Overcoming the Darkest Lows of Entrepreneurship | Real Stories & Solutions

1 Jul 2024 · 39 min
38:49

In this candid interview, host Mike Michalowicz and guest Rich McFarland trace Rich’s four‑decade entrepreneurial journey—from early successes building service‑bureau style software companies in the 80s and 90s, through a lucrative dot‑com exit, to a cascade of personal and financial catastrophes that included the dot‑com bust, the loss of his father, a newborn child, and a severe depression. Rich reflects on the role of ego, greed, and misplaced confidence in angel investing, and how luck and timing amplified both his rise and his fall. He describes the emotional fallout—shame, self‑blame, and suicidal thoughts—and the practical steps he’s taken to recover: journaling raw emotions, repeatedly practicing self‑forgiveness, adopting a profit‑first financial discipline, and seeking purpose through helping others, community building, and new business ventures. The conversation also explores broader themes of entrepreneurial myth‑making, the danger of equating self‑worth with net‑worth, and the importance of grounding success in non‑financial values such as family, health, and service.

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