Whipping Post Vintage Messenger Bag

Before Georgia-born Ryan Barr founded the leather goods company Whipping Post, he was a musician. He was also briefly a teacher, carpenter, and defibrillator salesman. But it was his music – specifically the lack of audience for it – that drove him toward boutique manufacturing. "At the end of college, I was playing music in a band and failing spectacularly," Barr explains. Realizing he needed to put his rock dreams aside for something more practical, he took on a series of odd jobs, only to find himself struggling more as a professional than he did as an artist. He was a front man without a band or a business.

"I'm getting towards the end of my twenties at this point, and I'm like 'I gotta figure this out, man.' Everything I'm doing is just going down in flames," he recalls. "It was at this point that I started messing around with leather at home and I just thought, 'I'm gonna make myself a guitar strap.' "

What started as a simple stress-relieving DIY project essentially launched Barr's future company. "So I start doing that, and then I make some other stuff, and I think, 'This is pretty cool. Maybe I can do this,' " he says.

From there, Barr began laying the groundwork for what would become Whipping Post – reaching out to tanneries, designing more versatile items, and drawing up a business plan – which was no small thing given his lack of entrepreneurial experience. Though new to industry, Barr was able to make it work by cultivating a few key relationships, keeping his overhead low, and sticking to what he knew.

"I started out with products for guitars. I did a kitschy wallet that held a guitar pick, and that kind of took off," he says. "Then I started doing some more mainstream stuff: I came out with [the Vintage Messenger] bag last year – and that really started taking off a little bit."

That messenger bag is the product most likely to put – and keep – Whipping Post on the map. Inspired by the heavy-duty bags carried by postal carriers way back when, the Vintage Messenger bag is one of the best in a market crowded with high-quality products. Made from 100% vegetable-tanned leather, with a suede-lined laptop pouch, it's a solid, eye-catching satchel that doesn't lean on splashy colors or labels.

As for Barr, he plans to stick with the business plan that has worked thus far for him – keeping his head low and his fingers crossed. While chain stores have reached out to him about carrying his products, he doesn't want to interrupt the status quo. "I kind of just like the online thing. I don't have any ambitions to take over the world or be a billion-dollar brand." So far, he's been able to pull this off. He works side by side with a Bernese Mountain Dog named Banjo in his apartment in New York City's West Village. The dog enjoys Barr's singing. [$265; whippingpost.com]