Mar 3, 2025 · 34m · the-pitch
#41 Can This Startup Help Retailers Take on Amazon?
Chelsea Lee · 7m spoken Josh Muccio · 7m spoken Phil Nadel · 3m spoken Michael Hyatt · 3m spoken Jillian Manus · 2m spoken Charles Hudson · 1m spoken Nicole Verkindt · 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
Chelsea Lee pitches Shipsy, an on-demand delivery aggregator helping independent retailers compete with Amazon's shipping speed, securing over $600,000 in on-air commitments before post-show market shifts and diligence timelines reshape the investment outcomes.
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 29.5% of the talking time here. How this is scored →
Josh as informed peer 2.1 Guest teaching 3.4 Guest disagreement 2.1 Josh pushing back 1.7
speaking balance: gold is Josh, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:25 Phil rejects sound bite reduction
Phil forcefully tells Josh that he gave a nuanced answer and refuses to let it be reduced to a simplistic sound bite about cooling off.
Hardest push from Josh ▶ 20:45 Josh presses on investor communicationJosh refuses to let Chelsea's vague explanation stand, repeatedly challenging her on whether she sent an explicit warning email before the round closed.
Biggest teaching moment ▶ 25:48 Jillian corrects timeline assumptionsJillian corrects Josh's assumption that Amazon is a distant 5-to-10-year threat, demonstrating how fast their new small business partnerships move.
Josh holds their own ▶ 30:54 Josh synthesizes market risk to ChelseaJosh articulates the detailed rationale from all three investors, directly countering Chelsea's claim that Amazon's moves do not impact her business model.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Josh as informed peer | Guest teaching | Guest disagreement | Josh pushing back | Why |
|---|---|---|---|---|---|---|
| Chelsea Lee Presents the Shipsy Solution | 1 | 3 | 1 | 0 | Chelsea introduces Shipsy's core value proposition of one-hour local delivery. When questioned on shopping cart abandonment figures, she cites data from the NRF census study. | |
| Exploring the Business Model and Platform Integrations | 2 | 3 | 2 | 1 | Investors examine Shipsy's SaaS and transaction fee model. Nicole pushes back on the five-dollar fee feeling steep, but Chelsea clearly breaks down how it saves retailers money over traditional parcel shipping. | |
| Aggregation Defensibility and Logistics Redundancy | 1 | 4 | 2 | 0 | Phil queries why delivery platforms would not just build Shopify plugins themselves. Chelsea and Charles explain how multi-courier aggregation and redundancy are vital to merchants. | |
| Traction, Financial Projections, and Valuation | 1 | 4 | 2 | 0 | Chelsea shares early revenue metrics and candidly points out that early-stage projections are rarely accurate anyway. She details bootstrapping customer service on her personal phone. | |
| Investor Deliberations and Offer Commitments | 1 | 2 | 1 | 0 | The panel negotiates commitments with Phil offering $300k, Jillian offering $150k, Michael committing up to $100k, and Charles pledging pending conflict checks. | |
| Post-Pitch Follow-Up: An Oversubscribed Round | 3 | 4 | 2 | 4 | Josh follows up with Chelsea after the round becomes oversubscribed by outside venture capital. Josh presses on whether the pitch investors were dropped or failed to follow up. | |
| Phil Nadel on Amazon Threat and Timing | 4 | 3 | 5 | 4 | Phil explains why he backed out, pointing to Amazon's logistics moves and syndicate closing timelines. When Josh tries to summarize it into a sound bite, Phil firmly pushes back against the simplification. | |
| Jillian Manus on Amazon Expansion Risk | 2 | 5 | 2 | 3 | Josh asks Jillian whether Amazon's expansion is a distant threat. Jillian educates him on Amazon's recent SMB partnerships and predicts aggressive encroachment within one to two years. | |
| Michael Hyatt on Due Diligence and Speed | 4 | 3 | 2 | 3 | Michael Hyatt outlines his due diligence time limits, and Josh relays investor concerns back to Chelsea, who remains unbothered by Amazon's news. |
Statements from this episode (20)
Chelsea Lee: Slow delivery caused $135B in cart abandonment last year
“There was over seven hundred billion dollars last year alone left in total shopping cart abandonment. Of that, one hundred and thirty five billion was left specifically because people couldn't get their shampoo fast enough or people couldn't get their air, air…”
Lee: Average cost to ship a package in the US is $12
“The average to ship a package in the U.S. Is 12 dollars per, per package.”
Hudson: Retailers will not build separate integrations for individual delivery apps
“And the retailer, the retailer's not gonna do seven integrations for one hour shipping. They're not gonna do a separate integration for Uber, Postmates.”
Chelsea Lee: All e-commerce logistics will be on-demand in 3-5 years
“Fundamentally, we believe that all logistics will be on demand. All e-commerce will be on demand in the next three, five years, right?”
Hudson: Delivery redundancy is essential as single-network capacity fluctuates
“I think redundancy is valuable for retailers because you remember these networks are, they stretch and they grow. You might hit a point where all the Postmates people are out delivering lunch.”
Lee: Shipsy is raising $1.5M at a $4.5M valuation cap
“My co-founder, Ben Way, threw in the first three 50 and built the API, and then after that we did a friends and family and raised three 80. We're currently raising 1.5 at a 4.5 cap in convertible notes. Of that we have 800 closed or committed, so looking to fi…”
Hudson: A single shipping API becomes more valuable as logistics complexity grows
“Having one single API for this stuff, it becomes way more valuable over time because logistics just gets more complex.”
Hudson: Shipsi will end up relaxing its one-hour delivery promise
“I don't think one, I think you're going to end up relaxing this one hour thing.”
Lee: Shipsi's $1.5M round is oversubscribed by $1M with three leads
“So we set out to raise 1.5 million, and we're oversubscribed by a million with three leads, and everyone in is a strategic investor, even, even our angels, and we had to turn quite a few away.”
Lee: Pitch investors backed out before Shipsi could offer allocations
“They bowed out before I could even say, look, we're oversubscribed. Do you want in or not? Like, I'd love to have you. But they bowed out before we even got to that point.”
Muccio: Charles Hudson still intends to invest $250K in Shipsi
“I found out shortly after this that Charles is actually very much still interested in investing. Like he wants to put in the 250 K that he wanted to invest originally, which is huge.”
Nadel: Amazon's delivery network threatens Shipsi's business
“They're building their own delivery network, which has significantly bad implications for Shipsy in my view.”
Nadel: Officially passes on investing in Shipsi post-show
“So so for all these reasons, I'm going to have to pass.”
Manus: Amazon will compete in retail delivery within one to two years
“I'm thinking more like a year down the line. I'm thinking a year to do two years down the line. I, to be able to turn that on is nothing for them.”
Hyatt: Amazon shipping announcement prevented his investment in Shipsi
“And then right afterwards Amazon kind of came out and said they're getting into the kind of shipping business and kind of making it shipping for all. And I think that muddied the waters a little for me. I just couldn't get comfortable enough that they were goi…”
Hyatt: Better to pass than give in to FOMO without diligence
“After a show typically there's a buzz around these companies, and they all gonna raise their round extremely quickly, within a matter of weeks, and if you can't do due diligence enough, ask enough people, you can't, if you don't get enough comfort, then it's b…”