Nov 29, 2023 · 37m · more-or-less
Bonus: A Conversation with Erin and Sara Foster on Everything Founders are Afraid to Say · More or Less Podcast
Erin Foster · 14m spoken Sara Foster · 12m spoken Jessica Lessin · 5m spoken Brit Morin · 26s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Recorded live at The Information's WTF Summit, sisters Erin and Sara Foster join host Jessica Lessin to discuss how they leveraged self-awareness, radical authenticity, and strategic partnerships to transition from Hollywood creatives into successful founders and venture capitalists.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 16.2% of the talking time here. How this is scored →
The hosts as informed peer 2.4 Guest teaching 3.1 Guest disagreement 2.2 The hosts pushing back 1.1
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:20 Mocking standard startup investor expectations
Erin directly attacks a cornerstone tech investing convention, calling it insane that founders are forced to declare target demographics before customer validation.
Hardest push from the hosts ▶ 24:33 Host insists on fund size disclosureWhen Erin deflects about whether they are allowed to state their fund size, Jessica directly cuts off the hesitation with 'Of course you can say,' compelling Sara to reveal the ten million figure.
Biggest teaching moment ▶ 25:45 Rejecting conventional equity wisdom for supply chainSara and Erin educate the tech audience on why they deliberately ignored universal advice against giving away half their company, choosing operational sanity over full ownership.
The host holds their own ▶ 16:04 Citing dismal podcast industry economicsJessica counters general enthusiasm about podcasting by sharing real data from media executives showing that 18 out of 19 shows operate at a steep loss.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Unlikely Entrepreneurs and the Power of Being Underestimated | 2 | 2 | 2 | 1 | Jessica opens the live summit session by introducing the Foster sisters' diverse portfolio across retail, Hollywood, and venture capital. Erin and Sara playfully frame their non-traditional business entry around being underestimated and fueled by revenge. | |
| Launching Favorite Daughter and Faking Investor Demographics | 2 | 4 | 5 | 2 | The sisters recount their path from a comedy show to Bumble and retail merchandise. Erin sharply calls out standard tech pitch dogma, mocking the expectation that founders must invent an exact customer persona before product-market fit. | |
| Building Brand Authenticity and Avoiding Celebrity Pitfalls | 3 | 3 | 2 | 1 | Jessica inquires about retail strategy and mentions that most celebrity-backed brands fail. The guests contrast why Skims succeeds due to authentic usage while highlighting their own accessible price-point strategy. | |
| The Pressures of Brand Identity and Grassroots Hustle | 3 | 3 | 1 | 1 | Jessica and the guests agree that influencer gifting and unboxing videos have lost efficacy with consumers. Sara recounts grassroots marketing efforts, including passing out flyers at college-adjacent hotels. | |
| Podcasting Success and Reinventing Past Career Identities | 5 | 2 | 1 | 2 | Jessica brings media insider context, noting that media companies often see eighteen out of nineteen podcasts lose money. Erin and Sara explain their low-overhead approach and intentional choice to avoid oversaturated press-tour guests. | |
| Navigating Decade-Long Career Rejections in Hollywood | 1 | 3 | 1 | 0 | Erin shares a vulnerable monologue about turning 30 after being fired and enduring a decade of unproduced writing work. Jessica listens without interrupting as Erin describes the slow reality of Hollywood success. | |
| Developing 'Shiksa' and Hollywood Writers' Strike Insights | 4 | 4 | 3 | 3 | Jessica pushes the guests to disclose the size of their venture fund, cutting through their hesitation. Sara and Erin explain their counterintuitive choice to give away 50% equity to an operational partner rather than taking on supply chain debt. | |
| Audience Q&A: Founder Red Flags and Egos | 1 | 4 | 2 | 0 | During audience Q&A, an attendee asks how the sisters evaluate founders. Erin shares a major red flag: founders prioritizing personal branding and Forbes covers over their actual product. | |
| Audience Q&A: Trusting Gut Instincts When Saying No | 1 | 3 | 4 | 0 | The sisters playfully spar over their interpersonal conflict, communication styles, and moral codes. Sara reveals she performs word gymnastics to avoid rejecting founders directly, while Erin sends blunt rejections regardless of founder status. | |
| Future Vision and the Connected Foster Business Ecosystem | 2 | 3 | 1 | 1 | Jessica asks about their two-year outlook, prompting the sisters to explain their cross-promotional business flywheel. Jessica wraps up the fireside session with positive remarks about their non-traditional hustle. |
Statements from this episode (15)
Erin Foster: 'Favorite Daughter' t-shirt outsold Suburban Riot's famous 'Kale' sweatshirt
“One of the sayings that we put on was favorite daughter. That one ended up outselling the kale sweatshirt, which we just didn't expect that to happen.”
Erin Foster: Demanding exact customer personas before a product launch is insane
“One thing that I never understand in tech, and everyone here will probably disagree with me, or maybe agree with me, is that when you start a business, you're supposed to tell your potential investors exactly who your customer is before your product exists, an…”
Erin Foster admits fabricating Favorite Daughter's target customer persona for investors
“For us, when we started Favorite Daughter, they said, like, who's your girl? And we're just, like, making things up, you know? Like, I don't, she's, like, just graduated college, and she's, like, going through a breakup, and she wants to buy her first blazer t…”
Sara Foster: Favorite Daughter reached profitability in its third year
“It's a profitable business year three, and we all know that's hard to do.”
Erin Foster says TV writers build careers without shows ever airing
“You can make a real career out of being a TV writer without anything ever airing, because they pay you to write it.”
Erin Foster sold a comedy starring Kristen Bell and Adam Brody
“I sold a show that Kristen Bell is gonna play me, and Adam Brody is playing my husband, but it's as if my husband was a rabbi”
Erin Foster says writers like the strike deal, but studios do not
“The writers that are working for me, they feel very good about the deal, and I think that, you know, writers have always felt really beholden to studios and networks, and it feels like the networks and studios are not happy about where we landed, and the write…”
Sara Foster reveals Oversubscribed Ventures raised a $10 million fund
“It's ten million. We raised ten million.”
Sara Foster reveals she and Erin invested zero dollars into Favorite Daughter
“Favorite Daughter is a joint venture. Erin and I did not raise money. We did not put a dollar into this company.”
Erin Foster reveals a supply chain partner owns half of Favorite Daughter
“And they own 50% of the company.”
Sara Foster: Founders asking investors what to do is a red flag
“When I'm speaking to founders and when they're pitching, when they're kind of not clear about the roadmap, Right. I get it when you're, when, but when they're not fully clear, when I find them asking me questions like, well, what would you do? Well, wait, that…”
Erin Foster: Prioritizing Forbes covers over building business is a red flag
“We meet with founders and you can see that they're thinking about their Forbes cover instead of thinking about their business. And that is a huge, huge red flag to me, because you can't be in the you business. You have to be in the business of your product, an…”
Sara Foster admits doing word gymnastics to avoid directly rejecting founders
“I never want to pass on any deals. I'm always like, whenever I want, I'm going to pass on a deal. I'm like going, I'm like doing, you know, word gymnastics without just saying like, thank you so much. This isn't right for us, but I'm happy to intro you to blah…”