Who: Josh JohnsonWhat: Following Your Gut; The Male Blogger Monetization & Strategy Where: Dimes, in NYC's Lower East SideOccupation: Lifestyle BloggerJosh, also known as The Kentucky Gent, is one of our favorite Southern Gentlemen. He joined us for coffee in NYC to share about his journey as an independent content creator. Since launching his site in 2013 (as a way to prove that men from small southern towns can have great style!) he's expanded to a full-fledged men's lifestyle destination where he shares his passions for food, grooming and travel. His accomplishments landed him a feature in Southern Living this month as a blogger to follow in 2016! We chatted about taking chances, blogging full-time and long-term goals. Take a second to experience how charming and lovely this Gent truly is. Q: How long have you been blogging at the Kentucky Gent?It’ll be 3 years in September of 2016, but the first 2 years were very, very hit or miss - definitely more miss than hit.Q: Do you blog full time?As of January 2015 I do! Moving into my second year of blogging full-time, and it’s equal parts scary as hell and incredibly rewarding.Q: How long have you been blogging full time, what did it take to be able to make that jump?Just a little over a year now! I began to fall out of love with the job that I had and wanted to pursue blogging full-time, but I wasn’t sure how to go about it. It started to show, and I was let go in November of 2014. I took that as my sign from the universe to follow my gut, and I’ve not looked back since. Lesson learned – always be true to yourself, because if you’re not it shows through, and it can leave you in a compromising position – like getting let go from your sole source of income.Q: How long had you been blogging before you began to partner with brands? Was there a ramping up period, or did opportunities just start to come your way?I was one of the lucky guys that started blogging shortly after it was “cool” for guys to blog, and while I didn’t fully capitalize on that like I wish I would’ve, it definitely helped me begin working with brands from the get go. At first it was just in exchange for product, but when I decided to pursue blogging full-time I made a promise to myself to charge for my work. It wasn’t an easy transition, but I’m glad I did it. While it’s still not the easiest conversation to have – it does get better with time and experience.Josh Johnson for Turbo TaxQ: Can you tell us more about your experience of learning to create sponsored content for brands? any shareable stories or learning lessons from along the way?Always, always, always plan ahead. I like to make sure sponsored content is scheduled as far in advance as possible. It shows the brand that you’re on top of it, and it takes a lot of stress off of you. You should sign a contract for each and every piece of sponsored content you do, no matter what. Trust me. I learned the hard way more than a few times and with big brands. Set expectations clearly, and make sure both parties are on board. If a brand doesn’t uphold a part of the agreement – call them out on it.Q: What are some the different ways you’re currently monetizing your site? Do you have a favorite method?The majority of my monetization is by way of sponsored content. It’s hands down my favorite way of working with brands and making money. I love to tell stories, and that’s a big reason why I started blogging. I feel that sponsored content, when done correctly, can be some of the most organic content on your site, and that above all else it should never scream “ad” to your readers. There’s nothing worse than watching one of your favorite bloggers sell out for a paycheck – don’t be that person! If the brand doesn’t fit your brand learn to accept that, move on, and realize that another opportunity that’s perfect for you will come along.Q: How has your monetization strategy changed over time?I follow mostly female bloggers, and when I started blogging I tried to emulate their strategies, i.e. Like To Know It, Shop The Post, etc., but quickly learned that my readers were not the most avid shoppers of what I was wearing. Probably because I wear what everyone has in their closet already, jeans and t-shirts, but also because a majority of my readers are female. I shifted my focus to creating sponsored food and beverage content, and that’s where the majority of my revenue comes from. Aside from that I’ve begun doing social media consulting, content creation, event planning, and some PR work. As bloggers we learn to wear SO many hats that it’s important to realize that’s another service we have to offer. Find those small businesses in your area that could benefit from some help creating a stronger online presence, and you very likely could have a steady monthly paycheck.Josh Johnson for Living ProofQ: What’s been the biggest challenge in monetizing your site? Realizing that what works for others doesn’t always work for me. The men’s blogging world is still very, very focused on that suit and tie life – and that’s just not me. I’m also a few years behind the curve, and there’s no way I’m going to compete with guys that have claimed the street style market. I’ve had to learn to corner out my niche, and that was incredibly hard and equally as scary. But I’d rather fall and fall hard than never know if I could’ve flown.Q: Do you have long-term goals for The Kentucky Gent brand - a book, a YouTube channel or maybe something else? I have SO many long-term goals in mind, and I should probably get around to writing them down one day, but they include writing a cookbook, opening my own restaurant(s) and men’s clothing store, and traveling the world while telling plenty of stories with the guy of my dreams (currently taking applications y’all!).Q: In a rapidly evolving social media driven world, do you wonder what might be in store for the future blogging? Not going to lie – I lay in bed and think about this probably more often than is healthy. I have the “What are you going to do when you’re 35 and have 2 kids?!” talk with myself at least 4 times a week. There’s something both scary and exciting about that. I literally get to make my future day in and day out. Once bloggers begin to see themselves as self-employed individuals and treat their blogs as a business they’ll realize the options are pretty endless in terms of what’s next. If you can grow a social media following of people that love to see photos of what you’re wearing 7 days a week, how easy would it be to garner a following for a business that has tangible products for sale? Or a restaurant with delicious food? It’s definitely about shifting our mindsets and focusing on the bigger picture. Blogging will continue to evolve and change, but we’ve got to learn to grow with it. If that means we grow out of it – so be it, but we’ll have some the best resumes out there when that time comes.Coffee with Collaborators is an interview series featuring the incredibly talented, creative voices in our community. Interested in having coffee? Email us.