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.

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).

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).

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).

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).

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

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).

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).

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

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)

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

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.

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.