What I learned from a StartUp weekend

I had the privilege this past weekend of participating in, and pitching at a startup weekend in Melbourne, called Launch 48. It was organised and co-ordinated by a wise mentor & confidant of mine, Grant Downie. As well as participating in, and contributing to the startup community through leading the Melbourne chapter of Startup Leadership Program (SLP), Grant is also an inspiring startup consultant.

In participating, I had a number of objectives that I wanted to achieve, of which I hit every one. On reflection, I realised that I gained something immensely more valuable - perspective. This insight is too important to leave locked away, so important in fact that it's worth stepping away from my normal blog format of "challenging ideas".

The weekend was well run, and well supported by sponsors, advisors and mentors, (many of whom I've had the opportunity to meet & discuss concepts and projects within the startup space over the last 2 years of my own involvement) which gave me every chance of achieving the objectives that I had set.

Having previously developed 8 past startups  (although still seeking my first big exit), this was not my first rodeo. However, 8 years as a solo entrepreneur and  'lone-wolf' consultant have instilled in me some practices & habits which had, in times past, lead me to question my ability to deliver on a startup business, a number of which became obvious during the weekend. As an example, wide base of knowledge together with a gregarious personality can often be off-putting, especially to others with a much deeper understanding of immediate issues.
Initially my focus was on crafting & presenting a compelling pitch for an idea (later to become @TerraLingo) which I had been analysing for a number of weeks. I had seen an opportunity and realised that Launch48 represented a perfect opportunity to test that idea for validity -
It's worth noting my objectives, which were very clear -

• Deliver a compelling pitch for an interesting idea, around which to form a team,
• Develop a validated business model with clear objectives, within a collaborative team environment,
• Build a proof-of-concept (POC) around the current idea, from which a minimum viable product (MVP) could be formed,
• Test my abilities in leading and guiding a team towards those objectives,
• Identify 5-6 potential team members for a later much larger idea which I have in mind (& for which  I have a 6 other team members keen to go).

It also turns out that the actual idea that you might take to one of these weekend is actually less relevant than what you learn (both about the startup process & about yourself) and who you learn from.

The weekend started well; there was the usual meet & greet over pizza & ale, allowing everyone to change gears from their regular activities, mix & mingle with other particpiants, and at least initially for me,' feeling out' some of the other pitchers.

The format was simple enough, the nominating pitchers had 60 seconds to pitch their idea   (of which there were 11) to fellow entrepreneurs , after which and audience poll (of around 40) was taken as to how many people might be interested in working on that idea. The top 6 were then given an additional 30 seconds and after a second round, the top 4 lead ideas were selected around which the leaders had to for teams. My idea attracted the highest number of participants, so we had a deep pool of experience from which to draw & build upon.

Of our group, at least 4 guys had pitched their own idea, which demonstrated something early to me - that at least 4 of these guys were visionary leaders, or aspired to be. As it turned out over the weekend, all of guys showed great leadership qualities in such a 'pressure-cooker' environment. The team was slightly siloed, with myself, Sebastian, Christoph and Berlin handling research, marketing, customer development, UX/UI and the final presentation, whilst Nick, Stef & Matt handled some difficult technical, app & web POC, and API requirements.
I tried not to make my observations sound like recommendations, but when you spend a weekend with a group of such obviously motivated, skilled and clever guys, its hard not to.

• I had also made a list of the qualities & characteristics of the types & roles of 6 people that I last looking to attract as 'department leads' for my next project. The phrase 'be careful what you wish for' comes to mind, because what I listed is exactly who I found. (BTW, the 6th guy on my 'list' was a very interesting 'product' guy who was on another team, whom I met following the final pitch)

The first of my followers is Stef (the only one of the group that I had known prior to the weekend). Steph & I have known each for about 5 years, played poker together, shared stories-  tall tales and true - over the occasional sherbet, and share (generally) very similar life stories. I share an affinity with him in our individual capacities to endure & overcome personal difficulties -- and he's a really nice guy.  Stef is very good technically, with a great skill set , though like me, he suffers from the occasional crisis of confidence which has the capacity to hold oneself back. Friday night was one such evening, and were it not for my absolute insistence, he probably would not've turned up.

Nick is a stand-out leader. We didn't talk too much about his background (or perhaps I wasn't initially paying enough attention), but it became immediately clear that his depth of understanding of the processes, and of the technical requirements of building and scaling a tech startup were deep. He was the obvious stand-out leader for the technical side of the project.

Nick challenged me immediately (which not many people do) on a range of assumptions or concepts that I tabled to the group, and in hindsight, I am really glad he did. During the course of the weekend, we disagreed about quite a many things (it was a almost the classic 'marketing v tech' battle that many of us have so often seen). To his credit, in every discussion, Nick did something very important (and extremely rare) -when we disagreed about a method or an objective, he "played the ball, not the man"; a quality that my dad demonstrated when I was growing up, and which I have since always admired  and respected in people.
Nick also did something else critically important;  he immediately took Stef under his wing and lead him through the development process. In our wrap up conversation, Nick talked about successfully using 'peer programming', and the benefits of that approach for both Stef & himself.  I also suspect that this contributed greatly to the ultimate success in creating a cohesive team.

What started perhaps as a challenging discourse, turned for me, into a deep respect for Nick's skills & abilities, and for him as a person. Stef also came away from the weekend with a deep respect for Nick, both as a man, & as a leader.

Matt, our tech genius),apart from being a very likable guy, demonstrated himself as highly capable and skilled, with a deep understanding from the beginning  of what it would take to get to 'success' - almost a classical 'tech guy' archetype (there is no negative sentiment in that statement). He took a very methodical approach to identifying & addressing the challenges of the task, and delivered on every milestone exceptionally (at least from my perspective). He demonstrated early (unlike many tech guy that I have met) that he could be relied upon to identify the core issues, and solve them inside the tight time parameters that were set for us - whilst still exceeding our expectations. (Without knowing the answer, I imagine that Nick's leadership shone through in contributing to that). As Stef later told me, "this guy went way above & beyond !! He went home Saturday might and virtually built most of the iPhone app until two in the morning. Nick and I just put on the finishing touches." That is something special, & I couldn't have said it better.

Sebastian is something out the box; from the get go, his attitude screamed "let's get this done - well". His capacity to see where the destination was, and pick-up on the milestones, without needing guidance or managing, literally  blew me away .In many ways, he was the marketing 'mirror' of Matt. Because he knew his craft, he not only took the lead on some of the critical tasks, but was able to anticipate what was the obvious next step before we got there. His attention to detail as was impressive as his repertoire of skills.

Christoph, who is a wiz at design, had pitched an idea of his own, which didn't get up. However, he immediately saw the similarities of my idea with his own, and joined us. His willing to challenge (causing me to stretch) was impressive, though his ability to connect customer needs to design requirements wasn't too shabby either. From a 5 minute conversation with me, he put together a professional design that just 'worked'. I noticed how well he interacted with the other team members to bridge any skills gaps (including my own), and has a solid knowledge of the needs of the marketing strategy plays in the startup process.

Berlin is a great young guy (I say young, because he is compared to me), with good skills in marketing, & in being an engaging networker, which I had noticed earlier on Friday. He contributed early and often to the ideation & solution design process, and really shone in researching, and when the deadlines started looming.  I wonder whether, in hindsight, we might have made better use of them earlier by pairing him with Christoph for some of the customer engagement tasks.  Whilst a little 'green', he shows obvious indications of being a successful entrepreneur.  I believe Berlin will benefit from identifying a solid mentor to guide him on the path to his success, or slotting into an 'apprentice entrepreneur' role, but he might equally just need to find  the right co-founder to balance out his skill set.  

ME
This is where it gets a little hard; how does one give constructive feedback on one-self?  Perhaps by making an external observation. One of the obvious things about the weekend, apart from the long hours, and the commitment by everone to the task at hand (which by the way was exemplary), was the roller coaster of emotions that I experienced at the various stages. This went from the nervousness pre-pitch, to the elation of selection, through the challenging ideation process on Friday night & throughout the weekend, to the feeling of doom from the looming pitch deadline on the Sunday night.

So the concept of 'state control' is one that is clear and obvious to me now- to operate at your peak, you have to maintain control of your emotions  (or at least have a plan  for addressing),  and expect the both major highs and lows, and plan for how to deal with them accordingly when they inevitably arrive.>

The most challenging space for me occurred on the Saturday early afternoon after the series of 6 or seven pairs of mentors and advisor discussions, during which our idea expanded my two orders of magnitude from my original vision.  My head was swimming with the possibilities that had been put before us. To put it the words of Sean Parker "What's cooler than a million dollars? A billion dollars". Suddenly, we had gone from having a good idea worth potentially a good couple of million or two (purely by my own estimation), to perhaps 100 times that. So I was now pushing to the limits of enthusiasm for the tasks at hand.


But this process had put too many well-intentioned, and absolutely valid ideas on the tale from experienced & highly credible mentors. As a product team (& unbeknown to the tech team), after those meetings, we now realised that we actually didn’t know what the product was. No product meant no customers, meant no revenue, meant no Business proposition. It was later in the afternoon, that my self-belief, and my vision of a viable valuable outcome,  crashed to the floor. Whilst (I think) I did a good job of masking my concerns, my emotions showed through in the discussions around rebranding later on Saturday.

It wasn't until early Sunday morning after a  couple of hours of solitude (again, an important observation), that I gained some clarity and perspective about where we were  headed. The challenge for any leader is to do just that - to lead. To get out in front of the pack, raise his sword and charge forward  toward the enemy with a battle cry like "Glory or Death". But before you draw that sword, you better have spent some time alone or quietly with your generals in thinking through your battle plans, lest your battle be over & lost, before it is even started. 

I was also reminded of the need to make sure you frame your message to the needs of your 'audience'. I'm not just talking here about a large audience, but also in a  1-on-1 conversation. One of those 'dirty little habits' that we can fall into, is to continue to deliver the same message (or delivering a different message in the same way), perhaps because its familiar, and forget to think about what it is that the participants are looking for. Always starting from a position of honesty is good, and the highest ideal of 'serving' is worth keeping in mind. Because in seeking to serve, we take our eyes off what it is that we want, and focus on the needs of the other, which is great path to get away from 'delivering a message', and should take you closer to 'understanding'.

One of the other important lessons that I took away from the weekend, is that in a team approach, perhaps that most urgent, & important task for any leader , is to identify  the natural skills & strengths of each team member early, and harness those early in the pursuit of the larger vision. I'm not talking here about task allocation, although that is part of it, but more so about recognising early that which  each person brings to the table, and allowing that to shine through. In our scenario, in places, that happened naturally, and in some spaces, we left a lot on the table. 

I'd have no hesitation in working with any or all of these guys again. In one weekend, we went from one man's idea to forging together as a team and building  something 'very cool'. Our the next 2 or 3 weeks, we'll find out if TerraLingo has 'legs', and we'll leave no stone unturned in that process. Or it might be the next one where we come together. Either way, I give my thanks individually to each guy, and to them the team as a whole for the gifts I got from the process.  It's hard not to feel like you 'got' way more than you 'gave', which means you get to keep giving . 

But I also learned something critical; perhaps the most important thing; how special and rare 'startup guys' are. We commit, contribute and care about a goal (ours or some-one else's), journey through the dark across a valley of death, which we know from the tales of others before us, is filled with peril s & obstacles, and has very little chance of success, yet with little  more tools than our own skills, faith in a team (whom we barely know), and the meerest  hope of reward and recognition.

And we not only do this willingly, we also do it repeatedly.
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I don't know what you think, but for me, I reckon that's pretty special and very cool.