Dave Bowden of Irreverent Gent: “I wish someone had told me to follow my passion first, and profit second”

I wish someone had told me to follow my passion first, and profit second. I wasted a lot of time oscillating between various ideas, debating which ones might be more lucrative, only to see them fizzle out. If I had just pursued my passion from the get go, it would have provided me with a […]

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I wish someone had told me to follow my passion first, and profit second. I wasted a lot of time oscillating between various ideas, debating which ones might be more lucrative, only to see them fizzle out. If I had just pursued my passion from the get go, it would have provided me with a path to profitability that was both shorter and more authentic.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Dave Bowden.

Dave Bowden is the founder of IrreverentGent.com, a popular men’s lifestyle blog that shares advice on everything from fashion and grooming to personal development and dating advice.

Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

I’ve been interested in fashion since I was a kid. My grandfather was always the best dressed guy in the room, and I think his influence rubbed off on me. When I was in fifth grade I remember wearing a shirt tie and button-up vest to school, while all the other kids just wore shorts and t-shirts. So my interest style started early, and has never really left.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I started my career in journalism, but I switched to content marketing when I went to work for a travel company and helped them start a travel blog on their website. As the site started to grow I realized I had a knack for blogging, but travel wasn’t really my passion. One day at work I was doing some online shopping while I put off writing yet another city guide, and it hit me: writing a 2,000 word blog post would be a lot more fun if it were about men’s style. From there I started doing all the fun things that go into starting a blog — coming up with the name, deciding on the direction of the content, etc. — and got really excited about the idea.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Even though blogging was my day job, it took awhile to figure out how to monetize my own. The biggest thing that helped me was listening to podcasts and reading blogs about blogging and making money online. Pat Flynn’s Smart Passive Income podcast was an early influence, as was Brandon Gaille’s The Blogging Millionaire. Eventually I started learning about things like affiliate marketing and display advertising, and slowly but surely started adding income streams to the blog. Even once those were added they still took awhile to grow, but eventually they gained traction and I started to see the potential.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

If you’re reluctant because you don’t think you can make money at it, just remember this: a person who loves what they do is going to work a lot harder and more fervently than someone who just punches the clock and collects their paycheck, and is therefore much more likely to come out on top.

But if you’re reluctant because you don’t want to find yourself resenting your hobby or viewing it as “work,” keep in mind that we all have to do something for work. You can spend your life putting in 40 hours a week selling widgets, or you can spend it pursuing your passion.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I’m lucky in the sense that blogging constantly requires changing gear. Once I’m done publishing and promoting one post, I immediately turn my attention to the next one, so there’s always a new, fun challenge right around the corner.

Plus, as mentioned above, I really feel very grateful to have a job I love, which makes all the boring tasks a lot easier to swallow. Every job has some mundane, unenjoyable aspects to it, but I would much rather do those boring tasks while getting paid to pursue my own passions than while getting paid to pursue someone else’s.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

The thing I enjoy most is the freedom. I have full creative control over my blog, which is not something I ever had as a journalist or a blogger for hire. And I also have full business control: I decide which revenue streams to focus on, where to allot budget and where to cut back, everything. After years of working for other people and thinking “I could do what they do,” it’s liberating and rewarding to finally be doing it.

The downside is that it’s lonely. One thing I miss about working as a salaried employee is the camaraderie and friendships that developed with my colleagues. Victories are sweeter when they’re shared, and losses are easier to deal with when you’re supported by a team.

The main thing I do to overcome that is to keep my wife in the loop about what I’m doing on the blog. She works in a different industry and doesn’t fully understand everything I do, but having someone to talk to about the ups and downs of my business is so important.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

The biggest surprise for me is how hard it can be to carve out time to actually work on a blog post. When I used to fantasize about what it would mean to be a self-employed full time blogger, I imagined blocking out huge chunks of my calendar where I could just write for hours on end. But as with any business, there’s so much more that has to be done. Like all business owners I’m constantly returning emails, and putting out fires, so carving out time to actually do the work itself is more of a challenge than I expected.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so, how did you overcome it?

There were many moments when I thought about quitting, especially in the early days when I was putting in a lot of work and literally seeing no income come in as a result. The main thing that kept me going was the fact that I already had a “real job” and was doing this as a side hustle. I had a job that I didn’t really like, but had to do because it paid the bills, and a hobby I absolutely loved, but that didn’t make any money. What kept me motivated was the idea that if I worked hard enough, eventually I could ditch the job I disliked, and just be left with the thing that I love.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One way that I monetize my blog is by repackaging my blog posts into books and selling them on Amazon. For my first book, I collected all of the stuff I had written about building self-confidence and put it together in a book that I initially called “Ready to Roar.” I put in months of work, then when I finally uploaded it to Amazon, I went to the site to make sure it was coming up in search results. It was only after I typed in my title that I found there was already a book with a similar title on Amazon — a children’s book about a lion who was literally ready to roar. Needless to say, I changed the name to avoid confusion, but it was a good lesson in why competitive research is so important.

Who has inspired or continues to inspire you to be a great leader? Why?

My grandfather has always been a really inspirational figure. He was born in 1929 and grew up in the Depression, where he learned the value of hard work. His life has been devoted to working hard, working smart, and supporting his family — in addition to being one of the most successful people I know, he’s also one of the most generous. And he did it all while dressing well and looking sharp, too.

How have you used your success to make the world a better place?

One decision I made early on was to focus not just on helping guys look good, but on helping them feel good. To me the real value in dressing well and improving your looks is the boost of confidence it can give you, so every time I write about style or looks, I infuse it with self-improvement and personal development advice. That way, as the blog grows and reaches more people, I’m not just helping my readers become better-looking, I’m helping them become better, full stop.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. I wish someone had told me to follow my passion first, and profit second. I wasted a lot of time oscillating between various ideas, debating which ones might be more lucrative, only to see them fizzle out. If I had just pursued my passion from the get go, it would have provided me with a path to profitability that was both shorter and more authentic.
  2. I wish someone had told me what the impostor syndrome is. For years I thought that I couldn’t start a successful style blog, even though I had all the knowledge and skills I could need. I didn’t realize it, but for a long time the biggest obstacle to my success was me.
  3. I wish someone had told me that stability and a salaried job are not the same thing. For a long time I was afraid to make the leap from my full time job to pursuing my blog full time. But in hindsight this was just fear of the unknown; I was over-valuing what I knew at the expense of what could be.
  4. I wish someone had told me how much you can learn about business by reading books. I used to be so intimidated by people who had business degrees, and assumed that I wouldn’t make it very far without one. But developing a reading habit and focusing on the right books has helped me gain both knowledge and confidence, and made me realize that you don’t need fancy degrees to succeed, you just have to commit to continual learning.
  5. I wish someone had told me that the first five years of being an entrepreneur are always the hardest, no matter what industry you’re in. It would have been so much easier to cope with the stress and persevere through the struggles if I knew that they were normal, and something that everyone experiences.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

If I could inspire a movement, I would want it to focus on rationality. So many of the problems we face stem from a denial of logic, reason and evidence. From climate change to vaccinations, we could solve a lot of problems if both our leaders and our neighbors were more willing to reject unfounded ideas and be guided by sound, evidence-based reasoning.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

One of my favorite quotes is attributed to Winston Churchill: “If you’re going through hell, keep going.” I found myself quoting that phrase often during the early years of my entrepreneurial career, when I was toiling away at the blog without seeing any immediate return on my time and efforts.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

If I could have a meal with one person in the world, it would be author, podcaster, philosopher and scientist Sam Harris. His work has been instrumental in shaping my thinking, and I admire his moral philosophy and commitment to honest, open and respectful dialogue.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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