Apr 4, 2023 · 59m · founders-journal
How This Founder Wants to Reward You for Paying Rent
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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 Crazy Ones, host Alex Lieberman interviews Bilt Rewards founder and CEO Ankur Jain to uncover how he transformed residential rent into a multi-billion dollar loyalty ecosystem. Jain breaks down the hidden economics of loyalty programs, first-principles problem solving, non-traditional stakeholder fundraising, and high-stakes dealmaking.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 25.5% of the talking time here. How this is scored →
Alex as informed peer 2.9 Guest teaching 3.7 Guest disagreement 1.4 Alex pushing back 0.5
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:25 Forceful dismissal of traditional venture capital
Ankur forcefully criticizes venture capitalists, stating that entrepreneurs should do everything in their power to avoid taking VC money because VCs do not understand operational needs.
Hardest push from Alex ▶ 46:05 Challenging the decision to raise outside capitalAlex directly challenges Ankur on why Bilt raised nearly two hundred million dollars if the company was already unit-profitable from day one.
Biggest teaching moment ▶ 28:50 Correcting the interchange fee flow in card rewardsAnkur politely corrects Alex's understanding of rewards mechanics by explaining how merchant transaction fees flow through banks directly back to loyalty programs.
Alex holds their own ▶ 28:05 Alex demonstrating working knowledge of credit card pointsAlex articulates the commercial mechanisms behind credit card miles and bank incentives, citing industry analyses to match Ankur's business model breakdown.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| City Banter and Uber Struggles | 3 | 1 | 1 | 1 | Alex opens with casual banter about Uber rides to Hoboken before inviting Ankur to share his family's immigrant entrepreneurial story. The interaction is deeply rapport-building and collaborative. | |
| Middle School Hustle and Overcoming Entitlement | 2 | 2 | 1 | 0 | Alex asks how Ankur avoided entitlement despite his family's wealth. Ankur recounts calling a CEO at age eleven to barter banner ads for Jump Soles shoes. | |
| Solving Problems Over Writing Business Plans | 2 | 3 | 3 | 0 | Ankur rejects the traditional business school emphasis on formal business plans and pivot models, arguing instead for solving a single durable problem. Alex validates and agrees with the framing. | |
| The Inefficiency of Rent and the Genesis of Bilt | 2 | 4 | 1 | 0 | Ankur details how rent is the single largest expense with zero return for consumers, prompting the creation of Bilt. Alex listens attentively and prompts for chronology. | |
| Reinventing Security Deposits Through Rhino | 3 | 4 | 1 | 0 | Ankur explains the dead capital trapped in security deposits and how Rhino transformed that model into monthly insurance. Alex actively mirrors the mechanics back to Ankur. | |
| Translating Loyalty Programs to the Rental Market | 3 | 5 | 1 | 0 | Ankur reveals how Barry Sternlicht explained to him that airlines and hotels make their profits from loyalty programs rather than core operations. Alex acknowledges the insight. | |
| The Hidden Economics Behind Loyalty Programs | 6 | 6 | 1 | 2 | Ankur breaks down loyalty program mechanics; Alex demonstrates subject knowledge by explaining the Chase Sapphire Reserve model and referencing airline valuations. Ankur clarifies the exact flow of interchange fees. | |
| Commercial Break | 2 | 4 | 1 | 0 | Following the mid-roll transition, Ankur discusses the friction of bringing competing real estate owners under one umbrella. Alex draws analogies to navigating intense startup hurdles. | |
| The 18-Month Regulatory Battle with HUD | 3 | 5 | 1 | 0 | Ankur recounts the eighteen-month regulatory struggle with HUD to get reward points approved for mortgage down payments. Alex reacts with enthusiasm to the dramatic turnaround. | |
| Scaling Bilt and the Perils of Business Indigestion | 3 | 5 | 1 | 0 | Ankur outlines why companies die of indigestion by diversifying too early instead of mastering distribution. Alex prompts Ankur on maintaining control during hypergrowth. | |
| Avoiding VC in Favor of Strategic Stakeholders | 4 | 4 | 4 | 3 | Alex pushes on why Bilt raised capital if it was already profitable. Ankur strongly advises against traditional venture capital in favor of strategic stakeholder equity. | |
| Hands-On Leadership and Tackling Urgent Priorities | 2 | 3 | 1 | 0 | Alex inquires about Ankur's personal time management. Ankur explains his hands-on leadership style focused purely on the top three urgent company priorities. | |
| Networking Driven by Genuine Curiosity | 3 | 2 | 0 | 0 | Alex cites Ankur's reputation as a world-class networker. Ankur demystifies networking by framing it as pure intellectual curiosity and problem-solving. | |
| Core Principles of Successful Deal-Making | 3 | 4 | 1 | 1 | Ankur breaks down deal-making into radical transparency and extreme persistence, illustrating with their negotiation pivot with Wells Fargo. Alex synthesizes the core principle. | |
| AMA: Asking the Right Questions as a Non-Technical Founder | 3 | 4 | 3 | 0 | In response to an AMA question, Ankur dismisses non-technical founder insecurity as 'complete crap' and emphasizes asking basic logical questions, sharing a pagination engineering anecdote. |
Statements from this episode (22)
Ankur Jain: Commercial Moon mining and transport will occur in 5-10 years
“Now what we're doing with Moon Express is saying, how do you create the last mile solution to get, you know, whether it's satellites positioned or whether it's, you know, going to the moon and actually mining the moon for, you know, helium three or platinum an…”
Jain: Starting a company with a business plan sets founders up for failure
“I think one of the biggest problems with business school is it loves to tell people to set a business plan with objectives and goals. And like you have, the second you start with that, you have set yourself up for failure.”
Jain: Reporting rent payments boosts an average credit score by 60 points
“The average person can increase their credit score by 60 points just by reporting their rent payments, right?”
Jain: Regulators Approved Using Rental History and Points for Mortgages
“We actually got the government, the regulators to work with us to allow your rental payment history To help you qualify for a mortgage and to use points for the first time ever is down payment assistance.”
Jain: Average residential rent in New York City is $5,000 monthly
“In New York city now, the average rent is 5000 dollars a month.”
Jain: Rhino has returned $2 billion in security deposits to renters
“We've, you know, my partner Parag is the CEO of the business, but you know, we've given back two billion dollars to renters.”
Ankur Jain: Innovation comes from applying models across industries, not thinking outside the box
“People love to use that phrase, think outside the box. Like, I hate that concept because thinking outside the box implies that you're just smarter than everybody else at that specific space. That is almost never what drives innovation. It's almost always that …”
Ankur Jain: Airlines and hotels make their money from loyalty programs, not core operations
“Airlines and hotels, I know you did a show on this, make all their money on the loyalty program and their credit card programs, not on being an airline and hotel... Delta, United, and American only exist because they make money on loyalty programs.”
Jain: Major airline market caps are lower than standalone loyalty programs
“When you combine the card business and the loyalty business with their airline business is worth less because the airline business loses so much money that the overall company Is worth less than the actual loyalty program in bank business.”
Jain: Bilt Partner Network Reaches 3 Million Apartments
“There are people who live in one of our three million apartments today, but there are a lot of people who don't. And if we, if for those people to have a solution, which is to use the built credit card, you can pay rent at any apartment building in the country…”
Jain: Silicon Valley Has Damaged Its Goodwill and Trust With Regulators
“Silicon Valley has not done itself any favors in building goodwill and trust with the regulators.”
Jain: HUD reversed its denial to let Bilt points fund down payments
“Later that day, I got an updated letter from HUD. That said, dear Mr. Jane, you're pleased to inform that your use case requested is approved, and that was that.”
Bilt reached over $5B in annualized rent processing within 12 months
“We've gone in just that 12 months to processing over five billion dollars of rent annually alone.”
Jain: Bilt has had profitable unit economics from day one
“We have unit economics that are profitable from day one, right? So we can make money and not need capital.”
Jain: Bilt has penetrated only 600,000 of 43M US rental households
“There are forty three million rental households just in the United States, much less any other part of the world. And we've only launched 600,000 of those today.”
Jain: Bilt raised $190M total and operates profitably
“We've raised, we just did a hundred and fifty million dollar round. Before that we had done forty million, but the business has been profitable.”
Jain: Founders should avoid early VC because partners lack operational understanding
“I think entrepreneurs should do everything in their power to not allow venture capitalists to come into their business. VCs don't generally understand how to run a business. They generally don't understand what your business needs are, and their incentives are…”
Jain: Bilt raised exclusively from landlords, banks, and Mastercard
“The reason we raised money was to create aligned long-term incentives with all of our partners. And so all of the money we raised was from real estate owners, the banks that we work with, Wells Fargo, Mastercar, the payment networks, And that was it.”
Jain: Bilt is rolling out full payment collection to lock in distribution
“So it's like right now we are rolling out a payment solution for every apartment building to collect all rent payments through built. So whether you pay by check or ACH or credit card or the built card, we collect a hundred percent of payments. That is my numb…”
Jain: Keeping cards close to the chest is the worst negotiation tactic
“You see this classic mistake all the time, where people think they need to keep their cards close to their chest and, like, play it coy. Like, that is the worst way to do a deal. Because the truth is that, 99% of the time, there are two or three things that ma…”
Jain: Bilt spent six months negotiating the wrong angle with Wells Fargo
“We spent so much time in the first six months talking about a credit card program with them, which was, like, totally the wrong conversation.”
Jain: Non-technical founders must aggressively question and push back on engineering timelines
“Most of technology and coding is just logic. By definition, code is a logical structured system. And so asking questions and not accepting the, it just takes three weeks, or it's not possible, or the systems don't allow you to do like the number of times you'v…”