Diana Jue-Rajasingh

Risk-Taking and the Entrepreneur

Posted in Essmart, India, Reading, Social Entrepreneurship, Start Up by Diana on May 25, 2016

At the end of my and Jackie’s Echoing Green New Fellows Retreat, all of us newly minted Fellows received gray shirts with large white boxes across the chest. Below the white box were the words “matters most.” We were then given permanent markers and were asked to pick a word (or words) to write into the box. _________ matters most.

What to write in the blank was difficult for me to decide upon, but ultimately, I wrote “relationships.” I even wrote it with the “s” at the end, despite the fact that I was knowingly being grammatically incorrect. Now, Jackie first wrote “people,” but after our group photo, she felt uncomfortable with her chosen word and fetched a new shirt. Then she wrote, in big, bold letters, “RISK.”

2013egfellowsEchoing Green Fellows, Class of 2013. Jackie and I are standing on the right.

Risk. You know, despite the fact that it looks like I’ve taken risky decisions throughout my life (taking time off school, pursuing a start-up, moving to India), I never felt like I was a risk-taker. I’m pretty run-of-the-mill, to be honest. And every decision I’ve made has been … calculated. To me, the potential payoffs of starting up in South India were always greater than the potential payoffs of not (not necessarily financially, but definitely otherwise). I’ve never felt like I’ve actually “sacrificed” to do anything I’ve done. My faith plays a role in this, too; I go where I believe I’m called, which is the least risky thing to do in the grand scheme of things.

It’s popular thinking to stereotype entrepreneurs and pioneers as avid fans of risk — you know, the guy or girl who likes to live on the edge, never knowing exactly what tomorrow will bring. But from my own experiences, I don’t really think that most entrepreneur are like this. In my recent read of Adam Grant’s Originals, he doesn’t seem to think so either. Here, he’s writing about an investment opportunity into Warby Parker (the online glasses retailer) that he actually turned down because the company’s founders decided to keep their day jobs while starting up:

When I compared the choices of the Warby Parker team to my mental model of the choices of successful entrepreneurs, they didn’t match. Neil and his colleagues lacked the guts to go in with their guns blazing, which led me to question their conviction and commitment. They weren’t serious about becoming successful entrepreneurs: They didn’t have enough skin in the game. In my mind, they were destined to fail because they played it safe instead of betting the farm. But in fact this is exactly why they succeed.

I want to debunk the myth that originality requires extreme risk taking and persuade you that originals are actually far more ordinary than we realize. In every domain, from business and politics to science and art, the people who move the world forward with original ideas are rarely paragons of conviction and commitment. As they question traditions and challenge the status quo, they may appear bold and self-assured on the surface. But when you peel back the layers, the truth is that they, too, grapple with fear, ambivalence, and self-doubt. We view them as self-starters, but their efforts are often fueled and sometimes forced by others. And as much as they seem to crave risk, they really prefer to avoid it.

– Adam Grant, Originals: How Non-Conformists Move the World

Grant continues to write that creative people and successful entrepreneurs essentially manage a balanced risk portfolio. That ability to create something new can only come from a place of security. As Grant points out, Pierre Omidyar started eBay on the side while he was a computer programmer, and he didn’t leave his job until the online business was netting him more money than his then-current job. Bill Gates waited a year to drop out of Harvard, even though he had sold his software by that point. He just took a year off to test out the waters. And those Warby Parker founders were well aware that they didn’t want to put all of their eggs into one basket before knowing if the startup was actually going to work. Entrepreneurs aren’t risk maximizers are much as they are risk mitigators. By the time they decide to go full-time into their businesses, it feels much less like a leap of faith and much more like a calculated decision.

Likewise, if I had racked up large amounts of student loan debt, then by no means would I want to be an entrepreneur. But since I was debt-free, I was free to try something different without fear of digging myself into a hole. Additionally, I had a Fulbright at the time to help support my time in India (and to give me another practical reason to be there), and an Echoing Green fellowship the following year buoyed my income so that I could stay.

I’m thankful that someone has recognized that risk aversion and risk mitigation aren’t dirty words for entrepreneurs and leaders. The heroism that exists in entrepreneurship (and especially social entrepreneurship, since sometimes outsiders see social entrepreneurs as sacrificing a lot for little returns) is truly unfounded.