Liquor.com

Steve Olshansky founded what would become Liquor.com in 1991 as a catalog company, riding the early wave of e-commerce. He launched on CompuServe's Electronic Mall in 1993, put together one of the first fully functional e-commerce sites in 1995, and acquired the liquor.com domain in 1998. By 1999, the company was generating approximately $3.5 million in sales—substantial for an internet company at that time. The trajectory seemed unstoppable: by 2000, they had filed their S1 to go public.

The business model evolved significantly over the years. Initially, it was product-focused, selling liquor directly. Around 1999-2000, they shifted toward a Daily Candy-style newsletter model built on email subscribers and daily traffic. This pivot proved prescient, as it allowed them to scale without the complexities of physical inventory and logistics.

When the dot-com crash hit in 2000, Liquor.com's IPO plans imploded. Olshansky and his team had brought in professional management—the "gray hairs" that Wall Street demanded—but these executives proved incompetent when markets collapsed. Olshansky lost everything, including the domain. It wasn't until 2005 that he reclaimed liquor.com and began rebuilding. By 2006, he jumped back into the business full-time for six months, then again in 2009 when the current team was assembled. By 2010, he had transitioned to a chairman and founder role while remaining actively involved.

The real breakthrough came with understanding the power of native advertising. One of their biggest traffic sources became Zergnet, a native content distribution platform similar to Buzzfeed. In May 2015 alone, Zergnet drove over 500,000 monthly uniques to the site. However, initial conversion rates were abysmal—less than 0.5%. After working with optimization experts like Bounce Exchange and Unbounce, they improved conversions to approximately 6%. Their email list grew to 1.8 million subscribers, and they now get about 36 million monthly uniques.

The business transformed into a B2B partnership model. Rather than selling product or just generating ad impressions, they positioned Liquor.com as the definitive channel to reach bartenders and liquor enthusiasts. They work with all the major spirits brands—Diageo, Bacardi, Jack Daniel's, Brown Forman, Ramí Martín, and others—offering sponsorships and partnerships that combine email, web, and offline event assets. A six-figure annual commitment is the typical minimum to work with them.

In 2015, the company generated approximately $3 million in revenue. By 2016, they were on track to do $7.5 million—a 150% growth jump. This growth reflected exponential increases in uniques and the high CPM rates they could command by offering laser-targeted access to their affluent, engaged bartender audience. Olshansky also diversified into real estate (having invested roughly $50 million in development over 12 years), writing (published New York Times bestseller "What Is Your What?" with 25,000+ copies sold), speaking, and podcasting. However, when asked where his April 2016 income actually came from, he admitted it was real estate—not the internet businesses that attract headlines.