Join a startup, or go corporate?

Published: Wed, 05/27/26

Updated: Fri, 05/29/26

May 27, 2026

TOGETHER WITH

Welcome back. It’s hard to believe that we’re almost in June, though it’s also hard to believe a kid graduating college this year was born around 2004 (they will be in sales soon). In this week’s issue, we’ll look at the history of magazine subscription sales. Then, a Sales Fail about an internal champion, and the usual fun. Let’s do this.

NUMBER OF THE WEEK

10,000 & 15,000

Most companies will spend between $10,000 and $15,000 on hiring a single sales rep.

Source: Zendesk

SALES ROUNDUP

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

A federal grand jury indicted five former employees of an alcohol distribution company and a Napa-based winery salesman for allegedly bribing grocery store buyers in California to boost sales of certain alcohol brands. The indictment alleges the scheme ran from at least 2016 to 2024 and involved paying bribes to employees at grocery store chains in exchange for increasing purchases of specific alcohol products. Prosecutors allege the defendants hid the bribes by using vendors and suppliers to issue false invoices. The money was then used to buy prepaid gift cards worth up to $1,000 and luxury items such as watches, purses, golf equipment and exercise gear. You can read more about it here.
A Michigan man was sentenced to life in prison after he shot and killed a Facebook Marketplace seller during an argument over whether a Mercedes or BMW is a better car. Omar Brogdon was sentenced to life in prison without the possibility of parole on May 18, according to court records. Brogdon was sentenced in the Michigan court in connection with the shooting death of Orhan Hosic, who prosecutors said met up with Brogdon in 2024 at Hosic's Fenton Township, Mich. home. At some point, the two men got into an argument over whether Mercedes or BMW produced better cars. You can read more about it here.

FEATURE

The Kids Who Knocked on Doors Selling Magazines

In the decades before the internet, magazine subscriptions were one of the largest direct-sales businesses in America.

By the middle of the 20th century, magazines had become a central part of American life. Titles like Time, Life, Reader’s Digest, Look, Sports Illustrated, National Geographic, and Better Homes & Gardens reached millions of households every month. In 1954 alone, Reader’s Digest had a U.S. circulation of more than 13 million copies. Life magazine regularly reached over 20 million readers during its peak years.

For publishers, subscriptions mattered enormously. A loyal subscriber was predictable revenue, but more importantly, high circulation numbers allowed magazines to charge advertisers more money. The larger the audience, the more valuable each page of advertising became.

That demand created an entire sales ecosystem.

By the 1950s and 1960s, independent subscription sales agencies were operating across the country. Some focused on direct mail campaigns, but many relied on door-to-door sales crews made up largely of teenagers and young adults. Publishers outsourced aggressively. The crews handled the selling while the magazine companies handled fulfillment and printing.

Here’s how the business was structured: crews bought subscription packages at wholesale rates and kept the difference as commission. A rep selling a two-year subscription to Sports Illustrated or Newsweek might only keep a portion of the sale, but volume made the model work. Managers pushed reps to knock on as many doors as possible.

Entire companies formed around the practice. Organizations like Southwestern Company became famous for sending college students door-to-door each summer selling educational books and subscriptions. Other traveling crews were far less formal. Vans of young salespeople moved city to city, staying in cheap motels while managers mapped out neighborhoods each morning.

Reps were taught how to approach homes, how to stand at the door, how to avoid sounding nervous, and how to keep a conversation alive long enough to make a pitch. Many used emotional hooks. Some claimed they were competing in scholarship programs or sales contests. Others leaned on patriotism, education, or supporting young workers trying to “get ahead.”

By the 1970s and 1980s, magazine crews had become a recognizable part of American suburbia. Publishers were locked in circulation wars, and subscriptions were everywhere. Consumers signed up for magazines at shopping malls, grocery stores, over the phone, and at their own front doors.

The business also developed a darker reputation.

Investigations over the years uncovered crews operating under misleading pretenses, withholding commissions, or recruiting vulnerable young people into exhausting travel schedules. In 1971, Congress passed the federal “Cooling-Off Rule,” giving consumers three days to cancel certain door-to-door sales purchases, partly in response to aggressive in-home selling tactics that had become common across industries, including magazine subscriptions.

By the 1990s, the economics started changing. Cable television fractured audiences and advertisers found new places to spend money. Then the internet arrived and completely altered the subscription business.

Publishers shifted toward websites and digital advertising. And print circulation declined sharply. Newsweek ended its print edition in 2012 before later relaunching it in limited form. Life magazine had already ceased weekly publication decades earlier. Hundreds of smaller magazines disappeared entirely.

The sales crews faded with them.

Door-to-door subscription selling still exists in small pockets today, but the industry no longer occupies the place it once did in American culture. For decades, though, it served as an unlikely training ground for young salespeople. Thousands of reps learned cold approaches, objection handling, persistence, and rejection recovery while standing on strangers’ porches trying to convince them they needed another magazine in the mail every month.

The business disappeared slowly enough that most people barely noticed. One year the neighborhood kids were selling magazine subscriptions. A few years later, the magazines themselves were disappearing too.

Your next top rep may be an agent.

Your buyers will soon have agents. But have you really bullet-proofed your GTM for this new reality?

On June 23–25, top CROs and revenue leaders, including Mark Roberge, CROs from ZoomInfo, ElevenLabs, SAP, and Vercel, will share how they’re adapting to this shift.

Everything in GTM is becoming digitized, which means every workflow becomes measurable, improvable, and eventually autonomous. The best revenue leaders will learn how to operationalize AI across forecasting, qualification, pipeline management, and execution.

Join one of the most forward-thinking AI events in B2B this summer.

Virtual. Free. June 23–25.

MEME OF THE WEEK

Source: Instagram -- sales_humor

QUIZ

What does the SPIN in SPIN selling stand for?

A. Serve, Produce, Improve, Negotiate
B. Situation, Problem, Implication, Need-payoff
C. Solution, Procurement, Importance, Net Revenue
D. Separate, Pinpoint, Improvise, Networking

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).

A friend of mine referred me to one of his friends who worked at a pretty big company. He told me the guy was well connected internally and said they were actively looking at new CRM software, so I treated it like a massive opportunity.

I spent days prepping for the demo. I built custom slides, looped in my manager, and rehearsed the whole thing multiple times.

The call itself felt weird almost immediately. The guy was polite, but low energy. He barely asked any questions. I kept mentioning the mutual connection, expecting it to help move things along, but he didn’t really say much about it.

Near the end, the guy goes, “So, I probably should have mentioned this earlier, but I just gave my notice. I will definitely refer you internally though—the guy taking over for me is a really good dude.”

My heart sank. I basically knew the deal was dead. And guess what? It was. I followed up with the replacement at least five times and never heard a word back.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- May 2026

WORTH A PEEK

Have you ever found out during the interview that you didn’t actually want the job? Someone recently asked this question on Reddit, and got some fun stories in response. You can see the 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’m stuck between two job offers and really having a hard time deciding.

The first offer is at a startup that recently raised a pretty big round of funding. It has a high base, bigger OTE, equity, and honestly a pretty “exciting” product. The people seem sharp and the company feels like it has momentum. The downside is it’s obviously riskier. I’d probably be working harder, and there’s always the (big) chance the company flames out in two years.

The second offer is at a large, established company. Lower base and lower upside overall, but more stable. It feels safer, but also feels like I already know exactly what the next five years would look like there.

I’m 31, no kids, decent savings, and currently employed, so this isn’t a desperation move either way. Part of me thinks this is the exact time in my life I’m supposed to take a swing. The other part of me thinks people romanticize startup risk after hearing survivor stories from the small percentage where it worked out.

How do I actually decide without just flipping a coin?

Deciding in Location Withheld

Dear Deciding,

At 31, with savings and flexibility, you’re in a better position to take career risk than you may be later. But don’t confuse “startup” with guaranteed growth or excitement. Plenty are chaotic, poorly managed, and miss numbers for years.

The biggest factor is probably the manager and team quality. A great manager at a stable company will usually help your career more than a messy startup with a flashy pitch deck—unless it hits, of course.

Also: you’re not choosing forever. You’re choosing your next few years. That should take some of the pressure off.

Quiz Answer: B. The SPIN in SPIN selling stands for Situation, Problem, Implication, Need-payoff.

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Today's email was written by Ken Kupchik and Steve Rado.

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