I made a pledge to give back and pay it forward. I will have accomplished that goal if readers gain a newfound confidence that allows them to recalibrate how they look at success, and live their lives on their own terms. The entrepreneurial journey is one of the most empowering, thrilling, and rewarding things anyone can experience in life. Being able to do what you love—and to be successful at it—is truly a gift.
Before you read another page, please answer the following questions for yourself: Who are you the cumulative investment of? Who has believed in you? Take a few minutes to write a thank-you note to those important people in your life, because far too many people don’t. I have personally written numerous thank-you notes, because I am the result of the cumulative investment of the many people who’ve believed in me throughout my life, and who saw more opportunity for me than I could see for myself. And I know that I will write many more in the future. In fact, I look forward to it.
You are also the cumulative investment of the many people who have believed in you throughout your life. I hope that you learn from my own experiences as an entrepreneur, mother, and twentysomething woman, and that you are able to apply and leverage these lessons for yourself—whether you use them in business or in your personal life. They have worked for me, and there’s no reason that they can’t work for you, too.
Lessons I Have Learned
Redefining your path requires you to take the uncommon route and embrace risks at what might seem to be the least logical time.
Create breakthrough moments in your life by being prepared for, and by attracting, opportunities from many different sources.
Keep growing by always learning and always experiencing new things.
Learn to work around obstacles instead of being trapped by them.
Be interesting—create the kind of appeal that transcends age, experience, race, and culture, and will make you a well-rounded and meaningful addition to any team or company.
If your dreams don’t scare you, they aren’t big enough. Remember: They should always be worth it, even if you fail.
Keep going and never stop.
CHAPTER 2
Build a Life That’s Serendipitous by Design
(It’s Okay to Ask for Help)
MY LIFE IS SERENDIPITOUS by design.
You’re probably wondering by now exactly what I mean by that. It means that although I try not to plan each and every detail in my life, I do make sure that I’m in the right place at the right time to enable good things to happen.
It’s no accident that I have a great network of people, and that many opportunities have developed from this network. I am still in touch with, and friends with, the people I looked up to, interned for, and worked with more than ten years ago. I used to wonder why it was that I would meet such amazing people at different events I attended—it must surely be a remarkable coincidence that they happened to be at the same place that I was. Eventually I realized that it wasn’t remarkable at all—we were traveling within the same networks and circles of business and social colleagues and acquaintances. These meetings were serendipitous, but they were no accident—I attended and I was prepared for them.
When I was a little girl, I dreamed about doing mortgage-backed acquisitions. I’m serious. I wanted to be an investment banker like my father. If there’s one recurring theme throughout my life, it’s that I wanted to be powerful and I wanted to be big and I wanted to be successful. As an entrepreneur, most of the businesses I started were either completely on my own or with a very small team. It’s therefore not surprising that when I was a kid I never played a team sport—ever. My love was individual sports—the kind of sports that depended solely on how well I performed as a player, and not on how well my team did. I tried field hockey for a second, and I failed miserably at basketball. In fact, when I dropped out of basketball, I decided to run the scoreboard for the guys and girls teams.
Lauren on … Serendipity
Follow a general path, but stay open to the possibility of unexpected opportunities appearing along the way. Always be prepared for the next big opportunity whenever it may arise. Know the resources you need and be committed to quickly learning what you need to know to be successful.
The one activity that I always stuck with was the violin. I was really good at it and, according to my father, violin is great for people who are mathematicians—he’s always thought that I was a numbers and math whiz. I also thrived as an equestrian and it was the focus of my life for some time—to the point where, when I was in school, I got special permission to use my hours of horseback riding as my PE credit and began training for the Olympics.
I thrived on having control over my own destiny. For as long as I can remember, I have wanted to take personal responsibility for my life. I thrive on the knowledge that I’m responsible for my successes and my failures. No one else. Whether or not I achieve it is all on me. This is what drives me, and this has always been my personality.
So while I have put myself in positions where good outcomes have resulted for me in business, I haven’t made a habit of planning out each and every step along the way. Instead, I follow a general path and stay open to the possibility of unexpected opportunities appearing along the way. Sugarleaf Vineyards was a real estate investment that I turned into a business. There was no big plan to create Luxury Market Branding. It came about when my network found out I was moving on from the vineyard, and many brands voiced their need for my marketing and branding savvy within their companies. I didn’t realize that I wanted my next venture to be in marketing and branding, but that was where my expertise and the needs of my network collided—it was the opportunity of the moment that made the most sense and would yield the best results.
After I sold my interest in the winery, I was ready to get out of the business world for a while and enjoy my children. But Selena Cuffe, founder of the Los Angeles–based Heritage Link Brands and one of my first clients, challenged this idea. I can clearly remember when she said to me, “What do you mean you’re just going to hang out with your kids? Absolutely not. You’ve got the chops to do something else.” So I began Luxury Market Branding. As I was growing that company, I started getting really involved in angel investing—a term meaning when someone provides capital to a start-up usually in exchange for equity in the company. I soon found myself advising a small group of start-ups in New York City.
I have always been a detail-oriented planner, with a keen eye for how my businesses should operate and improve. I’m all about efficiency in every sense of the word. I want to get it right and keep it moving so that I can tackle the next issue at hand. Then wash, rinse, and repeat until I dramatically exceed what others believed to have been possible. This personal approach makes sense when you consider that wineries are one of the top-ten most highly regulated industries in the country. I was able to fly through all the arduous paperwork and process, and I had a real skill for forming companies and overseeing logistics, management, and operations. But not only did I have the business chops required for success, I also had the right personality. If nothing else, I’m hardworking, committed, innovative, passionate, and energetic. I was the kind of person that my colleagues turned to when they faced a challenge—or found an opportunity.
That’s what led me to help begin Gen Y Capital Partners. I was extremely interested and intrigued about what was going on in the venture, start-up, and technology landscapes happening here in New York City, but also in the Silicon Valley and the rest of the country. What I found particularly intriguing about start-ups and venture funds is that the pace was completely different than what I was used to with my winery. It took my own money—money from my savings and previous investments—to get the winery up and running, and then years of waiting while I watched the grapes grow, built a building, pressed the grapes, made the wine, and then bottled it. It was a dream greatly deferred.
In contrast, technology start-ups are sprouting everywhere all the time, and they can be in business within weeks and profitable within months. This was amazing to me, and I was extremely