The Covered Call Podcast Podcast
Aug 13, 2026 · 1 hr 30 min · 14 segments
Lobo Tiggre shares his journey from a contrarian thinker to an independent speculator, emphasizing the importance of thinking differently, understanding market dynamics, and the true meaning of…
Lobo TiggreGuestJasonHostLovisHostWell, I wouldn't even say that's necessarily bad news, right? I think that it just is a Maybe a hint to make sure that people also look at who they hang out with, right? It's degrees of separation.
Yeah, because, well, it's also this thing of like, there's a saying, I don't know, I didn't check if it's true, but like they say, you become the average of the five people you spend the most time with or something like that.
And if among those five people is nobody who's substantially more successful and something that you care about, then you've just flattened your chances to do that, right? So I think that's, you know, I mean, the way you framed it, it's like, well, it's not necessarily repeatable because not everybody can be Darkeese's friend.
But then at the same time, there's plenty of successful people out there that are worth, you know, building a relationship with, I would say.
So
why not do that?
Yeah, so quick, quick anecdote.
So when we started the covered call, you know, we connected with some friends that are close to us that we perceive as living a free life.
But very, very quickly, somebody also called Doug and Rick to our attention.
I was like, you should really talk to these guys.
And we're like, Rick was we were well aware of and we're like, yeah, we'd love to.
Can you introduce us? And they did.
And then Doug was like, I actually didn't have him on my radar before.
But then that conversation was like, I mean, mind blowing is an understatement, right? It was very, very fun.
So it's interesting that the freedom seeker space is you think is pretty large, because so many people make like their thing about freedoms, like, oh, yeah, if you want to be free, you know, you got to be in franchising, or you can be in real estate, like everybody's has like a freedom pitch.
But then if it's more of a personal journey thing, I feel like it condenses down and pretty quickly to two guys like you and Doug and Rick, etc.
Many others that have we've been lucky to have on our show.
So harpen on freedom some more.
So what does it mean to you to be free? And when it's freedom, like freedom can be an abstract term, right? It can also be used as kind of what I just said, like a little bit oversold of a term.
But where does it stop being abstract for you and becomes personal?

Well, one way to... maybe visualize this is, and this may sound abstract, but to me, I experienced it quite physically.

You know, if you have freedom, you know, it's thought of as negative freedom, freedom from political rights are negative freedoms, right? Freedom from interference.

If you have personal power in your world, you've created room to operate in, freedom, space for your own actions, your own wishes, your own goals, that space around you can be physically manifested.
Well, I wouldn't even say that's necessarily bad news, right? I think that it just is a Maybe a hint to make sure that people also look at who they hang out with, right? It's degrees of separation.
Yeah, because, well, it's also this thing of like, there's a saying, I don't know, I didn't check if it's true, but like they say, you become the average of the five people you spend the most time with or something like that.
And if among those five people is nobody who's substantially more successful and something that you care about, then you've just flattened your chances to do that, right? So I think that's, you know, I mean, the way you framed it, it's like, well, it's not necessarily repeatable because not everybody can be Darkeese's friend.
But then at the same time, there's plenty of successful people out there that are worth, you know, building a relationship with, I would say.
So
why not do that?
Yeah, so quick, quick anecdote.
So when we started the covered call, you know, we connected with some friends that are close to us that we perceive as living a free life.
But very, very quickly, somebody also called Doug and Rick to our attention.
I was like, you should really talk to these guys.
And we're like, Rick was we were well aware of and we're like, yeah, we'd love to.
Can you introduce us? And they did.
And then Doug was like, I actually didn't have him on my radar before.
But then that conversation was like, I mean, mind blowing is an understatement, right? It was very, very fun.
So it's interesting that the freedom seeker space is you think is pretty large, because so many people make like their thing about freedoms, like, oh, yeah, if you want to be free, you know, you got to be in franchising, or you can be in real estate, like everybody's has like a freedom pitch.
But then if it's more of a personal journey thing, I feel like it condenses down and pretty quickly to two guys like you and Doug and Rick, etc.
Many others that have we've been lucky to have on our show.
So harpen on freedom some more.
So what does it mean to you to be free? And when it's freedom, like freedom can be an abstract term, right? It can also be used as kind of what I just said, like a little bit oversold of a term.
But where does it stop being abstract for you and becomes personal?

Well, one way to... maybe visualize this is, and this may sound abstract, but to me, I experienced it quite physically.

You know, if you have freedom, you know, it's thought of as negative freedom, freedom from political rights are negative freedoms, right? Freedom from interference.

If you have personal power in your world, you've created room to operate in, freedom, space for your own actions, your own wishes, your own goals, that space around you can be physically manifested.
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