Painless1099

Class of 2015

About

Painless1099 is a service for helping freelancers save for tax season. We open an online bank account for deposits of 1099 income, automatically withhold taxes based on your personal information (number of dependents, filing status, etc.), and then deposit what is safe to spend directly to your personal checking account. It’s simple and it’s painless. See what we did there?

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Team

ACe Callwood
CEO
Justin Kauszler
Head of Product
Matt Russo
Product Architect
Daniel MacPhee
Senior Developer
Aaron Ware
Director of Business Dev.
Nick Green
Director of Business Dev.

Learn

Was there ever a point in the process of building your company that you wanted to give up? What made you push through?

ACe Callwood: Totally. I read a great article from Ben Huh (Founder of Cheezburger) other day that said “You’re not a true startup unless you flirt with death every few months.” I think there’s a real element of truth to how grueling a startup can be. Tempers flair, depression sets in, and yes, sometimes we feel like quitting. The big thing for us is we constantly weighed the alternatives to startup life and couldn’t imagine doing anything else. We’re a group of guys stoked on building awesome tools for people like us…and if it’s not us, who else is going to do it? Keeping those kinds of thoughts in mind is really helpful for pushing through the low points. On top of that, this isn’t our first rodeo and we all trust each other immensely. This helps to put things in perspective and reminds us that the lows are only low for a little bit and they don’t hurt that much in the grand scheme of things.

If a TV show were made about your company, what would your theme song be?

AC: Either "Shake It Off" by Taylor Swift, or "Tubthumping" by Chumbawumba. Looking at the lyrics, they’re both pretty applicable to building a company, but mostly I picked those because I may or may not have road trip footage of the crew jammin’ to both songs. (In an exciting plot twist, Painless1099 is pivoting to a boy band.).

If a TV show was made about your company, who would play your team members?

AC: A young Denzel Washington (like, pre-Training Day Denzel) for me. Denzel’s understudy would probably be Jude Law or Queen Latifah. Edward Norton definitely plays Justin. (Fight Club Norton, not American History X Norton.) I think Matt would get Eric Bana mostly because Matt does an amazing Australian accent. And Daniel is either Sean Connery or Will Ferrell – maybe a mix of both because he’s wise and hilarious at the same time. Upon review, this movie should 100% exist.

Is this your first startup?

AC: Negative. As a team, I think we have 4 or 5 businesses under the belt – all of which included multiple members of our current team. Having a rapport as a team has helped us hit the ground running. In a lot of ways, Painless feels like the culmination of the bumps, bruises, and lessons we’ve picked up over the years of building products together.