Watch the full video of our conversation on the Spread Great Ideas YouTube channel.

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Full Transcript of Our Conversation

Introduction to Ryan Coisson: Digital Business, Content Marketing, and Finance

00:00.00 – Brian David Crane

Hey folks, please welcome to the show Ryan Coisson, I hope I’m pronouncing your last name right? You’re going to have to correct me if I’m not known him for more than 10 years. He’s a digital business owner, content marketer, an outdoor adventurer and a finance whiz. He’s created high-level processes including planning and building very specifically. And I mean very very specific actionable steps to achieve the goals around those plans and he’s just a nice guy. That’s why he agreed to join me today. We spent a ski season in Whistler Canada living together as part of a shared chalet filled with entrepreneurs. Since that time we have our paths kind of like crossing, they diverge, they cross again.

I asked him to come on the show to talk about perfect biz talk about some of the different projects. He’s involved in ecom master’s online option. Ah, we’re going to start with finance I think because that’s my most recent touch point with Ryan which was um. Very quick backstory: I had quite a bit in bitcoin that plummeted in the 2020 run into lockdowns to Covid and Ryan reached out and said something very sage which was basically that to keep cash like that in bonds. Because they go down less than the rest of the market and then be able to sell those bonds and be able to buy stuff at a discount is that a fair fair summary of what she said.

01:22.82 – Ryan Coisson

Yeah I think so. I mean to to just add a little tidbit to that I think anytime somebody is thinking about financial decisions right? It always needs to be part of some greater plan and I think that particularly.

01:29.34 – Brian David Crane

Please.

01:40.80 – Ryan Coisson

For folks like us in the entrepreneur space. This is somewhat counterintuitive because we’re used to stepping up to the plate and needing to hit a home run to run a successful business to build our team to manage payroll. All of these things and for folks like us who’ve been in this sort of career path for. Years or decades and I got my first start in 2003 and if you have that sort of personality you have the tendency to want to take risks all the time and the risks that you believe you’re taking in your business are often more calculated because you control. Human capital. There’s a lot of things under your own power when it comes to investing in the markets. Brian, one of the tricky things entrepreneurs in particular or folks who get enamored by an asset class and we had just come out of a really strong bull run within the cryptocurrency space. And there’s a lot of arguments to be said for the validity of some of that bull run during that period of time but one of the things to think about is everyone looks smart. During the bull market right? Understanding market rotation, understanding diversification and and overall how to manage an asset portfolio that allows you to most importantly, as an entrepreneur sleep well at night so that you can maintain.

The Importance of Managing Risk and Focusing on Earning Power

03:06.30 – Ryan Coisson

But in my opinion the most important thing is your earning power. We believe, kind of in my philosophy of investing is if you’re especially if you’re an entrepreneur focus your business. That’s you’re taking so much risk in your business already focusing your investment portfolio on. Doing things that are far less risky and those that are risky may be in the cryptocurrency space and we can define risky as volatile. In this case, make sure you have a plan of how you’ll potentially manage that right? So we can go into a whole rabbit hole here on this and I think that. Again, the overarching premise that I would always encourage folks is where you get your financial cues from many people it could be their parents. It could be friends. It could be extended family members. Maybe a book or 2 that they’ve read could even be a financial advisor right.

Financial Advisors can be fantastic. They can be expensive if you do go that route you want to make sure you find somebody with a fiduciary responsibility. Not just like a general salesperson, but have an actual plan where you’re getting those financial cues from and a trajectory of like, where am I trying to go. And said period of time I think one of the traps that you had fallen into is this exuberance for the asset class and kind of on the other side. What might be driving that currency debasement? Greater economic troubles all of these sort of things. And a lot of that is true, but sometimes the story you’re following is going to have a lot of rocky roads in it and if you can’t survive those bumps especially, kind of between the ears which is the most important thing as an investor and trader especially it’s going to be very difficult for you to operate your business successfully as well.

05:03.23 – Brian David Crane

Super well said. So there’s 2 threads in that one is that like in my business or in your business, I have a modicum of control right? I have the ability to fire hire. Deploy capital change strategies to x y and z as opposed to being a passive investor in something like bitcoin or a DeFi protocol, or whatnot where I just don’t really have any… I’m purely like a spectator or retail in that sense right?

Understanding Market Dynamics: Short-Term Sentiment vs. Long-Term Fundamentals

05:32.26 – Ryan Coisson

Yeah, and again, think about what you know in the long term. What’s driving markets often is fundamentals. You know, corporate earnings, these sorts of things. The market is going to be a forward pricing mechanism. So it’s pricing things out well into the future often. 12 – 18 months, there’s going to be gaps within the market that are undervalued overvalued type situations, but in the short term right often. What’s really driving the market is expectation sentiment right? If there is a big belief that, said statement from the fed chair, or something is going to weigh on the economy even more you’ll see the market move dramatically, When we’ve had different presidencies. We’ve seen a tweet cause the market to completely shift in relation to tariffs in China. Emotion that sort of overall sentiment fear greed sort of drives the market in the short term but in the long term, think more fundamentals, corporate earnings and things like that.

So when you have an asset class that doesn’t have corporate earnings, doesn’t have any sort of these general fundamentals and you’re betting on this overarching storyline and really.. In my opinion, the main storyline for a cryptocurrency like Bitcoin which was in reference to, is that this is one of adoption right? So the more adoption there is to that asset class, the valuer and stronger that asset class sort of becomes during that period of time.
There was generally negative sentiment about the asset class and the validity as the story has continued to develop now a couple years later we see ETFs being approved for that asset class.

We see, kind of shaking out, continued shaking out of bad actors within that space. We see continued development of ah institutional development or institutional capital. Being deployed to there where you have, pension up. There’s a pension fund recently that came out and said that they had deployed 100 million dollars into the Blackrock Bitcoin ETF right? That adds a ton of validity to that particular space and with that adoption. One of the things, as someone who believes that category of investment is an asymmetric bet. I’m not going to bet against wall street especially when it comes to wall street being motivated to make money off of fees and now they have a very very easy way for them to make money off the fees, which is managing your money through the ETF.

Eventually, there will be other ways as well. But when you’ve got folks like you know Larry Fink behind Black Rock driving forward I think that that continued adoption curve is going to just accelerate.

Asset Allocation Strategies: Balancing Business Profits and Investment Portfolios

08:28.62 – Brian David Crane

Interesting. Okay, so when you think about your own asset allocation, let’s assume you have $100 and you own a business and..

08:30.47 – Ryan Coisson

Motion.

08:44.94 – Brian David Crane

Yeah, you have a hundred dollars in savings and that business is profitable, so the next month you’re going to have one hundred and one dollar a month, after that you have a hundred and two like what do you do with that hundred dollars

08:54.95 – Ryan Coisson

Yeah, so I think from my investing standpoint, my overall thesis is I’m playing for really 2 things: 1) Winning the game to me looks like creating what I would call an income engine. So a portfolio, generating income for me now I want that income to do a few things. One I want it to be continually growing so each year I want that income to be growing. 2) I want it to be safe and stable right? I don’t want to fall into the trap of that. Income investors broadly speaking fall into which is yield chasing and so they’re going to go after high current yield versus sort of maybe safety or the overall growth of that yield other way.

I am saying that is dividend growth and then I want that overall income. To be sort of diversified across different sectors which kind of falls into that stability category. But then lastly, what this really does for me Brian is so if your parents or my parents went to a financial advisor now or maybe when they were our age, they’re going to be given information. That’s okay, let’s you know, build to do this portfolio. What are your end goals and objectives? How much money do you need? Let’s orchestrate this so that we’ve got X pile of money like Scrooge Mcduck and now you’re living in your retirement. Hopefully your home is paid off.

And now you can sell some shares of your Coca-cola or whatever stocks or bonds and live off that every month and then all you need to do is account for inflation. So every year take a little bit more off and hopefully you don’t outlive your pile of money right? This is. Broadly called the 4% rule, but this has just sort of been kind of the thesis for many people to me. Yeah.

Dividend Investing and Income-Generating Portfolios for Financial Stability

10:47.16 – Brian David Crane

Sorry, but in that scenario that person is selling their shares. They’re selling Coca-cola. Yeah okay, go ahead.

10:51.82 – Ryan Coisson

Correct. Yeah, so the problem with this thesis is that the number 1 fear of retirees is to run out of money right? And if you think from a mental standpoint, if that is the number one fear, every month or every quarter or every year however you’re doing it, you’re selling and sort of killing off a little bit of the golden goose now generally speaking as long as there’s enough time in the market and the economy continues to move up, this has been okay. Vanguard published a study a couple years ago saying that the 4% rule needed to be addressed because they believed that over the next 10 years, the returns would be far less than the past 10 years due to inflation and other things. They are quoting out a 2 % return on an annual basis which.

11:43.66 – Brian David Crane

So..

11:48.38 – Ryan Coisson

Obviously doesn’t work in that scenario. But for me, it’s more of a mental side of the equation. So rather I just sort of do the opposite of conventional wisdom here which is in my opinion often. The best thing to do and so my strategy is that, I want to create a basket of investments. This is specifically in the portion of my income portfolio and we can kind of talk about other asset allocations there as well. But I want to create this basket of investments that is continuing to grow over time where I don’t value the actual. Dollar figure of the total portfolio as much as I value the safety, the security and the growth of the current income that I’m receiving right? if I’m getting a 6% overall yield on my portfolio.

12:37.00 – Brian David Crane

Um, yes, this.

12:43.42 – Ryan Coisson

For example, how much does that grow by next year? It’s not uncommon that you could have your entire portfolio grow 5% or 10%. The little pay raises as I’d like to call them. The folks over at Coca-Cola are great people. They work really hard on my behalf. They raise their dividend. They’re giving me a little pay raise and I appreciate that right? So that’s how I kind of think about that and so over time, that maybe starts off as a trickle but then over time that becomes bigger and bigger now. Talk before about sort of this yield trap. Right? And what is a yield trap because I think that this is something when someone hears income investors they often think well I want more income right now right? which it could be valuable right? But in reality what we want to think about is I don’t want to buy some company that’s paying me a 10% yield today, unless maybe I really need that income at this very moment.

I’m in my 70s or something but for someone my age I care a lot more about one if they pay a super high yield and it’s been inconsistent. It has a far greater likelihood of going away or just being completely cut altogether. That’s not how I want to deploy my capital. I want safe, secure, strong companies well diversified and they meet very specific criteria for me. I’m not looking just for that yield because I’m younger. I care way more about also sharing price appreciation. So the growth of the actual stock and then the growth of the dividend. So an example would be Broadcom right? Broadcom we’ll call it in the semiconductor space. They had been around for a long time. When I first started getting involved with Broadcom. The yield was over 5 you know the share price in the last five years or so has gone up over 100%. The yield has come down but the growth of the actual yield. The growth of the actual stock has been tremendous. Do the same thing with companies like Visa where the current yields less than one.

But if you look at when I was buying or getting positioned into that the yield was much higher, but the growth of the dividend yield for Visa is growing at over 10% per year at the current moment. These types of things are really important to me because, now flip the situation and say I’m 70 years old and I’m wanting to retire and I have a pension or something or social security. But now instead of needing to sell shares, have a growing income stream that grows every single year. I can use as much of that income stream as I want or I can reinvest parts of that income stream. I have dividends taxed currently preferentially so that’s a strong benefit as well.

But now if I live for 5 years or 20 years it doesn’t necessarily matter right? I’m not living in fear of running out of money, rather I could pass that portfolio on to my heirs if I wanted to so it really puts you in a stronger position. Financial position in my opinion and then from the mental side of things. You’re not kind of living in this place of just fear, uncertainty, worry. All things that are going to make those golden years far less. Beneficial for you, your family, your grandchildren whatever it might be.

Strategies for Identifying and Investing in Dividend Growth Stocks

16:23.71 – Brian David Crane

Yeah, so the part on Broadcom and Visa, I think is super interesting because when you’re looking at Broadcom and I’m trying to talk linear linearly you identify it on day one you buy it. Let’s say the share is $10 at that point the yield is. 4% on the $10 share price I don’t know what it was. But for example and you’re deploying capital into that stock or into a Visa with the kind of I would say like 2 levers. You got one lever which is right now, I think that they like the total addressable market or the value. The business is going to go up so therefore the share price is going to go up or maybe and or I believe that the yield is sustainable at its current level right? Like it’s kind of one of the two or maybe both right?

Maybe the sweet spot is, both are that you think the yield is sustainable at its current level. They got a motor around the business like a Visa and you think that the total addressable market is going to get bigger more people get credit cards. Credit card usage proliferates. Whatnot is that kind of.. that did my understanding correctly.

17:37.65 – Ryan Coisson

Yeah, so I think there’s a couple things here right? What do you think about it? First off, you know a common thing that folks hear about is if you don’t know where to invest or you’re an amateur investor, invest in an index. You’ll hear folks like Warren Buffett say that all the time that is incredibly valid. Right? And that is a very strong strategy for someone who’s a very amateur type investor now you can invest in indexes that are the S and P which is generally what a guy like Warren Buffett mentions you can invest in indexes that invest in overall income investments growth, stocks that pay dividends or stuff like that dividend growth stocks. But one of the things that a lot of people don’t know Brian is that there’s a drastic difference if you look at the results of just the growth of the S and P or the
S and P with dividends being reinvested.

Okay and I say that because the last time I pulled up the actual stat. It was something like 40% of the returns in the
S and P were based on dividends being reinvested and that’s significant right? So one of the things that I think people sort of get caught up in, and this is part of to your question is that well, I’m doing it for this? Am I doing it for that? And they think it’s sort of like this either or type situation. The way that I think about it is I have sort of criteria. I want to buy these types of companies and these types of companies I believe are strong companies but I want to buy them generally speaking when they’re out of favor right? So to go back to…

19:24.26 – Ryan Coisson

2020 2021 right? We had this big crazy market pullback and change and you saw your cryptocurrency portfolio drop where you thought things would be safe and secure. We saw asset classes like gold. We saw I mean 2022 was the worst year for bonds since I think 1929 right? So we saw a lot of crazy things. But in 2022 for example, Exxon was up 80% but when it was really beaten down I was buying shares. And people were worried. I mean Covid lockdowns. What’s gas prices? What’s going to happen to oil? You know all of these things would be tempered back but in my mind I’m looking at a company that has massive amounts of cash right? I see a company that.

20:03.60 – Brian David Crane

Or used to drive anywhere.

20:13.96 – Ryan Coisson

Has consistently paid dividends for years and years, whose raised dividends who I believe is again a strong company will come out of this. You look at that and compare that to something like Zoom which during that time initial sentiment was right. What’s driving the market that enthusiasm for that stock drove prices way up and then way down right the same with the peloton right? You saw Peloton shares dramatically hard last time I saw peloton was below four bucks a share and so it had this huge fall from grades now for me by buying that stability i’m. Getting a lot of different things I’m also getting exposure to companies that I would call quote unquote like a monopoly. You know, um, you look at energy companies or utility companies where they have these agreements with the state or depending where we’re in the city or something like that.

And it’s basically a monopoly right? People aren’t going to stop paying utilities and in those types of situations we can look at well how much does a company pay us part of that dividend right? if they’re paying us 4%. What’s that there? Current payout ratio and there’s a lot of things that you know help us understand. Is this sustainable? Is this something that’s going to put the company at extreme risk and obviously something in the consumer discretionary category is likely going to need to pay you less? Then something in the utility category right? I think that over the last while some energy companies and utility companies had been really beaten up, because if you think about that industry they take on tons of debt.

Right? to go for their business. That’s a natural practice within that business and so if interest rates are super high is that business going to be thriving during that period probably not right? But if you believe in specific sectors of that space or maybe even want to just buy an ETF.

22:11.55 – Brian David Crane

Where is it?

22:20.48 – Ryan Coisson

While the interest rates are high. You’re going to likely get better pricing right? So you deploy capital at what I believe are bargain prices of really strong companies and then as things start to turn favor right? There’s a saying, I don’t know exactly where I heard it but and this is I apply this to an income investor. It’s little by little a bird builds his nest right? and so it’s little by little over time I’m continuing to build this quote next to this basket of companies. And within that portfolio again. There’s positions that are more designed for growth and there’s more that are designed for income. There’s a balance there but in the end I still have that strong directive that trajectory and financial queue to this is what I’m going for. Right? And I’m not trying to time the market I’m not trying to be smarter than the market which is another trap that especially us entrepreneurs fall into.

Well I don’t want to buy now because the market’s going to go lower or I don’t want to buy now because look at what’s going on globally economically. Right? Well, all those things are still happening. The markets hit all time highs yesterday right? So if you think you’re going to be smarter. We got to realize it again. This is a forward pricing mechanism right? So while all of that can be the case if you focus on being in the market right?

Just like Warren Buffett, right he did. He’s more of a buy and hold kind of forever type person but he does sell and he’s got over 20% of his portfolio in cash at the moment because of those high rates. We can get a great yield on our money and wait for good bargains and opportunities. So that all kinds of ties together.

24:12.68 – Brian David Crane

Makes sense. What are you doing? Or let’s say this way, what are you recommending? So you talked about utilities. You talked about energy. Are you changing? Are you changing sectors?

24:13.70 – Ryan Coisson

That makes sense.

24:32.26 – Brian David Crane

Like you know Buffett is famous for he just makes maybe like I don’t know 3 or 4 buys a year. Maybe that’s even too high, like how often you are making, you opening up a position in a new company or shutting down a position. I don’t think you should ever shut down a position in an existing company like how much you are meddling with your portfolio In this case.

Portfolio Management: How Often Should You Adjust Your Investments?

24:57.20 – Ryan Coisson

Yeah, it’s not that much right? So here’s the thing. So first I’m still young. I’m in my late thirties and so I’m consistently investing every month right? This isn’t just like my retirement account type situation. As an entrepreneur I have a retirement account that, through my business, I can put in a significant amount of money right? That type of investing is different right?

25:20.98 – Brian David Crane

Profitable business. Yeah, a set by array.

25:33.41 – Ryan Coisson

This is also an important point that we should have. I should have mentioned before and something for people to really think about the type of investing you do within specific accounts matters right? If you have a Roth IRA or you’re a backdoor Roth IRA, and that money is going to come out tax-free when you’re retired, the focus I’m going to have in there isn’t necessarily going to be income. It’s more going to be growth oriented because I’ve got a long period of time and I want to build that pile of money as big as possible because when I take it out. It’s going to be tax-free. I can then redeploy that to generate income if I want at a preferred tax rate right rather than just spend it if I’ve got money in a taxable brokerage account.

I need to understand that if I invest in say cover calls or. A covered call fund which could be popular for income investors. That’s generally going to be taxed at ordinary income if I’m in a high earning season right? like if I’m a business owner and I’m being taxed at the highest bracket that often may not make the most sense. During that period of time, so you have to sort of I guess think about that first and foremost right? I think that’s super important and then from the position standpoint. It’s been incredibly rare that I’ve ever terminated a position.

27:00.77 – Ryan Coisson

As an income investor. The primary reason I would do that is the health of the company is poor and they no longer could pay say dividends so we saw yesterday not invested in this company I had previously been invested in. Yeah years ago but 3m had a drastic cut to their dividend right? The stock I believe still closed up generally when that happens there’s going to be a significant change in price to that stock, because income investors are going to unload it. We’ll see what ends up happening with 3m but I’ve only ever really done that maybe once or twice where I’ve kind of completely repositioned. I may go from owning just Coca-Cola to maybe owning Pepsi or toning both or something like that within the same sector, but it’s very very rare that I’ll kind of completely exit.

One thing and as far as looking to deploy new capital especially when I have the kind of chunks of capital which as an entrepreneur often we have kind of our standard cash flow and then it can be a chunky type of pay whether you have an exit in a business, a big liquidity event or for some so something. In those situations normally what I do is I’m putting that capital into something that’s just super simple. In this case, you know maybe treasuries is generally what I’m doing in a treasury money market or something like that and then as opportunities present themselves I will then start to buy them.

And so this again comes with having your financial plan and knowing what the trajectory is because for me, what I’ve done Brian is I’ve basically created just a simple watch list of.. Hey, these are companies that either I own and I want to own more of or I own or I don’t own and I want to buy but I’m looking for them to be at a good price for me right? and there’s a lot of different ways I can calculate that I can look at you know for folks who are interested I can look at? Well, what’s their current yield? What are they paying today?

28:57.32 – Brian David Crane

Certain prices. Yeah.

29:13.30 – Ryan Coisson

Compared to the 5 year average right? if their 5 year average is 5% and the current yield 7 I know that it’s 2% higher right? or 40% higher than the average that tells me that either the yield’s been growing like crazy which is easy for me to check. Or this stock is dramatically undervalued in comparison to the last five years right which again is very easy to check and so you’ll find that during certain periods. It’s somewhat cyclical right? You might have energy companies, get beat up. You might have utility companies, get beat up. Maybe companies that are kind of like pharmaceuticals like Pfizer or Bristol Myers Squibb or Amgen or something else they get beaten up and you start buying and so during different periods of time. I’m sort of acquiring more shares of a lot of these companies.

And still trying to think of that overall balance and one of the hardest and simplest things about being an income investor is that you’re often not over here fiddling and tinkering around you’re staying patient and sort of vigilant. You’re tracking kind of what’s going on and and all again with technology nowadays it is also simple for us to do. But again, it’s just that little by little you’re building the nest and and again, since we kind of mentioned before that I do both investing and trading I think that.

The Mindset Shift Between Investing and Trading: Separating Short-Term and Long-Term Strategies

30:45.73 – Ryan Coisson

You have to and it’s just like I talked about as an entrepreneur and then as an investor we have to separate these and think differently an investor is going to particularly in this case I’m calling myself an income investor. An income investor is going to add to their portfolio.

They’re going to continue to build over time. An investor is looking to take advantage of short-term weakness or strength within the market and to make a profit sometimes using some form of leverage either in options or actual margin or something like that.

And then they’re looking to turn that quick profit often in a short period of time for some people. It’s minutes, days , weeks , months but certainly less than a year most likely and then for me that mindset. Oh yeah, sorry. It’s Twitter.

31:34.84 – Brian David Crane

I think you meant trader for that second part. Yeah sorry go ahead.

31:40.89 – Ryan Coisson

But that trader Mindset is very very different than the investor mindset and so you can’t bring either of those into one another right? When I’m trading, I don’t want to think like an investor. When I’m investing, I don’t want to think like a trader. And so, what I do to to help that is I have separate accounts. For those separate activities right? It’s just like if you’re starting a brand new Business. You know it’s probably a good idea to have some sort of entity formed Separate Bank account. All of that stuff. Everything’s Siloed and separate right? This gives us the sort of mental clarity for it, same with investing and trading.

32:18.38 – Brian David Crane

How often are you then looking at the value of your investments? Not the ones that are in the trading bucket, but the ones that are in the investment bucket like how often do you look at that?

Why Ryan Prioritizes Income Generation Over Portfolio Valuation

32:28.10 – Ryan Coisson

So that’s a good question. I think again, I learned this from my original mentor. I think it’ll change at different phases but currently I don’t care nearly as much for the value of the overall portfolio. But rather the income right? So one of the first things when you log in to any brokerage account. They kind of make it front-end center but really one of the first things that I do is when I log in to my brokerage account I’m looking at the income.

33:01.70 – Brian David Crane

Yes.

33:03.44 – Ryan Coisson

That my portfolio is going to generate in the future and that to me is the most important thing right? So think back to your situation. You know it’s March 2020, you’re cruising along and then all of a sudden you know in a week the Dow drops 17 % or something like that. We had like a big 90900 point down day. We had logged the worst week in market history since 2008. You know the great financial crisis, a lot of people are afraid to log into their brokerage account. You’re seeing crypto assets move astronomically faster to the downside and there’s a lot of fear there right?

There’s a lot of uncertainty there. There’s a lot of them. For people who imagine if you’d started living by the 4% rule in January of that year and then you just saw your portfolio drop almost 20% in a week. Imagine the fear like that gives me a pit in my stomach just even thinking about it.

When I’m logging into my account. Yes, my portfolio balance is down but my actual income was rising right? And so by having sort of that paradigm shift I’m now far more kind of cool as a cucumber.

34:29.70 – Brian David Crane

Yeah.

34:31.69 – Ryan Coisson

Of course nobody wants to see their portfolio balance go lower but I know that this income is strong. I know that this income is safe and so what does that allow me to do because you can see again. So even during that period of time companies were.

34:42.70 – Brian David Crane

But how is it that you knew your income was rising?

34:50.97 – Ryan Coisson

Raising dividends right? Or I’m reinvesting dividends at this point so every dividend that’s being paid either some companies pay monthly some pay quarterly, so you know March are getting your dividends coming in that those dividends are being reinvested so the income continues to rise. Yeah.

35:05.60 – Brian David Crane

Got it. Yeah, thank you.

Deploying Capital Strategically and Taking Advantage of Market Dips

35:09.63 – Ryan Coisson

But during that period the biggest thing that this gave me an advantage for was now because I also had capital on the sidelines which is what income investors always do to have money to deploy into assets. I was able to buy stuff at prices that I couldn’t have bought for. 10 years you know or more depending on the particular company. So it really allowed me to have this sort of almost like quantum leap forward in a lot of my positions to get companies when they were paying you know dividends, because the price was so low. You know like an energy company might have been eight nine almost 10% for a company that had been around forever and is super super strong. But then you had a ton of share price appreciation and you’re getting your dividends reinvested.

35:54.79 – Brian David Crane

But

36:03.40 – Ryan Coisson

When prices were really really low. So there was a huge opportunity. It also allowed me to play a lot of asymmetric bets. You know when I saw Ethereum heading down towards a hundred bucks I thought it was a good idea to deploy some of that capital there right? and then obviously if you’re. Doing asymmetric bets, my objective there is that when I have wins to pull that capital and kind of funnel it into these income investments right? I may leave some for asymmetric bets, some for say taxes, etc. But a lot of that’s being pulled over to make more income investments right? So if you get you know my biggest asymmetric that was over 150x, so if you’re putting smaller amounts into those types of investments, but if you’re getting ginormous returns, the ability for you to rotate there is incredible. It was a crypto investment. Yeah.

The Role of Asymmetric Bets in a Diversified Investment Strategy

37:04.67 – Brian David Crane

Um, what was that 150x bet just out of curiosity? Yeah, super interesting. Okay so I want to shift here just slightly because I I think that the as a side note, I was working on a piece with one of our writers yesterday about the difference between being rich and being wealthy, and the definition for wealth is effectively being an income investor and that you can live off of your income that your investments produce right? You’re basically above your burn rate for lack of a better way to put it so you bring in 100, you spend 90 at the end of the month you’re going to have another 10 that goes into that can be reinvested, and I’m trying to make it simple for folks. But so in your case. As you’ve gone through business and your career. What was the point at which you became wealthy and what I mean by that is that you were able to, live off of your income investments, and because I assume you’re in that case but like when did that happen? And how did it shift? what you spent your time on?

38:23.47 – Ryan Coisson

Yeah, so I don’t know that I could pinpoint a specific day looking back. You know my career has had a lot of different paths. I had gone very deep into the world of building websites and media type content websites. I’ve managed a big team of writers for stuff like that. I’ve moved and gone all in on the e-commerce space and moved to Asia and spent time with a business partner building offices in the Philippines and China. And I’ve gone and built information businesses starting back in 2006 that were related to everything from study guides for college, to rock climbing, to potty training, to E-Comm, to investing, all over the board and you know I think.

39:14.99 – Brian David Crane

Much. But..

39:19.46 – Ryan Coisson

One of the things that I will say is I’ve felt the wealthiest years and years ago right? I can remember getting for a very short stint. I did some client work and I remember, the first client I ever had paid me $12000 upfront for this project and they were doing boat rentals and I added 6 figures to this guy’s business top line in a month, and he was ecstatic and I was like that when that happened, and I immediately was like, wow! I now have a skill set that can sort of control my destiny, right? I knew that I would never not be able to earn much?

I started trading in 2003, I’m still doing that 2024 right? There were some breaks in between there, but to me, it’s remarkable that something that I learned over 20 years ago, and have been kind of optimizing throughout time has continued to be something that I’m doing today, and that longevity to that skill set has been incredibly empowering. And it’s one of those things you know Brian..

40:34.88 – Ryan Coisson

If you think about it, I hate to throw numbers out because it often gives people the wrong idea. But when I first started with trading, I tripled my money so 300% of my money in 90 days um back in 2003 this was probably one of the worst things and best things that ever happened to me because instantly I thought I had the Midas touch right? I thought I could never fail and I had to learn a lot of lessons the hard way, and kind of through the beats of life understand what it is to be a trader and to want to be able to do that in the long term now. Thankfully I still hear right? I survived those mistakes and I did it early enough to where the amount of money was. Very very small in comparison to what I’m trading with now, then I look at the market had been kind of choppy, and then we had a really strong bull run towards the end of last year, to the beginning of this year and now we’re at, new highs again.

Well during that period of time, trading was going incredibly well and I had returned another triple digit return in a matter of a few months and now this is on my entire account not just on a few trades and so and I’m doing this in a very very disciplined way where I’m not trading.

Knowing When to Trade and When to Stay Out of the Market

42:01.97 – Ryan Coisson

Generally speaking with more than 10% in any trade I have very specific stops. I don’t have more than a certain amount committed to the market at any time but it was just a great season and you know one of the things that and I say that is because for the last month and a half 2 months. Haven’t been doing much trading at all and the reason is the market shifted right? It had started to pull back and there was more Intraday volatility and I didn’t see a ton of great opportunities, and I bring this up because I think being wealthy, is being in a place where you don’t need to do the thing that you do to be able to live and survive right? So because I believe that very few people should just be a full-time Trader right? They should have some other source of Income. Unless you want to go work as a trader, being a trader for yourself and managing your own money is often very different than somebody might imagine right? I’m making a few trades a month. I’m not sitting in front of my computer watching the market constantly? So yeah, firewood..

43:10.96 – Brian David Crane

Yeah but I think that because there’s an important point there which is that if you are in your own mind a full-time trader, then you sit at the computer every day or you at least think you should be sitting there doing something right? and it doesn’t matter what the season is. The market sentiment generally speaking, like you said, take that couple months off because you’re not a full-time trader because it’s not you’re not implicitly committed to it for lack of a better way to put it right.

43:41.22 – Ryan Coisson

Yeah I think that it’s a mindset right? So for me as I think of these habits of a winning trader right? And that’s something I tried to impart on the students that I help with this philosophy of trading is one of the habits of winning traders is knowing when to trade and basically not to trade, and so we don’t want to force the trades and so I’m not trading doesn’t mean I’m not reviewing my watch list and doing the things that I should be doing but maybe the opportunities don’t seem as good. As they were three months ago, by having the ability to have others you know passive income streams, whether it’s from dividends or businesses or whatever you know a business pays me a salary etc.

All of these things, I don’t need to make trades today to eat right? And I have a large portfolio of investments that helps me generate income I’ve got from other businesses. And I just have structured my life in a way to where I’m setting myself up for success and I know one of the biggest issues that most traders face is, over trading right? So if I know that out the gate. What can I do? How can I build sort of a fence around the idea of over trading and keep myself away from it and that comes with all of the kinds of protocols or rituals that I have as a trader.

45:16.37 – Ryan Coisson

I try to teach people because I think again if you are the one who’s managing your own money you should care a lot about that. But you also need to be indifferent about the result you get as a trader so you have to build in. Sort of protocols that protect your emotions right? The most important thing you have is between your ears and really it comes to not just your mental acuity or things like that, it’s your confidence. So if you are trading. In a very volatile market but your strategy lends itself to trading in the trending market your confidence is going to be eroded very quickly because in volatile markets we have this whiplashing.

You’re maybe used to this or sideways trending and so if you kind of bring the proverbial hammer to try and you know the screw in a screw. You might be able to get it into the stud but it’s going to be a hell of a lot harder than using a screwdriver or a drill that makes sense.

46:19.18 – Brian David Crane

It makes sense. So then what does your day look like? So what I mean is when you wake up, if you start what do the first couple hours of your day look like because you have this flexibility and wealth?

And I use it in kind of air quotes that allows you to decide where to spend your time like how do you spend it like how do you decide where to spend it?

46:47.20 – Ryan Coisson

I think there’s been different phases of my life. There was a period where I was full time like traveling all around the world visiting all sorts of places that I’ve only ever dreamed of visiting and sometimes even taking family members to my mom’s. I love Disney so I took her to Singapore and to Universal and go see Disney in Hong Kong, and just experience something that she’d likely never experience. That’s one of the great things that that money can provide. Those experiences were awesome I think.

There’s a dark side to the digital nomadic life that I think a lot of people didn’t really use to talk about. I think now it can be a very lonely experience. It can be very sort of disheartening to see different parts of the world that are beautiful experiences. Poverty or to experience a sense of pollution. Other heinous crimes and acts and things like that and and kind of it changes your perspective on a lot of things and I think you know pros and cons to a lot of that, but the isolation can be one thing that I found myself falling out of a lot of.

Habits and sort of routines that I prefer so when I came back to the United States, I really and I have been continuing evolving this but I spend a lot of time outdoors. I spend a lot of time with my dog. Going on hikes, I’m a big rock climber. I still have that adventure spirit, so I’m doing a lot of that stuff.

48:22.82 – Ryan Coisson

But on a daily basis. I have sort of a routine of I may spend 30 minutes to an hour throughout the day cumulatively. For my trading. Sometimes it’s less rare to be remote. I spend a lot of time writing now reading what I’m working on. Sort of getting a bit reinvigorated into being in sort of the publishing information business which I kind of had stepped back from after we got out of our ecommerce businesses. But yeah, I mean it varies and I think one of the pros and cons of being an entrepreneur that has that flexibility.

And maybe you don’t have the absolute necessity to be driving hard is giving yourself a little bit of grace and empathy, to kind of wander a bit and figure it out more slowly than wondering what’s wrong with you or like, I’m sad today like, I shouldn’t be ever sad like, that’s not the case right? That’s okay to kind of be sad or hang out and I’ve long gone from the days of like, I used to feel bad if I was like watching a movie during the day because quote unquote should be working.

According to who you know and I think everybody has different goals and there’s nothing wrong with people being hard driven to to success and at a different stage in my life. I was and maybe I’ll be back to that at some stage but at the moment I’m kind of more at a slower pace of quote unquote like living that. Somewhat semi-retired life of still working, but not working as nearly aggressively as I was in the past.

The Importance of Cultivating Friendships Outside of Business Circles

50:07.64 – Brian David Crane

And you had said at one point, I think in a mastermind that you and I were also consciously cultivating friendships outside of the entrepreneur space right? Yeah trying to get away from other business owners.

50:20.88 – Ryan Coisson

Yeah, I think for me, like a lot of people who are entrepreneurs and have been doing their own thing for an extended period of time. It can be isolating and you can live in a world where people are always talking about the future and bigger and better.

50:22.39 – Brian David Crane

For a variety of reasons and..

50:40.19 – Ryan Coisson

Things and all of that are fantastic like I love to dream. But I also like to be very grateful for what I’ve already done, and I think and again I don’t know exactly where this stems, from but for me when I was spending a lot of time with maybe only entrepreneurs, I started to minimize a lot of what I had done, and felt bad about the fact that I didn’t want to really be pushing as hard moving forward and that put me in sort of a negative mental space and sort of a downward spiral that was honestly quite challenging to get out of mentally for me, by putting my energies into spending time with people that are maybe within my hobby range. Whether it’s golf, disco, hiking, rock climbing, just adventures. I love to cook. All these things I found that when you’re doing something like rock climbing. For example, if I’m rock climbing with friends of mine. I’m not thinking about anything else right? I’m not sitting there wondering like, how is that company doing? Or something like that. I’m very dialed in and focused on that. And so getting out with those types of friends have been incredibly valuable cultivating that making specific trips and destinations to do those types of things. I really enjoy photography. One of the things I love about photography is the fact that it forces patience.

52:16.21 – Ryan Coisson

I’m a big landscape photographer. And so go to Moab, might be in Moab for a few days or weeks and you might go to the same spot day after day hoping to get the right lighting right? Everything about clouds and stuff like that to get one photo or what you like as the one photo for me. I don’t basically share those or anything like that. It’s just kind of for me but that sort of practice was very very healing for me and soothing. So yeah I’ve really enjoyed kind of getting lost in those types of things, and I find now that I’m kind of a balance side of it where I enjoy doing a lot of stuff with entrepreneurs and a lot of my close entrepreneur friends, kind of have been the ones that are sort of starting to encourage me to get myself back out there, doing some of the things that I’m very excited and passionate about it.

But I’ve been a bit hesitant right? I’ve always kind of been much more of a behind the scenes business builder and the way that things have sort of shifted in the last several years, as well as kind of how I see the direction of maybe teaching more of what I do with investing and trading. It seems to be much more of a forward-facing type brand which is honestly a fair bit of a stretch for me and my personality.

53:42.13 – Brian David Crane

Yeah, because you’re going to wind up being public facing using the skill of writing, using the business skills and the traffic skills and the marketing skills that you’ve got.

53:46.23 – Ryan Coisson

Oh..

53:56.90 – Brian David Crane

And doing it in a way how do I encapsulate this correctly? Like you’re going to wind up back in business with it right? Like it’s not going to be so, it’s not like you’re getting into creative writing and you want to go off and write a novel about The American West or..

54:13.20 – Ryan Coisson

Right.

54:15.25 – Brian David Crane

Like a James Michener novel about Southeast Asia or so I don’t know, like it’s that the writing is going to be in service of teaching skills around money and and asset creation and and and and marketing as I understand it right?

54:32.34 – Ryan Coisson

Yeah, and I think..

54:34.12 – Brian David Crane

Yeah, the last two I don’t know it’s like it has to do with options and selling covered calls potentially but just generally thinking about finance is that right.

54:42.30 – Ryan Coisson

Yeah, so a lot of this at least initially is far more about the investing side things, the trading side of things and really I think it’s a way of thinking. And part of like I said, I spent a lot of time reading. All sorts of books like I just like all over the map. But one of the things that I have always kind of asked myself is if there’s so much information right? About being a successful investor. Just letting time do its thing yet, we look at it. The fact that most people don’t have enough money to retire. They’re not even close right? And what causes these things right? Well a lot of it is people delaying it not knowing what to do sort of the fear terminology which is often said that the system is.

Designing it that way so that you turn over their money. They can get management fees. I think it’s part of that. But I think that some of it is just different right? and when we learn anything new, any skill. There’s complexities and intricacies that we don’t necessarily understand. If we don’t spend the time to to learn and and educate ourselves on that it becomes more and more challenging for us to kind of live within a world that requires that skill. And I think the one of the reframes that has dramatically helped me especially as far as putting myself out there which for people who aren’t creators, who don’t write or who don’t make content.

It’s sometimes hard to imagine the reactions that you get or how people interpret things, and how that may affect you because you may often think that the person isn’t affected by what you say. I can tell you that I have had a tendency in the past to be more effective than I should have by positive and negative comments. But I think that this reframe of, I think the the reframe is positive.

56:41.66 – Brian David Crane

You’re a sensitive guy. Don’t let anybody say you’re not a sensitive guy. Yeah, go ahead.

Teaching Financial Literacy and Helping Others Navigate Investing

56:49.56 – Ryan Coisson

Allowed me to realize that I have a lot of experience and knowledge in this space. For the thousands of students that I have been helping without really having to put myself out there just based on my existing business that I had.
The response has been tremendous and the feedback has been tremendous. But I think that I’m able to add life and a new dimension to a world that often feels stale and complacent. And part of my hope is that writing the content that I’ll be creating more and more of is going to allow people to kind of catch that vision and excitement for sort of the possibilities in our head. And that’s sort of the same vision. The excitement I caught when I was 17 years old, you know the same reason right? I think back to how we’ve known each other for a long time. And broadly speaking, my general personality is a little bit more preserved and introverted. If I were to tell you when I was 17 like I flew to California from my first event that I’d ever been to..

57:50.34 – Brian David Crane

Quiet. Yeah.

58:05.90 – Ryan Coisson

Where I met my first mentor, who later sold me his business that I went there by myself. Like this is 2002 or 2000, early 2003 and I had nowhere to stay. I didn’t have a credit card. I just went and I just got it figured out right and it did right. I literally like everything just unfolded and I put myself into a very uncomfortable situation of not knowing where I was going to sleep. Not really having a ton of money for food like I was willing to just sleep in the hotel conference center right? Like I didn’t care and that’s how excited I was about this new world. This new understanding and I like coming back to that feeling right?

I remember the moments as I’ve been kind of writing about some other stuff like, the moment I’m sitting in this dimly lit fourth spare bedroom on the lower level of my dad’s house, and using this massive Dell computer like logging on and it’s making this horrendous noise that we all remember from dial-up connections, and hearing that you got mail. And then logging into the now defunct options express and transferring that first.

59:36.41 – Ryan Coisson

Thousands of dollars into my brokerage account money that took me a while to save up money that I sacrificed some of my prized possessions to sell so that I could have that money and thinking back to what it was like when I.

59:48.16 – Brian David Crane

And..

59:53.41 – Ryan Coisson

Was literally almost trembling as I was hitting the enter key to make that transfer to start that journey and realizing that we live in a whole new world now and misinformation is more rampant than ever. The more I talk to my entrepreneur friends like yourself, the more I realized that sort of a steady hand, a steady voice to provide financial cues and sort of proper trajectory is needed and these are very very smart individuals who are missing some of the most.

01:00:21.62 – Brian David Crane

Yeah..

01:00:29.70 – Ryan Coisson

Essential and just basic understandings of the market and it’s dramatically for a high earner. You know the mistakes are even more compounded and I think that now I see it as a sort of a disservice to not do it. So I’m excited about it.

The Power of Long-Term Thinking and Patience in Building Wealth

01:00:46.00 – Brian David Crane

Yeah, I can say that, well I mean a couple of things. I admire but you one of them is that I think you have a perspective on time.

01:01:01.36 – Brian David Crane

You have a perspective on time and then you actually put into action that perspective on time in an intelligent way that is quite admirable. A lot of people, myself included, look at the Math. Yes, we should be doing this. It’s not happening like let’s try to make it up in some other way by taking a higher risk bet because I’m good at high risk bets in other areas or at least I think I am. But more importantly, the sort of like the rituals and the rhythms and I don’t mean to use 2 R words in a row, but the rituals and the rhythms around what you’re doing and why right?

So like you’re very conscious about what season of life you’re in, and what you’re doing and that’s why I asked you how you kind of structure your day to also get a sense of what you’ve had this journey for. 2021 years sounds like from when you first flew to California and you’ve got a lot of experience and you got a lot of people who go, “Hey Ryan this is one of the reasons I reach out to you.” is like I’d love to talk with you because I know you know a lot about this but you’re also not super public. I was stumbling around on PB code asking you how I signed up for your newsletter because I couldn’t even find the box because there isn’t one actually.

And so that’s what led into this conversation. So I think it’s a beautiful transformation. You’re going through and there is space in this transformation for like a lady, a family, like it’s all been very left brain business oriented and hobbies like what’s happening on the questions of the heart.

01:02:41.36 – Ryan Coisson

Yeah, for sure I think if the right woman comes around it, it makes sense. That’s definitely something that I want you to know? I want to have a family and kids obviously. I’ve got my dog right now. So he’s treated in high royalty at the moment.

01:03:00.20 – Brian David Crane

Are they?

01:03:00.90 – Ryan Coisson

But yeah, for sure I mean I came out of a serious relationship a while back and I sort of gave myself permission to kind of heal from that. And I think, kind of work on myself and look for the right relationship rather than just kind of trying to jump into another relationship. And so I think, especially with the matters of the heart, I think our emotions can sometimes get the best of us right? So I’ve had this tendency in the past.

01:03:21.63 – Brian David Crane

Income investor one on one right there.

01:03:38.12 – Ryan Coisson

Try to move too quickly into new relationships and I think I learned trying to learn from that lesson, but to go back to what you said about time, I think time in the world, we live where everybody thinks so much about how much we’re getting done. A lot of it sometimes are unnecessary things. There’s a new book I haven’t completed the whole thing, but the premise is you know in the title. It’s called ‘Slow productivity’ by, I think his name’s Cal Newport.

But generally speaking, the idea is very simple right? If you look back at some of the greats in time, Einstein or Benjamin Franklin or Jane Austen or something like these writers, and you think about how well they created these seminal works right? Or these seminal inventions or just had a tremendous impact. But over there, if you look at an extended period of time, they weren’t producing a lot all the time right? There were these seasons or there were a 10 year period that might have gone by and 5 bestselling books that have been around forever from that period and..

01:04:41.40 – Brian David Crane

Yes.

01:04:52.82 – Ryan Coisson

I started to think about that. A friend Andre who’s a brilliant writer as and name’s Andre Chaperon, somebody I’ve looked up to for a very long time had recommended that book to me. I just sort of thought that’s kind of how I’ve always like thought about my life like I don’t want to create all of these little things, all these little fires I want to think like okay, what’s the project I’m going to focus on? So during covid I really sunk my teeth back into a E-Commerce business and my focus was to grow that E-Commerce business and a very specific intent, and I like was all in on that. And my all in wasn’t working 10 hours a day or anything like that. But like my mental focus was really driven on that, I think from a project standpoint that may make a lot of sense but to bring this back to the investing standpoint.

And again, those financial queues and to where we originally started with the bitcoin price coming down, one of the things that I talked about there is by having kind of your asymmetric bet bucket which is what I would call that investment. And if we look at the 2 main assets in that space again, say Bitcoin and Ethereum right? if you believe in those assets, the idea should be that you have your buckets and anytime there’s weakness and especially severe weakness.

01:06:22.87 – Ryan Coisson

If you have the capability, you add to those bucket,s and if you have been doing that, since I bought my first Bitcoins in 13. But if you had been doing that for any extended period of time or maybe even into the future, you would have done insanely well.

01:06:25.95 – Brian David Crane

Yeah.

Understanding position sizing and risk management in asymmetric bets.

01:06:42.83 – Ryan Coisson

Right? The fact it was all you had to do was wait and have the mental fortitude to not sell when everybody said you were an idiot and that bitcoin’s dead and all of these sort of things and will that continue to play out I don’t know right? but I do have those buckets and I’m waiting, and just continue to wait and I have a plan in place of how I will start to rotate out of that asset class at specific prices because at the end of the day, like if you have a certain amount of money, like maybe you want to do other things right? Maybe you want to do charity work or maybe you want to take your family places or maybe you want to buy a mid-century modern home or whatever it might be to restore something. Ah so the investments are there as a tool for me right? They’re not just there to go.

01:07:31.28 – Brian David Crane

Yes.

01:07:38.75 – Ryan Coisson

Build some big old pile of money. These are tools.

01:07:41.20 – Brian David Crane

There was bitcoin when you and I were talking about this in 2020. You also gave the advice and we didn’t really go into this but that the asymmetric bet as a percentage, In my case, my overall portfolio was too big. That was also part of it because I think that when you’re talking about this, when you had a one that did 150x, let’s say it’s less than 5% of your total, investable capital right? And what do you think about that? What do you think about it? What is appropriate to position size?

01:08:22.20 – Ryan Coisson

Yeah, the nature itself of an asymmetric bet is that you’re able to put much less than maybe your normal position size into something. So for example, like an income investment, if I have a hundred thousand dollars and I’m wanting to divide that up I might buy. Call it 5 grand or 4 grand of 2025 different companies right? So I’m spread out and I have sort of this diversification. Maybe my objective over time will be, I don’t want to own more than two and a half percent of any one individual company. That’s kind of where I fall on the income investment side. But then say you know from asymmetrical bets. I might say okay, here’s my overall portfolio. I feel comfortable having 2% there, 5% there, 10%

01:09:02.23 – Brian David Crane

Um, ask..

01:09:04.95 – Brian David Crane

Asymmetric bet Yeah..

01:09:18.62 – Ryan Coisson

And this kind of may change, you may have to do it based on what your actual cost basis was because as prices rise some of these can get dramatically out of whack, and maybe it’ll be assigned to trim off some of those profits which I have done over the years. There have been benefits as well to selling losers for tax loss , harvesting in the space as well. You can also buy those assets backed. At least during these times there has been no wash sale rules for this asset class. So that’s a benefit. But again, everyone’s tolerance is going to be a bit different over time because of the sort of the growth and because of the other income streams I have, and how I’ve kind of positioned myself personally, financially, I have started to allocate. More funds for specific things.

For example, now inside my retirement account I have exposure to both Ethereum as well as Bitcoin within there. I believe that over the long term I will have a much higher salary. Probability of growing that capital significantly but I still also own index funds in that retirement account right? So there’s a balance there. But I think no matter what somebody decides makes the most sense for them.

01:10:46.64 – Ryan Coisson

They should have a plan and an understanding of what that actually means for their overall financial situation. And I think part of the plan that most folks miss is, when am I going to sell? And for some things like, if I own a stock, you know say Coca-Cola, maybe I don’t ever plan to sell Coca- Cola, right? But if I own a Bitcoin, Ethereum, Binance coin or some other token or cryptocurrency asset at some point. If I own a whole pile of these, some of them I know are not going to be around forever most likely, So I’m looking to play them for a pump, and then maybe I will take a 5x or a 10x on something like that, and move it into those profits into a Bitcoin.

01:11:40.41 – Brian David Crane

Or of Coca-Cola.

01:11:42.10 – Ryan Coisson

And then maybe I’m hoping Bitcoin will double right over x period of time right? and so you can look to grow your money asymmetrically multiple ways right? So it’s like if you think about that 150x plus, I don’t want to I think the exact number was like 165 or something, but I don’t want to miss quote so we’ll just call it one fifty, but if you look at that and then if I were to take those profits, and put it into something that’s undervalued right? You think about the compounding of that especially over time right? and the nature of how I look at asymmetric bets is just like a venture capitalist would.

By 20 companies, maybe 80% of them don’t work but 20% do. But the gains are so big that you’re able to compound this money very very quickly. Now my objective is to be a much higher hit rate than what a venture capitalist would be because I’m bedding on an asset class. That’s rolling through momentum and I bet the way that I think about this too. Brian is not just like so many people think I want exposure to this market. Cryptocurrency market. Well, I can buy Bitcoin, Ethereum etc. I also bought Nvidia, I also bought Taiwan semiconductor, I also bought Silvergate Capital before it had gone on under and I made a 10x plus on that company before it ended up going under, because I had a plan for how I was going to sell, right? Versus like watching it go up and then crater off. I invest in, Bitcoin miners like clean spark or riot or marathon.

And so, I’m a shareholder in Micro Strategy right? So you can get allocation in lots of different ways and if you look at some of these stocks, you’ll see that um they can be more volatile, but the prices over the last 5 years especially the last several years have gone up dramatically, in comparison just maybe the broader market right? So you’re getting that asymmetric bet return and it’s not saying something like, just buying some Memecoin, or something like that. Yeah.

01:13:52.59 – Brian David Crane

Yeah, it makes sense. What do you think about Google now that they announced their dividend? Did they fall into your income investor bucket?

01:13:58.68 – Ryan Coisson

I think they don’t. I think it’s interesting that we’re starting to see companies like Google and Meta and stuff paying dividends. It’s a trend that is sort of unsuspected and expecting to see tech companies actually start to pay back shareholders because generally speaking, those companies just reinvest so much money back into R and D and into the business itself, that it doesn’t make sense for them to pay out a dividend. Let alone. they have, a massive growth. Um, built in so it’ll be interesting.

The dividends are far too low to be of interest and one of the biggest things I look for is sustained dividends being paid. I have exposure to these companies through index funds themselves. But I’m not counting on them being great income investments anytime soon.

01:14:55.23 – Brian David Crane

Got it. Okay, cool. Let’s wrap this up. What do you want? Out of this conversation people that are listening to this. Do you want them to go to PB code? Do you want them to go? What do you want them to do? Like you want them to wait a month?

01:15:09.73 – Ryan Coisson

Yeah I take..

01:15:11.75 – Brian David Crane

Circle the wagons on you on Twitter? I don’t know if you’re actually active on Twitter, like what do you want to do? yeah well first for all the ladies I think you need to be sending Ryan emails. That’s what I would say.

01:15:16.14 – Ryan Coisson

I’m not acting on any social media at the current moment, that may change in the future. I think you know the first thing I would love for people to do.

Key Takeaways and Final Thoughts on Financial Planning and Investment Strategies

01:15:28.97 – Ryan Coisson

Well, the first thing that I would recommend people do is to take a moment and actually think about your current financial situation, business, finances, etc. and come up with some sort of idea of what they’re wanting to actually accomplish. I think that. especially if you’re a bit older and you haven’t done this in a while, it’s a really really good idea to see where you’re at. There was a marketer, kind of disappeared a little like Howard Hughes -es named by the guy by the name of John Reese and I remember.

01:16:06.44 – Brian David Crane

Um, I know him and I knew him? Yeah.

01:16:06.46 – Ryan Coisson

Here’s this legend in space. Yeah, the legend in this space is that a big domain or early on, bought tons of great domains and sold some of them to really big companies. Owned a ton of single word domains, but he became sort of notorious in our space for. Being the first guy to do like a million dollars in one day through an information product and that was the 4 minute and John’s story is incredibly interesting to me because I remember it was a video of his that I was watching, and maybe he was telling me I hired him for some consulting at one point and he had talked about his early days and the amount of stress he had.

He was living in a shitty apartment shared with some friends in his bedroom. Really down on himself like what a loser I am, like I’m massively in debt, I’ve tried all of these ventures. Everything is not working out and I mean just credit card bills in a shoebox and he said, I decided one day to sit down. And just figure out how much of a loser I really am totaled up. Pulled out every credit card statement, right? totaled up everything that he owned right? and this is again like I think the 90s.

So It’s like you’re not just going on to Chase.com right? like he’s digging through everything and looking at and he wanted to know how big of a loser I am and that to me just made me chuckle just like you just did right? And he’s being sort of facetious to himself because he figured it out. And then once he knew the number, the boogieman was gone, right? Because before it was just arbitrary like, oh I don’t know this exact amount but I know it’s overwhelming and it’s on my mind all the time and it’s bad, right? Then he built a plan right? and..

01:17:57.72 – Brian David Crane

Yes.

01:18:06.58 – Brian David Crane

And it’s bad. Yeah.

01:18:13.42 – Ryan Coisson

Things took off and John went on to have a tremendous career and I believe he’s still building successful businesses just sort of in private. And so I think you should do the same thing, right? You should figure out well what kind of position I am in and what my personal financial situation is. Statements look like you don’t need to create some traditional P and L or something like that, and you don’t need to make it too complicated but just get a sense of where you’re at. I think that’s so important because then you can decide. Well, what do I want to do about this if anything not everybody needs to? Or maybe wants to, I guess needs to is probably the wrong way to say it. Not everybody wants to most people need but if what I’ve said resonates, I’m going to be doing a lot more writing and releasing trainings and content on Onlineoption.com

People are welcome to kind of follow along. Presently we send a ton of content via email to our students and members, we’re going to be doing a lot more to folks who are not students and members and making it. We’re going to be actually using our marketing skills to allow people to opt in and learn about what we’re doing. But if you’re looking for sort of a strong and steady voice and opinion on what’s going on in my world of investing and in my world of trading and why I think it’s important to be a long-term investor first to build the pillars of that. Before you turn to any sort of other types of investing or trading and yeah, we’d love to share that with you.

01:19:55.88 – Brian David Crane

So I do have one more question because you touched on something with an Online Option. Very interesting to me when you’re going through this process. What does this look like? Do you sit down with a spreadsheet and you basically say here’s my.. How does this look like you sit down and you go? Like here’s my monthly income statement and it’s from your business. It’s from your different investments. You look at your outgoing your incoming. How do you do this like, what is it and assume that you’re a business owner right? You’re not working. You don’t have a salary but like to assume that you’re a business owner. What do you like? You start from what do you do?

01:20:36.37 – Ryan Coisson

Yeah I think I mean the first step is if you’re a business owner then I would create a little bit more of a traditional P and L like what are your assets? What are your liabilities? And think of it from the personal standpoint first, right? So what assets do you have? Do you have a retirement account? Do you have this brokerage account? Maybe you’ve got a health savings account. Maybe you’ve got some cash in the bank. You’ve got a money market. Whatever, what does all of that look right? and then what are your expenses look like and figure that out. I think early days for someone who hasn’t really done this kind of stuff before.

There’s a strategy to play some offense and play defense right? anything on the defensive side like you might look at your expenses and go okay, I’ve paid 180 dollars a month in streaming services, right? Like do you need that Hulu account? Maybe, maybe not the right thing that you want to trim off. I’m not a believer of scrimping like, I’m not someone who’s going to sit here and say “Oh, don’t go. Have that coffee.”

I live here in Texas at the moment and everything here is more and more expensive. But it doesn’t mean that I’m not going to go pay $8 for a Matcha Latte. I’m still gonna do it

01:21:50.51 – Brian David Crane

Is that what Matcha Latte cost right now in Austin?

01:22:05.26 – Ryan Coisson

$7.95. That’s crazy. But yeah, so I would start thinking about offense and defense, right? and some simple buckets right? If you’re a business owner and you don’t have some sort of business retirement account, obviously, a great thing to do. There is talk to your accountant about how much you’re paying yourself from. But I think everybody who owns a business should probably pay themselves a legitimate salary from that business if they can. And then obviously dividends or distributions or something depending on what’s going on in the business. But yeah, sure.

01:22:27.53 – Brian David Crane

Can I ask a question on that?

01:22:06.00 – Ryan Coisson

Yeah, sure.

01:22:07.44 – Brian David Crane

Yeah, so you mean that they should set up? Let’s assume they have an LLC, that they should be doing the S Corp Election and paying themselves a salary out of that LLC so that then they can funnel? Wow I don’t know if it’s then they can funnel but that way they can fund things like a solo 41k or a set by array is that what you were saying?

01:22:52.22 – Ryan Coisson

Yeah, whatever structure is going to, it’s going to depend on what’s best for that particular business, but what the end goal should be, you want to have some form of whether it’s a solo 41k. You’re maybe the only person on salary or something like that in that instance, and you’re contributing. I think the max for that is like you can do 22 and a half thousand personally, or maybe it’s 23 this year and then the business can contribute you know like 43 and a half thousand to a solo 4 okay, right? So it’s like, my objective in saying that is and and maybe you can relate to this Brian. I know other entrepreneurs I’ve talked to can think back to when they started their business and they said well if all I would have done was actually set up some sort of business. Personal retirement type situation and max that out every single year instead of hoping for that big hit to sell I would be in a tremendously different financial position because think about it for a moment right? If you’re a business owner and you’re contributing combined between personal and business, call it 68 thousand dollars a year.

01:23:46.24 – Brian David Crane

Yeah, and..

01:24:00.22 – Ryan Coisson

To that. All you did was that for 10 years you know you’re going to have a pretty solid retirement in and of itself right? You look at what? Roth IRA I think now, I don’t know the exact number I think it’s 7000 or something like that if you’re under 50 per year. But that in and of itself is a huge win.

01:24:06.51 – Brian David Crane

Yes.

01:24:20.30 – Ryan Coisson

And so figuring that out I think is important also for certain individuals. It could be beneficial because it’s sort of forcing yourself to actually save and invest and again amateur investors who want to spend 0 time. Learning about the markets should probably follow advice from someone like Warren Buffett and just buy the index. There’s many ways that you can buy different indexes and having different diversification is probably a good idea but that would be a place to start. I think then think about your actual objective and end goal. This is always the most important thing. What do you want to accomplish right for me?

My objective is to create that continued growing income stream that’s a safe , secure stable that helps me sleep incredibly well at night. Do I need that income stream now? No, so I’m still investing for income. I have a sort of waiting for growth and I’m still reinvesting those dividends so I’m wanting share price appreciation and income growth. But as I get older and older that rotation may change a little bit or as I maybe start to liquidate some of my asymmetric bets. How I redeploy that capital might be different a bit, but it all comes into kind of a written plan.

I’m a very text and paper person like literally right next to here. I have 3 different notebooks that serve 3 different purposes and so I write in these a lot, but I have a written plan that I follow, and here’s the greatest advice I can give somebody is, you don’t have to figure it all out upfront if you want to be an income investor. Go buy 1 share of an income stock you like, maybe it’s Exxon. Maybe it’s Coca-Cola, maybe it’s Apple. Maybe it’s Merk whatever, and just know that again. It’s little by little the bird builds his nest.

You’re going to learn so much more by doing and studying than just sitting here trying to read and understand and go. What’s the forward P ratio? What’s this? What’s there where you earn this and these sorts of things? So some of that matters right? Some of it might not suit your style and temperament but you have to take some little bit of action moving forward. So don’t get caught in this sort of analysis.

Paralysis or paralysis by analysis is what I think.

01:27:03.80 – Brian David Crane

And yeah, but I think it’s also key to know your style and your temperament.

01:27:09.88 – Ryan Coisson

Yeah, exactly and I think again try to really know it right? Because again I think if you’re a serial entrepreneur starting new things all the time, and that maybe your income or your just liquidity events are again lumpy. Then if you invest for income and you use some of that money for those big liquidity events to create income, then it’s far more smoothed out and that can make your life a lot more easier. And again, think about if you have children. There’s all sorts of things that you can do.

01:27:35.41 – Brian David Crane

Yes.

01:27:45.52 – Ryan Coisson

Think about tax efficiency and stuff like that. I mean there’s so many things that can come into play and at the end of the day it can become daunting for a lot of people. But again I just can’t emphasize enough that the action over sort of over analyzing is critical.

01:28:02.59 – Brian David Crane

Because you get the benefit of time. Sorry like yeah.

01:28:03.78 – Ryan Coisson

And just taking yeah, it’s just like little steps moving forward and you can even go back through, I mean I remember at one point to go back to John Reese’s story thinking, how do people get in massive credit card debt, right?I had a business when I started when I was in college. It was successful. I was doing well and then the business blew up. The payment processor completely screwed me and stole money out of my account. They ended up being big lawsuits class action against them I went from. I had a successful business with basically my 2 credit cards that had small limits on them like eighteen hundred bucks and thirty four hundred bucks. Both had double the limit because the money that was being sent to them never got processed because the money was no longer in my account.

And I was in a really tricky situation. Thankfully, I got myself out of it, but there was a dramatic swing. I think about people who get into these situations and then they just sort of defer. I don’t want to look at it I don’t want to.

01:29:05.10 – Brian David Crane

Tricky.

01:29:19.24 – Ryan Coisson

Think about it. The same thing happened. I got out of college and I looked at my student loan balance and I was mortified. You know I had studied abroad a little bit. I had gone to a private college initially then I transferred. I had taken extra classes in the summer just kind of for shits and giggles because I was interested in random topics and then all of a sudden I realized wow I’ve got like 50 thousand dollars plus in student loans. Did I want to have those forever? No, because I read stories of people. They realize they’re paying interest for 15 years and they barely paid any principals. So I built a plan and paid them off in a couple years and it was done.

So again, my point at sort of sharing that kind of stuff is if you don’t know, rght? What the situation is how can you build a plan to move forward, right? If you don’t know your end objective in that case paying off a student loan or building a passive income stream, how are you going to find your way to it? You don’t maybe need to know all the information upfront just having the goal and the objective you often find yourself.

Being led that direction and people pop up into your lives for that. I kind of made this commitment of bringing myself out there more, talking more about this stuff and out of nowhere you reached out and asked if I wanted to be on your podcast right? like, that’s how life works.

01:30:46.44 – Brian David Crane

Funny. You have a tremendous amount of self-discipline. Yeah, so what is that? What do I attribute that to?

01:30:48.70 – Ryan Coisson

Maybe.

01:30:58.29 – Ryan Coisson

Um I don’t know, I did sports so I was in gymnastics and other sports and did martial arts and kind of a lot of things that required discipline I think growing up. Some of my heroes, I had a long lineage of family members that those who lived in Europe as well as the US were military folks. So there’s obviously that component of discipline a lot of my heroes growing up, in the 80s that you’re thinking of like the loans, The Schwarzeneggers, The Van Dams and stuff like that. They all had this sort of Jordan, yeah. I grew up in Chicago going to Bulls games like they had this, just air about them this presence of discipline and you watch any of those kinds of old action movies and it was always the leading.

01:31:37.36 – Brian David Crane

Michael Jordan

01:31:51.70 – Ryan Coisson

Star had this incredible discipline of like either getting back in shape training for a fight or avenging their mentor or something. So maybe that’s where it stems from but I don’t know if there are days where I feel like I have disciplined there’s days that I feel like I don’t.

01:32:01.23 – Brian David Crane

Yes, but so many of your stories. They have a thread of like, I made a plan and then I executed on it. I made, I took like an honest assessment of where I was at and I’m paraphrasing your story about John Reese which wasn’t you but like I looked at it, I got a clear vision of what it was and what it wasn’t and then I decided.

01:32:14.90 – Ryan Coisson

Yeah.

01:32:25.37 – Brian David Crane

Was going to make a change right? that takes you know it takes honesty and it takes discipline. So I think, definitely, two traits to admire so cool. Thank you Ryan, we will put into the show notes.

01:32:28.53 – Ryan Coisson

Yes.

01:32:37.36 – Ryan Coisson

Awesome. Well thanks for having me.

01:32:42.11 – Brian David Crane

These different links and when you decide to let’s say, turn on the marketing funnel, would happily contribute a little bit and try to get the name out there.

Alright cool I’ll talk with you later.

01:32:53.93 – Ryan Coisson

Awesome. I appreciate it man. Cool, thanks for having me.