A couple of weeks ago I was wondering out loud whether I might just be a one-hit wonder. The fact that I did not share at that time, was that I had already made the decision to close down Radiiate (my 2nd business after WooThemes), after it didn't grow / evolve in the direction I had hoped.
In this post I'd like to share my experiences in trying to start up another business, especially given the context that I had done it before (and am still doing it) with WooThemes.
1. (Most) Serial entrepreneurs do it sequentially
This was probably the biggest take-away after the whole experience (well said in this comment): it is just not that easy to commit completely do doing a new startup while I was still committing close to 100% of my time to another business. I just did not have the time or mental energy to power through the initial startup phase and I ended up making it really hard on myself in the way I was constantly pulling myself in two different directions.
My problem was compounded by the fact that I was doing this solo (i.e. without cofounders), which meant that I was exclusively responsible for the strategic direction & decisions. Things might've been different if I had cofounders that could've at least shared this responsibility with me.
2. Too many shitty ideas
When I cofounded WooThemes, it was my best idea at the time. I can remember either Jason Fried or DHH mentioning in an interview that if they ever sold 37Signals, they would be selling their best idea and that in turn would mean their subsequent startup would be their second best idea. So with WooThemes, this was easy: we had the idea, believed that we could execute it and worked hard at doing just that.
With Radiiate things were much different though... The day I decided to reboot Radiiate, I did so because I wanted to be involved in a startup and I wanted to stimulate & challenge myself with a few side projects. So I didn't do it because I actually had a "best idea", heck I didn't even have a good idea (debatable). What I did have was a couple of experimental ideas that I was hoping to trial. Ultimately none of these panned out as hoped and after various pivots, I decided to throw in the towel.
I know for a fact that if I had the idea before the business, things would've been very different. Having loads of experimental (and shitty) ideas definitely didn't help in this regard and in fact, it was far removed in principles of MVP, lean startups & bootstrapping.
3. Money is the root of all evil
I cofounded WooThemes while I was still employed full-time and we started the company in the classic bootstrapping + DIY fashion that is so popular. We grew the business organically from there, kept expenditure down as long as possible and even resisted office space for the first 6-odd months (preferring to work from home). This was as close to being the perfect startup model as you'd get (which resonates with the success we've had almost 4 years down the line).
Radiiate though was far removed from that model, because this time around I had accumulated enough capital, the (WooThemes) office was settled (so Radiiate could just work from there) and instead of being DIY, I had hired a team (read: expenditure). The lack of bootstrapping, DIY and my strategic involvement, meant that trying to grow organically was near impossible and the money made it easier to not face the reality (of changing things around or stopping alltogether).
4. Team composition & experience is always integral
I say this with absolutely no disrespect to Cobus & Marie (the Radiiate team), as they did an incredible job throughout and I believe they're going on the bigger, better things now.
If I had to do this all over again, I would've definitely hired more experience to be more of a guide to Cobus & Marie. I had originally hoped that I could be that guide, but ever since I became the "business guy at WooThemes", I had lost my technical knack and thus couldn't be much of a guide / help with those things.
I also regret not hiring a hardcore developer to compliment the extreme design & front-end talent that we had in the team. Various projects fell of the wayside, because we didn't have a developer in-house (multiple colabs didn't pan out) and by the time I decided to try hire someone, the expense thereof was just to significant to warrant another "pivot" (which would've delayed the decision to shut Radiiate down).
5. I don't want to be a solo founder
There must be a reason that Y Combinator prefers multiple founder teams... Duh... :)
I truly doubt that I will ever again attempt to put something together on my own; just having someone with the same, vested interest in the success of the startup means more than most can imagine. Having a cofounder to discuss problems with and having them help out with the load (especially in terms of the strategic & leadership stuff) is invaluable.
Ultimately I think I defied my own recipe when I started Radiiate. There was nothing wrong with the idea - in principle at least - or the passion behind the whole thing, but I guess my previous success made me arrogant / ignorant to a certain extent.
I lost quite a chunk of money trying to start this up and that is a punch that I've had to take on the chin. Whilst I doubt that I'll be doing a fully fledged startup in the short term (at least to the point where I'm not involved daily / operationally with WooThemes anywhere), if I had to do so, I would focus my attention on doing it properly and truly starting up again.
This means no luxuries in terms of cash or not having to be DIY; it would be back to square one and into the trenches. There really is no shortcuts to starting up a new business. I tried to take a few and got burned subsequently.