Mar 3, 2025 · 31m · the-pitch
#51 This Bot Can Fight Your ATM Fees
Paul Kesserwani · 13m spoken Josh Muccio · 5m spoken Michael Hyatt · 2m spoken Phil Nadel · 1m spoken Jillian Manus · 1m spoken Howie Diamond · 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
In this episode of The Pitch, entrepreneur Paul Kesserwani presents Cushion, an automated bot that negotiates bank and credit card fee refunds for consumers. After overcoming rigorous debates regarding technical defensibility, valuation, and bank relations, Paul secures three conditional investment commitments from the venture panel.
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 22.9% of the talking time here. How this is scored →
Josh as informed peer 4.4 Guest teaching 5.1 Guest disagreement 2.6 Josh pushing back 3.8
speaking balance: gold is Josh, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 11:20 Direct rejection of competitor capabilities
Paul immediately and forcefully shuts down Jillian's assertion that competitors like Albert could easily copy Cushion, insisting that other fintech apps lack the write-access infrastructure.
Hardest push from Josh ▶ 7:58 Feature versus platform confrontationMichael Hyatt and Phil Nadel firmly challenge the viability of Cushion, demanding proof that it is a defensible business rather than an easily quashed single feature.
Biggest teaching moment ▶ 12:44 Technical breakdown of aggregation and authentication infrastructurePaul educates the room on the architectural distinction between standard read-only data aggregators like Plaid and Cushion's custom automated action infrastructure.
Josh holds their own ▶ 16:39 Michael Hyatt scrutinizes Silicon Valley pricing vs unit economicsMichael leverages his experience scaling and selling software companies to call out the gap between unproven unit economics and a premium $10M seed valuation.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Josh as informed peer | Guest teaching | Guest disagreement | Josh pushing back | Why |
|---|---|---|---|---|---|---|
| Paul Kesserwani Pitches Cushion's Automated Service | 3 | 4 | 1 | 2 | Paul delivers an engaging pitch and interactive demo of Cushion's FeeFighter bot. The investors ask clarifying questions to understand how the user interface works without significant skepticism. | |
| Fee Negotiation Mechanics and Algorithmic Learning | 4 | 6 | 2 | 3 | Paul educates the investors on the specific negotiation mechanics, machine learning clustering, and success metrics (80% success rate recovering 30 cents on the dollar). Phil and Howie test the operational logic. | |
| Traction, Business Model, and Bank Integrations | 6 | 5 | 3 | 6 | Michael Hyatt and Phil Nadel press hard on whether Cushion is just a feature rather than a defensible platform and warn that banks might shut them out. Paul counter-argues by detailing their long-term platform vision including unclaimed property. | |
| Defensibility Clash and Jillian's Initial Pass | 6 | 7 | 7 | 7 | A tense confrontation erupts when Jillian suggests competitors like Albert could easily copy Cushion, prompting Paul to forcefully push back that other apps lack write-access infrastructure. Jillian drops out abruptly before Paul explains their 18-month technical moat. | |
| Valuation Concerns and Seed Round Terms | 5 | 5 | 4 | 6 | Michael challenges Paul's target valuation of $9-10 million pre-money for a pre-revenue company as typical Silicon Valley inflation. Paul defends the valuation citing team pedigree, lack of direct competition, and waitlist monetization potential. | |
| Paul's Background and Michael Hyatt's Offer | 3 | 6 | 1 | 2 | Paul presents his personal background and track record scaling Twitter revenue from $10M to over $2B. Impressed by his founder profile, both Michael and Phil make conditional investment offers pending a lead investor and terms. | |
| Howie Diamond's Valuation Strategy and Decision | 4 | 4 | 1 | 2 | Howie explains his strategy of waiting for later de-risked data, while Jillian admits she passed prematurely without hearing Paul's founder background and reverses her decision to join Michael and Phil. | |
| Investor Deliberation and Due Diligence Plan | 5 | 5 | 3 | 4 | The investors confer on due diligence plans after Paul leaves. Josh checks in with Paul in the post-interview, replaying the tape of the defensive clash over defensibility and having Paul reflect on why he pushed back so hard. | |
| Fundraising Progress and Lead Investor Negotiations | 4 | 4 | 1 | 2 | Josh and Paul discuss post-pitch diligence with Michael and Phil, progress securing a lead investor, and the unprecedented turnaround of Jillian rescinding her drop-out. |
Statements from this episode (26)
Kesserwani says Cushion automatically executes financial actions instead of giving advice
“Unlike other consumer finance companies out there that are just giving you advice, we're actually doing the work.”
Kesserwani seeks $2.3M to expand Cushion's bank integrations and product line
“So I'm here today raising 2.3 million dollars to grow Cushion By adding support for more banks, and building out our next set of products.”
Kesserwani: Cushion Only Supports Chase, Amex, and Wells Fargo
“We're currently only support three banks, Chase, American Express, and Wells Fargo.”
Kesserwani: Cushion secures fee refunds for 80% of users
“80% of the folks who we fought fees for have gotten money back in some capacity.”
Kesserwani: Cushion recovers 30 cents per disputed dollar
“For every dollar that we're fighting, we're getting 30 cents back right now, but we're being very aggressive because we're trying to train the model and figure out what works and what doesn't.”
Cushion has 16,000 waitlisted, 3,000 users, and fought $300K in fees
“We've built up a wait list of over 16,000 people. We've onboarded 3000 users. For those 3000 users, for only three banks and across only the last three months, 1.2 million dollars in fees that we found. So we fought 300,000 dollars of them. We've waived a 100,…”
Kesserwani: Cushion charges a 25% fee on refunded money
“Our business model is super simple. We take a 25% cut of the money we're recouping for our customers.”
Kesserwani: Cushion must build custom bank integrations due to lack of APIs
“We only support three banks today because we built brand new technology. There's no APIs or out-of-the-box way to, like, do this, so we're having to do integrations bank by bank.”
Kesserwani claims banks cannot shut Cushion down without blocking their own customers
“The way we're updating the product such that the message comes from the user, this can't get shut down, because essentially, the banks would be blocking their own customers.”
Kesserwani: Bank Fee Market Is Worth $200 Billion
“This is the first thing we decide to go after because it's a two hundred billion dollar market.”
Diamond: Invested in personal finance management app Albert
“I'm in a company called Albert. That's a personal financial mention. And yeah, they're great.”
Manus questions if competitor Albert could replicate Cushion's fee negotiation
“Then why couldn't Albert do this? They probably could.”
Kesserwani: Competitor Albert cannot take direct account actions
“No, they can't. They cannot take actions within the user's account.”
Manus: Passes on Cushion over early scalability concerns
“So I'm gonna, I'm out. And it's just because I think it's too early for me to really understand how this is going to scale.”
Kesserwani: Plaid only grants fintech apps read-only bank access
“Most folks today, if they want to start a fintech company, a consumer finance company, they connect to Plaid, or Plaid, which is a very popular data aggregator. They get read-only access to people's bank accounts. They cannot take any actions within their acco…”
Kesserwani says bank fee negotiation is only Cushion's initial product wedge
“I don't plan on being in this bank fees product for the whole company. This is just our wedge. That's working very, very well for us.”
Kesserwani: Half of Cushion's cap table is Twitter executives and former colleagues
“That's where half our cap table is angel investors from the Twitter executive team and folks I've worked for.”
Kesserwani: Cushion's existing waitlist represents $1M in potential revenue
“Just our waitlist today, if we were to monetize this, represents a million dollars in revenue. If you were just to, like, scale this out.”
Hyatt commits to invest in Cushion, pending lead investor and valuation
“I'm in if I can get comfortable with a lead and comfortable with the valuation after the show.”
Nadel: Cushion's valuation range is very high for pre-revenue
“The valuation sort of range that you're talking about is very high, especially for pre-revenue.”
Nadel says he is likely to invest if Cushion finds a lead
“If the number is reasonable, the terms are reasonable, and it's a good lead investor, then I'm likely in.”
Diamond argues valuation caps do not matter when investor conviction is high
“Whether it's six million, whether you're raising at a five million cap or a six million cap or a ten million dollar cap right now, if I have that conviction, I'm not too concerned.”
Diamond prefers to wait 12 months and pay double for proven data
“And so I can sit back and wait eight to 12 months, see how this develops, see the new implementations. See how the customers are responding. Really get some accurate data here and see what the real numbers are. And then I'll pay more. I'll pay double.”
Manus retracts her pass on Cushion and offers to join syndicate
“But I would like to see the lead. So I'm going to hop on the fill on the mic, and maybe it's even the Howie wagon, which is, I'm not going to pass because I've learned so much more, and I've learned that you don't pass prematurely when some of the key parts, w…”