Tracey owned a relatively small business with a partner and after running it for nearly 10 years was made an offer which sounded very attractive as a part of her final exit strategy. She was paid cash and retained a small shareholding in the new venture. Her role was to drive sales and help to grow the total business with the plan to exit after 5 years.
It didn’t quite turn out quite as expected. Tracey is producing a significant proportion of new sales and has ended up as the managing director with a board that is not really assisting her very much.Her dilemma is whether she buys a significantly increased proportion of the company using up all her available cash and other investments, becomes a pure salesperson on a sales contract so that she can maximise her earnings, remain the MD and continue doing her best to grow the business or resign and do something else.
After mapping out the scenarios, and clarifying that Tracey was really not keen to go back to what she had before (i.e. a big stake with no other assets), she decided to approach the board with two options. She either becomes a full time sales person (she felt she could double her income on this basis) or she continues as the CEO but with share incentives which rachet up based on hitting revenue hurdles so that she could end up with 50% of the company by year five.
The board had little option but to accept what was really a win/win proposal. For Tracey it meant facing a lot of hard work and commitment with some level of additional risk but at the same time retaining her assets outside the businness. She was fairly confident that she will reach the targets and anticipates being the owner of 50% of the business in five years. Based on reasonable valuations, this would mean that she would be able to retire and never have to generate any further income from effort.
Thoughtful perspectives on investing and wealth, decision-making and purpose.
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Retirement is about more than money. Before you stop working, try an ordinary weekday with no meetings, deadlines or plans and see what retirement might actually feel like. This practical exercise can reveal how much structure, purpose, connection and spending matter in your future lifestyle.

I’m in the Kruger National Park in South Africa during a short holiday and as I watch an unlucky buffalo being eaten by 14 lions, I’m reminded of how stark the laws of nature can be. There’s no room for sentiment: Eat, avoid being eaten and protect the next generation – that’s it. The rules are clear and breaking them usually means death.It made me wonder whether we - as human animals - are a little too smart for our own good. Maybe applying the rules of nature would make life not only simpler, but also more successful.
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The Rugby World Cup Final is being played overnight and either South Africa or New Zealand will create history by winning it for the fourth time. Ireland and France are two great teams who have fallen short, by the smallest margins. In fact, there is no difference between these four teams.South Africa and New Zealand are rugby nations.
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