The story of Matt Dowgwillo and Thrifty Hipster encompasses every aspect of entrepreneurship — from the invigorating highs to the humbling lows. It is a process that continues to unfold as he tries to usher his recognizable brand into a new, more competitive era with a redesigned website and a pair of mobile apps.
Dowgwillo originally launched Thrifty Hipster back in 2004, when he was a student at the University of Minnesota. Facing a dilemma that confronts many college kids — a desire to go out and catch a buzz with limited funds to actually make it happen — he was hit with a great idea: With so many establishments around campus offering drink specials to draw in business, why not create a resource that would make it easy for like minded folks to plan their cost-conscious outings?
He went live with ThriftyHipster.com in its original, simple form, and the site became a hit. Within a couple years, it was drawing 40,000 local, targeted visitors per month. In 2007, he decided to try and take the site to the next level, hiring on a development firm for an ambitious $50,000 overhaul project intended to bring Thrifty Hipster into the next generation.
Unfortunately, the shop over-promised and under-delivered on numerous fronts.
“They basically screwed us over,” says Dowgwillo, left. “We’d been 100 percent self-funded, basically operating month-to-month on what we could afford. When we lost that money to the developer it was like, well, can’t afford anything now.”
Dowgwillo filed lawsuits against the company, whose name he declined to mention, and although he eventually won that ordeal, it didn’t matter because the defendant had no money anyways. This left Thrifty Hipster in a state of limbo for years; downtrodden and lacking funds, Dowgwillo pondered shutting the site down.
That’s when developer Robert Nogler, pictured at right, entered the fold.
Working full time at Wells Fargo, Nogler has experience, but had to update his skills for the site relaunch and the mobile apps. He did so while working nights and weekends to complete the new version of the site, which launched back in February. And they just published a new app called “Happy Hour Now” for iPhone in September and pushed the Android version live a few weeks back.
“We’re picking up some lost ground,” says the founder, “..we fell behind, but now are ahead.”
Unlike back in 2004, the concept behind Thrifty Hipster is no longer unique. There are sites like Daily Happy Hour and apps like MPLS Drinker vying for attention in the same space, and although Dowgwillo and his team face financial challenges, they feel strongly that their experience, their local connections and their brand name position them to reemerge as a leading resource for Happy Hour and event seekers in the Twin Cities.
Dowgwillo insists that the site has plenty of stuff in the pipeline, including a restructured revenue model that will involve charging vendors more for services and relying far less on advertising money (he says ads will account for 12 percent of income as opposed to 90 percent before). He’s thinking about ways he can take the platform national, but for now, regaining a hold on the local market is priority No. 1.
Of course, Thrifty Hipster’s rise from the ashes wouldn’t have been possible without a crucial assist from Nogler, to whom Dowgwillo is extremely grateful.
“Bob is the only reason we’re still around, to be honest.”