I'm limited. My skills are finite. Regardless of how many new things I learn, my skills set is not limitless. This obviously means that there is only a limited number of things in my life that I will be truly good at. Some skills I may be able to enhance with practice / experience and a few others I'll be able to hold my own (whilst never being great at those). Fact is, I can't do everything.

This honest self-evaluation has been especially true for in my business / work life. A couple of years ago when I co-founded WooThemes, I was a DIY-type designer / developer / jack-of-all-trades. As the business has grown though, my role has evolved significantly and I'm now the "business guy" at WooThemes (main reason being that this is something I'm much more passionate about than pushing pixels or writing lines of code).

In this role, some of my main responsibilities are marketing & business development (whatever exactly that is). Considering I did my graduate studies in accounting & only did a one year post-graduate in business strategy, neither of these two are things that I'm necessarily great at, yet I'm tasked to take care of those in a very successful business. I don't think I'm bad at those either and in fact I think I've got a bit of natural talent too. My 3+ years of experience has obviously also helped. I'm still not great though. 

So with this in mind, I've been doing a couple of things to counteract the inevitable fact that I'm simply not great at everything. Natural talent goes a long way, whilst a "student-like" mentality coupled with experience will increase the reach of that talent. None of those are sustainable though and I've identified a couple of ways in which I can avoid stagnating personally, as well as within our business:

• I believe that every single person we've hired at WooThemes, has been better than myself at something. As mentioned earlier, I was much more hands-on initially in terms of design & development, but these days that is not needed since we have incredibly talented people taking on that responsibility. I also believe that it is absolutely crucial that - as an employer - I need to trust these guys' opinion and back their decisions with conviction, because they are much more talented, skilled & experienced in those areas. If we didn't hire guys that were better than the co-founders in some way, we'd stagnate pretty quickly, since the company could only grow at the speed at which we could grow as individuals. Hiring a team that is better than you though, drives the momentum of that growth / innovation forward exponentially.
• Being based all the down in Cape Town, South Africa (read: far removed from any major tech hub) it is a challenge to make friends and have mentors in our industry. Through the years though, I've spent a lot of time building relationships online (WooThemes' success has obviously helped with this) and I have many great friends that have founded or are working at much bigger companies than ours. Whilst they don't necessarily act as an "official" advisor / mentor, they are always available to me if I have any questions or I just want to bounce an idea off them. This kinda feedback from an experienced individual is absolutely invaluable in terms of exposing myself to other ways of thinking and implementing generic strategies.
• One of the things I've been intrigued about in recent months is the notion of working with specialists to consult on specific things within our business. A couple of months ago, we worked with CoSupport to improve the way we were doing customer support. Sarah Hatter (who heads up the team at CoSupport) was previously responsible for the setup & running of 37Signals' customer service for 6-odd years. So you can just imagine the type of invaluable feedback that she & her team was able to pass onto us. The whole experience was so enriching, I'm no actively pursuing a collaborations with similarly awesome individuals to consult on other areas of our business.

I don't generally do things out of fear, because I think that fear is a relatively stupid foundation on which I can base a decision. I do however have a fear of stagnating. I want to learn more every day and every morning I want to wake up, I want to try be better than the day before. This same attitude applies to what I do in business and right now this energy is directly focused on growing WooThemes even further.

There is just however no way that I can do that without working with other people that are better than I am. Recognizing & embracing this has probably been the best decision I've ever made in business.

Everyone is working to hard. I include myself in that statement: I work too hard most of the time. Heck, in my average week I make compromises with regards to my health, my home life, my marriage and all of my friendships. All for the sake of working harder.

But what's the rush? What's chasing me / pushing me to work this damn hard?

While reading "Why Working So Hard Might Be Doing Your Startup More Harm Than Good" last night, I was reminded of a conversation I had with a friend during a visit to San Francisco last year. It went something like this:

• Friend: So do you guys also pull crazy all-nighters and massive hack sessions, with minimal to no sleep, over at WooThemes?
• Me: Nope. Why would we do that?
• Friend: That's the way startups work. You hustle all the time to get your stuff out quicker.
• Me: Nah, that doesn't really make sense to us. We prefer doing things in our own way, at our own pace. That way our jobs generate the most happiness.
• Friend: *confused look*

I know that GaryVee has made the term "hustle" massively popular and every startup founder / business owner / entrepreneur is supposed to hustle their faces off. I understand that: I've worked incredibly hard along with my cofounders and the rest of the WooTeam to get to where we are today. Nothing happens without hard work & a fierce commitment to chasing one's dreams & goals.

The thing is I'm not an entrepreneur and neither did I cofound a company to hustle my face off all the time. Entrepreneurship & owning my own business is about so much more than just hustling all the time:

• Loving my job;
• Financial security & freedom; and importantly
• Flexibility to allow me to spend more time with family / friends.

I'm not saying that it's impossible to be happy when you're simply hustling all the time. For some entrepreneurs that's fine and if you are happy with all those compromises that it eventually leads to, then who am I to fault you? I do however believe that the constant hustle that is being associated with startups by default these days, has created a distorted view of what it means to start your own business, being your own business and having some fun.

Your startup really shouldn't kill you. If anything it should be an enabler for you to be happier, healthier and work less (at minimum do the work your most passionate about).

I've not stopped working very hard, because I'm ambitious and I love my job. I am however trying to get a much better balance between my work & personal life. Ultimately this freedom is one of the main reasons I ever wanted to be an entrepreneur. Not to hustle my face off.

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.

Life changes so quickly...

I can finally (publicly) share that Jeanne & I are 9 weeks pregnant and expecting our baby later this year. We've known for a couple of weeks, but waited for our first doctor's appointment before sharing the news with the world.

Heck, to say that the last couple of weeks have been a whirlwind would be a complete understatement (as I still have some professional / business news to share as well). Along with the absolute joy & excitement of finding out that we'll soon be parents, it is just so obvious during times like these that one's life can really change in the wink of an eye. I do however expect that these changes will be the most rewarding experience I've been part of during my life thus far.

I don't intend for this to become a "daddy blog" during the next couple of months, but "parent" is soon another title that I'd add to my resume. So expect the odd update on how that changes my life as a "rockstar", business owner and entrepreneur. :)

I have often wondered what defines me as an entrepreneur: Is it the fact that I've managed to co-found a genuinely successful and profitable company (WooThemes)? Or the fact that I've tried my hand at quite a few other projects and ideas along the way?

Can I be considered successful if my failures outrank my successes? At least in terms of the amount of failures I've had, versus my own - albeit very significant - success?

I've always been very critical of myself and in that vein I'm constantly tempted (yes, in that very emo way) to feel like I'm more of a one hit wonder, than a serial entrepreneur (something which I aspire to be... I think...). See, I'd love to believe that WooThemes was no fluke and that I could use the skills, knowledge, experience I've acquired via WooThemes and apply this to a new business venture in future.**

Until now that hasn't really been the case, with most of the side projects I've been involved with either stagnating or not really growing in the desired direction.

I've been toying with the idea of becoming an angel investor and at least repurposing parts of the wealth (experience, knowledge, connections, as well as financial capital) I've accumulated to diversify my business interests. I'm keen on this only partly for financial returns, with the determining consideration being that I love being involved with awesome projects. This however doesn't solve my feeling that I might be a one hit wonder... But then again, how many entrepreneurs have really gone on to found multiple companies? (I'm not talking about those that have simply become financial backers of a great idea; I'm talking about getting involved in the trenches of a startup all over again.)

Heck, shouldn't I even be concerning myself with these questions and self-doubt?

** I don't intend on leaving WooThemes for the foreseeable future.