Problem Solvers

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 those businsses must start small like everyone else -- and then endure a long, gaping middle point when they’re running their business at a size that inherently doesn’t work. Huang shares how he got over the hump.

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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, users are using the apps for longer, and matches are being made with... live video!?

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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 changes that can lead to big results.

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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 Inmagine is a powerhouse, with 72 million images and 40 offices around the world.

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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 disaster for the company forced him to rethink everything.

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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 isn’t just about a number. It’s about your value, what you’re really worth, and who you want to work with.

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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 ensures his staff grows at the same pace his company does.

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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 now thriving once again.

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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 consumers. So she made big, hard changes -- and sales grew to more than $3 million. We learn how she did it.

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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 in the credit card world. It time, grit, and a lot of failure -- but that’s the real a recipe for success.

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