Problem Solvers

Numbers can be deceptive: Just because you have more customers, locations, or dollars coming in, that doesn’t necessarily mean your brand is growing strong and stable. That’s what Jill Salzman discovered with her company The Founding Moms, a collective of meet-ups and resources for mom entrepreneurs. At first, she wanted to be in every city as fast as possible. So she expanded rapidly -- and altho...

It’s become a truism of startup life: To grow a company, first go out and get investors. But is that true? Does every company need investment? Not really. That’s what Eric and Sasha of the men’s retailer Buck Mason discovered, after they went out to raise cash and were rejected by every investor they met. It forced them to step back and rethink who they are as a company, and how they can thrive. T...

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...

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...

What’s it like when your company goes viral? Take it from Kristen Tomlin, the founder and CEO of a viral cookie dough company called DŌ: “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.

There are a lot of Uber-like startups out there—companies that connect customers with some set of service providers, such as cleaners, lawn care pros, or, in the case of Storyhunter, companies looking for video freelancers. But these companies all face the same danger: They're at risk of disintermediation, or being cut out of the deal. (After all, if you're a consumer and find a great cleaner thro...

IAC CEO Joey Levin told Problem Solvers host Jason Feifer that everyone -- everyone, at every level! -- feels like they're making things up as they go. On this episode, Jason dives deeper into that idea. At times when you feel intimidated, or worry you're not up to the task, or feel at a loss for the right answer, let this be your guide: It’s knowing that in actuality, nobody inherently belongs. N...

Lauren Berger was like many solopreneurs: She'd built a one-person business called Intern Queen, and it made her a good amount of money. But it wasn't scaleable. She could only do so much. In this episode, we learn how Lauren ultimately transformed her one-woman shop into a company that can scale... and in the process, discovered a new line of work that now makes up 90% of her revenue.

When Maynard Webb became COO of eBay, he had a huge problem on his hands: The company had just acquired PayPal, and he had to not just fix what had become a dysfunctional culture at eBay, but now had to also integrate another company and create a shared mission for everyone. His first attempt to fix this totally failed. That's when Maynard learned the true secret of creating a great company cultur...

In 2015, Carrie Sheffield founded a live-streaming news service called BOLD. Two years later, a pair of gigantic public media companies announced that they, too, would be launching a live-streaming news service called BOLD. In this episode, we follow what happened next... and turn to an IP lawyer to help us make sense of it all.

When the home security company SimpliSafe launched, it marketed itself entirely towards renters. After all, they were an underserved marketplace—no other home security system was made for people who rent apartments. But SimpliSafe wasn't growing as fast as its founders expected, so it dug into its customer data and discovered something surprising: Half its customers were home-owners, the people it...

In 2014, Home Depot was hacked—and 56 million credit cards were compromised. It was one of the largest data breaches to befall a major corporation. Then-CEO Frank Blake wanted to preserve Home Depot's relationship with its customers, so he came up with a plan: Unlike other companies in this situation, who hid the breaches from their customers for months or even years, he was going to be radically...

What happens when you release a new product, and none of your customers seem to care? That's what happened to David Politis. He started BetterCloud in 2011, and its simple product was a big hit. But David thought he could go bigger, creating a product that would help companies was a wide variety of their cloud computing needs. So he poured a lot of money and time into building this new product, la...

Andy Monfried's company Lotame was thriving, but he saw trouble on the horizon: His industry was changing. Lotame was a major player in the complicated world of digital advertising, and although there was plenty of growth still to be had and plenty of money still to be made, Andy knew that his company's long-term future was going to be rocky. So he made a difficult, gut-wrenching decision. Rather...

Every entrepreneur struggles to manage their time, and Gen. Stanley McChrystal (Ret.) knows that challenge especially well. He previously commanded U.S. forces in Afghanistan, and now oversees a 90-person consultancy called the McChrystal Group. How does a guy this busy keep on schedule? In this episode, we learn how McChrystal uses a calendar with the level of rigor only a former military general...

When Joshua Tetrick founded his plant-based food company JUST, his goal was to disrupt the entire food industry—and to do that, he decided, he'd hire industry outsiders. He didn't want people with lots of food-industry experience, who'd just carry all the marketplace's old assumptions with them! But then his company began having massive problems, and losing massive amounts of money. And Joshua cam...

In this special episode, host Jason Feifer gets personal. Whenever he tells people that he wrote a novel (Mr. Nice Guy) with his wife, their reaction is always the same: "You're still married!?" To celebrate the release of the book, Jason and his wife Jennifer Miller talk about how they built a healthy working relationship while also strengthening their marriage, and what it takes for everyone els...

When Ari and Gavi started Indiewalls, a company that wanted to manage sales of art on cafe walls, they hadn't fully thought through just how difficult it would be. But that turned out to be for the better: Because they were willing to dive into this crazy industry, they were able to meet people who wanted art, understand the marketplace, and then transform into an entirely different company. This...

Millions of people know Nicole Arbour as a comedian, actor, model, YouTube celebrity, and Instagram influencer—but until recently, she was afraid to reveal another side to her: Years ago, a car accident had left her with chronic, debilitating pain. She worried that if people knew, they wouldn’t want to work with her. Or, she feared, she’d become defined by her disability. But now she’s talking. Th...

When Jean Thompson stepped in to save Seattle Chocolate Company, she slammed the gas on a rapid expansion -- selling into stores nationwide, and locking in enormous private-label businesses. It seemed like the solution... until her company was rocked by financial instability, and she discovered that not all sales are good sales. In this episode, we understand what was wrong with Thompson's expansi...

When you think of Malcolm Gladwell, you surely think of something: an author, a journalist, a podcaster, a speaker. But Gladwell doesn't. "Self-conceptions are dangerously limiting," he says. If he defines himself as any one thing, he believes, he'll shut out opportunities he didn't even know existed. In this conversation with Gladwell, he explains how he approaches problem solving -- by being a h...

Sometimes, the simplest ideas turn out to be the hardest. That was the case at Dunkin' Donuts, where the company wanted to eliminate its Styrofoam cups and replace them with something more environmentally friendly. They thought it would be easy -- but the change took 10 years, countless prototyes, meetings with competitors, and a deep study of how people hold cups. This is the inside story of that...

If you've watched a commercial or movie recently, you've likely seen Score a Score's work: It connects the biggest studios with musicians to compose original music. But for many years, its founder refused to think of his company as a music company. He wanted it to be known a tech company -- and this led him to build a very tech-focused product for his clients, with lots of whiz-bang. He spent many...