Handcuffed

The premise of his newest volume, Life is a Startup — that the lessons from founders’ experiences can be applied to a wide spectrum of life situations, from marriage to career choices to parenting and much more — has its roots in a conversation Noam had in his office at HBS. One day in the spring of 2010, a student named David dropped by to inform Professor Wasserman that he’d likely never start his own business. Startled, Noam said with a laugh, “Sorry that you’re taking the wrong course!” But David replied, “Not at all! Your course has already changed my marriage.”

There was dead silence in the room. Then David explained that various practices of successful founders covered in the course, things like giving each partner in a collaboration authority over a specific area and tackling uncomfortable issues and looming challenges head-on, had done wonders for the relationship between him and his wife.

It was, says Noam, “a lightning-bolt moment. No one had ever extended my lessons to realms outside of founding businesses. But my student was right: Whether or not we will be founders, we can all learn profound life lessons from the counterintuitive practices of successful entrepreneurs. Founders are dealing with the same human issues we all have — they just have them more intensely and more frequently. Since we experience them less frequently and intensely, it’s easier for us to ignore them or put a Band-aid on them than it is for founders to do so. Founders have to find real solutions to those problems.”

Coming away from that conversation with the epiphany that “Life is a start-up, and we have to be the founders of our own lives,” Noam began asking his students to give thought to the deeper implications that the business case studies they had read might have for life’s various inflection points. To end the semester, he’d give them a writing assignment based on taking one of the best founding practices they had studied in class and helping others apply it to their personal lives. From his subsequent discussions with many students and alumni, he learned that David was not alone in applying the same strategies used by successful business founders to challenging life situations.

And, Noam realized, he had been doing the same in his own life. In Life Is a Startup, for example, he talks about the “handcuffs” people often wear, his term for aspects of our lives that dissuade us from making changes we’d otherwise want to make, such a job change or a cross-country move.

These impediments, which are often of our own making, come in many forms. Sometimes they are financial in nature, such as when someone is afraid to risk a high salary or secure pension for a much-desired yet speculative career switch. But, Noam writes, “however powerful money is, psychic handcuffs can be even more so. If your envisioned leap involves moving, let’s say, you may face loss of proximity to friends and family or separation from religious or civic institutions that provide social support. If it entails striking out on your own, you might face a loss of status or managerial responsibility, as well as the loss of the comfort of knowing what you’re supposed to do every day.”

Then, getting personal, Noam describes the set of “Harvard-crimson” handcuffs (as opposed to the financial “golden handcuffs”) he found himself shackled with when he began considering going across the country from Boston to the USC, where an opportunity beckoned to establish a center for entrepreneurship research and teaching. But reflecting on the lessons he’d taught his own students, he was able to see that a prestigious position at Harvard was really handcuffs holding back career advancement.

In response, he began a series of steps designed to progressively loosen their grip on his psyche. While still at HBS, he decided to spend time at three other universities as a visiting professor and began de-emphasizing his affiliation with Harvard, even giving up his office and email address before he had to. In his mind, too, he trained his focus on the chance he’d have at USC to found a first-of-its-kind research institute and develop a brand-new curriculum, which was a more exciting prospect than being one more HBS professor among two hundred others.

By becoming a visiting professor at other schools, he took another page out of the playbook of successful entrepreneurs, many of whom try out new ventures before committing to them fully. Studies show, in fact, that people who take a staged approach, keeping their current jobs while launching ventures on the side, are one-third more likely to have successful start-ups than those who, afire with passion to get their businesses going, jump directly from their current jobs into being full-time founders.

And so Noam, too, took a visiting professorship in California’s Stanford University, flying out there for a day and a half each week, in part so he could experiment with the long-distance commute. “About halfway through the semester,” he recalls, “I looked at my wife Chana and said, ‘How’s this going?’ And she said, ‘It’s going great, keep it up.’ After I got over being insulted that my presence was expendable, we decided this meant I didn’t have to be tied to Boston and could explore other opportunities.”

In the acknowledgments section of his new book, Noam thanks his wife for “letting me teach three thousand miles away from where I pick up my mail,” and it’s certainly an unusual arrangement, not least because his wife has a very full-time career of her own, as a physician and department head of obstetrics and gynecology at MIT Medical Center. In fact, Noam says with a laugh, “she works far more than I do.”

But despite now having a job on the other side of the continent, Noam has been able to consolidate all his teaching into one semester, and by his estimate he ends up being away from home only about 17% of the year. As for the other 83% of the time, he says, “with Chana being a doctor who’s regularly on call, I’ve anyway always been an extremely involved abba in what my kids do,” in ways as diverse as coaching their Little League baseball teams and going to Thursday night shiurim with his sons.

Although his work now takes him to Southern California, the Wasserman family still resides in the Boston suburb of Brookline, where they’ve been happily ensconced for two decades. Shabbos morning finds the entire Wasserman clan heading for the hashkamah minyan at the Bostoner Rebbe’s shtibel (and as for the secret to having kids who’ll get up that early to daven, Noam says only, “The Eibershter’s siyata d’Shmaya”).

For the past 21 years, he has produced NetTorah, a compilation of divrei Torah on the weekly parshah and haftarah by Rabbi Yissocher Frand, Rabbi Berel Wein, and many others, which he distributes to a grateful readership of hundreds — from Brooklyn to Hong Kong.

One unusual feature of NetTorah is a section entitled “Zemer of the Week,” the product of a minhag around the Wasserman family’s Shabbos table to find various thematic and linguistic connections between the parshah and one of the Shabbos zemiros, “a perfect chance to review the sedrah while inspiring deeper kavanah when singing the zemer.” In honor of his son’s bar mitzvah last June, the ever-creative professor compiled these essays in a zemiros booklet he distributed at the simchah.

The Right Balance

It’s now been three years since Noam became that which he studies — a founder — not of a business, but of the Founder Central Initiative at USC’s Greif Center for Entrepreneurial Studies. With a staff of nearly a dozen and growing, including senior professors, post-doctoral fellows, and its own executive director, this is one successful start-up. Noam is clearly happy he made the move, and looking back, he observes that “Harvard excels at convincing people — both inside and outside the university — that it epitomizes academic perfection, but a closer look revealed a better fit for me elsewhere.”

The move to USC wasn’t the first time in his career that Noam has bucked conventional wisdom to take an unexpected and uncertain route. After a post-high school year at Yeshivat Shaalvim, Noam did his undergraduate studies at the University of Pennsylvania, earning degrees in both engineering and business. After graduation, he interviewed for a position as a management consultant at the prestigious McKinsey consulting firm, but the interviewer, seeing Noam’s yarmulke and listening to him talk about his Shabbos observance and three-month-old infant, had some blunt advice for the young grad: “Don’t even think about going into consulting.”

Noam promptly proceeded to land a job at a smaller consulting firm that would be much more frum-friendly, where he founded a practice group that grew to 19 people in three years. Later, he also worked at a Boston-based venture capital firm, where his work with founders of start-ups gave him his appreciation for what would later become the central theme of his academic career: the critical role that founders’ early decisions play in the fortunes of their companies.

Eventually, Noam went back to school, receiving his MBA at Harvard Business School in 1999, and although his class section had named him the student “Most Likely to Become a CEO,” it was then that his career took a clear pivot. This was at the height of the millennial technology boom, when, Noam explains, “my whole MBA class was heading out in the Gold Rush to the West Coast to grab the gold out there, but I had decided I wanted to go on for a PhD leading to a career in academia.

“So there I was, having to sit down with my wife and trying to explain that I, unlike my peers, was going back to school for who-knows-how-long while not making any money. Let’s just say it wasn’t easy — but fortunately, Chana was extremely supportive once she understood I had done my due diligence and that I had found a passion. Once I began teaching, I saw that as I went about looking for answers on a whole range of questions in the realm of founding, there was no systematic, rigorous knowledge in this very important area, so I made it my own.”

For Noam, the time he spends in Los Angeles has been a literal homecoming, because he and his brother and two sisters grew up there and his parents still live there. He stays with them when he’s in town, and that experience, he says, “has made me appreciate how much kibbud av v’eim I had missed over the last 30 years. Now I can go to minyan every morning and afternoon with my father and have dinner with my parents. Now that he’s retired from his orthodontic practice, my father has begun learning daf yomi, so we have all sorts of discussions over the dinner table.”

Like Noam, his brother Ari Wasserman — author of Making It Work, a mix of halachah and hashkafah on the challenges frum Jews face in adhering to religious principles in the minefield of the contemporary workplace — also went to Shaalvim and Penn. Ari then followed a career path into the legal profession, graduating from Harvard Law School and working at a prestigious New York firm. But at a certain point, he too pivoted. He now lives in Jerusalem’s Rechavia neighborhood, where in addition to his business pursuits, he spends a large part of his day learning and authoring seforim and books. In his book, he discusses the importance of striking the right work-life balance so as to allow time for family, learning Torah, and growth in ruchniyus alongside work responsibilities.

For Ari, no one exemplifies that balance better than his older brother Noam. But, he adds proudly, there’s something even more inspiring about Noam, which is that “he’s as yashar as can be. I mention in the book that Harvard Business School gave him a $5,000 annual technology allowance. One year, he submitted a reimbursement request for only $240, the cost of a new computer monitor, because he hadn’t needed anything else and didn’t want to spend the allowance on anything that wasn’t genuinely necessary. The next year, he outdid himself, spending none of the allowance at all.

“Once, on a visit to my brother in Boston, I needed to print out about 200 hundred pages of material to read on my return trip to Israel, but his home printer was out of toner, so I asked whether Harvard would permit me to use his office printer,” Ari recalls. “Noam replied that while many staff members used office equipment for personal purposes, he liked to avoid it, and instead, he drove me to a Kinko’s to do my printing.”

Not Just for Start-Ups 

Noam Wasserman says that the lessons on organizational best practices in his books aren’t just for high-flying start-ups, but in fact are also applicable to nonprofit institutions. In Boston, he’s had the opportunity to put those lessons into practice, helping guide the growth of two of the city’s educational institutions. Elementary school Torah Academy has 270 students on separate boys’ and girls’ campuses, and the Wassermans’ seventh of eight children will follow his older siblings in graduating from the school in June.

Two years ago, the school decided it was time, after 36 years in existence, to rewrite its founding by-laws and redesign its governance structure to give it a more solid foundation. Noam led meetings with experts in these areas and then assumed the board chairmanship to help ensure their recommendations would be implemented.

Another beneficiary of Noam’s dedication to the klal has been Yeshiva Ohr Yisrael, a local boys’ high school, now in its fifth year, for which he served as founding chairman of the board. Under the leadership of Rabbi Uri Feldman, formerly of the Boston Kollel, it strives to offer a high-level education in both limudei kodesh and chol.

To that end, a strong Torah studies department led by Rabbi Feldman is complemented by a four-year computer science curriculum and a menu of AP classes, overseen by a head of general studies who’s the former superintendent of a Boston-area public school district. “The two of them are the perfect founding team for the high school,” Noam says. The school’s fundraising is innovative, too: Instead of a big annual dinner, it holds several smaller dinners in people’s homes featuring interesting speakers, and for each the last three years, Noam has presented on entrepreneurial leadership at one of these gatherings.

All for the Best Looking through Life Is a Startup, it’s clear that this isn’t just a business book by a religious Jew. It’s a book with a distinctly Jewish feel to it, the product of an author who’s very proud of who he is and brings that identity with him into his work. In the upper-right corner of the table of contents, page one spies the acronym “BS”D,” the meaning of which only his frum readers will grasp; the Acknowledgements section following the book opens by quoting Rabi Tarfon’s saying that “I have learned much wisdom from my teachers, more from my colleagues, and the most from my students,” and closes with thanks to his family and a prayer that “Hakadosh Baruch Hu enable them all to merit continuing to contribute to our families and communities until 120.”

In the chapter entitled “Fail and Succeed Productively,” Noam tells the story of Rabi Akiva and his donkey and candle, even providing the exact citation to where it appears in Maseches Brachos, and elaborates on his entrepreneurial application of the concept of “gam zu l’tovah,” which, he writes, “encourages us to seize seemingly negative events and harness them — to use them as a way to rethink our paths in life or to reflect on learnings that can be used to improve our next steps.”

“Gam zu l’tovah” is a concept that looms large in Noam Wasserman’s thinking. He invokes it twice in his new book to express his feelings as he looks back at two pivotal junctures in his own career — one at which he had to give up on joining the prestigious McKinsey consulting firm, the other when he made his bold move to the West Coast.

Nor does he keep it to himself: He spends the last day of each semester talking to his students about the need to take a “gam zu l’tovah” approach to the challenges they’ll inevitably face in life. Because whether he’s imparting lessons in the classroom or in Silicon Valley, Noam “Ish Gam Zu” Wasserman’s focus is as much on excellence in the business of life as it is about success in one’s life in business.

NO PAIN, NO GAIN

The leading cause of failure in start-ups isn’t a bad business plan, but human relationship issues, both personal and interpersonal. According to Dr. Noam Wasserman, the most successful start-up founders find solutions that can help people deal with similar problems in their personal lives. The following are some of those problems, and what founders can teach us as takeaways for our own challenges:

1. The perils of passion. We tend to think that passion and persistence are the keys to success. However, even before founders start a business, passion can cloud their initial founding decisions and once founded, can lead to overselling business prospects, to not developing contingency plans for under-performance, and to over-persisting even when all objective signals indicate they should move on to another pursuit. In all walks of life, we have to tune in to when passion can be magical and when it might turn into a peril.
2. Accumulating handcuffs. We dream of impacting the world through working for communal nonprofits or of founding companies — important projects but with little pay. Before we do so, we make decisions that seem correct at the time, such as moving into our dream house while taking on the long-term commitment of a high-priced mortgage, or working for a prestigious employer. But sometimes the financial and psychic handcuffs introduced by our earlier decisions prevent us from following our dream. We need to anticipate the handcuffs we’re creating for ourselves, adopt the low-priced lifestyle of a non-profit employee or of a founder (“live like a founder before you found”), and make sure not to fall prey to short-term psychic handcuffs.
3. Fear of failure. We instinctively recoil from failures, but this same instinct prevents us from learning from those failures, causing them to become unproductive failures. Instead, we should learn from the most resilient founders, who build their ability to see each setback as an opportunity for “gam zu l’tovah” — to transform each setback into a blessing from which they learn key lessons or gain motivation. To build this muscle, practice your “gam zu l’tovah” mindset on small setbacks so you’ll be more prepared for big ones.
4. Avoiding negative feedback. It’s natural to recoil from negative feedback and instead only strive to get positive reinforcement. However, founders who avoid negative feedback reduce their chances of success; learning where you’re wrong is essential to finding the right path. The best founders appreciate the importance of the concept of “ezer kenegdo — a helper against you,” that without someone pushing back when we get something wrong, it’s a lot harder to achieve our full potential. In all walks of life, we have to retrain ourselves to seek and appreciate the invaluable role played by someone who pushes back appropriately.
5. Neglecting the 3Rs. The most fateful founding-team decisions (often the most ill-fated) fall into three categories: the relationships they tap (friends, family, coworkers, acquaintances, strangers); the allocation of decision-making roles within the team; and the way rewards are structured. Founders need to know when to pull back on the reins and think about each of these “3Rs” before jumping in. In life, take to heart “sof maaseh b’machshavah techilah — actions should be preceded by thought,” and get a clear roadmap of the most important forks you will face on your path ahead.
6. Not being ready to make the tradeoff. Founders tend to be in denial about having to make tradeoffs. One recurring tradeoff is between keeping control of their start-ups (their “babies”) versus attracting the resources and people needed to grow valuable, high-impact companies. Do you want to be rich (a lesser player in a more valuable company), or do you want to be king (of a smaller kingdom)? When founders are unprepared for the tradeoff, they make inconsistent decisions and increase the chances of both losing control and not growing the start-up’s full potential. In life, we need to anticipate which outcomes we will celebrate and which we will regret, and then proactively architect our decision-making to increase the chances of getting to celebrations without regret.
7. Succumbing to our biases. We tend to avoid difficult conversations and succumb to the magnetic pull of collaborating with people who are too similar to us, sacrificing the long-term in favor of these short-term, “easy” decisions. Instead of succumbing to these biases, the best founders learn how to plan for pitfalls, to build their difficult-conversation muscles and to take a disciplined approach to avoiding sacrificing long-term gain in order to have short-term comfort. These practices apply in all walks of life.

Strength in Numbers

Professor Noam Wasserman, one of the foremost experts on the challenges and pitfalls of start-ups, will present at the kickoff event of TribeWorks business accelerator conference for frum entrepreneurs on November 13. The launch of this hub for entrepreneurs and innovators “will help build a support network and peer group for dealing with the inevitable founding dilemmas that can make or break a successful start-up,” says Wasserman, who literally wrote the book on start-up failures, The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup. (His newest book, Life Is a Startup: What Founders Can Teach Us About Making Choices and Managing Change, extrapolates real-life lessons from the business model.)

The idea for TribeWorks started around a table at the Agudah Convention three years ago, when Zevy Wolman, founder of The Jewish Entrepreneur, an organization that matches mentors and mentees in the Jewish community, was looking to take the concept to the next level. He joined up with social entrepreneur Asher Weinberger, under the auspices of Mishpacha, to create business assistance and referral services to frum businesses.

The effort was a historic collaboration between multiple existing business assistance non-profit organizations in various communities. The TribeWorks coalition, initiated by Mishpacha, is supported by the OU, Agudath Israel of America, Yeshiva University, Young Israel, JCC Marine Park under the leadership of Shea Rubenstein, Crown Heights Young Entrepreneurs under the leadership of Yehoshua Werde, Jewish Woman entrepreneur under the leadership of Chaya Appel-Fishman, and many more.

“When we founded The Jewish Entrepreneur and began this network of mentoring new businesses, one thing we realized is that people are not necessarily unsuccessful because they’re not qualified or because their ideas are bad, but because they make decisions that are avoidable or ill advised, mistakes that could avoided through mentorship,” says Wolman. “The goal of TribeWorks was to aggregate the resources of the various organizations already working in their own specific communities to collaborate. So if one organization provides interest-free loans, one provides mentorship, and one provides free office space, we can try to create a platform whereby each organization’s services are available to everyone else’s clients, with the ultimate goal of giving Jewish business owners a real leg up.”

(Originally featured in Mishpacha, Issue 734)