Start, Love, Repeat

How to Stay in Love with Your Entrepreneur in a Crazy Start-up World


By Dorcas Cheng-Tozun

Read by Linda Henning

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A prescriptive guide to how to keep your relationship strong when there’s a start-up in the family.

The idea of starting your own business is exhilarating and inspiring. It’s one over 30 million Americans pursue. But being the significant other of an entrepreneur is not so glamorous. Boundaries between work and home disappear. Personal savings and business funds become intertwined. You can feel like a single parent as your spouse travels, works late hours, and answers calls and e-mails 24-7.You may even sacrifice a career or move your home for the sake of the business.

But there are strategies you can use to combat all this stress and uncertainty. Whether you’re new to the start-up world, or a long-term entrepreneurial partner, Start, Love, Repeat will help you understand exactly how a start-up affects your lives-and what you can do to build a happy and healthy relationship in the midst of the madness. Dorcas Cheng-Tozun has not only done extensive research, she has lived through the perils and pitfalls of being with an entrepreneur as the wife of the CEO and cofounder of successful start-up d.light. She offers clear-sighted, first-hand advice for any couple considering making the same leap. She further draws on interviews with other successful entrepreneurs and their significant others, executive coaches, marriage-family therapists, venture capitalists, and start-up authorities to provide practical insights and steps any couple can take to build a strong relationship while launching that dream business.



by Meg Cadoux Hirshberg, former Inc. magazine columnist, and Gary Hirshberg, chairman and former CEO, Stonyfield Yogurt

Spouses of entrepreneurs, rejoice: Dorcas Cheng-Tozun has thrown you a life raft. Cleverly organized according to the typical stages of a start-up (market research, strategic planning, etc.), Start, Love, Repeat looks carefully and closely at the intimate relationship dynamics that occur when a business enters the family.

As a writer and the spouse of an entrepreneur, Dorcas is eminently qualified to give voice to the spouse’s perspective on the concerns, struggles, and—yes—joys that typically occur in an entrepreneurial marriage, and she does so in clear and impassioned prose. My own entrepreneur husband and I often liken the spouse’s journey to riding shotgun down a curvy stretch of road. Usually the driver—the one in control—is just fine. It’s the passenger who feels sick.

When people start companies, they research the competition, market data, Small Business Administration loans, and the cost of office space. But they generally give little thought to how a business will affect their personal lives. The spouse may fret and worry a bit more about the insecurity of the venture for family, but generally both entrepreneur and spouse assume that they’ll muddle through for the “year or two” it takes the company to gain traction. When things don’t go as expected, and they rarely do, the cracks that exist in any marriage can grow into fissures, as the spouse’s resentment blooms into full flower, and the entrepreneur comes to feel unfairly condemned and misunderstood.

A close reading of Start, Love, Repeat will go a long way toward dissolving those resentments before they start to build. Dorcas writes intimately and with great nuance about her own experience of being in an entrepreneurial marriage, and also includes illustrative stories of many other entrepreneur-spouse couples. Throughout the book, she cites fascinating research concerning entrepreneurship, as well as insights from therapists and executive coaches.

A common romantic image of the entrepreneur is of an exceptionally daring person who sallies forth—alone—with persistence and determination to realize a dream. While there is some truth to this vision, the unspoken reality is that an entrepreneurial venture sucks the entire family into its vortex. Dorcas details that reality, and acknowledges its potential danger to the couple’s relationship. To better arm those who are along for this ride, she offers useful, practical, specific suggestions of actions the couple can take.

While Dorcas is sober about the challenges, she is equally clear about the tremendous potential upsides for a spouse in an entrepreneurial marriage. Much of it, she argues, is a question of perspective. She urges the spouse to consider: What is the opportunity in this?

As I opened page one of Dorcas’s book, I wasn’t sure I had much more to learn about the tribulations of marriage to an entrepreneur. First, I’ve been married to one of the tribe for more than thirty years. And as a former columnist for Inc. magazine, I had covered similar turf in my “Balancing Acts” columns for the magazine, as well as in my book For Better or For Work: A Survival Guide for Entrepreneurs and Their Families. Tearing through Dorcas’s lively manuscript, I found her insights to be powerful, useful, and true.

Dorcas quotes author Brené Brown, who wrote that “Vulnerability sounds like truth and feels like courage.” This is a perfect summary of Start, Love, Repeat. Dorcas’s courage in making herself exquisitely vulnerable by speaking frankly about her own experience is quite clearly in service to her desire to help others who find themselves hitched to an entrepreneur’s dream. The reason is simple. While the inevitable trials of an entrepreneurial marriage could have driven Dorcas apart from her husband, Ned, working through them has actually brought them much closer. “I don’t want us to be lucky,” she adds. “I want us to be typical.”

—Meg Cadoux Hirshberg

Ever since Meg’s book was published, I’ve advised every entrepreneur I know to read it with their spouse. It was the book I wish Meg and I had had when we got started on our crazy entrepreneurial ride growing our company, Stonyfield Yogurt.

Now I will have to add Dorcas’s important book to my list of recommended reading. While she aims her thoughts and research directly to the spouses of entrepreneurs, this book is a must-read for entrepreneurs as well. Dorcas’s insights into the entrepreneurial life and what is required of both spouses and entrepreneurs to survive and thrive on this journey should not be limited to spouses alone.

The essential quandary for entrepreneurial couples can be summarized this way: For a business to survive, the entrepreneur has to be all in, or the business doesn’t stand a chance. The intense focus required by this passion project, aka the business, can be in conflict with the entrepreneur’s passion for their intimates. Stimulated by the endless series of challenges, what feels to us entrepreneurs like a long series of sprints is often a lonely marathon for our mates.

I wholeheartedly agree with Dorcas about the importance of shared mission in keeping an entrepreneurial marriage alive. Meg and I found that our mutual commitment to growing the organic food sector helped get us through our darkest days with the business. Both spouse and entrepreneur must ask themselves and each other: What is our motivation? Why are we doing this? Ideally, the answer to that question can become a touchstone through the trials of growing a business.

Dorcas has great insight into the entrepreneurial personality, characterized by “that nagging yearning to start something.” She understands that the entrepreneur perceives stress differently from the spouse. What’s different, as Dorcas points out, is that an entrepreneur often perceives stressors as positive challenges. The spouse, not so much.

These and many other insights into the psyches of entrepreneurs and their spouses will not only give you tools you need to move forward and grow but will make you feel less alone in your struggles. Looking for a guaranteed good investment? Read this book.

—Gary Hirshberg


When my husband, Ned, and I were expecting for the first time, I told everyone we were looking forward to the arrival of our first human child, but not our first child. That distinction went to my husband’s latest and biggest start-up, which was conceived by Ned and several graduate school classmates just a few months after he and I married.

Our first child, also known as social enterprise d.light, has led to countless missed holidays and broken appointments; it has contributed to physical illness and emotional meltdowns for both of us; it even caused us to move to China for three years and to Kenya for seven months. Thanks to the demands of his business, Ned and I have had years-long disagreements about work-life balance, time management, and quality of life. We delayed any consideration about having real children until d.light was a little more grown up and independent. I have been in therapy several times and have even had to take antianxiety medication because of how deeply my husband’s start-up affected my personal life.

Today d.light is a thriving multinational business with hundreds of employees across five continents—an outcome neither of us would have predicted in its wild, roller-coaster first years. Worldwide, about 80 million people are using d.light’s solar products. Our lives have gotten a little easier as the company has matured, but the truth is that an entrepreneur never really stops being an entrepreneur. The challenges that we face as a couple, while morphing countless times over the past twelve years, continue to this day.

Along the way I kept hoping to find a resource or community of people who could explain the challenges of being with an entrepreneur and could tell me how to support my spouse’s dreams without sacrificing my own. More often than not, my search led me to broken relationships or failed businesses.

Determined not to be another one of those statistics, Ned and I fought for our marriage even when doing so affected his business and both of our careers—and the outcome has been mostly positive for us. I know we’re one of the lucky couples, as any foray into the lives of entrepreneurial spouses will quickly lead to stories of resentment, betrayal, and conflict. But I don’t want us to be lucky. I want us to be typical.

We tend to stereotype entrepreneurs as uniformly young and single, but the truth is that nearly 70 percent of business founders have spouses, life partners, or children—all of whom, whether they like it or not, are living the start-up life.1 Those who choose to be with entrepreneurs invite things into their lives they may never have wanted: financial instability, uncertainty, stress, and the nagging sense that they are always playing second fiddle to the greater lure of their partner’s business.

In American lore, the entrepreneur that has most captured our imagination is the Steve Jobs–Mark Zuckerberg–Jeff Bezos–Elon Musk type. Someone who walks that fine line between brilliance and nuttiness, between the present and a future few can imagine. Someone from a humble background who eschews tradition, beats the odds, and through a fortuitous combination of ingenuity, perseverance, and good timing becomes a multibillionaire who changes the way the world works.

You may be in a committed relationship with one of these entrepreneurs, and to you I say, Good luck. Hopefully the years of striving and sacrifice will all be worth it when you can no longer keep track of the number of zeros in your bank account balance.

But the vast majority of entrepreneurs are a little more earthbound. Yes, they are creative and passionate, hardworking and motivated, but they also likely come from middle-class or upper-lower-class backgrounds.2 They come from all different ethnic backgrounds and have varying levels of education. They have perhaps been gainfully employed for one or even two decades and may be around the age of forty (the median age of someone starting a first business).3 Their reasons for wanting to start their own business will vary, of course, but most likely the list will be topped by their determination not to work for someone else, to be the masters of their own fate.

Ironically, your beloved’s decision to be his or her own boss will likely impinge upon your ability to have full control of your life. Anyone who has been there knows that start-ups, at least at the outset, require what seems like a black hole’s worth of two finite resources: time and money. Never seeing your significant other who is obsessively working to get his or her business off the ground will deeply affect a relationship. So will not having a regular source of income while savings disappear and debts pile up.

Or, if your business is among the nearly one-quarter of new businesses that are co-managed by spouses, you are living and breathing the start-up life in every way imaginable.4 There may be no clear boundary between your work life and home life—which, over time, creates its own challenges in the relationship.

But even if you aren’t a co-preneur, it’s likely that you’re playing at least some role in your significant other’s venture. My roles in Ned’s multiple companies have ranged from envelope stuffer and proofreader, to circuit solderer and Santa-signature forger (more on that later), to human resources manager and director of communications.

Regardless of how involved you are in the venture, or how long you have been with your beloved entrepreneur, having a business in the family will affect you in innumerable ways—from your day-to-day schedule to your quality of life when you are old enough to join AARP. This book is for you.

This is the book I wish I had when Ned and I were preparing to say our wedding vows. I would still have married him, but understanding how deeply Ned’s professional choices could affect me would have given me the chance to build my support network, gird my loins, find a really good therapist, and do whatever else I could to ensure that the pursuit of his dream wouldn’t come at a cost I was not always confident I could bear. This book answers the questions that plagued me for years, from basic start-up information to relationship advice, including:

What are the typical challenges faced by the spouses and partners of entrepreneurs?

How can we minimize our financial risk before starting a new business?

Is it possible for entrepreneurs to have work-life balance?

How can I prevent my own identity from being subsumed by my spouse’s larger-than-life work?

Should we delay having children if we’ve started a business? Should we delay starting a business if we have young children?

Is it ever reasonable to ask my significant other to walk away from the business for the sake of our family?

The content of this book follows the same trajectory as a (hopefully successful) start-up, beginning with market research on who in the world these entrepreneurs are; due diligence on understanding what you and your marriage need to be okay; strategic planning approaches to make your relationship and family life work; and ending with that hardest of questions: When is it time to call it quits, either in the business or the relationship, and start over with a clean slate?

Each section includes recent research findings and insights I have collected from professionals in the start-up ecosystem—business school professors, investors, executive coaches, experienced entrepreneurs—as well as advice from top marriage-family therapists. I have also been privileged to hear stories from dozens of entrepreneurial couples. In their hard-earned experiences, which I share throughout the book, are some of the most valuable lessons of all.

No research exists on how many entrepreneurs’ marriages fail, but in one 2017 survey, 27 percent of business founders said that starting a company had negatively impacted their relationships and family life.5 Ask anyone who has been in the start-up world for a while, and they’ll tell you about the disproportionate number of broken relationships and divorces they’ve seen. Relationships, like businesses, take quite a bit of investment for them to last. They require our best energy and thinking, and our willingness to sacrifice and make adjustments. There may be only so much you can do to help your partner’s business succeed, but there is plenty that you can do to help your partnership succeed, come hell or high water, or yet one more hundred-hour workweek.

Several therapists I’ve interviewed have said that someone faced with challenging or unexpected circumstances should ask this most powerful of questions: What is the opportunity in this? Our willingness to see everything that comes our way as a chance to learn and grow and try something new could be all we need to keep ourselves grounded and our relationships thriving. My hope is that this book will help you find your opportunities—for yourself and the ones you love most.



Chapter 1: Meet the Entrepreneur

Chapter 2: Meet the Start-up

Chapter 3: The Entrepreneurial Life

Chapter 4: The Entrepreneurial Relationship


Meet the Entrepreneur

My husband, Ned, entered college thinking he might like to major in music. Then he decided to be pre-med. Then he considered astronomy. Then audio engineering. Then physics. Electrical engineering. Environmental science. Computer science. Each time his major changed, he reorganized his entire class schedule, frantically adding and dropping courses right before the registration deadline. He usually ended up with an eclectic grab bag of classes, all of which he was already behind in. He would pull several all-nighters just to catch up in his classes and then push himself at full speed for the rest of the term to get good grades.

Ned and I became friends in the middle of our freshman year. “You’re studying what?” I found myself asking him each quarter. “Why?” I was bewildered by Ned’s behavior. I had come into college knowing that I wanted to study communications and was proceeding in a straight line toward completing my degree.

“Doesn’t it sound fascinating?” he would reply. “I wanted to try it in case I want to be a doctor/scientist/astronomer/engineer/musician/person who does something cool.” Occasionally he shot back with a cheerful, “Why not?”

Watching Ned change majors and course loads more often than I changed my hairstyle drove me nuts. But I still fell head over heels for him, in large part because of his gentle persistence and infectious curiosity.

Yet some serious questions surfaced as I weighed our potential future together. What in the world would he end up doing after he graduated? Could he even keep a stable job? What would life be like with someone so lacking in focus and decisiveness?

The issue, we both realized much later, wasn’t that Ned lacked focus. The challenge was that he wanted to focus on everything, to understand a bit of nearly every field. He worried about missing out on something better if he spent too much time and energy in one area. He actually enjoyed the rush of serially dating and dumping so many majors and classes. (Fortunately for me, he had no inclination to serially date and dump humans.)

We both should have known he was going to grow up to be an entrepreneur.

When Ned eventually graduated, he had earned two separate degrees: one in computer science and another in environmental science. He promptly found a job as an audio software engineer. I felt relieved that he was finally settling down. He had a real, stable, well-paying job, and he was getting ready to make a lifelong commitment to me. The wild days of his youth had passed.

Then, six months later, Ned quit his job. He had been miserable, his soul slowly suffocating under the weight of silent coding, socially awkward coworkers, and organizational politicking. He had no idea what he was going to do next. But he knew he didn’t want to be an engineer.

Alarm bells began to ring in my head, triggered by everything my parents had ever taught me about being sensible. Ned should have been able to suck it up, I thought, to do what he needed to support himself and be a responsible member of society. Yet I was still madly in love with this unpredictable, unconventional young man. As someone who had always played by the rules, I admired Ned’s willingness to buck expectations and plunge into new arenas without a second thought. He seemed fearless, bursting with confidence and hope that he could find work that was interesting, meaningful, and fun.

But I also worried there was something seriously wrong with him. If we ever merged our homes and our bank accounts, his freewheeling, devil-may-care approach to life could very well screw up my orderly existence.

Ned wanted to do something creative with music and technology, and after a few months of brainstorming and experimenting, he and a couple of buddies decided to develop personalized children’s music. They composed and recorded their own music, and developed an algorithm that seamlessly inserted each child’s name into the songs. Their families fully funded the business. I did not put in a cent of my own money, but I contributed countless hours burning CDs (the height of audio technology in the early 2000s), sticking on labels, and stuffing envelopes.

Even then, I didn’t quite know what to make of Ned’s venture. Interesting, yes. Fun, yes. Perhaps meaningful for parents stuck on road trips with demanding youngsters. But I couldn’t imagine him becoming a personalized children’s music guru. Was he going to tour the country doing personalized concerts? What did success even look like in this industry? Most importantly, was he ever going to make any income?

By the time we got engaged a couple of years later, in 2003, Ned was on to his next business. He had realized the children’s music market couldn’t be profitable. The market was too niche, the distribution network too limited. Instead he was going to record and sell original mobile-phone ringtones.

I’m sure I gave him a look—one that has become quite familiar to both of us over the years. “They’re huge in Europe and Asia,” Ned explained defensively. “People there spend a ton of money on ringtones.” He tried to convince me that even if I was content with the “Trio” and “Samba” ringtones that had come with my little flip cell phone, millions of other people in the world weren’t.

You may be wondering how Ned and I addressed my ongoing concerns as we prepared for our wedding. We didn’t. I didn’t know how to tactfully raise the issue without sounding like I was questioning Ned’s intelligence or character. And he, of course, didn’t even realize there was a problem to be discussed.

Truthfully, my modern feminist self didn’t mind the idea of being the stable breadwinner of the family. But I also didn’t want to marry someone who would be dead weight. Despite Ned’s excellent education and obvious talent, I thought this could be a real possibility—especially as he seemed to be running away from what he disliked (working for other people) more than he was running toward something he was passionate about. Children’s music and ringtones were intriguing to him. But it seemed to me that his real motivation was to avoid being gainfully employed.

In this regard, Ned is actually like most entrepreneurs in the country: one of the top reasons company founders give for starting up is that they do not want to work for someone else.1 As I’ve talked with entrepreneurs and their spouses around the country, I’ve found this to be a common story. Aaron Armstrong of Maple, Wisconsin, left his job because of an abusive, belligerent boss. He decided to open a music studio, from which he currently provides private lessons and trains church groups on building music ministries. Chris Bruno of Fort Collins, Colorado, was successfully leading an American nonprofit in Turkey until his vision outgrew that of the higher-ups. His day-to-day job became about fighting against the limitations placed on him, which was slowly killing his passion for building new things. He knew he had to leave, though he had no clear sense of where he was going next. He tried out a few different jobs until he discovered a passion for supporting the personal and spiritual development of men through counseling programs.

According to a number of studies, the other reasons why men and women choose to start a new venture are primarily opportunistic: they are unemployed or underemployed, or they’ve been working in an industry for ten to twenty years and feel confident enough to start their own venture in that same space.2 Entrepreneurs have also reported being motivated by the opportunity to build wealth, to capitalize on a business idea, or to work in a start-up culture.3

Women are still greatly outnumbered in the start-up world, making up only 31 percent of business owners—a statistic that has increased only five percentage points in the last two decades.4 But for females who choose to take the plunge, being their own boss may provide opportunities that working for someone else doesn’t. Despite being more educated than the male population, women still make only 80 cents for every dollar earned by men and hold only 14.2 percent of executive positions within S&P 500 companies.5

For Lauren Schneidewind of Atlanta, Georgia, the lack of “equal pay for equal work” in her job at a chemical consulting business pushed her to venture out on her own. She was shocked and angered to discover that her annual salary had been $20,000 less than her male counterparts. “It was probably a 20 percent pay difference. It was not insignificant,” she told me. “And they didn’t want to make it right. I could see no path for success there. So I said, ‘If you’re not going to pay me, I’m going to do it myself.’” She decided to start her own consulting firm.

Beyond the numbers, though, many entrepreneurs seem unable to do anything but strike out on their own. They just can’t help themselves, is what many have told me. That nagging yearning to start something often shows up early and can persist through changes in employment, income, marital status, and family planning. It’s like an extra protein has been embedded in the DNA of 10–15 percent of the population, a protein that is all about creating something new and sharing it with the world. “It’s just what they do,” Dave Phillips, an executive mentor and coach who has worked with thousands of executives around the world, told me. “They’re subject to their own poison. They’re a wild bunch. They’re unpredictable. That’s why they’re entrepreneurs: they can roll with the punches.”

Dave Boyce of Provo, Utah, is a classic example of the consummate entrepreneur. Now in his forties, Dave paused for a moment when I asked him how many different jobs he has had. “I counted once for a presentation,” he began, “and I counted forty-three different things I had been a part of in my life.” From mowing lawns and delivering newspapers as a teen, to starting bands and an a cappella group in college, to serving as an executive or board member for several companies that have been acquired, Dave’s life journey has been defined by his pursuit of new opportunities. This desire to try the novel, to provide something of value to others, has intrinsically been a part of who he is for as long as he can remember.

This tendency can show up even when someone has a clearly defined job with a large company. Henry Gross had worked in sales for Bloomingdale’s for twelve years and, throughout that time, he worked his job like it was a start-up. “He treated it like his own business, working long hours, traveling often, and doing whatever he had to do to get the job done,” his wife, Nancy, told me.

They had been married for sixteen years when Henry finally decided to leave Bloomingdale’s to start a specialty store in Princeton, New Jersey, the community where they lived. Nancy had just given birth to their first child. Despite her concerns with the timing, and the even greater stress and longer hours such a venture required, she didn’t think to stand in Henry’s way. “I worried that he would be miserable for the rest of his life if he didn’t do this,” she explained. “And it would be all my fault.”


  • This is a practical, loving, balanced, clear, complete and real guide to living with an entrepreneur. Dorcas has included a sensitive balance between personal experience, applied examples, and research-based concepts. Her authentic vulnerability is both touching and helpful. There is wisdom and depth in every chapter.—Dave Phillips, Leadership Mentor and Speaker
  • Dorcas Cheng-Tozun has written an astute, pragmatic marriage book that will quickly become the go-to manual for entrepreneurial couples across the globe. Start, Love, Repeat paves a clear path through the unpredictable labyrinth of start-up life allowing husbands and wives to a find their way to healthy, satisfying marriages.
    Dorothy Littell Greco, writer, photographer, and author of Making Marriage Beautiful
  • Dorcas Cheng-Tozun has written a real-life exploration of the deep importance of sustained relationships to entrepreneurs and their families. As a longtime investor, I've been an adviser to numerous founders who have faced trade-offs in their personal and professional lives. Start, Love, Repeat provides insightful, engaging, and practical advice for those who want to "win" in life and at work.—Eric Kim, cofounder and managing partner of Goodwater Capital
  • Start, Love, Repeat should be required reading! This guide, and the unique guidance Dorcas provides throughout, is a godsend for entrepreneurial couples and families.—Jessica Jackley, instructor in social entrepreneurship at USC Marshall School of Business and cofounder of Kiva
  • Dorcas Cheng-Tozun has provided a powerful and practical resource for any entrepreneur and their family. I recommend this to any entrepreneur who has ever struggled with balancing their work and spending time with those they love.
    Daniel Epstein, founder and CEO of Unreasonable
  • Start, Love, Repeat is rich in data, actionable advice and insights, inspiring stories, and raw, honest, relatable anecdotes that validate just how intense and demanding the founder's journey inevitably is. Dorcas does a wonderful job weaving an entertaining, dramatic narrative together with helpful advice and eye-opening research and quotations from across the venture spectrum. If you're hurdling down the entrepreneurial path or just along for the ride, you will benefit greatly from reading this book.—Andrea Miller, founder and CEO of YourTango; author of Radical Acceptance: The Secret to Happy, Lasting Love
  • While all couples are challenged with how to balance their work and relationship, Dorcas does an amazing job of guiding them through understanding relational skills that transform their challenge into mutual growth and career success.—Harville Hendrix, Ph. and Helen LaKelly Hunt, Ph. D, authors of Getting the Love You Want and Making Marriage Simple

On Sale
Nov 7, 2017
Hachette Audio

Dorcas Cheng-Tozun

About the Author

Dorcas Cheng-Tozun is an award-winning writer, editor, and speaker. As a columnist for, she writes about the intersection of startup love with marriage, family, and well-being. Her work has appeared in The Wall Street Journal, Christianity Today, BlogHer, the Unreasonable Institute blog, The Entrepreneurial Leader, and dozens of other publications in the U.S. and Asia. Dorcas and her entrepreneur husband, d.light co-founder Ned Tozun, have been married for twelve years and have one adorable hapa son.

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