Michael Thompson | Richmond BizSense

A nascent company that recently expatriated from the Richmond startup scene for a dip in a larger capital pool has hit yet another milestone: the launch of its product to the general public.

Today, one day after the filing deadline for IRS tax returns, Painless1099 is launching an initial free version of its service that helps freelancers manage their taxes.

The launch is still considered in “open beta” phase and is free for anyone who wants to sign up through the company’s website. Founders Ace Callwood, Justin Kauszler and Matt Russo – former VCU students who formed Painless 1099 in Richmond in 2015 – have been testing the service with a closed group of users that eventually numbered around 100.

“We’ve gotten to a place where users feel good about the experience,” Callwood said of the launch.

Painless1099 lets people set up accounts to sock away money for taxes brought in from freelance jobs. Users direct their clients’ payments to their Painless1099 account, which then divvies up money for saving for tax season and the rest is forwarded to the user’s linked personal account.

As a way of luring in new users, people who sign up for Painless1099 while it’s in its “open beta” phase can use it free for life, Callwood said. Eventually the company will do paid subscriptions but Callwood could not say when they will be implemented.

Money sent to Painless1099 accounts can be done by direct deposit or with peer-to-peer sites like PayPal. Callwood said one of Painless1099’s next goals is to be able to let users accept paper checks.

The company itself has gotten some practice when it comes to accepting checks.

Painless1099 won $500,000 last year as part of a Buffalo, New York, startup competition that required the company to relocate to the chilly city known for its chicken wings. The money helped Painless1099 hire two VCU grads, bringing its employee count to six.

While Buffalo is the company’s new headquarters, it still refers to Richmond as its hometown in its press materials.

Painless1099 also went on to win $50,000 at an Oakland, California, pitch competition and got $20,000 as a member of Lighthouse Labs, a Richmond business acceleration program. Later this month, the company is taking the stage at two other pitch competitions, including the Launch Pad PITCH Competition in New Orleans, Louisiana.

Callwood said pitching to crowds of startup fans and investors is a fun, if tiring, part of Painless1099’s development.

“We’re back on the circuit,” he said. “At some point it does get grueling to be out pitching all the time. It’s a good thing for us.”


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