Sep 23, 2024 · 1h 5m · how-i-built-this
Graduate Hotels: Ben Weprin
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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 How I Built This, host Guy Raz interviews entrepreneur Ben Weprin, detailing how he founded AJ Capital Partners and built Graduate Hotels into a $210 million narrative-driven hospitality brand rooted in collegiate nostalgia.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 35% of the talking time here. How this is scored →
Guy as informed peer 3.6 Guest teaching 2.5 Guest disagreement 0.9 Guy pushing back 1.6
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 33:28 Ousted from the Raleigh Hotel deal
Weprin describes the harsh confrontation where his equity partners abruptly froze him out of decision-making and scrapped his Rao's restaurant plans.
Hardest push from Guy ▶ 33:20 Raz presses on partner betrayalRaz refuses a soft summary and drills down on how partners could take over operations and kick out the primary deal organizer.
Biggest teaching moment ▶ 50:20 The red Solo cup humility checkWeprin illustrates his key hospitality insight by explaining how rejecting collegiate tropes was pretension, whereas leaning into authentic nostalgia made the brand work.
Guy holds their own ▶ 1:02:35 Raz outlines the real estate debt modelRaz demonstrates sharp industry knowledge by breaking down how real estate debt creates tight liquidation clocks during unexpected downturns.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Prologue: Finding Opportunity in University Nostalgia | 0 | 0 | 0 | 0 | Introductory prologue featuring a brief cold-open soundbite from Weprin followed by Guy Raz introducing the show's mission and setting the stage for the episode. | |
| The Graduate Hotels Concept and Business Thesis | 0 | 0 | 0 | 0 | Host monologue framing the Graduate Hotels business model, contrasting generic chain hotels with localized storytelling in college towns. | |
| Childhood in Dayton and the Roots of Hustle | 3 | 2 | 1 | 1 | Warm biographical banter covering Weprin's upbringing in Dayton, Ohio, his father's real estate hustle, and spending bar mitzvah savings to meet Michael Jordan. | |
| Commercial Real Estate Brokerage in Nashville | 4 | 2 | 1 | 2 | Raz guides the narrative through Weprin's early days as a commission-only commercial broker in Nashville surviving on loose change before closing his first deal. | |
| First Acquisition: The Utopia Building in Nashville | 4 | 3 | 1 | 2 | Raz presses on the financial mechanics of buying the Utopia building with a strip club tenant and how a sudden steel price spike forced a pivot. | |
| Courtship, Rejection, and Moving to Chicago | 4 | 2 | 0 | 1 | Weprin details his relationship courtship, joining Larry Levy in Chicago, overcoming imposter syndrome, and finding his hospitality calling at a Cabo resort. | |
| The 2008 Financial Crisis and Buying Out Levy's Stake | 4 | 3 | 1 | 2 | Raz probes Weprin's audacity in 2008 to buy out Levy's Auberge Resorts stake amid the financial collapse with practically no personal capital. | |
| Founding AJ Capital and Raising Eight Million Dollars | 4 | 3 | 1 | 2 | Discussion of how Weprin cobbled together over eight million dollars from retail investors, formed AJ Capital, and positioned himself to expand during the downturn. | |
| The Raleigh Hotel Deal and a Painful Business Lesson | 5 | 3 | 2 | 3 | Raz asks pointed questions regarding how Weprin's financial partners pushed him out of the Raleigh Hotel deal and what critical partnership lessons resulted. | |
| Transforming a Chicago Days Inn into Hotel Lincoln | 4 | 3 | 1 | 2 | Weprin explains acquiring a vacant Days Inn in Lincoln Park to build Hotel Lincoln, blending local cultural history with accessible hospitality. | |
| Exploring University Markets and the Ann Arbor Epiphany | 4 | 3 | 2 | 2 | Weprin recounts visiting archrival Ann Arbor as an Ohio State fan and recognizing an untapped market for university-anchored lifestyle hotels. | |
| Launching Graduate Hotels and the Solo Cup Lesson | 5 | 4 | 1 | 2 | Weprin describes launching the Graduate brand and admits his initial mistake of rejecting a red Solo cup painting before embracing genuine college nostalgia. | |
| Graduate Hotel Eugene and Localized Storytelling | 4 | 3 | 0 | 1 | A collaborative deep dive into the Eugene, Oregon property, detailing how local heritage like Nike and Steve Prefontaine shaped the physical design. | |
| The COVID-19 Pandemic and Survival Measures | 4 | 3 | 1 | 1 | Weprin details the devastating impact of COVID-19 when revenues cratered to zero, forcing massive layoffs and high-interest survival loans. | |
| Selling Brand Rights to Hilton for $210 Million | 5 | 4 | 2 | 3 | Raz explores the deal dynamics of selling the Graduate brand rights to Hilton for $210 million while AJ Capital retained underlying real estate ownership. | |
| Reflections on Success, Family, and Good Fortune | 3 | 2 | 1 | 1 | Raz poses his signature luck vs. skill question, and Weprin unequivocally attributes 99 percent of his entrepreneurial success to good fortune and family. |
Statements from this episode (15)
Weprin: Success comes down to who can 'eat the most shit'
“All the most successful people that I've, you know, read about or met, it's like, who can, you know, eat the most shit and just keep going forward?”
Weprin: Recessions create major opportunities for luxury hotel brands
“I also think there's a huge opportunity for this brand in a recession to actually, you know, acquire assets, or to, you know, build the portfolio of operational, because they're, you know, these smaller hotels, if they're in trouble, they could use distributio…”
Weprin: Larry Levy's 25% Auberge Resorts stake was $8.5M in 2008
“It was, at that time, I think, nine, it was like eight million dollars, eight and a half million dollars.”
Weprin: 15 investors backed 2008 Auberge buyout after Larry Levy rolled equity
“There was 15 people. I was short a couple million dollars at the end, and Larry, you know, decided to roll his equity into that.”
Weprin: AJ Capital acquired the Raleigh Hotel via a napkin deal
“Long story short, we end up buying that hotel. I make a deal with Frank, literally, like, on a napkin that we wrote at Macaluso's in, in, in Miami Beach for him to be the operator.”
Weprin: No hotel brand existed around university nostalgia before Graduate Hotels
“It's the idea that people take very passionate ownership of where they went to school or where they're from, and the hotel product was terrible, and no one had done it. I was like, why anybody done it? Why hadn't somebody built a brand? There's all these brand…”
Weprin: Ideas that are easy to say but hard to execute win
“Easy to say, hard to do, but that's actually a great recipe for a new business too.”
Weprin: Graduate Hotels vertically integrated ownership, operations, and branding
“We were going to become vertically integrated. We're going to own the hotel. We were going to operate the hotel. And we were going to brand the hotel. So We controlled the full customer journey and experience everything that a customer would touch, see, feel w…”
Weprin: Graduate Hotels were busier in the summer than the winter
“There was so much going on in these culturally rich, inspirational markets in the summer that we were way busier in the summer than we were in the winter.”
Weprin: Scaling hospitality requires thinking smaller to evoke local nostalgia
“The challenge as you grew bigger was to think smaller and find more stories and more history and more nostalgia and create, you know, we get this term nostalgia. You create a new memory in an old place that you'd already been that felt familiar.”
Weprin: Graduate Hotels reached 4,600 rooms and $72M revenue in 2020
“In 2020, we had 4600 rooms, and the portfolio did seventy two million dollars. Your start, we opened, you know, 15 hotels. We had another 15, 17 under development.”
Weprin: Graduate Hotels laid off 2,000 of 2,200 employees during COVID
“Yeah, corporate, we had a lot of layoffs. The property levels, we had a massive amount of layoffs. I think we laid off 2000 people out of the, I think, 2200 at the time.”
Weprin: Graduate Hotels was sold due to expensive COVID survival debt
“And this was actually, you know, why we ended up selling graduate was we took a, you know, a very large, expensive loan out during COVID to, you know, continue to execute, to deliver the projects, continue to pay our mortgages, and, you know, we made it throug…”
Weprin: Graduate Hotels would have been a $2B portfolio without COVID
“I mean, there, you know, if there wasn't COVID, if there were, we wouldn't be having, we'd be talking about us selling the entire portfolio, you know, over a two billion dollar portfolio of real estate. That'd be the conversation, you know, and the brand, or m…”