This week, we dropped into the Painless1099 office to grab a beer from the kegerator and get the scoop on their new software that helps contractors and freelancers set aside money for taxes. If you’re a freelancer who has ever forgotten to save for tax season, then you know the pain it can cause come April 15th. Read on to find out how this startup is working hard to make sure you never get blindsided by the IRS again.
Meet the team
Hometown: Chesapeake, Virginia
Title: Co-founder / Chief Executive Officer
How do you like your ice? One big, compressed ball. I think there’s a machine that does it. I’m not sure, but I’m almost positive I need one.
What are the best 30-minutes of your day? I’d say 4:30-5:00 is when I hit my power band. The end of the day is pretty quiet and it’s when I crank through a ton of work.
What does retirement look like? I don’t know that I’ll ever retire-retire. Probably traveling. I like the idea of buying a bunch of small apartments and hopping around the globe. I’m attracted to a more European lifestyle – wake up, consume content, midday siesta, eat a late dinner with a crew of good people. Rinse. Repeat.
Hometown: Richmond, Virginia
Title: Co-founder / Head of Product
How do you like your ice? One giant ice cube – every time. I call it “on the rock.”
What are the best 30-minutes of your day? My morning shower – yes, it’s a 30-minute shower. Contrary to what everyone else does, I do not to come up with great ideas in the shower. Have you ever heard of shower naps?
What does retirement look like? I don’t plan on retiring if I can avoid it. I guess for me retirement is financial stability to a point that I can work on things that I want to work on. Traditional retirement doesn’t interest me – what would I do with all that time?
Hometown: Newport News, Virginia
Title: Co-founder / Chief Operating Officer
How do you like your ice? Big Cube. I just think they look cool. Or when they have a big block and chisel a piece off.
What are the best 30-minutes of your day? There are two moments every day – once right before and once right after work – when I take a moment to clean everything up and then stop for a moment to take a breather. It’s a chance to pause and gain perspective on what I have done and what I have to do.
What does retirement look like? It’s the ability to wake up everyday, have a goal, and, without regard to cost, work toward that goal. To be at a place in my life where I can continue to learn and try new things without obstacles – like for example, a job.
Hometown: Richmond, Virginia
Title: Senior Developer
How do you like your ice? Single Cube – bigger the better. Pearl Raw Bar at Addison and Main has hilariously oversized cubes. The tray only has six cubes, so you have to ask for it specifically.
What are the best 30-minutes of your day? I’m the most productive in the 30 minutes leading up to lunch. I never want to leave what I’m working on, momentum means a lot to me. Once I have that “deadline” set for myself I get inspired to move more quickly.
What does retirement look like? I’m not really thinking about it. It probably won’t happen. I don’t ever see myself just not doing anything.
Interview: Ace callwood
Painless 1099 in your own words, go.
We’re a financial tech company that automates tax withholding for independent contractors. Essentially, we help people who earn 1099 income set money aside for taxes.
What was the inspiration behind starting Painless?
The catalyst was personal pain and the experience of one of our buddies who owed a huge tax bill he wasn’t prepared for. The idea is, if we take care of the headache (read: taxes) on the plate in front of freelancers it allows them to focus more on what they know and love while we handle the rest. Most 1099ers aren’t sure how or what they should be saving for taxes. Instead of trying to educate people, we’ve figured out it just makes more sense to automate the whole process.
This was developed out of a need you saw for others and also yourselves. How does being your own target audience change the development process?
When you’re building a product for yourself, you put a different level of passion into it. You know the intricacies of the problems you’re solving, but it also makes it harder to digest feedback, so we have to balance that carefully. We talk to as many people like us as we can. Although we were the impetus, hearing other people’s experiences helps broaden our reach and that’s really important. Other people are critical – you can’t build a company from a garage anymore.
How has launching a fintech company differed from your past projects?
Honestly, fintech is a pain in the ass. It’s a new beast for us, and the security and regulated banking space are things we have to navigate really carefully. Working with banks is also a slower process than we’re used to and it has turned out to move even slower than we anticipated. We also feel a lot of responsibility as we’re dealing with people’s hard-earned money. We certainly don’t take that lightly or for granted.
What does a typical workday look like?
Justin is always the first in at 7:30, then me around 8:00 or 8:30. Daniel and Matt come a little later, but we all check in by 10:00 AM to set expectations on where we’re working and how we can be reached. Besides that, we’re basically on-call 24 hours a day. We use Slack for our team communication and it has really changed the way we’re able to work with each other.
Personally, I spend a lot of my mornings in coffee meetings, then at the office it’s calls and emails most of the day. I like to stick around until 7:00 or 7:30 PM, but even after that I’ll usually sit outside Lamplighter and work for a few more hours.
With an around-the-clock work schedule, how do you create the space to unwind?
We use the office to unwind – we have fun and we’ve created a great work/play/lounge environment. This is really critical since we all spend so much time here. Of course, there’s a kegerator here and a ton of new breweries nearby. Also, we’re all friends, so that closeness and fun helps us from getting wound up. But when I’m home and unwinding, you’ll find me on my stoop in the Fan, playing my guitar and having a drink.
When you aren’t enjoying libations at the office or a nearby brewery, where’s your favorite local happy hour?
Friday night at the VMFA is the best happy hour in town. After that, Savory Grain has great specials from 4-7, and they also have some phenomenal appetizers.
Words of wisdom you wish you could give to yourself 3 years ago:
Lean into being you. As cliche as that sounds, being yourself is what people are signing up for. (Unless you’re a douche. Then don’t be yourself. Haha.) Really though, it’s your energy and personality that you’re bringing to the table. As soon as you start to act the way you’re “supposed” to, you lose out on a pretty crucial touchpoint and an opportunity to connect with people.
Photography by Alexander Kreher