Startup’s NY move pays off with $500K prize

Ace Callwood

Ace Callwood

A Richmond startup recently caught a new investment on the banks of Lake Erie, where it is moving for at least a year.

Painless1099, a local company that helps freelancers manage their taxes, won $500,000 last week for taking second place in 43North, a startup competition held in Buffalo, New York. In addition to the prize money, Painless1099 and the 10 other companies in the competition will get Buffalo office space for 12 months and access to business services.

Co-founder Ace Callwood pitched on behalf of Painless1099. He said in an email he and fellow founders Justin Kauszler and Matt Russo were pleased with the results.

The prize money will be dispensed throughout the year. In exchange for the awards, 43North gets a 5 percent equity stake in each company, which all must relocate to Buffalo for the year.

“Right now we’re figuring out what the move looks like for the team. It will ultimately depend on what’s best for Painless as a whole, but we’re still discussing logistics internally,” Callwood said.

The competition’s prizes totaled $5 million, and every participant walked away with at least $250,000. The top prize of $1 million went to Buffalo-based ACV Auctions, an online wholesale marketplace for dealer-only automobile auctions.

Next up for Painless1099 is to pitch for the chance to win $100,000 at a competition called People Ops Reinvented in Oakland, California, hosted by Google for Entrepreneurs, Kapor Capital and Village Capital on Nov. 10. The company is also getting mentorship this year from Lighthouse Labs, a local business program that comes with $20,000 in funding.

Ace Callwood

Ace Callwood

A Richmond startup recently caught a new investment on the banks of Lake Erie, where it is moving for at least a year.

Painless1099, a local company that helps freelancers manage their taxes, won $500,000 last week for taking second place in 43North, a startup competition held in Buffalo, New York. In addition to the prize money, Painless1099 and the 10 other companies in the competition will get Buffalo office space for 12 months and access to business services.

Co-founder Ace Callwood pitched on behalf of Painless1099. He said in an email he and fellow founders Justin Kauszler and Matt Russo were pleased with the results.

The prize money will be dispensed throughout the year. In exchange for the awards, 43North gets a 5 percent equity stake in each company, which all must relocate to Buffalo for the year.

“Right now we’re figuring out what the move looks like for the team. It will ultimately depend on what’s best for Painless as a whole, but we’re still discussing logistics internally,” Callwood said.

The competition’s prizes totaled $5 million, and every participant walked away with at least $250,000. The top prize of $1 million went to Buffalo-based ACV Auctions, an online wholesale marketplace for dealer-only automobile auctions.

Next up for Painless1099 is to pitch for the chance to win $100,000 at a competition called People Ops Reinvented in Oakland, California, hosted by Google for Entrepreneurs, Kapor Capital and Village Capital on Nov. 10. The company is also getting mentorship this year from Lighthouse Labs, a local business program that comes with $20,000 in funding.

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Sara Williamson
Sara Williamson
6 years ago

Congrats and best of luck!!!