What Does It Take to be a “Best-Led” Company?

I spend a lot of time speaking and writing about the lessons I’ve learned as a leader, offering up my experiences as examples of the challenges I’ve faced in my career. Leadership is a topic that is near and dear to me. So you can imagine how thrilled I was last week to see that Hint was included on Inc. Magazine’s inaugural list of America’s “250 Best-Led Companies.” 

It’s an impressive list, highlighting great companies in every business category. No two companies among the 250 face the same set of challenges, and the examples they set of great leadership are equally varied. The editors at Inc. explain that they considered 14 different points of comparison in building their list — everything from “hiring and retaining top talent to putting out fires and managing amid a crisis.”

But for me, there’s been one core principle that has driven Hint’s success as an innovative, creative, and dynamic company. It’s our commitment to Hint’s underlying values. 

In the nearly seventeen years since I founded the company, I feel like I’ve actually led three or four different versions of Hint. First, it was the scrappy start-up, bootstrapped to the extreme. Those were the days when I was using my Amex card to pay for the bottles we used at our manufacturing facilities. We had a few employees back then — only the people who were crazy enough to sign on to a company founded by a former tech exec with no experience in the beverage industry. 

Then, there was the Hint a few years later that began gaining traction and expanding beyond our home in the Bay Area. Just as the Great Recession unfolded in late 2008. We were still a small company at that point; everyone knew each other on a first-name basis. We could fit an all-hands meeting in our conference room — and that’s where we often gathered to navigate our way through that financial crisis.

Today, Hint is the largest privately held non-alcoholic beverage in the U.S. with no ties to the giant beverage conglomerates (like Coke, Pepsi or Dr. Pepper). We have just over 200 employees all across the US. Hint flavored water is sold at major retailers and local grocery stores, as well as Amazon and our own direct-to-consumer channel, drinkhint.com.

The challenges of getting the company up on its feet versus steering it through an economic meltdown versus establishing itself as a household national brand each presented their own unique tests of leadership. Through it all, though, the one thing that has remained constant in each phase of Hint’s evolution has been our values. 

Hint was founded on a mission to make healthy choices easier for consumers. It was born out of my personal health journey, seeking an alternative to sweetened sodas — which I had discovered were contributing to my adult acne, weight gain, and lack of energy. I created Hint because I figured that there were many people out there, just like me, who needed this product. 

Over the years, hundreds of people have helped build Hint into the brand that it is today. Many of them were drawn to the brand precisely because of the mission that guided us. Hint’s values became our employees’ values, and our success was measured in the millions of customers whose lives were changed by our products. So when Inc. recognizes us as a “best-led” company, it affirms the entire reason we do our jobs each day. It validates that we’re making a difference in people’s lives every time they buy a bottle of Hint. And that’s the best reward of all.

Negotiation. It Might Not Be What You Think.

Robben Island, South Africa.

For decades, it was home to one of the most brutal, unforgiving prisons – a place that political prisoners were shipped off to and from which they rarely returned.

Nelson Mandela arrived there in June of 1964, and rather than accept his sentence of life imprisonment, he began a lengthy and calculated negotiation to not only free himself, but end Apartheid in his country.

Many have recognized Mandela as the greatest negotiator of the 20th century, deliberately deploying the tools of dialogue, leverage, and compromise in order to transform the fates of millions. His negotiation style and tactics have been carefully studied, offering insight into thinking strategically in order to achieve one’s ultimate goals. Even when it seems that one has little leverage in a negotiation process.

I’ve thought about some of the markings of a successful negotiator like Nelson Mandela and how certain techniques can be applied to any situation. Preparation. Assessing your strengths and weaknesses in the situation and figuring out what might happen if the negotiation doesn’t go the way you want. Understanding what the other side wants out of the situation too. And thinking about the various options they could develop too. Never ever go into a negotiation without a grasp of all your alternative scenarios. 

Nelson Mandela envisioned two futures for his country. One very dark one in which unrest and internal strife grew under the grips of Apartheid. And another where freedom and justice prevailed in a new social order. With steely perseverance, he was able to convince South African authorities that the alternative scenarios to a negotiated agreement were not in any of their interests. He was willing to walk away from the table several times. Eventually his persistence and persuasion paid off, culminating with the election of him as President.  

Understanding the position of the person or party that you are negotiating with is essential. Figuring out ahead of time if the goals for the outcome are the same or different from yours. When speaking with decision-makers to get our product Hint on the shelves of stores, or when trying to get more space on the shelf too, my team is constantly thinking about what the goals are for the buyers that are negotiating with. What is their goal? What will make them look good? And finally, being confident to share that this decision will be a good one.

Have you ever negotiated with someone who seems to care? Has empathy. And really seems like he wants to understand what you want to gain from the situation. Former FBI hostage negotiator Chris Voss is an expert at this, a strategy he calls tactical empathy. When brokering a deal, he suggests that using tactical empathy removes the often difficult, competitive aspect of a negotiation. And oftentimes, that helps both parties get aligned.   

Back in 2008, while we weren’t negotiating the release of hostages, we were negotiating with some of our retail partners who were suggesting that they would be taking some pretty drastic measures that we weren’t thrilled about — removing us from store shelves.  Remember this was at a time too when the financial markets were melting down and many were fearing the worst about the economy and consumer spending. We were fielding calls every day from grocery buyers who wanted us to agree to BOGO pricing — that’s buy-one-get-one free – in exchange for keeping our product Hint on their store shelves. The economics of this deal definitely didn’t make sense for us, and many of the ones who were threatening this deal immediately backed off.  

But there is always one. And one very important retail partner who was determined to stand their ground to maximize their economics even though this was completely unsustainable for our business. How did we solve this potential catastrophe? Empathy was the key to solving this problem.

We told them that we couldn’t agree to that kind of discounting, and we were willing to walk away. We stood our ground, knew what the possibilities were, and in the end, we finally agreed to maintain our existing pricing. 

Stephynie Malik, a top crisis management expert, talked about bringing compassion to the negotiation table when she was on my podcast The Kara Goldin Show. Her work at numerous companies over the years to untangle sticky situations and ensure that the communication to the media is handled the right way is key to getting a company or an individual out of crisis mode. Malik shared that when people are negotiating these types of situations, many times they opt for hardball tactics. And while she has seen that strategy work, in most instances, the potential outcome that one thought they were getting usually falls apart. Bringing empathy upfront to the negotiation all parties are heard and acknowledged. And hopefully the resulting deal will be one that both parties feel a bit better about.  

When Nelson Mandela asked why he was able to negotiate what he did to end Apartheid and by all means succeed against the longest of odds, he had this to say: “I am fundamentally an optimist. Part of being optimistic is keeping one’s head pointed toward the sun, and one’s feet moving forward.” 

Whether or not you are an optimist. And regardless of whether or not you are brokering a peace treaty or hammering out a business deal, remember that as difficult as today may look, negotiations are what will move the situation forward. And allow new opportunities to arise too. 

In your next negotiation, keep your head pointing towards the sun and allow progress to be made. Like a true optimist.  

Going Against the Grain. And Why It’s Often Necessary.

“How can you be sure?”

“You’re betting this is what consumers want.”

“That’s not what experienced industry experts would do.”

Doubts and doubters. I wrote a whole book about them. Because I learned over the course of my career that nothing was more rewarding than fighting off those voices — both the ones in my own head and the ones from skeptics — and finding success in the end.

To succeed you have to be willing to stand up for what you believe even if it means you go against conventional wisdom. I turned down plenty of advice from people seasoned in the beverage world because it would have meant acting counter to the brand I wanted to build and the company I wanted to lead.

When I insisted on Hint being bottled without preservatives, experts told me that I’d never be able to extend the product’s shelf life and distribute it nationwide. “It’s just not possible,” I was told. Those were the facts that the experts knew at the time. And I recognized how their experience put blinders on them to see what was possible. To be able to innovate how a product was made. Or have any reason to.

Eventually, we were the ones who found a way to innovate the bottling procedure without using preservatives. Listening to the seasoned vets wouldn’t have allowed us to think differently and innovate as we did. It took some tinkering. It took some time. But eventually, our persistence paid off.

Many times, the advice I’ve received has come from people who were well-intended. Friends who were worried for me when I left the tech industry expressed their concerns because they didn’t see the purpose and meaning that I envisioned. The fact that these people I loved and trusted doubted my “why” made it all the harder to quell the doubts in my mind.

Ultimately, I knew I needed to keep pushing further on my pursuit. I hoped that Hint could help people get healthier. I believed that a powerful upside outweighed the risk of failure. And even if I couldn’t turn Hint into a thriving business, I believed that I could walk away with skills and knowledge that I might never have gained otherwise. And for me, that would constitute my purpose for continuing.

Going against the grain builds grit and determination. Even in quote-unquote “failure.” Going against the grain requires creativity to think of solutions to problems that haven’t been considered. Going against the grain exercises muscles you probably didn’t know you have. And stretches you to learn key lessons through lived experience. The best way to learn.

I knew from having grown up the youngest of five kids that my own observations and experiences were critical to my learning. When your gut tells you to go against the grain, even if it means rejecting seemingly expert advice, you’re probably doing the right thing.

I spoke to Arlan Hamilton, founder of Backstage Capital, for my podcast, The Kara Goldin Show. She pointed to one characteristic that has driven her success in fields that she entered with relatively little experience. “I just knew that I had something that other people didn’t have, which was a certain vision, and the willingness to just go all in.”

The willingness to go all in. So key! When that passion and curiosity take you further than any textbook or expert advice while you stop at nothing to solve the problems in front of you.

Esther Wojcicki is a trailblazing teacher, writer, and entrepreneur who has spent decades in Silicon Valley pioneering in the field of education. But that wasn’t her first calling. She recounted to me her early forays into journalism back in the early 1960s, when editors only offered her staff positions writing for the “women’s section” of the newspaper. “Can you believe that?” she said, still irked by the experience decades later.

So what did she do? She wrote the stories she wanted to write and sold them as a freelancer. And she started teaching journalism to high schoolers, cultivating a new generation of reporters and writers who, along with her, would go against the grain and reshape an industry with outdated ideas and antiquated power structures. You figure out how to move forward.

That’s the real value we bring when we challenge ideas and traditional ways of doing things. We clear out some of the received wisdom that’s been passed down from generation to generation without question. We swipe away the cobwebs that obscure new ways of thinking. That’s how we evolve. That’s how we innovate. Through trial and error. Learning from our mistakes and oversights.

One of my all-time personal heroes, Ruth Bader Ginsburg, is famously quoted saying, “Real change, enduring change, happens one step at a time.”

Be part of that first step. Stand up for what you believe in. Find a way to do what you believe is possible. Be the change you want to see in your world. While it can be a lonely road at times, it can also be a gratifying path to take. And a rewarding one too.

Risk, Reward or Both?

If you’ve watched “Shark Tank,” you know that moment – when the panelists have just made their offer and the entrepreneurs have to decide, on the spot, if they’re going to take the plunge.

It’s the same tense moment built into almost every game show. Whether it’s trading what’s behind Door #1 for Door #2, or putting it all on the line for Final Jeopardy — when contestants have to decide whether to stick with what they had earned thus far or risk it all for a potentially bigger payout.

How do we make those decisions? And how good are we at judging the risks relative to the rewards?

It turns out that we’re making those choices every day. And when we aren’t on a TV show, we’re most often sticking with what we’ve got, continuing on the same general trajectory we’ve charted for ourselves. It’s true for the little decisions that need to be made – products bought regularly out of habit, the route taken to work every day. And it’s even more true for the bigger commitments people make in their lives.

People tend to resist stepping back and changing courses. It’s scary. Betting it all and pursuing the dream or the business idea they have percolating in their minds. The excuses come easily: I haven’t gathered all the information I need just yet; or I don’t know if now is the perfect time; or I’ve got a pretty good thing going as it is.

Those who follow me or who have read my book Undaunted: Overcoming Doubts and Doubters know that one of my favorite pieces of advice I like to give is to “fly the plane while you’re building it.” Of course, taken literally that would be a daunting and a very dangerous proposition. But as a metaphor, it brings home how important it is to step into that area of risk and uncertainty just outside of your comfort zone. Because the metaphorical airplane that we operate each day of our lives is always a work in progress;it’s never fully built. So you can opt to idle on the ground, safe, secure and stuck in place OR press on the gas, tilt those wing flaps and take off.

You decide. After all, you’ll never know if you can succeed if you never try.

Nobel Prize-winning psychologist and economist Daniel Kahneman has posited that “loss aversion” dictates so many of the decisions we make, often to our own detriment. Loss aversion is a behavioral theory that describes people’s tendency to focus more on the costs or risks when offered a choice – even when the upside might far exceed the greatest potential loss.

Kahneman talks about starting his class each semester with a coin toss, saying that if it landed on tails, students would have to pay him $10. “How much would you have to gain on winning in order for this gamble to be acceptable to you?” he would ask. The answer regularly came back at $20. (He would offer the same deal to C-Suite executives, upping the ante to $10,000; they invariably wanted a $20,000 return if the coin landed on heads.) According to his research, the pain of losing is perceived to be twice as powerful as the thrill of profiting.

So how do we break out of this pattern?

It’s not easy to decide when to take the plunge. I can attest to that. When I started Hint, I can’t tell you the number of people who questioned my choice to venture out on my own to start a beverage company versus continuing in a “safe” tech job.

“Is this really the right time?” friends and family would ask.

“Isn’t it risky for you to leave tech and go into another industry you have no experience in?”

“What if it doesn’t work?  Will you be hireable? ”

Here’s what I have concluded.  The thing is, no one really knows whether you will be successful at your new venture. And no one really knows what you NEED in your life either.  So take what they say with a grain of salt.

Taking risks is scary. To all. But going “off course” allowed me to figure out what I was capable of. And what I am good at. And what I am interested in. And I knew that even if I didn’t succeed, I could speak to what I had learned along the way. And I hoped, believed, that I would still be a strong hire should it all not work out. I knew that I would learn new things and acquired some new skills that I wouldn’t have gained otherwise. Still, I had to remind myself why I was taking this plunge. And the voices from doubters and skeptics to “stay in my lane” in the industry that I knew only increased my own doubts in this new world that I was entering.

Emma Isaacs is the CEO of Business Chicks, a global community of over half a million business leaders, and the author of Winging It.  Her book is a manifesto and a rallying cry for us to pursue the things that are scary and might even result in failure. But that pursuit, she says, will lead us to places we never imagined.

On my podcast, Issacs urged listeners to give their dreams a go and progress without having all the answers. The key she says is to back yourself and have the confidence to press on without having a roadmap of where it’s going to take you. You’re never going to chart a new direction looking at an old map. The real treasures lie off the beaten path.

We all know the famous maxim that a bird in the hand is worth two in the bush. But here’s my question in response: How many birds exist beyond that bush — in the trees and on the ground and circling above? Don’t just focus on what’s at hand. On what you possess now. On what you know today. Go out and explore the universe for all possibilities. Challenge uncertainty.  Look at risk and say, “Yes” more than “No.”

Take those first steps. They will be behind you before you know it!

Get Going and Disrupt Already

Over the years, I’ve witnessed countless entrepreneurs disrupting established industries. And while it may be surprising to some, the most innovative thinking often comes from people who leave one industry to join another. These people bring a different perspective. A new lens. A fresh pass that often drives change.

Yet, conventional wisdom doesn’t often lead us to predict this. It’s certainly something I was never taught. In fact most people are told that people should only try their hand as an entrepreneur and start companies AFTER they have gained experience in a particular industry. But what if we didn’t know the rules of an industry? What if we hadn’t followed the same pattern over and over again to success. What if we are just newbies to it all or a new industry?

I often refer to myself as an accidental entrepreneur. Maybe different from what some of you imagine. I didn’t dream of starting a business. Entering the ultra-competitive beverage industry wasn’t something I ever imagined myself doing either.

But here’s what drove me. Curiosity. And the ability to solve a problem. A puzzle I had been thinking about.

In order to innovate and create a new product and company – not to mention a new category – in any industry, it takes courage. Or stupidity. Or a bit of both. I credit my early experience in tech, where I learned to build the plane while flying it. Creating and innovating and honing my skills. I had fun leading a group of people building out partnerships for what would soon be known as the leading platform for online commerce back in the early days of direct to consumer. Charting new territory and leading the build of a billion-dollar business for AOL. It was truly the wild west.

Those skills – not knowing what was in front of me most days, but imagining what could happen regardless – would transfer to the beverage industry nicely. That curiosity to learn a new industry and a commitment to change an industry for the better. To create a water that just tasted better without sweeteners in it – sugar or diet sweeteners. And tame my diet soda addiction. I thought it could help a lot of other people who were searching for a similar solution too, but just hadn’t realized it yet.

Had I worked my way up through the beverage industry, I may not have seen my vision so clearly. Coming up with an idea that would challenge diet soda and enhanced waters that were supposed to be better for consumers would be taboo. Eat into market share with a product that eliminates sweeteners altogether? Unlikely. Who needs that?

Over the years, I have heard from many experienced beverage execs that the idea for Hint could have only been created by an outsider. And it was. I was once told by a certain soda exec, after I started Hint, that the consumer of that time (about 15 years ago) wanted “sweeter drinks with less calories.” Given my own personal experience, I couldn’t help but wonder if he ever thought about the consumer who may figure out that those sweeter-with-less-calorie drinks are doing more harm for ones health than good.

The early days of Hint were challenging for sure. We made many mistakes. From the clear label design that no one could see on the shelf, to figuring out how to make our product without preservatives. Most industry vets would have closed up shop before they even got started. Challenge after challenge. And each time, I found myself getting back up. I wasn’t going to allow those gnarly challenges to stop me. Instead, facing every roadblock like a new interesting puzzle. And entering each day excited to keep asking, “What can we do?”

That curious mindset. Where you live to iterate and constantly improve. And in our case, a different kind of thinking brought to an old industry where most felt that they had the consumer all figured out.

Once in a while in those early days, I would run into established beverage execs. And often I would take the opportunity to drop a few questions their way. I’ll never forget how most would answer, knowing that I was an outsider who didn’t come from their world, “Well that’s not how it’s done in this industry.” While those statements often irritated me, I often took those statements as opportunities to follow up with, “But why not?!”

And while most that I encountered didn’t actually know the answers to my often unique questions, that didn’t stop me either.

Entrepreneurs crossing over into new industries bring a new way of thinking. Fresh ideas. Weird questions. Entrepreneurs who are able to draw outside of the lines and break new ground. The people who will eventually disrupt and change things – and hopefully for the better.

Divya Gugnani is a prime example. She’s the CEO of Wander Beauty, a brand that has blazed a trail in the cosmetics and hair care industry. What did she do before starting Wander? Divya had launched an after-market car parts company, a culinary business, and a fashion accessories startup. Not the conventional CV one might expect from a beauty brand founder just killing it in the space.

“Entrepreneurs see things that others don’t see,” Divya said when she was a guest on my podcast, The Kara Goldin Show. “They take risks that others don’t take. They see problems and create companies to solve them.” Divya leaned into cruelty-free, clean formulations that “multi-task” so that her on-the-go customers could pack fewer beauty products with them when they wandered (get it?) beyond their home base. It was an innovation that no one else in the industry was thinking about -– or was brave enough to launch a company around it.

Julie Wainwright, founder of theRealReal.com, is another one of my favorite entrepreneurs. You may be surprised to hear that she had never been to a consignment store or bought anything on eBay before she started her mega-successful now public company. Her ideas started to build after a shopping trip with a friend to a secondhand store where she recognized the white space in the luxury goods resale space that no one was addressing.

“I actually started with just a little bit of money – not a lot of money. I started by figuring out, how many brick-and-mortar consignment stores there were? How does eBay handle luxury goods? How is luxury jewelry sold online?”

For many, seeing the vast white space of opportunity is enough to make one run and hide. An opportunity to come up with a million reasons why a new business idea won’t work. Many might fear an already established industry player. Or think too much and make the execution seem too difficult. Maybe get ahead of themselves – “Who wants to invest in the resale clothing market?” But entrepreneurs like Julie see all the reasons why an idea can work, applying their previous experience to test assumptions and make it all happen. A great idea and killer execution. This is exactly what made The Real Real into the indisputable leader in luxury consignment.

Tim Brown is another terrific entrepreneur who crossed industries. After a career as a professional soccer player, his interest in footwear came naturally from years of wearing different types of sneakers. He founded the Allbirds shoe brand like a true outsider – taking wool material and making sneakers out of them. An idea that many established footwear execs had ignored.

On my show, he explained how many in the footwear industry doubted his ability to produce a quality product that people would wear. Industry experts told him that he was wasting his time. The feedback he received, however, helped him realize that he was ahead of where others were. And because he saw the industry with a different lens, he could imagine what could be. What consumer’s might buy.

So my advice? No matter where you are in your career, the puzzle and the problem are yours to solve. Go out and disrupt. And don’t be inhibited by stepping into an industry you know nothing about.

The world is yours to add your positive mark to.

I’m counting on you.

My Favorite Piece of Steve Jobs Wisdom? Trust That the Dots in Your Life Will Connect

Entrepreneurs come in many forms – each with different origin stories that led to the founding of their companies. Some look for white space in a category and then fill a consumer need that hasn’t been met. Others spot inefficiencies or irregularities in an industry that technology can fix.

My own path to launching a start-up was more personal. The result of a need to solve a problem in my own life. It’s a path that I’ve seen many other founders follow. You make a significant change in your daily life and see the kind of positive impact that it can have. And then you start to look outward and think, “How can others benefit from this?”

Soon, a bigger idea starts to coalesce. And once you decide to make the leap and turn that transformative idea into a business, you not only have a product to take to market, you now have a mission to fulfill.

My story is known to many at this point. I discovered that my diet soda habit was leading to all sorts of persistent health issues – weight gain, adult acne, lack of energy. The problem for me was that I found water to be boring, so I started cutting up fruit and adding it to my eight glasses of water each day. My new, healthier habit caught on – and not just with me, but with my family and friends. People would come over to our house and ask where I’d bought this flavored water, and that’s when the light bulb popped on in my head. These concoctions I’d mixed up in my kitchen could be the start of something big.

At that point in my career, I had decided to take some time off from corporate life after years of grueling travel and long work hours. I had three kids at home, and I wanted a change. I decided that my next chapter would need to be different. I thought about working at a non-profit or finding a company that genuinely wanted to make a difference in the world.

In a commencement address he gave in 2005 at Stanford, Steve Jobs famously talked about a series of random – but meaningful – experiences in his life that all came together when he was designing the first Macintosh. He offered his journey up as a lesson to those young graduates. “You have to trust that the dots will somehow connect in your future,” he said.

This was my dot-connecting moment. I had solved a nagging problem in my own life, and I knew that there were others out there who could benefit from the changes I’d made. I also wanted to funnel my energy into a company with a mission to make people’s lives better. And now I had a vision for creating a product that would bring it all together. Connecting the dots. And thus, Hint was born!

I’ve talked to so many other entrepreneurs who followed the same path – experiencing revelations and changes in their personal lives that altered their professional paths.

Julie Smolyansky is the CEO of Lifeway Foods, a pioneering brand in probiotic foods founded by her father, an immigrant, in the late ’80s. But running Lifeway was not Julie’s original vision for her career; her passion was working in the field of psychotherapy, motivated by a desire to make a difference in people’s lives. “I wanted to change the world. I wanted to reduce people’s suffering,” she told me when she was a guest on my podcast, “The Kara Goldin Show.”

Her mindset shifted, however, when she started digging into the research around mental health and diet – and how probiotic foods factored into positive psychological outcomes. Julie realized, “Wow, actually, I see a usage for this… our product, our kefir, has ancient healing that changes people’s lives. It improves people’s lives.” She dropped out of graduate school and worked alongside her father for the next five years, learning the ins and outs of the family business.

When her father died unexpectedly in 2002, Julie stepped in to run Lifeway, becoming the youngest CEO of a publicly traded corporation. “Everyone around me said, ‘There’s no way a 27-year-old girl could run this company. Forget it, the company’s done, sell your stock,’” Julie recalls, “And that really fueled me, that gave me a fire in my belly, and a defiance, and I was just adamant about proving those men wrong.” Julie’s mission – to improve the lives of her customers and prove her doubters wrong – has driven the success of Lifeway over the last two decades, leading the way as probiotic foods have surged in popularity.

David Melzer is one of the most storied agents in the world of sports, but his greater passion these days, as he told me recently, “is to be of service.” David scaled the heights of his industry, and then in 2008 lost nearly everything he’d built over the course of his career. At that point, he says, “I had to take stock in who I was and what I wanted to become.” In the process of rebuilding his life, David felt that his perception of happiness had become distorted – and he saw others around him amplifying the wrong things as well.

That realization led to an entirely new thrust of his career. “My life now is about giving myself away,” he says. Sharing the lessons he has learned. He is the author of four books (one of which, “Connected to Goodness,” he offers as a free download). He’s the host of a must-listen podcast, “The Playbook.” And he leads free weekly online training sessions designed to help people reach their true potential. His goal to inspire people to find success – and be their best selves – has affected tens of thousands of people, and it has become David’s primary calling.

There’s a common thread I see in my own path and in others who have channeled a personal passion into their careers. Success becomes judged by a different standard. When your mission is driven by a greater good – and a change for the better that you yourself have experienced – your gratification comes from the people whose lives you impact. Early on with Hint, it’s what drove me to persist through the countless challenges. Seeing all the emails and hearing all the messages that Hint drinkers were sending us. Our little company was making a major difference in their lives. People with type-2 diabetes, people battling through cancer, people who just wanted to make healthier choices in their lives. Their love of Hint motivated me.

Then there’s this: Once you’ve gotten some traction and your mission-based business starts taking flight, you begin attracting like-minded people into your orbit – investors, partners, employees who share the same passion you have for your business. Some have experienced similar changes in their own lives. Others are drawn to the idea of making a difference in the world. As Hint expanded, we were able to pursue ideas beyond flavored water: sunscreen and deodorant and hand sanitizer that gave consumers easier access to healthy choices. Our mission was snowballing!

Of course, not every entrepreneur finds immediate success or success at all. Not every business catches on. Maybe the timing isn’t right. Maybe consumers aren’t quite ready for your product. But the work you do to put your idea out there and share your story through your company’s mission will enrich your own path. You’ll learn new things. You’ll challenge yourself. You’ll adapt. You’ll start connecting the dots. You might try again. You will become more resilient. You will grow. And, maybe, you’ll see how some small alteration you’ve made in your own life can spark an idea, gain momentum, grow into a thriving business, and impact the lives of millions.

You’re Good Enough, Smart Enough and Doggone It, People Like You

‘I’m good enough, I’m smart enough, and doggone it, people like me,’

That mantra was introduced into popular culture by a 1990s “Saturday Night Live” character named Stuart Smalley, who mindfully recited his daily affirmation into an ornate, full-length mirror. While my twenty-something self (at the time) enjoyed the sheer comic value of Stuart’s shtick, it was later in my life that I would realize the indelible impact that Stuart’s words had on me. In fact, they were a small seed planted in my mind that foreshadowed my entrepreneurial success with Hint.

Today, millions of individuals are choosing to become entrepreneurs. In our lifetime, we may never see more career reassessments and pivots than those taking place during this COVID pandemic, which is already showing signs ofoutpacing even the 2008-2010 Great Recession in new business creation.

Many of these new founders are just where I was back in the early ‘00s, starting down the entrepreneurial path a bit later in life. Let’s call them unlikely or accidental entrepreneurs. That’s how I saw myself – and still do! It wasn’t my vision from birth to start a company. I was in my mid-thirties when I launched Hint (with three young children; pregnant with my fourth), and like many new entrepreneurs that I’ve talked to this past year, I was embarking on a business where my curiosity and determination far outstripped my expertise in the industry I was entering.

For these newly minted founders, Stuart Smalley’s Daily Affirmation may be just the tonic to keep them going, as all the naysayers and doubters and skeptical industry veterans (you know, the folks who always know exactly how things should get done) interject themselves on the road to success.

My own story is a tale of grit, perseverance and a lot of asking questions, starting with “how?” and “why?” I went from being a tech executive with a dependency on diet soda to a founder of a company, staking out an entirely new category in the beverage industry – one truly based on health. Initially, everything I knew about beverages was based on a sample of one. I was addicted to sweet diet drinks, and I had convinced myself that the word “diet” on the label meant that the product must be healthy. It didn’t take me long to figure out that it was anything but. And my gut was telling me that many other consumers were being confused in the same way.

So I went to work, asking questions and searching for the right solution. Within months, the first bottles of Hint hit the beverage aisles in San Francisco. Fast-forward sixteen years later, Hint is the fastest-growing independent beverage company in the country.

Here’s what I’ve learned in that decade and a half, and this is what I recommend to the next generation of accidental entrepreneurs:

• Experience is a double-edged sword. When you know what’s possible because you’ve been there, you know onlywhat’s possible because you’ve been there. History tells the story of boundaries being pushed and breakthroughs being achieved by fresh, curious minds. Don’t underestimate the power that comes with asking questions – and with questioning legacy thinking and long-held industry practices.
• Everyone has fear and doubts. The key is pushing past them. The best athletes in the world; the greatest virtuoso concert violinists; the most lauded actors and performers – they all have DOUBTS. That never goes away. But the successful ones amongst them face their fears and don’t cower from challenges.
• It’s okay to fly the airplane while you’re building it. In fact, it’s necessary. If you’re waiting for all the stars to align, you’ll never get your business idea off the ground. As long as you can deliver on your product’s basic promise – its core benefit to consumers – you’re ready. Just start. Because guess what: you can never succeed if you don’t start!

And to Stuart: thanks for the advice. We’re all good enough, smart enough, and likable enough, doggone it. This next-generation of entrepreneur – whether they’re a newly-fangled bagel store owner who used to be in IT; or the stay-at-home mom now starting a college prep business; or the long-time HR professional working out that long-repressed aggravation by opening a karate dojo – they should similarly remind themselves that anyone can do it if they have the passion, curiosity and determination to make it happen.

Starting a Company – and Why Not Having ALL The Answers Is Better

“Just start. Because you will never succeed if you don’t.”

I’ve given this advice countless times when I see future entrepreneurs hesitating on taking the plunge. The logic behind it is self-apparent: you’ll only ever achieve success if you actually get out there and try.

No alt text provided for this image

But there’s another lesson embedded in there, and it’s this: you will make mistakes no matter what new challenge you take on. There’s no way around it. With any new venture that you throw yourself into, there is going to be a learning curve and things will happen. And no matter how much you plan or try to anticipate what those mistakes will be, they just will happen.

Lesson #1: Get Your Product Out There

When we launched Hint, we spent a lot of time thinking about how we wanted to present the product – and differentiate it from the competition. What was unique about Hint? It had no sweeteners. It had no preservatives. And unlike many of the “healthy perception” products on the market, Hint was clear in color.

So naturally we thought the label should be clear too – different from the label on other brands. A clear label would reflect the purity of our product and make it distinct from everything else on the shelf. Simplicity and clarity – exactly what I wanted people to remember about Hint.

When we looked at the final product on the counter in our kitchen, it looked perfect. But once it was on the shelf under supermarket lighting, another story could be told. Our beautiful label was tough to read. The product with the beautiful clear transparent label, disappeared on the shelf. And when placed next to other products on the shelf – especially the ones that had color in them like Vitamin Water – our product seemed nonexistent. And unfortunately, we weren’t choosing where we would be on the shelf. Or if we made it into the coldbox. Those problems could shift each time; lighting was different in each store – and even within different areas inside a store.

We eventually switched our beautiful clear label to a white label. We found that the new white label allowed the product to really pop. While we learned early on that people who found the product enjoyed it — and became early fans — it was when we made this tiny but important switch that sales increased significantly.

So what’s the lesson? Get your product out there for the customer to see. You will always find things that need to be changed that you didn’t anticipate. Always. And hopefully you will not have sunk too much money into making it “perfect.”

No alt text provided for this image

Lesson #2: Not Having The Answers is Often Better

One of the things that was critically important to me when we launched Hint was to show people that drinks can taste good without tasting sweet. I’d seen the health benefits myself – ditching diet soda in favor of water that just tasted better with a little taste of fruit. That’s all that I needed to start enjoying drinking water.

Without preservatives though, my product had a limited shelf life. Whole Foods was telling us that if we wanted to stay in their stores, we needed to solve that issue. And launching Hint nationwide was certainly out of the question until we could figure it out.

If I had come from the beverage industry – or if I had taken the advice of anyone from the industry – I would have never decided to dive in to such a big undertaking without first having a solution for this shelf life issue. The easy fix was to add preservatives, which I didn’t want to do. Or I could continue delivering Hint to supermarkets out of the back of my Jeep. The future of Hint was in serious jeopardy if we couldn’t figure a way out of this problem that no one seemed to have the answer to.

The really important lesson here? Not having all the answers – and not being burdened with a lot of institutional knowledge – turned out to be a blessing. I was an outsider. I didn’t know what I didn’t know. And when I asked questions about fixing this issue, people treated me differently. They entertained my curiosity a bit more. They forced themselves to be open to solving previously unsolvable problems.

Sure enough, I stuck to my guns. Mostly because I didn’t know better and I had no other option. And we solved the shelf life problem soon thereafter without preservatives. Often, not having all the answers actually works to your advantage!

Lesson #3: Cold Calling Can Work

One of the first marketing strategies we employed was featuring Hint at high-profile events where we could generate buzz. It was a way for us to get trial from people, and hopefully they would pass on their love of the drink to people they knew. I made a connection in early 2005 which led to Hint being served in a prominent way at a party at the TriBeCa Film Festival. This was great news, but “being” at the party — Hint that is — without having a nearby retailer who stocked Hint would be a huge misstep. It was critical that once people got acquainted with the brand that they could then buy our product at a local store. DTC was non-existent for beverages back then.

So I quickly got to work. Back when I lived in New York, I shopped at a small grocery store in Soho, not far from where the TriBeCa Film Festival took place, called Gourmet Garage. They seemed like the perfect place to buy a product like Hint. So I looked up their number, made the call, and I was promptly connected to a woman named Kara, their grocery buyer. I told her that my name was Kara, too, and that my husband and I used to live in New York and had loved shopping at Gourmet Garage. And I had a new product that I thought their customers would love.

She asked me to send some samples. I, of course, had already sent them, and I told her they would be arriving that day. She called back later, said she loved the product and they would be happy to stock it. I don’t know if it was the product, the fact that we had the same name, or something else, but I’ve never had an easier time getting to “yes” before or since then. I was smiling ear to ear.

The lesson was the same one I learned early in my career. Cold calling works. Sometimes. And the key thing with a cold call (or cold email) is making sure that you have something really worthwhile to offer the person on the other end. I sensed that Gourmet Garage was the perfect market for Hint – because I had shopped there for years and knew their brand intimately. So when I sent those samples off to Kara, I was confident that the product itself would seal the deal after I made that cold call.

And it did.

When You Have Options, You Can Weather Any Storm

Options.

What so many forget to make sure they have. In life – and in business.

I learned that lesson the hard way about ten years ago when I got a fateful call from our buyer at one of our most important accounts at the time. Starbucks. And I was told that what had been consuming my life for the last eighteen months was going away in two weeks. Two weeks!

We had been fortunate to gain chainwide distribution in Starbucks – just over 6800 stores throughout the US. That was a good day when we received that news. It took us about six months to achieve our goal. And after that, we were rockin’ it! Exceeding our sales targets by almost 3x. Then, we were given the notice that Hint would be discontinued from all those store cases at Starbucks. Every store. A bad day for sure.

In retrospect, I can’t say there were warning signs. Hint was selling well above our goals. There was a buyer change. And, we soon learned, a strategic shift from the top. It was decided that the coffee company needed to make room in their cases for sandwiches and more expensive items that had a higher margin and higher ring. While this all made sense for Starbucks, this new strategy was bad for Hint. No sugarcoating it.

I got off that phone call, politely and calmly. And then I laid my head down on my desk. What was I going to do? Six months’ worth of inventory was sitting in the warehouse that would go bad. While we had other retail customers, we didn’t have another customer that could make up for this gap. What were we going to do with all this product?

I thought long and hard about what I could have done differently. And I came up with one answer. We had put too many proverbial Hint eggs in the proverbial customer basket. That account for us represented a huge chunk of our overall business – almost 40% of our total revenue. And that’s the issue I should have recognized months earlier: not thinking about a way to diversify or have other options if that business suddenly disappeared. We were vulnerable.

When you have an important account or client, it’s everyone’s tendency to stay focused on that relationship. Make it the highest priority to meet the goal. Or over perform. But it’s a balance. In fact, the most prudent thing we could have done while building that Starbucks distribution was to go out and find a few other revenue streams. And ensure that we had options if and when that high-priority account went away.

The funny thing is that I’d always been very good about making sure that I had options. When I embarked on my post-college job search, I set myself up with almost 100 interviews. While I was at AOL running their e-commerce and shopping partnerships, I would always go after more retailers, knowing that not all of our partners would be successful online, at least not right out of the gate. Years later, I started Hint knowing that if things didn’t work out with my first entrepreneurial venture, I had the option to go back into the tech industry.

I had a similar conversation recently on my podcast The Kara Goldin Show with Alex Lieberman, the co-founder and Executive Chairman of Morning Brew. He reached a fork in the road professionally a few years ago, while working full-time in finance and writing his email Morning Brew on the side. There weren’t enough hours in the day to work on both of his interests. He had to make a choice.

So he thought through all the worst-case scenarios if Morning Brew failed. “If I didn’t burn all my bridges at Morgan Stanley, I could go back there and actually this makes me a more well-rounded trader,” he recalled. “And I basically got several layers deep into what I thought were other realistic options.”

Turns out, none of Alex’s fallback options were necessary since Morning Brew exploded in the ensuing year and became the go-to business news brand for millennials. Not long after, the company was acquired by Business Insider. Having options allowed Alex to commit fully to his venture.

Cate Luzio was another recent guest on my show. She spent decades in the financial services industry before pivoting to an entirely new business. In 2019, she opened Luminary, an event space for collaboration and community. One year later, the pandemic unfolded and completely altered Cate’s business model. Fortunately, she refused to stay still. She found options.

“When the pandemic hit… we were fortunate that we could really be nimble, the team could react quickly and I could make those tough decisions,” Cate said.

Cate shifted her business online quickly given that in-person events weren’t going to be feasible for the foreseeable future. And a surprising thing happened. “Going online for us was incredible. It accelerated our growth dramatically. We will always now have a virtual and a digital platform as part of our plan. And now we even have members around the world.” Having options – in this case, finding new ways to quickly maintain revenue – allowed Cate to lead successfully during the pandemic.

So, back to our story at Hint. How did we handle the situation with Starbucks in the end? That was a painful lesson, to be sure. And it would be tempting to just feel vindicated for whatever perceived slight I had felt. But Starbucks was doing what any responsible company does: they were doing what was best for their business. And unfortunately, that was not necessarily what was ideal for my business. The only thing that I would have asked for is longer than two weeks’ notice.

I always say that it’s important to look back on challenging times. For those options, and also for the learnings. Here’s what else I realized:

Starbucks introduced Hint to millions of customers who would have never been able to try our product since we didn’t have distribution in many areas where they had stores. That exposure was invaluable. And that led me to realize something else that I was missing from our business. Our own connection with the consumer. Because if we would have made that connection, or had the emails from the people who purchased our product at Starbucks, we could have shared that Hint was still available elsewhere. Or online at our own site www.drinkhint.com.

And for that reason alone, I am grateful for the experience with Starbucks and for making me realize what I was missing from my business. Another option for connecting with the customer. My own.

What options are you planning to create for your career? Or your business? I would love to hear.

My Message to Graduates in the Class of 2021? Go Out and Create Your Own Opportunities

Hello Everyone!

Thank you for taking the time to read this.

This month I’m hitting a big parenting milestone. My first child graduating from college and embarking on “real life.” It brings up a lot of emotions and memories for me, going through the same rite of passage many years ago myself. My first job search. My big move from Arizona to New York City. My tiny Upper West Side apartment. But I’ll get to all that in a second.

First, I’d like to say something to the graduates in the class of 2021.

I don’t need to tell you what a unique group of graduates you are. The unprecedented circumstances of the last year have re-written the rules of what many of us faced after college. Without a doubt.

Graduation – in any year – is an emotionally complicated time, with so many unknowns and so many possibilities. It probably seems to you like the future is more intangible and unpredictable than ever.

But here’s one thing I know about times of uncertainty: the best opportunities for change happen in moments like this. Smart companies and savvy entrepreneurs are making plans right now, investing in what comes next, anticipating the upturn that always follows a time of upheaval.

My advice? Stay curious. Ask questions. And show up.

Let me take you back a few decades – back to when I was graduating from college in the midst of a prolonged recession. Many of my classmates were taking any job they could. They just wanted to get a foot in the door somewhere, anywhere. And many were even opting for unpaid internships.

Well I couldn’t afford to do that. Even if that meant being a bit more creative and scrappy to find that first full-time job. The problem was, I didn’t know enough about the job market to chart my own path. So, I did what I would do over and over again in my life to make an informed decision: I asked questions. Of anybody and everybody.

If the opportunities I want are not coming to me, I’ll have to create them for myself.

I went out in search of people to network with who could help me find those interviews. I was looking for an “in” or an advantage anywhere I could find it. So I started looking close to home – the Tee Pee restaurant, where I had been waitressing throughout college. It was a natural place to network because of the constant stream of people coming from all over the country to enjoy delicious mexican food.

I started with a customer who had been a regular over the years. We always chatted as I was getting him his dinner order, but I never asked him what he did. I decided it was time to find out after he asked me what I was planning on doing after graduation — that dreaded question.

“What do you do for a living?” I asked.

He told me he lived in Los Angeles and came to Phoenix regularly for work. He managed product placement for Anheuser-Busch on movie sets.

Now, being a college student, I knew what Anheuser-Busch was. But what was product placement exactly?

“Where do you place beer products?”

“On movie sets. We film a lot of movies in Arizona.”

“I could definitely do that! Can you get me an interview?” I said, half kiddingly – but not really.

Sure, enough he came through. One interview in the books! I just had to get to Los Angeles which was easy enough.

I was feeling pretty confident. What was once something I didn’t know how to tackle, getting the interview, actually was fairly easy to line up. One step at a time. So, I continued to scan my network, inside and outside of the little restaurant. If I was going to be in Los Angeles for an interview, maybe I should line up some other interviews. And visit other cities too.

Another frequent pair of customers was a couple from Illinois who owned a vacuum cleaner business. They invited me to interview with their company – which would ultimately mean a move to Chicago. Chicago could be a fun option!

“What kind of roles are in your vacuum cleaner company?”

“Marketing could be a great start for you.”

The idea of marketing piqued my interest for sure. And it also solidified the fact that I knew I wanted to move to a big city – Los Angeles, San Francisco, Chicago, Boston, or New York – to start my career. I didn’t exactly see myself marketing vacuum cleaners, but I didn’t want to rule anything out. Things were falling into place, and I started mapping my path forward.

Decide on a direction. Set your course. But be open to changing it if necessary.  

I put together a list of every company I could imagine working at, as well as every place someone could connect me for an interview. I said yes to all. I assembled all of my leads and I started sending out letters and making phone calls, this was before email was a thing believe it or not. I told everyone who responded to my inquiries that I would fly myself out for a meeting. That I had researched their company extensively (and I did). I pitched myself hard. I knew I was not only a hard worker, but that I was sure I could contribute and make a difference.

Before long, I had seventy potential interviews lined up – in all of my wish-list cities! They were entry-level positions at a variety of companies, from consultancies to financial service providers to publishing.

But I didn’t stop there. As I embarked on my “tour,” when people asked about my plans (and they always did), I told them which city I was headed to next.

“My third stop is Chicago. I’ve never been there so I am very excited.”

“What are you doing there?”

“More interviewing. I am on a tour getting in as many interviews as possible over the next month. If you know anyone that is looking for a smart, hard-working college grad, I am the person.”

Just by putting myself out there, telling people what I was looking for – most were eager to help. I was amazed at how many people started opening up their rolodexes.

“I do know someone in Chicago. Let me give her a call and see if her company has any entry-level positions open.”

I soon lost count of how many interviews I had done over the course of that month, but it was close to 100 in total.

Still, there was one place I wanted to work at above all the rest. It was a New York publishing company whose product I really admired.

Fortune magazine.

Unlike many of the other companies I sent letters to, I didn’t have a referral contact at Fortune, but I didn’t let that stop me. I looked at the masthead and went straight to the top. Marshall Loeb. Managing Editor of Fortune Magazine. A major figure in the New York and national publishing scene.

I figured it couldn’t hurt to ask for an interview — what’s the worst that could happen?

In fact, I’ve found that the most certain way to get what you want is to ask, directly and explicitly. And ask yourself that question too if it seems a bit scary. The worst that could happen is rarely that bad.

In all the letters I had sent to prospective employers, I simply asked for an interview and a job, but I added a more personal touch to my Fortune letter, sharing how his magazine had helped me understand finance, my minor in college. I explained how Fortune really helped to demystify many of the challenges I’d initially had with the subject in my classes.

Then, I got a letter back! Marshall had responded thanking me for writing and proposing that if I was ever in New York, I should get in touch. He would be excited to meet me.

Wow.

That added New York City to my list of places to visit. The last stop on my US “find a job” tour.

Btw, you may be wondering how much this “investment” cost me. Great story there as well. When I thought about taking this month-long adventure to figure out what I wanted to do, I worried I may not be able to afford all the stops. I called a travel agent and ran through my five-city itinerary with her: Los Angeles, San Francisco, Chicago, Boston, and New York. $472 total. That’s right. Total. Still a lot for me, but much less than I expected. And looking back, one of the best investments I made in myself.

Some things are meant to be. And you never know if they are until you set out toward your goal. Take those steps.  

Fast-forward to a cold January day in New York, 1989, as I walked along Sixth Avenue to the famous Time & Life Building. I pushed through the revolving door into an overwhelmingly awesome lobby of glass, marble, and stainless steel, hung with enormous works of art.

I hesitated. Could I really go through with this? That little doubting voice was chiming in in my head. And the fear was rolling in. I hadn’t actually arranged an interview at Fortune, but I did have my letter from Marshall Loeb in hand. Suddenly, it felt like an impossible long shot. I took a deep breath.

Show up. What’s the worst that can happen? You’ve got this.  

I got in the elevator, rode up several floors to the Human Resources department, and went directly up to the receptionist.

“Hello. I’m interested in a job at Fortune. I am here to see Marshall Loeb. ”

She looked at me skeptically.

“Do you have an appointment?”

“No. But I have a letter from him though.”

A woman standing nearby had heard our exchange. She came over and introduced herself as the Head of Human Resources. She glanced at the letter. Maybe she had seen a few like it?

“What Mr. Loeb meant was that you should get in touch and make an appointment for an interview if you were planning to be in New York.”

Although she was saying “No,” what I heard was “Maybe.”

“Maybe there is another opportunity with one of the other magazines? I would love to work here. I am leaving tomorrow. Would it be possible to interview somewhere else for one of your openings?” I didn’t turn to go. I just stood there. Right in front of her. Hard to ignore.

I had become an expert in asking for what I wanted. An interview.

There was a pause. Then she remembered something. “There really aren’t any openings at Fortune right now, but there is one at Time. It’s in the circulation department. For an executive assistant role. Would you be interested in that?”

Now she was saying “maybe,” but I was hearing “yes.” I had only a vague idea of what circulation was. It wasn’t Fortune Magazine. It wasn’t Marshall Loeb. But if I could work in the building, in New York City, maybe I could meet the Fortune people and eventually get hired as a writer.

Have a goal but also be open for adjustments.

“Yes! I would be interested in interviewing!”

I am forever grateful to that kind woman from Human Resources.

She escorted me to an office on a different floor. There she introduced me to Brooke McMurray, who was looking for an executive assistant. In my interview, I told Brooke my whole story—about how much I liked writing and reading Fortune, my letter to Marshall Loeb, my seventy interviews on my cross country tour. My authentic story.

Brooke listened patiently. I can only imagine how I came across.

When I returned to Arizona, I had a voicemail waiting. Many voicemails. And letters. Offers! Including one from the last place I interviewed. Brooke wanted to hire me as her assistant! I had landed a job in the city that was my top choice and in the building I wanted to be in. Not Fortune, but close enough. And working for a person who I believed could support me as I supported her.

Turns out, I picked right. One of the best bosses I ever had.

I’ve seen a few challenging moments since my own graduation in 1989, and when you are in the moment, they certainly feel like unmatched havoc and uncertainty. And perhaps, 2020 may feel a bit like this for some of you.

But don’t let the events of this past year keep you from moving forward. Tomorrow is a new day. Your job now is to be open to possibilities. Be inquisitive. Ask anyone and everyone for advice, for leads, for connections. Be a sponge. Absorb as much knowledge as you can to help set you in the right direction.

Create the opportunities you want. Don’t wait for them to present themselves either. Take the risk. Write that email, send that DM, or make that cold call to pursue that possibility.

Find what you are looking for. It’s out there.

And know that I believe, and so do many others, that YOU can make a difference. And you can find what you are looking for.

It’s your turn now to get out there and live undaunted!