Ahead of a meeting with a potential investor, to what extent have you thought about the mystery that lies in your entrepreneurial “past” and the relevant application of it to your investor’s immediate future? It is fine to be translucent, probably unhelpful to be opaque and not necessary, to be transparent.

For example, an investor would “think” they know me well after a google search through my website, blog, newsletters, public speaking, media contributions, podcasts, published articles, company accounts, social media, and perhaps talking to others. What they wouldn’t know, or at least they’d have to dig very deep, is many of the experiences that have shaped my understanding of the complexity and ambiguity in pulling off successful private company investments:

• Lesson No. 1: In October 1982, “bad losers” make terrible investment partners, and friends or acquaintances, who are “bad losers”, are to be avoided at all cost, especially when you are the smallest kid in the class! Trying my hand at an early entrepreneurial endeavour selling horse racing tips (£5 for a series of “Tiny Tips” three Saturday Nap selections), while a teenager at boarding school, I received zero credit if they won and untold grief, bordering on physical abuse, if they lost.
• Lesson No.2: In March 1992, most business risk management plans make appropriate allowances for catastrophes (hurricanes, earthquakes, wildfires) and with time businesses can rebound but rarely, do they consider the subtle changes in human behaviour and the grave consequences. That thought occurred to me while part of a deposition team seeking to reconcile the impact of a ponytailed fiftysomething psychotherapist, sitting in front of us, who had “groomed” five of his patients to have sex with each other, as therapy. A Boulder, Co. clinic, 8 partners and a practitioner with a 30-year exemplary record, destroyed in an instant, and my employer, his insurer, forced to payout US$10.7 million bucks.
• Lesson No.3: In late February, 1999, no amount of money can turn an entrepreneur’s vision into an organisational reality without the requisite judgement and talent. Here I was whisked from a dusty landing strip in the Grenadine island of Canouan, to a meeting with Antonio Saladino, the urbane Swiss-Italian founder of a luxury hotel and resort development (today transformed by the stylish hands of Irish tycoon, Dermot Desmond). Flirtatious blondes, Donald Trump, unexplained investors, gargantuan real estate development and the uprooting of an entire fishing island culture all with Grenadine ministerial approval. Very Ian Fleming. Modelled on Porto Cervo, Saladino’s plans went awry over failed assumptions about buyers of the luxury villas, the prime guest market (wealthy North Americans, not the bejewelled Europeans he spoke of), and how to mitigate the impact of commercial airlines suspending scheduled flights (no meaningful plan B or C).

There is a hundreds of other rich and humorous stories I can talk to investors about, many not for publication. All help to shape my skills, behaviours and expertise. What could you use to create a seductive rapport with your ideal investor?

Tags: ambiguity, building relationships, complexity, credibility, expertise, investors, seductive rapport, trust