Business Lessons from My Idols: William M. “Bill” Gaines of MAD Magazine

My two biggest business influences have been the same since day one: my Dad and Bill Gaines, the founder of MAD Magazine. This post is the first in what may be an ongoing series, “Business Lessons from My Idols,” and this one is very personal one for me. If you grew up reading MAD you probably remember the goofy Alfred E. Neuman and the magazine’s parodies, but you might not know the man behind the magazine. Bill Gaines was MAD’s longtime publisher (over 40 years) and the architect of a work culture so unique and fun, it arguably set the template for the modern “creative office.”

Who Was William Gaines? (And Why He Matters)

To meet Bill Gaines, you’d never guess he was a successful publisher. Picture a Santa Claus-meets-Hippie appearance – long scraggly hair, a big bushy beard – and an aversion to business suits. Bill inherited a struggling comic book company from his father in the late 1940s and, against all odds, transformed it into a satire powerhouse. In 1952 he launched MAD as a comic book, and by 1955 he’d turned it into a magazine that thumbed its nose at stuffy authority and “high-class” pretensions. Bill Gaines became the figurehead of MAD Magazine for decades, a lovable madman who insisted on doing things his own way. Why does he matter to entrepreneurs and creatives today? Because Gaines built a company culture and brand ethos that were utterly unique, wildly successful, and ridiculously fun. He proved that you don’t have to be “normal” to run a great business, in fact, a bit of craziness can be a competitive advantage.

Even if you haven’t heard of Gaines before, you’ve felt his influence. Every time you see a company with a quirky office or a startup touting its “fun culture,” think of Bill. He was doing culture before it was cool. Here are some of the key lessons I’ve learned from his example.

Lesson 1: Make Work Fun and Memorable

Bill Gaines pioneered a fun, free-spirited office culture long before anyone had heard of Silicon Valley game rooms or casual Fridays. At MAD Magazine’s New York office, the vibe was more fraternity house than corporate cubicle. One writer described it as “the frat house on Madison Avenue”, complete with practical joke props and even a set of snare drums behind an editor’s desk. Gaines fostered a family feeling among his staff: “We really do things like hug each other when we meet,” he said, noting how closely knit his team was.

Formality was actively discouraged. Neckties in the office? Forbidden! In fact, Gaines once declared that no one would get a raise if they wore a tie to work. The staff happily obliged, embracing the freedom to dress like “the biggest slobs on Madison Avenue,” as one editor fondly joked. This wasn’t just lax dress code for its own sake; Gaines understood that creatives do their best work when they’re comfortable and having fun. He redefined professionalism in his company to mean dedication to the work, not wearing a suit.

Perhaps the most famous example of Gaines’s zany leadership was his love of elaborate practical jokes. He not only encouraged pranks, he often led them. One legendary office story (recounted by longtime MAD writer Dick DeBartolo) involved Bill concocting an “evil twin” alter ego to play tricks on a new mailroom employee. Bill would show up some days as himself, warm and friendly, and on other days he’d stride in wearing a fake mustache and a scar, pretending to be “William Gaines’s evil brother” who was out to terrorize the poor newbie. The gag went on for weeks, leaving the new hire thoroughly confused, and the rest of the staff in hysterics. It was all in good fun, and Gaines was delighted by such antics. As DeBartolo recalls, Bill’s entire approach was that work should be enjoyable, even absurd, as long as the job got done well. This atmosphere of playfulness forged tight bonds among the team and made working at MAD an experience people cherished. It’s a great reminder that injecting humor and joy into your workplace isn’t unprofessional, it can actually boost creativity and morale. Bill essentially created an “office culture” before that term even existed, proving that hard work and laughter can coexist. I’ve taken that to heart in my own ventures: we take what we do seriously, but we don’t have to take ourselves too seriously.

Lesson 2: Take Your Team on Adventures (Invest in Experiences)

One of the most delightful (and extravagant) traditions Bill Gaines started was the “MAD Trips.” Starting in the 1960s, Gaines would treat his entire staff, editors, writers, artists, and often their spouses, to all-expenses-paid trips abroad, just to celebrate and bond. Yes, you read that right: the man literally took the whole “Usual Gang of Idiots” on vacation! These were no simple company picnics either. Over the years the MAD crew went everywhere from Paris to Bora Bora, from London to Japan, often on Gaines’s whimsical say-so. The very first Mad trip set the irreverent tone: in 1960, Gaines noticed the magazine had exactly one subscriber in Haiti. So naturally, he flew the staff to Haiti to personally thank that subscriber. The team showed up at the surprised kid’s house to hand-deliver a renewal card for his subscription. (The following year, Haiti gained a second MAD subscriber, and Bill jokingly proclaimed the trip a success for doubling their circulation there.)

These group vacations got more elaborate each year. What was the business rationale? Gaines believed that bringing his creative team on adventures kept them inspired and loyal – and frankly, he loved having a good time with his “MAD family.” Food and laughter were always central. In Rome, he once rented out an entire restaurant and ordered an eight-course all-pasta feast for everyone. In France, he took the staff to a quaint country inn with a cheese cart the size of a car. In Germany, they all hit a sausage and wine festival (from which it reportedly took months for one editor’s digestive system to recover). The capper: on a trip to Switzerland, Gaines put the crew up in a five-star hotel at the foot of the Matterhorn, every room with a balcony view, simply because he wanted them to experience the majestic scenery.

Crucially, these trips weren’t just frivolous perks; they built camaraderie and loyalty. The staff adored Gaines for his generosity, so much so that they developed a running joke of serenading him at dinners with a raucous original song titled “$%@# You, Bill!” (Yes, a profanity, and apparently Bill howled with laughter every time, loving the fact that his team felt free enough to roast him). The lesson for entrepreneurs is clear: invest in experiences for your team. It might not be globe-trotting vacations on a company dime in every case, but creating shared memories outside the grind of work pays off. Whether it’s an annual retreat, a team road-trip, or just a great meal together, those moments of bonding increase trust, loyalty, and creative collaboration. Gaines’s MAD trips were extreme, but they show how thinking of your team as people to be celebrated (not expenses to be minimized) can motivate everyone to do their best work. I may not be renting out Parisian bistros for my staff, but I’ve learned from Bill that once in a while it’s worth it to splurge on a meaningful team experience.

(As a side note, Bill’s penchant for adventure even led to one legendary domestic outing: it’s said that he once chartered an entire train to take the MAD staff from New York City down to Philadelphia, just because he’d read about a great restaurant there and figured, why not make it a rolling office party? That story might be equal parts truth and myth, but it totally sounds like something he would do, MAD meeting on wheels, dinner included!)

Lesson 3: Be Frugal in Small Things, Generous in Big Things

One of the more paradoxical business lessons I learned from Bill Gaines is what I’d call “worry about the pennies, not the dollars.” In other words, Bill was hyper-frugal about trivial day-to-day costs, yet remarkably lavish when it came to big-ticket spending for the team. This sounds counterintuitive, but it actually makes a lot of sense, and Gaines pulled it off with his own quirky logic.

For example, in the era before unlimited calling plans, long-distance phone calls were a particular obsession of his. Bill kept a hawk’s eye on the phone bill. If a staff member made a personal call on the company line, you bet Gaines would notice, and he would literally bill the employee for it. Former MAD editor John Ficarra recalls getting a charge-back for 32 cents because he had made a brief non-work call! No amount was too small, Bill believed in not wasting a penny on company time. He also famously refused to have expense accounts for his editors or to hire unnecessary support staff (he didn’t even employ a secretary). These habits stemmed from his upbringing and a genuine frugality, running a lean operation helped MAD survive for decades on low cover prices and without outside ads.

But here’s the flip side: when it came to rewarding the team or making work fun, no expense was spared. If the crew had to work late, Bill wouldn’t blink at ushering everyone to a fancy Manhattan restaurant and dropping hundreds of dollars to treat them all to dinner. He’d pop fine wines from his personal collection (he was a noted wine connoisseur with a 600-bottle cellar) and encourage ordering the entire menu for the table if people couldn’t decide. As Ficarra put it, Gaines’s life was governed by a love of good food and drink, and he loved sharing that with his staff. All those extravagant MAD trips we discussed? Bill personally footed a lot of those bills (at least until corporate parent companies took on some costs), simply because he valued those experiences over any short-term profit.

This “penny-wise, pound-foolish” approach was perfectly logical to Gaines. He pinched pennies on overhead (phone bills, supplies, bureaucracy) so that he had the freedom to splurge on what truly mattered: team morale, fun, and creative inspiration. There’s a powerful lesson in that for any business owner: know where to economize and where to invest. Cutting waste on trivial operational costs can give you the margin to spend generously on the things that make your company special – whether that’s employee development, memorable team activities, or delighting your customers. In my own business life, I often think of Bill when I’m agonizing over a small expense versus a big one. Would Bill Gaines worry about this? If it’s a 32-cent phone call, yes, absolutely. If it’s bringing my team together for something awesome, not at all. By focusing on the pennies, you earn the right to spend the dollars where they count.

Lesson 4: Underpromise (Deliberately) and Overdeliver

A huge part of MAD Magazine’s charm was its self-deprecating, “cheap” image, something Bill Gaines cultivated masterfully as a brand strategy. He understood that if you set low expectations, you can easily exceed them and delight your audience. In fact, one of Bill’s tongue-in-cheek mottos for the magazine was: “We must never stop reminding the reader of how little value they get for their money!”. That sounds absurd for a business to say, but it was all part of MAD’s comedic persona, and it kept readers loving the mag because it never pretended to be something it wasn’t.

How did Gaines apply this in practice? For starters, he literally made MAD look cheap on purpose. The magazine was printed on low-quality, pulp paper for many years, the kind of rough, non-glossy paper used in old comic books. Even when other publications went to slick, high-grade paper, MAD stubbornly stuck with the cheaper stock. At one point, cheap pulp paper became harder to get (as printing tech evolved), and printers offered to move MAD to better paper. Bill refused, in fact, he paid double the normal cost to keep using the crummy paper, just so MAD would retain its schlocky, low-brow feel! He wanted the magazine to look inexpensive and “disreputable”, it was part of the joke. If you paid 35¢ or 50¢ for MAD, you’d see “Cheap!” printed next to the price on the cover, and inside the magazine would gleefully insult itself and its readers’ taste. By underselling his product (in a humorous way), Gaines ensured that MAD always over-delivered on entertainment. Readers got a ton of laughs and content for a low price, and they knew the money wasn’t going into fancy paper or posh offices – it was all in good fun.

There was a business rationale here too: Keeping MAD on cheap paper and avoiding “high production values” wasn’t just aesthetic, it gave Gaines flexibility and independence. MAD famously took no outside advertising for decades, which meant it didn’t have to answer to corporate sponsors and could freely satirize any product or company. Bill partly justified the no-ads policy by noting that advertisers would demand a slicker (and more expensive) magazine, which would “have negated much of the ad revenues” anyway. Instead of nicer paper or color printing, he kept costs low and plowed the savings into paying his talent and keeping the content quality high. MAD didn’t even add color pages until the 2000s, long after Bill’s time, he was proud of its old-school black-and-white look. It all reinforced the brand: MAD was “cheap” and crass by design, so nobody expected glossy perfection, they just expected to laugh, which they did in spades.

For entrepreneurs, the takeaway is brilliantly counterintuitive: sometimes it pays to embrace being “low-budget” in certain aspects, so you can blow people away in others. Underpromise and overdeliver. Manage expectations, then surprise and delight. In my own projects, I’ve tried to channel this by not over-hyping what we offer, we keep a bit of that self-deprecating MAD spirit, understate our capabilities, and then make sure we wow customers when the time comes. Bill Gaines showed that there’s real power in humility (even tongue-in-cheek humility) as a business strategy. Plus, let’s be honest, it’s a lot more fun to joke about your product’s flaws than to pretend you’re perfect.

Lesson 5: Stick to What Works (Technology Isn’t Everything)

Bill Gaines was, in many ways, a traditionalist when it came to his business operations. This is the man who once said he thought writing on old typewriters somehow came out funnier than writing on computers, and he acted on that belief. While the world raced toward new technology, Gaines held MAD Magazine to a delightfully stubborn, analog pace. For example, he didn’t computerize his subscriber and business records until well into the 1980s – incredibly late for a publisher. As late as 1985, observers noted that Bill still kept circulation figures in hand-penciled ledgers rather than on a computer. When MAD finally did a special video-disc edition in the early ’80s, Gaines agreed only grudgingly, quipping, “Those people who don’t read, we’ll give ’em TV”. That quote perfectly captures his grumpy resistance to fads. He loved print, corny puns, and physical paper, and he wasn’t going to change just to chase the latest shiny tech.

In the office, Gaines famously eschewed fancy equipment. The MAD editorial crew stuck to typewriters and drawing boards for as long as possible. Bill felt no need for word processors or digital anything if the old methods were working. It became part of MAD’s ethos: delightfully behind the times. In fact, when MAD finally switched from typewriters to computers (after Bill’s era), it was a big internal culture shock, as if some of the magic was tied to those clacking IBM Selectric typewriters.

Now, I’m not saying one shouldn’t adopt useful technology (and I doubt Bill truly thought typewriters were magically funnier, it was probably half-joking). But the lesson here is about authenticity and focus. Gaines knew what made MAD great, the creativity of his staff and the edgy humor, and he didn’t let “latest tech” distract from that. He wasn’t going to chase trends at the expense of the product’s soul. In an age where entrepreneurs often feel pressure to constantly upgrade, get on every new platform, use every new tool, Bill’s approach reminds me to ask: Will this actually make our end result better? If the answer is no, it’s okay to stick with what works for you. Technology is awesome, but it’s not a panacea for every business. Sometimes maintaining a human touch or a tried-and-true process can be your differentiator. Bill Gaines took pride in MAD being a bit old-fashioned (he once joked that moving MAD from NYC to LA would kill him, and indeed, the magazine only moved years after his death, and he likely would have hated it). In my own work, I take this as permission to not jump on every bandwagon. If the old way is effective and aligns with your values, you don’t always need to reinvent the wheel. As Bill showed, a little stubbornness in defense of your creative vision can be a very good thing.

Final Thoughts: Wisdom from a MADman

Writing about Bill Gaines, I can’t help but smile. His life was full of hilarious contradictions that somehow gelled into a genius way of doing business. He was a penny-pincher and a big spender; a traditionalist and a rebel; a boss and a big kid at heart. Under his guidance, a magazine that prided itself on being “cheap” became an American icon and cultural institution. And while he never framed them as “business lessons,” the things Bill did naturally have taught me and countless others so much about leadership and creativity:

• Take care of your people, even if it means going a bit over-the-top, and they’ll take care of your business.

• Make it fun, make it memorable. A team that laughs together can create amazing things together.

• Don’t waste money on things that don’t matter, but be generous about the things that do.

• Stay true to your identity. Fancy isn’t always better, being authentic and a little “rough around the edges” can build a loyal audience.

• Embrace the madness. Sometimes the best business move is to do something crazy (like a fake mustache prank or a surprise trip) that conventional MBA logic would never endorse.

Bill Gaines passed away in 1992, but the legacy of his leadership style lives on, not just in the pages of MAD, but in every playful, irreverent workplace and every brand that winks at its customers. On a personal note, I often find myself channeling a bit of Bill’s MAD spirit in my own entrepreneurial journey. Along with my father’s guidance, Bill’s example reminds me that work can and should have an element of joy and mischief. It’s possible to be dead serious about quality while also never taking yourself too seriously. In business, that balance can be magic.

So here’s to William M. Gaines – the MADman who taught us that business, like a good joke, is best when it’s shared, a little unexpected, and leaves everyone smiling. What, me worry? Not when I’ve learned from the best.