A joy of my work is that I get to connect often with smart, “out-of-the box” businesspeople that can be best described as "Investor – Entrepreneurs.”
The most talented of these fine folks evaluate opportunities through the complementary perspectives of the two mindsets.
As investors, they do so dispassionately - with the lenses of risk and reward, and of expected value.
As entrepreneurs, they are more operational, more tactical.
They know that numbers on financial statements are byproducts of collective, human effort - of sales, marketing, and operational strategies and project plans, all underpinned by cultural commitments to excellence and to winning.
Now, when things get dicey is when these Investor - Entrepreneurs don't properly distinguish in their otherwise able minds where investing and entrepreneurship do NOT intersect.
The problem reveals itself in a number of ways.
For the entrepreneur, it is a Cognitive Dissonance, a denial of the simple fact that an incredibly large percentage of their net worth and earnings power is often concentrated in a single, and very high risk asset - i.e. their own business.
For the investor, it is the dark and dangerous side of that usually, admirable human quality of Commitment and Consistency.
This is the tendency we all have to stick to decisions that we have made in the past even if and when the original evidence that underpinned those decisions has changed dramatically.
The classic example of this is basing an investment decision on the original purchase price of an asset, its sunk cost, even though the faulty logic of doing so is almost self-evident.
Yet, following this truism, because of our emotional human wiring, is always far harder to do in practice than in theory.
So, how should - let’s call them “Entrepreneur Mind” and “Investor Mind” - properly work together?
Here are three ideas:
1. For Investors, view with an extremely jaundiced eye records and claims of past performance.
Let's be clear, doing so is extremely hard.
Both because of the aforementioned “human wiring” matter, and because the brokerage and insurance industries have a massive, vested interest in manipulating and exploiting this wiring to prevent us from doing so.
To best resist this manipulation, invest like an entrepreneur - pointed toward the future and leaving the past where it rightfully belongs, in the past.
2. For Entrepreneurs, just for a few moments, step in the space of not believing one’s own “propaganda.”
This too, is hard as of what makes entrepreneurs who they are is their unshakeable and often irrational self-belief, in spite of often much evidence to the contrary.
This self-belief serves them well as leaders and as creators, but as shareholders not so much.
And as shareholders, the irrefutable principles of diversification, of long-term and global planning, and of the overriding importance of small differences in return, multiplied over time, so fundamentally apply.
3. And finally, as Investors - Entrepreneurs, to recognize good professional guidance as a success requirement, for the simple reason that our most dynamic competitors are getting it.
And if you are not, then you are wanting.
And in both investing and entrepreneurship, this wanting, this disadvantage, even if small, multiplied over time is usually the difference between failure and success.
What does this look like in practice?
Well, for one, a best-functioning team of professional advisors should include a great strategy and exit planning advisor, a great accountability coach, and a great wealth manager.
And they should all work together, especially and effectively toward that most natural and glorious and appropriate goal of all entrepreneurs and of all investors.
Which, of course, is asset building and earning power.
Built both slowly and methodically over time as an investor and in sudden, large green and creative shoots as an entrepreneur.