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They Were Acquired... And Then The Buyer Went Bust

The apparel startup Richer Poorer thought it had found the perfect deal: A fast-growing e-commerce brand wanted to buy it, offering an influx of cash and resources while leaving the founders in control. But after the deal went through, a nightmare scenario folded: The new parent company started to collapse. In this episode, we learn how Richer Poorer's founders put the wheels in motion to get out—and saved their company just in time.


How Three Entrepreneurs Started On The Fast Track

Every entrepreneur’s journey starts with a big problem. That first hurdle—and hopefully, that first solution. Small and sometimes simple as it may be, this first moment contains so much ingenuity and inspiration, and captures just how resourceful entrepreneurs must be to continue along their path. Today, we’re telling three mini-stories of first-time challenges: how the creator of the Butterie butter dish cracked its market research problem, how GrowSumo found the right customers (and...


The Entrepreneur’s Identity Crisis: “Am I My Company?”

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...


How Do You Find Your First Customers?

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.

Duration:00:21:04's Problem: Their Popular Service Wasn't Making Money

Jen O'Neal and Jeff Manheimer launched a social network called, 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.


The Danger of Profitability: It Masks Deeper Problems

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).


Going From B2C to B2B: Why Poppin Transformed Itself

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.


How Transparent is Too Transparent?

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...


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

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...


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

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...


How to Win in a Ruthless Industry? Try Being Nice.

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...


How Tough Mudder Expanded Its Loyal Fanbase

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...


What’s Holding Your Company Back?

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 company start growing again, he’d need to make some gut-wrenching decisions.


How to Survive 150 Straight VC Rejections

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.


Survive the Holiday Crush Like Baked By Melissa

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 disastrous 2009 holiday led it to rethink fulfillment year-round—and win the holidays every year since.


Find Overlooked Growth Opportunities, With Study Giant Quizlet

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. Listen to his story, and learn how to find the opportunities hiding right under your nose.


What Happens When You Can't Deliver Your Kickstarter Project to Backers?

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 made some major changes to his business (and his life!) in order to survive, and now thrive.


Dollar Shave Club for Couches Shows Upside in Asking "Why Are Things Sold The Way They Are?"

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 reimagining how furniture is sold -- but to succeed, it first had to create a new way of making...


When You Try Making "Something For Everyone," You Attract Nobody

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 and refashioning its product. Now sales are spiking, and Grayl knows a lot about how to take...


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