Trials and Tribulations of Running a Startup

After a brief hiatus, I'm back to share insights & lessons learned from our startup journey at ESPROFILER so far.

Having worked at two startups previously, I'm familiar with the environment, especially from a sales perspective. I know how challenging it can be to persuade customers to even speak with you, let alone invest, when you're a new brand in a new market.

However, I can also say the highs of subsequently winning those customers are hard to beat, you have to work so much harder to convince a customer to partner with you.

I always remember a wonderful ex-colleague, Rich Balla, saying "I want to go to a startup to be the rep that persuades HSBC to make their first investment, not the rep working on the eighteenth iteration of their renewal." In true Rich fashion, he made good on that promise and closed a deal with HSBC, and no doubt, there is a rep out there now benfiting from Rich's hard work.

But running a startup & being a part of the founding team has brought a whole load of new perspectives & insights that I thought I would share.

There are Lots of Fakes & Sharks

Firstly, you would be amazed (or perhaps not) by the number of people who brand themselves as "Unicorn Founders" or "successful ex-founders". Most are just trying to sell you something or are endlessly promoting themselves on LinkedIn. Yet, a closer look reveals the majority are either delusional, outright exaggerating their success or simply riding on the achievement of others.

It is often amusing but can also be a huge distraction as some of these people, on paper at least, look very authentic, and it's often very reputable people who might point them your way without doing their homework on the individual.

Raising Capital & Talking to VCs

Without a doubt, one of the most interesting aspects has been working directly with VCs and navigating the process of pitching for investment.

There is a lot of advice out there from many people who have far greater experience than I, but one great tip I learned from a friend was to make sure you block out time for investment calls and do them in one hit (i.e. 1/2 day once a month). If you don't do this, it's so easy to find yourself doing sporadic investment calls across your working week, and it can be a big distraction.

Outside of that, it's just like running a sales process and you need to not be afraid to qualify out as quickly as you try and qualify in a VC. Naturally, if you find a VC that is appealing to your requirements, then make sure you treat them like a customer and sell them on the financials, the product, the strategy and, probably most importantly, your people.

Identifying Talent & Building a Team

Of course, the fun part of building a startup is bringing in great talent and watching how they shape the culture & DNA of the company.

This gets much harder as you grow and scale, something we haven't yet dealt with at ESPROFILER, but it makes the whole experience so much more rewarding when you see how your people make an impact on your results and thrive in the company environment.

We recently ran some skip-level reviews. One of my favourite comments was, "My friends all hate their jobs, but I look forward to coming to work & enjoy what I do." It's amazing to get feedback like this and it's testament to the culture that has been created by our team.

Finding Product Market Fit

One of the hardest aspects for any startup is trying to find & identify market fit, particularly if it's a completely new market segment you are trying to create.

We have found ourselves constantly second-guessing the requirements of potential customers and asking ourselves whether we are heading in the right direction with ESPROFILER, and it's very easy to get sucked into individual customer requirements or get distracted by the competition.

We are still early on in this journey, so we are still very much learning, but we have learnt to trust our instincts on where we feel we should go, ensure that we seek external feedback, but also balance this feedback.

It's amazing when you speak to very seasoned, experienced people how you can get a wide range of views, and it would be easy to get dragged in a particular direction based on the thoughts of one CISO versus another. Ultimately, you will start to find pull in certain directions, but we need to reflect and accept we still have a long way to go before we find our true market fit.

Running a startup is a constant rollercoaster of highs & lows. From the thrill of winning that hard-earned customer to the sometimes-frustrating dance with VCs and the endless search for market fit, it's a journey filled with both tribulation and reward. Ultimately, it's a marathon, not a sprint, and one where the lessons you learn from the fakes & the wins make the journey all the more worthwhile. I look forward to sharing more of our story with you as we continue to grow and evolve at ESPROFILER.

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