3 lessons from 9 years of startups

Last week it was announced that US cyber security firm, StackPath, has acquired Server Density, the SaaS monitoring company I started with a school friend back in April 2009 – over 9 years ago! I’m excited to be joining the StackPath team to lead product engineering and establish their European HQ in London.

Moving into a larger organisation has given me an opportunity to consider my experience running Server Density. I thought I’d get back into my weekly blogging by writing about what I think are some things that I would do differently.

1. Read more (books)

It is only in the last 12 months that I’ve been actively reading more books, and deliberately allocating time for it. I’ve never stopped reading articles and blogs but reading a book is a different type of activity because of the level of detail.

Last summer I set up a book club with my senior team and we all read a randomly selected book each month, followed by a discussion of what we learned, liked and disliked. This led to many different internal experiments and after reading The Five Dysfunctions of a Team and Death by Meeting, completely revolutionised how I think about running teams.

My goal is to read a book a week, but a common complaint I have is that most books are too long! There’s no real reason why non-fiction should be more than a few hundred pages.

Since the end of last year, I’ve been reviewing/rating each book I read on Goodreads and trying to cover a wide range of topics. I have noticed real differences in how I approach problems and think about the world from reading history, philosophy, science, politics and biographies, not just business books. Indeed, there’s an argument that you should read more outside of the field you spend most time in.

2. Hire senior people sooner

Bringing on more experienced people who can take over running core areas of the business is something I left far too long. It was really only in the last couple of years that I delegated key aspects of the business to senior people who could do a much better job than me.

This seems to be a common problem for founders, often because they don’t want to give up control:

But for me it was more about having the resources to hire the right people. I focused on hiring more engineers to work with me on building out the product. Instead, I should have hired fewer but more experienced people in different areas of the business, not just engineering.

The Mythical Man Month explains why adding more people doesn’t allow you to build software faster. Rather than building a bigger team, I would instead focus on building a more effective team – senior people who have experience to make the right decisions, sooner.

Finding the resources to do this is always a challenge but I believe that founders should find the few areas they should focus on, and delegate the rest.

At the very least that means things like finance, admin, legal. But also ask what else are you spending time on that isn’t good use of your time? What are the most important one or two things you’re doing to push the business forward each day?

This is one of the things that already stands out to me at StackPath. The CEO, Lance Crosby, has done an amazing job at building highly effective teams to run the different areas of the business. The calibre of the people I’ve worked with so far is superb and they are truly empowered to take big decisions.

3. Take (shorter) holidays, more often

As an early stage founder, taking time off probably seems like the most difficult and inappropriate thing to do. When you are covering many different roles it always feels like you don’t have enough time.

But it is never going to be a good time to take a holiday.

No matter how far in advance you plan your break, by the time it comes around there will be some crisis to deal with or some project that isn’t finished yet.

Yet the improvements you’ll get to your state of mind, productivity and ability to come up with new ideas makes up for the couple of days you might not be doing “real work”.

Just like when giving up sleep to work late, you are borrowing from tomorrow to fuel your needs today, not taking a break is sacrificing your long term progress in order to complete a task right now. It may very occasionally be the right choice, but long term debt is always unsustainable.

You don’t always need to take weeks off – a long weekend where you can truly disconnect is probably worth more than a 2 week trip where you’re always checking-in.

Setting your business up so you can step away for a few days is a good way to test the resilience of your people and systems. Hiring a senior team you can rely on will make this a lot easier, and also help you find time for reading!