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Bootstrap Fireside Chats – Oliver Bruce, CEO & Founder of PinPoint Media

Oliver Bruce is CEO & Founder of PinPoint Media, a Data-Driven Content Marketing Agency that he launched back at university a decade ago. Growing from bootstrapped beginnings, PinPoint Media now generates a seven-figure recurring annual revenue.

As well as building his agency from scratch, Oliver also hosts the globally leading ‘Success is in the mind’ podcast and is an active investor in a number of high growth start-ups.

A few weeks ago, Oliver sat down and told us his story, in the hope it can be used to inspire the next generation of bootstrap founders, take it away Oliver!

Please introduce yourself and tell us about your business?

My name is Oliver Bruce and I’m a podcaster, investor, content marketing agency owner whose business generated a seven-figure annual revenue. Alongside this work I now invest in startups around the seed and series A stage. My podcast, ‘Success is in the mind’ is in the top 5% globally and covers candid stories with business owners about start up and scale.

Why did you decide to bootstrap your venture, rather than opt to raise investment?

I started my business at university and at that stage I was not really aware that raising investment to start a business was an option. I had no understanding around why I should raise money, so I just began taking the first steps myself. I was running around university shooting content and editing it and then finding time for my uni work during other parts of the day.

At a certain stage we had made enough money to look at hiring someone to support which is exactly what we did. Since then as we’ve grown it’s been a continual process of reinvesting what we have made to scale and grow our capabilities. Whilst that has certainly slowed down the growth two-fold, it has allowed us to be more stable and make better investment decisions.

Despite that, I’m not against raising funds, because there are always circumstances where you might need capital to start, tech would be one of these, but if you’re not in that position it can work in your favour to do all you can before deciding to raise finance.

Tell us about those first few years, how the business grew and some of the top challenges you faced getting the venture off the ground organically.

The biggest challenge was the consistent question of whether to hire someone or to outsource our work. You can run the numbers and make a case for both. If we hire someone full-time then we have to make sure we fill their diary to make them a profitable asset, but if we opt to outsource we sacrifice the security of knowing we have that resource available, and don’t need to go through the process of finding support each time we win a project. So do we invest up front and burn our cash if we don’t fill their diaries, or do we outsource on an ad-hoc basis. For the first few years that was certainly an art that we had to manage.

In the end we decided to hire.

Looking back, are you happy you chose to build this way, and why?

Yes, simply because if you’d given me that amount of money at such a young age, I would not have known what to do with it.

If you were speaking with a potential founder who thinks bootstrapping is not an option for them, what would you say and what are the first steps?

I’d say that bootstrapping does not mean you can never raise investment, but if you can reach a certain stage of development before looking for funding then you should try to do that. Look to prove there is a market for your idea or your service, build that MVP if you can. If you can start generating a small amount of money and then look at where you can accelerate that growth then that is a first step that is not as daunting as suggesting you build the whole business organically.

If you get to that point then an investor will likely see value and you have a higher chance of raising money.

Sometimes you have nothing to lose, so I’d say just start.

What was the most surprising advantage of bootstrapping that you didn’t know beforehand?

Probably the way it grew me as a wider businessperson beyond just the benefits it had for our own business. Bootstrapping gives you a really interesting opinion and perception on how to grow a company, it helps grow you as an individual, personally and in a business sense. You are less about chucking cash around and you are more about the deliverables. You are a lot leaner on your time, you have to learn how to run a business properly, it sets you up very well. You understand balance sheets, P&L forecasts and running a business the ‘old fashioned’ way.

If you look at the top entrepreneurs, many of them had very low initial exits with their early ventures before going on to further success. It’s a process that takes time and has to start small.

Is there something we haven’t asked you which we should, or any final advice you’d like to offer those who are deciding to make the leap?

Firstly, if raising money is not an option and you look to borrow from a bank, they will always say no until you argue your point. Ultimately, they’d rather have the cash over a longer period of time than not at all, so push them.

Secondly if doors close there are always other options, if you want it that badly you will find a way of doing it.

And thirdly go through a phase of family funding if you want to, but the pressure of raising funds from mates and family is much higher than when you do it from an angel or VC. Bear that in mind because it can be an immensely stressful experience.