Part 1/2: Top 10 Ways to Kickstart Your Blog…and Also That Time My Ex Cheated on Me with an Entire Soccer Team…

Between 2006 and 2012, I wrote nearly 1,600 posts on a blog that has been visited more than 2.1 million times. I had an average of 50,000 myspace ‘friends’ who found their way to me mostly due to clicking a link from that same blog. I interviewed people like Margaret Cho, Roseanne, Tegan & Sara, and Missy Higgins and they’ve all been on the covers of my very own lesbian-friendly print magazine. I have been featured in Curve magazine 3x, was once invited to host Colorado Springs PRIDE, and have been recognized in person by countless readers from around the world.

I’ve even been in a gay parade. Hell, I AM a gay parade…

In this series of Medium posts taken from a mini (micro) ebook I published a while back, I’ll share 10 ideas for having a successful and fulfilling blogging experience, no matter what your blog topic, target audience, or goals may be. The more I review these tips, the more I realize that they can also be applied to startup founders and investors who want to shape their online *voice*.

Women: can’t live with em, can’t…stop them from cheating on you with an entire college soccer team.

I get dozens of messages per week, and 50% of them are from aspiring bloggers asking me how I started my blog, and for advice on starting their own. Over the years, through thousands of hours of writing, researching, and experimenting, and through trials and tribulation, failure and success, I have found a few consistent pointers that have helped me with my blogging and that I have shared with others to help with their endeavors. The next 2 posts will give you some of the major tools you’ll need to get started (or at least the inspiration to continue).

First, a little background on my blog, Your Daily Lesbian Moment — today a parking lot mostly, but in its heyday, twas the bomb. In early 2006, my girlfriend of 3 years — a truly lovely person who is NOW one of my best friends in the entire world — ripped out my heart, then broke it into a million pieces, then peed on it, then set in on fire, and then stomped out that fire, all while I watched helplessly from the ground where she’d left me. I was left in a cesspool of decay and unyielding regret. Yep, your typical lesbian breakup.

Right around the same period, a personal and business venture that I had taken a leap of faith on in a HUGE way had gone belly up after years of investing my money, blood, sweat and tears. So there I was heartbroken, alone, and destitute, in a ramshackle apartment perched atop a not-so-nice neighborhood — and when I say ‘not-so-nice’ I mean wretched, dangerous and scary.

Bankrupt — both emotionally and financially — and just a silly mess of a person, I did what anyone would have done in my situation: I drank a gangload of wine and made an emo singer/songwriter friend of mine listen to my drunken sad stories for hours on AOL chat. I believe it was during the time where I still had a dial-up modem.

I went to bed a drunken wreck and woke up a hungover wreck. I remember sitting at my computer again, staring blankly at it. What now? Internet pornography? Naw, it would just be too much of a let down in the end. Should I follow through on my idea of throwing all of my ex’s clothes down the stairs and inviting the neighborhood kids over for a free for all? An ‘All You Can Grab Off the Lawn Is Yours’ party sounded pretty radical. ‘Yes Emmanuel, if you can fit those knee-high Vera Wang boots in your backpack, they are YOURS. No questions asked.’

When the realistic toll of those beautiful ideas started to come to light — having to move, get up, or talk to Emmanuel— I vetoed them and decided instead to do whatever I could do that was within arm’s reach. Hmmm…well there’s that newfangled site Youtube that has a whopping 100,000 or so videos I could choose from…there’s GOT to be something lesbionic on there that could distract me long enough not to want to call the ex and leave yet another crazy 5 minute diatribe, right? Right.

I found something. Can’t remember what it was to be honest, but I’m pretty sure it was either two women making out, or two women making me laugh. Those were the only two things back then that could cheer me up (not so different from today, really), so I’m certain the very first vid I found included one of the two, or maybe even both. It did the trick and I felt slightly better for a moment.

After watching it, I thought I’d pop on over to my myspace page and make a little blog about it so that 5 other people could see it, too. I believe at the time I had 1000 myspace friends or so. This would be my way of staying connected with other human life without having to actually go outside, speak out loud, or ya know, put on pants. It was perfect.

Maybe it was the fact that SO many people can relate to being heartbroken. Or it could be that my way of expressing myself in the little paragraph that proceeded the video embed tickled someone who then wanted to share it with a friend of theirs who was going through the same thing. Perhaps it was because there weren’t that many people talking about gay lady issues at the time in the way that I was. Or ya know, it coulda been that the vid WAS of two girls making out. But whatever it was, something clicked. Just a few hours later, I had dozens of views on a personal myspace blog (back when even the word ‘blog’ still felt foreign to most) that a day earlier had only been viewed by a handful. Then a few hours after that, hundreds of views.

Friends would tell friends, and then just like that shampoo commercial from the 80s or whenever, things just got outta hand awesome. Thousands of views in a week, hundreds of friend requests, dozens of messages, and so on. After a few weeks I decided to open a account and make this thing legit and more organized. August 2006 was when my first official blog posts appeared on the new site. After that, things got even crazier and cooler and sexier — as if TLC themselves were in the mix. Shout out to the 90s, yeah!

“Figure out what you think about something, and then change your mind as often as possible.”

I think that some of the coolest things that have happened so far in my life have been due to happy accidents (including discovering Bob Ross… *sigh*). I’m certainly not the best writer, and as much as I fancy myself to be a serial entrepreneur, it’s mostly because something within me DRIVES me to do so. Not necessarily because I’m all that good at it. What I do have are a point of view, vision, and tenacity. In my neck of the woods, they call that “gumption.”

So the first thing you should do when starting your blog is establish your point of view. Obviously, having a theme — mine being LESBIANS (esbians…esbians…) is incredibly important. But if you’re reading this, I bet you already have an idea of WHAT you’re going to write about. The important thing at this stage, is HOW will you write about it. What’s your angle? What’s your vision and your message?

The answers can be simple or complex, depending on your subject, the type of writer/person you are, and how much time and attention you plan on giving this endeavor. It can also change with time, and be one thing now and something else later. Or in the same day. Or before you hit ‘publish.’ As you read earlier, my blog and its theme started out as a (un)happy accident. But once I realized that it was actually being read by people and that there was an audience hungry for more content, I quickly figured out what my point of view would be. It’s a small decision that will help steer you on your blogging path.

In part 2 we’ll cover:

  1. Establishing your point of view — (above!)
  2. Embracing experimentation
  3. Not being afraid of being ‘weird’
  4. Being YOU, no matter what
  5. Adding value to the readers’ online experience
  6. Being your own hype (wo)man
  7. Being worth the hype
  8. Staying in the loop
  9. Figuring out why knowing NOTHING is a good thing
  10. Having fun with it!

Click to read Part 2/2

I’m the founder and managing partner of Backstage Capital, a seed investment fund that backs high-potential, underrepresented startup founders. I am also a tour manager, currently working with New Zealand Music Award winner Janine & the Mixtape. Not braggin’, but I have been called the “Lebron James” of venture capital (by my brother).

For interviews or to set up one-on-one “office hour” sessions at your event, email with the subject “interview request,” or “conference appearance request,” etc.

Venture Capitalist + Tour Manager for Janine & The Mixtape

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