Investing in a second career: striking the right balance

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By Oliver Cummings CA, Commercial Director at Capitalise

8 August 2017

Olly Cummings is an ICAS member and Commercial Director at Capitalise. He is also a judge for the OYCA Competition 2017, in association with Investec Click & Invest: Olly reveals how he left behind the luxuries of corporate life to develop his dream business.

Working as an auditor, stockbroker and investment banker taught me one thing: fulfilment isn’t just about your bank balance, it’s about believing in the purpose of your company.

Taking a deep breath, I jumped into a fledgling sector - peer-to-peer lending - with a disruptive UK fintech company called MarketInvoice. My time at MarketInvoice inspired me to think about the customer experience in a completely different way and that’s what motivated me to start my career at Capitalise.

It’s a new online platform that uses in-house technology and data analytics to identify the best financing options available for UK businesses and their accountants. What’s great, is that it combines everything that matters to me in business: helping others, using top notch tech and finding smarter financial solutions.

Happy Sundays

But don’t be fooled into thinking I took my decision to leave the corporate world lightly. It involved a lot of planning and I knew that investing in a second career would mean making some sacrifices.

What advice would I give to anyone thinking of doing the same? As obvious as it might seem, expect your salary to drop significantly – and prepare your family for that too. You may be used to taking expensive holidays or driving a nice car, but if you’re serious about starting your own business, you should be putting away as much money as you can in savings and investments – today.

Have those sacrifices been worth it? Yes, 100%. I enjoy my Sunday nights knowing that when I wake up the next morning, I’ll be doing something I love.

The right stuff

There are other compromises to make, too. You may also be used to having a clear, corporate job description, for instance, but in a start-up/SME environment, age and experience simply don’t matter as much as your ability to get things done.

As an entrepreneur, you’re also the master or mistress of your own destiny – which can be a double-edged sword. Setting goals to avoid getting bogged down by day-to-day troubleshooting is critical.

I have one, three and five-year career goals that I review every six months so I know I’m on the right track. This has played a fundamental part in enabling me to make a successful transition to entrepreneurial life.

Taking the plunge

Having a well thought out financial strategy is always important for new businesses. In terms of a financial backstop, as you’d expect, I have invested in a prolific way in stocks and shares. Given my background and business interests, I also have a portfolio that contains finance-related companies and products, like the digital currency Bitcoin.

It may be daunting, but I have found that taking the leap from a safe, well-paid corporate role into the unknown has been hugely satisfying - and the best decision I ever made.

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This blog is one of a series of articles from our commercial partners.
The views expressed are those of the author and not necessarily those of ICAS.


  • Business and Financial management

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