Squashing the Blame Game


I’m quite careful about dispensing unsolicited romantic advice. But when I sit with entrepreneurs who are just starting out, I find I have a lot to say about what makes for a good relationship. My husband Patrick and I have been married for nineteen years, together for twenty-five, and at some junctures, we have both been entrepreneurs at the same time.

Marriage and/or starting a family is stressful under the best of circumstances. Starting a business is stressful under the best of circumstances. Put them all together and oy vey! An entrepreneur’s hours can be long, the uncertainty is ever-present, and many founders have their financial well-being as well their identities wrapped up in a company’s success, which raises the stakes. I’ve been on both sides of the divide. I’ve been the partner standing in the supporting role, cheering Patrick on in his ventures, and I’ve been the one who has relied on him to cheer me on when I needed it, and to ground me in reality when I needed it.

In any venture, just as in any marriage, things can go very wrong. Partners can feel burdened by carrying the brunt on the home front, and feel as though they’re isolated from what’s going on in the business. It can feel as though the entrepreneurial partner rarely makes time for them, and their needs—maybe even their careers-- take a backseat. On the other side of the divide, entrepreneurs can feel that they have to protect their mates from some of the pressures and fears they feel. And in any case, even if they share their greatest worries, many still feel they have to bear them alone.

Patrick and I have been through some extremely hard times together, including a failed business, a near-bankruptcy, and a health crisis. When people ask me how we weathered it all, though the answer is multi-layered, there is one simple premise underneath all we’ve done right: We don’t blame each other. Blame is a toxic word. Blaming your partner is derisive, and when the chips are down, you want to be about building each other up and not tearing one another apart. Blame comes in only when empathy is lacking. Blame means you’re more interested in pointing fingers than in linking hands to figure the way forward.

If you’re in the thick of stress surrounding a startup and feel the urge to blame your partner, stop and close your eyes. Regardless of whether you are the one starting the company or the supportive significant other, think about what your partner’s experience has been like, what’s been hard for her, and why. Stay there. Linger there. Then, invite her to tell you about it, and really listen. Stephen Covey famously said “Seek first to understand, then to be understood.” Seek first to understand. For where there’s understanding, there’s no room for blame.


Creative Giving at the Source

Around this time of year, it’s only natural for us to think a lot about consumerism. Between Black Friday and New Year’s, we have a whole lot of shopping and returning to do. As a businessperson, I’ve long been tuned in to trends, and it delights me that more people are wanting to spend money on something they feel makes the world a better place. Fairs abound where you can spend your dollars on a gift that does a social good, like chocolates from Theo’s Chocolates, or a Mushroom Farm Kit from Back to the Roots. REBBL super herb beverages, the company I run, was born out of wanting to solve a serious problem—that of human trafficking. I wasn’t involved with REBBL at the time of its inception, but I love telling its remarkable story.

The non-profit Not for Sale, with Dave Batstone as its founder and president, has a vision of eradicating human trafficking in our lifetime, including the slave and sex trade. This is an uncomfortable subject to talk about, in part because the problem is so enormous.  Human trafficking impacts thirty million people. That’s just hard to wrap your mind around. Eighty percent of them are women and girls. Human trafficking is the fastest-growing illegal activity in the world.

In 2011, the geographical area of concern for Not for Sale was the Peruvian Amazon. Though rich in natural resources, because the area is so remote, and cut off from basic infrastructure, the communities there were struggling to meet their basic needs, and were vulnerable to exploitation. The problem was clear, but the solution wasn’t immediately so. What could Not for Sale do to help create jobs in this area?

The non-profit convened a summit called the Montara Circle, bringing some of the greatest business minds together to come up with a solution. The diverse group of people in attendance included a professional baseball player, an agronomist, an engineer, and investors. Splitting them into teams, Dave boldly said “we will fund whatever project is voted to be the best one today.” (He prayed that the best idea would actually be a good idea!)  REBBL—a beverage using the native super herbs from the area—was the winning product idea. The concept was that the herbs would be bought directly from the indigenous community, providing them with a living wage for their crops. With the hopeful growth of REBBL, the community would no longer be vulnerable to trafficking.

Next the leaders of Not for Sale needed a brilliant product innovator to create a drink that consumers would flock to—for without customers, there was obviously no point. Palo Hawken, one of the best innovators in the beverage business, agreed to work for REBBL, but only if he could make a drink like no other. And he did. REBBL, which stands for Roots Extracts, Berries, Bark and Leaves, is Righteous Plant Alchemy—a creamy, indulgent coconut milk elixir made from the best of the Plant Queendom. We’re educating people about super herbs like turmeric, with its antioxidant properties; and herbal adaptogens like ashwagandha, which helps your individual body adapt to stress. While Peru was the first vulnerable area for REBBL to source ingredients from, it has since expanded to other corners of the globe, like Sri Lanka and Madagascar.

By supporting a living wage, REBBL is able to help insulate communities against trafficking attempts. REBBL is dedicated to helping our grower communities meet basic needs like health care, clean water, and education (especially girls’ education). And REBBL also gives 2.5% of its net sales back to Not for Sale, so that the non-profit’s great work can continue. Every bottle makes a difference. That’s why we like to say that REBBL is more than a drink—it’s really a movement. It goes without saying that I’m proud to be a part of it. But just as exciting is that I increasingly learn of founders creating companies like REBBL each year, companies that are borne out of a desire to solve the social problems of our age. And maybe we just will. 

A Bookworm’s Holiday

It’s been said that people often give the gifts they want to receive. Perhaps that’s why I’m so often attracted to bookstores when I’m doing my holiday shopping. As my family will attest, if I get a book for Hannukah and one under our Christmas tree, I couldn’t be happier. 

I’ve collected a list of my favorite, worn and well-loved copies of books that have altered or furthered my thinking in some way, and that I would recommend for any entrepreneur. While some are business books, and some are specifically about my area of business (food), others have a much broader appeal. Some have been around forever, and some will be.   

·        The Founder’s Dilemmas, by Noam Wasserman. Quite simply, this is a groundbreaking book. Based on extensive research, Wasserman chronicles founders’ most common mistakes and why they make them.

·        The Hero’s Journey, by Joseph Campbell. Everyone should read this book no matter what their profession or life story. It’s mind-blowingly thoughtful about the essence of life.  It also happens to be unbelievably on point for what the entrepreneurial road holds.

·        High Hanging Fruit, by Mark Rampolla. Full disclosure: Mark is a friend and a REBBL board member and investor, but when you read his book, you’ll see the appeal for yourself. He’s a descriptive writer who really makes you feel what it’s like to start a beverage company, and then takes you through the nuts and bolts of building it.

·        The Lean Startup, by Eric Ries. An unbelievably practical book that changed—and improved—the way companies come to life.

·        Raising the Bar, by Gary Erickson. Gary, Clif Bar’s cofounder, was one of my greatest mentors, so it’s no surprise his book makes my list. He showed me what it looks like to run a business thoughtfully and with a larger purpose, and his book does the same for all readers.

·        Daring Greatly and Rising Strong, by Brené Brown. I couldn’t choose just one of Brené’s books. She powerfully captures the importance of vulnerability, of what it means to fall in the arena and get back up again.  

·        The Omnivore’s Dilemma and Cooked, by Michael Pollan. Though they are not business books, Pollan’s works are crucial to understanding the food world and how people think about their relationship with food. As I am in the business of food, I feel qualified to say that his contribution to our field is invaluable.

·        Blessed Unrest, by Paul Hawken. Hawken is a visionary who explores the social and environmental change movement.  He helped me understand what it takes to create change and build a movement.  As we chart new territory as entrepreneurs, this is an insightful read.

The Birth of a Book


Yesterday, December 6, my book Killing It was born—officially published! And, well, wow.

It’s cliché to say it’s been a journey, but there’s no better word for it. Though I researched all the proper publishing steps before embarking on writing, I learned that publishing a book is about so much more than getting words down on a page and sending them to an editor. It means thinking deeply about your experiences to find the insights that you believe are worth sharing, those pieces of wisdom you hope can help others. I learned that writing a book will test your belief in what you have to say; you have to trust that it will resonate with readers. Writing a book is about determining that you are ready—really and truly ready—to mine your defining moments, even the hard ones, and make sense out of them. Writing a book means you’re ready to share your story.

I always knew that my struggle with an eating disorder was a critical chapter that I’d need to write about, and that made me nervous. I also knew that the story of Blue Sky—a company my husband and I so deeply believed in, a belief that took us to the brink of financial disaster—would need to be in the book. The idea of writing about Blue Sky, too, made me nervous. While my closest friends and family knew about these experiences, many other people in my life didn’t—to say nothing of the people in the general public who I’d be sharing them with.

But I was ready. I had to be, or it never would have worked. What I found was that the process of examining these experiences and finding meaning in them that could help others was healing. It was also invaluable and validating to interview other entrepreneurs for the book, and to see patterns and similarities in our stories. I saw firsthand how eager entrepreneurs were to talk and take a deep introspective dive themselves. Many said things like, “You know, I haven’t thought much about that before,” and interviews that were slated for half an hour went much longer. There were entrepreneurs I told about the book who revealed that they, too, had struggled with eating disorders and other demons they’d previously been too ashamed to talk about. The book gave me the opportunity to connect with kindred spirits who truly understood where I’d been, and vice versa.

With the publication of Killing It, now that conversation gets to grow. And that—much more than having my name on a book—is what feels most notable about this birthday. I hope that my story will inspire others to share their own experiences, especially the hard stuff. Being an entrepreneur can feel lonely, but it doesn’t have to. So, let’s talk.



Is your ecosystem healthy?

It’s never sounded quite right to me when people talk about finding balance in their lives. Balance conjures images of a produce scale, or a teeter totter, and life just feels too, well, messy, for that metaphor to work for me. I’ve always preferred the image of life as an ecosystem, a complicated, interdependent network of factors that are constantly in motion, constantly adjusting and adapting to delicate shifts in the landscape. A healthy ecosystem is foundational to everything we build on it. If it weakens, the ground can flood, or sink beneath us.

For entrepreneurs, assessing your ecosystem requires a deep and honest dive into all parts of your life. When you ask yourself these questions, don’t give the quick, instinctive answer. Give the hard one.

Are you getting good medical care?

Self-care starts with a competent medical care professional in your corner. Serious athletes wouldn’t dream of pushing themselves to the limit without a doctor’s help to make sure they’re gunning it in sustainable ways. As an entrepreneur, you are likely gunning it, too. Is your health holding up? Your heart? Your lungs? Your cholesterol? Your blood pressure? Your weight?

Do you have someone to help ease the mental burden, like a therapist or consultant?

Once your body is taken care of, it’s time to turn to your brain. Someone skilled in helping you manage the pressures of entrepreneurship is a key member of the team. Jeffrey Hollander, who is most famous for founding Seventh Generation, said, “I’ll always be a relatively good customer of my therapist because I know there’s always more I have to learn. I never feel I’ve learned all I need to know about having a healthy relationship to my work.” Can anyone truly say any different?

Are you on full throttle all the time?

No one can push themselves to the limit all the time. It’s just a matter of time before something breaks down, be it your health, your relationships, your sanity, or your business. Take stock. After an intense push, is there time for recovery? Is there enough of it? A cyclical pattern of rest and activity, rest and activity has driven human endeavors far longer than your company’s been around. And caffeine and—in bleak cases—drugs, can only stave this natural rhythm off for so long.

Do your highs and lows look like a mountain pass, or gently rolling hills?

Hint: You want the latter. If you go from being ecstatic over a great review or investor interest to despondent over a complaint or bad earnings report, you will be exhausted by the ride. No one can manage the turbulence of a mountain pass for that long. Rolling hills will work, though. Or even better, a flat meadow.

Who are your people? Are you getting enough time with them? Are they getting enough time with you?


Whether you are married, have children, have a significant other, or have good friends, know that you need people. The people in your life—outside of your work—have a key role to play in grounding you, in reminding you that you are more than your business, and in helping you unwind. Are you seeing enough of them to be sustained? And are you seeing them enough to sustain them? You cannot take the people in your life for granted, just because you’re a busy entrepreneur. As every morality tale from A Christmas Carol to “Cats in the Cradle” has reminded us, those people might just not be there if you turn your back for too long. 

The Way Forward: Business

There’s no point in mincing words. I was—and am—devastated by the outcome of the American election. The past week has been a flurry of tears, of being comforted and comforting others, of wondering how we got here, and where to go next. I’ve come out of the fog perhaps earlier than some others, and want to use my blog today to tell you why.

When I went to undergrad in the 1980's and studied business, I felt like I was selling my soul. I had always been committed to helping progressive causes and to social justice. I saw myself as a social worker, a public school teacher, perhaps even an activist. The practicalities that led me to look toward a career in business also made me feel like I was turning my back on my values. My dearest childhood friend and partner in progressive idealism even said, “Shame on you” when she heard I was going to business school and refused to speak to me for years afterwards. Over time, I’ve seen that not only was I wrong about business to begin with, but business itself has changed. More and more people have gone to business school or started businesses precisely because they want to see positive change in the world, and see business as the most strategic way to achieve it.

Some say it started with Ben and Jerry’s ice cream, or The Body Shop—companies that performed well and did good at the same time. Since the 1980s, the moral conscience of business has grown, and grown, and grown—and as we look toward a next few years with a morally questionable leader at the helm (who is, among other things, a climate change denier) business could provide the bright beacon of hope we’re all looking for.

Examples to warm your heart and ease your anxiety:

·        OSC2. It stands for One Step Closer to an Organic Sustainable Community. It’s a group of business leaders who are committed to tackling the toughest sustainability issues facing our planet. The focus of the day: compostable packaging and climate change initiatives.

·        B-Corps. To qualify to be a B-Corps, companies must meet high standards for environmental, social, and legal accountability. They must prove a desire to “use the power of the markets to solve social problems.” There are nearly 2,000 B Corps in 50 countries, and covering 130 industries. This is a growing global movement, one that aims to make business known as a force for good.

·        Hundreds of do-good enterprises led by smart, purpose-driven individuals. In the course of writing my book, I got to talk to people like:

o    Julie Schlosser, former Fortune editor and cofounder of Altruette. Altruette makes charm bracelets to empower girls, wherein each charm represents a different cause—and money is donated to that cause.

o   Kirsten Tobey and Kristin Richmond, cofounders of Revolution Foods. They started their company—which is committed to bringing healthy foods to school cafeterias—while getting their MBAs at Haas. 

o   Rip Pruisken and Marco de Leon at Rip Van Wafels. These young men bring non-GMO, high-quality ingredients to their snack food, but also have as one of their marquee values that they “don’t let our ego stand in the way of the truth.” Good advice for today’s leaders.

And don’t doubt that I’m putting my money where my mouth is. I’ve made a point throughout my career to align my ethical values with the work I’m doing. And I’ve been fortunate to be a part of three remarkable companies that are doing good in the world:

o   Clif Bar. This was one of the first companies to show me that you could have multiple bottom lines, and that we are as accountable to the environment as we are to our consumers.

o   Plum Organics. This is a company committed to helping kids develop a lifetime love of healthy eating.

o   And now I’m with REBBL, which is committed to eradicating human trafficking both by giving 2.5% of all profits to our nonprofit partner, Not for Sale, and to eliminating the sourcing issues that contribute to trafficking.

There’s a lot we can do, everyone. Even if you are not remotely interested in business, we can lead a revolution with how we spend our dollars. We can support good businesses and look there to find our moral leaders, in the absence of political ones. 

On Leaving With Grace

This week has been very emotional for Americans, and for some of us, nothing short of heartbreaking. But regardless of your politics, you have to admire the incredible grace with which Hillary Clinton conceded the race to her rival early Wednesday morning, after the most bitter and hard-fought campaign in memory. She wished her rival success as the new President and she expressed gratitude to her millions of supporters. She showed the leadership and grace for which many millions have come to love her.. Rather than let any hint of revenge or bitterness take root, she reminded everyone that “Our constitutional democracy enshrines the peaceful transfer of power “We don’t just respect that. We cherish it.”

At the same time, she held true to her values—some of which have appeared under siege during this ugly election cycle—noting that our constitution also “enshrines the rule of law; the principle we are all equal in rights and dignity; freedom of worship and expression. We respect and cherish these values, too, and we must defend them.” She ended on a somber but hopeful note saying: “My friends, let us have faith in each other, let us not grow weary and lose heart, for there are more seasons to come and there is more work to do.” 

I was moved by her humility and strength, as I’m sure many were, and it also felt to me like a familiar scenario writ large. When one has to leave the company they love, the company they’ve built; how do they do so gracefully? I watch this play out in business all the time, where a founder has difficulty leaving ego aside and seeing the signs everyone else can see: that he’s no longer the best leader for the company. The advice I commonly give on the subject is:

·       Have an exit strategy from the outset. Under what circumstances would you leave? How will you recognize when those circumstances exist?

·       How do you feel going into work every day? How do you feel when you imagine not going in? I recognized it was time for me to leave Plum when going to work felt like drudgery day in and day out, and the prospect of not going in felt like freedom. Naturally, everyone will have bad days or even weeks. But if those bad days stretch into months, there’s a problem.

·       Are you what the business needs? Do more objective voices think so too? There’s no shame in recognizing that while you were fantastic for a certain stage of the business, it will do better now in someone else’s hands. If you think you’re the right person to stay the course, then ask your board or other objective parties the same question. Be careful not to only ask those you’re close with and who are attached to your staying. Your departure will be hard for them, but that doesn’t mean you shouldn’t go. Always ask, what’s best for the business, not what’s best for you.

·       If you go, go gracefully. A scorched earth approach will leave you with personal regret and, likely, a few enemies. Look at it like sending a child off to college. It’s bittersweet, but clinging too long or making the goodbye too painful doesn’t change the inevitable—it just makes it more difficult for everyone.

·       Take care of yourself. Leaving a company that you’ve founded or been at the helm of is a big deal and can make for a difficult adjustment. Make sure the people in your life understand this and give you the support you need.

There’s a song in the musical Hamilton called “One Last Time,” wherein George Washington explains how his not running for president again will teach a nation how to say goodbye:

 “If I say goodbye, the nation learns to move on.

It outlives me when I’m gone.” 

            Whether politician or businessperson, this is a pretty powerful legacy to leave.  

Parenthood and Entrepreneurship: Yes You Can

Typical advice to entrepreneurs has been “don’t have kids when you’re starting your business.” Or “If you start a business while your kids are young, make sure your spouse or partner can be home with them.” I reject the notion that parenthood and entrepreneurship are somehow diametrically opposed and that unless you’re a superhero, both are not available to you. Instead of presenting this as an either/or dichotomy, let’s talk more honestly about how to do both. Over the past fifteen years, I’ve given an inordinate amount of thought to the issue in addition to having lived it myself. Here are five key things I’ve learned:

1. Be who you are. You might not be the kind of parent who wants to go to every single soccer game, PTA meeting, or playdate. Now read carefully: Plenty of parents miss many of these events and are great parents. They bring other things into their parenting, things that feel more authentic to them and show their kid who they are. I threw myself into full-time parenthood when I left Plum, only to realize what I knew all along: focusing on home life exclusively wasn’t for me. I love my boys and they know it—I don’t need to be at every class party to prove it.  

2. Take stock. Identify what your family needs to thrive, and use that as a touchpoint. My friend and REBBL investor Mark Rampolla said that early on when he started Zico Coconut Water, he and his wife agreed that Mark’s physical health, their marriage, and the emotional well-being of their kids were not things they were willing to gamble with. They kept coming back to these touchpoints in difficult moments, and it helped guide their way. Are you getting enough time with your kids to feel nourished? Are they getting enough time with you to feel nourished? There was a time when I recognized I was off-kilter, and that it was because I wasn’t seeing my boys enough. That’s when you need to adjust.

3. Build a team. No one does either work or parenting alone. Make a task chart with your significant other, and figure out who will do what and, if you’re able, what you can outsource. You need a deep bench, one that might include neighborhood parents, family, or friends. The same is true for the workplace—do you have people in place who can take over so you can take off to attend an important soccer game, or go on vacation? And do you step in to help them when they need to do the same?

4. Practice presence. It takes a lot of discipline to live in the moment. I used to have an incredibly tough time with this one. I would think about work non-stop when I was at home. I’m still trying to get better about this, every day. Try developing a ritual to leave work at work, whether it’s writing down things you’re worried about before you head home, or meditating in the driveway before you come in the house. And practice putting that mobile device away. Kids will watch what you do instead of just following what you say.

5. Change the culture. Both men and women need to have the conversation about how and where work fits into a full life. Parenting vs. work has been a topic among women for decades, but men need—and want—to be in on it, too. Men need to keep stepping up and women need to keep inviting them in. You may not always agree with how the other is getting it done. However, if it’s getting done, let go of judgement.


Why Time With Friends is a Must for Entrepreneurs

“I know it stinks, but I just don’t have time for my friends right now.” I hear this constantly from entrepreneurs who are in the thick of starting or running their business. It sounds reasonable enough. When you’re slammed and have to make tough choices, something has to give. You have to prioritize your kids, your partner, your sleep. But you also have to prioritize your mental health, and it’s very difficult to be in your right-mind when you don’t have your buddies reminding you to stay there. I know from experience just how difficult it is to make time for friends when it feels like you don’t even have time to brush your teeth. But here are five of my strongest arguments in support of friendship—and I encourage you to look at this list every time a friend asks to meet for a walk or a drink. Then, whenever humanly possible, say yes!  

1. Friendship is good for your business. You are likely spending most of your time amongst people who are just as swept up in your business as you are. You need the viewpoint of outsiders, those who can look at your business model or a tricky problem in an unattached way and give you a completely different spin on it. (But don’t be a bore and only talk about your business! Your friends are trusted points of view, not market-research subjects!)

2. It helps maintain your full identity. As an entrepreneur, you must constantly remind yourself that you are not your business, that there is a place where your business ends and the rest of you begins. Your friends can bring out the you that is a kick-ass basketball player, expert chili-maker, or crisis-counselor extraordinaire. They can remind you of the facets of your personality that existed long before your business, and will be around long after. Don’t underestimate how important this is.

3. It helps heal you. Friendships have been connected to longevity, longer survival rates from cancers, lower stress levels, and more. Your business is nothing without your health, and friendship is good for your health.

4. It forces you to face reality. When I was at my lowest but in a fair bit of denial about it, it was my friends who said, “Sheryl, what’s going on? You’re not yourself.” They would not let me evade them. They didn’t care about my business, they didn’t care about whether I drove a new Tesla or a beat-up truck—they cared about me.

5. You’ve learned this lesson before. Remember when you were obsessed with that guy/girl when you were fifteen and you dropped your friends to spend time with the target of your raging hormones? Remember how much you regretted it after the infatuation ended? You’re a grown-up now. Don’t make the same mistake with your business. Because this phase of your business will end—you want to be sure your friends are there afterwards.


6 Ways to Find Your Business Tribe


There is a uniquely warming experience about looking around at a group of people and knowing that they “get” you. I notice this with football fans who are either hugging in ecstasy or consoling one another, depending on the Sunday. I see it too with groups of young parents who can signal to one another with just a look that they have spit-up on their shirt. It’s a feeling of belonging, yes, but also of support and honesty. It’s a feeling that entrepreneurs need to be proactive about cultivating—because there’s no jersey or spit-up stains that signal “Hey! I’m one of you!”

All professions can benefit from solid support systems, but in the entrepreneurial world it’s particularly important. If you’re a founder, there’s a tendency to feel like you need to project confidence, all the time, no matter what’s going on in your business or in your life. You have to be the boss, inspiring people to work for you or invest in you, or to buy your product or service. But you also have bad days—sometimes really bad days. And you have moments of doubt and uncertainty. You might not feel like you can burden your significant other with it—again—and she or he might also not have the inside knowledge to really get it. Connecting with a support system made of people who’ve been there not only allows you to take some of the excess air out of an overflowing tank, but it can offer you insight and perspective that you may simply be too close to see. Here are some ideas for connecting with your tribe in a meaningful way.

1.      Network with authenticity. Don’t make connections just to make them—meet people and ask them questions because you’re genuinely curious about what they do and how they manage. Build a special relationship or two out of your networking efforts, or form your own group out of those you feel a connection with.

2.      Be reciprocal. If you find a kindred spirit whose advice or sympathetic ear you often seek out, be sure you’re lending your own in kind. 

3.      Join an organized peer-to-peer group like Young President’s Organization or Entrepreneur’s Organization. These groups are known for how seriously they take confidentiality. And confidence in privacy is imperative.

4.      Be real. I have what I call the Great Tribeship Test, which is really a question: Would you cry in front of that person or group? I’m not saying you need to bring the tissues to every meeting, but do consider whether you feel you can be vulnerable. 

5.      Don’t surround yourself with yes-people. There is a place for empathy and cheerleading, and it can coexist with criticism. If your tribe is only made up of people who think you can do no wrong, you are missing the tribe’s potential.

6.      Invest in a professional. There are ever greater numbers of therapists who specialize in business issues, and life coaches who have seen it all. Even if you think you can’t spend the money or time, consider it. Your business will not make it if you don’t remain healthy. I believe every founder and every CEO should have a therapist or coach, and know plenty of experienced entrepreneurs who swear they will never do without one again.  

Five Questions to Help You Determine Whether or Not You Need (or Want) a Cofounder


The allure of the cofounder is easy to understand. Why go the hard road of entrepreneurship alone when you can have a partner-in-crime? But for every Ben and Jerry out there, there are dozens of partnerships that have broken up (Jobs and Wozniack, Allen and Gates). Notice I didn’t say failed. Many partnerships—including my own with my former business partner, Neil—can be incredibly productive and fruitful while they last, and their ending just represents a natural evolution of the company, not a tragedy. But just like marriages, cofounder relationships can have devastating fall-out when they come undone. All the more reason to proceed with caution at the outset.

In those first heady days of a new business venture, it’s easy to imagine that you and your cofounder will always see each other in a rosy light. After all, if you weren’t an optimist, you wouldn’t be an entrepreneur. But asking some deeper questions before the wild ride of starting a company begins will help you navigate this potentially rewarding, but extremely complicated relationship.

·        How well-suited are you for the cofounder relationship? For instance, how do you feel about sharing control? Or even ceding it?  What brings out your best self and ideas? Is it collaboration or solitude?

·        Do you have expertise in the industry in which you want to start a company? If not, it may be crucial to look for a cofounder, someone who will be as invested as you are but can make up for the gaps in your knowledge.

·        How well do you know your potential cofounder? Just as with marriage, committing to someone too early can be a death knell for a business partnership. It’s easy to get excited about smart, cool potential collaborators, especially if they are charismatic. But it’s worth taking the time to get to know someone you’re considering going all in with on a deeper level. What are their views of how to manage life in a startup? Do they think you need to be all-in, or do they believe it’s possible to have life outside of work? What gets on their nerves? Who are their favorite people to spend time with? Ask them questions as simple as how they like to spend their weekends. You’re dating, in a sense—these are all things you need to know.

·        Do you share a vision and values? Discuss what you both want out of your work, what you want to contribute to your industry and the world around you. Do you agree on the core leadership philosophies? Are you aligned on a mission? How much do you each want to work? How will you handle a situation wherein you feel one person is pulling more weight than the other? Hypotheticals often reveal values, so take the time to come up with scenarios and think them through together. 

·        Would another kind of support system be better for you? No one truly goes it alone in business—but perhaps what you need is a team of advisors, a mentor, or investors who can offer direction as well as capital. The question of having a cofounder isn’t an all or nothing choice. Consider all of your options before going forward.