Jason Nash came to Hollywood to follow in the footsteps of Woody Allen, making a living writing and starring in his own work. And he is — on the Internet. An overview of Nash's career in recent years illustrates the evolution of the monetization of scripted digital media. Perhaps it's what Allen's career would look like had he entered the entertainment industry as a twenty something today. Nash has created and starred in online series for GQ (How to Be a Man), Comedy Central (The Shaman, Jason Nash is Married), and most recently Regal Cinema's Date Night Fails.

Originally from Boston, Nash worked for comedian Norm MacDonald on Saturday Night Live during college, then moved to Hollywood in 2001 when he was cast on the sketch show Random Play for VH 1. Nash had success selling several of his own TV shows, but none made it to air. He found the typical road of an actor — taking bit parts in shows and slowly building a resume – frustrating. “Half the time I didn't think the show was even funny,” Nash remembered in an interview at his Studio City home. “I think the right way to go about things is to take small steps and I just didn't have the patience. I never wanted to write on a staff. I wanted to perform my work. I could sell my own TV show, but I couldn't get it made. And I couldn't star in a movie.” So in 2008, he moved his focus away from TV to the smaller screen.

In 2006, MTV had bought digital entertainment company Atom.com, in order to start their own digital presence. Nash, who had also worked at MTV, sold them his first original web series, The Shaman. In it, starred as a Jim Morrison-esque, bare-chested wanna-be guru who goes by the name of Shaman and moves to LA to pay the rent by healing the world. MTV gave Nash a modest sum for him to produce all components of the show and pay himself with the remainder. Nash called in favors from comedian friends including former sketch teammates Mike Blieden (Late Night with Jimmy Fallon) to direct and Matt Price (Men of a Certain Age) to co-star.

They shot 50 pages in 6 days. It wasn't exactly Hollywood money, but it was Nash's first taste of the funded creative freedom he craved and a strong sample for future web work. “I was really naïve,” Nash laughed. “I thought – I'll make this web show and it'll be so great that they'll make a TV show. It doesn't work like that. You still have to pitch the TV show and people in the TV business want to have a hand in what you do.” Yep, the Louis CK/FX deal of total creative freedom on your TV show is a rare one.

Jason Nash and Matt Price in The Shaman; Credit: Courtesy of Jason Nash

Jason Nash and Matt Price in The Shaman; Credit: Courtesy of Jason Nash

After The Shaman, Nash started doing stand-up comedy. When Atom.com execs saw his one-man show “In the Land of Tall Buildings and Red Fire Engines,” about the enlightening and horrifying adventure of being a married father and person of 'potential,' they asked him to create another web series based on the show. Jason Nash is Married, premiered on the site 2010 and followed the daily antics of Nash and onscreen wife Busy Philips (Freaks and Geeks, Cougar Town ). Again, Nash was given a lump sum, this time incrementally larger than for The Shaman, to produce the season himself with full creative control. “It was an amount of money that a rich person throws a party with,” Nash quipped when asked to give a ballpark of the budget.

As viewership on YouTube has climbed over the last few years to the now six billion hours of content watched per month, brands outside the entertainment industry have started looking for ways to increase their presence. Publishing giant Condé Nast, was looking to invest in shows that aligned with their magazine brand GQ and they approached Nash to pitch them ideas. Regarding GQ's strategy, Nash mused, “I think they thought, 'here is a place that we can make money by putting ads on all these videos.' They bought like 40 shows. I wrote the pitch in two minutes and they bought it.” GQ declined to comment for this story.

In GQ's How to be a Man, Nash hosts a faux interview show where he goes on location with celebs of the comedy world ( Michael Ian Black, Andy Richter, etc.) and asks them for advice – most of which is hilariously terrible. Andrea Savage plays his ex-girlfriend teaching him flirting tips, for example, which he constantly misinterprets as actual come-ons. With GQ, Nash had the freedom to write and direct as he wished, but ultimately not all his content made it to screen.

“Brands don't just care about views. Brands care about their brand first. We shot a few things with people that they didn't accept because they didn't feel like that they were their brand.” Nash still produced all elements within a given budget, but his pay was higher than on previous web projects. Imdbpro quotes the budget for How to be a Man at $150,000. The show premiered on Youtube in this August and is still releasing episodes.

In 2012, Comedy Central, owned by MTV Networks Entertainment Group, absorbed Atom.com and renamed it ComedyCentral.com. With almost every studio and network now investing in online content, there was no reason to hide a digital presence behind a different entity. The Shaman and Jason Nash is Married are still available on the site. Around the same time, Comedy Central decided to fund a second season of Jason Nash is Married and once again said Nash could have complete freedom with an even larger budget.

Nash chose, this time, to shoot a feature film. It would be based on the same characters and could be released episodically on the web and as a feature. This is a trend that studios like Fox are turning to as they turn their Home Entertainment departments into Digital Studios. Nash wanted to get the biggest career boost possible from the release of the feature and, like any artist, he wanted people to watch it. Since the film would have very little budget left for marketing, he decided to use another digital content creation machine to gain followers: Vine. Nash's mastery of short form storytelling, self-deprecating humor and willingness to dress up in bizarre outfits in public quickly gained him over 500,000 followers. He's only been on Vine since March.

“I did it to get an audience,” Nash admits. “It's fun, but it's not my first choice of what to spend my time on – – a prank or something. I want the thirteen-year-old kid to see the prank I do and say, 'oh what else did he do? Oh, he made a movie,' and then go check that out.”

Nash's success on Vine had an unexpected bonus. His work caught the eye of Rebecca Coleman, founder of boutique digital advertising agency Something Massive. Coleman approached Nash to partner as a creative collaborator for their new long form campaigns, ie web series. “When you post for a brand on Facebook or Twitter or Instagram – all social media we support and encourage our clients to build robust concepts around – they are all very of the moment,” explained Coleman in a phone interview. “The shelf life is really short. We saw an article saying that for the top brands on YouTube, 1/3 of their views are coming a full 52 weeks after the initial post. That opened our eyes to adding a platform for our brands that outlives the 'of the moment' social media.”

Something Massive produced a successful reality-based web series for client Plum Organics, but their first client to take them up on a scripted series was Regal Cinemas. Coleman pitched the concept of a show about a guy who invites girls to the movies, then surprises her with the fact that he meant a movie at home. Each episode features a different date and a different, relatably terrible thing that happens when you're trying to recreate the cinema experience at home: distractions, buffering, your vintage popcorn maker won't work, no good movies, etc. Coleman brought Nash on to help pitch, write and star in the series, hoping to capitalize on his Vine viewer numbers as well as his mastery of making the minutiae of every-day life hilarious.

The resulting series, Date Night Fails, premiered this October and already has over 350,000 views. Nash now has an ongoing relationship with Something Massive to create online series for brands. “She'll [Coleman] call me in and say, 'Oh we need three ideas for Mastercard,' and then we'll go pitch,” explained Nash. “They'll either get the account or not. It's rough. They do a lot of work. It's just like Mad Men.”

In addition to keeping up his Vine feed and creating branded series, Nash currently has three feature films written that he's pitching to production companies. His feature Jason Nash is Married, ie Season 2, will premiere on Comedy Central's TV channel in its entirety

in March 2014 as well as on iTunes. Additional content and deleted scenes will be available online as the web series component and the actual film may also be serialized.

In a day and age where studio movies have to appeal to international audiences and the networks are regurgitating the same stock shows in different clothes, hoping to hold on to an ever fracturing audience, the web is a place where new voices are not only gaining freedom to create their own work, but finding ways to make a living at it. To the young, impatient Woody Allen hopefuls of 2013, Nash advised, “Don't come out here. Stay in your town. Make the best YouTube show, the best Vine show, the best Vimeo show you can. Then monetize it. Get as many people as you can to watch it.”

Coleman had a similar answer. When asked what she would tell creative types looking to make a living telling their own stories she said, “Make more content, more often, more targeted. That's what this whole micro-content movement is about. I think the reason these Viners are finding success is that they're content machines. They're finding their voice that way. The web allows us to do that. There's not much harm in trying things that may or may not work, but a lot of times what you end up with is something that really works. Get out there, make a lot of content and try not to be too precious about it. The market tells you what works and what doesn't.” – Stephanie Carrie

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