How Losing $1M Taught Me Life’s Greatest Lesson!

After losing a million dollars, an entrepreneur learned to stop fighting her weaknesses and instead delegate them. She breaks down the math: one hour of her high-value work can pay for multiple support tasks. Early experimentation helps you find your genius, then outsource the rest.
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Life is meant to be a beautiful adventure and beautiful exploration. So even in the down times of my life, I've genuinely really enjoyed it and found fulfillment in a lot of those things because I was curious.
What are some of the things that you weren't prepared for stepping in this game of entrepreneurship where you got there and you're like, 'Goddamn, yeah, I was not expecting this.' Yeah, good question.
I mean, there's— I think the big failure that I wasn't really expecting to lose that much money and that so much would go wrong in such a short period of time where I literally, you know, in the game of entrepreneurship, it's— you're always making bets, and ideally you're going to win 6 out of 7 or 6 out of 10, maybe 7 out of 10 of those bets. You know, you're not going to win every one. But I went through during that period of darkness, I went through, I feel like 2 out of 10 were working right. And then you're like, man, your confidence gets rattled and you're like, dude, can I actually do this? Am I meant to do this or should I get a job or what? Just so many things were going wrong and things that would normally work out just did not work out. So, So that was the toughest season for me of recognizing, oh, all right, sometimes I gotta do a better job of protecting my downside. I've, you know, I got more clearly exposed to my own strengths and weaknesses. Where am I really amazing, but also where do I suck ass at? And I got a few of those areas too. Helped me be more honest with myself for the future.
You said about your areas where you suck or where you excel. A lot of entrepreneurs, there's a very big debate where a majority of the entrepreneurs would argue that forget about what you suck at and try to better where you excel in. And some others would think that you already excel in these areas, continue working on them, but you should also work on your sucky expertise because obviously you suck at it and you should maybe get better into it. What do you think? Should we delegate what we're not good at, or should we to a certain degree try and get better at it?
Yeah, you know, I think you should delegate or delete most of the things that you're not so good at. Um, and my philosophy is like, manage your weaknesses and exemplify or live it, lean into your strengths. So like, I am not so good at the detailed work of like operations or legal accounting. I don't wanna fool with that. It brings me death. And, but if I don't do a good job delegating it and hiring the right people, then I'm, my business is also gonna be financially not in great shape. So I need to make sure that I have those things in place. That people are doing a good job, that I have the right people in the right positions. Unfortunately, a lot of this stuff is, you know, freelancer. You can have people that are like $200, $300 a month. And, and the other thing is, is like, if I'm paying someone $40 an hour to go and do my accounting, well, if I'm capable of earning $400 or $500 an hour or $1,000 an hour, well then by doing one good hour of that, I've paid for like 6 months of accounting or whatever, right? Like, you're gonna really, you know, really offset the cost if you know your— because the reality is, if I, if I manage my weaknesses, that means I'm gonna be playing in my strengths more, and there's gonna be a higher market value for my strengths than my weaknesses. So I want to play— I might, like, I might make— let's say I make $1,000 an hour, which is typically what I make. Um, so make $1,000 an hour, then in that 1 hour, um, I'm— I can pay for 1 hour of an attorney at $300 an hour, plus my bookkeeper is like $40 an hour, let's say, plus I can pay for someone to mow my grass, which another whatever, $80. Plus I can pay for a house cleaner to come and clean my house, which would take them 3 or 4 hours for $200. So, oh, and plus, what else? Maybe I pay for my social media person to post, to edit some video. Like they edit 2 videos, that takes them 2 hours. Well, so I just bought like 15 hours worth of services of stuff that is not my genius. With that 1 hour where I'm working in my genius.
That's powerful. So it's all about delegating. Yeah, right.
Okay, well, it's, it's about knowing who you are, knowing how to get a high value, market value for your, your gifts, meaning leveraging them in the right way. Like if you think of a famous footballer In England, I don't know who that would be right now, but if you think of Ronaldo, right, world-famous football player. If he goes and plays baseball, he's in the minor leagues. He's not— He's gonna suck. Yeah, he's gonna suck. Or you go put him in a goalie, he'll be better than playing minor league baseball, but he's not gonna get the $30 million a year that Real Madrid is paying him or whoever is paying him. Right? I don't know what team he's on right now, but I think— yeah, so, but he can do that, that one thing exceptionally, world-class, high standard, and gets paid really, really well for that.
So I can't remember who said this, maybe it was Tim Ferriss or maybe James Clear. It's about focusing on the 20% that, um, results in 80% of the results. I think something like that.
So that's what Tim Ferriss talks about it some.
Yeah, yeah. And so, and what would you say to someone that doesn't— isn't good in anything? Should he, should he try a bit of everything to see where he excels in and then focus on that? Yeah, yeah, yeah.
I think you need to experiment and constantly experiment, but you get more clear about what type of experiments you should do. Like, you're 19, so like like try a bunch of things in your 20s.
It's all about experimenting.
Yeah, yeah, yeah. But you'll get more precise with your experiments as you go along because you have more insight.
Okay. I see this quote wherever you go, which I really like. I'm going to read it right now. To be creative means to be in love with life. You can be creative only if you love life enough that you want to enhance its beauty. You want to bring a little more music to it, a little more poetry to it, a little more dance to it. How does this quote resonate with your personal philosophy or approach to life and creativity?
Man, I think we are born creative individuals and, and that life is meant to be a beautiful adventure and beautiful exploration. So like I, I even in the down times of my life, I've genuinely really enjoyed it. And found fulfillment in a lot of those things because I was curious. And I was, even though I quote, I don't write poetry, but I wanna create beauty with the life I live and the exploration and the curiosity and the, if I see life as a grand adventure, I'm 44 now. So if I see it as a grand adventure, you know what? I'm gonna have a lot of, a lot of adventure in my life versus if it's boring. Life's, you know, I'm just supposed to get a good job and blah, blah, blah, and, you know, build this career when, you know, sacrifice— your worldview and your perspective really shapes who you become and how you show up. So I want to have a great worldview that is very empowering. With the direction I want to go.
And do you believe that creativity necessarily requires a love of life, or can it also emerge from a piece of, like, place of struggle, pain?
Um, I think it's both. Yeah, I think you're— you recognizing the struggle and pain. Like, I heard this great metaphor: this mountain climber gets to the top of the mountain, and he's on the top of the mountain, and guess what? He looks down. Like, he's at the top of the mountain, he's like What's at the top of the mountain? Just rock. Rock and snow. No animals. Nothing's up there. But then he looks down, and the more deep he looks into the valley, the greener the valley is. The more life is there. The more vibrancy. So, in those moments where you're in the valley, you're also in a vibrant season of growth. So, and I, because I knew that metaphor, that actually was part of what helped me pull, helped pull me through the season where I lost $1 million. Like, hey, you know what, I'm gonna make it through the other side of this. It's okay. And I'm gonna, this is gonna be a gift at the end of the day. And I was determined to find the gift. I was looking, hunting for the gifts.
Absolutely love your metaphors.
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