that you can imagine you're looking for a really nice purse and you want to get it secondhand or on sale, and it would show you a cane. And yet we gave it to about 200 users, and there was such high retention. And we actually started to see purchases come through, and we thought, well, that's interesting. And we realized we were money from it. And our professor for that class that we did the class project for was actually the first person to give us 250k in seed funding. And that's what it took for us to say, okay, it's time to go all heads down and build this out. Throughout the path of, of getting that funding and then actually going heads down and building, we learned, okay, people don't want it on their computer. They really want to shop on mobile. That's the future. And number two, we can't just do secondhand. We need to actually hit an even larger market and, you know, get those people to also shop secondhand. But show you, hey, does an item exist on Sal? And as we continue to, like, pull these threads, we realize there's a lot more we were really excited about just generally in the fashion and shopping space, because if you think about it, shopping really hasn't developed in the past 10 years. I mean, Amazon's great. I can get my toilet paper instantly. But this idea that there's, you know, some reason that I shouldn't be able to have a personal shopper in my pocket just doesn't make any sense because we can automate all of it. You know, personalization, curated recommendations, outfits, closet management, all with AI. And so I really feel like the tool that we've launched with today, where, you know, instantly get an item cheaper is just scratching the tip of the iceberg of what we want to build.

[A]

Yeah. So I'd love to delve a lot deeper. So tell me about, like, your first failed product with Sophia. Like, tell me about that.

[B]

Yeah, well, our first product idea was a smart tampon that could basically act the way a blood test does, so it would tell you about your health. A couple key things that we realized in that is you actually have to be the right person to build it. It might be a smart idea. I'm not actually a scientist. I have, you know, no applicable skills that would be helpful with that product. And number two, you have to want to work on it for the next 10 years. And then number three, there actually has to be a tangible market for It. And we kind of realized as we went through that idea, okay, we don't have any of those. Those three. And so we were like, okay, that idea isn't going to work. The first prototype we built, we were like, wait, there's no way that this would actually work. You know, in order to do this, we would need to be quite l like mechanical engineers to build something new. You can't, you know, just use an Arduino thing up there. So really, you know, just experimenting. But it became so, so fun right after that. We thought, okay, let's build a. A subscription box service that would be really fun. And so we modeled it out. We created a financial model. We created the first subscription box. We sent it to some people, and someone sent us a note back, and they said, you know, the most sustainable subscription box would be a box you would just open and it'd be empty. We're like, yeah, that's a really good point. Okay, back to the drawing board. But it became this game of like, okay, try and fail, try and fail. And every time we failed, we were like, well, that's kind of interesting. We learned something and we had the luxury of this because, mind you, we were also in college at the time, right? So we're able to be around, you know, a large market of different people that we could quickly talk to, get feedback from. And, you know, our jobs at the time were class. And so we were able to do this on the side, which was really, really incredible.

[A]

So how long ago was this?

[B]

This was probably my sophomore year of college. So about two years ago that me and Sophia were just in our dorm room playing with different ideas and figuring out what we could build. And then really, it's been a year since we, we founded FIA and worked on this.

[A]

Okay, so how many product ideas do you think you conceptualized and spoke to people, created a prototype, spoke to customers, see to, seeing if, getting feedback. How many products do you or. Or ideas do you think you went through?

[B]

I mean, in that year, when we were in college, before we. We built Fiat, I mean, probably 50, but I learned so much from doing it. And I talked to so many fascinating, fascinating people that I never would have spoken to. And even through this, I really just thought, this is kind of me and my best friend's adventure, right? I never thought, hey, I'm going to start, you know, $1 billion company. I want to build an AI shopping assistant. It really was this kind of, you know, intellectual journey for the two of us where we were like, well, let's just Learn about different industries, let's see what different things look like. Let's talk to different people under the guise of, hey, we're two Stanford nerds who want to learn about this space. And it actually ended up opening this door where I realized, oh, wow, there actually is a reality where our full time job could be working on something we deeply care about for a consumer. We deeply care about talking to those consumers, building with the smartest people that we know, and consistently learning. And the fact that that was actually a tangible career, Pat, I don't think we realized until we were a year in.

[A]

Yeah, so what I really respect about how you're building fear is. And you, you know, I've done a bit of research. You guys have, like every week you invite people to come into your office. Is it for pizza? Right?

[B]

For pizza and wine? Yes.

[A]

And you just get feedback for the product. Now you've taken that same kind of, you know, early stage lessons of this just aggressive feedback loop. Right. And I think if more founders actually focused on getting feedback, not tattooing their idea to their body and going, this is my idea. This is what it's going to be. This has to work and try and will it into existence and just get feedback and really focus on creating something that people want and actually want to pay for. And there's a commercial model about it. There'd be far more successful founders. So I'm curious, like for you, what were you looking for? For, for you and your co founder, what were you looking for? And to go, hey, this is the thing besides you know, the personal aspirations on, you know, this is what I get to do for work. Because I agree with you, I'm the same with founder, like, life is too short to not do work that you don't enjoy. And I feel so privileged to do the work that I do every day. I get to speak to some of the greatest founders of our generation. I get to help change people's lives for all of our products and education, coaching platforms. But like, for you, what were you looking for to know this is the product, this is what people care about, this is what's going to. This is something I can build into a real business.

[B]

You know, I don't think that there was a moment where I was like, wow, this is, this is it. But what I can tell you is that when we saw that initial traction with our first horrible, you know, MVP of it, I was like, wow, maybe there really is a space in this market. And I think that's where we got really excited about the Idea of, well, you know, in every stage, when you move to a new platform, whether that's when we move to E commerce online, when we move to mobile apps, Shopping adapted through all of those different layers. And every, you know, we saw a revolution in shopping with each of those different platform shifts. And then the question becomes, okay, wait, but aren't we in a platform shift right now towards agents? Well, what does shopping look like in that platform shift? And we started looking around and saying, okay, who's got the answer to this question? You know, we're just two kids in our dorm room. We realized very quickly no one had the answer to that. And that's where I think we saw an incredible market opportunity. And we're like, who better to build this than two young girls who are the target consumer for this, Right? I'm gonna use this tool because I love to shop online, because me and my roommate argued over clothes all the time because we were always looking for a cheaper secondhand alternative, because we were always curating collections for different people. And so it was about, okay, what is something we. Are we the right people to build this? Is there a market opportunity? And could you spend the next 10 years doing this? And for us, frankly, it checked all of those boxes and we're like, okay, let's go all in on this.

[A]

And I love the thought of, could you spend the next 10 years? Because from my experience, this is something that one of my mentors once shared with me, who's now a billionaire. It does take, you know, seven to 10 to 12 year years. Seven. It does take seven to 10 to 12 plus years, 10 plus years to build something, something of true worth and significance. That's just how long it takes. No matter how much money you raise, all that different stuff, this just takes a long time. So I'm curious, I really want to go deep on what this first prototype looked like, the exact steps you guys went through to build it. Did it cost you any money? How did you build it? Did you Vibe code? Because Vibe coding only really started earlier this year, right? Like, it's a massive movement. Like, at founder, we are, we are working on talent, like, quite like one in particular really cool Vibe coded software app. And we'll build many more. But I'm curious, like, tell me the specifics, because I think this is where sometimes in podcasts, people gloss over this stuff. And I really want to go in depth around the app pace.

[B]

Yeah, well, before we even built it, what we did is we. We actually designed it. So we use like Figma to Create like, okay, an outline, a sketch of what this is going to look like. And we started to get feedback from people. We're like, if this existed, is this a tool that you would use? And I think that's where we were like, okay, now let's go and build this. But working on it. We got another classmate to work on it. We had, eventually we, I remember we called DM to Girl, who now is a full time product designer here at Fiat. But at the time she was what, you know, 18 years old, less than 18 years old. We, we DM'd her. We're like, we think your graphic. Because we didn't know anything about what a graphic designer versus a product designer was. Like, we think your design is amazing. Like, could you design this? This is our idea. And you know, our idea is a bunch of box and circles. We're like, could you design it? And so then she gets in our figma and designed it out and then that's how we build the first version of it. And you know, it sounds like, oh, wow, that's incredible. No, it didn't work. Like, it barely worked. Right. You know, it would, you know, you were looking for a bag and it would show you a cane and yet people were still using it. And so I think that's where it was really exciting because we knew it was buggy, we knew it wasn't a full fledged product. It was like something we thrown together with sticks for a couple hundred bucks and we're like, okay, there's something here.

[A]

Yeah, okay. And then talk me through that piece where you talked about traction and people actually bought and used the product and you activated like, talk me through that and how you found those people. Because for some people that's a really scary thing. You know, just like asking random people to give feedback. Or is this something like, that's a scary thing.

[B]

We DM'd thousands upon thousands of people. And so we would reach out to people and we would say, this is what we're working on. We're two students, we would love your feedback if you have time. I think over the course of Instagram actually cut me off because I DM so many people. And it was over the course of probably two months, we had DM'd over 20,000 people. And mind you, we only got maybe 200 installs for this beta round that we wanted to do. And we curated. We'd interview the people typically before they joined, or we'd have them, you know, pass a couple parameters. Hey, do you like to shop? Do you Shop on desktop. Are you willing to give feedback? After you test it out, will you report bugs? And so we'd weed out people who weren't, you know, our target users. So we get about 200 installs. It's really hard to, especially when you're doing mobile outreach for a product, you know, with really no incentive. We're not paying people to get feedback. It was really tough, right? And so we actually cohort ties because at first we used to give it to our friends and family and they would be a lot more positive, right? They would actually use it every day because they love us, not because they love the product. And so we realized after two weeks, we're like, we're getting really positive signal, but this doesn't make sense. It doesn't work. And so we're like, okay, let's just put that in one cohort and make sure we label all of the people that we actually know. And then let's get a bunch of cold strangers that we go find and get them onto the product. And when we actually started seeing that group of complete strangers actively using it and reporting bugs and saying, hey, FIA was down today, you know, why wasn't it working? I wanted to use it for X, Y, Z. That's when we got really, really excited. And then we realized, okay, well, if we drive a sale to a site, we should be making an affiliate commission on that. At the time, we had no idea. Me and Sophia have never done sales before. We don't understand, you know, affiliate marketing. And we actually called outreach to all of the secondhand companies. So ebay, poshmark, vestaire, realreal. And we had, for the MVP, we had about 35 partnerships that we locked.

[A]

So you locked in these partnerships. Post the 200 users that activated or before.

[B]

We locked them after.

[A]

Okay, okay, okay, okay. All right. So then, so after, after that launch, like after, after you had 200 plus people kind of using the product, that's when you knew you were onto something.

[B]

I knew we were onto something. And then we came, went to New York for the summer, and both of us, you know, we're heads down and worked on it. I mean, and we tried to keep building the desktop version. And then we realized months later, hey, wait a minute, people really only shop on their phones. We kept trying to talk to what we thought was our target consumer. And they'd always say, well, I shop on my phone. And that's the important thing about those feedback nights for us, because we never want to waste the summer like we did in the past, where we focus on the wrong platform. Right. We spent so much time obsessing over the desktop extension. How's it going to look? How's it feel? Is that design? Right? Is that color blue? Right. And when we got to the end of about two months of hacking on that, we realized actually we've just been building in the wrong spot and we should have started at the top of the funnel and asked our users where they're shopping before. We just made all of these decisions ourselves. And so that is why feedback loops are so important now for us as a team doing those sessions every single other week, we have 40 of our power users come in and we ask them to roast the app and we get really honest feedback. We show them designs for future features we want to do and then we run at the top of every single week. Our team Sync is honestly all of us reviewing data and figuring out, okay, what experiments did we run last week, what did we learn from our shoppers and what experiments are we going to run this week to learn more from them? And so I think this kind of mindset shift that I had of needing to always be right as a founder into my job as a founder is to be a scientist and to lead a team of incredible scientists where we're just learning about our users and adapting to their feedback has been honestly an incredible shift in my mind and has helped a lot with, you know, the pride and the ego around. I can't tell you how many features, ideas I've had where it hasn't worked out or it hasn't been correct for our users. And having that mindset of, okay, we are scientists and learning has been really, really helpful.

[A]

Yeah, Yeah. I love, I love this mindset. It's, it's where it's at. It's, it's key. It's key. So you raised, you wrote your first check from one of your professors, 250 grand. What did you use that money for?

[B]

That was all for paying engineers, paying designers. Yeah.

[A]

And then you launched publicly in April and now you have half a million users and we're in September.

[B]

We also raised from Kleiner Perkins, which will be public when this episode comes out. And that was really important for us. Right, because we wanted the institutional investor like Kleiner Perkins, who is blue chip, to say, hey, we really validate this idea. We believe not only in the vision that they've created today, but also the long term vision of being the AI shopping assistant. And so it's really important for us to, you know, have a firm like that importantly because we wanted to bring on best in class tech talent. So we go ahead and we raise from them and then we launch. Yeah. About three months ago. And we've had, honestly, incredible traction since then. And I think a function of that is one thing we did that was really important before the launch was really building the community around the product. Whether that's the podcast where we bring on, you know, entrepreneurs that we want to learn from and ask them questions, we got our community kind of excited. And so we had people from the get go who are willing to download it and give feedback so we could continue improving.

[A]

Yeah. So I got a ton of questions I want to unpack here. So before we get to, like, the traction piece, I'd love to talk about the investment piece. Right. Because you have also. So congratulations on raising from an institutional investor. I know you've raised them from some other really notable founders like Kris Jenner, Sarah Blakely, who's one of your mentors. Like, talk me through how you raise money from them.

[B]

For Chris, we actually got connected through another female entrepreneur, and we met her at a dinner, and we ended up following up with her and pitching her. And I think there was a ton of synergy there, particularly because she has Kardashian closets. Right. Where they're already selling secondhand clothing. So she got it right away. And then for someone like Sarah Blakely, you know, her entire background, she's a genius marketer from the get go. And so that's really, really why we wanted to pitch her. And you talk about, you know, for us, it was really important to have women on our cap table, really strong female leaders who we felt like we looked up to, and then also people who resonated with the pain point. And that's also why we chose with Kleiner Perkins to have, frankly, a female partner.

[A]

Got you. And so tell me more about these conversations. Right? Like when you pitch Chris. Like, tell me, take me back to the story or when you pitch Sarah. Did you know Sarah before, you know, before you started building and going, Yep, this is what I want to build. Or like, you talk me through that. Because a lot of founders want to. Want to have, like, really notable investors on their cap table.

[B]

Yeah. I'm honestly trying to think back to the pitch with Chris. We were so nervous, to be honest. I can't tell you when we did a pitch, how many times we would practice, how we think back to, you know, the words that we would say or, you know, how we were going to phrase certain things or different questions that people could Ask. I think for us, it was always starting with, hey, we would love to, you know, talk to you about coming on as an advisor. And that's really how we started with Chris. And then she did invest because she wanted more equity as well. But when we were introduced to her, it was under the guise of, hey, we want to give you, you know, equity for free in this business. Because if we're building the next shopping assistant, you have so much credibility within the fashion space. You are known, you know, as a media mogul. And so we would love to give you free equity because we want to have you as part of this vision. We want you to have a slice of this pie and help us as we create this. And then from there, then she was so excited about the vision that she was willing to invest more capital. And so I think that hack of approaching people as, okay, you know, Nathan, you're so incredible. We'd love to bring you on as an advisor. And then you see, okay, here's the traction that this company has. And okay, I'm gonna, you know, put some more money in is really important.

[A]

Yeah, that's clever. And then Sarah. How'd you meet Sarah? And like, what did that look like when you said, hey, I want you to be an advisor?

[B]

Oh, so for Sarah, we trying to think of how we. I had met Sarah through a family friend a while before when I was just a child. And I have always been, you know, I've looked up to her so much. I mean, she is incredible, you know, going back to selling fax machines, and she pulls the car over on the side of the road and she says, I'm in the wrong movie. And she decides she wants to go and start a business. I mean, even when Spanx is blowing up, she's driving around the country to different Bloomingdale's, different Bergdorfs, and going in and pretending she's a sales rep, people don't recognize her to get feedback on the product. So I've always been so fascinated by Sarah and her innate marketing ability and also just hurt hustler and go get it attitude as a founder. And so for her, when we pitched her, it was honestly under the guise of wanting her advice on marketing. And she does invest in a lot of, you know, female founded companies. She's got, you know, her own stuff going on with sneak. So that was a pitch we were really excited about.

[A]

So when did you decide to build in public? Because I think it's really clever and it's. It's really like the unfair advantage you don't have to do it, but it's an unfair advantage. Now, for founders, when you. When you're launching any product, like building in public, building a personal brand, when did you decide and when did you start kind of like building in public? Was it earlier this year? Was it late? Because. Because, yeah, you're like, it's still early days for you. Like, it's really impressive what you've built so far, Phoebe. But, like, yeah, I'm just curious.

[B]

For us, it was really April. I want to say it was April, because we launched the podcast April 1st, and then we launched the company April 24th is when we decide to. To really build in public. And I think for us, it was this idea of we're sick of brands, we're sick of advertisements, sick of logos, and we wanted to bring people in and actually get them as part of the journey of, okay, here we are. Here's what we're building. We want your feedback on all of it. Because for us, you know, if we're building the shopping assistant, we want the women who are actually going to be using it to give us feedback in real time. And the only way to do that is not through just like a logo that they can't, you know, associate with a real person, but it's us being really honest about, hey, this is what we've built, and we want your thoughts on it. And I do think it is a huge advantage. One thing I've Learned and. Or 1 I do think it is a huge advantage, because one thing I learned from Gary Vee, who we recently had in our podcast, is he says, as tech becomes more democratized, as you have more of these, you know, vibe coding tools where anyone can build their ideas, which, by the way, is incredible. And I think it's going to democratize accessibility to ideation, to, you know, building the future that you want to see. The thing that really is going to matter is distribution and personal brand. You know, another one of our investors is Hailey Bieber. You think about, you know, the personal brand that she has created and the world that she's created with Road is so incredible. And so I think we are consistently seeing examples where personal brand and being able to relate to the founders is really, really key. Now the product needs to be incredible as well, just as it was with Rode. And so the product needs to take it to the next mile. But bringing people in is really important.

[A]

Yeah. So you really want to build that relationship with your customers at scale as deeply as possible. So you clearly see the power in you Know, building that through building in public, building a personal brand. And that, that is the future of, I think, marketing in many ways, especially for us.

[B]

Like, you know, when we're launching, we don't have a giant marketing budget. So it's all about, okay. One thing we did that was really great was we started doing collaborations with other content creators. Right. We can't afford these influencers. I have amazing friends who are influencers that I know how much they're paid. And as a startup, we're not going to be able to afford that. Right. And so we started doing joint collabs, whereas we build up the FIA social following of. Okay, we have this audience of women who love shopping. Hey, you're a shopping influencer. Why don't we do a collab together and we'll drive a bunch of followers to your account. And those really, really helped us grow. As well as founder led marketing, where we do, you know, different content. With these founder accounts and people following those are young founders themselves who want to try something new. They're early adopters. And so I think Gary Vee's lesson of, you know, as tech continues to become democratized, the thing that's going to matter is distribution and personal brand. Especially when you're up against giant, giant advertising budgets of, you know, tech monsters. You have to have something that's going to get you out there and you're going to be able to acquire customers for free.

[A]

Like to learn, learn from her around the marketing piece. What have you learned so far? I'm curious. What can you share with our community? Because she's amazing.

[B]

Yeah, I think that's the biggest thing is that you need to, basically, you need to be the face of it always. Sarah was literally the butt model for Spanx for years. Even when they were pitching to get into Nordstrom, she was the butt model. And so when she told me that story, I was like, that's it. We need to do these sessions where we let 40 women come to the office and roast us. And that's not. Oh, people on our team are running the feedback sessions. No, I run my own group. The guy who runs our ML team runs a group. Every single one of us runs a group. And when people compliment that, we're like, okay, that's great, that's great. But tell us what you hate. Tell us the worst bug you've seen, what feature is the worst. If you could wave a magic wand, what would you change about this product? And so I think the biggest thing that I've learned from her is you are your best marketing. But in order to do that, you need to be egoless, and you need to go out there and get real feedback, whether that's showing people how much you know better your butt looks in your new Spanx product or being able to say, hey, here's my app. What do you hate? What do you love? We built this, and we want real thoughts on it.

[A]

Yeah, I agree 100%. So talk me through. I guess the term Nepo baby, it gets thrown around a lot, especially in media. Like, what's your personal take on that label? When it comes to tech and entrepreneurship?

[B]

I don't think I really have a personal, novel take on it. Right. I just want to be super transparent that I have a ridiculous amount of privilege. Being born into my family and my education was paid for. I had access to go to a great university because of my parents. I had parents who support me who, you know, in everything I do. And so I honestly am not opposed to the term Nepo baby. It would be nice, you know, if my mother, you know, was a model or an actress, and I got into that stuff. I think that'd be super fun. But I definitely. I don't have an issue with that term, to be honest. I think it's. You know, I'm trying to think. Yeah, I don't have an issue with it.

[A]

Yeah, great answer.

[B]

So I think a lot of people, when people are asked about the Nepo baby thing, a lot of people want to be, like, so insulted by it. Right. I'm not insulted by being related to my parents. And if anything, I think people need to recognize that it does come with a lot of privilege.

[A]

Yeah. And look, I think just as. As we've connected, it's pretty clear that you are carving out, like, an incredible path. And, like, everything you're building is super impressive, and you're not getting any help whatsoever.

[B]

Yeah. It's about the privilege that you're given. Being honest, never hiding that. I know what privilege I have. I know I got an incredible education. I know I have parents that I could call for advice at any time. But it's also about, what are you gonna. What are you gonna do with that privilege? Something my grandma used to say over and over and over, and she said this even in her wedding speech to my parents. But to whom much is given, much is required. And that was something my parents said to me my entire childhood. So it was never enough in our household to get good grades or to succeed in extracurriculars. It always was what doing for other people And I think that lesson that I learned from my parents has been so, so critical. So it's okay. Recognizing the privilege you have going out there and using it to do something good.

[A]

Yeah, I really, I really respect that. So around the content piece, you've launched a podcast as well. A lot of founders, like, you're doing a lot, like, so a lot of founders necessarily think when they launch their product, they're going to launch a podcast. You've got your co host as well, your co founder. So, you know, I'm curious, why launch a podcast where, like, incredible network, you're on the unwell network. But yeah, why launch a podcast? Like, you could just create your own content? Like, why did you do that?

[B]

Because for us, it was all about how can we deliver value to our community if we're going to ask something of our community. If I'm going to ask you, hey, Nathan, will you please go download my app and tell me what you think? Think if I don't give you value before doing that, you have no reason to go do me that favor. Right? But if we're creating content with incredible entrepreneurs, which is, frankly, the content that we wanted when we were starting out, where we could ask people real questions, where it was like, hey, what was it like earlier? What's the biggest mistake you made? Or how did you learn to first fire or hire people? If you're actually providing value to your audience and giving them content that they want to engage with, which, hey, we're becoming better interviewers with, with every single episode, and we're learning, then they're going to be willing to, you know, engage with the new product that you're putting out there. And I think that's something a lot of people miss about social media is social media doesn't work if it's, you know, just an ad. An ad, or you're asking people for things, if you're providing value and then you're like, hey, we would love if you could go download our app. We're on this startup journey. You know, we're taking them along for the ride, then people are way more willing to do it. And so I think for us, it was really about, okay, what value can we provide? And one thing we knew is, okay, we have a great network of different founders that we could bring in and we could open source a lot of these conversations. And that's what we're trying to do with the burnouts. And I hope we're accomplishing.

[A]

Yeah. And why, why join a network? Why not build yourself?

[B]

We met Alex we actually cold reached out to a woman at the time that she was working with on her, like, marketing team. And pull pitched. We met her. No, we cold reach out to a woman who's working on Alex Hooper's marketing team. And then she introduced us to Alex. This is before Alex had even started unwell at the time. We're in college. We have no company. And she said, hey, these girls, they seem smart. You should. You should go talk to them. And we got on a zoom with Alex, and she said, well, what is your guys's dream? And we said, well, we want to build a company together. We're not sure what it's going to be. Da, da, da. And we started just, you know, shooting the shit and all laughing together about, you know, how we, you know, how we were trying to find, you know, engineers or when we built the thing and it crashed and we're all laughing together. And she goes, this, you know, this is. I'm actually kind of surprised. You guys are actually kind of funny. Like, did you ever think about just, like, making a podcast or filming the entire thing? We're like, yeah, but, yeah, I don't know, like, we don't have anything to film yet. And she's like, well, when you guys are starting a company and you decide on what your idea is, why don't you call me and we can do a podcast behind it and maybe you could bring in industry experts. And we're like, okay, yeah, that's a pretty. That's a really good idea. And then, you know, honestly, we. We did. When we were like, okay, we're going to do this company, we were like, who better than to work with than the top listen to podcasts for women in America? I mean, the amount of advertisement money that is spent on Alex Cooper's network is huge, and for good reason, because her audience listens to her and trusts her, and she provides them value. And so for us, getting to be a part of that network and getting to go on her daddy or to be in that marketing sphere was really important because we wanted to meet, you know, our customer, where she was at.

[A]

Yeah. And so that's massive distribution for you guys. Like, it's. I think it's really clever, by the way. I. I just. You're doing a lot, like, how do you manage your time and how do you focus? You said, I think. I don't know if we got this, but you said, you know, New York's great for you because you've got, like, adhd, but, like, how do you learn, like, what, where do you. Where are you allocating majority of your time, early stages in your business?

[B]

Yeah, I mean, it really fluctuates. Every single day is different. I mean, time is. Is a crazy thing. I have severe adhd, so if I didn't time box myself, I'd be bouncing around consistently. I do every single morning I wake up, I write down everything I'm worried about, all my goals for the day, and then I divide. Okay, what can other people do? What do I need to do today? What do I need to focus on? And I actually make time blocks for myself. It's funny because, you know, a lot of what people see are like, the podcast or us recording social clips when, like, the reality of my day to day is probably taking like five candidate interviews a day, reviewing new Figma designs, doing a couple customer interviews, you know, sitting down with Sophia and going through, okay, what's not working in the business right now? Did we forget to QA test that feature? Where do we need to, you know, make this workflow more efficient? And so I'd say a huge chunk of my time is reviewing designs, talking to users and hiring is where I'm really dedicating the majority, majority of my time. And I do my best to time box things so I don't get distracted. But we'd have to ask my co founder how I'm doing on that.

[A]

Yeah. Okay. And talk me through how much you're using AI as a founder to get leverage. I know you know, you've. You've done some. Some content around how you use chat GBT to reverse engineer viral videos, analyzing hooks like, just. But talk me through kind of how you're using it to get leverage. As an early stage founder AI is incredible.

[B]

In fact, in every single interview with a candidate, I ask how they use AI to streamline their workflow. And if they don't have an answer to that, that's a huge issue because you're just going to be slower than other people. Frankly. I use AI for so much for researching things. When I'm going to get on a call with someone I don't understand. Okay, they wrote this paper about this. I'm going to use AI to summarize this for me. Every single podcast guest you should, Nathan, you need to do this. I do a deep research on every single guest and then I have it read it out loud to me as I'm getting ready. I will use it for editing my emails. One thing I found, though, that's tough with ChatGPT and these different AI things is a lot of times it'll stroke your ego. And so I'll actually put into it, if I'm working on a deck or I'm working on, you know, a new line of business or thinking about a new feature, I will ask it to critique me. And that has been really helpful. You know, pretend you're ex founder and give me feedback on this marketing plan. I have this new idea. Am I getting distracted? How would you break it down? What KPIs should I be thinking about? Or I'll also plug into it. You know, I'll do a bunch of user interviews and I'll plug all of my raw notes into it and I'll say, hey, can you give me the top, you know, three takeaways from these, of all these people that, you know, I interviewed? Because sometimes I might, you know, really focus on one person's interview and then, you know, I let that kind of skew my perception. But if I can put that all in and then I can go pull a bunch of data, you know, directly from Our SQL or BigQuery about how people are using the product and put all that together and into chat and be like, hey, can you summarize, you know, how this is affecting our usage patterns or what we should think about or what mistakes we're making? It's so helpful. I just treat it like my personal assistant.

[A]

Yeah, I, I'm so big on it these days, using many agents.

[B]

Oh yeah. And I really think a new role, everyone talks about AI getting rid of jobs, which I am really worried about. But I think a new role that's going to come up is we just hired, over the summer we had two automation interns and they are the best decisions that we ever made. I mean, thinking about just everything in your workflow that takes busy work, what can you automate with AI? And so that we're using, you know, different like coding workflows for things like that we're building out in house tools has been incredible.

[A]

Yeah, that's really clever. That's, that's a gold tip right there.

[B]

I think finding young people for internships and paying them is, is incredible and is a huge hack. And I think being a young founder and being tapped into young networks of people who, you know, haven't gotten these giant salaries yet in big tech is really important.

[A]

Yeah, I think that's, yeah, I think that's really smart. And you know, when you bring on interns from experience, if you don't pay them, then it's about them and their experience because they're working for free. But if you are paying them them, then it shifts that kind of value equation, the dynamic 100%. So, okay, we could talk all day. We have to work towards wrapping up what's been the most challenging part of balancing being a founder, but then also a public figure.

[B]

H, that's a great question. I think, honestly, just putting your ego aside, right? Because there's times where I'm like, oh, we need to record a skit or we need to make content. How do I look? How did I sound in this? You know, what if I'm speaking about a new feature, we don't know if it's that great. I honestly think it's all about the ego. And putting that aside has been the most challenging thing because now I'm like, let's take this content. Who cares if I look good or not? Let's put it out there and learn.

[A]

Yeah, I, I, I. The amount of times I've reflected on my journey and God, you know what, if I put my ego aside, I wouldn't be experiencing this pain I'm feeling right now. And it's just like Ryan Holiday wrote this incredible book, the Ego is the Enemy. It's an amazing book. And I think, yeah, it is such a big, big thing that you have to just concentrate and keep yourself in check. So I'm also curious. You've done quite a few of your stories that you've told has been basically from cold emailing, col pitching cold dming. Like, tell me, do. What advice do you have to founders that don't, like, know a person, but they want to connect with them because you've done a really good job doing that. What advice would you give when it comes to cold dming, Cold outreaching and opening doors?

[B]

This is honestly the thing that is unlocked the most doors for me. Short subject line and always the first paragraph of the email. It. First of all, it can't be more than two paragraphs. First paragraph just needs to be valued towards you. So if I'm reaching out to you, Nathan, I'd say, hey, Nathan, I love your podcast. Here's, you know, 10 things. I think you did great in the last episodes. I noticed, you know, your, you know, maybe your what's the square called? Or I noticed your thumbnail wasn't optimized for click conversion rate. One thing we've really learned for the burnouts is we need to test. We use this new tool to test 10 different, you know, thumbnails. And I was thinking if you edited it this way, it'd Be more optimized for more clicks. And I just love your content. So I think it, you know, it should get more clicks and you know, here's some ideas I have. Would love to connect with you. No, ask any sort of value that you're providing to them before you ask is so important because that's going to get a reply. I guarantee you. If I emailed you and said, hey Nathan, I have a couple different thumbnails for you that I think would get you higher click through rate, you would 100% respond to that email versus if I said, hey Nathan, I'm Phoebe, I'm a great founder. I'd love to come on your podcast. You probably get those all night and day, right? And so providing someone value in that first email, then you can get them on a call and say, hey, you know, I would, I would love to partner with you. We'd love to work with you. I remember our first email to depop was like, please partner with us, we're college students, we'd love to work with you. And then we never got responses. Hundreds of emails were setting up no responses. I literally thought we were going to get a restraining order from the people who worked at depop. And then we started sending emails that were a little bit different. We'd say, hey, Depop, we're a group of College students. Here's 10 things we love about your platform. Here's a couple different things we should change or we'd like to change. We also are running, you know, an MVP of a tool that finds people thrifted alternatives. We've noticed these are the most popular items on your site and these are some of the trends we're seeing. And then depop would be like, oh, well, that's really cool. Like we're interested in trends about our data. Like we like this feedback. And then they would respond. And so I think really providing someone value upfront before you have an ask for them has been a huge learning for us.

[A]

Yep. Big, big fan of serving first and asking later. That's something that I learned thankfully early in my journey. And yeah, that's really great advice. So I want to talk about fair just. And we have to work towards wrapping up. It's late for you, it's early for us. What's been the hardest moment so far in building Fear and how'd you get through it? It.

[B]

Yeah. So we had just rebuilt it to be on mobile and the process of enabling a browser extension on mobile is a little bit tricky because you essentially have to toggle it on to shop with you. And you have to grant permissions for it to be able to be on the shopping sites you're on and give you those price comparisons, give you that shopping insight, et cetera. We were so excited that we finally built it for mobile. And so we invited friends of friends, about 60 women, to the office to sit and to test it, and not one of them could get onto it. The onboarding was so broken that no one could access it. And it was like we had just spent, like two months building this mobile application and not anyone could access it. And now what are you supposed to do? Because you have 60 people in the office, the thing's completely broken, and you have nothing for them to do. You have like, one box of pizza, like now this is awkward, right? And so we ended up flipping it and talking to them just generally. We had just a conversation about, you know, shopping. We all hung out, we were able to flip it. But that was so devastating because figuring out how to optimize a broken onboarding funnel took us honestly like that. Beyond building the. The app and the extension, that took us like a month. I mean, we could really not get anyone on it. And we be gay, basically. We call it. We call that the dark night. And then we said we got our PhDs in extensionology. So every single mobile extension we studied, every single screen, every button, every animation and their onboarding flow. I would have dreams about onboarding. I would have nightmares that our onboarding rate would drop. I literally had, like. I was like, scratching my head that entire month. We'd stay up all night sketching out different onboarding flows. I think that that night when we had all those women, that was super embarrassing. I'd say that was probably like one of the worst moments, but honestly, once you see a metric go from a 2% to go up, that's a really exciting point. And that period of time, as difficult as it was, we were all just focused on one goal, which was how can we make onboarding easier and better and get users to that aha moment of getting a good search result? And so while it was difficult, I think it taught me a lot about the importance of focusing on a key metric.

[A]

Yeah, I love that. Great story. Okay. Is there a belief or principle you're.

[B]

Holding onto as fear grows, don't underestimate young, scrappy talent. I think a lot of companies over index for people with incredible resumes, incredible pedigrees who have the experience. But I will never underestimate someone without the background who is willing to just get it done and learn. You need to have both. But I would say never underestimate young, hungry talent.

[A]

And for young founders who feel underestimated, what's the one piece of advice you'd give to them today?

[B]

Being underestimated is a great privilege because it means you can play and you can learn in spaces where no one else can. Right. Amazon doesn't have the luxury of being able to pivot, being able to test new features every single day, being able to run experiments. You have the privilege of being unnoticed and being. You have the privilege of being unnoticed and so you can learn and do a lot.

[A]

All right, last question. What's next? What are you most excited about? For fair.

[B]

Yeah, I really think that we've targeted users in this bottom of funnel in their shopping flow, where their assistant or the last click before checkout, where you learn, hey, is this really the right price? Does it exist somewhere else, cheaper, secondhand or on sale? Let me save it to my wish list. Really, for us, the next stage is moving towards discovery, where the fiat app becomes essentially your shopping brain. Right? Where when you open it, Nathan, it has, you know, specific collections or recommendations for you or curated offers, has your closet in there because we get to see what you're purchasing. And so I think really for us it's about moving up in the funnel and starting to really delve into this world of shopping discovery, which I'm really excited about.

[A]

Yeah, awesome. Well, look, look, I just wanted to share, look, thank you so much for sharing so much gold and wisdom with our community. It's super impressive what you've built, Phoebe. I can't believe you launched only under six months ago. You've got half a million users, you've got incredible, you know, angel investors, you know, you've now raised. How much have you raised from Klein Perkins?

[B]

We raised 8 million from Clarence Perkins, which puts us at a total of around. We raised, raised about 8 from Kleiner. So I want to say we've raised total like 9 million.

[A]

Okay, so you've raised $9 million and you've got a product that's growing super fast. Really like it's super impressive what you've built only so early in your journey. So I look forward to seeing and watching from afar how you build this billion dollar business in public. And look, I'd love to stay in touch and you're happy to come on again in the future to do a check in, but thank you again.

[B]

Thank you so much, Nathan. I, I can't tell you how much I appreciate it and I'm honored to be on and looking forward. If you ever stateside or in New York, I would love to hang out and off camera, get a drink and chat.

[A]

Hey Founder Fam. Thank you so much for tuning in today and if you enjoyed this episode, please take the time to leave us a review and let us know what you think. This podcast is a hundred percent free. We work so hard to go out and find the most, most successful entrepreneurs and founders in the world. Your feedback helps us grow, improve, and even bring on more incredible guests and insights. So if you have a second, please take a moment, leave us a review. It really makes a difference. Thanks again for listening and I'll catch you on the next show.