Mar 3, 2025 · 37m · the-pitch
#20 Harper Wilde
Josh Muccio · 7m spoken Jenna Kerner · 6m spoken Jane Fisher · 6m spoken Daniel Gulati · 4m spoken Jillian Manus · 4m spoken Phil Nadel · 1m spoken Charles Hudson · 1m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Entrepreneurs Jane Fisher and Jenna Kerner pitch Harper Wilde, a simplified direct-to-consumer bra company, navigating investor skepticism about past industry failures before overcoming a unanimous panel rejection to secure outside funding.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Josh holds 26.9% of the talking time here. How this is scored →
Josh as informed peer 3.9 Guest teaching 2.9 Guest disagreement 2.1 Josh pushing back 3.1
speaking balance: gold is Josh, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:01 Calling out Daniel's pain point premise
Jane directly challenges Daniel's critique that bra shopping lacks a 10x pain point, bluntly stating his perspective is off base because he does not buy or wear bras.
Hardest push from Josh ▶ 14:30 Daniel questions whether the product is 10x betterDaniel directly challenges whether Harper Wilde solves a real venture-scale pain point if consumers are already content buying cheap bras at Target.
Biggest teaching moment ▶ 17:36 Explaining the reality of buying bras at TargetJane educates the room that women buying bras at Target does not signal customer satisfaction, but rather utter frustration with the existing buying process.
Josh holds their own ▶ 20:05 Phil breaks down the valuation mismatchPhil demonstrates investor rigor by contrasting Harper Wilde's $20k monthly revenue with their $9M valuation cap, decisively justifying his pass on concrete venture economics.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Josh as informed peer | Guest teaching | Guest disagreement | Josh pushing back | Why |
|---|---|---|---|---|---|---|
| Founders Pitch Harper Wilde and the Problem with Bra Shopping | 1 | 2 | 1 | 1 | Jenna and Jane deliver their opening pitch about the hassles of traditional bra shopping and the dominance of antiquated incumbents. The investors primarily listen as the founders frame their market opportunity. | |
| Testing the Model and Presenting the Product | 2 | 3 | 1 | 1 | The founders describe their lean validation experiment involving 400 bras and 50 women in Philadelphia to prove the home try-on model. The investors inspect the physical product samples without challenging the methodology. | |
| The Try-On Model and the Shadow of True&Co | 5 | 4 | 4 | 5 | Daniel Gulati argues that free home try-on is merely an easily replicable tactic, which Jane directly counters by detailing the heavy logistical and inventory complexity. Gillian presses Phil and Charles on the failure of True&Co, bringing past portfolio scars into the room. | |
| The Brand Loyalty Debate and Everyday Functionality | 4 | 3 | 3 | 4 | Gillian challenges the assumption of customer loyalty by citing her own diverse, non-loyal shopping habits across Target and Victoria's Secret. Jenna defends their positioning as an everyday functional staple rather than a trend-driven fashion item. | |
| Evaluating the Pain Point, Valuation, and Traction | 5 | 6 | 6 | 6 | Daniel questions whether the product solves a sufficient pain point compared to cheap Target alternatives. Jane sharply pushes back, pointing out Daniel is off base because he does not wear bras and that resorting to Target reflects desperation rather than satisfaction. | |
| Investor Decisions and Final Feedback | 6 | 2 | 1 | 7 | All four investors systematically pass, delivering pointed critiques regarding valuation, category graveyard risks, brand conviction, and physical product finishing. The founders listen politely as the rejections are delivered. | |
| Post-Pitch Deliberation Among the Investors | 6 | 0 | 0 | 0 | In an investor-only post-mortem, Daniel, Charles, Phil, and Gillian debate whether past venture failures in the direct-to-consumer bra market should disqualify new entrants. Because the founders are out of the room, combativeness and schooling are non-existent. | |
| Mid-Show Break and Sponsor Transition | 2 | 3 | 1 | 1 | Josh conducts a follow-up interview with Jane and Jenna to discuss gender dynamics in venture pitches and their subsequent funding traction. The tone is collaborative and reflective. |
Statements from this episode (16)
Kerner: One Bra Industry Incumbent Controls 60% of the Market
“And for me, I thought about the incumbents in the industry and where I could possibly go, one of whom owns 60% of the market, and these new incumbents have not chipped away at that.”
Kerner: Victoria's Secret's Hypersexualized Branding Fails Modern Women
“Yeah, we were trying to be, ah, polite, but yes it's completely hypersexualized, so antiquated, and, you know, the embellishments, the, you need a padded version, the uncomfortable experience that's not what's resonating with the modern, empowered woman.”
Harper Wilde Tested Try-On Model Using 400 Existing Bras at Zero Net Cost
“We bought 400 bras of existing brands and we found a way to basically replicate the purchasing process and test it for zero dollars to us”
Kerner: 65% of Harper Wilde orders come from Free Home Try On
“About 65% of our orders do come through this Free Home Try On model, and we see a 110% conversion.”
Gulati: Home try-on is an easily replicable tactic, not a moat
“Home try on is like a tactic, not a, it's a tactic that can be replicated, obviously.”
Fisher: Free home try-on is not easily replicable due to inventory complexity
“Actually free home try on is not easily replicable. The ability to operationally have enough inventory to buffer a free home try on logistical model is actually very complex.”
Muccio: Investors Charles Hudson and Phil Nadel previously invested in True&Co
“What Jillian is alluding to is that Charles and Phil both previously invested in a broad startup called True&Co.”
Gulati: Harper Wilde is not a 10x improvement over Target bras
“And so like, this seems like it's a little bit better for sure. But it's not, obviously, at least not to me, like, tenx better than the Target bra.”
Fisher: Harper Wilde Raising at $9M Valuation Cap With 20% Discount
“This one's a nine million with a 20% discount.”
Kerner: Harper Wilde Hits 25% Monthly Growth With Over 2,200 Orders
“Yeah, so we're we've had around 25% month-over-month growth since launch. We're at over 2200 orders, so around 20,000”
Kerner: Harper Wilde projects $150K revenue this year and $2.2M next year
“Anticipated to be around 150,000 this year and then getting to around 2.2 million for next year.”
Phil Nadel: Cannot justify $9M cap for Harper Wilde at $20k/month
“I can't justify paying, what was it, a nine million dollar cap when you're currently at 20,000 a month. And you know, for that reason alone it just doesn't work for me. So I'm gonna pass, but good luck.”
Daniel Gulati: Skeptical of bra category due to past startup failures
“Like for us to make a brand bet, we really need to be excited about the category and between the many tombstones kind of that have that have existed as well as Just the consumer behavior. I'm just like not a hundred percent bought into the category.”
Gulati: DTC brands cannot be continuously iterated like software
“To be a true billion dollar direct consumer brand, like the brand has to resonate and brand isn't one of those things you can necessarily iterate on. I don't believe, like, I think The consumer thinks what they think of you, and I think you can evolve a brand …”