Building another startup – lessons learned the second time around

Starting a business is exciting and exiting one successfully is just as exciting and as much of a learning curve as the rest of that journey. But if you’re a true entrepreneur, the itch to build, breathe life into a business and to ‘create’ never really goes away.

Having recently exited my first startup, following an acquisition from a private equity firm, I am now diving straight into my next venture, namely uRoutine. This time, however, I am armed with experience – and undoubtedly a few mistakes – that are significantly shaping my approach. Here are a few lessons learned that I am now applying to uRoutine.

While every business is unique, there are definitely some common lessons from the first round that I am applying to my second venture. If you're considering building again, or if you have just started for the first time, I hope that these insights may be helpful for you.

First thing’s first – is funding necessary?

So often I hear about startups for the first time as a result of a funding round. This seems to be the point at which a startup is validated or becomes ‘real’. This, of course, is ridiculous but true. The first time around, securing funding felt like a rite of passage. We chased investors, pitched endlessly, and celebrated when we finally closed an albeit modest seed funding round (the first of only two funding rounds). Looking back, I realise that while funding can accelerate growth, it also comes with a cost. We were lucky, we didn’t give too much away or take too much but if we had it would’ve potentially hampered our exit.

So, this time around, I am asking myself seriously whether I really need funding. I suspect we will take a seed investment round, partly because all of our first-time investors are keen to back my co-founder and me again, so the ‘hard work’ and potential distraction of going through a funding round won’t be there as much. Yet, I am certainly not rushing into it, and should we go through a funding round then we won’t take a lot or dilute too much. I am hopeful that we will only go through one funding round.

This time, I am bootstrapping as long as possible. The leaner approach forces efficiency, discipline, and a laser focus on real revenue. As I’ve said, I am not ruling out investment at all, but the decision will be made based on clear, strategic needs rather than an assumed necessity. If a start-up can grow without giving away a chunk of equity, then why wouldn’t you?

Vanity metrics vs. meaningful growth

In my first venture, I will be the first to admit that there was a huge temptation to get distracted with metrics that don’t really help the business. These are often referred to as ‘vanity metrics’. So, with metrics like web traffic, social media engagement, and app downloads. They looked great in pitch decks, but did they translate into sustainable business success? Not necessarily.

This time, from the outset, I am clear that there are only two metrics I will really focus on. The first is going to be user engagement (more about that in a moment) and the second is revenue. A thousand website visitors mean nothing if none of them convert into paying customers or if they aren’t staying around long enough to tell their friends or networks about our platform. These are the indicators of a truly sustainable business, not the number of retweets a post gets.

So, why user engagement? Well, engaged users of a platform (whether free or paid) will do wonders to marketing spend. Engaged users who love an app or platform will tell their friends, their family and the wider world. This, in turn, will reduce marketing spend significantly. This may not necessarily translate to revenue and in our case it certainly won’t at the beginning. uRoutine will be entirely free for individuals and we will look at revenue through brand partnerships and business licencing. However, engaged users will bring greater opportunities for brand partnerships and business licencing, both of which, in turn, translate into the second metric I am focused on – revenue.

The importance of focus

Another crucial lesson I have learned is the value of focus. In my previous startup, we tried to do too much, too soon. We spread ourselves thin across multiple features and target markets, believing we needed to be everything to everyone. It was a mistake. We didn’t really know what we were – a social network, an HR tech platform, a mentoring business, a bit of everything. Eventually – two years later – we settled on a much clearer proposition. However, that lack of focus made marketing harder and, in turn, our path to revenue, longer than it needed to be.

Now, I focus on doing one thing exceptionally well, with a clear proposition. That means saying no to distractions, resisting the temptation to expand too quickly, and prioritising depth over breadth. A strong foundation leads to sustainable growth. This strong foundation is something I am working on in every aspect of business, from brand and messaging to target audiences, marketing campaigns and the day-to-day work.

Patience, or lack thereof

One thing I’ve noticed the second time around is my decreased patience. Having been through the process before, I frustratingly expect things to move faster – whether it’s revenue, product development, customer acquisition, or partnerships. The challenge is reminding myself that, despite my experience, building a successful startup still takes time. I found myself, just yesterday, questioning why we had zero revenue, before I remind myself that we didn’t have the product developed fully yet! I had to tell myself to calm down.

Patience is as important as urgency. While I push for rapid execution, I also need to ensure I’m not rushing decisions or forcing growth prematurely. Sustainable success is a marathon, not a sprint, and learning to balance my expectations with reality is a discipline I constantly remind myself of. In fact, I went through our old startup's pitch decks and took great comfort in reminding myself that it took more than 18 months to generate our first slug of revenue (and it was tiny).

So, here we go

Building a second startup is a different experience. It’s less about chasing hype and more about building a solid, sustainable business. I now approach entrepreneurship with a greater emphasis on financial independence, meaningful metrics, and an unwavering focus on revenue.

If you’re on the journey of building again, ask yourself: What did I learn last time? What will I do differently? With experience comes clarity, and with clarity comes a higher chance of success. Here’s to building smarter, not just building bigger.