The Appeal of the Diversified Solo Founder

By dan - On

If audio is your thing I recently discussed this on my podcast Yarn Solo here.

For most of my career as a founder I haven’t been particularly interested in being a “Solo Founder”. My first foray into business was building websites and elearning tools for companies from 2006 to 2013. I worked for myself, at home mostly and the change from working in a team was really tough. I was lonely, I found it hard to motivate myself to do efficient work, I let most of my friendships die because they were all based around seeing each other by default at work. In the end I didn’t like it and swore to not work for myself, by myself ever again. My next businesses were all partnerships and they put me back into the world of working with people again, first remotely with WP Curve and then in person with Black Hops Brewing.

That came with its challenges too. Things are generally exciting at first when you co-found a business, but work becomes work and keeping a solid partnership going is extremely difficult. And what do you do when either the relationship goes sour or you just can’t agree on a direction for the company to go in? Ultimately you have to exit, there’s not really any other option. 

Sometimes you can sell and achieve a good result where everyone is happy. This is what happened with WP Curve and our 7 figure exit to GoDaddy. We were both ready to end the company, neither of us could afford to buy the other out so we really had to exit – luckily GoDaddy wanted to buy at the time, so it was a great result. 

Sometimes it doesn’t end well. I poured my heart and soul into Black Hops. I launched it putting in $100k which was 100% of my net worth at the time (without counting WP Curve, the value of which was a bit unknown at the time), and built it from an idea in my mate’s garage to one of Australia’s most loved craft beer brands and an 8 figure profitable, super successful business. But when things got challenging and the direction sought by the other directors wasn’t the same as mine, I really had no choice but to walk away with nothing. It was heartbreaking and a year or so on, I’m still feeling the aftershocks of a depressing turn of events like that. 

The idea with WP Curve and Black Hops was always to go big. I didn’t want to start a small business, I wanted to create well known brands and achieve some kind of decent success that was well above and beyond just starting a small business where you work for yourself. So when I left Black Hops my immediate thought was to start another high growth startup. I started working on an app helping companies to build processes, and looked for funding for the idea. That would have sent me down another path of multiple founders, multiple directors and investors. I wasn’t able to get the right investors to buy into it and that ultimately led me down the path of looking back at getting a job or being a solo founder. I briefly explored the idea of working for someone else but there were no obvious opportunities and I honestly feel like after 16 years working for myself, I wouldn’t be able to do it. So that left being a solo founder, and the more I looked at it, the more the idea grew on me. Here are some of the reasons:

Redundancy

I’ve always been of the mindset to go big, focus on one thing and pour everything into it. I still believe if you are young and resilient and you have the right partners and community this is still not a bad way to go. But there’s a massive risk and that is that if the one thing doesn’t work out, you’re left with nothing. Having experienced that over the last year I don’t want to experience it ever again. I don’t want to be in a position where I wake up in the morning with nothing to do, day after day after day. Where I potentially have to step back to work I did years before because there are no other options. Where I don’t have an income and have to sell my dream house to pay the bills. 

Whatever the rewards of succeeding at something big, the risk of falling back to that don’t seem worth it to me anymore. Particularly at my age. It’s easier to re-invent yourself when you’re 30 but at 43 I really have to figure out a long term sustainable way to make money or my opportunities are going to dry up. There are already many aspects of what I do where I feel like the world has passed me by, particularly with things like content and social media. It’s a scary thing. 

At this stage in my life the idea of working on a few things is a lot more appealing. Having many things to work on and choosing what energy I pour into the various projects based on what they need and how I’m feeling is exciting. And the idea that if one of them doesn’t work out, I can fall back on the others is the safety net I feel like I need right now. 

Risk

When you find yourself in a position where you start losing things you’ve worked for your whole life you re-consider risk. I’ve always been a risk taker, particularly in business and many times I’ve put it all on the line, burned the ships and backed myself to make it worth it. But when you build big companies the risk goes to a new level. Making decisions with investors’ money, having personal guarantees for debt finance, being a director of a business with big safety implications. All of these things can lead to life changing negative outcomes. You can go to Jail if you don’t satisfy your safety obligations as a director in Australia. The bank can come after you personally for multiple millions of dollars if you can’t pay back loans you have personally guaranteed. Basically everything you’ve ever worked for can be lost if something goes wrong. This is something I thought about every day and every night running a decent size company. Your life, career, wealth, mental health is constantly hanging in the balance in that state. Is it worth the risk? That’s a personal decision. When I was younger and had less to lose and more time to gain it back I thought yes. These days, not so much. 

Over the last few years I’ve spoken to a few long term business owners who have had phases of extreme success and phases of losing everything. I met one guy who had some amazing businesses and then lost it all. He was 60+ years old, working a full time job in another state flying down Monday and back Friday, consulting on the weekends and also working on 3 startup ideas. He’d promised his wife he’d make the money back so they could retire comfortably, and time was running out. I admire the hustle, but I don’t want to be in that position if I can avoid it. 

The time is now

When I first started out helping people with websites I had to learn from books and Google groups. It was super difficult and very stressful. I remember for my first website I had to design transparent drop down menus that worked on Internet Explorer and Netscape. It took me weeks of reading through books, googling errors, searching through google groups. After a few years of living like this I realised I needed to hire developers, so I did and most of the profit of the business was eaten up with wages for the sake of my own sanity. 

A few months ago I started a new WordPress website support service WP Master. I’ve signed up a handful of clients and have been actively looking after all sorts of issues with their websites. I have a developer contractor on hand if I need it, but despite being not very active in the website game since 2016, I am yet to run into a problem I haven’t been able to fix. Mainly due to how much good information there is out there for maintaining websites these days. Hosts are much better, the plugin ecosystem is much better and support is much easier to access, AI tools can find and solve many problems instantly and most problems that you come up against have been solved before and the solution isn‘t too hard to find. I could never have run WP Curve by myself even if it just operated in Australian business hours, but I can now. 

There are other trends too which make solopreneurship a fair bit more attractive in 2023. For one thing personal brands have exploded since I started out in business and it’s easier than ever to have a social media / content following and build a range of different businesses around servicing this audience. It’s become a very popular career path and access to monetisation outlets is getting easier and easier. You used to have to find a coder to connect to a bank’s payment gateway to even sell anything on the internet. Now the content platforms themselves just send you money! Not that this model is a huge part of my plan but it’s a small part and it’s simpler than it’s ever been . 

Alternative to growth at all costs

In the past the main metric I’ve cared about for my businesses was growth. That’s the startup mentality. With that goal you really have to be 100% in. Any time you spend on the business is time you can help it grow and that helps contribute to the goal. But many businesses don’t operate this way. As I’ve transitioned from a startup founder to an owner of more traditional businesses, I’ve realised that not every business needs 100% of your focus. Having a good solid profitable consistent business is very appealing to me at this point and a business like that might not need 100% of my attention. In fact it might be a detriment to be 100% focused on it, getting in the way of something that’s working quite well on it’s own. 

Utilising your skills

Through the years I’ve reinvented myself in ways that are not in line with a traditional career path. When I sold WP Curve I went from running an online business that was fully remote, to a local manufacturing business that was fully in person. Some skills transferred over, but not many. And after leaving Black Hops going back fully to a startup, I’d take some lessons but many skills would just be irrelevant. 

I figure why not utilise all of my skills? I can write books why don’t I do that? I can manage websites, why not make money doing that? I know a lot more about manufacturing and local hospitality businesses than I did before (I knew literally nothing before), why not utilise those skills? I’ve learned a bit about podcasting, why not have a few podcasts?

I’m excited for the next phase of my journey in business to be one where I take the lessons and skills of the past and apply them in a few different channels so no experience has gone to waste. 

Unequal contribution

In my experience having founders contribute unequally to the business is the biggest source of issues with traditional partnerships. I’ve run into issues like this with every partnership I’ve ever been in. It’s extremely difficult to work out how to remunerate partners, what to do if you think things aren’t even and all the issues surrounding that. My approach has always been to make sure I am contributing my fair share in a partnership. The way I did that with Black Hops was:

  1. I shut down all of my other projects. At the time I had an online membership, I had some direct sales of books and I was active building my personal brand. I felt that the other founders would see this as a distraction so I shut all of this down and only left my passive residual income from Amazon. This was a big sacrifice which I regret now with the benefit of hindsight. 
  2. When my work in the business was minimal I didn’t draw a wage. When I did finally work in the business full time, I always worked in a very specific defined role and was remunerated below market rate for my role, all the way until I exited.
  3. I turned up to work onsite every work day, regularly on weekends and was basically available 24 / 7 to the team and customers. 

Not to say I’ve always been the best business partner either, I’ve had my ups and downs and times where I haven’t contributed equally into partnerships as well. 

That said, those changes are big sacrifices, which I was very happy to make at the time. But it basically meant that I had a job and this is what’s required when you are in a partnership. If you operate as an owner who doesn’t draw a wage, this isn’t required and I’m looking forward to a new business journey where I don’t have a job. The whole reason I started in the first place was to avoid having a job and where it got me was working an extremely difficult job that I wasn’t the best at at times, didn’t enjoy at times and wasn’t paid properly for. That’s what you potentially sign up for when you start a business with other people.  

Attitudes to solo founders and multiple projects are changing

Things are different in 2023 when it comes to solo founders. There was a bit of a stigma before where you had to be part of a co-founding team to be taken seriously. I follow a lot of solo founders online and that doesn’t seem to be the case any more. Even the traditional startup community is a bit more open to backing companies started by solo founders. And the idea of working on multiple projects seems to be almost a given for influential creators in 2023. Everything from food creators on TikTok, Youtubers like Mr Beast or Logan Paul, or even the biggest example of them all Elon Musk, are working on many things at once. It used to be something that was frowned upon, not so much anymore. 

So here’s the plan

Given all of that, for those who have been following me for a while here’s what I’m doing. 

First off I’m going to continue working on multiple content outlets. My email list, my solo founder podcast Yarn Solo, my beer and business podcast Boss and the Brewer and maybe my TikTok cooking channel when I could be bothered because why not. 

From there I’m going to work on projects in various areas:

  1. I have a bit of residual income that comes in from my books that I’ll continue with. I may even consider doing some info products for some of those brands or updating them. If I have another idea for a book I’ll consider writing another one but I’m not a fan of writing a book for the sake of writing one, so I’ll only do it if i feel like I’ve got a decent idea.  
  2. My WordPress support business WP Master is ticking along OK with a handful of clients. I’ll see how that grows organically over time but not push it too hard. 
  3. I’m in the process of acquiring a small hosting company. It’s a small acquisition but big enough to bring in enough MRR to pay the bills and keep me active in the online / website space. It will also give me a list of clients to market the WordPress support offering to.
  4. I’m going to purchase a traditional business that enables me to take my lessons from Black Hops and continue on my business journey in the manufacturing / hospitality space. Ideally something that’s profitable, consistent and under management and something that can utilise my skills in brand building / design and content. 
  5. I would still like to be somewhat active in the craft beer world because it would be a shame not to be. I haven’t thought of what this would involve yet but perhaps there’s something small I can do in that world as well. 

More importantly I plan on enjoying life away from work. I’m in a good place with life away from work and I’ve never really prioritised this. My life has always been about work. I’m no longer going to put pressure on my self to turn up to an office 9-5 every day. I’ll work around the needs of my projects and enjoy my life in the process.

Photo by Matt Bero on Unsplash

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