This is the second post in my "Bootstrap Mondays" series. Read last week's post, Revenues & Momentum is Everything, first.

Bootstrapping obviously works best when you don't have loads of expenses & overheads burdening you down. One of these expenses that seems unavoidable in a startup, is marketing-related expenditure.

Regardless of what you classify under marketing, most of your options (PPC, Banner Advertising, PR etc.) will cost you something. The free alternatives are obviously viable, but they rely on significant word of mouth / viral traction, which in turn is only achieved if a couple of stars align for you: you have an amazing product, the way you first pitch that is perfect and your timing is spot-on. Whilst I wouldn't necessarily say that you only have one shot at this, it does sometimes feel like that; fuck it up and you might as just well move onto the next idea / project.

I did this a little bit differently when I launched the first product that eventually became WooThemes.

Reputation is free

Unlike these days, I used to have a thriving blog back in the day (probably due to being a relatively early adopter and the fact that everyone & their aunt has a blog nowadays), I blogged a lot and had a prominent voice within the WordPress community. I spent a lot of time making sure that I was being heard (sometimes controversially so) and I shaped my personal reputation & profile around that voice.

For better or worse, this culminated in the "Adii - WordPress Rockstar" moniker that I labeled on top of myself and people knew me as a result. (As I said: for better or worse… In hindsight I know that even though I probably seemed arrogant to many people, at least I had their attention…)

This meant that I had an audience; one that I had cultivated because of my reputation and the work that I put into building an online profile. I used my blog to do all of the marketing for my first ever product. I didn't have to pay $1 to get my message to my target audience; they were already there.

This is how you do it now

Sounds a bit like pipe dreams? Maybe… I'm the first to admit that it is hard to have a thriving blog these days and have seen a decrease in my own blog's traction since those earlier days. But I think there are other ways to build your reputation these days:

• Make friends & be easy to find. Yes, this means you'll have to interupt work every now & again to be active on Twitter for example, but that is where you connect with like-minded people that could be part of your eventual target market. Become known for something, so that people looking for someone like yourself are easily able to find you.
• Augment your online profile. If you're a designer, you need to be on Dribbble. Similarly, if you're a developer without a GitHub profile, then you're doing it wrong. Share your work. Connect with others through that work.
• Have an opinion. The person in the corner of the room that keeps quiet the whole time doesn't get any attention. Make yourself more visible and heard by commenting on blogs or across social networks. Be unique when shaping your online voice & share your opinion with humility (something I only learnt later on).
• Get noticed. The trickiest bit is to get attention the first time; thereafter it becomes easier for subsequent attempts. Get onto the homepage of Hacker News by writing a great blog post or sharing something cool you've built.

Your Strategy Simplified

Building your reputation & online profile is free. This is also the perfect foundation to launch a new business.

By doing all of this, you don't necessarily get closer to your target audience, but you do come onto the radar of influential people that will help you spread the word when you eventually launch your product / service.

For the next couple of weeks, Mondays will be "Bootstrap Mondays" on the blog & I'll try to share some insight into how we've bootstrapped WooThemes to the size & significance it is today.

Way back in 2007 (2 November 2007 to be exact) when I first released the original product that lead to me meeting my co-founders and us launching WooThemes, I wasn't thinking about bootstrapping nor any type of VC investment. Not that I hadn't come across either of these terms / activities before; it was just a case that neither was very relevant: I was generating revenue from Day 1.

Years later, having established a 17-person, strong team, 130 000+ customers and a multi-million dollar revenue business, I look back fondly on how we managed to bootstrap our business and grow it organically to the significance it is today.

The irony is however that we never made a conscious decision to bootstrap the business, yet this probably ranks as one of our finest decisions to date. Our ignorance in this regard is probably somewhat down to our relative inexperience in terms of running a startup back then, but I'd like to think it was mostly down to one thing: we had revenues (and thus profits) immediately after launch, which meant we didn't need to figure out a way in which we would fund the growth of the business.

Revenue: Impossible

I hear you reading the above and thinking "Well… That's all fine & dandy, but being revenue-positive from day one isn't possible for all businesses or business models." And I agree with that.

I was able to release the first product based purely on my own skills. I also managed to launch it via my own blog, where I'd built up quite an audience (many of whom would be the target audience for my first product), which meant I had no marketing costs.

This left a little bit of hosting costs and the opportunity cost of my own time & energy. The latter theoretically being "free" or at least it didn't require a cash outflow.

The result was that once I had enough revenues to pay for hosting, the residue had two destinations: 1) re-investment into the business; or 2) my pockets.

Sooner is better

Not every new startup will be able to switch revenue on from day one, but there's one reason you should aim to do so sooner, rather than later: revenue generates momentum.

Ask any startup founder what it is like to start a new business and they'll likely you that it's a tough, rollercoaster-like journey.

This phenomenon will always be present in startup-life, but I've found that having momentum is key in negotiating the highs & lows that you will inevitably face. Momentum means you get through the low times much quicker and you can leverage it to go even higher on your highs.

Momentum runs on validation (knowing that your startup is doing the right thing) and excitement (knowing that you are making progress towards your vision). Early revenues creates both of those.

Obvious answer: we had no money and probably didn't know enough or think far enough to consider outside funding (not that I think we would've gotten it had we look for it).

But seeing this post - Ten Highly Successful Bootstrapped Startups -  over the weekend though, reminded  about the feature WooThemes got on 37Signals' blog last year and that made me all tingly inside again about our journey thus far.

See, I honestly think that we didn't have many options when we started WooThemes. We had no experience of running a business or fundraising, so we did the only thing we knew: work hard & make money.

From day one, we were profitable. We worked hard, charged for our work, made sure we were making money and we put that money in our own pockets. Seeing the immediate gratification (spare cash in our pockets), meant we worked harder, were more ambitious and built a profitable & sustainable business.

We never made an explicit choice to bootstrap WooThemes. We did make a choice to work hard, make money and grow our business organically. Today we can boast more than 43 000 paying customers and a team of 15. Not bad for 3-odd years' of work.

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.