If you are envisioning an entrepreneurial livelihood, it is wise to develop the awareness that you are constantly and always building your network of allies and prospective investors.  No interaction is without the potential to be transformative to your big idea or meaningful to your heroic journey.

I am struck by the tendency in today’s business culture to approach points of contact as goal-oriented transactions as opposed to reciprocal relationships. My pet peeve over the years has become when one of my students or an aspiring entrepreneur asks if they can “pick my brain”. (I find the image of this request disgusting at worst and unfulfilling at best. Why would anyone like his or her brain picked?) Likewise, I am struck by the short sightedness of entrepreneurs who are on the intense and challenging hunt for money who miss the opportunity to engage at a relationship level or in the realm of shared values, rather than the hit and run “do you have any money for me today”.  Conversely, I rarely, if ever, decline a thoughtful invitation to provide some constructive feedback to a committed, persistent business builder. (Yet I am struck how uncommon it is for a maverick entrepreneur to ask for feedback or input when they have finished their pitch before our skilled investment team.)

As investors, we rarely, if ever, invest in a great idea or business plan, but rather in the character, capabilities and commitment of individuals and teams. It is for this reason that it is essential for entrepreneurial leaders to remember that trust,  and mutual understanding are developed over time and require multiple deposits of insight and good faith. Entrepreneurs need to inspire confidence in their investor partners with each interaction. The ‘EEQ’ (entrepreneurial emotional intelligence, my term) and bankability of early-stage business leaders is nakedly apparent in the sub cues of inquiry and follow up. For instance, the green running shoe entrepreneur to whom I wrote in the last posting never responded to the unsolicited advice I sent his way.

I’ve also come to appreciate the unknowable and mysterious dimension of timing with respect to creating investor-investee relationships.  In my own career, it has been the most unexpected and serendipitous meetings that have evolved to become the most powerful business partnerships I’ve experienced.

Entrepreneurial endeavors flow in cycles. Think of them as short, two year karmic trips—the approximate time between your seed and your series A round or between your series A and series B. It will be no time before you are out raising your next round of capital for your present or future venture. For this reason it is useful to see any interaction with a prospective investor, mentor or ally as a point on a relationship continuum that deserves thoughtfulness and respect. The community of professional investors who provide venture capital to entrepreneurs on a consistent basis is small and possesses an impressive institutional memory.

Like it or not, as entrepreneurs, we are always raising money, even when we are not. If we see relationships as touch-points on a relationship continuum and bring thoughtful, gentle persistence to the unpredictable dynamic of timing we are more likely to sprout and grow the kinds of life-long investee-investor relationships that lead to a productive and fulfilling entrepreneurial life.