What it Takes to be an Entrepreneur

Launching a business can be a scary and challenging venture, especially for first-time entrepreneurs. But Anthony Bolognese wasn’t intimidated. At the age of 23, Anthony owns and operates not one but TWO successful businesses in Washington, DC: Capitol Hill Clothiers and Capitol Hill Photo.

Anthony has taken photos for brands such as NIKE, Mazda, Gold’s Gym, and Goodyear and his photography work has been featured in publications including DC Modern Luxury, Capitol File Magazine, and the Washingtonian. He also currently serves on the AF-DC chapter board.

So how did Anthony turn his talents into full-time entrepreneurship? Check out his story.

Leah Whetstone: You’ve dedicated most of your career to advancing ideas and concepts through creative endeavors, and now you’re a full-time entrepreneur. Can you tell us a little bit more about your career history and how you ended up where you are today?

Anthony Bolognese: My career decision was very loosely made when I was about 14. I knew I wanted to be successful, I knew I wanted it to be in a creative way, and that was pretty much it. I went from wanting to be a musician, then an audio engineer, then a graphic designer, then I had huge dreams of running a full-scale creative agency, and I’ve since whittled it down to photography, so it’s been a journey of self-realization over the past nine years. After I graduated (from a technical college in Florida, shoutout to vocational education), I spent two years freelancing and taking any gigs I could get: graphic design, web design, even speech to text transcription. That didn’t last long. I settled for a while on video editing because I got a really great client and pretty good money.

Once I moved up here [to Washington, DC], that money didn’t end up being as great as I had been used to, considering the cost of living, so I had to get back into the “real world” and took a sales job. I tried to do both at the same time, but if you’ve ever worked in retail sales, you know how draining it is, and how inconvenient the hours are for having a side hustle. I flip-flopped for a couple of years between steady paychecks and trying to get it right on my own, and this past year of self-employment has been the first one since living here that has actually been sustainable. I sort of glanced over the multitude of transitions in the services that I offered, but honestly, it was just a LOT of trial and error.

LW: Tell us about the entrepreneur landscape in Washington, DC and why you chose to call it home.

AB: Washington, DC is full of people surrounded by wealth and power that are trying to carve out a piece of that pie for themselves. It’s actually really inspiring. It seems every other block is a coworking space with 50 people’s new ideas for the world coming to fruition inside. It’s nice to be in this area but not exclusively on the government and policy side of the fence, because it seems like a lot of the stresses associated with this city go right over my head. If I’m being honest, I ended up in the DMV as a total and complete fluke. I moved up here while I was still freelancing from home because my girlfriend at the time got a job here. I knew nothing about the city, nothing about the culture, and certainly nothing about the wealth. All of those realizations had me starry-eyed when I showed up and actually lit the fire under me to succeed like so many people around here have.

LW: What is your latest, exciting venture?

AB: Event and fashion photography isn’t often inundated with new revelations, so I’ve branched out into another industry I have a passion for, which is the fashion itself. In January of last year, I sat down with Robert Ordway, who now works on the Hill, and we talked about our experiences in retail and fashion. He had owned a retail store in Indiana prior to moving to DC, and I had been a top performer in selling custom suiting at the retail store that employed me before. After a few mimosas (it was brunch), we had a tentative plan to begin Capitol Hill Clothiers to remedy the sea of ill-fitting and poorly styled suits in the DC area. It’s another work in progress, but certainly a passion project for us both. We’re offering fabrics from the finest Italian mills and a fitting process that is unrivaled by any other made-to-measure clothier on the market. We also come to you for the fitting, so there’s no need to take time off or use your days off to get perfectly fitting garments.

LW: What does a typical day in the life of a young professional entrepreneur look like?

AB: I can’t speak for all types of entrepreneurs, because every industry demands a different type of effort from day to day. For a photographer and clothier, it’s a lot of cold calling to find new clients, a lot of following up with past clients and asking for referrals, and more than anything, it’s a lot of networking. I actually wrote a blog post on my own site about ways I stay motivated to work, and that encompasses what most of my days look like when I’m not actively on a shoot or at a fitting.

It’s definitely not the casual coffee shop and brunch in bed every day that influencers may show you (because I probably took the pictures showing them doing it), but each day is something new. A new client, a new venue, a new set of people to impress, and a new story to tell.

LW: What is your best piece of advice for a young person thinking about launching a business or side hustle?

AB: My best piece of advice for a young hustler is to embrace failure. You will fail at something, that’s inevitable. Whether it’s a minor inconvenience or a business-ending catastrophe, there is no better hallmark of dedication and entrepreneurship than someone who can recognize their mistakes, learn from them, and do it better the next time. It’s VERY easy to get discouraged when it’s you against the world. But having a system of habits in place that keep you motivated and improve your morale so that the bad circumstances don’t seem like the end of your dream frames your mind in a way that turns failure and mistakes into opportunity. Embrace that.