We were lucky to catch up with Harris O’Malley recently and have shared our conversation below.

Hi Harris, thanks for joining us today. Almost all entrepreneurs have had to decide whether to start now or later? There are always pros and cons for waiting and so we’d love to hear what you think about your decision in retrospect. If you could go back in time, would you have started your business sooner, later or at the exact time you started?

In theory, it would be nice to have started my career earlier – especially since it would mean I would have had more time before industry-wide issues in publishing were triggered by Facebook’s push of video content, restriction of reach for professional pages and other changes – I literally couldn’t have.

I fell backwards into writing an advice column and into coaching people on how to date better and have happier and more successful relationships. Prior to hanging out my metaphorical shingle, I was trying to make a go at being a professional illustrator and comic artist. It wasn’t until I was devoting more and more of my time to writing that I was able to finally admit that I had neither talent nor passion for illustration, but was actually pretty good at this writing thing.

But while I wasn’t ready to shift my focus onto writing, I also was not in the right place in my life to actually be the coach and columnist i am today. If I had started earlier, my work would’ve been significantly different, more bogged down in myths and misunderstandings about gender, sexuality and romance, and far more toxic.

Since so much of my work is based out of my own personal experience in dating, I wouldn’t have been in the right place to give advice. I needed to grow, mature and – importantly – learn and UNlearn a lot before I was ever in a place where I could give other people useful advice on how to fix their love lives.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I, for all intents and purposes, carved out my own niche in the advice industry, and I never set out to do so.

I struggled with dating and relationships for most of my life; I had no idea how to approach or talk to women or how to flirt with them or spark their interest in me. This was made worse by the fact that one of my best friends was not only a shockingly good looking man but genuinely one of the nicest people around and he would attract women the way cheese attracts mice.

My desire to try to solve my dating woes eventually lead to my falling into the nascent pick-up artist scene in the mid 2000’s. After studying under some of the biggest names in the PUA community, my success at meeting women went through the roof… but at the cost of my emotional and mental health, as well as my relationships outside of the PUA scene. It was only a series of realizations – I was spending all my time at bars and clubs, I was sleeping with people I didn’t actually like, I hadn’t seen my non-pick-up friends in months, didn’t have conversations that WEREN’T about picking up women and so on – that I left the community.

However, since I DID enjoy the success I’d been having, I wanted to know if there were some way that I could continue meeting and dating incredible women… just in ways that weren’t coercive, toxic or manipulative. This sent me into a frenzy of research as I studied everything I could get my hands on about human sexuality, gender roles, social issues, the history of dating and so-on.

During all of this, I was part of a pop-culture podcast called The League of Extremely Ordinary Gentlemen. During the run up to the release of the movie “Scott Pilgrim Vs. The World”, we recorded an episode we called “The League Vs. Our Evil Exes”, all about relationships. We talked about our past relationships and answered listener questions about love and dating. As the League’s resident man about town, I took the lead on answering questions, and the episode was a huge success.

In fact, it was SO successful that we did a similar episode for Valentine’s Day the next year. Since we didn’t get to all of the questions our listeners had sent in, I took the remainder and answered them after the episode. As soon as I did so, our listeners submitted more questions for me.

I realized that I had an opportunity here, quickly put a website together and began to publish my responses. And in that moment, Dr. NerdLove was born.

How did you build your audience on social media?

I had the advantage of starting out with a pre-existing audience. I was part of a popular podcast that spun out from an equally popular movie review site. When I started my blog, not only did I have readers who were already familiar with me, but my friends on the podcast would promote me, both on the podcast and online.

This gave me a significant head start, which I will always be grateful for. Over time, I found that building up mutually supportive relationships with other people online – both established presesnces on social media and up-and-comers – made it easier to grow my audience. Similarly, working with some prominent media blogs like Kotaku and the Good Man Project, making podcast appearances and getting my name out there helped immensely.

I also have found that having an engaging and entertaining presence online means that people are more likely to share my work with their friends – including the occasional random observation or joke that ended up going absurdly viral.

What’s worked well for you in terms of a source for new clients?

My best source for clients has been word of mouth. As someone in a relatively niche industry, and one that’s full of grifters, toxic personalities and people who trade on the worst impulses and beliefs about sex, relationships and women, I stand out as – as one of my clients calls me – a positive influence and breath of fresh air.

Because I offer sex-positive advice, push back against toxic and restrictive forms of masculinity and can speak to my audience in a language that they understand, my readers and clients are among my greatest advocates, and are the reason I’ve had so many wonderful opportunities over the course of my career. I can’t count the number of new clients who’ve come to me because their friends or family were familiar with my work or because influential voices in various industries had read and enjoyed my column and directed their audiences and peers my way.

I, quite literally, couldn’t do it without them.

Contact Info:

• Website: doctornerdlove.com
• Instagram: @drnerdlove
• Facebook: facebook.com/DrNerdLove
• Twitter: @drnerdlove
• Youtube: youtube.com/user/DrNerdLove