Wearing many hats
3 min read

Wearing many hats

Wearing many hats

As an agency owner, one of the biggest challenges is having to juggle multiple tasks and responsibilities - wearing many hats.

Unlike larger companies with specialized departments, as a small business owner, you are responsible for everything from development, sales and marketing, accounting, and customer service - you have to wear many hats.

Some people hate this.

Some people love this.

I see it as a necessary part of getting your business off the ground, and if you do it well, you may not need to wear all those hats forever (if you don’t want to).

This is not SEO targeted AI generated clickbait article, where I tell you how to manage your time, juggle tasks, and stay focused - there are a billion of those articles on the net if you want to google them.

Wearing many hats is your superpower

In the early years of my agency, half of my clients were solo founders trying to build their startups - by paying others quite a lot of money to do so.

They could drop anywhere from $15k to $500k just getting their idea developed, and then another $XYZ on sales and marketing when they realise building it’s the easy part - the hard part is getting a steady stream of paying customers.

If they were successful in getting some initial traction - and hopefully they were - best case scenario they had to keep paying my agency to add new features and evolve as they pivot and try and find product-market fit. And this could still cost tens of thousands of dollars every year, for many years.

But If you can personally build something, attract customers, sell to those customers, deliver to those customers, and build a good ongoing relationship for future work - you are in the 0.01% of people in the world who can successfully do this.

Wear more of the right hats

If you don’t have any idea on how to do SEO, but you’re building websites for clients and confident this is a skill that will add value, and add to your bottom line - then make a point of filling your knowledge gap and go and learn that shit yourself.

Investing in yourself (and your superpowers) will compound over the years as you become an unstoppable force, and add more and more skills to your arsenal.

New technology can feel endless…

You don’t need to learn every new framework or buzzword javascript library - be strategic about what skills will allow you to go deeper, and serve your customers better.

It’s possible that this is web3 or AI.

But realistically, unless you wear these hats already - it’s probably more like sales and marketing.

The hats I wear

I started as a developer. Didn’t care about anything else but code, it’s all I wanted to do - night and day.

I went from junior to mid, to senior, to technical lead.

I built wider skills in client relations, team relations, management, communication, estimation, automated testing -  everything from frontend and backend to middleware and DevOps.

I left 9-5 work to found a startup with some friends. I learnt about entrepreneurship, business, finance, product-market-fit (or trying to at least!), pitching to investors, working super fucking hard, and eventually - burnout.

I walked away from my startup and started a development agency. That’s when I really learn about sales, marketing, building a network (professional and personal), long-term client relationships, the balance of quality and cost, building a team, growing a team, partner disputes, acquiring other businesses, and selling my business.

I then travelled around Australia for a year in an RV, and started Dev to Agency - where I learnt about writing, teaching what you know, idea generation, newsletters, consistency, distribution, Twitter, and building online relationships.

I’m now working on Userdoc - a startup around AI requirements management, where I’m wearing all the hats I’ve worn over the last 20 years of being in the tech industry.

But I’m still learning - SaaS pricing, product onboarding, enterprise sales and about 62,000 other things.


I’m grateful I’ve always pushed myself to keep wearing more hats.

I haven’t done it all myself, as I’ve built some amazing teams - but only once I’ve proven that role needs to exist (e.g. I did sales and marketing until it was time to hire a team etc).

It’s about not having to solely rely on others, and being able to get shit done yourself.

You can build an amazing business wearing many hats - and that can be your superpower.

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