How to Create a Successful Mentor/Mentee Relationship in a Startup

"It is tedious to tell again tales already plainly told." - Homer, The Odyssey

A lot has been written about mentorship, especially in the entrepreneurial and millennial communities. Is it a productive process, a waste of precious time, or somewhere in between?

To determine the answer, let’s go back to the end of the 8th century BC. Scholars believe that this is when Homer wrote the famous epic, “The Odyssey” somewhere in Ionia, Greece. The poem mainly focuses on the Greek hero Odysseus (known as Ulysses in Roman myths) and his journey home after the fall of Troy.

"Mentor" was the name of Odysseus’ friend who served as an adviser to Odysseus’ son, Telemachus. According to, the word mentor (similar to Sanskrit man-tar or “one who thinks” and the Latin form of root men- or “to think”) morphed over the centuries into the following definition:

[men' tawr, ter]  noun

  1.  a wise and trusted counselor or teacher.

  2. an influential senior sponsor or supporter.

Naturally following that is the related definition:

[men' tee]  noun

  1.  a person who is advised, trained, or counseled by a mentor.

The mentor/mentee relationship, going back almost three millennia, is a proven process regardless of the form (individual, group, face-to-face, utilizing communication technologies, etc.). It is a powerful tool in sharing experiences (good and bad) from one generation (experienced entrepreneur) to the next (first-time entrepreneur).

In a start-up environment, a successful mentee is one who is open to learning from a mentor sharing experiences on everything associated with launching and growing a company (both business and personal). Again, the mentee must agree and believe that he/she doesn’t know it all and can benefit from the mentor’s insights. The mentee must trust the process.

A successful mentor is one who shares experiences without assigning tasks or “should-ing” on the other person (“you should do this”, “you should do that”). The mentor will hold the mentee accountable to him/herself, but with respect and understanding - not babysitting the mentee. The mentor will share with the mentee honest and insightful input - all without an expectation of a “return” on his/her investment of time and knowledge. The return for a mentor is knowing that he/she is giving back and that the mentee is growing and thriving as a result of the mentorship process.

As Homer said of his epic tale, a comment that today applies to the outgrowth of entrepreneurial mentorship, “The journey is the thing”.


If you're a startup founder interested in learning about the mentorship program that is a part of The Junto Institute, or if you are interested in mentoring at Junto, click below.