What’s the Most Difficult Situation You’ve Dealt with as an Entrepreneur?

What’s the Most Difficult Situation You’ve Dealt with as an Entrepreneur?

Question:

Question is what’s the most difficult situation you’ve had to deal with as an entrepreneur?

Answer:

Blake: and I want to hear from you first then I’ll talk about mine.

John Max: OK, so the most difficult thing that I’ve ever dealt with…so like business, anything that happens in business doesn’t really scare me, you know there’s things that I don’t enjoy doing, I mean I don’t enjoy letting someone down, I don’t enjoy saying no, I don’t enjoy…like those typical things in business but like from a project basis or from a work basis, nothing has ever scared me from that, the most difficult thing for me to deal with and, and I…I want to preface this with I love my family and I love my wife, the most difficult thing for me is, is being OK with being misunderstood, and what I mean by that is that when you find something that you that you love and that you like…it’s difficult for you to breathe without being able to do that work, it, it, it… for me especially, I struggle to balance work with anything else and I’m doing, and so the most difficult struggle that I have had is, you know when when I got married, giving enough time and fulfilling on the promises I made as a husband and loving and caring and providing for my wife from an emotional standpoint, not, not a, not a monetary standpoint, but actually fulfilling on that promise, that’s been the most difficult thing for me, because I get…when I’m working, I look up and it’s eight o’clock at night, it’s nine o’clock at night and my wife is very forgiving and very loving and I think that she, you know, she knew she was signing up for because I’m a little crazy in that aspect, but that’s been…the most difficult for me is self-regulation you know, is knowing…is being able to balance and more so integrate, you know, work and other things.

Blake: like how and when to unplug.

John Max: Yes, exactly, and just…unplug 

Blake:so for me it definitely is like having to let a team member go, like having to fire somebody, not for like downsizing purposes, like that I feel I can wrap my head around but like…but actually having fire somebody for performance issues, that kind of thing, that is just very tough to me as a person like I, I consider myself kind and friendly and…

John Max: you just genuinely love everybody.

Blake: Yeah, I love everybody, I love interacting with people and firing somebody and basically like knowing that I on probably the worst day of their lives, or the top 10 worse days of their lives, it troubles me internally, really hard. And as an entrepreneur, you have the situations where you have to sit down with somebody and get real across the table and that’s, that’s never fun, like internally is one of the most challenging moments of my life and I have to level with somebody so that is definitely the toughest part for me for being an entrepreneur.

Written by
John James, M.D. is the CEO of Engine, a modern cloud-hosted ecommerce platform. I paid for medical school with an ecommerce business I founded in my dorm room over twenty years ago, and eventually raised over $100 million in venture capital running Acumen Brands. Email me -- john at enginecommerce dot com.