They cashed out $160,000 in retirement savings to build a $126M company — now they're running a British soccer team

In an interview with Fortune, Bryan and Shannon Miles explain how, in their mid-30s, they were restless in stable corporate careers. Rather than easing into entrepreneurship on the side, they went all in — cashing out the full balance of their U.S. retirement accounts, called 401(k)s, the American equivalent of a Canadian RRSP — approximately US$160,000 (C$227,000) in cashed-out retirement savings. They founded BELAY, a staffing software company that broke even after 14 months and posted 40 straight quarters of growth. In 2020, the couple brought in a new chief executive officer (CEO), and a year later sold a majority stake in the company for US$126 million (C$179 million), keeping an 18% ownership stake for themselves.

Shannon has said she isn’t naturally a risk-taker when it comes to money, but reasoned that they were young enough to return to salaried jobs if the business failed — and that she would rather risk failure than live with the regret of never trying.

Their next venture, a brewery chain called NoFo Brew Co, connected them with soccer fans eager to watch matches over a pint — and eventually led to actual ownership stakes in the sport. In 2022, the Miles joined an investment group that bought British club Walsall F.C., around the same time actors Ryan Reynolds and Rob McElhenney famously bought Welsh club Wrexham A.F.C. A year later, the couple bought Irish club Drogheda United F.C. and has since taken stakes in clubs in Denmark and Togo.

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What cashing out retirement savings early would cost in Canada

As U.S. citizens, the withdrawal from their retirement fund triggered a 10% early withdrawal penalty on top of ordinary income tax. In Canada, cashing out an RRSP before retirement carries a different, but equally steep, set of costs.

• RRSP withdrawals are subject to a withholding tax of 10% on amounts up to $5,000, 20% on amounts up to $15,000, and 30% on anything above that (5%, 10% and 15% respectively for Quebec residents)
• The full amount withdrawn also gets added to taxable income for the year, which can push a filer into a higher tax bracket
• Unlike a TFSA, the contribution room used for an RRSP withdrawal is lost permanently — there’s no way to recontribute it later

For a couple cashing out an amount similar to the Miles’ — roughly C$227,000 — the withholding tax alone could claim more than C$68,000 before the money even reaches a bank account, with potentially more owed at tax time depending on income bracket.

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Balancing the entrepreneurial risk

For the Miles, the risk paid off. That won’t be true for every founder.