Embrace Delegating. Another consequence of an entrepreneur’s independent streaks is that we try to do everything ourselves. But what business do you think is going to be more successful: one built by a single jack of all trades (and master of none), or one built by a team of masters, who each excel in their field? Learn to delegate early on so that you’ll be more comfortable doing it as you scale up, and the stakes get higher.
Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Dave Bowden.
Dave is the founder and owner of IrreverentGent.com, a men’s style and lifestyle blog dedicated to helping guys lead lives of style, strength, esteem and enjoyment.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
My educational background is in journalism. I worked as a magazine editor for about four years before transitioning into content marketing when I got a job with a travel company, running their travel blog. That job was great and I discovered that I had both a passion and an aptitude for blogging, but travel was more of a passing interest than a passion of mine, and I never quite felt fully comfortable there.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
At the travel blog, my job was to create blog content that would attract readers, some percentage of which would end up making an inquiry and go on to book a trip with the company I worked for. Creating those blog posts was a slog because I didn’t know much about the places I was writing about, so each one required a ton of time and research.
Eventually, I started to realize that if I could write about something I knew about and was interested in — like menswear, fashion and all things style — then not only would the process be faster, but the content would be of a higher quality. I toyed with the idea of starting my own style blog as a side hustle and registered the domain, but didn’t do too much with it at first. The kicker came one day when, in one month, the blog posts I was writing for the travel company resulted in three bookings, each one of which was worth more than my annual salary. At that point, I realized that writing a blog is a skill I could get paid for, but owning the blog is a lot better.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
I was not a natural entrepreneur. I’m very risk-averse, so the idea of quitting a salaried job to start my own venture — even one with as few barriers to entry as blogging — was quite terrifying. But after I started building the blog as a side hustle, something funny happened. I was doing very similar work — writing blog posts — in the side hustle as I was doing in my day job. But the side hustle was way more fulfilling, and I became addicted to the thrill of having full control over both the creative and business decisions. Pursuing both an entrepreneurial path and a safe, salaried job in parallel made me realize that I’m much more drawn to entrepreneurship, and eventually, that pull was just too hard to resist.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
My grandfather was an entrepreneur, and he’s always been a huge source of inspiration for me. After working as a car salesman for years he took out a loan and opened his own dealership, which was a huge risk at the time — he had never even managed a business, nevermind owned and operated one. But it paid off spectacularly well for him, and he’s been able to support his family for three generations now. He worked hard, but he did it on his terms, which I always admired. For instance, he would wake up each day, read two newspapers front to back, then arrive at the dealership around 10 am, better informed and better rested than anyone else there. That kind of freedom was inspiring, and something I’ve always sought.
What do you think makes your company stand out? Can you share a story?
I had been reading men’s fashion blogs for years when I started mine, and I knew from the get-go that I wanted to inject a sense of humor into everything I wrote because so many of the men’s blogs I read were so stuffy and self-serious. Early on I got an email from a reader who said he found my blog on Twitter and clicked through expecting to learn about how to wear a suit, but ended up having to try and stifle his laughter because he was reading the blog in his open-concept office when he was supposed to be working. That was when I knew I was on the right track.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
The first is refusing to let the good be the enemy of the great. My job at the travel blog was good by any objective measure: good work, good people, decent pay, lots of perks like free travel. But I knew in my heart that it wasn’t for me, and that I would only have a great career if I had the courage to leave and follow my passion.
The second is grit. Starting a business hard, especially in the early going when you have no money, no audience, no customers. Just showing up and putting in the work can be hard when you don’t see any return, so you need determination, perseverance and stubborn persistence to keep grinding until you eventually attract attention.
The third is vision. It’s a lot easier to exercise grit and determination if you know what goal you’re ultimately working towards. Things change and you have to remain adaptable of course, but in entrepreneurialism the old adage is true: if you don’t know where you’re going, you’ll never get there.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Early on when I started my blog I followed some internet entrepreneurs who said that the key to having success online was “niching down.” I knew I wanted to start a men’s style blog, but in the opinion of these so-called experts, that seemed too broad and generic. So I tried to “niche down” and make the blog even more specific: what if it was about using style to build self-confidence? What if it was lifestyle advice for shy or introverted guys? What if it was a humor blog that also gave style advice? It took me far too long to realize that these were all distractions. I had a clear vision for what I wanted the site to be, but I spent years denying it and trying all sorts of other directions. In hindsight, I wish I had just stuck to my vision and built towards it from day one because I’d be a lot further ahead today.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
Give employees as much freedom as you possibly can. Having a lot of work to do under tight deadlines is always hard, but when you feel like you have to get it done because you have a boss breathing down your neck, it’s that much worse. But having a pile of work to do feels a lot less overwhelming when you have the autonomy to tackle it your way, and the freedom to set your own priorities.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Be as transparent as possible without giving away trade secrets or proprietary information. For instance, in my industry, we’re often offered free products in exchange for writing a review of that product. There’s a temptation to take the free stuff, then write up the review as if you had actually purchased it and had no business relationship with the company that provided it. But by being honest and transparent right up front, you show the reader that you’re credible and trustworthy, and allow them to make their own decision about how big a grain of salt is needed while they read your review. Ultimately that builds a lot more credibility than an advertorial posing as an editorial review.
Can you help articulate why doing that is essential today?
People are savvier than ever and good at sussing out what’s authentic and real from what’s fake or manufactured. When it comes to my industry specifically, they also have more options than ever. It used to be that if you wanted editorial advice about men’s style, Esquire and GQ were basically the only games in town. Now there are dozens of great men’s magazines and websites covering the same ground, so if you give off an inauthentic vibe, readers are likely going to ditch you in favor of a more sincere option.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
One of the biggest is spending too much money too early, and quickly going broke. It’s so tempting to look at your competitors, who have been in business for years and feel like your small potatoes by comparison. So you spend lots of money on an ad campaign or a website that makes your company look flashy and slick like your competitors, but you don’t yet have the infrastructure and business systems in place that are going to turn a profit and live up to the image you’re projecting.
The best way to avoid this temptation is to have a sound, solid and well-thought-out business plan. It’s a lot easier to swallow the fact that you’re currently smaller than your competitor if you have a clear plan for growing, understand what stage you’re currently at, and know exactly what steps you’re going to take to achieve your goals.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
One reason why you’ll always have highs and lows — and this is unique to entrepreneurship, in my experience — is that you constantly move the goal line and redefine what “success” means. When you first start out, your goals are often modest, so the highs come quickly. But as you move forward and become more ambitious, you continue to set goals that are further into the future or harder to achieve and become fixated on getting to the next level. So the highs keep getting higher, but they also keep getting more daunting, presenting challenges and a lot of lows along the way.
The other thing that brings about highs and lows is that, as an entrepreneur, you’re so much more invested in your work — in every sense of the word — than you are in a “regular job.” When you start a company from scratch it feels very much like it’s your baby, so the highs are highers and the lows are lowers because it’s difficult not to take them personally. This makes entrepreneurship more of a roller coaster than working at a regular salaried position, but ultimately much more fun and rewarding, too.
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
In the world of blogging, there are certain ad networks that pay better than others, but the very best ones require a high level of traffic and high quality of content in order to be accepted. For a full year, my sole goal was to build up enough traffic to get accepted into one of these networks, and just as I was approaching the minimal threshold for being accepted, they doubled their traffic requirements and made it significantly harder to get accepted. I was deflated but not deterred, so I born down and basically doubled my output, cranking out as many blog posts as I could in an effort to reach the new threshold. I managed to double my traffic in six months, and when I got the email saying I had been accepted into the network, I literally screamed — it was easily the most rewarding professional accomplishment of my life. That night my wife and I toasted with a bottle of champagne, and nothing’s ever tasted quite that good.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
I once spent months working on an online course that I was going to sell to my email subscribers. I spent weeks plotting it out, designing various modules and lessons, and put a lot of time, energy and thought into every aspect of the course. In addition to the course itself, I built out an email series announcing the course and teasing out its various elements, to try and entice people as much as I could. Then, when I finally launched it to my list of 1,000 subscribers, not a single person signed up. It was a devastating blow and resulted in a lot of self-doubt on my part. “Maybe I don’t have what it takes to be an online entrepreneur. If I can’t actually convince people to buy anything from me, then how am I ever going to succeed?” I was pretty crushed, and my mind went to some dark places.
Based on your experience can you tell us what you did to bounce back?
After the debacle with the course, I refocused on my core strengths. At the end of the day I’m a blogger first and foremost, and a marketer/salesperson (a distant) second. So I doubled down and focused on creating the best possible blog content that I could, which reinvigorated me creatively. And as so often happens, when I stopped worrying about “diversifying” or figuring out how to milk every last penny from my audience and started focusing on how I can best serve them, I started making more money. It was a great reminder that, in business and in life, the best way to get value is to provide it.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
When I failed to launch my course I briefly considered giving up entrepreneurship altogether, but I was bolstered by the fact that I had read a bunch of business biographies, so I knew that everyone experiences failures. Educating yourself as much as possible about the entrepreneurs who have overcome obstacles in the past will help keep your own ups and downs in perspective.
2 Moral Support
Entrepreneurs are rebels by nature, but no matter how independent you are, you always need someone to talk to. For me, that person was my wife. Even though she works in a completely different industry and doesn’t understand the exact challenges I face, just having someone who would listen and provide an encouraging word was incredibly valuable and important. I think it’s fair to say I would have given up many times if not for her support.
3 Embrace Delegating
Another consequence of an entrepreneur’s independent streaks is that we try to do everything ourselves. But what business do you think is going to be more successful: one built by a single jack of all trades (and master of none), or one built by a team of masters, who each excel in their field? Learn to delegate early on so that you’ll be more comfortable doing it as you scale up, and the stakes get higher.
4 Commit to Continuous Learning
There are only two types of entrepreneurs: the kind who commit to continually learning, growing and evolving, and the kind who fail. Entrepreneurship requires you to wear a lot of different hats and tackle a lot of problems (often simultaneously), and you simply can’t do it all if you don’t continually learn new things and develop new skills.
5 Learn How to Rest and Recharge
Because the stakes are so high — financially, professionally, emotionally — most entrepreneurs are workaholics. It can be difficult to turn your brain off, stop trying to problem-solve or mapping out your future and focus on something other than work. But it’s vital that you do. Not only does stepping away give you a chance to rest and recharge so you can come back stronger, but more importantly it reminds you that there’s more to life than business.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
To me the most resilient people are the ones who know what they’re working towards. When you have an end goal in mind that’s personally motivating, it’s a lot easier to dig in, persevere and be resilient. The keyword there is personal. One of the things that separate entrepreneurship from normal jobs is that there’s so much more on the line for the entrepreneur. An employee can just quit and find a new gig elsewhere, but for the entrepreneur, there’s so much pride and personal reputation wrapped up in their work. Focusing on what’s at stake — and even more importantly, what that means to you — will make you more resilient.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
I once had a salaried position as a junior magazine editor at a trade magazine. One morning I got a call from my mom — my aunt was in the hospital, having emergency brain surgery. Doctors had discovered a tumor the size of a grapefruit in her brain and were trying to remove it. I called my boss but he didn’t pick up, so I left a message saying I wouldn’t be in that day because I had to be with my family at the hospital. I could have lied and said I was sick, and he never would have been the wiser, but I was honest.
When I went back the next day, my boss reprimanded me for missing work — gently but in no uncertain terms. An aunt, he said, was not a close enough relative to justify missing work for. That was the day I knew I never, ever, ever wanted to have a boss again. Now, when things get tough and entrepreneurship seems risky, I sometimes find myself feeling tempted to go get another “safe” salaried position. But then I think back to how I felt when I was told that working at some tiny trade magazine was more important than supporting my family through a crisis, and I find myself resilient enough to weather any storm.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
This may sound strange, but one of the things that helps me get through tough times is thinking about my paternal grandfather, who I never met. I’m named after him, and I’ve always felt a certain kinship with him, even though he died long before my dad even met my mom. He fought on the front lines in WWII and was away from his family for five full years fighting in Europe. So whenever I’m faced with a challenge, I remind myself: “The last guy from my hometown named Dave Bowden went through much, much worse for much, much longer, and came through the other side. Whatever it is you’re going through, it’s not worse than what he went through, and it won’t last as long.” When I frame my challenges that way, keeping a positive attitude gets a lot easier.
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Positive attitudes are infectious no matter who has them, but when it comes from the top, positivity is also inspiring. Employees of an organization know that they don’t have all the information — the marketing team doesn’t have a close view on finances, for example, and the HR department may not know exactly how close the company is to its sales target. But everyone knows that the President or CEO does know all of that, so when they see that person adopt a positive attitude, they take it as a signal that there’s a lot to be positive about.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
The single quote that motivates me to achieve as much as I can is the famous line that’s often misattributed to Aristotle: “We are what we repeatedly do. Excellence, then, is not an act, but a habit.”
Everytime I want to cut corners, or make excuses, or skip out on doing what I know needs to be done, I repeat that phrase out loud to remind myself that I’m not just choosing what to do, I’m choosing who I want to be. When you start thinking in those terms and associating your actions with your identity, motivation becomes a lot easier to find.
How can our readers further follow you online?
The best place is my website, Irreverent Gent: https://www.irreverentgent.com/
This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!