Walking in the shadow every day


Long time since my last blog post. The last few weeks have been fucking hectic, so thought I’d write up something as it’s gnawing at me. I’m going to commit to more regular blogging once one or two more operational things are in place, so until then it’s as and when I can ;-) If anything, from now on, the stuff I write here will be for me and me alone. If anyone digs it, then awesome. If not, then I’ve got something to reflect back on.

So the last while has been an immense, epic, fucking monster entrepreneur roller-coaster. I’m cursing not because I’m an ineloquent person, but because I’m trying to get a point across in a blunt way.

On one day, we hit milestones and numbers that make my eyes water. I mean, I’m sweating blood for 3 years, delaying gratification for pretty much anything one can delay gratification for, and then in 4 months we start to grow in a way that I was dreaming about 3 years ago. We’re hitting metrics that show we’re growing, and fast.

Then on the flip side, we start hitting operational growth issues that are slowing us down, and creating a lot of pain. Everything is fast, everything is a firefight, everything is aimed at keeping the growth going so that we get to profitability faster. But it’s cool. Those are the good problems, those are the ones I’ll wake up at 4am to conquer any day of the week. Those are the problems I want.

It’s the fuckoff big other stuff that crops up at exactly the same time, which makes you wonder whether you can cope with it all. It’s the people you trust that let you down when it really matters, that makes you wonder whether you’re ever going to trust people from the get go again. It’s the mistakes you make when you’re so tired from firefighting all day long, that you really wouldn’t make usually (I left my wallet and phone on a train after no sleep; this is after identity theft and credit card fraud), which just complicate things further.

And so from one hour to the next on the same day, literally, you’re dealing with epic shit that doesn’t sit on normal people scales. Almost 99% of people I speak to just don’t get it. They can’t relate, so I don’t say anything anymore. I just say I’m in IT and Wedo ecommerce.

So what’s happened is that my tolerance / ability to deal with things has changed massively. This is a good thing, and this is part of why I’m writing this blog post. You learn shit about yourself when you think you really have nothing more to give. It’s also taught me that it’s something I have to become comfortable with to keep growing, and to become the person I know I am inside. I’m going to change and push the growth even more so I deal with stuff better.

But, it feels like almost every day my universe is at threat in a fundamental way, like I’m walking through the Valley of the Shadow of Death every day, and it’s fucking hard.

And that’s all. My internalisation.
There’s no getting away from it ;-)

In praise of routine


For the first time since October 2008, I’ve been in one place for more than 6 months. Long enough to get into a routine and start to feel like I’m living a normal’ish life. Long enough to feel like I can start building something more than airmiles.

The simple benefits to this is that I’ve now got a stable personal cashflow, and consistent expenses which I can budget against and plan for. I know I’m playing hockey each week, know that I can go to gym and do exercise regularly, I know I’m going to see key people in my life often enough to engage with them more than superficially,

As an aside, this happily coincides with being in London for 10 years. Thinking back, I’ve been in London for longer than any other city, since I was 13, so think that affords me the privilege of saying I’m a Londoner. More importantly, I no longer feel transient here. I’ve got a plan, I’m on a mission, and I’m comfortable with that.

I thought I’d never say this, but I’m really enjoying having a routine, and through living the routine for long enough, I’m starting to see the benefits of optimising that routine, and getting into daily habits which make life better, faster, easier, more fulfilling.

More and more, I’m drawn to the conclusion that despite what our modern society preaches about the always connected lifestyle we lead, there are some simple fundamentals which are absolutely essential to making personal progress, and good daily habits are one of them.

What are your daily habits?

Overextending leads to self discovery


Seth wrote a really good blog post about Underextending, which got me thinking.

Last year I took some very big financial, personal, emotional and reputational risks, in two countries. I completely overextended myself. It hurt like hell. There were times when I thought I’d never get through it all. There were many times when I thought I was going to lose everything. And I mean everything. I got to the end of last year, and I was broken from overextending myself. I won’t go into the tactical stuff and what I did to get through it just yet, mainly ‘cos it’s still too close.

What I think is important in the context of Seth’s blog post, is that the overextending from last year has led to so many great things that are happening now, and it’s just the beginning.

I didn’t see or predict it last year, I just knew they had to be done. If I had have known then what I’ve seen now, I would definitely have spent less time worrying.

Too often we back away from apparent pain, in fear of the risks involved, not looking at the benefits that may come afterwards. If anything, the last 18 months has taught me that well timed, well executed overextension is actually what creates the lifechanging progress we all crave.

Shameless plug – please vote for my panels at SxSW Interactive 2010 ;-)


If you’ve got a few mins, would appreciate your vote for my panel submission for SxSW next year ;-)

Starting and Selling Startups – Lessons From the Coalface

This session looks at finding that ‘right idea’ and following it through the phases of building a company, building the product and selling it on. It covers people, technology, finance, working with investors, scaling-up, general do’s and don’ts, what to look out for in an acquisition partner and more…
Questions Answered:
1. Why values and working with integrity is so important
2. Why talk is cheap and execution is everything
3. Why hiring right is so important and what you should do to motivate, grow and develop your team
4. Why you can’t succeed on your own
5. Why a frugal approach to technology, premises and other operational elements makes sense
6. How you distinguish between attitude , aptitude and talent; which you need and how you go about acquiring staff with the right mix of each
7. When equity is important, and when it’s not
8. How to tell serious investors from ‘chancers’ and how (in general) one should work with investors
9. The pros and cons of an acquisition – when to take it and when to run for the hills
10. How not to get sucked into the black-hole of scaling-up

Starting and Selling Startups - Lessons From the Coalface

Lessons From the Long Trenches: Bootstrapping 301

Bootstrapping can be a painful, problem-ridden process, laden with hundreds of potential mistakes the eager entrepreneur can make. From strategy, to finding funding and managing resources, this session shares hard-earned insights into what some of those obstacles are, what tools startups need and why it’s definitely worth it.
Questions Answered:
1. Why is bootstrapping one of the best ways to start a company?
2. Why are integrity and values so important?
3. How do I leverage what capital I have, even if it’s not much?
4. What kind of people should I hire?
5. What skills do I need in order to bootstrap successfully?
6. Why I should “Always Be Closing”?
7. Why starting up is just a state of mind, and not a state of being.
8. How do I leverage debt and credit smartly?
9. Why do I need to be good at networking?
10. Why do I need systems and processes?

Lessons From the Long Trenches: Bootstrapping 301

If you do, thanks millions.
If you’re gonna be there, please ping me / comment so we can make a plan to hook up then.
And, checkout the other interactive panels too!

Thoughts on #geekretreat ZA


I had no idea what to expect from the GeekRetreat (content will be updated there ov er the next few days so bookmark it) this year, but I did know that there were some smart people going, and I liked the themes being discussed. So I went in with an open and optimistic mind, and in truth with no backslapping, I was thoroughly blown away by the diversity, humility and good nature of the folks there.

Since SxSw 2006, I’ve maintained that the value of events is generally the conversation outside of the panels / talks, that are the most interesting…. so if you get good, new content, it’s a bonus. This weekend I had the pleasure of being in the bush and around campfires, listening to some smart people talking about interesting things, as well as getting to explore *stuff* outside of formal talks.

So I’m really happy I had the privilege to go, and more importantly came away with renewed energy for South Africa, respect and new friends.

Check out the twitter stream for live commentary.

What follows are brief thoughts that I took home or that stood out for me, in no particular order:

  1. “The best thing that South Africa exports, are South Africans themselves” Shapshak 2009
  2. Taking the risk to start something seems to be the largest hurdle people talked about.  Note that this is a psychological one, not a physical one.
  3. Vinny Lingham said some interesting things around funding and seed capital – mainly that there is money around, but little opportunity for early stage investors to cash out with local VC’s.  Vc’s in SA are also run by accountants, with an obvious connotation.
  4. Thus it seems that cultural baggage and an early stage funding vacuum, are primarily responsible for the relatively small startup / entrepreneurial culture in SA.  Poor bandwidth doesn’t help either.
  5. There seems to be a genuine willingness and motivation to develop and build for the lower end of the local market.  Problems around this are understanding real problems that need to be solved (rather than perceived problems which may not be problems at all), and figuring out how to make digital transactions possible.
  6. The idea of a co-working space in SA (JHB and CT) was well received.  This is something I’m taking up seriously both to bootstrap within, and jump start the local community.
  7. There are some seriously smart people in SA. I would love to see them doing stuff on the global stage.  I would also love to see them revolutionising the next evolution of the African web.
  8. People seemed to agree that niched communities are the way the web will evolve and organise itself, with Google as the entry funnel.  Nice to get affirmation of something I’ve been thinking in my head for a while now.
  9. A good example of the above is http://obami.com/, which looks pretty interesting, check it out.  Best to Barbs!
  10. Another web app / saas startup doing well is http://www.payspace.co.za/
  11. https://www.ravelry.com/ is another example of a super niched community doing well. Thanks @Pam
  12. Vinny is doing better with Yola than I thought (in numbers) ;-)  Good for him too, and great work dude ;-)
  13. Geeks in SA know how to party. Don’t challenge them to braai’ing and/or drinking.
  14. Geeks in SA seem to like Macs and iPhones.  There were one or two netbooks, and one or two Thinkpads and HP machines… Even the corporate people had Macs.
  15. Pretty much everyone at the event expressed an interest in going to SxSW next year.  Tally ho!
  16. Heather, Eve, and Justin were the glue that held it all together.  Kudos to them. And thanks! ;-)
  17. A big thanks to our hosts too, great venues.  Red Ivory backpackers, and the Elephant Sanctuary.

Other posts so far (will keep updating):

Photos (will keep updating):

Some startup tools (after the fact, but useful):

  1. Startup tools wiki
  2. 25 tools for startups (in comments of the above, but saves you the effort)

A quote from Desmond Tutu


Desmond Tutu spoke at my school once, and he was awesome. Always enjoyed his sense of humour and pragmatism towards the issues we face.

Came across this, this morning, and wanted to share:
“A person with ubuntu is open and available to others, affirming of others, does not feel threatened that others are able and good, for he or she has a proper self-assurance that comes from knowing that he or she belongs in a greater whole and is diminished when others are humiliated or diminished, when others are tortured or oppressed.”