Problem Solvers

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 than wait for the decline to come, he was going to shut down a major portion of his company now—sacrificing $30 million in revenue!—and rebuild it as a different company whose future looked brighter. This is the story of how he took such a big risk, and why it paid off.

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 would think of.

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 came to a realization: He was totally wrong about who to hire.

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 else to do the same.

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 is the story of how they began with an idea that didn't work, and pivoted into one that does.

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. This is the story of how Nicole learned to cope with the pain, surround herself with positivity, launch a new career, and be funnier and more popular than ever.

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 quest, and how Dunkin' finally got it right.

Here at Entrepreneur magazine, we hear a lot of stories about how entrepreneurs founded their companies. Many tend to follow a similar format. Someone has an idea. They take a bold risk to make it a reality, often sacrificing a fair amount of time, money, and relationships in the process. They become incredibly resourceful. They outsmart their competition. And at some point... they lie. It's so common to hear about an entrepreneur's lie -- to win over a first client, say, or to bring in resources when they're needed the most -- that we forget to pause and ask: Where's the line? On this episode, we consider the question with the cofounder of Stonyfield Yogurt, who saved his company in its early days with a particularly clever and daring bend of the truth.

When Matt Bodnar became CEO of Fresh Technologies, he took over a failing company and saved it from disaster. That felt great. Then he hit a wall: He couldn’t seem to get this company to grow, or to fix its internal culture. He began suffering from self-doubt. He’d always wanted to be a CEO, and he initially seemed good at it, but now here he was… failing! After a lot of soul-searching, Matt came to an important realization: He needed to identify what he was good at, and then use those strengths. And that meant no longer being a CEO. In this episode, we explore how Matt came to that conclusion -- and why it supercharged his career.

Just Between Friends is a nationwide franchise that runs consignment events. About a decade ago, it experienced a crazy jolt: It sold more franchise units than it ever had... and that fast growth nearly bankrupted the company. Why? Because here’s the difficult truth about growing a business: Not all growth is equal. Sometimes, growth in one part of your business can harm another part of your business. So to fix the problem, Just Between Friends had to hit pause and consider some very important questions: What’s the right way to grow? And what does it really take to get there?

Mike McDerment saw the future, and it wasn’t bright. His accounting and invoicing company, Freshbooks, was doing well with customers -- but behind the scenes, its software code was a mess and it wasn’t able to innovate as quickly as it needed to. But fixing this problem was tricky. If he ordered his team to hit pause and fix the code, years could go by and Freshbooks would lose ground to its competitors. And if his team did manage to create a better Freshbooks in the process, customers might be annoyed by the sudden change. So his solution was radical: He launched a competitor to his own company.

Raquel Tavares, founder and CEO of a ghee company called Fourth & Heart, had just finished raising a round of funding -- and then her team looked at the company's numbers and realized they were almost out of money. How did this happen? The answer is simple: The company wasn't properly tracking its inventory and cost of raw materials, and now it was in a terrible bind. What does an entrepreneur do in a situation like this? Raquel is here with an incredible answer: Not only can you survive a problem like this, but you can even thrive because of it. But you’ve got to be nimble, humble, willing to make a lot of changes, and able to stomach a lot of hard conversations.

It's perhaps the most terrifying situation an entrepreneur can face: Suddenly, the bank account is nearly empty. You can't pay your staff. You can barely keep the lights on. What now? This is what Saima Khan faced with her high-end cooking company Hampstead Kitchen. She charges a small fortune to cook intimate dinners for industry titans, celebrities, and even world leaders—but then a change in the tax law nearly wiped her out, and forced her to reconsider exactly what kind of business she was running.

Entrepreneurs must embrace change, or risk becoming outdated. In this episode, we offer a cautionary tale from history: What happened when entrepreneurs of the late 1800s tried to resist a newfangled invention called the bicycle? This episode is a special rebroadcast of a podcast called Pessimists Archive, also hosted by Entrepreneur magazine editor in chief Jason Feifer. For more like it, search Pessimists Archive on any podcast platform or visit www.pessimists.co.

Everyone who’s experienced setbacks, rejection, and frustration will ask themselves the same inevitable question: “What if the naysayers are right?” Mike Rothman did that. As he built his company Fatherly -- a media site for dads, which is a market everyone told him was nonexistent -- he was told “no” over and over again. But instead of quitting, he made strategic decisions that enabled him to discover the truth: His idea really was a good one. And soon, the people saying no started to say yes. Sponsor: Hover - visit hover.com/problemsolver for 10% off your first purchase.

Califia Farms makes a popular line of plant-based milks, yogurts, and coffees—but they became too popular, too quick. In 2017, demand began significantly outstripping supply, and so the company had to do something it hated to do, but that was critical for its long-term health: It had to start telling retailers "no," while it fixed its entire production system.

Orchard Mile, an online shopping site, had a promising platform and a talented team. But they had two very different ideas about what the company should prioritize. How CEO Jennie Baik made tough decisions to bring them together.

It's a question almost every entrepreneur will at some point face: How do you keep a company stable while you're pulled into a personal crisis? For Chris Carter, founder of Approyo, that question came shortly after his startup launched -- when his daughter developed epilepsy. After working himself to exhaustion, Chris stepped back and retooled how his company operated and how he was treating himself. The result was a stronger company, a healthier founder, and a better balance for everyone.

If you want to learn how to succeed without traditional advertising, ask someone in the "adult" industry. Why? Because most advertising channels—including Facebook, Instagram, Snapchat, and more—are closed to them. That's what Polly Rodriguez learned when she founded Unbound, a company that makes and sells adult products. Most platforms won't take her money, so she had to get creative... and build her own community.

How do you give new life to an old company? Bring new vision to a place that lost its own? And how do you bring your team -- and your new audience! -- along for the change? Those are the challenges Neil Vogel faced when taking over the old internet giant About.com and transforming it into a thriving company called Dotdash. Sponsor: Hover - visit hover.com/problemsolver for 10% off your first purchase.

Selling perfume online seems impossible. After all, people need to be able to smell it, right? And when former Ralph Lauren executive Eric Korman launched his online perfume company PHLUR, he ran smack dab into that problem. Industry peers thought he was crazy. He hung in and devised a solution: an ingenious a mix of smart e-commerce strategy, science, photography, psychology, music, and storytelling. And with that, he made the impossible possible.

People may like to shop for cars online, but they still want to test drive them in real life before buying. So when the online car sales company Shift launched, it created a system its founders were sure would win customers over: They hired “car enthusiasts” -- guys just really passionate about cars -- to drive a car to a customer so they could test drive it together. The car enthusiasts were a hit; people loved them, and praised them online. But Shift wasn’t celebrating: As it turns out, the car enthusiast program was so expensive to run that the company wasn’t actually making money. And that meant Shift needed to do something that felt crazy: blow up the feature everyone loved.

A company's name is one of (if not the) biggest early decisions a company founder will make -- and they often get it wrong. Google was first called BackRub, Best Buy was Sound of Music, eBay was AuctionWeb, and Policygenius was KnowItOwl. In this episode, Policygenius's founder walks us through the rigorous process she went through to scrap a confusing name and create one that led to success.

Patrick Llewellyn discovered that his design company, 99designs, was only fulfilling some of his customers' needs. He wanted to fill more, so he created a spinoff brand called Swiftly. But in doing so, he created a major problem for himself: He was stretching his resources too thin, and confusing customers about which brand they should use. In the end, he discovered the Curse of the Problem Solvers: Sometimes, you have to let some problems go unsolved.