Lessons from being in a startup and why we always say we’d do it again!

After just over three years of being at the helm of innovation, I left my role as Chief Operations Officer at Picup at the end of February 2018.

A fancy job description, a fancy title, but in reality, though, titles are simply a mere representation of how you want to be interpreted by others; particularly in a startup. But that’s only one of many lessons you learn when you’re pioneering and innovating — nobody can prepare you for the magnitude of the task in front of you and it’s quite likely no-one has ever done it the way you envision. After all, that’s what makes it fairly exciting.

A few days after accepting my time at Picup had come to an end, I made a commitment to myself (and my sanity) — a promise I would never revert to life in a startup. But just a few weeks later, I was approached to take on a role within one of the most innovative startups around; and how could I turn it down!

In my time at Picup, I learned an absolute fortune. I’ll always be grateful to the Founders who gave me the opportunity to deliver the goods and I will always remember the lessons I’ve learned; which is why I thought I would share them. Not just because I enjoy writing about my experiences, but also because I believe that many current CEOs, Startup Managers, Chief Experience Officers — and others — can either relate; or reflect.


I had to learn that no startup should ever open its doors without it’s vision printed and laminated on the wall. You’re going to scale pretty quickly and when you do, you want those who work with you to know exactly what it is they’re working on — and more importantly, why!

Many senior managers I’ve experienced seem to want to develop these visions over a number of strategic sessions with coffee and pretentious biscuits or weekend conferences, but I have to wonder: if you can’t take a pen and paper — jot down your vision — then what are you doing?

Your vision is the single most important aspect of your business. Without it, you have no reason to stick to your roadmap or achieve your goals. With it, everyone on your team knows exactly what they’re putting in and why.


What is so interesting to see, if you put 10 startup CEOs in a room, there will be the number of them unable to list their employees, their titles and job descriptions.

It’s like a long running joke in the startup world that one must be a ‘Jack of all Trades’ but in reality; that’s just a sign directly toward the lack of direction.

I remember when we first employed our General Manager (then a Regional Operations Manager) at Picup; I kind of needed an assistant. Someone to take the workload off my shoulders and help me out. We created a fancy title and brought someone on board; within no time, he’d gone on to expand his role. What it became, I actually had no idea — and reflecting now I think one of my major flaws was not sitting down — then and there — and putting together a precise job function document of sorts to formalise the role and identify his roles and responsibilities.

This can (and should) be applied for almost everyone in your business. Before you want to bring someone in, write up a list titled What Will This Person Do. Once you’re done with the list, ask yourself if anyone else — currently employed — should be doing those functions. If not, it’s probably a good thing to hire that new someone, just ensure you save your document and print it out so they know their role!


I once heard from a client they had decided to go for cheap wooden benches in their fancy boardroom — not just because they wanted to be innovative and different, but because meetings (they believed) were a waste of time and the more comfortable you are in your boardroom, the longer you stay chatting about the weekend past.

But this comfort is a very different sort of comfort although in some way or form it’s comparable. There were plenty of moments during my time at Picup where I’d be asked, by friends, what it was like being me in the office. Having to describe your job to anyone is always a tedious affair. Looking back, I think my simplest response should have just been one word: Comfortable.

If we’re too hard on our staff, they probably won’t stick around. And if we’re too friendly and sibling-like, things will get far too comfortable. Remember, your employees are your workforce. They ensure the cogs turn, the machines are oiled and the plug is switched on. They’re not your family who’ll still be around if your startup fails. And they’re not your friends who’ll sip a beer with you, lamenting the boss, when their salaries aren’t paid. That’s the reality.

Of course, I don’t mean your employees shouldn’t be treated like family, close friends or confidants, but you need to draw the line and ensure you’ve got a very clear work-friendship boundary — because at some point, comfortable is not so comfortable anymore.

Unless you’re going into business with your bestie, your employees are not your mates. They’re the most vital tools to your business’ success.


One of the most exciting reality shows I actually enjoy and tend to watch, Undercover Boss, really sums up the need for a fairly senior manager to know their staff.

The show, although a little ridiculous at times, opens your mind to the fact your staff actually have some insight from which you may benefit. If you engage your staff, weekly or monthly, you’ll start to see a very different side of your business — one you wouldn’t have uncovered from the draw-side of your office desk.

In a startup, we often forget to engage our staff. Are you happy? Do you actually love this company? Do you even know what we really do? Are you even aware we work weekends? You mean you can’t tell me what our vision is?

Nothing is more important than knowing your staff, what they think and what they want to become. They too have ambitions. Probably, not ambitions that include your company, but they have a somewhat clear picture of the life they’d like to lead in the near future. Your job, apart from returning investment for your shareholders, is to understand the frustrations and needs of your staff.


Shortly after leaving Picup, I was invited to meet with a CEO who seemed adamant in having me on the team — I was fairly confident I didn’t want to be back in the world of startups, at the time, but hearing how he’d gone for gold and then whittled down to become more focused seemed to be some type of light-bulb moment for me. I never took this job, though.

You simply have to open google and type in startups who failed only the see those who hog the first few pages are the ones who’d received thousands (or millions) in funding and went so big they simply couldn’t cope with the scale.

Now, I think many startups go through what I term as the pivot phase which essentially means at some point the company considered (or did) change direction — either entirely or just a tad.

In my limited experience, I’ve decided you’re entitled to have your moment in the wind but when that same wind is knocked out your sail, don’t be afraid to reassess your business, your model or your strategy — remain focused on your vision and if it means scaling down to make your objectives more achievable, don’t be afraid!

Don’t be afraid to make mistakes and change direction. Just make sure you don’t repeat that same mistake again.


It seems like an effective tool these days to offer staff a share incentive instead of a higher salary. Let’s face it, startups really don’t have all that much in the bank and spending it on high earners leaves any financial manager with a sick feeling in their stomach.

But if you’ve followed the first step in my advice, by defining roles, you’re already four steps and a hop ahead. Employees always think they’re worth more than they are paid — sometimes, they are. I do believe that not one person in your company is beyond being replaced by someone with a lower salary; however the output may differ.

Far too often we see startups employ young, inexperience, at a senior level. In fact, I suppose I was thrown into the deep end at Picup shortly after joining; so I too may arguably be termed as young and inexperienced. But when it comes to scale, it doens’t help to keep bringing in the untested. At this particular point in your business life-cycle, it’s time to turn to the professionals.

Let a Finance man do you math; let an Operations man take your product or service to market; and let a creative expert be the pinnacle point of your message to your target audience.

Most importantly, your staff need (and want) to know they’re important.


A title may seem like nothing to you. It’s really, nothing, in the grand scheme of things. It’s rather ironic though, isn’t it? The one who takes on the CEO role is quite often the first one through the door of the e-mail signature office. Quite happily the one on the phone to the property broker, chatting about rent for the new office to accommodate scale, referring to oneself as the CEO.

Well, it’s important to your staff. When I started applying for jobs, I began enquiring when I got a positive response as to why they thought I was right. So often, you have to explain why YOU are the right one for the job, but here I was turning the cards: “So, what makes me the right person for this role?”.

Of the seven times I asked this question, the response was almost like they’d read the same blog the day before: “Well, because you were the COO of a startup and you know how to run a business”.

Well, little do they know, for all they know, I was just a skivvy mopping the floor and counting the beans. My point here though is simple — when your staff move on, their titles will mean their next opportunity is in reach — don’t limit them but at the same time, take interest in the question when they ask: “Hey, what would my title be?” and ensure you’ve written out their job description with key performance indicators.

This way, everyone knows what’s expected.

Traveller, Blogger, Author, Sports Fanatic. Chairman of Rygersdal Football Club, Founder of Incoming SA and The Kimberly Rose Cancer Foundation.