When Life Gives You Lemons, Start a Wine Business

by Rabbi Jacob Rupp June 26, 2018


summer-wine-partyAndrew Breskin always thought he would be a successful lawyer with a penthouse office downtown that boasted sweeping views of the harbor. But it wasn’t until nearly ten years of being a successful entrepreneur, reinventing an ancient industry that he gave up on his original dreams, and instead embraced his current life, elevating the world of kosher wine.

But how did this major pivot occur and why? Andrew passed the bar in 2008, in the throes of the recession.

He found that seasoned lawyers were willing to work for the same fees that entry-level attorneys charge, and firms were quick to take advantage. To keep himself afloat, Andrew quickly developed a legal expertise in a field he knew well, the alcoholic beverage industry. But after helping numerous entrepreneurs with their journeys into the wine business, Andrew felt it was his turn.

From as early as he could recall he had been studying the small wine and liquor collection his family had. He was struck by the variety of the bottles, labeling and the concept that the same beverage could have such variety. As soon as he was of age, Andrew was off to the races learning everything he could about wine and spirits from the best in the industry. He became a sommelier, a ‘wine expert,’ fluent in all things having to do with wine. He started his own website where he began offering news and reviews, as well as buying and selling collections of high end wine estate collections.

At the same time Andrew was following his liquid passion, he was rethinking his Jewish observance. Having been raised as a traditional Jew in a family that attended a large conservative synagogue, he had always kept kosher at home, but not completely outside his home and wasn’t Sabbath observant. In college and immediately after, Andrew spent time studying his Jewish roots and desired to commit to a more observant lifestyle, which would include keeping strictly kosher and observing the Sabbath.

While any lifestyle change can be difficult, as a wine expert in a world where the mass majority of wine isn’t kosher, this transition was extremely challenging.  Andrew had developed his palate on non-kosher wine, having tasted the best wines in the world and having acquired a decent-sized collection of high-end and exclusive bottles. In Andrew’s dark night of the soul, he sold off his very personal collection of non-kosher wine and opted only to drink kosher wine.

For someone with Andrew’s palate, enjoying kosher wine wasn’t always easy. Much of the kosher wine world was sorely lacking when compared to its non-kosher counterpart, mostly because there wasn’t a large market for high-end wine within the kosher drinking world. Most people were used to spending $10-$30 for a bottle of wine, when much of what Andrew sold and had consumed started at $100 or more per bottle and soared quickly northward.

However, to pay the bills Andrew began to monetize the love he had for the liquid art form. It wasn’t necessarily glamorous at first; he worked in the wine department of a gourmet grocery store to pay the bills while in law school. After practicing law for a few years, newly married and with a family to support, Andrew started stretching his entrepreneurial wings and launched his company Liquid Kosher.

The kosher wine world is a vibrant and growing industry dominated by a few very big players, leaving little room for a solopreneur.  But always looking for his niche, Andrew did what he knew best—high-end, high-quality kosher wine that wasn’t just good according to kosher standards, but would rank with the world-class wine that Andrew had enjoyed before becoming kosher.

What Andrew realized was his unique competitive advantage was having tasted the best wines in the world, and he could educate the growing fan base about high-end kosher wine. He began recommending and carrying only a very select collections of wine, stocking them out of his house, and hand delivering them to customers in the nearby areas.

The kosher wine industry is an international business, with the majority of highest quality wine coming from vineyards in Israel and California. Andrew knew France, specifically the legendary region of Bordeaux, was vastly underrepresented. To fill the hole in the market, Andrew flew to France and began to work with an old winemaking family that didn’t produce kosher wine to create a line of kosher bottles of wine. Andrew would import and sell the wine himself. Once he saw the success his wine had amongst discerning customers, Andrew expanded the labels that he imported to other wine makers, and, as of late, has even begun creating very small runs of ultra-premium bottles made by some of the best winemakers in Israel and California. He has followed the trend of the modern entrepreneur and built an online following for himself on social media and has aspirations for a podcast.

Reflecting on his journey, Andrew acknowledges that it was indeed difficult and uncertain. He is just now making peace with the idea that his life and legal expectations were just a stepping stone to something more creative. And advice he gives himself and other aspiring entrepreneurs?

“When I started I had no idea what I was doing.  But since I was initially speaking to people on the phone, I would sound as professional and confident as possible, so no one figured out how young I was or how long I had been in the business. And with each step, I learned more and was willing to take on bigger responsibilities. Sometimes life doesn’t go in the direction you intend, but if you stay true to your passions and move with confidence even if you don’t know where you are going, things will work out.”


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