My biggest strength is also my biggest weakness

My biggest strength as a founder is also my biggest weakness. As a founder of a small bootstrapped business, I care.

Caring means reaching out to customers via Twitter, helping them build an email template, which they now use to contact their hundred thousand subscribers and which has paid-off ten-fold in recommendations and virility with our brand mentioned at the end of their email.

But on the flip side caring means I spent a good hour this morning agonising over a customer who had cancelled their plan after 2 years using EmailOctopus. We'd got to know them reasonably well through interactions on Support, so when they cancelled to go to a competitor it hurt. That agonising did not achieve or solve anything and we have thousands of other customers to serve, it was irrational.

When we care too much, sometimes we do irrational things. Sometimes we take the safe option, by getting what Patrick Campbell calls the founder 'scaries'.

So sometimes it helps to step back and view the product outside of that lens.

Over the years I've been afraid to do things. Things like increasing prices from their ridiculously low baseline as it might upset our customers and not wanting to add a pop-up sign-up form because it might impact our 'brand' (narrator: They had 50 customers, they had no brand).

But actually, some of my best work has been where I've abstracted myself a little away from the business for a minute. There are multiple ways to do this, but one massively impactful way (again recommended by Patrick Campbell) is by asking "If a private equity firm bought my business today, what would be the first thing they'd do?".

That question alone pushes me out of my comfort zone and forces me to prioritise the things that'll make a material difference to EmailOctopus in the long run.

It is good to care, but we've also got a business to grow.