How I Built This

Colin Angle didn’t start out trying to clean people’s floors. He started out trying to shape the future–with robots. In the early days of iRobot, there was no business model. No steady funding. No clear customer. Just a belief that robotic technology would one day make the world a better place.

Today’s callers: Rebecca from Australia wants to make her small-batch spirits stand out in a crowded market. Then, Sri from England wonders how to balance commercial and humanitarian interests for her heated mats.

A lot of founders spend their lives chasing one big idea. Antonio Swad had two. The first? Migrating chicken wings from the Happy Hour buffet to the center of the plate. The second? Building a pizza business that catered to a very specific demographic: Latinos.

Today’s callers: Michelle from California assesses the trade offs of accepting outside investment to scale her organic granola brand. Then, Gloria from Connecticut wonders how to overcome stigma and get more people talking about her pelvic floor therapy device.

Back in the early days of ecommerce, Marc Lore took a classic retail loss leader–diapers– and turned it into a DTC giant– Diapers.com. It did so well that it attracted the attention of Amazon, which slashed prices on its own diapers until Marc was forced to sell them his business.

Serial entrepreneur Marcia Kilgore — founder of brands like Beauty Pie and Soap & Glory — joins Guy on the Advice Line, where they answer questions from three early-stage founders managing uncertainty and risk.

For decades, a dozen eggs was just… a dozen eggs. No story. No real branding. No reason to care who produced them. Then Matt O’Hayer came along and asked a question almost nobody in America was asking: what if store-bought eggs could be different?

In today’s special episode, Guy and four former show guests talk with callers about how they can prove the value of their products—and themselves. First, Meagan from Vermont questions whether an experiential pop-up concept for her reusable gift wrap and bags is worth the effort.

Aaron Krause did not set out to reinvent the kitchen sponge. He was a car detailer, building buffing pads and the machines that made them. To clean his greasy hands, he made a makeshift hand scrubber out of extra-rough foam, and it worked so well he decided to sell it. But nobody wanted it.

Today’s callers: Heather from Ontario talks through a DTC strategy for her retail pain relief tape and patches. Then Nawal in Michigan considers a rebrand for her uniforms designed for Muslim students.

Bobo’s: Beryl Stafford. A Single Mom Turns a Baking Project into a $100M Business At 40, Beryl Stafford’s life cracked open. Her marriage ended, she hadn’t worked in years, and she had two daughters to raise. She needed income—fast. So she did the only thing that felt real: she baked.

Today’s callers: Jane in Minnesota wants to scale her artful pants brand while staying true to her locally-made mission. Then Melissa in New Mexico wonders how to respond to diminishing returns on digital advertising for her grief care packages.

Kettle Chips: Cameron Healy. The Wild Bet That Made a Brand Most founders expand the “right” way: local → regional → national → international. Cameron Healy totally skipped the “national” part.

Today’s callers: Jess from Washington seeks counsel on structuring a collaboration between her sympathy cards company and a pet products brand. Then, Caroline from Colorado wonders if she should build an in-house production team or outsource manufacturing for her decorative garland company.

Most entrepreneurs think the hardest part of building a company is the product. For Jim McKelvey — co-founder of Square — the hardest part was the system around the product.

Today’s callers: Yadi from New York thinks through an expansion strategy for her college campus-based empanada business. Then, Zachary from New York looks for ways to break into big retailers with his fresh-made frozen pies.

Before Spinbrush became the top selling toothbrush in the U.S—and before Procter & Gamble paid $475M for it—John Osher was a teenager selling earrings for $4.99.

Today’s callers: Mia from Germany wants to know how to balance her pottery business between an online shop and a YouTube channel. Then, Jen from Connecticut is looking for ways to reach more families with her print magazine for tweens and teens.

Netflix shouldn’t have survived. In 1997, Blockbuster owned home entertainment—9,000 stores, a business fueled by late fees, and a brand that felt untouchable. Netflix was a scrappy DVD-by-mail experiment that almost sold itself off to stay alive. So how did Netflix win?

Plus, Jon’s take on why now is a good time to start a business — in spite of market uncertainty. Today’s callers: Dan from Washington considers new offerings beyond his core loose leaf yerba mate product.

In the late 2000s, two French mountain athletes set out to build a running shoe that captured the feeling of flying. Jean-Luc Diard and Nicolas “Nico” Mermoud had spent decades inside the innovation engine at Salomon—where product was obsession.

Plus, Mark on his most challenging venture yet: revolutionizing the prescription drug market in America. First we meet Lucy from Washington DC, considering an opportunity to bring her upside-down peanut butter brand into a big box retailer.

A bright blue guitar covered in orange koi fish vanished from a museum display … and Swifties immediately knew what it meant. That distinctive guitar—the one Taylor Swift used to record Speak Now—had been a gift. Hand crafted, by the founders of Taylor Guitars.

Plus, how candor has been a more effective press strategy than talking points for (the literal) Mrs. Meyers. First we meet Allison in California, seeking marketing ideas for her novel wig designs which aren’t done justice by photos alone.

Before Gymboree became a cultural icon in the 80s and 90s, it was just one lonely new mom trying to find connection. Joan Barnes started hosting weekly playgroups for parents… and demand exploded. What began as a diversion became a business. Then a franchise.

Fashion legend Norma Kamali discusses five decades of innovation in fashion, from the sleeping bag coat to swimwear design. Covers how she maintained creative independence in an industry driven by conformity.

Airbnb co-founder Joe Gebbia answers questions from early-stage founders about design thinking, building trust in marketplace businesses, and why his new venture Samara applies Airbnb's lessons to housing.

Hinge founder Justin McLeod tells the story of building and rebuilding the dating app. Discusses pivoting from a swiping app to a relationship-focused platform, his personal love story that inspired the rebrand, and designing for meaningful connections.

Ben Francis — 19-year-old pizza delivery driver — screen-printed gym clothes in his parents' garage. Pioneered influencer marketing by cold-messaging fitness YouTubers. Stepped down as CEO when the company outgrew him, studied leadership, then returned.

Hamdi Ulukaya returns to update his Chobani story: from buying an abandoned yogurt factory for $700K to building a multi-billion-dollar brand. Discusses his employee ownership model, refugee hiring program, and why business should be a force for good.

Mike Cessario tells the origin story of Liquid Death, the canned water brand with punk rock marketing. Discusses asking what is the dumbest possible idea? as a creative strategy, and how contrarian branding built a billion-dollar water company.

José Andrés built a culinary empire, then pivoted to disaster relief. After Hurricane Maria devastated Puerto Rico, he served 3.7 million meals while FEMA was still filing paperwork. World Central Kitchen now deploys to every major disaster globally.

Melanie Perkins — 19 years old, from Perth, Australia — pitched 100+ Silicon Valley investors and was rejected by every one. She taught design software to university students, noticed how needlessly complex it was, and built Canva to fix it. Now worth $40B+.

Whitney Wolfe Herd left Tinder amid a sexual harassment lawsuit and public humiliation. Instead of retreating, she built Bumble — a dating app where women make the first move. She became the youngest woman to take a company public.

Tobias Lütke — a German snowboard enthusiast who moved to Canada — tried to sell snowboards online and found every platform terrible. So he built his own. That tool became Shopify. He deliberately stayed in Ottawa instead of moving to Silicon Valley.

Jamie Kern Lima — former TV anchor with rosacea — was told her skin condition was a liability. She made it her brand's identity, going on QVC without makeup to show the before/after. L'Oréal acquired IT Cosmetics for $1.2B.

Katrina Lake started a personal styling service from her apartment at Harvard Business School, personally packing boxes. VCs told her fashion and data don't mix. She became the youngest woman to take a company public.

Two brothers from rural Ireland — Patrick dropped out of MIT at 19, John out of Harvard — built Stripe because accepting payments online was absurdly difficult. Seven lines of code to integrate. Cold-emailed potential customers as teenagers.

James Dyson built 5,127 prototypes over 15 years to perfect the bagless vacuum. Every manufacturer rejected him. He mortgaged his house, nearly went bankrupt, and was told repeatedly that bags were fine. The 5,127th prototype worked.

Yvon Chouinard never wanted to be a businessman. He started forging climbing pitons by hand, accidentally built Patagonia, and then gave the entire company away to fight climate change. The reluctant billionaire who rejected the hedonic treadmill of growth.

Howard Schultz grew up in Brooklyn projects watching his father — a delivery driver — get injured on the job with no health insurance, no workers' comp, no dignity. He built Starbucks into a company that gave part-time workers health insurance because he remembered what it felt like to have nothing.

Sara Blakely turned $5,000 into Spanx — a billion-dollar company — with zero fashion experience. Sold fax machines door-to-door for 7 years. Pitched Neiman Marcus by trying the product on in the bathroom. Her father's nightly question: 'What did you fail at today?'

John Mackey — college dropout, counterculture idealist — opened a small natural foods store in Austin in 1980. A flood nearly destroyed it in year one. The community and employees rebuilt it without being asked. He pioneered 'conscious capitalism.'

Herb Kelleher — a corporate lawyer — sketched a low-cost airline on a cocktail napkin. Competitors sued to prevent Southwest from ever flying. He spent years in court before earning a dollar. Then built the most profitable airline in history through employee-first culture.

Two RISD grads who couldn't pay rent put air mattresses on their floor. They sold novelty cereal (Obama O's, Cap'n McCains) to fund the company. Rejected by every investor. 'Do things that don't scale' — Chesky personally photographed every listing.