Thoughts on starting from scratch again at 43

Recently I finished up as CEO of Black Hops, a brewery I started with 2 mates back in 2014, and I’ve found myself starting from scratch.

It’s quite daunting, but I’ve been here before, many times.

The first time was when I quit my job in 2006 at 26. I had just received a promotion and decided to completely quit, go out on my own and start a business. No planning, no experience, no money – just send it.

I was starting from scratch, giving up on my career, fulled with an extreme amount of self doubt.

The business was building websites and elearning courses for people, problem was I had never built a business website before. I convinced someone I knew I could build their website and I went to the bookstore to buy a bunch of ‘Sams Teach Yourself’ books on how to code. This was before WordPress was a proper CMS. My first project was a simple site – I remember being so stoked that I figured out how to code in PHP, HTML and JavaScript, especially the drop down menus that had to work across various versions of Internet Explorer and Netscape. So satisfying spending days and days and finally watching those little transparent fuckers glide down over the header image.

The second project was harder, it was a bigger company and they had an IT Manager who was a Microsoft guy. He requested a full CMS coded in ASP. “I can do that!”. And it was off to the book shop again, since I’d never even seen ASP before.

Quitting my job at 26 to chase something that seemed like such an improbable dream, came with an immense amount of excitement. The idea of working for myself or being an ‘entrepreneur’ was something I read about in books, the idea that I could actually do it myself, after never really doing well at anything in my life was crazy. But I did it, burned the ships and figured it out, and I’ve been working for myself for the 16 years since.

I went through it again at 33 when I realised that “working for yourself” comes with a hell of a lot of downsides. Constant stress, financial insecurity, inability to get a home loan, relationship issues, bad mental health, lack of sleep, low or no pay at times, extreme risk, loneliness and isolation – not to mention turning your back on any real kind of career, kicking the can down the road if you ever do have to come back to a career. After listening to a lot of ‘This Week in Startups’ episodes, I wanted to build a startup, so I sold my web agency for a year’s worth of runway.

It failed miserably, and a year later I was back starting from scratch again, this time with no runway. I created WP Curve, it took off and a few years later sold it in a multi-million dollar exit to GoDaddy.

Incredible, arguably life changing stuff, but it once again put me back here. No job, no career, wondering how to once again start something from scratch.

I started Black Hops Brewing with 2 mates and over 8 years we built it into one of the most loved craft beer brands in the country. Again amazing stuff, but now I’m back here again. No job, no career and worse, no real desire for a traditional career. Not to mention genuine concern that I won’t even be capable of having a traditional career or doing a traditional job. I don’t know how you work for yourself for 16 years doing a whole bunch of completely unrelated shit, and then just go back into the workforce. I don’t even know what job I would get. I’m not good at that many things, I’m just kind of passable at most things and can do things quickly when I’m excited about them.

All of that said, I am excited for a few reasons. First off, after pretty much switching off any personal brand or personal content or any personal business projects to focus on Black Hops, I’m back on this blog writing again, Tweeting again and doing my weekly emails. Not for the brand but for me, and that feels good.

I’m also excited about the idea of doing work that I’m good at. As a CEO of a manufacturing business with 70 staff, I spent basically all day every day doing things I wasn’t good at and didn’t particularly enjoy. And you do that because you raise money from investors, and customers back you, and staff work their arses off for you, so you can’t not do the same. But it’s not fun most of the time, despite what it looks like from the outside. Since leaving I’ve been spending my time designing things and writing and planning out a new startup and those things I’m pretty good at and that feels good.

I’m also excited that I’m in a position where I can have yet another crack at a software startup. I’ve always wanted to start and own a SAAS business, I’ve tried many times and failed, this might be my last shot.

And while I’m petrified about the future, I also have a bit of an underlying suspicion that what will happen is the same thing that has always happened. I’ll figure it out. One way or another, through probably a lot of pain and doubt and frustration, eventually I’ll figure it out, because that’s what we do.

My new project is Jessop, a mobile app that enables staff or supervisors to quickly build and roll out Standard Operating Procedures (SOPs), improving completion rates making the team more competent and safe. I’m raising a round to kick it off, if you are interested or know someone who might be, click out the pitch here.

If you are interested in more content like this, jump on my weekly emails.

Keep creating.

Follow me