Build your business at all costs. Be smart, don't sweat the small stuff and don't try to have all of the best and coolest tech on Day 1.

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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.

Starting up again, means doing it all over again

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.

A couple of weeks ago I joined AngelList hoping to get into the angel investment scene and diversify my own business interests (as well as meeting new people and having stimulating / challenging business conversations about their work). I've had a couple of introductions to startups which I thought had some traction, but to date I've resisted pulling the trigger on any of the deals, as I've decided to err on the cautious side.

Bubble or no bubble, I'm not convinced of either of those ends on the spectrum. This article published by the Economist last week introduces a new "bubble theory", one which resonates more with my own thoughts than the alarmist articles that have been published recently.

Here are my concerns:

1. Funding supply is exceeding the demand, which is driving higher valuations. Angel investment has indeed become sexy and - dare I say it - moved into the mainstream. Heck, I'm quite connected and I read a lot, but it's only in the last couple of months that I've taken notice of angel investments to the extend that I'm intrigued enough to get involved. More angels obviously means that valuations are being driven up and I'm not sure that all of these valuations could ever be sustainable.

2. Valuation techniques / models are shocking. Talking about valuations, I recently quizzed a startup founder on how they decided the valuation of their business (for the purpose of raising some funding). He said: "We want to raise $200k and for that we're willing to part with 10% equity. So this values our company at $2m". A little crude IMO (especially since this was prior to $1 of revenue)... I'm no investment expert, but I did my fair share of business valuation models during my Honours Degree and this kind of valuation is risky at best.

3. The Exit Culture. At this kind of pre-revenue valuation, how can I ever earn a proper ROI on my angel investment? I need to hope that the company is valued at a higher level in a subsequent funding round or I need to hope that they get acquired somewhere in the future, in which case I'll probably be rich. Alternatively I need to hope that revenues eventually justify that valuation, which is a gamble at best since your guess is as good as mine when - and if - that will happen (as there's no supporting evidence pre-revenue).

4. Closed Focus. It just seems that so many startups are targeting the same kind of tech-savvy demographic, which suggests that we'll eventually reach a saturation point in the appetite of this demographic to try something new (which in actual fact is only a slightly different spin on something else they've been using until now). This approach is very gimmicky and I highly doubt that we'll continue to see $1m-in-sales, overnight iOS app successes as much as we've seen them until now.

None of these concerns, invalidates either angel investment or the tech / startup community at the moment, but they most definitely make me think twice about make any investment at present. I know that there are a lot of angel investors - especially those that have access to the best deals in the Valley - that will make an absolute killing for pulling the trigger now, but that is most definitely easier, when you can make 10-odd sizeable investments & in the process you're hedging your own risk (based on the assumption that you're actually making good investments).

Unfortunately I'm not in that position to take a 10-deal kinda risk on our personal finances at present and I thus need need to be much more selective about the investments that I do make.

I love the description of a startup above and agree wholeheartedly with Eston’s views on why titles actually do not matter.

This is a similar approach to what we have at WooThemes, where we’ve never been overly fussed about titles and specific job descriptions. And the only reason why I didn’t write such an article, is because I’m not nearly as eloquent as Eston, who manages to write an extremely intellectual article on the matter. :)

If these guys don’t rely on banking fees to make money, I’m *really* curious to see their revenue model.