Problem Solvers

People may like to shop for cars online, but they still want to test drive them in real life before buying. So when the online car sales company Shift launched, it created a system its founders were sure would win customers over: They hired “car enthusiasts” -- guys just really passionate about cars -- to drive a car to a customer so they could test drive it together. The car enthusiasts were a hi...

A company's name is one of (if not the) biggest early decisions a company founder will make -- and they often get it wrong. Google was first called BackRub, Best Buy was Sound of Music, eBay was AuctionWeb, and Policygenius was KnowItOwl. In this episode, Policygenius's founder walks us through the rigorous process she went through to scrap a confusing name and create one that led to success. Lear...

Sean Dowdell loved tattoos, but he hated tattoo parlors. They were dirty, uninviting, downmarket, unprofessional and often sexist. So when he set aside his music career to start his own tattoo parlor, he needed to find a way to make a traditionally lowbrow product appeal to a high-end, but still edgy, audience. A decade later, he’s now opening glitzy tattoo shops all over the world. Here’s how he...

What happens when your customers are willing to use your product, but they're not willing to pay for it? Answer: Your business model may be wrong. That's what Ilir Sela learned after launching Slice, a company that helps local pizzerias sell online. He found plenty of early customers, but they weren't paying their invoices. As he dug deeper, he realized the problem wasn't them -- it was him. And h...

Patrick Llewellyn discovered that his design company, 99designs, was only fulfilling some of his customers' needs. He wanted to fill more, so he created a spinoff brand called Swiftly. But in doing so, he created a major problem for himself: He was stretching his resources too thin, and confusing customers about which brand they should use. In the end, he discovered the Curse of the Problem Solver...

When Daniel McCarthy cofounded the music licensing company Musicbed, he had a big idea: "I don’t want customers to just think about Musicbed when they think about music licensing. I want them to think about Musicbed when they’re trying to get inspired." Accomplishing that would require a lot of experimentation, spending money with no sure ROI, and launching (and closing) a magazine. In this episod...

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Every entrepreneur’s journey starts with a big problem. That first hurdle—and hopefully, that first solution. Small and sometimes simple as it may be, this first moment contains so much ingenuity and inspiration, and captures just how resourceful entrepreneurs must be to continue along their path. Today, we’re telling three mini-stories of first-time challenges: how the creator of the Butterie but...

Glenn Kelman thought of himself as a software guy. Then he became CEO of a real estate company called Redfin, but insisted on seeing it as a software company. Confusion reigned. Cultures clashed. For Glenn, it would come to highlight an often-unspoken business challenge: Entrepreneurship means exploring unknown paths, sometimes leading entrepreneurs to a very different place from where they starte...

How do you find your first customers? It’s a question first-time founders are often flummoxed by. But Keith Krach has developed a tried-and-true strategy—starting during his days at Ariba (which sold for billions), and extending into his current time as chairman of Docusign. In this special live edition of Problem Solvers, taped at Entrepreneur Live in Los Angeles, Keith explains how to turn a com...

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From the outside, Cogent Entertainment Marketing looked like a success: It got early into the influencer marketing game, quickly signing big clients and making good money. And because profits were high, founder Mark Zablow was afraid to make any changes—even as major leadership problems in his company began wreaking havoc. In this episode, we explore how Mark finally fixed his culture (while still...

What happens when you’re trying to sell to consumers, but your best customers are actually other businesses? Furniture-maker Poppin’s answer: It radically transformed itself to meet this new customer. That meant changing its brand voice, marketing, products, and supply chain. In this episode, we explore how and why it made the switch—and became the go-to furniture maker for Facebook, Snapchat, Goo...

Beck Besecker believes in transparency. So much so, that he calls Marxent, “aggressively transparent.” That means everyone can talk to everyone else. Everyone has a voice. Everyone has access to management. Most important, everyone is trusted. There’s an assumption that the employees of Marxent are professional, responsible, mature adults, and thus they’re completely capable of taking bad news and...

Chrissy Monaco was basically raised at Monaco Ford, her dad’s car dealership. Then in January of 2017, she took over as co-owner and new boss—now in charge of men she’d known all her life, some of whom weren’t immediately comfortable with it. She knew her task: New leaders have limited time to set a company’s culture and get people on board with their vision, before doing so becomes far harder. In...

Entrepreneurs love to say yes—to new ideas, to new opportunities, and to new markets. But yes can be dangerous: The wrong yes will compound itself, stretching a company thin and clouding its sense of purpose. Hamilton Powell learned this the hard way: As he built his watch company Crown & Caliber, he said yes so often that he was soon working 100-hour weeks and burning out his employees. Then he h...

Tami Halton Pardee started out working in Hollywood—an industry known for crushing hours and sociopathic behavior. Then she left to work in real estate in Los Angeles—another industry known for crushing hours and sociopathic behavior. But instead of going with the flow, she decided she’d work differently, structuring her company to allow her employees a better work-life balance, and being kind to...

Every entrepreneur wants a loyal fanbase, a group of repeat customers who will evangelize their favorite brand. But superfans come with challenges: They love a company exactly the way it is, and they do not want it to change. That was a problem for Tough Mudder, whose obstacle course races were attracting primarily young, fit men. To grow as a business, it would need to attract different kinds of...

In its first four years, Tyson Lawrence’s logistics company reached $5 million in sales. “Everything I touched turned to gold,” he says. But then the golden touch disappeared, and his growth stalled. Why? When he looked into it, he discovered a disaster in the making: His biggest client, a national retailer that helped his company grow so fast, had become its biggest problem. And to help his compa...

Sam Sisakhti had a great idea for a company, and early on it seemed like others agreed. He got funded on his very first pitch. But when that funding fell apart, and Sam embarked on a punishing year and a half of brutal rejections, he learned invaluable lessons about himself, his business, and the nature of entrepreneurship, and he turned his failure into a big success. Learn more about your ad cho...

For many entrepreneurs, the stretch between Halloween and New Year’s is when teams get stressed, systems get strained, and even the smallest inefficiencies amplify into crises. But if a company builds itself well enough to survive into January, it’ll be in great fighting shape for the rest of the year. That’s what happened to popular New York-based cupcake company Baked By Melissa, whose disastrou...

Here’s a thought that’s going to make you crazy: Somewhere in your business, in a place you’ve completely overlooked, there’s a major opportunity you’re passing up. On this episode, we explore how it happened to Quizlet CEO Matthew Glotzbach. His company makes a hugely popular study platform for students, and yet for a while, Glotzbach was ignoring an opportunity to triple his advertising revenue....

A successful Kickstarter campaign is exciting, but it can also be a curse. New entrepreneurs routinely miscalculate how much money they need to fulfill orders, and get drowned in unexpected costs. How can someone survive that? We follow the story of Ryan Lupberger, founder of an eco-friendly laundry detergent called Cleancult, who could have gone broke after his Kickstarter success -- but then mad...

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Here’s the most exciting question to ask today: “Why is this thing sold this way?” The answer will reveal all sorts of business opportunities, and startups who asked this question have gone on to disrupt everything from razors to the mattress industry. But the path to success isn’t simple; a startup must literally reinvent an industry. How? In this episode, we follow the path of Burrow, a company...