Problem Solvers

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...

How can a company survive a crisis so big, its very future is in doubt? Draft Kings knows the answer. It was a startup on the rise, making millions by allowing fans of fantasy sports to bet online -- but in 2015, a huge lawsuit and skeptical legislators created havoc. In this episode, CEO Jason Robins speaks frankly about how he navigated the years-long storm, stayed focused, and survived, and is...

What happens when customers don’t share your vision? It can be an emotional blow. Here you poured your heart into a product, only to find that customers want something different. Shira Berk faced this problem with her gluten-free cookie company, Goodie Girl Cookies. Taste tests were positive but sales were stagnant, and Burke realized it was because her personal branding touches were confusing con...

How do you turn a great idea into a great business? It’s an infinitely complex question. You have to build an infrastructure around that idea -- one that amplifies it and makes it compelling enough for someone to pay for. On this episode, we learn how Brian Kelly did just that. He turned a grueling side hustle into The Points Guy, which is now arguably the most well-recognized and influential site...

How can you scale yourself? It’s something every successful entrepreneur needs to figure out. At some point, your company will become so big that you can’t be in the weeds the way you once were. If you try, you’ll create a bottleneck and harm your company. So, what’s the solution? This week we learn how Adam Tischauer, founder of a company that hosts sleepaway camps for adults called Camp No Couns...

What’s it like when your company goes viral? Take it from Kristen Tomlan, the founder and CEO of a viral cookie dough company called Do ("Dough") "It's terrifying." And exhausting. And it exacerbated every weakness in her business, including staffing, supply and production. We learn how she fixed it, and harnessed the kind of huge opportunity that may have sunk others.

You did your homework. You lined up the right investors. You hired the right talent, created a product that everyone in your industry thought was just going to totally wow people and then you launch... and realize you severely miscalculated. It happens to a lot of businesses, and it happened to Scott Ruddman of GLORY Sports International. In this episode, we explore how he tore down his old plans...

Jaron Gilinsky created Storyhunter, a platform that connects media companies and brands to freelance video producers and journalists in 180 countries. But to succeed, he had to overcome two major problems: First, his original business model was failing him. And then, once he created a great way to connect those media companies and video producers, he had to become so invaluable that they wouldn't...