I’ve been listening to all of the Reboot.io podcasts by JerryColonna, post his conversation with me. I initially found Jerry’s new- age-hippie style raised some “radar, radar” signals in me. Why? As a CEO Whisperer, Jerry’s work is a truly unique blend of his actual investor experience, penetrating honesty, and, well, Buddhism. I have nothing against this–but I have an unconscious reaction to anything that strikes me as cultish.
I expect this subconscious response is because, as a teenager, my parents became born-again Christians and this decision set off a great deal of heartache and devastation for me, and especially my siblings. I will forever have an instinctive resistance to people who adopt and proselytize dogma as a reaction to their own internal damage. (OK I know that is a heavy bombshell to drop, but this post is not about me, so I will leave it at that for now.)
But Jerry’s advice and practical experience are so often fascinating, brilliant, and on the mark, that I have become a real fan. My latest favorite episode was called “The Hidden Burdens of Work.” Within the two very poignant interviews in the episode, I found the first one actually had the most succinct and best “Go Raise Money” battle plan I have lately heard.
- Helping Sherman articulate the fears he is facing (about not being able to be a successful breadwinner–especially with a newborn). Killer quote from Jerry: “Being a parent is like wearing your heart outside your body.“
- Helping Sherman separate his real responsibilities from the “worst case scenarios” of what happens if he fails to raise funding.
- Gives Sherman a brief but powerful plan for what to do to raise funding. Anyone raising a seed round or facing funding oblivion should listen to it.
Jerry does a masterful job of embracing and recognizing the real fears Sherman faces and then putting them in their appropriate place to free Sherman up to do his job.
The second founder interview with founder Joseph Bassett of Dawn Equipment is super poignant and compelling in the way Jerry gets to the heart of helping Joe face the real monsters that drive his actions and emotions.
This startup stuff is cray cray and dramatic and I love the way Jerry embraces the whole person in helping founders through their lonely hard journeys. I can relate to almost every episode.
P.S. If you get sucked into Sherman Lee’s story, here is his recent Medium update “Raising Money in London Almost Killed Our Startup” and an interesting response to that same piece from his lead investor in London, Doug Scott.