Problem Solvers

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...

Jen O'Neal and Jeff Manheimer launched a social network called Tripping.com , which quickly became a frustrating puzzle: It was very popular, but impossible to monetize. What does an entrepreneur do when they've hit upon something people love, but that they won't pay for? In this episode, we learn what the duo did next—abandoning part of their vision, but building a booming business in the process...

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...

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.

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...

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...

You want customers to love your product, of course. But what happens when they don’t? The simple answer: You have to make a change -- and it won’t be easy. Today we follow the story of Grayl, a company that created a groundbreaking bottle that filters water. When it first hit the market, sales sagged and customers were confused. So Grayl spent three years better understanding its ideal customer an...

How do you scale when your business depends on it? Chieh Huang of Boxed knows this well; his company is like an online wholesale club (with no membership fees), and in four years, he took it from a garage to $150 million in funding and its own custom-built warehouse. In doing so, he survived one of the hardest kinds of uphill battles in business. Some business ideas only work at a large scale, but...

Every company wants to increase user engagement. But for a company like Meet Group, it was a life-or-death need. It runs four free dating apps (Meet Me, Skout, Tagged, and hi5), and relies largely on advertising -- which means when user engagement was down, ad dollars were down too. To fix this, cofounder Catherine Cook Connelly radically rethought how users engage in the apps. Now revenue is up,...

HelloFresh made one counterintuitive change in its business, and it sparked an immediate boost in sales. The result should be a lesson to all entrepreneurs: In business, simple things matter. Simple changes matter too. In this episode, the head of HelloFresh’s U.S. business reveals how he runs experiments in his business, how he honed in on the right change -- and why he’ll keep making little chan...

It can be hard convincing others to work with you, especially if your company is new. And yet, you need them: They’re your future suppliers, contractors, partners, and sponsors, which means you must find some way to prove that you’re worth working with. That’s what Andy Sitt faced when trying to build an Asian stock photo company called Inmagine -- and solving it led him on an insane journey. Now...

Hanson Grant had built a hit product called Think Board, and what seemed like a world-class customer support team. But when his product started getting terrible reviews on Amazon, he scrambled to figure out what was wrong -- and discovered the problem was hiding in plain sight. Sometimes, the thing you think is solving a problem is actually creating one. In this episode, Grant explains how a disas...

How do you raise prices? It’s not easy, as the cofounders of Motto can attest. For more than a decade, they’ve been raising prices -- while evolving from a little design shop to a full-scale, high-end branding agency. Along the way, they were forced to reconsider exactly what work they do, how they structure their relationships with clients, and even what kind of company they run. Because pricing...

Many entrepreneurs struggle with how to hire the right people. But they don’t always think about when to hire those people. That can lead to disaster, as Zapier cofounder and CEO Wade Foster knows well. He used to follow a philosophy he calls “don’t hire ‘til it hurts,” until his company grew so fast that he was severely understaffed. That forced him to develop a new staffing system, one that ensu...