The Next Venture Raise...

... is always the worst venture raise.

Hey friend,

It feels like a lifetime since we chatted. Yeah, I know it was just last week, but, damn… a lot has changed since then!

Not only did we go live with the private alpha and it’s working exactly as I had hoped — I mean, you can’t ask for more than that, right?

We’ve got real users giving us real feedback on the product that we can weaponize and turn into features that make them happy — this is the holy grail! We’ve closed the gap between customer / community & product design / development!

It feels amazing to finally get something right. I’m on cloud-fucking-nine. And I’m operating on a level that I’ve never felt. Man, it’s like a drug. Glorious.

With this in mind, it’s clear that we’ve got something unique and it’s only a matter of time until we deliver a product that folks can automagically walk into and pay us, the second part being the more important one because the first part is already done and while we haven’t even begun working on the second.

L(° O °L)

Consequently, I’m starting to think about the next fundraise. Ugh. I hate asking for money… historically. But this time feels different… because I know what I have and I know what it’s worth.

And, more importantly, I know the types of people that I want to work with and I’m certain of the types of folks that can go fuck themselves.

This is entirely different than my first fundraise ever — have I ever told you about that? ELLLLL-OOOOOOOOO-LLLLLLL.

Look at these:

To the tune of $25,000! I was the Founder / CEO and had invited three friends to join me as equal partners which, by the way, was a really bad mistake and ended costing me the business — that’s another story for another time.

Anyways, it was really just a grant from Gwinnett County of Georgia, but it was part of their new “Let’s Refresh Gwinnett County Campaign” and part of that was investing in local startups.

We pitched, I nearly puked — even after practicing “power poses” in the goddamn bathroom before — and we managed to sneak a win as having “real potential”. I wasn’t in a good place and was already headed down a poor track with my health — you can see the extra pounds in my face 100%.

We didn’t need the money but we needed the money — does that make sense?

I had ideas about expanding our small product / service shop into a more serious publishing powerhouse. This would eventually be the “seed” capital that we used to build a new business unit, a WordPress-centric “industry / community news” blog that quickly became an industry-leading source that was equally respected and hated.

I didn’t give af because it took only 143 days to cross $3k in MRR — there was no way we could be stopped. Later that year we hosted WordCamp in Atlanta; we we’re hot-fucking shit!

Or, so I thought.

Like I said, the partnership imploded — my fault because I honestly didn’t know what I was doing but I couldn’t retain the IP because I had stupidly given up 75% of the fucking company!

I promised I’d find a buyer for our core product, a once industry-celebrated open-source / premium theme (a $M+ ARR biz!) and the content side and two folks showed up: WPEngine took the content and WooThemes took the product.

And my baby was dead. Done. I was done. It was done. I had nothing. And only because I raised a little bit of money. I loved that company. It had the most amazing branding and my personal twitter is all-bout-about it.

I’m telling you — FUCKING TRAUMA when it comes to raising money. See, you don’t even know! You couldn’t even possibly understand: I moved my family into one of my partner’s basement for a year to get that company off the ground.

3 humans lived in a basement to get a WordPress-centric business off the ground — what in the serious fuck. Of course, I blogged it when I arrived and my family finally moved out. And, it hurts my heart to think what I put my wife through during that time.

I’m telling you, I’m the luckiest man alive.

Oh, wait. Then, we had our second kid. And it became 4 humans living in a basement.

Ugh. I was so confused back then. I was giving keynotes at industry-events, hosting events in my decked-out office in downtown Atlanta and yet I was driving home to a poorly-lit basement where I had left a young mom by herself to take care of two very young kids with zero cash.

Iiiiiiddddddentity issues, yo. Priorities. Focus. It was all out of whack. Why? Because, money. It fucks you. It totally fucks you. That’s why it’s never been about the money, because, it has literally destroyed my life…

… and that’s when I wasn’t even looking for it.

To infinity & community,

— john