Parashat Toldos - Dropbox, Pinterest, and Billionaire Bill Hwang

By BJLife/Rabbi Moshe Pruzansky
Posted on 11/05/21

And Eisav said, “Look, I am going to die, so of what use to me is the bechorah (birthright)?...thus, Eisav scorned the bechorah” (25;32-34).

Rashi explains that before Eisav sold his bechorah to Yaakov, he had first inquired as to what responsibilities would be included with it. When Yaakov explained that if one performed the avoda’s ha’bechora after drinking wine or with long hair, it was punishable by death (Sanhedrin 22b), Eisav responded: “I am going to die [if I would undertake such responsibilities], so of what use to me is the bechora”. Consequently, he then sold it to Yaakov.

R’ Moshe Feinstein* asks, if so, what did Eisav do wrong? Why does the Torah state that Eisav “scorned” the bechorah? Didn’t Eisav, in fact, give due reverence to what the avodah would require? He didn’t want to risk doing it incorrectly and receiving the death penalty, as Rashi attests. If so, why does the Torah state that Eisav did something negative by declining it?

Consider the following:

Dropbox: If you’re one of the millions who use Dropbox, you can thank Drew Houston for taking some big risks. Houston started Dropbox in 2007, and a mere 2 years later, in 2009, Dropbox caught the attention of Apple’s co-founder Steve Jobs. Jobs wanted to buy Dropbox and met in-person with Drew to give him a nine-digit offer (at least $100 million or more). Jobs pressured Drew to take the deal, telling Drew that he planned to take over the Dropbox market anyways, with his iCloud service, and that Dropbox would soon lose most of its value regardless. What did Housten do? He decided to take the risk of losing out on such a lucrative deal and decided not to sell his company to Apple. Some of his friends and family thought he was crazy to risk losing out on such an offer. However, Drew felt he could make the company worth even more. His risk paid-off well; in 2018, Dropbox’s value hit a whopping $12 billion dollars.

Pinterest: Ben Silbermann worked at Google and was earning a handsome salary. However, he had aspirations of opening his own company. Should he risk leaving his steady job at Google to do so, he wondered? Ben decided in the end to leave the security of working for Google, in 2010, to start the virtual pinboard site “Pinterest”. After its launch, the company failed to generate a large following, gathering only 3,000 accounts, compared to the 1 million accounts on Instagram. Things were not great, and Silbermann and his small team actually had to operate out of a small apartment at the time. Silbermann considered going back to Google, as it looked like his risk did not payoff. However, against the advice of some, Silbermann decided to stick it out and continued Pinterest, continuing his financial risk. It was a good thing that that he did. Thanks to the launch of its app on smartphones, Pinterest began to see tremendous growth. Today, Pinterest is valued at about $30 billion dollars, making Silbermann’s calculated risk to leave Google and go out on his own, clearly well-worth it.

However, financial risks don’t always work out well. Consider the following:

Bill Hwang: Before he lost it all—all $20 billion—Bill Hwang was one of the greatest stock-traders of all time. Starting in 2013, he parlayed more than $200 million left over from his shuttered hedge fund into a mind-boggling fortune, by betting on stocks. He took risk after risk, and, he was succeeding more than anyone could have imagined was possible. If he would have decided to retire at his financial climax, Hwang, at age 57, would have stood out even among the world’s greatest billionaires. While there may be a few wealthier people, their money is mostly tied up in businesses, real estate, complex investments, sports teams, and artwork. Hwang’s $20 billion net-worth, on the other hand, was as liquid as could be.

But then, in just two short days, he lost it all. In March 2021, Hwang's family company “Archegos Capital Management” defaulted on loans that he used to build a risky $100 billion portfolio. The news came as havoc for Hwang, and quite swiftly, all banks started dumping his portfolio. In just two days, he ended up losing all of his $20 billion net-worth - one of the most spectacular failures in modern financial history: No known individual has ever lost so much money, so quickly. Ever. (

When it comes to financial matters, some people take great risks and others are very cautious & risk-averse. Considering the fact that some risks result in great loses while others result in incredible profit, it is difficult to say which course of action is most wise. However, this is only true when it comes to monetary risks.

R’ Moshe Feinstein explains that when it comes to opportunity to gain ruchniyusly (spiritually), on the other hand, one has no right to shirk his responsibility to grow & maximize his potential – no matter what the risks or burdens involved may be. One cannot sit on his proverbial coach and “play it safe” by not pursuing avodas Hashem - even areas of avodas Hashem such as avodas ha’bechorah, that one can argue are “risky”**.

This is why when Eisav, the man who actually just came back from taking a major risk (as the Midrash Bereishes Rabah states, Eisav was returning from having gone to fight King Nimrode for a very valuable cloak, despite the risk to his life, and this is why he was so exhausted***.), decided he did not want to take on the responsibility and “risk” of pursuing the avodas ha’bechorah, it was considered that he did something very wrong and negative indeed.

Living Inspired

There will always be people who have better middos than us, dress more modestly then us, learn more Torah than us, etc. Often, we are afraid to follow in their footsteps because we don’t want to risk being labeled as overly religious or too frum, we have a fear of burnout, or, we are just afraid that we won’t be able to keep up with them, etc. Although taking things at a responsible pace is always wise, we should always remember the message from our parshah and constantly be pushing ourselves more and more to take that “risk”****. We’re in this world to go ahead and take spiritual risks**, push ourselves to our limit, accomplish, and ultimately, reap the rewards for doing so for all of eternity.

Taking the “risk”, is well worth it. In fact, there actually is no “risk” nor any downside whatsoever in doing so – as we are rewarded not for our results, but rather, for our efforts (see Avos 2:16). 

Let us all, without a promise, take on one new thing today to improve in. Let’s push our limits and reap the rewards. This week, take on a spiritual opportunity; take a risk for spiritual gain.

Gut Shabbos


*- Sefer Kol Rom, from R’ Moshe’s lectures. See also Artscroll’s “Rav Moshe on Chumash”.

**- Of course, one should never risk his spirituality by exposing oneself to impure influences, friends, etc. That is not the risk being referred to here. Rather, specifically when it comes to taking action to pursue a spiritual goal, or to gain spiritually, one cannot allow the “risk” of failure to stop oneself from trying.

***- See also Pirkei D’rav Eliezer

***- Similarly, if there is something that you do that is not optimal for your spirituality, consider taking the “risk” of limiting it or stopping it entirely. Don’t let the fear that you won’t be able to make it, that you’ll burn out, etc. stop you from doing so.