Bootstrapper Q&A: City Headshots Founder Martin Bentsen on How to Stand Out From the Pack

Living in New York means you always have options. And while that’s a good thing for consumers, it creates challenges for service businesses. If you’re a photographer, for example, you have to constantly compete against veteran shooters with established reputations, extensive portfolios, and deep client lists.

So how did a relatively inexperienced NYU student carve out a place as one of the most in-demand headshot photographers in the city? For Martin Bentsen of City Headshots, it came down to two things: Build a good website and always give your customers more than you promised.

That’s the short version, at least. To get the full story of how Martin built City Headshots from the ground up, read on for our latest Bootstrapper Q&A.

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IN.CREDIBLY: You started City Headshots when you were a student at NYU. How did the idea come to you?

MARTIN BENTSEN: I went to NYU to attend film school, so I was meeting actors all the time. A couple of friends asked me if I could take a headshot for them because they didn’t know anybody else who had a camera like mine.[1] I didn’t even know what a headshot was, but they sent me a link to a website and said, “Can you take a picture like this?” I took some shots of them and had a lot of fun doing it.

I started shooting headshots for free, and one of my friends said to me, “Did you know that a lot of headshot photographers in New York charge $700-$800 for a one- or two-hour shoot?” I’m like, “Holy crap, that’s a lot of money.” I was blown away that that you could actually earn that much money doing headshots.

I decided to create a website for my headshots and I bought a slightly upgraded camera with some money that I’d saved up. I put ads on Craigslist, and I would hang flyers on the NYU bulletin boards that said “$25 for headshots.

How many customers were you pulling in at first?
I only got a couple of people every month who would book with me. But I always knew there was a possibility that one day I could show up on Google. So I decided to research search engine optimization, and how you can write blog articles or backlink to your website. There’s a ton of free information and articles online about SEO. I just started going crazy trying to get my website up on Google.

I looked at my competition and saw there were no other photographers who seemed to know a lot about marketing, so I was like, “Let me see if I can take advantage of this and get my site to show up ahead of all the other competition.” Photographers aren’t super business-savvy for the most part — they’re usually more artistic. So I decided that if I can get ahead of these people, my headshot photography could turn into a successful business.

It’s obvious that your website sets you apart from your competitors. These days, how much of your business is coming directly as a result of that website, and the SEO and the content efforts that you’ve done?

I’d say 80% to 90% of my clients find me on Google and Yelp because of my search engine efforts — I show up on the first page of Google if you type in “head shot New York” — and then the rest of my customers are referrals, word of mouth, and repeat clients. During the slowest months of the year, we get five to seven calls or new contacts per day, and then during the busy season, 15 to 20 people are calling per day for headshots.

Credibly recently conducted a survey with over 1,400 small business owners, and we learned that just 37.5% of them had websites for their small businesses. A lot of these business owners were only relying on Facebook or other social channels as their web presence. Are they missing out on a huge opportunity?

I believe that if a business doesn’t have a website, they’re missing out on being taken seriously. To me, it’s the same thing as not having a headshot on your LinkedIn profile — you look like a fake profile, or someone who started a profile and never finished it. It’s the same thing as not having a website.

If somebody gives me their business card and there’s no website listed, it’s like, “Okay, how do I find out more about you?” “Go to my Facebook page.” What if I don’t use Facebook? “Well, email me and I’ll tell you about what I do.” It’s so much easier when you have a website. It’s basically like having a 24/7 sales team pitching your work to everybody who comes across your site. They can learn all about you and it’s almost free. You don’t have to pay anybody to explain anything. It’s so useful.


(City Headshots promo video via MJBHomeEntertainment)

Earlier, you mentioned your “busy season.” How is photography a seasonal business?

It’s dependent upon hiring season, it’s dependent upon pilot season for actors[2] — when they’re all trying to get into television shows — and it’s also dependent upon medical residency season. Like a lot of other businesses, our summer months are a lot busier than the winter.

Headshots are something that you buy for yourself, and people are less likely to spend money on themselves around the holidays when they’re spending money on presents for other people. They’re also less likely to book when it’s really cold outside, if they want to do an outdoor shoot.

When did you decide to invest in getting your own studio? Did you reach a point where you didn’t have enough physical space to keep up with the demands of your business?

There are so many people who start up small businesses and work out of their apartments, and that’s great because you can keep costs down. But the downside to that is it doesn’t look as professional to your clients, and it makes it harder to maintain that separation between work and personal life.

I researched online and was able to find a good-sized studio. At the time, it was only $2,400 a month, which was affordable for me. Sometimes when you mull things over for too long, you lose opportunities, so I was like, “Let me just get this place. I’ve been running my business in a surplus, I’ve never been in debt, and I need to get a space.”

When I first got the studio, it was way under capacity — I didn’t have enough equipment to fill it. But once we fixed it up, once we put in nice lighting and stuff like that, people started noticing. Rather than thinking, “Nice little place,” they’re thinking, “Wow, this is an actual professional studio.”

Just like having a high-end head shot or having a website, it says to people that you take yourself more seriously. Businesses and clients were much more comfortable referring their friends to me, because they weren’t sending people to someone’s random apartment.

You give your clients high- and low-res copies of all the photos from their photo shoot within 24 hours and you don’t watermark them. That’s very unique in this business.

To me, the most important thing is making sure that my clients are blown away when they leave, because they weren’t expecting anything like what they got. We have a much nicer studio than people are expecting. Everybody is friendly here. Making coffee drinks is a hobby of mine, so I roast my own coffee beans and make espresso drinks for everyone. Today I made some peppermint mocha lattes, and I did latte art on them while my clients were getting makeup done. We do all these things that people aren’t expecting because I’m always in the mind of under-promising and over-delivering.

So you don’t feel like you’re leaving money on the table by watermarking your photos and forcing your clients to purchase every shot they use?

Honestly, I don’t really care that much, even if I’m losing money that way. It’s money in the short run. I think it’s much more important to get a lot of clients in the door and have people leave blown away so they tell their friends, rather than try to nickel-and-dime people for the smaller things.

Speaking of which, you use a lot of discounts and promotions for your business. Clients can save money by bringing a friend, or tagging your business on Facebook, for example. Do you feel like these discounts and marketing decisions are paying off? How do they affect your bottom line?

I think one of the problems with small business owners is the fact that they’re not always open to experimentation. I like to experiment a lot. Fortunately, I’m not running my business in the red — I’m always trying to stay in the black by many thousands of dollars every month — which makes it really easy for us to experiment and take risks.

I like to throw a lot of things at the walls to see what sticks, and sometimes you lose a little money by doing that. But to me, the potential reward is a lot bigger than the cost.

How far down the road are you looking? What are your goals for the future of your business?

Our goal for 2016 is to work with between 5,000 and 10,000 clients. That’s a really lofty goal. In the past, we’ve only had about 1,500 to 2,000 clients in a year. But this year, as we expand to other locations around the United States, we hope to serve a lot more clients. The City Headshots name was trademarked as a national trademark this year.

We’re now in the process of putting together the City Headshots Associate Photographer Program, where photographers from different cities and different states can sign up to be a City Headshots associate photographer. We’ll be able to use our online web presence and our reputation to drive business to photographers, and they’ll be able to take part in our services, from file management to printing and retouching. Our associate photographers can grow their own businesses, and in the process learn about the business practices that have been effective for us.

We’ll also be teaching the photographers how to manage themselves during the shoots. There are a lot of photographers who don’t know what to do when they encounter clients who are critical about their work; the photographer might get emotional and send them a nasty email or something. We want to make sure they don’t make decisions that could hurt their business or get them a bad review online.

I love surprising people. It’s like when you’re buying a Christmas present for someone, and you come up with something that’s just going to blow that person away. I try to do that with clients. When you come in, you’re expecting something decent and you get something amazing. That’s really fun to me, to see people walking away excited, and that’s what I hope we can apply to a much larger audience next year.

Follow City Headshots on Facebook and Twitter.

[1] “I got into video when I was really young. While I was in high school, my friend’s sister was getting married and I offered to do the video for the wedding for a really cheap rate because I had a camera. They said sure, and it went really well.

A bunch of their friends and family members started calling me to do their wedding videos, eventually leading to some people asking if I could do their wedding photography. I didn’t have a photography camera at that time but I knew some basics about photography, so I bought my first little low-end DSLR camera and started shooting weddings here and there.”

[2] Martin published a book called Actor Self-Promotion: Do It Yourself, a 40-step program that teaches everything from how to create an acting reel to managing your finances to avoiding scams.

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