jay_levyJay Levy, cofounder and partner at New York-based Zelkova Ventures, was drowning in legal and regulatory paperwork, with fevered anxiety, when it hit him: “I’m an entrepreneur again.”

Levy, whose firm’s portfolio companies include Fab, Klout, and Livefyre, this week launched his own business: an ecommerce wine company named Uproot, cofounded alongside Greg Scheinfeld, a Napa winemaker. Getting the proper licenses and accreditations to make and sell wine took a stressful year and a half, he says.

After years in venture capital funding early stage startups, Levy says he missed the romance of entrepreneurship. In college, he was the first employee at Uconnections.com, a failed Web portal that he describes as Yahoo for college campuses. Now he’s giving it another go-around.

But here’s the thing: He’s not leaving his job as a VC to do so. He’s part of a growing batch of VC/Founders who want to have both at the same time. The most notable example may be Tony Conrad of True Ventures who sold and bought back About.me while serving as a partner at True. Om Malik of GigaOm is a part-time partner at True as well. Ben Lerer of Thrillist is also a partner at Lerer Ventures– although adding on a part time venture role once your company is already scaling seems the more doable route.

Many people who like the creative process of entrepreneurship but need the paycheck and stability of venture capital are enthralled by this concept, but many more who’ve been through the hell of building and scaling companies are skeptical that it can actually work without one or the other suffering.

Aneel Bhusri would be the first to tell you his activity at Greylock decreased significantly once he founded Workday — now a $10 billion public company. Reid Hoffman too spends the bulk of his time at LinkedIn, not Greylock. Both partners are assets to the firm in terms of mentorship and expertise and deal flow. But they’re clear that their companies consume the bulk of their time.

In case it’s not crystal clear what the demands and pressure are like for the most demanding job in the world, I’ll quote Ben Horowitz, in a mantra so fundamental we’ve turned it into couch décor: “One of the horrible things about being a founder CEO, it’s the one job you can’t really quit…or if you do, you’re a punk.”

Levy says it works out so he spends half his time on VC matters and half on Uproot business. What helps, he says, is having a good filtering process. He still reviews every deal, but the firm has an analyst that adds another layer of screening, so it cuts out much of the noise.

“I think we’ll continue to do eight to nine deals a year,” he says, though he adds that it is tougher to do deals because of current valuations. “Or, if we speak a year from now, we might have done four deals. And it might be because of Uproot or it might not.”

Still, Levy sits on several boards, and you’ve got to wonder what his companies think of having a board member who’s got to deal with the pressures of his own business and might be more absent in guiding them with theirs. In response, Levy says he hasn’t committed to anything he can’t handle or balance.

On the flipside, he says running Uproot makes him a better board member because now he’ll be thinking like an entrepreneur. As a startup who covers startups, we get the benefit. Especially in the B2B area, Levy says he now thinks, “Would I use this for my company?” It also gives him the unique opportunity to know his portfolio companies as a customer. For example, Uproot uses Lettuce as a global ordering platform, Ambassador for social referrals, and Spring Metrics for analytics.

As for the wine company itself, it takes some unique approaches. It’s not just an etailer of other wine brands, like so many other failed wine marketplaces and wine clubs that have come before. He’s taking a page out of the private-labeling trend in ecommerce and making his own.

The wine is aimed toward millennials and gen-Xers, who he says is the fastest growing wine drinking demographic and will be the largest. The company only sells directly to consumers on its website, which allows Uproot to control how the wine is stored and shipped. It’s also a way to directly target the tech-savvy Zappos and Fab crowd, and it allows the company to know exactly who its customers are, he says.

While this does create a boutique feel, it also limits the wine’s realistic reach, especially for young city dwellers shopping at posh markets and going to wine bars. It’s understandable that Levy would want to differentiate it from the two-buck-Chuck at the corner store, but it still aligns with the company’s ethos to put it in trendy brick and mortars. Indeed, Levy says he has thought about eventually distributing at a wine shop like Acme Fine Wines in St. Helena, Calif.

The company has also taken a different line on branding. Instead of putting the Uproot label on the front, it’s on the back, and on the front is a color-coded label that corresponds to the ingredients in the wine. For example, a wine with more citrus and passion fruit will have more green and purple on the label. The hope is that a drinker will be able to gather bottles from different years together and see how the flavors have changed. It’s a unique touch, but goes against all convention LOOK-AT-ME branding wisdom.

He’s going for understated and subtle. We’ll have to see if that’s what millennial want. (This one doesn’t mind either way.) Levy has just signed up for a crazy journey. We wish him well. And if he punks out, well, there’s always that venture capital thing to fall back on.

[Image courtesy kk+]