The Quota reviews Broadway's Glengarry Glen Ross

Published: Wed, 07/02/25

Updated: Thu, 07/03/25

July 2, 2025

TOGETHER WITH

Welcome back to The Quota, where we cover the full spectrum of sales emotions, from overwhelming joy, to scratch-ticket-buying desperation. In this week’s issue, we’ll give you our first-ever dramatic analysis—with a review of Glengarry Glen Ross on Broadway. After that, our standard fare. Enjoy the newsletter!

NUMBER OF THE WEEK

71% of buyers went with their first choice product after creating their short list.

Source: TrustRadius

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

A 68-year-old Illinois man has been convicted of first degree in the death of a salesman following a jury trial. Eddie Bennett’s conviction stems from a previous investigation into the tragic death of Patrick Williamson, a beloved member of the community and car salesman at Monken Toyota. Williamson was killed during what police say was a robbery. Two others have been charged in Williamson’s death: 60-year-old Laura Lee Beneway, and 66-year-old Peter M. Harris. You can read more about it here.
Financial technology giant Intuit has acquired sales tech startup Relevvo, which built an AI-powered platform to help B2B companies connect with buyers more effectively. Founded in 2020 by Aashish Dhamdhere and Tushar Shanbhag. Relevvo aimed to reinvent the traditional B2B sales playbook by helping sellers identify top accounts and tailor outreach to prospects with personalized messaging based on digital footprints. Customers include Esper, FireMon, iSpot, and others. Terms were not disclosed. You can read more about it here.

FEATURE

The Quota reviews Broadway’s Glengarry Glen Ross, with Bill Burr, Bob Odenkirk, and the kid from Home Alone’s little brother

By Ken Kupchik

Upon seeing the announcement for David Mamet’s Pulitzer Prize-winning play on Broadway, Glengarry Glen Ross, featuring Bob Odenkirk, Bill Burr, and Kieran Culkin, I thought the same thing any other movie junkie who runs a sales newsletter might think—looks amazing, but a summer trip to New York? Forget about it.

Then the retargeting ads hit my news feed, and I came around to the idea that missing this play, with this cast, would be a dereliction of my duty as both a proprietor and appreciator of creative sales-centric media. Tickets were bought, hotel rooms were booked, and after braving the Times Square crowd on a Saturday night in June (highly not-recommended), I found myself along with 3 curious friends at the Palace Theater, surrounded by a Rolex and Omega-wearing crowd—tall, svelte, and mostly quite attractive.

As the curtain rose, Shelly Levene, AKA Saul Goodman, AKA Jimmy McGill, AKA Bob Odenkirk, was sitting in a leather booth less than twenty feet from me, trying to convince his sales manager, John Williamson—played by Donald Webber Jr.—to give him the quality leads, as only Bob Odenkirk could: desperately, emphatically, and with more than a touch of Goodman’s fast-talking neurosis. Odenkirk is thinner and grayer than he looks on TV. Perfect casting. Great scene. Lots of applause.

Bill Burr’s angry and unmistakable voice opened the next scene, where he sat across from Michael McKean (Jimmy’s brother in Better Call Saul), who, despite being upstaged by Burr, brought a certain level of gravitas to the performance. Burr plays Dave Moss, the disgruntled salesman who hatches the plot to steal the Glengarry leads, while McKean plays George Aaronow, his less assertive, and more moral, counterpart. Burr is excellent as the pushy, cynical Moss, and almost steals the show. Lots of laughs here. Goes by too fast.

Next scene: Kieran Culkin, sporting a patchy beard that no self-respecting 1980s salesman would ever wear, is pitching real estate to an unsuspecting bar patron. Kieran is eccentric, clever, and strangely smooth as master salesman Richard Roma, in an awkward, possibly drug-induced sort of way. But I found myself comparing Culkin’s Roma performance to that of Al Pacino, in the movie version of Glengarry. Maybe unfair to Culkin, who’s relatively new to the game, but when stacked against Pacino’s nuanced slow-boil masterclass of a sales pitch, Culkin comes off more as a nervous entry-level rep than a high-dollar heavy hitter. Still—as far as performance, it’s a load of fun.

Intermission. It’s going by too fast. I take the elevator to the upstairs bathroom in an effort to avoid the long line but find myself in a bathroomless hallway that looks less like a historic theater and more like the set of the latest Blumhouse horror flick. I get back to my seat just in time to watch the curtain go up. The bar is gone, replaced by an elaborate real estate office, complete with ceiling stains, broken windows, and a glass-doored lobby that looks so realistic, it makes me wonder if it actually leads out to the street.

There’s been a break-in. The good leads are gone! The cops are here and everyone’s a suspect, including Roma (Culkin), who just wants to know if the contract from last night already went downtown. It’s pandemonium in the best way. Culkin redeems himself in the chaos. Burr loses his shit (is he even acting?), and Odenkirk stutters and gesticulates his way through the marathon scene. It’s Mamet at his best—clipped, repetitive, profanity-laden, and the cast runs with it, playing off each other, and the audience, until, finally, unfortunately, the curtain falls.

The play is different from the movie, especially with this cast. The movie is tense and atmospheric, with none of the spontaneity and audience interaction you get from a live theater crowd. It’s also missing the famous Alec Baldwin scene, but it does just fine without it. Because the Odenkirk-Burr-Culkin Glengarry is a comedy, and not much of a tragic one. But what else can you expect when you put those three together? Three hugely entertaining personalities, all of whom bring their own flavor of fun to the performance. And that’s what it was—incredibly, unforgettably fun. Worth every penny, every cab ride, even worth braving the Times Square crowd on a sweltering June night. Five stars!

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How long you can milk being "new" before someone expects you to actually work
The art of fake apologies that preserve your honor
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Kitchen politics and why eating someone's yogurt is literally a crime
Calendar management that includes adequate crying time
Writing your resignation letter when you've been resigned since day one

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Warning: This book will not make you successful. But it might keep you sane.

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

What was the median U.S. home sale price in June 2025?

A. $480,320
B. $422,238
C. $504,002
D. $396,500

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I sell commercial HVAC systems and was running late for a big meeting with a hotel owner who'd been considering an upgrade for their property. Traffic was worse than expected, and I knew this guy had a reputation for being no-nonsense about punctuality. Panicking about losing the deal, I started speeding down the interstate, doing 80 in a 65 zone. Sure enough, flashing lights appeared in my rearview mirror. When the officer approached, I launched into a desperate explanation about my important business meeting and how much this deal meant to my family. I laid it on thick about supporting my kids and how losing this sale would devastate my month.

Somehow, it worked. I'm guessing because of my clean record. The officer let me off with a stern warning and told me to slow down. I arrived 20 minutes late to find the hotel owner waiting with his arms crossed and a scowl on his face. I immediately started explaining about the traffic and getting pulled over, hoping for some sympathy. He cut me off mid-sentence: "Show me the ticket then."

"Well, actually, I talked my way out of it," I said proudly. He stared at me then shook his head. "Right. Getting pulled over but no ticket. That's convenient." He stood up and walked me toward the door. "Next time you're going to be late to a sales meeting, come up with a better excuse than that. We're done here."

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- June 2025

WORTH A PEEK

What's something you wish you knew when you first started out in sales? For us, the answer is simple: play the long game. A Reddit user recently posted this question, and the answers are, as expected, quite fun. You can see the whole conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I sell fleet management software to delivery companies. Recently, I've been hitting a wall with prospects citing "economic uncertainty" as the reason they're not interested and are pushing conversations out later in the year. I've never ran into this problem before. My company has a great system that we sell that clearly shows ROI from cost savings, but even putting real numbers in front of them isn't moving the needle. I recently calculated that one prospect is losing $3,000 monthly through inefficiencies, but they still won't commit because it's "not the right time for new technology." How do I convince prospects to invest now instead of waiting around?

Waiting in New Mexico

Dear Waiting,

This is a cycle that affects all salespeople. Keep your head up and keep pushing through. It will get better. For now, since your ROI messaging isn't working, shift from "investment" language to "defensive" positioning. When prospects are scared or uncertain, they respond better to avoiding pain than capturing gain. Instead of showing ROI projections, start conversations with "What's your plan if diesel costs spike another 30% next quarter?" Position your software as insurance against worsening conditions rather than an investment for better times. If you try this and you're still struggling a month from now, you may want to talk to your sales manager about how you can offer smaller pilot programs (with opt-outs) so prospects can see real savings without feeling like they're making a major commitment during uncertain times. Good luck!

Quiz Answer: D. The median U.S. home sale price was $396,500 in June 2025 (you can read the source article here)

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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