Jerry Colonna – Independent Life/Business Coach & Former VC

Founders, you are not the first (or the last) to feel the weight of the world on your shoulders, as VC-turned-coach Jerry Colonna told Jason. They also discussed Jerry’s own depression/direction change, the randomness of luck, willing things into existence, self merging with work, how leaders define reality and more.

Some highlights:
0:03:00 Thanks to Walker Corp Law for partnering with us!
0:05:00 Jerry Colonna is with us today.
0:06:45 How did we meet?
0:08:30 Was Geocities your biggest success?
0:09:30 How long have you done Flatiron with Fred?
0:11:00 What was your “existential crisis”?
0:14:15 What is Canyon Ranch?
0:16:45 Where you feeling guilty about doing better than the average person?
0:20:30 Are entrepreuneurs use to being able to will things into existence?
0:24:30 Are all your clients entrepreuneurs?
0:26:00 What are the themes with first time entrepreuneurs & serial?
0:31:45 Is the cost of “being your work” worth it?
0:32:30 Why did you want to be “the guy” of Silicon Alley, Jason?
0:32:45 What did you imagine it would give you?
0:37:45 “How do you create a sense of self that can withstand the harsh world and its harsh need to change you?”
0:40:15 How much do you charge for coaching sessions?
0:45:45 How much of success & entrepreneurship is about resiliency?
0:50:00 Thank ShareFile for bringing you this show!
0:52:30 What’s the biggest win you’ve had as a coach?
0:54:45 Do you think you’re different now that you’re a father?
0:56:00 Have you answered all the demons from your childhood?
0:57:00 How did your dad lose his job?
1:03:00 Why would people be more inspired by hearing that story?
1:06:00 Did family become your dad’s life after he lost his job?
1:09:00 What do you think about working hard?
1:11:00 How do you become elite?
1:13:15 When should someone quit?
1:22:00 Why don’t you coach people to be coaches?
1:23:00 Why do many life coaches seem like losers?
1:29:30 Check out & follow @jerrycolonna

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