Pitch competitions as a measure of success

In our early days of my startup, I would try to enter as many pitch competitions as was feasible, just to try and get our project in front of as many eyes as possible and get our names mentioned in the popular startup press.

I used to give everything in these competitions, and we were finalists in several, including the prestigious Australia Post Pitchfest even in 2017. These competitions were crucial in getting us to hone our messaging, and to highlight what we needed to focus on. We learned a lot during this process.

But we never won one.

In fact, here is the results summary we got from one local pitch competition we entered:

As you can see, we scored a woeful 60% overall. We failed in 3 of the judge’s criterion. One of the key judges was highly critical of my HR platform startup during the on site judging, and this email further sunk the boot in.

But I saved this email. Because it only served to spur me on and to prove them (him) wrong!

Today, we have achieved 7 figures in ARR, and most of the winners in the pitch events I entered are no longer around.

Persistence and belief in yourself matters…

Founders - Don't just build another job for yourself

I was having pre-Christmas lunch with Paul*, one of my best friends from middle school a couple of weeks back. However, as soon as he sat down at our table and I asked him how he was, he surprisingly announced that he would be closing his business at the end of the year.

I was taken aback to hear this news. Paul was in his mid fifties like me, and had been running a really successful tree lopping and landscaping business for many years now. I used to frequently see his trucks around town doing their important work, and things seemed to be going well.

Or were they?

Our group of middle school friends catch up every few years for a special activity, and I remember 5 years ago, when we were all kayaking up the beautiful, world famous Nitmiluk Gorge, we had in depth conversations about our respective businesses while camped under the stars at night. (Odd to think that nearly all of us in the group had the entrepreneurial mindset and were running our own businesses or startups).

During those conversations, Paul would always lament that he could never get proper time off to enjoy these activities we planned, as he felt he could not leave his staff to just carry on the work, and that he had to be there to manage them and ensure that they got the job done.

Now I know that the sort of work Paul did was important, and had a lot to do with safety and ensuring that dangerous trees were removed without damage to property or human life, but he also mentioned at the time that he had an out of work commercial pilot working for him as part of his crew.

Now, as a former commercial pilot myself, I knew that someone who had been through such training would likely have good judgement and sense of responsibility, and could appreciate danger and risk mitigation and would be able to carry out jobs like pruning or removing trees quite well, however Paul felt that even someone who had gone through such training would not be able to do things as well as he could, unsupervised.

I remember sitting there under the clear Southern night sky on the sandbank next to gorge 6, looking at him across the campfire and saying “Paul, you haven’t built yourself a business. You’ve just created a job for yourself”.

He seemed surprised at that, but all the others in our group readily agreed with my sentiments.

You see, when we started our businesses, we all had the dream of being ‘independent’, and ‘free’ and all the other things that business owners wanted when we break free from our dead end, monotonous ‘jobs’.

Now I know that things don’t always go to plan, and we have all struggled with the concept of working ON the business rather than working IN our business, but ultimately, the end goal is to be able to step away from our creation and let it carry on without our day to day micromanaging and input.

As I grow my current startup, I am conscious of stepping back more and more as our team grows, and in fact, I am regularly surprised by what the team achieves these days with very little, if any, input from me. For instance, our customer success team runs regular webinars with our customers and prospective customers without me having to lift a finger, and they work better that I could ever expect.

I remember the days when I used to have to organise every aspect of such events, from setting up a booking website, configuring our webinar software, creating the presentation scripts, sending our reminder emails and running the event, doing post-production on the video and follow ups to questions etc. But now, my co-founder and the team just do this, and all the processes are documented in our internal Wiki so we can reproduce things even if a different team should do it next time.

This is startup nirvana for me. It is all still hard work that takes skill, but everything is broken down into repeatable steps and improved over time.

This is what Paul didn’t have. It is not that he wasn’t able to replicate such a process in his business, as I believe that almost any business can do this. It was just that he seemingly didn’t want to.

I guess for Paul, micro managing every aspect of his business gave him some sense of control and the feeling that the business was still ‘his’. He couldn’t see how his mental model of how he thought a business should run was being constrained and restricted by his thinking.

So when he announced over that lunch that he was closing, I asked him if there was a trigger factor involved, and he said that he had been training is daughter’s long time boyfriend as the person to take over the business when he (Paul) eventually retired, but his daughter had just broken up with the boyfriend, who was thinking of leaving town over Christmas as a result.

Thus, the potential heir that was being groomed as the successor was essentially out of the picture, and that left Paul with a business that could not run without him, and was unsellable. So the only recourse was to get rid of various assets and simply close the doors. Paul himself didn’t want to keep running the business because he was in the same later stage of life as I was, and the years of working under the gruelling tropical sun had taken its toll on his health.

I wish Paul all the very best in his retirement, and I am sure that he will do well, because as I mentioned, his business actually did quite well when he ran it, and he has a good nest egg put away. It was just his method of running things that I think was problematic. Paul could have had more freedom to travel and enjoy life while building and running his business, if only he had uncaged the belief that his business could not function without him there.

Whenever you hear someone complain about their job, it is usually because they feel locked into a set framework of working hours, or doing unpaid overtime, or expected to show up during holidays and be restricted in the amount of time that they can take off. These are usually the same set of conditions that most people who start a business say they will overcome by being their own boss - but sadly, like Paul, a lot of people will simply build the same restrictions around themselves in quick fashion.

In short - NEVER forget why you started your business or startup. Embrace the opportunity to dictate your own freedoms, and always make it a priority no matter what. Don’t ever build just another job for yourself that you will grow to resent over time.

* - Not his real name

Reflections on 2020

I feel kind of conflicted writing this, because 2020 was a horror of a year for most people around the world. Instead, for me, and my family, it was somewhat of a start of new beginnings and some huge wins.

I feel that I have finally stepped out of a decade long black tunnel, and I can finally see the light ahead. You see, back in 2009, I lost my dad, and my wife lost her mum. For us, each losing the parent that we were closest to really took the wind out of our sails, and we both felt that we had lost purpose and a solid goal in life.

I lost interest in my old consulting business, and ended up selling it back in 2015 so that I could focus on launching a brand new startup that meant I could write software that I wanted to write. My wife felt ‘blocked’ in her art, and ended up taking on multiple part time jobs to ensure a steady income for the family while I rebuilt my career (what a crazy thing to do when you turn 50, huh?).

It basically meant a decade of ‘grind’ and living on our savings and on the good will and charity of others. I am forever grateful to family members and close friends who supported us unquestioningly during those difficult days.

But I will be honest and say that because it went on so long, there were days where I despaired that we would never see the light at the end of the tunnel, and that I was just throwing energy into something that wouldn’t last or pan out the way I expected.

People came and went into our lives during that time. Some left us in a better position, but some also left us in a far worse position. After a former co-founder lost interest in my startup and abruptly left in 2018, I ended up in hospital with a stress related heart condition, and I feared that this would mean I could not bounce back again.

But being in these depths was also what forged my inner strength, and bounce back I did. I found a new co-founder and together we built the business up to a far higher level than I ever thought possible. 2020 was the first full calendar year we worked together, and we managed to get to well over a thousand paying customers and we currently manage tens of thousands of employees on our HR SaaS platform.

In some ways, the COVID scare that shut down most of the world was a boon for us, as more people wanted an HR system to manage their suddenly remote or ‘work from home’ teams. For the first time in a long while, I felt that were in the right place at the right time. Well, more accurately, the right place at the wrong time.

I don’t like the idea that we are benefiting from something that is causing so much misery, but I re-frame that as being that we are providing a valuable service to people that want to survive the tough times we are in. In fact, rather than capitalising on this by raising our prices as many mentors have suggested, we instead slashed our prices by half to make it easier for struggling businesses to jump aboard.

My wife managed to go back to just the one part time job that she loves, and she has more time for her art and other creative passions. Our oldest son, who had moved down to Melbourne to pursue his music career also moved back home while the entertainment industry rebuilds itself, so it has been good to have the family back together again.

This week was a milestone, as it marked the first full year of me earning a steady salary from my startup. It was so good not to have to watch our pile of savings diminishing away, and to be able to pay bills using the income earned from something that just started out as an idea in my head all those years ago.

Life is good. 2020 was good, and 2021 will be better.

Playing Beth Harmon...

Like most people, I was captivated by the NetFlix series “The Queen’s Gambit” recently. I have fond memories of playing my dad as a kid, but I was never really a good player. Which is strange, because I have always heard that programmers usually make good chess players. But I was the exception to this particular rule (or maybe I am a bad programmer too? 🤔).

But a couple of years ago, I made the decision to try and improve my chess playing skill. To become more strategic and long term in my thinking. I subscribed to a paid plan on Chess.com and started watching several YouTube channels regularly to learn what the grand masters do.

Happily last week, I discovered that Chess.com has introduced the ‘Beth Harmon Bot’ to their list of computer players, so I can now play against (the totally fictitious character, by the way) Beth at the various stages of her storyline, from a young girl starting to learn the game with the janitor at her orphanage, to the 22 year old Grand Master slayer.

I like that the bot has the unique playing style that Beth demonstrates in the show. Playing very quietly at the start, then launching a devastating attack during the middle game. Take for instance, the Queen’s Gambit opening that the show is named after. Most of the other bots I play on Chess.com will usually accept the gambit, however the Beth Bot always exercises caution that early on and declines it in order to position her troops for the overwhelming attack to come.

I love the fact that some of that personality is built into the Bot. I can almost imagine I am looking into Beth’s doe like, yet penetrating eyes across the board. Every unexpected move make me feel a nervous twinge, exactly as I would when playing another human player.

So far, I am managing to beat 9 year old Beth regularly, but 10 year old Beth has me struggling sometimes (I have yet to beat her playing black), and 15 year old Beth simply hands me my ass with alarming regularity (by that I mean: Every. Single. Time).

Here is a game analysis against 9 year old Beth (click on the image to go to the full analysis). I was particularly proud of this game because while it wasn’t elegant, I did manage to restrict her usual broad development and entrap her King by sheer force of will.

I will try and do another update in a few months to see how my game has improved!