0:00:00
Caleb, welcome to the podcast.
0:00:06
Thanks for having me, Jake.
0:00:07
Appreciate it, man.
0:00:09
Yeah, very excited for today.
0:00:10
And the reason being is I’m going to learn something very specific.
0:00:15
And where I want to start, we’ll tail off into God knows what.
0:00:18
But on NOSTA, we were talking about the options strategy that you’ve been applying.
0:00:25
and I read lately it’s probably the same strategy,
0:00:29
but on top of Bitcoin with the Ibit ETF.
0:00:33
But it sounds like you’ve done it before
0:00:35
with other asset classes.
0:00:37
So first of all,
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what is a covered call option strategy
0:00:41
and how are you applying that
0:00:43
to your current Bitcoin use case?
0:00:46
Yeah, so it’s a handful to unpack.
0:00:50
So I’ll do my best to-
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Take your time.
0:00:53
The most important thing.
0:00:55
So first things first, there’s two sides to the options.
0:01:03
There’s the covered calls and the cash secured puts, right?
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And both of them generate premiums, which are essentially cash payments that hit your brokerage account.
0:01:16
And so I’ve been in the markets a long time.
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I come from a traditional market background, right?
0:01:20
So I feel like every Bitcoiner has this like fork in the road from pre Bitcoin and post Bitcoin. And, and so I was already doing this before I was into Bitcoin and before I, you know, wanted that to be the primary asset class that I kind of hold my, my worth.
0:01:41
in. But we all have our own skills, right? We all have our own set of skills. And so
0:01:47
I asked myself and kind of kicked around the question, how do I continue to do what I do,
0:01:56
but I can’t unlearn what I’ve learned about Bitcoin? Because generally the two things
0:02:01
don’t mesh really well. You hear, stay humble, stack stats, and I believe that.
0:02:07
So generally people will abandon traditional markets, right?
0:02:13
And they’ll start buying spot Bitcoin and they do that.
0:02:16
So I wanted a way to utilize what I learned and continue to utilize that skill set while
0:02:26
allowing it to help me build my Bitcoin position.
0:02:29
So a covered call through the Bitcoin lens is thanks to the ETFs finally being proved after years of just rumors and things like that.
0:02:41
We finally got Bitcoin ETFs.
0:02:45
And so now I can allocate traditional funding and traditional brokers towards that.
0:02:51
I can sell call options on iBit, which is essentially an agreement.
0:02:57
that I agree to sell the shares at a higher price at a date further down the road.
0:03:04
And simply for entering into that agreement, I get an instant cash payment.
0:03:08
I then take those cash payments, start the process of withdraw the cash,
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send the cash to my bank, bank to where I buy Bitcoin,
0:03:19
buy the Bitcoin and send that Bitcoin to a wallet, right?
0:03:22
So it kind of sets off this domino effect now of a weekly transition.
0:03:27
So I do this once a week on Mondays.
0:03:30
And then obviously by the time the money moves, it’s part of why we need Bitcoin.
0:03:34
Right.
0:03:35
It takes till Thursday or Friday to actually purchase Bitcoin with that money
0:03:39
because it has to clear, it has to transfer, it has to settle
0:03:43
and all those things.
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So it’s a week long process, but I’ve essentially taking it and added it to Bitcoin.
0:03:51
I don’t know if that makes any sense, but that’s that’s
0:03:55
It’s awesome.
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I can see quickly how the workflow develops.
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It’s like, okay, now that the ETF exists,
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what price am I comfortable selling an option at in the future?
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And what premium do I get for that?
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And presumably that’s a scale, right?
0:04:10
If you say, oh, I’ll sell it at 250 grand, it’s sitting at 50.
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It’s like, well, that’s really unlikely.
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I’ll sell it at 75K.
0:04:17
It’s like, well, that actually could happen.
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And that premium adjusts as a result, I guess.
0:04:23
Exactly.
0:04:23
And the beautiful thing is every contract that you take comes with a mathematical probability based on real time metrics, basically.
0:04:33
So I know going in, if I have an 85% chance of maintaining my shares or a 92% chance or whatever it may be.
0:04:42
So obviously, the higher your odds are of maintaining your share.
0:04:49
So say I really just want the cash flow. I really don’t want to sell my Ibit. I can take a contract that is very unlikely to be called away. So the tradeoff with that is the cash flow is lower, right? You’re not getting paid as much.
0:05:05
So you have to find the sweet spot where the odds are still in your favor, but the juice is worth the squeeze, so to speak.
0:05:13
And so that’s pretty much where I like to live in that 75 to 85 percentile range where the odds are still pretty strongly in my favor.
0:05:24
But they’re skewed in a way that if things go wrong, there are some some backdoors as well.
0:05:32
Like one, you can just pay the going rate and get out of the contracts, right?
0:05:36
So you’re going to take a loss technically if you do that.
0:05:40
Or there’s a great, great tool called rolling your contracts, which is essentially kicking
0:05:45
the can down the road.
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You close out the current contract and simultaneously open a new one.
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It’s further out down the road, higher up strike price, and you try to make a neutral
0:05:56
premium exchange at best.
0:05:58
So this allows you to benefit from the cash flow and the upside, right? Because that’s the big thing with Bitcoin is we have, you know, 2025 kind of lulled us to sleep a little bit.
0:06:14
But the reality is, you know, Bitcoin could go from 90 to 150 in a very short time period, right?
0:06:21
So if you have any existing contracts, you know, you could be capped on your upside rather quickly if that move happens.
0:06:30
So you need to understand how to navigate out of that should it happen.
0:06:34
And there are ways to do that.
0:06:35
Now, it’s not perfect.
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There’s always tradeoffs.
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But yeah, that’s kind of the flow of setting this up.
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and you can do a traditional assets too. And I haven’t completely abandoned that. But the great
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thing is the traditional assets, the cash flow they produce still flows to Bitcoin for me. So
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I’ve essentially used it to build a Bitcoin position through recurring routine cash flow from this.
0:06:59
Interesting. So in some ways can be summarized as like, this is a form of financial engineering,
0:07:06
and it’s a sophisticated, would you even call it investing? Or it’s more like trading, really,
0:07:13
the process that I love is the traditional world or what we were born into and then the future
0:07:23
and it’s like okay well I know how to do all this stuff how does it work with Bitcoin and that’s why
0:07:28
you get these extraordinarily unique conversations as podcasters because everyone’s life’s different
0:07:33
and they bring different skills to the table and because money is the other side of every single
0:07:39
transaction you will ever have, well, inevitably, everyone’s skill set is also reapplied to Bitcoin
0:07:44
in some way. What I particularly love about this is it’s a way of putting your money,
0:07:52
you’re getting your money to work harder for you. And that is a great capital play,
0:07:57
providing you have the intellectual property to actually do it, right?
0:08:02
One question, just from a very simple perspective, to where does the cash come from to buy the IBID
0:08:08
in the first place. Yeah, exactly. So, yeah, so that and that so you just nailed a lot of things
0:08:16
with what you just said. You know, some people use their hands and they go manually or consulting
0:08:23
or whatever. Yeah, exactly. You know, and this is just the skill set for me. So, you know, I come
0:08:28
from a background. I’ve been an investor my whole life. I got out of college and just had always had
0:08:34
a fascination with it. So I began investing immediately and just building up my investments
0:08:41
early. And so I was part of a small business in 2019 that got acquired. I got a small payout that
0:08:52
came with that as a minority owner. And even as a minority owner, you get this lump sum to add
0:09:00
to what you’ve already been working on for a decade.
0:09:05
So January 2020 rolls around
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and my contract with the company
0:09:10
kind of came to an end after the transition.
0:09:13
And so I’m sitting around and I’m faced with,
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okay, well, what’s next?
0:09:17
And I had this money and I’ve been an investor.
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And so I’m asking myself,
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is it real estate that I get into?
0:09:25
Is it, do I just continue to plow money
0:09:28
into the stock market?
0:09:29
And at this point in my life, I had some Bitcoin, but I didn’t understand Bitcoin. I had Bitcoin as just like a small percentage of a speculative portfolio. So I wasn’t quite there. And 2020 was kind of the year I felt on that rabbit hole.
0:09:45
So it all led to me having a lump sum of capital just sitting and saying, well, what can I do with this?
0:09:53
And I eventually fell on this rabbit hole.
0:09:57
It took a few years to perfect the strategies.
0:10:01
And then so my thing is, as long as it is continuously producing outstanding returns,
0:10:08
We had a 46% CAGR in 2023, a 44% CAGR in 2024.
0:10:18
And we were at 25% six months into 2025.
0:10:24
I haven’t done that year-end review yet for the whole year, but it’s trending along those
0:10:29
same lines as far as the compound annual growth rate.
0:10:32
So to pair that with Bitcoin, I start to think, well, I could take this lump sum of money and I can buy Bitcoin and I can be done.
0:10:43
Right.
0:10:44
That’s.
0:10:44
But then two problems come.
0:10:46
The cash flow stops.
0:10:48
And also, like, that’s the amount of Bitcoin I’m going to own.
0:10:53
Right.
0:10:53
I can’t get any more because that’s that’s my worth right there.
0:10:58
Now I can go to work and I can produce cash some other way.
0:11:02
But in my head, I know the returns that I’ve produced in the past doing this. And I say, OK, well, if I can do this for just two years and get a 45 percent CAGR, I have essentially replicated my pile here with my pile here.
0:11:18
So essentially two years at 45 percent, you’ve doubled your money. So my goal was, well, let’s just do this instead and push all the cash flow into Bitcoin and see what happens.
0:11:32
And so thankfully, Bitcoin didn’t run away on me.
0:11:35
It was something that that has been had some obviously had some volatility up and down, but has been choppy just from a standpoint of it gave me the time to bet on a position doing this.
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And so hindsight’s 20-20.
0:11:50
Maybe this doesn’t work at all.
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Bitcoin rips and you say, oh, I should have lump summed in while it was, you know, at 70K.
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But thankfully for me, it did work.
0:11:59
And it is something that allowed me to replicate that position through cash flow from the original lump sum of cash.
0:12:07
So now, because of that, I’m pretty married to having both exist for in my life because you need cash flow.
0:12:16
And and so this continues to double as a cash flow creator that flows into Bitcoin, but allows me to exploit what I know and what I spent years learning and doing.
0:12:26
So that’s kind of what the whole cycle for me.
0:12:32
I love it, Caleb.
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Well done.
0:12:34
Really amazing progress.
0:12:35
It’s cool.
0:12:37
So many directions I want to go in, but to continue to kind of pull this strategy apart,
0:12:43
some obvious advantages to the cash flow is the debt market.
0:12:48
And maybe you want to buy a house.
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It’s like, okay, I need to get a mortgage.
0:12:52
One of the difficulties I’ve had is just a pure Bitcoin buy and hold
0:12:55
because you don’t create an income.
0:12:56
And so the debt boys are like, mate, you have no demonstrative affordability.
0:13:00
You want to buy a house, but you need to have the capital to do that because I can’t lend
0:13:04
you anything because I can’t prove you’ll pay me back.
0:13:08
And it’s that case of like, yes, of course, like the monetary system that we were born
0:13:13
into has its problems.
0:13:14
But equally as an investor, it’s like, what’s the playing field?
0:13:17
Okay, well, if you can actually take some leverage in a smart way, then that also makes
0:13:22
sense because in theory, you do it in a sophisticated manner and not too much risk, etc.
0:13:28
So I’m all for using the tools that are available.
0:13:33
And okay, so what intrigues me then is, okay, so you’re creating that.
0:13:37
And so those CAGR numbers that you’re mentioning, that’s not the Bitcoin price itself.
0:13:41
That is the return on the capital employed for this specific strategy.
0:13:47
Correct. So if Bitcoin is doing itself 25%, I mean, last year it was actually down, right? My net asset value on January the 3rd versus 2025 versus 2026, actually 2026, I had a horrible year. And during that process, I made some reallocations in some real estate, which I didn’t own before. And that was expensive process. And we also lived without an employment contract for a year. So there’s a number of reasons why it happened.
0:14:14
But the main one was the Bitcoin price.
0:14:16
Just didn’t run in the way that I expected.
0:14:20
Now of course the timeline that you take in some ways the calendar that we live by is a totally arbitrary thing to Bitcoin Bitcoin doesn care if it the 1st of January 2026 or 2025 right It this whole new thing
0:14:35
But okay, so how replicable is this strategy you’ve developed for other people?
0:14:40
I’m immediately drawn to the idea of like paying you some kind of consulting fee
0:14:44
to learn it in more specific details or wrapping it up in some kind of course
0:14:47
or running some kind of fund.
0:14:50
So where do you take it from here?
0:14:51
And I know dad life is just around the corner.
0:14:56
Because another thing for me that’s so cool about the buy and hold of Bitcoin, it’s your time.
0:15:00
You get your time back.
0:15:02
You’re like, oh my God, well, I’m not going to go work for someone else.
0:15:05
I’m going to be at home.
0:15:08
So there’s lots to draw from there, Caleb.
0:15:10
But what resonates the most?
0:15:12
Yeah, you’ve hit the nail on the head.
0:15:15
And to take this back a little bit, exactly as you said, I started on X, just like a lot of people who’ve made their way to Noster have, and literally just documented my journey, shared out loud, and did consulting for a long time.
0:15:34
And what I learned was I didn’t love the, it was great at first.
0:15:42
And then as the strategy worked and performed well and my follower base grew and word of mouth grew.
0:15:51
And then I was spending six to eight hours on the phone a day with just different hourly consulting.
0:15:57
And that wasn’t the way that I wanted to spend my life, you know?
0:16:03
Interesting.
0:16:04
Actually, the sign behind me, it started as that. I started a little investing group, so to speak, where we’ve put together our frameworks, we’ve put together our tools and even all of our trades go there.
0:16:23
And we essentially believe that many folks can learn this if they want to.
0:16:33
It does have some nuance and you got to want to learn it, right?
0:16:36
Like, so I wouldn’t say everyone can learn it, but I think that those who really want
0:16:42
to learn it can, if they come in with the appropriate demeanor, the appropriate expectations
0:16:48
and things like that.
0:16:50
Because we always say it’s not sexy.
0:16:53
We target a half to 1% a week.
0:16:57
And at a glance, and especially to an inexperienced, you kind of scoff at that.
0:17:02
You’re like, I know a guy who did 10% in one trade.
0:17:05
It’s like, okay, but layering a half to 1% weekly on top of each other week in and week
0:17:14
out really adds up, right?
0:17:15
It’s what leads to those compound annual growth rates.
0:17:18
So we launched a fund and we believe that people can do it, or not a fund, a website and things like that.
0:17:29
I do help people in that way. I help people learn how to do this and just apply it to their life.
0:17:36
And then that’s kind of the whole thing.
0:17:40
I’ve been approached many times to do a managed active fund, to even have the sponsors in place for a hedge fund.
0:17:48
And that’s just not where I want to go with it right now, just because I think that will bring a lot more stress and pressure in my life.
0:17:58
And we all have to decide if the trade-off is worth that, you know, just from a standpoint of I like the way life sits right now.
0:18:08
I like doing my trades. I like helping the couple hundred people that we have on our website that come every week and do this as well.
0:18:16
And so for me, it’s hard to weigh those trade-offs.
0:18:22
But with a baby on the way, first baby on the way, it kind of is like, hey, it’s not the time.
0:18:29
I mean, I still have a sponsor who I’ll be in New York City next month to hold another meeting over this.
0:18:41
And I’ll be on the New York Stock Exchange trading floor and all of that stuff.
0:18:45
And it’s fun and it’s enticing and intriguing.
0:18:50
So maybe one day that’s in the cards because the reality is, is a lot of people don’t understand.
0:18:57
They may understand the mechanics of how this works, but they don’t understand how to apply it week in and week out and make it work.
0:19:05
Right. Because the reality is, is that it very much can work, but it’s like anything else.
0:19:11
People get greedy. People break the rules that you kind of have set for yourself in an attempt to do 2% a week or 3% a week. These numbers that really sound doable, but when you kind of run the math, you say, okay, it’s not normal to do 300% a year.
0:19:32
and to get 300% a year, you’re probably taking substantial risk. And I continue to think the
0:19:39
best risk adjacent way to get that is probably just buy and hold Bitcoin, right? It’s probably
0:19:44
just to do that. So our way beats the compound annual growth rate of the traditional assets,
0:19:51
S&P 500 and things like that. It’s a little bit up in the work scale, right? So it’s not set it
0:20:00
and forget it, but it is very much.
0:20:05
We do a little bit of work on Mondays and that’s it.
0:20:09
So my place becomes a ghost town Tuesday through Friday and the weekend.
0:20:15
We do everything on Mondays and then you just leave it alone.
0:20:18
So to add 15 to 30 minutes of work to your day on a Monday to take returns from 10% to
0:20:26
40 plus percent is well worth the trade-off in my opinion. And so people who have capital sitting
0:20:35
idle and are able to take this and slowly apply it, we think it’s a good fit for their lives. I
0:20:43
think it’s a good fit for their lives. And so we don’t want to push it on anybody, but I continue
0:20:49
to just try to share what we do and what we’ve done in the past and with the newfound Bitcoin
0:20:54
lens of just acquiring more Bitcoin. It’s really fascinating, Caleb. There’s so many things I want
0:21:02
to ask about. Again, I’m a bit stumped as to which way to go, but let’s do this. The strategy that
0:21:09
you’ve talked through is a strategy that’s worked in other markets and has been reapplied to Bitcoin,
0:21:16
which I love. It’s kind of like, oh, I went to Mexico and saw these incredible,
0:21:20
incredible tacos. I’m going to bring them to Australia. Oh, what a surprise. Everyone loves
0:21:24
them. You’re taking a product that has a market fit somewhere else and just reapplying it to a
0:21:31
new place. That’s awesome. One of the things that I think that the traditional investment market
0:21:37
underplays is counterparty risk. And so you go to a wealth manager and they give you a diversified
0:21:44
portfolio of stuff. And you’ve got to trust the wealth manager to make the right decisions.
0:21:49
They still get paid regardless of performance, their 1% fee per annum.
0:21:53
And you have no idea really what you own because it’s a bunch of stuff that you’re not familiar with.
0:22:00
And all of it requires trust that you’ll get your money back.
0:22:04
Now, the big thing with Bitcoin is obviously get your self-custody correct.
0:22:08
No one’s taking that shit from you.
0:22:10
And so I’ve become much, much, much more aware of counterparty risk.
0:22:15
And so what’s the risk of using iBit?
0:22:17
What’s the risk of using these brokerage accounts? I’d love to know how you think that through.
0:22:23
It’s obviously a trade-off you’re willing to make with a portion of your stack. Presumably,
0:22:28
over time, as I think this through, if I’m creating a yield on that process,
0:22:33
and I’m stacking more and more Bitcoin into self-custody, that counterparty risk naturally
0:22:38
becomes lower because your portfolio is not all attached to that kind of investment process.
0:22:45
So yeah, how do you think through counterparty risk in today’s world?
0:22:49
Totally. Yeah, totally understand. Yeah, it’s a real risk and one that should be re-evaluated
0:22:57
daily, I believe. So I think the biggest thing in the traditional markets, you have FDIC insurance,
0:23:06
right, in the States. And so your brokerages are generally insured up to 250K. I’m sure it’s
0:23:17
played out to where those bailouts have happened. But I try to look for good publicly traded brokers
0:23:26
or whatnot that have a clean balance sheet, right, that are taking care of themselves.
0:23:33
But it goes back to what you said is it’s not self-custody in a hardware wallet in which you have taken full control of your keys.
0:23:48
So there is the trade-off.
0:23:51
I think that in stages of fiat currencies, things can get messy and insurance is meaningless.
0:24:00
So it feels like we aren’t there yet. So I guess I say I still largely trust the institutions that I use simply because their balance sheets are clean, mostly clean, and they’re ran fairly responsibly.
0:24:19
That being said, there is still trust required. Right. And so as things degrade more and more, as the currencies continue to devalue and collapse and things like that, it’s something that eventually could become too risky to do.
0:24:39
And so it’s funny when I talk to my, I come from the traditional finance world.
0:24:43
When I talk to those people, it’s the exact opposite mindset, right?
0:24:49
Oh, there’s no insurance in Bitcoin.
0:24:51
There’s no, it’s, I got to take care of this myself.
0:24:54
What’s the customer service number?
0:24:57
You know, it’s just a completely different mindset.
0:24:59
And so I’d be lying if I didn’t say I still have some of the old traditional mindset of some of these institutions are safe for now from a standpoint.
0:25:14
But listen, fractional reserve banking, you know, I think any bank is in danger if enough people are riled up enough to try to go withdraw their money at once.
0:25:31
So there’s always those fears and those concerns.
0:25:34
And it’s why it’s why people hoard gold and they’re safe.
0:25:37
It’s why people have Bitcoin in a cold storage wallet, you know.
0:25:41
So for me, it’s one that’s constantly being reevaluated. And as you said, has gotten less and less risky as I’ve gotten more and more stats in a wallet and taking that risk off the table some to where while I wouldn’t want to go through it, it wouldn’t be the end of everything if it just woke up one day and it was gone.
0:26:02
So that will continue to be a thing because eventually the Bitcoin wallet will outweigh.
0:26:11
And so with each week that passes, it stabilizes more and more.
0:26:15
And so that’s kind of the way I’m looking at it.
0:26:17
And so, you know, 2026, we’re all hopeful will be a good year for Bitcoin.
0:26:23
And as the price goes up to that, even more sways at risk of just more of it being over here than over here.
0:26:32
And so right now that’s where I’m at. And so it helps to have a little bit of experience in both worlds, I feel, to understand self-custody, but to understand how to choose a broker that’s not sketchy or in financial ruin.
0:26:49
if i was to think about how i would look at a portfolio quote unquote or your net asset
0:26:56
statement is probably a better way of saying it um you know you want to be thinking about capital
0:27:01
growth you want to be thinking about capital protection and cash flow and then in in the past
0:27:08
it’d be like a fourth bucket which might be just precious metals you know your gold and it’s like
0:27:13
Okay, so Bitcoin’s pretty good at capital growth.
0:27:17
It’s got you covered there.
0:27:18
It’s actually pretty good at capital protection over a decent time horizon.
0:27:23
Cash flow, Bitcoin, no can do.
0:27:26
And it is essentially a precious metal.
0:27:29
So for me, that four-bucket net asset statement is really precious metals.
0:27:35
To me, I’m like, if you understand Bitcoin, why are you buying gold?
0:27:39
And that’s why the current gold price action is so interesting,
0:27:41
because it’s probably a better reflection of the fact
0:27:44
that most people just don’t get what Bitcoin is.
0:27:47
Yeah.
0:27:48
And I do subscribe to this idea of Bitcoin as a slingshot.
0:27:52
So at some point,
0:27:53
it’s just going to absolutely fly past that growth rate of gold.
0:27:57
I agree.
0:27:58
But where I’m going with this is like to generate cash flow,
0:28:03
you know, having cash flow is an important part
0:28:05
of this wealth strategy for anyone.
0:28:07
And so taking counterparty risk on
0:28:09
or any manner of risk that you might come up with,
0:28:11
well, it’s absolutely worth it in some scenarios.
0:28:14
So I’m not against that by any means.
0:28:16
And if anything, I’m like,
0:28:17
what a brilliant position to have built yourself, Caleb.
0:28:19
It’s like, okay, you’re slowly but surely adding
0:28:21
to that long-term capital growth, capital protection play
0:28:24
at the same time as generating cashflow
0:28:27
in an area where you have expertise.
0:28:29
And that is your edge.
0:28:31
And that’s what I’m always looking for as an investor.
0:28:33
It’s like, what’s someone’s edge?
0:28:34
I’m like, ah, what are you doing with your money?
0:28:37
So that phrase, like, ask a man what he owns,
0:28:39
not what he’s doing or not what he thinks.
0:28:41
It’s so much better.
0:28:43
It’s like just teach what you’re actually doing
0:28:44
and what is the result.
0:28:45
Oh, wow.
0:28:46
30, 40, 50% CAGR.
0:28:49
What a brilliant result to be getting.
0:28:51
What I love to do though Caleb is slightly cycle back to this idea of selling consulting and what i think is interesting is the further you get along this bitcoin journey the further
0:29:02
you start to question your time and so where did you get to with that so it just the trade-off
0:29:08
wasn’t worth it like selling your time for people you’re like actually i just i’d prefer just to do
0:29:13
my investing and not have to do that so just run me through how that felt at the time because i
0:29:17
I think it’s something that I’ve certainly got to myself.
0:29:20
I could sell consulting, but do I really want to have a calendar open to any old punter
0:29:25
to book a time?
0:29:26
I’ve got three tiny kids.
0:29:28
You boot yourself all this position of freedom and then you’re clogging it up again.
0:29:31
That didn’t make sense for me.
0:29:33
Yeah, it’s the same cycle that I went through.
0:29:36
Free time.
0:29:38
Maybe you booked that first consulting gig and it feels exciting.
0:29:41
You’re like, oh, okay, someone wants to hear what I have to say and they’re willing to
0:29:44
pay.
0:29:45
That’s really cool.
0:29:46
It’s really fascinating.
0:29:47
And so I went through this cycle.
0:29:50
I got too busy.
0:29:52
I raised my prices and I got too busy again and I raised my prices again.
0:29:57
And then I got to the point where I don’t want to say I was done raising prices, but I continued to charge what I felt was reasonable and made sense for my time.
0:30:17
but then just realized I don’t think I can charge what I feel my time is worth at this point.
0:30:22
And essentially getting to that point of, I don’t think there’s a dollar amount to make me do this for now.
0:30:28
And that’s not to say that I would never do it again.
0:30:32
You know, things always change.
0:30:34
And I feel like I go through seasons of really enjoying being social and pressing in the world.
0:30:45
And then I really enjoy disappearing into the shadows and just being in my home with my wife and just hanging out and living life and maximizing just what we’re doing.
0:31:00
So it just got to a point where it was no longer worth the tradeoff.
0:31:05
And then, too, you constantly come across, does this person value my time?
0:31:13
You know, if you’re 15 minutes late to a Zoom call, if you constantly cancel meetings, if you just, you know, various things like that, where it’s like eventually get to the point where it’s just like I’ve fired I’ve fired people that hired me.
0:31:31
You know, it’s just like, hey, listen, this is going to work.
0:31:35
And so for me, it’s all about the trade off has to be worth it.
0:31:38
And it’s time is very scarce. Right.
0:31:43
We’ve only got so much of it. And eventually I just said, I can’t sit in front of this computer screen for hours and hours a day all week long.
0:31:54
You know, I live in a national park. So like just outside these doors is world class whitewater and mountains and mountain bikes and all of this stuff.
0:32:04
And so that was just the lure for me. But the hunger to still build relationships and teach didn’t leave.
0:32:12
I just wanted it to be looked different.
0:32:15
And so the more scalable solution was to do something in mass and just publish and help
0:32:23
those who were more okay with maybe not as much consulting like instance, but just more
0:32:31
group and, and, and group oriented content.
0:32:35
And that’s kind of where we settled.
0:32:36
And it’s a very nice trade off because I can put a few hours in a week.
0:32:40
and now I put a lot more time in my research
0:32:44
and I enjoy the research side of the markets and what I do
0:32:49
but I’ve only got a few hours a week
0:32:52
and FaceTime with people and that’s nice.
0:32:56
It’s fascinating because it’s a trajectory that’s very common
0:33:00
and it’s really where the economics required
0:33:05
to understand what is going on come to the forefront
0:33:08
which is sound money.
0:33:10
You’re like, oh my God, how on earth have I been through 20 years of your dad teaching
0:33:18
you about business and thinking about money and figuring it all out?
0:33:21
I’ve said this many times before, I’ve highly trained in how to make money, but never asked
0:33:26
the question, what is money?
0:33:28
It’s like, what the fuck?
0:33:29
How has that happened?
0:33:31
But when you start digging into like, okay, well, sound money is this thing where it operates
0:33:36
completely differently to a central bank.
0:33:39
and gold is the best format of it thus far.
0:33:42
And now we’ve got this thing called Bitcoin
0:33:44
and all the different characteristics
0:33:45
of what makes a good money,
0:33:47
being portable or whatever.
0:33:49
And then the features of money,
0:33:51
store of value, unit of account,
0:33:54
medium of exchange.
0:33:55
Oh my God, this is so important.
0:33:57
How on earth has this been missing
0:33:58
from my kind of business education?
0:34:01
This is mental.
0:34:02
And the ultimate point being
0:34:03
is it’s about time preference.
0:34:05
And it’s about being able to bet on the future
0:34:08
with confidence in a way that you weren’t before.
0:34:11
And with that, of course, your daily action changes
0:34:16
and the cost of your time alters.
0:34:19
Because here we are now,
0:34:20
you’ve built this incredible position of expertise.
0:34:23
That’s your intellectual capital.
0:34:24
Your financial capital is getting stronger every day
0:34:26
because of how the expertise is deployed.
0:34:29
And it’s like, well, hang on.
0:34:30
I know that in the background,
0:34:32
Bitcoin is just going to keep crunching away
0:34:33
and purchasing power.
0:34:34
so why am I spending six hours a day on a video call selling my time when actually the time I’ve
0:34:40
already sold is going to get more valuable and so the whole thing shifts essentially so actually I
0:34:47
want to just be a dad or I’m going to go mountain biking or I’m going to I’m going to enjoy my life
0:34:52
and it’s like oh my god imagine the difference this makes at scale to human action like it’s
0:34:59
going to be so different in the not too far future. And I’ll caveat this with, you could run a fund
0:35:07
right now. You could be like, hey, Caleb, yeah, I’m a hedge fund manager. And this is my business.
0:35:12
And I want, you know, minimum ticket of 250 grand, I’m aiming for 35% a year, you know, boom,
0:35:18
off we go. I’m regulated, I’m insured, these are my, you know, main investors, blah, blah, blah.
0:35:23
And the ego is like, hell, yeah, I’m gonna be a hedge fund manager, right? It’s just it’s right
0:35:28
there you could take it but at what cost and the cost is a different calculation with sound money
0:35:36
behind you it is so and take it from there Caleb like some of that resonates surely
0:35:42
yeah so it’s crazy and and it’s as long as I’ve been a bit corner I feel like
0:35:47
you can never get to the bottom of the Bitcoin rabbit hole like it just no endless
0:35:51
but you know what just really really really clicked for me within the last month is we
0:36:00
we live in a debt-based society like globally really i mean it hits us in the states it hits
0:36:07
everywhere yeah it’s everywhere and so like the states is now 30 or 38 trillion dollars in debt
0:36:17
right? There is no. And apolitical, I really do stay apolitical because it doesn’t matter who’s
0:36:25
in office anywhere, right? One of the things that you should talk about is, oh, we’re going to cut
0:36:31
deficits or we’re going to get into a spending deficit and we’re going to start paying off the
0:36:39
debt, yada, yada, yada. But what really just resonated with me is they can’t do that because
0:36:46
in a debt-based society, every infrastructure that we have crumbles. It crumbles. So I don’t
0:36:57
know if you paid it. I started really digging into it. And did you know that the United States
0:37:02
government ran at a surplus in September, which is very, very, very rare. But what that means
0:37:09
is that the United States government is the biggest depositor of liquidity into the United
0:37:17
States economy by spending. Not only that, we had a government shutdown in October,
0:37:24
which led the Treasury General’s account being frozen. And that shutdown lasted throughout
0:37:30
October and into November. So what we saw were two months, two months of basically the liquidity
0:37:39
being shut off. And it coincides right with Bitcoin going from $125 to $80. And so I really
0:37:49
believe when it just kind of started to click that we are too far gone, like the debt can’t be stopped
0:37:57
because if it stops, everything implodes, right? It’s too far gone, in my opinion. And so
0:38:05
without huge, huge, huge intervention, right? And I know as a Bitcoiner, I think Bitcoin could be
0:38:14
part of that intervention and a large driver, but that’s another topic. So for me, learning that
0:38:20
and says every fiat currency eventually and always has just imploded, right? Some of it takes decades,
0:38:30
Sometimes it takes hundreds of years for a currency to run its full course, but they always tend to be inflated to death.
0:38:37
And for the first time in the history of the world, and thankful that we live in the age of the Internet where this is possible to exist, we have a money that is hard.
0:38:52
Hard capped, can’t be inflated beyond its 21 million hard cap.
0:38:59
And the reality is it’s actually a lot less than that likely if you really factor in lost coins from the early days and things like that.
0:39:08
Right. So we have we have a hard money for the first time.
0:39:13
So if you believe that fiat currencies are are always inflating and and inflating into oblivion until they’re gone and the next one spins up and we reset and we do this.
0:39:24
it makes sense why would you really like you can just store in bitcoin and allow that inflation to
0:39:33
at least work for you right because if you’ve held your money in bitcoin over the last five years
0:39:40
seven years ten years your purchasing power just keeps going up and so like i knew that but then
0:39:47
when i started like i knew the bitcoin side of it but when i started to dig into the other side
0:39:51
It was like, oh, these governments have to have debt, like debt and liquidity are the grease that keep the wheels moving at this point.
0:40:00
And so that was a big revelation for me.
0:40:03
And that’s why it’s just like.
0:40:05
And this is like to like copy paste this on the back of the conversation we were having 10, 15 minutes ago.
0:40:11
It’s like if we could just get that and maybe Bitcoin isn’t meant to be a cash flow generator, right?
0:40:17
Maybe that’s not where it goes.
0:40:19
But it’s like, if I could just generate cashflow there, then it’s, it’s the perfect thing.
0:40:26
And I don’t want that done in a reckless or weird way.
0:40:30
So I don’t know what the solution is there or if there is one, but, uh, if, if that’s
0:40:38
resolved, it’s truly the perfect invention.
0:40:42
I mean, it’s already the best invention and because mentally it’s hard to sell, like the
0:40:49
think about, oh, I’ll just sell off small slices of Bitcoin to live. Maybe, maybe eventually you
0:40:55
get there. But for me mentally, I’m like, oh, I can’t sell my Bitcoin. Like this is going to be
0:40:58
worth more in two years, four years, six years, eight years. So I need cashflow. Right. So like
0:41:02
to put that full circle, it’s just like, everything is endlessly being debased. We finally, we live in
0:41:11
the time in humanity where we have a life raft and that’s a beautiful thing. So that just clicked
0:41:18
for me and it just says like, I don’t have, like I can opt out. I can opt out of needing to put 60,
0:41:26
80 hours in because I can make my own way and saving money that’s going to increase in purchasing
0:41:34
power. And so I don’t have to sacrifice my twenties, thirties, forties to have enough
0:41:41
purchasing power in my 50s and 60s. I just save humbly in Bitcoin and I can live for the now and
0:41:50
the future because Bitcoin’s doing the heavy lifting of the future. I don’t have to put in 80
0:41:54
hours. I don’t have to put in all these crazy things that people do these days. So to me,
0:42:00
it’s just a beautiful time to be alive and a beautiful invention to be thriving in the midst
0:42:04
of. Yeah, we’re extraordinarily lucky to have pieced together the pieces required to see value
0:42:11
where others don’t and it’s still the case in my mind that we’re just we’re so much earlier than
0:42:17
what we realize yeah um most most people have no idea what holding a majority of your net wealth in
0:42:25
a multi-sig with geographically dispersed keys and purchasing power just pumping away in the
0:42:30
background after a large reallocation no one else that feels like um i’m intrigued caleb so got maybe
0:42:37
15 minutes or so left, there’s two areas I want to get into and I’ll save the second
0:42:42
for a minute. But in terms of your options strategy, so you mentioned you want a probability
0:42:47
of 75 to 85%, roughly, I think it was what you said. So you’re looking at forward pricing
0:42:53
for what duration in advance?
0:42:57
We should do weekly.
0:42:58
Okay. Perfect. Okay. And so when you look at the curve for these prices over the next
0:43:04
six to 12 months.
0:43:06
I think the backdrop of what you just highlighted is really fascinating in terms of price action
0:43:10
this year.
0:43:11
So first of all, the four-year cycle is under very, very, very serious stress right now
0:43:16
slash broken given the year figure 1st of Jan 2026 was down It like ah okay well that annual period on our calendar wasn green That broken the four cycle Perhaps that true
0:43:31
But the biggest buyer in the market, in the US specifically, was the government.
0:43:38
And for whatever reason, they went on holiday for a bit.
0:43:41
And equally, they ran a surplus for a month.
0:43:44
And it’s like, okay, well, that’s massive volume that just wasn’t there.
0:43:49
and the price did pull back, absolutely.
0:43:52
But when that machine kicks back into life,
0:43:55
no one’s stopping it, as you say.
0:43:58
And so what are we looking at then
0:43:59
over the next six to 12 months
0:44:01
from a kind of price action perspective, you think?
0:44:03
And how are you pricing your options over that time?
0:44:08
Yeah, I love it.
0:44:08
And I’ll give you my answers
0:44:11
because I’m a hobbyist macro economy enthusiast.
0:44:17
I give you my two cents on that. I think that what Bitcoin did in a quantitative tightening environment, in a high rate environment, is very impressive. And so the four year cycle had us in the mindset that, and I’ll be the first to raise my hand and say I was following the four year cycles, right? Like you just kind of follow it.
0:44:42
But the four-year cycle had us in the mindset that 2025 would be a moon year and that things would be up and up. And so when you really peel back the macroeconomics of it is really coincided with large times of printing, right? Large times of money printing and just when the economy is doing some funny things.
0:45:08
So what we’ve already seen, early December quantitative tightening came to an end.
0:45:14
The Federal Reserve is not shrinking its balance sheet anymore.
0:45:18
And that by default is bullish.
0:45:21
And then we are already seeing not direct quantitative easing, but some pseudo quantitative easing going on in the markets.
0:45:31
So the Fed’s already starting to increase things.
0:45:35
we saw all the liquidity got pumped in the market 2020. They started draining that liquidity out of
0:45:42
reverse repo markets in 2022. So we’ve been in a three-year drain of just getting the liquidity,
0:45:48
the excess liquidity out. And so the way Bitcoin held in those environments, well, now we’re going
0:45:54
into QE. We’re going into, at least as far as the states go, there’s already been announced a
0:46:03
stimulus and it’s a midterm election year, they’re going to send people money. And that’s
0:46:08
pumping liquidity in the most direct way possible is just getting liquidity in the hands of citizens
0:46:14
and it goes down. Now, I’m not saying I agree with it, but I’m just saying that it is what it is and
0:46:18
that’s what’s going on. So we have QE beginning in 2026. Fed’s going to be expanding its balance
0:46:24
sheet. They’re getting money into the hands of the people, right? And then through stimulus and
0:46:32
things like that. And then you have lowering rates. We lowered rates three times in Q4.
0:46:40
Now they’re talking like we may pause lowering rates for a bit, but regardless, 2026 will see
0:46:49
lower rates. So when we decrease the cost of capital, the appetite tomorrow and increase
0:46:55
liquidity into offensive investments and assets, the appetite grows. So I really think what we have
0:47:02
coming is just liquidity and injection beyond what we’ll realize. And this could age horribly,
0:47:10
and I’ll raise my hand if it does. But what I see coming is just quantitative easing,
0:47:16
lower rate environments, stimulus injections, and all of these things that are just going to
0:47:23
pump liquidity back into the market that got drained of liquidity. And so I think Bitcoin is
0:47:29
the barometer. I think it feels those things in the most raw and real way, right? It’s the smoke
0:47:37
alarm when things are bad, but it’s going to be the fastest horse when things are good, right?
0:47:43
So I’m not for throwing price predictions out there because I don’t know how crazy it could get
0:47:48
or how mild it can be.
0:47:50
But I think there is a huge, huge influx of liquidity coming into the system.
0:47:56
And I think it’ll start slow.
0:47:58
I think it’ll pick up because it is an election year in the States and they’re going to manipulate
0:48:05
the feel-good feeling to come right around the time where people start to wonder who
0:48:11
they’re going to cast their vote for and what party and things like that.
0:48:15
And so all of that being said, that circles back into where we continue to have an approach with our options and our options selling.
0:48:26
We always default to because the worst thing that can happen with my strategy is you own shares of something, right?
0:48:35
And the shares of that something in dollar prices can drop.
0:48:38
So if you buy something at $100 and it drops to $50, well, then that’s pretty painful because your base capital you invested and just got cut in half.
0:48:46
So the biggest thing you can do is avoid that, right?
0:48:51
That’s what we don’t want to do.
0:48:53
So that’s why strategic selection of positions is so important is because selecting positions that are going, that are poised to go up in value is a really good thing.
0:49:08
So for us in the 2026, we continue to look for pockets of value because I bid as a large portion of my strategy, but I will still sell options on traditional positions, equities in the market if the yield is there that I like and the risk reward is there.
0:49:30
So for me, the risk reward assessment is, can I take a position at a price that I think is near its price for?
0:49:39
And that’s based on fundamental value investing.
0:49:42
Like before the Bitcoin days, I was a Warren Buffett, Benjamin Graham value guy.
0:49:48
So I always want to, you know, if I’m going to buy something, it has to be cheap or undervalued or at least fairly valued.
0:49:57
So it’s hard for me to go touch these stocks that are overvalued and overcooked and the AI names and things like that.
0:50:04
So for us, it comes back to where can we generate this yield that isn’t going to have a 20, 30, 40, 50% drop.
0:50:11
And then when we generate that yield, we flow it into Bitcoin.
0:50:15
So I’m very bullish on 2026 simply because of the macro backdrop.
0:50:22
And I think the macro backdrop is going to push a lot of assets up and, you know, be it this arbitrary turn of the calendar.
0:50:33
And but Bitcoin is already starting to come back to life a little bit today.
0:50:38
It’s starting to wake up.
0:50:41
Bitcoin related assets are starting to wake up because they’ve endured some pain.
0:50:46
I mean, if you look at the Bitcoin related positions, they have endured some pain.
0:50:54
So when they go, they can go quick.
0:50:56
So we’re kind of positioning for that.
0:50:58
We believe that that is what’s on the horizon in 2026.
0:51:03
That’s kind of what we’re preparing for and our outlook on things.
0:51:08
You know, if my macro is wrong, I’ll have you edit this out.
0:51:14
That’s the bit we have to keep in.
0:51:15
The truth is, anyone out there that gives you a price and a date, they’re wrong.
0:51:22
Because no one fucking knows.
0:51:24
They don’t.
0:51:25
The key is being in a position where you can be okay either way.
0:51:33
And that’s not so easy to achieve in some ways, but it needs to be part of your decision-making process before you even get there.
0:51:40
Okay, Caleb, as much as I am loving learning about the specifics of all of this,
0:51:45
there’s one area that I want to touch on.
0:51:46
We’ve got another five minutes or so before I close it up.
0:51:49
And that is fatherhood, which for you is just around the corner.
0:51:54
You know, having children is the ultimate investment.
0:51:56
And I would describe it as humanistic capital.
0:51:59
You know, I look at three key areas, intellectual, humanistic, and financial.
0:52:04
And they’re all different forms of capital.
0:52:06
And, you know, you’ll meet people who have done extraordinarily well
0:52:09
at financial capital, but they’ve been divorced a number of times
0:52:12
and their kids hate them.
0:52:14
So, well, that’s clearly not the right balance to try and hit.
0:52:19
And equal insight that I really love is that without humanistic and intellectual capital together, you’ll never drive financial gains over generations.
0:52:28
So without having kids, then what’s the point of the work you’re doing today in terms of keeping it?
0:52:33
So, you know, nervous, pumped.
0:52:36
What was the reason to step into parenthood?
0:52:40
Yeah, I would say all of the above.
0:52:42
nervous pumped um yeah it’s just i don’t know it’s and part of it is um
0:52:50
life is designed by default to keep us busy and stimulated and numb almost to living a real full
0:53:00
life and so bitcoin to help help me slow down and i hate to keep going back to bitcoin but the
0:53:06
no no no dude it’s the low it’s the key part and so the low time preference um you know i’m 33.
0:53:15
i’m not old yet but i’m not in my you know i’m not having i’m not 20 anymore i’m not 22.
0:53:22
so my wife is younger than i and so we finally just felt the time was right it’s time to slow
0:53:30
down. We have the infrastructure to be present with our kids in a full totality, you know, 24-7.
0:53:39
So the time was right. And so we’re excited. And just, you know, we live in the country.
0:53:49
You know, I’m not near a city. I’m in the middle of nowhere.
0:53:53
I have land, you know, we’re, we’re excited to raise them in slow motion, so to speak, you know,
0:54:03
in a, in a place that is still like stepping back into the 1990s or something, you know, it’s,
0:54:11
it’s slow. It’s the, you know, it’s just a, and we’re very excited about that. So I,
0:54:17
I have no idea what to expect. I do not come from a large family. My wife comes from a very large
0:54:24
family. So I’m going to, you know, it’s, we, we’re excited to, to learn. We don’t know what
0:54:32
we’re having. We’re, we’re two months out or less than two months now. And we felt it was super low
0:54:40
time preference to just not find out. Like, let’s have that joy in the moment. Because one of our
0:54:46
things myself and my wife that we’re constantly on is is it seems like people can’t wait on things
0:54:52
anymore there’s no waiting there’s no delayed gratitude there’s no it’s it’s a now culture
0:54:59
thanks to internet and things like this and so we decided let’s wait let’s find out in the moment
0:55:06
when it’s here with us so very very nervous but very excited yeah it’s cool
0:55:14
if you’re if you had to guess now boy or girl i’ve said girl all along i’ve always said girl
0:55:22
but my wife says boy so it’s hard to go to some others i mean if if this is anecdotal but in my
0:55:31
experience my wife and i got it wrong every time i thought the first one was a boy and it was a girl
0:55:36
i thought the second one was a boy it was a girl and the third one was like well i’m just gonna be
0:55:40
that guy that has three girls and it was a boy so we were wrong every single time um and how’s the
0:55:46
moment where like you start having to buy stuff to like clothes arrive or like there’s like a pram
0:55:52
or stroller as you’d call it you have to build the cot you’re like oh my god look there’s like a
0:55:57
little room like what the hell yeah it’s crazy right we just had um like the shower the baby
0:56:03
shower sure and so we are overwhelmed with stuff that was saturday so it’s today’s it’s tuesday at
0:56:12
my time right now um and so i just have like every corner of my house just has boxes and stuff right
0:56:20
now you know we’re trying to distill like what do we get on a symbol right now what do we like
0:56:25
like a stroller um maybe we wait on that maybe we wait on we’re just trying to figure it out man
0:56:31
we’re we’re uh excited and trying to learn and we’re just trying to be responsible people that
0:56:38
they raise our our our first child with strong morals um and what we believe and and just
0:56:46
trying to raise them the right way right and what is that that’s what we’re trying to do
0:56:52
well it’s the ultimate process of kind of learn by doing so yeah awesome caleb what an amazing uh
0:56:59
hour we spent talking. Thank you so much for your time. Thank you for teaching us what you have and
0:57:03
wishing you the very, very best of luck as you move into the next phase of your life. And what
0:57:08
a great bit of progress so far. Thank you. Thank you, Jake, for the time. Thank you for putting
0:57:14
this all together. And yeah, I enjoyed it a ton, man. Appreciate you. Final question is,
0:57:19
if anyone wants to reach out and get in touch, what’s the best way to do that?
0:57:22
yeah it’s a great question you can always find me on Noster I am not Noster exclusive yet but
0:57:31
that’s where I like to be I’m Caleb Gregory 304 on there but I’m at the same handle on X which I
0:57:40
don’t really use but you know I’ll pop in once a week so that’s where I’m at that’s where I post
0:57:46
my thoughts and appreciate it, man.
0:57:49
Awesome.
0:57:49
Thank you,