Serendipity, Trust, and Identification: Three Areas that Greatly Influence Mentor-Entrepreneur Interactions

Imagine yourself at a networking event, and you’re looking for a person with an expertise in retail marketing in this crowd of people to mentor you and provide advice about what retailers your business should partner with. Instead, you get stuck talking to the lawyer for thirty minutes, and completely miss the person you should of been talking to on the other side of the room.


From my research, I've learned that finding the right business mentor is a three-pronged problem: it's rooted in serendipity, trust, and identification.


From interviews, I learned that serendipity means two things to the entrepreneurial community, a missed connection and how relationships form. The example of the networking event I had you imagine two paragraphs earlier - the entrepreneur getting stuck in a conversation with the lawyer - that's an example of a missed connection. In an interview with a local mentor explaining how he's met and formed relationships with young entrepreneurs, he said, "... most of it is very serendipitous ... that's how real relationships form. It's pretty hard to find your soul mate at a speed-dating session. Mentorship is a highly personal experience."

Trust is the second pillar governing mentor-entrepreneur interactions. In an interview with a local angel investor and organizer of community tech startup events, he recounted his experiences of organizing exclusive groups and meetings. He argued that the people in the group, even if they don't know each other, trust each other because it's exclusive to the degree that the people within the group know each others value. After my interviewee pointed this out, I began noticing it with the groups people all are a part of - i.e. universities, incubators and accelerators, etc. I think this is why an introduction from a friend proves to be effective.

Learning about trust as one of the underpinnings governing the interactions and meetings of entrepreneurs and mentors makes sense because it lowers the transaction cost on the exchange of information. The Rainforest by Hwang and Horowitt argue that the amount of distrust increases the transaction cost between people that want to exchange ideas, labor, and capital - the life and blood of any startup ecosystem. If there's a higher distrust in a startup ecosystem, then there are fewer transactions occurring between the various denizens of that ecosystem. In other words, people are not willing to seek a return on involvement, because there's a certain amount of risk associated with each transaction. If the risk is too high, and there isn't enough trust to make up for that risk, then the transaction will not occur. For example, an engineer and a business person, both with a similar idea for a product, will be unlikely to work together for a period of time because they do not trust each other.

Identification is simply the mentor identifying the entrepreneur, and the entrepreneur identifying the mentor. I've learned that it's normal for entrepreneurs to seek several strategic experts to advise on various areas of weakness. One entrepreneur summed it up quite well, "I tend to look for weaknesses of core competencies of specific aspects of the business model in the team." This means, a startup may feel comfortable with their product development, but needs advice on customer acquisition or on financial projections. So the entrepreneur will seek out a person who's an expert in customer acquisition or financial projections. This means that the entrepreneur identifies the right business mentor based upon their area of expertise.

The second part, the mentor identifying the entrepreneur has been a bit trickier to find a consistent answer across from mentors. It's also the part I've found to be new and intriguing, because the mentor is looking for an entrepreneur that is coachable. The question now posed is, how does one know if an entrepreneur is coachable? Two of the mentors I had interviewed and observed said they identify a teachable entrepreneur by the questions they ask. I imagine a solution to the problem of coachability will allow for non-mentors hoping to bring entrepreneurs and mentors together, to be able to screen for coachability. This is a vital part to understand if a mentoring system is to be designed.

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