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When I met Anna Lisa several months ago in Boston, it quickly became clear that this was a woman who got shit done. And since she’s an Instagram star, you can actually track her hard work with numbers. When I spoke to her in August of 2016, her Instagram following was about 34k. Now she’s at 41.5k and growing.
Instagram is one of the world’s most popular social media platform. With enough followers, you can make big money there. Some people have turned it into their careers. Anna Lisa is one such person, pursuing a career as a photographer and lifestyle blogger that relies heavily on her popular Instagram account. Her blog is called Recess City, and her Instagram carries the same title.
How do Instagrammers make money? How do you run an online business? What’s the time and money commitment behind being a lifestyle blogger? Today Anna Lisa takes us through the creation and evolution of her lifestyle brand.
Some back story: Anna Lisa initially went to a small college in North Carolina. She realized that wasn’t the right place for her and that her priorities lay elsewhere: travel, meeting people, and pushing beyond what she had always known. Not knowing what she did want, but knowing exactly what she didn’t want landed Anna Lisa on a boat traveling the Caribbean for seven months.
‘I’d never slept on a boat before that. I’d grown up sailing, but it was a total shot in the dark. And it ended up being the best thing I’d ever done. That was the first time I was in a position where I could be photographing a lot, so the photography component started there.’
Anna Lisa traveled for the next three and a half years. She found a program where she could study and travel, and her camera became an extension of herself.
‘There was a need to document.’ she says. ‘I’d always been a creative kid, but I’d never thought that photography would be my thing. It just ended up that I enjoyed it a lot. I really enjoyed the editing process, which is not usually what photographers talk about. But for me, getting in the zone and editing for hours on end- I could lose myself and I loved it. Just seeing how far you could take a raw photo and drastically turn it into something different.’
Realizing photography was her passion, she focused on growing her Instagram account during her final year of college.
‘I started getting into Instagram two years ago (2014) and I started Recess City in October 2015. I was in my senior year of college in Ireland and I had a light course load, so I decided I wanted a creative outlet. I wanted to see how many photos I can post, how much content I could produce and see if I got a response. That was my plan for the first three or four months and it slowly started gaining traction.’
From the very beginning it was about hard work for Anna Lisa. She followed her plan, creating a ton of content and growing her page. She prioritized growing her page and it happened, the same way that she made her earlier travel plans happen.
‘I’ve always been driven and type A.I also really, really don’t like to fail, so when I decided I want to do this and I want to be successful enough that my partner and I could do this indefinitely, it was like all bets are off for anything else, I’m going to give this 110% effort.
‘People always want to know some sort of secret way to be successful as an entrepreneur, like it’s some sort of crazy notion. For me there have always been two types of people: the people who talk about doing things and there are the people who do things. The people who are getting things done are the people who stop talking and actually act. So basically, I just worked incredibly hard to get it to a place where I could be successful. You have 100 days where you don’t get anything back from doing the work, and then you have one day where you get a lot back and it drives you.’
She knew she had a business blooming beneath her fingers. Once you hit a certain level, companies start coming to you.
‘Eventually, if you gain enough followers, companies start getting in contact with you as a promoter or as advertising. At different sizes you take different steps. At around 8-12k you start getting reached out to by companies that want to send you free stuff. You take a picture and you get the item for free. Then around 20k, you can start surcharging people [for a post]. Or if your blog has a lot of traction you can charge for sponsored blog posts.’
‘That’s what I started working towards in spring 2016. I realized doing this long term checks all the boxes of anything I’ve wanted to do: it’s a creative process, I’m not bound to one place, I can travel all I want, I can get travel for free. It gives me the freedom to do anything I want to do and not have to answer to anyone.’
Our conversation had one continuing theme: it takes hard work. Anna Lisa wakes up at 5am and spend 12-16 hours working each day. Work starts with editing photos for two-three hours, then moving on to write a blog post for a company she’s partnered with. Pitching companies via email is an all day long affair, as is company research. Anna Lisa specifically focuses on companies that make their products in sustainable ways, and pay employees a fair wage.
‘I knew that if my page was going to be successful I needed something more than just being a lifestyle Instagrammer. It’s not fulfilling enough for me. I think that there needs to be a component of giving back in order for me to be able to go to sleep at night and feeling like I’m contributing something more than ‘look at this beautiful photo.’ The more I thought about it the more I started to think ‘how can I turn this into a contribution that’s bigger?’
Anna Lisa has to balance the need to make money with the need inside her to do good in the world. After all, free clothes don’t pay the bills. She’s found that by shying away from working with the huge brands, she’s actually had more financial success.
‘You reach a point as an entrepreneur where you want to be making money and you don’t want to be turning people down. It’s been hard to turn down big companies purely because you find out on the backend that they’re using sweatshops, or they’re just not sustainable or ethical. There have been days where you’re kicking yourself thinking ‘oh, that would have been great exposure’ but at the same time you can sleep at night knowing you didn’t just cause the purchase of 50 items that were created on the sweat of somebody’s back who is never going to get out of poverty.’
In a strange way it’s actually it more financially successful. There’s a lot of small companies that see the value in what we’re doing and say ‘we want to work with you.’ And we’re so much bigger than them, we can provide more value to them than we would be to all these gigantic accounts that have 400-500k followers.’
Anna Lisa makes her money from selling posts on Instagram, sponsored blog posts, and behind the scenes content creation for brands. Not every brand she works with will appear on her Instagram page- sometimes she creates content that she simply sells. She also still receives monthly support from her parents, though that has a strict end point. She recognizes that this support is a privilege that not everyone has. Instagram in particular is an aspirational medium. Everything seems effortless, but Anna Lisa is quick to open up about what happens off camera.
‘I’m very fortunate that my parents blessed me with that opportunity. Obviously, if you want to start something that requires a ton of time, it’s ok to have a part-time job. It’s ok to have a full-time job and work nights. The idea that all these Instagram couples go out and shoot and just produce these effortlessly beautiful photos and there’s no frustration or work on the backend of it is just a fantasy. I guarantee there are so many fights going on with those couples about lighting and editing and product placement, because there’s so many decisions to make.’
She doesn’t call herself a business woman, but that’s exactly what she is. In order to really be able to financially support herself off of her Instagram and blog she drives a hard bargain with all her collaborators. Her business advice for other women is to make sure that any deal you make works for both you and the company.
‘When you’re working with a company, making sure that in the deal you’re not just getting a free product and shooting it for them, you’re getting it out of the deal. So saying that your photos need to be reposted on your page, or I need to be paid. A lot of people feel like they don’t want to ask because they devalue their own worth. They ask ‘Am I really an asset? This is a big company, can I keep up?’ but it’s so important.
‘Being true to your own style while also working with a company is important. Doing content creation for company that I wouldn’t post on my own page is a great way to work with them. A lot of people would turn someone away if it’s not exactly their style, but doing behind the scenes content creation is a great opportunity.’
It’s a lesson she wishes she had learned a bit earlier in her business. Hindsight is 20/20, but she encourages other business owners to know their own value. Know what you are bringing to the table and charge what you’re worth. Knowing that you have value applies to companies, but it also applies to those who mock the idea of being an Instagrammer as a real job.
‘A lot of people don’t take it seriously. A lot of people think if you’re doing this you just come from a lot of money and aren’t smart. It’s very easy to work at a job you dislike and make money. It’s a lot harder to do something you love and risk not making it, in front of all the people whose opinions you value. I definitely think people think I’m doing something ridiculous. I still have days where I think ‘shouldn’t I be doing something more secure, what if none of this works out,’ but for every one of those days there are 10 days where I feel driven. It’s a balance.’
At 24, Anna is a young business owner. Savings are not her priority at the moment; growing her business and travel are. She has no retirement savings, and isn’t concerned about growing her personal savings , a la an emergency fund Due to the style of her business, her overhead is low. She invested in a Nikon D5500 last year (about $1000) and she uses the VSCO app for the majority of her editing (about $15). She has a personal and business account, and she saves most of the money she makes from Recess City for future travel.
‘Right now a lot of the things I need for shoots I can get for free, or I can supplement somehow. For example, I’m working with a company called Ray Collective next week doing promotion, and I needed an outfit for that. I really didn’t feel like going to blow a few hundred dollars on an outfit but I’m not going to turn this opportunity down. So I supplemented that with a small clothing company in Arizona and now the outfit is free. If you can do that and bleed things together, at the size I’m at you really shouldn’t be paying for clothing or accessories.’
‘My first goal is to be financially independent from my parents. I’m ok not having a huge savings to fall back on for the next few years. If I’m making enough money to continue doing this to the degree that I want to do it and to travel, that’s more than enough for my present needs and for the next two to three years.’
Anna Lisa has seen pretty stellar growth in two years, but she knows this is a long game. She focuses on creating the best possible product each time she shoots, and partnering with brands that match her visual aesthetic and her ethical values. For women looking to start their own businesses, her advice is simple.
‘The easy thing to say would be work really hard. I think for me it always goes back to the idea of don’t talk about it, act. It’s insane the number of people who will waste away their lives talking about what they want. So much effort has been put into the talking, three decades down the line they’re in the same place. At the end of the day, the only thing that’s going to change you are the actions you take hour by hour, day in and day out.’
Anna Lisa, alongside her boyfriend Porter, run Recess City. They’re both professional photographers, have been dating since middle school, live in Boston, and love to travel.