Dylan Benjamin Talks Blogging, Finding His Passion & Navigating Brand Partnerships

Influencing is an ever-evolving art form. While influencer marketing has been a successful growth strategy for many brands and companies, the market is saturated and consumers have caught on. Both influencers and brands must now prioritize authentic partnerships and messaging. Dylan Benjamin – who created a fashion and family blog, Life by Dylan – is one of many doing influencer marketing well. 

We spoke with Dylan on where he was prior to launching a successful blog, notable moments in high career, and key marketing lessons he’s learned along the way. 

 

What were you doing before starting your blog Life by Dylan, how often were you working in digital, and what were some of your goals and aspirations within your previous career? 

I’ve always been an entrepreneur in some aspect for as long as I can remember. In 5th grade, I was selling yo-yo’s out of a briefcase at school, and when I was 16 I was importing electronics from China to resell. In college, I started my first serious company which was a restaurant delivery company similar to Favor, Postmates, Uber Eats, etc., except it was 2005. Back then, all companies were using Nextel push to talk phones to dispatch their drivers – an awful, labor-intensive process – and I came up with a website interface that allowed my delivery drivers to interact completely though what was probably the first touch-screen phones available. I merged with another delivery company, and using our technology, we were able to scale the business to the point that we were eventually selling franchises and had locations in 22 states.

That business has taught me a lot of lessons about how businesses should operate, but even more so about how owning different types of companies can lead to drastically different lifestyles. With the delivery business, we were dealing with restaurants that didn’t always make the food correctly, drivers who didn’t hold much respect for their job, and customers who expected their order to be perfectly delivered in under 60 minutes. A lot can go wrong with that mix, so there were issues each and every day that needed to be solved.

I’ve been with my wife, Lee Anne Benjamin, since starting my delivery company, so she’s been around the whole ride. We moved around a lot for my job, and Lee was kind enough to move with me. She was taking whatever job she could find in each city, and it wasn’t really fair to her, so one day we sat down to brainstorm what type of career would fit exactly what she wanted. She wanted to be able to take the job with her to any city we traveled to, and she wanted to be able to work from home so she’d be able to spend time with our kids when we had them. Blogging fit perfectly! It was a much smaller industry back then, and we didn’t expect it to grow to what it is now. 

The Beginning 

We love how you tie in family life, city living, and personal style – both on your blog and Instagram. What made you want to start blogging, and where do you gather inspiration for your blog content? Following your life in Austin has been so much fun! 

The inspiration from my blog usually comes from something I’m interested in, while also trying to produce something of value to others. I’m passionate about entrepreneurship, health, tech, and living a happy life, so those are the basis on what I share.

I’ll experiment and try out a lot of different things, and give my unfiltered honest opinion, so others can make easier decisions. I also share a bit about how to start a company, and that comes from me having a lot of help along my entrepreneurial path, so I like to share what I’ve learned with others to make their journey easier than mine.

What are some notable moments within your blogging career and what long term goals do you have for Life by Dylan

Long term? I’d love to do this forever. My wife and I both work on our blogs, videos, etc. full time, and there’s something great about sharing things your passionate about and being able to make a living doing it. I’ve worked many jobs and owned different types of companies, and something I see of people not giving enough attention to is their work/life balance. It’s been said so many times by so many people, but money doesn’t bring happiness. Doing something you like every day does.

The Strategy 

So we’re glad you’re using our social planning tool! How did you first hear about Planoly? 

I first heard about Planoly when looking for an app that let me lay out my photos to see how they’d look on Instagram before posting them. Everyone likes to have a consistent flow to their photos, and it’s surprisingly hard to get them to match without seeing them next to each other. You can edit every photo in a similar way, but they’ll never going to look match up due different lighting, colors, etc. 

I later found out Planoly was started in Austin, Texas too, so I ended up grabbing coffee with Andy the founder to talk about business, which only made me like the company more. You never know who’s working behind the scenes of companies you use, so it’s awesome to see it being run by some genuinely great people.

Let’s talk brand deals. What does it take to form a successful partnership with a brand?

When it comes to brand deals, there’s one big golden rule. You have to genuinely believe in and like the product or brand.  The second you start selling out to shill a brand or product for just the money, the value of your channel drops. There’s a trust that is slowly built with the people watching and reading your content, and it’s very easy to lose it. Once people can’t trust you, your channels no longer have value.

Let’s talk future. How do you think the blogosphere and influencersphere will shift in the years to come? Do you see more men stepping out on the scene?

The blogging and influencing industry shifts quicker than most industries, and I don’t see that changing. It’s vulnerable to people’s interests, global trends, and even the various platforms initiatives to keep their stock owners happy. One of the reasons we now make 3 videos a week on YouTube is that we don’t want to have too much of our content on a single platform. It’s too much of a risk. At any time, Instagram could make a change that’s great for the company, but not for people like us. We’ve already seen changes when Instagram went from a chronological feed to one fed by their own algorithm, and another when they stopped showing content to all followers. 

It’s hard to say what changes will come, but from an influencer side, I think it’s smart to diversify so that if any one platform significantly changes, you’ll still be able to afford to make the content you like to make.

 

What are some key tips and tricks you’ve learned along the way throughout your blogging career? Can you share a few best practices for those that are just starting out with their blogs? (ie: growing your brand, finding your niche, engagement, etc…) 

For people just starting out, it’s a little rougher than it used to be. Brands are pickier these days because there was a period where a lot of people were paying for fake followers, likes, etc. It hurt the credibility of the industry for people who were organically growing. 

For people who want to get into this industry today, I would spend some time producing content they love to make and see what catches on. One of the great things about this industry is that it’s easy to measure results. You can see how many people have viewed your photos or videos, liked them, etc. Figure out something you can talk about every day, like to talk about, and people enjoy. Once you figure that out, put in an entire year of making great content and not accepting any sponsorships or collaborations.

It’s easy to get excited when brands start reaching out, but accepting deals too early can make it harder to grow your audience. You need to be your authentic self, and when first starting out, it’s harder to stand up for the integrity of your content when people start trying to pay you. Once you have more experience and a larger following, you’ll have a better understanding of how to work with brands in a way that doesn’t detract from your content.

For more posts like this one, make sure to follow along with our Influencer Chat Series through the hashtag: #InfluencerChatSeries on Instagram.

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