When two phenomenal servers meet in a Wimbledon Final, as Sinner and Zverev did yesterday, it is not hard to visualise success or failure is going to come down to a very small number of points. The margins of error are very tight.

In a business setting, particularly in front of a prospective client or investors, a small pool of elite individuals thrive, in those ultra competitive and tight “win/loss” situations, and the great masses fail or walk away blaming their lack of resilience on others’ shortcomings.

While skills, behaviours and expertise, are a huge deciding factor, I observe that the ability to maintain a positive mindset when you are “losing” and the requisite resilience, is the deciding factor. In tennis commenators such as Andre Agassi refer to it as doing what you have to do, to “stay in the fight”.

In tennis, you cannot win if you don’t do everthing to return the serve into the opponent’s court, preferably exerting pressure on the server’s game.

In a business or investment setting, give the other party a reason to challenge their assumptions, provide instant and compelling value, and offer pushback without fear of losing the business.

Play to win, not to lose. You might just surprise yourself with your “win-loss” ratio.

The entrepreneurial risk-taking journey is not for everyone but one critical reason is often overlooked. The propensity of owner-managers to overestimate their ability to manage risks they are taking today and underestimate what can go wrong at the point of realising wealth.

When the risk-taker uses the business as a personal “cash machine” to fund their lifestyle (salary, dividends, drawings tec) a form of co-dependency arises until there is a weird screeching halt at the point of, and post, a sale of the business.

That familiar replenishing cash machine is no longer, you are now exclusively in the investment management business.

Yet a great many small and mid-sized business owners are not good managers of their own personal capital (cash, credit and investment), and many are poorly advised. They leave it too late to change their own mindset, and behaviour and preparation for their new life.

They act like gamblers rather investing to win.

It is like the guy who wins on the first race at the horse racing track but who freely gives it all back and more to the bookies while entertaining his friends, and walks out a loser after the last race.

If you are serious about building, nurturing and realising business wealth for a long and improved life, you need the discipline and skills of a professional investor not a punter.

There are individuals, who exude confidence in their opinions but are rarely accurate with other people’s money (incompetent). Others with uncommon accuracy, who rarely exude confidence with their own money (timid). There are a tiny handful of outliers, individuals who BOTH exude confidence and display uncommon accuracy with their own money (courageous and shrewd).

The ability to triage judges, and build a peer-level trusting relationship with the consistently courageous and shrewd judges (support system), is often a more important predictor of success (business advice and investing) than the actual investment decision taken.

Who are you listening to and why are they ideal for your challenge?

The influx of predominantly US money into European sports (close to 50 per cent of the English Premier League is US owned) has run into European cultural barriers (think Redbird’s difficulties in Milan and the ill-fated European Super League). I consider “culture” is simply that set of beliefs, which governs local, regional or national behavior. Hence, if you want to change a local fanbase or a national sport’s “culture” you have to change the belief systems or the people with inappropriate belief systems.

You merely have to demonstrate to key leaders what’s really in their best interests and change their beliefs (e.g. changes to the financial structure of their club or their league is not to be conflated with our need for the club or the league’s survival or upward or downward mobility via promotion and relegation). I’ve done this all my career.

Here is the kicker, scale matters, as does accepting what level of power, control and influence you possess over events within your control, and what flatly you don’t, BEFORE throwing your hat in the ring.

Changing culture in a large “corporate” or a young, commercially-oriented and owner-driven sport’s team or league (most US sports leagues) might mean influencing or replacing 50 or 100 key exemplars. However in a sport such as European football, in Rome or Newcastle or Glasgow you are now trying to change a very large, multi-generational, disparate, and high vocal and emotional constituency. Politics, economics, civic, media and religion are intertwined with your capital. You are dealing with the Milanese “ultras” and local politicians’ patronage that is derived from multiple local power brokers. Many, who don’t play by your rules or societal norms. It is like comparing autocracy in Qatar to democracy and bureaucracy in Indonesia.

No one believes what they read or hear in the media. They believe what they see. The process is the same: change the beliefs, which will be manifest in new behaviors, and people will see that and react appropriately.

However don’t over-estimate your ability to manage the risks and underestimate what can go wrong, at crucially, different levels of scale, and influence, in Europe’s oldest sports teams and leagues. Hubris.

My teenage daughter routinely obsesses about the “dress code” for parties we are invited to, as a family, down to the type of jewelry or shoes that she should be seen in. When the whole point of the host wanting her there in the first place, is to see a happy and enthusiastic child with something to say and entertain everyone with.

I see the same obsession with financial services entrepreneurs, and indeed, some of their capital raising advisers, on the nuances of their perceived technological capability when the predominance of their value to others is the superior quality of the management team (skills and passion), the growing market needs they can effectively serve, and their ability to make their ideal investors look smart after backing them (impressive return of capital).

Don’t get distracted by the minutiae when it doesn’t answer the immediate “exam question”: am I looking at a superior and ideal management team with a distinctive competency to address superior and enduring market needs, and in turn, generate me (an investor) superior returns? “Yes”, let’s book a meeting. “No”, let’s move on.

If your attempts to educate your client or your investors on the dramatic improvement in their condition, and measures of progress and success, are largely left until after terms are agreed and/or you fold at the first sign of resistance (desperate not to lose the business), don’t be surprised if they struggle with an ROI calculation or worse, they impose their metrics on you. When your fee or their invested capital is the only clear metric, you have lost control of the discussion.

Three metrics need to be established at the pre-proposal and negotiation stage: short-term measures (sales reports etc), long-term measures (changes in buyer behaviour, market repute etc) and client or investor-specific measures (in wealth, assets under management or for an investor, ebitda or margin growth over the annualised period).

If “value for money” is very much in the eye of the beholder, why do businesses and the media insist on publishing “data-led” rankings, lists and assessments where the methodology applied is rarely how customers think or act? Click bait?

A UK survey today in Britain’s Daily Telegraph tried to assess private school education based on the very blunt assessment of the percentage of children earning a top grade in their 16 and 18 year old exams and divisible by the school fees paid. Next to no parent would use those metrics for their child’s secondary education if they possess the means to make those lifestyle choices.

Chatting to a friend who has been battling cancer and has had to overcome the sudden death of a partner this past 3 months reminded me that when we think times cannot become more volatile and disruptive, there is a high chance they can. It is what we as risk-takers do about it, the preventative and the contingent action we have in place and readily at our disposal that we must focus on. Not trying to predict future risks or their unknown timing. Whether it is a business, investment or personal endeavour, how well do you understand the risks you are taking now, and how confident are you that you have the ability to mitigate what can go wrong?

In this period of increased cost of capital, a great many HNW individuals are being increasingly exposed to potential buyers of personal assets in private sale situations, who are promoting unethical structures and unethical sources of funds. It is duty bound on both the individual personally and their advisers to conduct appropriate due diligence. To take their time and run a rigorous process.

Here is a list of sources that should be “mined” to form a clear and unambiguous picture, and the basis for testing a prospective buyer’s intentions. If you overlook these basic steps, and/or fear to ask uncomfortable questions for fear of the buyer walking away, you only have yourself to blame.

Sources:

• Word of mouth feedback from your trusted peers and their advisers
• Business associates
• Advisor associates (accountant, tax advisers, personal and corporate bankers)
• Investor associates
• Family and Friends
• Community and Interest group members (arts, culture, sports, local communities, charities etc)
• Other market sources (eg credible auction houses, intermediaries, media reporters)
• Prior publicly-reported or private sales situations
• Public media stories
• Public sales records
• Public records of incorporation or taxation (eg Companies House in the UK, Moneyhouse in Switzerland, Dun and Bradstreet in the US)
• Google search

We live in an unprecedented age of transparency on the overwhelming majority of individuals. That has pushed the unscrupulous to be plain unscrupulous or to hide behind multiple companies, structures and opaque sources of funds.

While the job is harder in private assets with private investors in jurisdiction that enable privacy barriers that is no excuse to not apply the requisite discipline and accountability to determine if you are dealing with a legitimate and ethical buyer, anywhere globally.

When you don’t take trusting peers at their word, for example, their reasoning why they didn’t invest or partner with your firm, after asking them what you could have done to earn their support, you are the problem (overthinking).

Of course if you don’t see the other person or they you, as a peer and implicitly trustworthy, then both of you have skipped an essential part of the relationship building process. Any analysis is redundant.