Problem Solvers

Latest Episodes:

The Entrepreneur’s Identity Crisis: “Am I My Company?” Mar 05, 2018

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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 started. The result can challenge not just their business philosophies but their very sense of identity.

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How Do You Find Your First Customers? Feb 26, 2018

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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 company’s first customers into valuable ambassadors.

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Tripping.com's Problem: Their Popular Service Wasn't Making Money Feb 19, 2018

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The Danger of Profitability: It Masks Deeper Problems Feb 12, 2018

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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 making a profit).

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Going From B2C to B2B: Why Poppin Transformed Itself Feb 05, 2018

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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, Google, Warby Parker, and others.

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How Transparent is Too Transparent? Jan 29, 2018

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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 rolling with it. But what happens when the news is really bad? Can employees still be trusted to handle it? Besecker found out.

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How A Young, New, Female Boss Took Over Her Male-Dominated Company Jan 22, 2018

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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 this episode, Chrissy takes us through her first, critical year—and the tough decisions it required.

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He Said Yes Too Many Times, Then Learned to Say No Jan 15, 2018

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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 hired a COO who trained as a drill sergeant—and everything changed. Here’s how Hamilton learned to say no.

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How to Win in a Ruthless Industry? Try Being Nice. Jan 08, 2018

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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 her clients. As she tells us, competitors looked at her like she was crazy, but her business exploded.

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How Tough Mudder Expanded Its Loyal Fanbase Jan 01, 2018

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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 people too -- but without alienating those core fans. On this episode, we explore how Tough Mudder did it.

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