Chirpify founder and CEO Chris Teso's five o'clock shadow and plaid shirt identify him as one of the new breed of payments entrepreneurs. His advice to newcomers: be fearless.

"Anyone that goes in and starts a tech startup needs a level of almost callousness or no fear…because it's something like 90% of startups fail," says Teso. "You have to have a level of adventure or not really caring…some people might say carelessness or reckless."

As head of Chirpify, a company that enables sales over social networks such as Twitter, Teso had to be fearless enough – some might say reckless enough – to make a decision that could enrage all of its 30,000 customers. That decision: phasing out Chirpify's eBay-like openness to transform it into an advertising platform for larger brands.

"Some people were upset, obviously," Teso says. "But it's the right thing for us…working with big brands such as MasterCard and Sprint and Forever 21. We can make more money off the big companies…and the opportunity was just huge."

Founded in 2011 as SellSimply, Chirpify began as a service that allowed consumers to make and receive payments by typing certain hashtags on Twitter (hashtags, which begin with the # sign, make words or phrases easily searchable on the microblogging site).  Chirpify soon began facilitating payments on Instagram and Facebook as well. Initially, Chirpify users needed a PayPal account, but in June Teso's company launched a direct payment processing option which supports credit, debit and automated clearing house payments.

"I was watching a lot of friends and relatives selling on Etsy and Craigslist; they were posting the sale on [those sites] and then they'd go to Twitter and tweet about it," Teso says. "I was trying to eliminate the middle man."

The company has since shifted its focus to actiontags, Chirpify's term for using a hashtag in an advertisement to enable payments over a social network. After seeing an ad, the consumer can order the advertised product by posting a message to Twitter that contains the hashtag from the ad. Businesses can also use actiontags for contests, polls, subscriptions and donations.

'Failed All Over'

Teso's first startup was AthletesAdvanced, a site for connecting high school athletes with college coaches. It failed shortly after launching in 2000. Later, in 2009, Teso started The Good as a product incubator that was bootstrapping its own products. The startup fared better, and Teso left the company in 2011 to create Chirpify.

Born and raised in Massachusetts, Teso had to overcome the odds from a very early age. He has Ehlers Danlos syndrome, a connective tissue disorder with a number of symptoms including hyper-flexible joints and skin that tears and bruises easily.

He spent his first three years of life wearing a plaster hip cast, and "my parents were told I'd never walk," he says. "But I eventually did, and I've been pursuing the next great adventure ever since."

Teso now lives in Portland, Ore., where he enjoys whitewater rafting, hiking, riding his Ducati motorcycle and camping with his colleagues. He also has two pets, an Australian Shepherd/Vizsla mix named Belmont and a Pitbull/Greyhound mix named Brisco, both rescued in Oregon.

"I've failed all over the place," he says. In 2007, I "broke my skull, had internal brain bleeding, lost my sense of smell and had a migraine for four months from swinging on a branch that snapped 10 feet up a tree. Oh yes, and I did actually knock out my front teeth while running across a frozen lake in Air Jordans."

Culture of Chirpify

The new business model seems to be working for Chirpify. Chirpify has attracted celebrities including rappers Snoop Dogg and Lil' Wayne. Tim McGraw, Lady Gaga and Green Day also use the platform.

The company has doubled the size of its team in the past six months.  Chirpify now has 17 employees, including two recently hired executives to help Teso lead the company.

Greg Rau, former founder and CEO of Upstart Labs, a product incubator and accelerator that helped launch Chirpify, became the company's chief operating officer three months ago. Rau advised Teso for more than two years as Chirpify developed. Since becoming Chirpify's full-time CEO, he has shut down the accelerator.

"I met with [Chris] and instantly knew that I wanted to be involved with him," Rau says. "He has such a passion for his idea and product and his vision."

The culture at Chirpify is also inspiring, says Rau. "The environment he's created is really like a family; everyone works and plays together."

The Chirpify team celebrates Thanksgiving together with everyone providing a dish, Teso says. Employees also volunteer together, cleaning up parks or helping at homeless shelters, he says.

And like any family, Teso is open about the company's moves and workings, says Rau.

"He includes everyone in not only giving their input for a product…but really open in sharing all aspects of the business, good and bad," he says. "There's a level of trust here that's really refreshing; it sometimes leads to heated discussions but the outcome is always good in the end."

Twitter isn't known for being friendly to payments companies. It has taken action against companies such as Flattr and Ribbon for violating its terms of service. In August, Twitter hired Nathan Hubbard, formerly of Ticketmaster, to be its head of commerce, signaling possible plans to support payments directly.

Still, a few companies such as Chirpify and Dwolla have sustained payment services on Twitter.

"Startups are breaking the existing models that have been established because they have nothing to lose," Teso says. "Across the spectrum of industries, risk-taking individuals will continue to disrupt industries."

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