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Andy Dunn hated shopping.

So did millions of men across the country.

Instead of ignoring the problem, he built a solution — and a story — that turned into a $100M brand.

All centered on one simple idea: finding better-fitting pants without ever stepping inside a mall.

In today’s newsletter, I share Andy’s form-fitting story as well as:

• 3 storytelling lessons from Andy you can apply to your brand

• Why 88% of people trust referrals more than ads

• A video where Andy tells how brand experts couldn’t build an online brand (and he did it anyway)

Enjoy this pants-wearing ninjas’ trip into the online retail jungle…LG

Founder Tip:

After working in consulting and private equity, Andy Dunn left Stanford’s MBA program with big plans to launch an online personalized magazine. He believed the web offered a massive opportunity to build a service-based, customer-first brand.

But that plan shifted when he discovered his B-school housemate, Brian Spaly, shared a deep, almost existential, hatred for shopping.

For Andy, walking into a retail store felt like his soul was being sucked out of his body.

It was time-consuming, frustrating, and the pants never fit right off the rack. The only fix? Shell out more cash and time for tailoring.

For Brian, finding pants that fit was a losing battle. As a former football player with an athletic build, sizing up meant suffering through a saggy, diaper-butt fit, and nothing off the rack ever worked.

So he taught himself how to sew using his girlfriend’s sewing machine, dismantling store-bought pants for himself and soon doing it for classmates.

The idea started brewing: what if they could create pants that fit off the rack? No more expensive tailoring and no more wasted Saturdays wandering department stores.

Andy and Brian envisioned marrying Brian’s craftsmanship with Andy’s ambition to build a web-based, customer-first brand. Andy called it "Polo meets Zappos" — timeless style combined with revolutionary service, all without ever stepping inside a mall.

That summer, still on the Stanford campus, they pooled their savings and made 60 prototype pairs — lightweight corduroy pants they named "Turks," perfect for California weather.

Without a store to sell from, they got scrappy.

They sold the pants out of car trunks, duffle bags at weddings, and even from a friend’s backyard tent (after the fabric overflow was banned from the house by a wife juggling four kids).

Wherever they went, the reaction was electric: guys loved the fit, the feel, and maybe most of all, not needing a tailor.

Fueled by word-of-mouth and early customers who couldn’t stop raving, Andy and Brian doubled down. They focused on one thing, selling better pants, and started raising capital from classmates, professors, customers, and anyone else who believed in the vision.

The early success gave them the confidence to dream bigger.

They packed up 400 pairs of pants, moved to New York City, and turned Andy’s apartment into their warehouse. Shelves lined the walls, inventory hung from makeshift racks, and a crazy, simple website became their storefront.

They started selling to friends under the name Bonobos, and sold the first 200 pants almost immediately.

What started as trunk sales on campus was quickly growing into something much bigger.

For Andy and Brian, the internet wasn’t just a sales channel — it was how they told their story and built their brand through word of mouth.

The site allowed them to connect with customers, explain the perfect fit, and recreate the in-store shopping experience without ever opening a physical store.

They made the website feel like walking into a great store by using sharp product photography, witty descriptions, and a site built to communicate fit, style, and personality.

Instead of flashy ads, they told the Bonobos story through every detail:

They pioneered a direct-to-consumer model before it was cool: free shipping both ways, lifetime returns, and a gold-standard customer service team called "Ninjas," inspired by Zappos.

The Ninjas didn’t just process orders, they built real relationships.

Bonobos wasn’t just selling pants.

They were selling a faster, frictionless, even fun way to shop.

One year later, they had sold 12,000 pairs without spending a single dollar on marketing.

What started as an idea between two friends became the largest apparel brand ever launched on the web.

Bonobos grew to include ten storefronts, won accolades like “One of America’s Hottest Brands” by Advertising Age and “Best Men’s Pants” by New York Magazine, and eventually scaled to $100 million in annual revenue.

In 2017, Walmart acquired Bonobos for $310 million.

Storytelling Lessons:

Andy Dunn didn’t just build a brand. He built a movement by deeply understanding his customer, solving real problems, and using storytelling as his distribution engine.

Here are 3 storytelling lessons you can apply to your own business:

1. Meet Customers Where They Are (and Make It Personal)

   Andy and Brian turned the internet into their storefront using witty product descriptions, smart photography, and a customer-first website to tell the Bonobos story directly to the people who needed it.

   
   If you run a food brand, treat your website and packaging like a conversation, not a transaction. Show how your product solves a mealtime problem. Use your site and labels to make shoppers feel like you “get” their busy lives, not just selling food, but making life better.
   

2. Lead with Passionate Conviction

   Andy didn’t fake enthusiasm, he lived it. Even when he lacked fashion credibility early on, he spent weekends studying retail, learning the craft, and showing up with authentic passion for solving the "pants problem" for men. His energy became infectious to customers, investors, and team members.

   
   If you’re building a tech company, show your passion in public. Don’t just promote features; share why you believe your solution matters. Talk about the bigger mission behind your product, and let your conviction turn early users into evangelists who want to build the future with you.

3. Solve the Real Pain Point (And Tell That Story Clearly)

   Bonobos succeeded because they didn’t just make another pair of pants — they solved the real, frustrating experience men hated: bad fit and painful shopping. They stayed laser-focused on that story, making it clear and consistent at every customer touchpoint.
   

   If you’re a photographer, lead your messaging with the problems you solve for clients, not just your portfolio. Instead of only showing beautiful photos, talk about how you make clients feel comfortable, capture real moments effortlessly, and deliver images they’ll actually love.

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Fun Fact:

Bonobos didn’t rely on ads to grow — they relied on customers telling other customers. And there’s science behind why it worked. According to Nielsen’s 2021 Trust in Advertising Study, 88% of global respondents trust recommendations from people they know more than any other form of advertising.

By focusing on a great product, a great story, and a great customer experience, Bonobos turned early buyers into evangelists who skyrocketed sales in those early years.

Video to Watch:

In this early Bloomberg interview, “Andy Dunn Discusses Business and Product Strategy,” you’ll get a great look at how Andy connected with male shoppers in a whole new way, growing Bonobos from a scrappy startup into a breakout success.

Watch as he shares how he found a real customer problem, built a better product, and launched Bonobos when everyone told him a web-only brand couldn’t work.

Storytelling for Entrepreneurs Issue #029 - The $310M Brand That Began in a Car Trunk...

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