Please welcome Ryan Coisson, whom I’ve known for more than 10 years, to the show. He’s a digital business owner, content marketer, outdoor adventurer, and finance whiz.

Ryan is a pro at creating high-level processes, including planning and building specific — and I mean very, very specific — actionable steps to achieve the goals around those financial plans.

He’s also just a nice guy. That’s why he agreed to join me today.

We spent a ski season in Whistler, Canada, living together in a shared chalet with entrepreneurs. Since then, our paths have crossed, diverged, and then crossed again.

I asked him to come on the show to talk about one of his companies, Perfect Biz, as well as some of the other projects he’s involved with, like Online Option and more on finance and investing.

I hope you enjoy this show as much as I enjoyed recording it.

Favorite Ryan Coisson Quote

“Winning the game to me looks like creating what I would call an income engine. So a portfolio that generates income for me now. I want that income to do a few things: continually growing, be safe and stable, and be diversified across different sectors.” – Ryan Coisson

Additional Resources

• Online Option
• Slow Productivity: The Lost Art of Accomplishment Without Burnout, Cal Newport

If you’d like to stay updated on what Spread Great Ideas (aka “SGI”) is up to, you can do so on X, Facebook, Instagram, and LinkedIn.

Full Transcript of Our Conversation

Introduction and Background

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 yeah, 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.

Key Financial Strategies for Entrepreneurs

01:22.82 – Ryan Coisson
Yeah I think so you know I mean to to just add a little tidbit to that you know 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
Um, 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. You know 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 you know 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. You know Brian 1 of the tricky things entrepreneurs in particular or folks who get enamored by an asset class and you know 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.

03:06.30 – Ryan Coisson
But in my opinion the most important thing is your earning power. Um, we believe you know, 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 um for 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 well where am I trying to go. And said period of time I think one of the traps that that you had fallen into is um, this exuberance for the asset class and kind of on the other side. What might be driving that currency debasement? You know, ah greater economic troubles all of these sort of things. Um, 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 you know, kind of between the ears which is the most important thing as an investor and Trader especially um. It’s going to be very very difficult for you to operate your business successfully as well.

05:03.23 – Brian David Crane
Um, super well said? Yeah, super well said. So there’s 2 threads in that one one is that like in my business or in your business. Um I have a modicum of control right? like I have the ability to fire hire. Deploy capital change strategies to Xy and z as opposed to being a passive investor in something like bitcoin or a DeFi protocol or whatnot where um yeah I just don’t really have any I’m I’m purely like a spectator or retail in that sense right?

Understanding Market Fundamentals and Sentiments

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. You know 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. You know twelve eighteen months um 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. Um, said statement from you know the fed chair or something is going to weigh on the economy even more you’ll see the market move dramatically, you know when we’ve had different presidencies. We’ve seen a tweet you know 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. Um, the main storyline for a cryptocurrency like bitcoin which is what this 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. Um.

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. You know, kind of shaking out continued shaking out of bad actors within that space. We see continued development of ah institutional development or institutional capital. You know being deployed to there where you have you know, pension up. There’s a pension fund recently. That came out and said that they had deployed $100000000 into the blackrock ah bitcoin Etf right? That adds a ton of validity to that particular space and you know with that adoption. 1 of the things. Um, as someone who believes that that category of investment is an asymmetric bet. Um, 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.

08:16.90 – Ryan Coisson
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.

08:28.62 – Brian David Crane
Interesting. Okay, what when you? yeah so when you think about um when you think about your own asset allocation. Let’s assume you have $100 and um, you own a business and.

08:30.47 – Ryan Coisson
Motion.

08:44.94 – Brian David Crane
Yeah, you have ah 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 dollars 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 um from my investing standpoint. You know my overall thesis is I’m playing for really 2 things: 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. Um, but then lastly what this really does for me Brian is so if you if your parents or my parents went to a financial advisor you know now or maybe when they were our age. They’re going to. 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.

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. Ah, vanguard published a study you know a couple years ago saying that the 4% rule needed to be addressed because they believed that over the next ten years the returns would be far less than the past ten 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. For example,

12:37.00 – Brian David Crane
Um, yes, this.

12:43.42 – Ryan Coisson
How much does that grow by next year um it’s not uncommon that you could have your entire portfolio grow 5 % or 10 um, you know the just little pay raises as I’d like to call them. You know 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 you know that maybe starts off as a trickle but then over time that becomes bigger and bigger and bigger and bigger now. Ah talk before about sort of this yield trap. Right? And so 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 seventies 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. Um two 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. Um, 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%. Ah 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 that you know, ah the dividend yield for visa is growing at over ten percent per year at the current moment. Um, so you know these types of. Things are really really important to me because now flip the situation and say I’m seventy years old and I’m wanting to retire and um 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 you know dividends are taxed currently preferentially so that’s.

15:45.94 – Ryan Coisson
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. You know all things that are going to make those golden years far less. Beneficial for you, your family, your grandchildren whatever it might be.

16:23.71 – Brian David Crane
Yeah, so the part on Broadcom and vise 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 um, you know, right now that. 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 1 of the 2 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 the yeah 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? Um, first off, you know a common thing that folks hear about is hey 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 um. Income investments growth stocks that pay dividends or stuff like that dividend growth stocks. Um, but 1 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&p with dividends.

Being reinvested. Okay and I say that because um, 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.

Um, So one of the things that I think people sort of get caught up in and and ah this is part of to your question is that well am I 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 a ah 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? um.

19:24.26 – Ryan Coisson
2020 2021 right? We had this big crazy market pullback and change and you know 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
Um, or used to drive anywhere.

20:13.96 – Ryan Coisson
Has consistently paid dividends for you know years and 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? and you know now right? I think that over the last while some energy companies and utility companies had been really beaten up. Ah 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. Um.

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? You’re benefited from so you know there’s a.

Saying I don’t know exactly where I heard it but and this is I apply this to you know, ah beng ah, an income investor. It’s you know, 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 you know, 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? and

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. Yeah, yeah, and and and 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 um like how often you are making ah a buy or making um.

24:48.11 – Brian David Crane
Yeah, like how often are 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.

24:57.20 – Ryan Coisson
Yeah, it’s not that much right? So here’s the thing. Um, so first I’m still young. You know I’m in my late thirties and so I’m consistently investing every month right? Automatically. Um, and this isn’t just like my retirement account type Situation. You know as an entrepreneur I have a ah you know a retirement account that I can yeah through my business that I can you know put in a significant amount of money right? that that type of investing is different right? so.

25:20.98 – Brian David Crane
Um, profitable business. Yeah yeah, a set by array.

25:33.41 – Ryan Coisson
Um, 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 you know that money. Is going to come out tax-free. You know when you’re retired. Um 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. Ah, 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. Um, during that maybe period of time so you have to sort of I guess think about that first and foremost right I think that 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 3 m.

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 3 m but um. 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. 1 thing and so um, 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 or. Ah, big liquidity event or for some so something. Um, 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.

28:53.25 – Ryan Coisson
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 you know? 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 you know 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 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, um, since we kind of mentioned before that I do both investing and trading I think that.

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, yeah, sorry yeah, it’s Twitter.

31:34.84 – Brian David Crane
I think you meant trader for that second part. Yeah sorry yeah, go ahead? yeah.

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 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
Um, how often are you then looking at the value of your investments not not not not the ones that are in the trading ah bucket. But the ones that are in the investment bucket like how often do you look at that.

32:28.10 – Ryan Coisson
Um, um, so that’s a good question. So I think again, you know and I learned this from my original mentor. You know, um 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 1 of the first things you know 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 Twenty Twenty 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 yeah, 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 twenty percent in a week. Imagine the fear like that gives me a pit in my stomach just even thinking about it. But

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
Um, yeah.

34:31.69 – Ryan Coisson
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
Um, but how is it that you knew your income was rising?

34:47.45 – Brian David Crane
Um, yeah, got it? okay.

34:50.97 – Ryan Coisson
Ah, raising dividends right? or I’m you know 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. Um, yeah.

35:05.60 – Brian David Crane
Got it? Yeah, thank you.

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 um 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. You know, 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 150 x um, so you know 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.

37:04.67 – Brian David Crane
Um, what was that 150 x bet just out of curiosity? Yeah yeah, super interesting. Okay so I want to shift here just slightly because I I think that the.

37:22.16 – Brian David Crane
I Was 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 um the definition for wealth is effectively being an income investor and that you can live off of your um. The income that your investments produce right? You’re basically you’re you’re above your burn rate for lack of a better way to put it so you bring in one hundred you spend 90 at the end of the month you’re going to have another 10 that goes into that 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, um, live off of your ah. Yeah, your income investments and because I assume you’re in that case but like when did that happen and how did it shift your um yeah when did it happen. How did it shift what you spent your time on.

38:23.47 – Ryan Coisson
Yeah, so I mean I don’t know that I could pinpoint a specific day looking back. You know my career has had a lot of, um, different paths. You know I had gone very deep into the world of ah. You know, building websites and media type content websites I’ve you know, managed a big team of writers for stuff like that. Ah you know 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 you know the Philippines and China. And you know 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 ecom to investing you know all over the board and you know I think.

39:14.99 – Brian David Crane
Um, much. But

39:19.46 – Ryan Coisson
1 of the things that I will say is I’ve felt um the wealthiest years and years and years ago right? I can remember um, getting you know for a very short stint I did some client work and I remember um the first client I ever had paid me $12000 upfront for this project and and they were doing boat rentals and you know I added 6 figures to this guy’s business top line in in a month and he was ecstatic and you know 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? Um I started trading in 2003 you know I’m still doing that 2024 right? Ah, there were some breaks in between there. But. To me. It’s remarkable that something that I learned over twenty 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 war. Um.

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 ninety 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. Um the hard way and kind of. Through the beats of life understand what it is to be a trader and to 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. You know, ah very very small in comparison to to what I’m trading with now then I look at you know 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 you know, new highs again. Well during that period of time. Um. 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. You know, a few trades and so and I’m doing this in a very very disciplined way where I’m not trading.

42:01.97 – Ryan Coisson
Generally speaking with more than 10 percent 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 two 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. Um, you know 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, you know, sitting in front of my computer watching the market constantly? Um, 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 of the um. You know 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 your um yeah, 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 you know 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. You know, 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. Um 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. Um, 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 um, really it comes to not just your mental acuity or or things like that you know 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 this or sideways trending and so if you kind of bring the. You know 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 Brent.

46:19.18 – Brian David Crane
It’s like ah it makes sense. So then what does your day look like so what I mean is when you wake up. Yeah, if you start what? 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? How are you? How do you spend it like how do you decide where to spend it?

46:47.20 – Ryan Coisson
Yeah I think there’s been different phases of my life. You know 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 you know family members to you know 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 and that’s one of the great things that that money can provide. Um, you know those experiences were awesome I think um. 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 um, sort of disheartening to see different parts of the world that are beautiful experiences. Tons of. Poverty or to experience a sense of pollution. You know 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 1 thing that I found you know myself falling out of a lot of. Habits and sort of routines that I prefer so when I came back to the United States you know I really and I have been continuing evolving this but I spend a lot of time outdoors. You know I spend a lot of time with my dog. You know, going on hikes . I’m a big rock climber. I still have that adventure spirit. So I’m doing a lot of that stuff. But

48:22.82 – Ryan Coisson
On a daily basis. You know I I have sort of a routine of I may spend 30 minutes to an hour throughout the day cumulatively. Ah, for my trading. Sometimes it’s less rare to be remote. I spend a lot of time writing now reading what you know 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. Um, but yeah I mean it varies you know and I think one of them.

49:00.64 – Ryan Coisson
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 you know. Wondering What’s wrong with you or oh like I’m I’m sad today like I shouldn’t be ever sad like oh that’s not the case right? That’s okay to kind of be sad or hang out and you know I’ve long gone from the days of like oh 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 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 and maybe I’ll be back to that at some stage but at the moment I’m kind of more at ah, a slower pace of quote unquote like living that. Somewhat semi-retired life of um, still working but not working as nearly aggressively as I was in the past.

50:07.64 – Brian David Crane
And you had said at one point I think in a mastermind that you and I were in that you were also consciously cultivating friendships outside of the entrepreneur entrepreneur space right? like yeah trying to get away from ah other business owners.

50:16.38 – Ryan Coisson
Um, yeah.

50:20.88 – Ryan Coisson
Yeah, yeah I think for me, you know, 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 I think and 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 somewhat of a downward spiral that was honestly. Quite challenging to get out of mentally for me, um, by putting my energies into spending time with people that are more maybe within my hobby range whether it’s you know Golf Disc Golf hiking Rock Climbing. You know, just adventures. I’m a big I Love to Cook. Um. You know all these things I found that when you’re doing something like that you know take rock climbing. For example, if I’m rock climbing with friends of mine. Ah I’m not thinking about anything else right? I’m not sitting there wondering like oh like how is that company doing or something like that I’m very dialed in and focused on that. And so um, getting out with those types of friends have been incredibly valuable cultivating that making specific trips and destinations um to do those types of things. Um, I really enjoy photography. Um, one of the things I love about photography is the fact that it forches.

52:16.21 – Ryan Coisson
Patients, you know 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? you know everything about clouds and stuff like that. Ah, to get 1 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 on um, ah, a balance side of it where and I enjoy doing a lot of stuff with entrepreneurs and you know 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. Ah, 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 and trading. It seems to be much more of a forward-facing type brand which um is honestly ah 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 um.

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 doing it 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 um, it’s not like you’re getting into creative writing and you want to go off and write a novel about you know the American West or um.

54:13.20 – Ryan Coisson
Right.

54:15.25 – Brian David Crane
Or about yeah like a James Mitchner 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? well.

54:32.34 – Ryan Coisson
Um, 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 um, far more about you know the investing side things the trading side of things and really I think it’s it’s a way of thinking. Um and you know part of you know like I said I spent a lot of time reading. Um. All sorts of books like I just like all over the map. Um, but 1 of the things that I have always kind of asked myself is if there’s so much information right? about being a successful investor. You know, 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 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 for people who aren’t.

56:13.32 – Ryan Coisson
Ah, creators who don’t write or who don’t make content. It’s sometimes hard to to imagine the reactions that you get or or how 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 um by positive and negative comments. But um I think that this reframe of I Um 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.

56:49.56 – Ryan Coisson
Allowed me to realize that I have a lot of experience and knowledge in this space. You know 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 um. The response has been tremendous and the feedback has been tremendous. Um, but I think that I’m able to add life and a new dimension to a world that often feels stale and complacent and you know part of my hope is that you know 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 you know and that’s sort of the same vision. The excitement I caught when I was seventeen years old you know the same reason right? I think back to how we’ve known each other for a long time. Um, and you know, broadly speaking. My general personality is a little bit more preserved and you know introverted. You know 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 , you know um.

57:50.34 – Brian David Crane
Quiet. Yeah.

58:05.90 – Ryan Coisson
Where I met my first mentor. Um, who later sold me his business that I went there by myself. You know like um this is 2002 or 2000 early 2003 and I had nowhere to stay. Um, I didn’t have a credit card. You know 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. You know I like coming back to that feeling right? I remember the moments as I’ve been kind of writing about some other stuff like oh 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 you know, 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 um are missing some of the most.

01:00:21.62 – Brian David Crane
Um, yeah, um.

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 you know now I see it as a sort of a disservice to not do it. Um, and so I’m excited about it.

01:00:36.80 – Brian David Crane
Um, yeah.

01:00:46.00 – Brian David Crane
Um, yeah, yeah I I can say that um 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 ah um, quite admirable. A lot of people, myself included. You know, look at the math. Go Yes, we should be doing this.. It’s not happening like let’s try to make it up in some other way by taking ah. Um, a higher risk bet because I’m good at high risk bets in other areas or at least I think I am um but more importantly, the sort of um, yeah, like the the 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.

01:01:25.35 – Ryan Coisson
You know.

01:01:38.51 – Brian David Crane
Um, 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 and how it that’s why I asked you how you kind of structure your day to also um, get a sense of yeah what you’ve had this journey for. But yeah, 2021 years sounds like from ah 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 couldn’t even find the. Box because there isn’t one actually and so that’s what led into this ah you know this conversation. Um, so I think it’s ah yeah I think it’s a beautiful transformation. You’re going through and there is space in this transformation for um. Like you know a lady, a family like it’s all been ah, very left brain ah business oriented and and hobbies like what’s what’s happening on the questions of the heart.

01:02:41.36 – Ryan Coisson
Yeah, for sure you know I think if the right woman comes around it. It makes sense. That’s definitely something that I want you to know? ah I want to have a family and kids you know 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 ah.

01:03:00.90 – Ryan Coisson
But yeah, for sure you know I mean I came out of a serious relationship a while back and you know I sort of gave myself permission to kind of heal from that and I think kind of you know work on myself and look for um. You know the right relationship rather than just kind of trying to jump into another relationship and so you know I think no I think I think you know, especially with the matters of the heart I think ah you know 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 1 on 1 right there.

01:03:38.12 – Ryan Coisson
Try to to move too quickly into new relationships and I think um, you know I learned trying to learn from that lesson but to go back to what you said about time I think you know time in the World. We live where everybody thinks so much about you know, like. How much we’re getting done. You know a lot of it sometimes is unnecessary things. Um, 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. Um.

01:04:11.75 – Brian David Crane
Newport.

01:04:13.73 – Ryan Coisson
But generally speaking the idea is very simple right? If you look back at some of the greats in time you know Einstein or Benjamin Franklin or you know Jane Austen or something like you know these writers and you think about how well they created these seminal works right? or these seminal inventions or you know just had a tremendous impact. But. Over there if you look at ah ah an extended period of time they weren’t producing a lot all the time right? There were these seasons or there were you know a 10 year period that might have gone by and 5 you know, bestselling books that have been around forever from that period and.

01:04:41.40 – Brian David Crane
Um, yes.

01:04:52.82 – Ryan Coisson
I started to think about that. Um, and you know 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 and um, you know I just sort of thought that’s kind of how I’ve always like thought about my life like I don’t. 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 you know during covid I really sunk my teeth back into a ecommerce business and my focus was to grow that e-commerce business and a very specific intent and and I like was all in on that. You know 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 and um, you know 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 and to where we originally started with the bitcoin price coming down, you know 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. Um. And if we look at the 2 main assets in that space again, say bitcoin and ethereum right? if you believe in those assets you know 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 buckets and if you have been doing that since you know 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. Um, you would have done insanely. Well.

01:06:25.95 – Brian David Crane
Um, yeah.

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 you know 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
Um, yes.

01:07:38.75 – Ryan Coisson
Build some big old pile of money. These are tools.

01:07:41.20 – Brian David Crane
Um, yeah, 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 of your of in my case, my overall portfolio was too big that was also part of it because I think that you’re um, when you’re talking about this when you you had a one that did one hundred and fifty x it’s not ah maybe it is I don’t know but it’s probably not a um.

01:07:55.15 – Ryan Coisson
Um, yeah.

01:08:08.63 – Brian David Crane
Let’s say it’s less than five percent of your total, investable capital right? And so yeah, what do you think about that? What do you think about it? what is appropriate to position size.

01:08:13.30 – Ryan Coisson
Um, great.

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 one ah $100000 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 1 individual company. That’s kind of where I fall on the income investment side. But then say you know from asymmetrical bets. You know 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
Um, asymmetric bed. 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 to selling losers for for tax loss ah harvesting in the space as well. You can also buy those assets backed. You know at least during these times there has been no wash sale rules for this asset class. So that’s a benefit. Um. 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, you know now inside my retirement account I have exposure to both ethereum as well as bitcoin within there. Um, you know 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 you know 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.

Asymmetric Bets and Cryptocurrency Investments

01:10:46.64 – Ryan Coisson
Um, 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 you know buoyancy you know some other token or or cryptocurrency asset at some point. You know 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 5 x or a 10 x on something like that and move it into those profits into a bitcoin.

01:11:40.41 – Brian David Crane
Or of 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 hundred and fifty plus x I don’t want to I think the exact number was like 1 65 or something but I don’t want to miss quote so we’ll just call it one fifty ah 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. You know, 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. Ah cryptocurrency market. Well I can buy bitcoin ethereum etc. I also bought nVidia. taiwan semiconductor I also bought you know silvergate capital before it had gone on under and I made a 10 x 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 you know, bitcoin miners like clean spark or riot or marathon.

Right? And so you can get you know 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 you know say 5 years or um.

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 you know some meancoin or something like that. Yeah.

01:13:52.59 – Brian David Crane
Um, yeah, it makes sense. What do you think about Google now that they announced their dividend? Did they fall into your income investor bucket?

Income Investments and Portfolio Management

01:13:58.68 – Ryan Coisson
Um, I think they don’t um you know I think it’s interesting that we’re starting to see companies like Google and you know ah meta and stuff paying dividends. Um, it’s a trend that is sort of unsuspected. Um.

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, you know, massive growth. Um, built in so it’ll be interesting. The dividends are far too low to be of interest and 1 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? um 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
Um, 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. Um, that may change in the future. I think you know the first thing I would love for people to do.

01:15:28.97 – Ryan Coisson
Well, the first thing that I would um, recommend people do is to take a moment and actually think about your current financial situation, personal financial situation, business finances, etc and come up with some sort of idea of what they’re wanting to actually accomplish I think that you know. Especially if you’re a bit older and you haven’t done this. You know, in a while. It’s a really really good idea to see where you’re at. You know there was a marketer um, kind of um, disappeared you know 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, yeah.

01:16:06.46 – Ryan Coisson
You know, here’s this legend in space. Yeah, the legend in this space is that you know a big domain or early on bought tons of great domains and sold some of them to really big companies. Um owned a ton of single word domains but he became sort of notorious in our space for. You know, being the first guy to do like a million dollars in one day through an information product and that was the 4 minute and you know John’s story is incredibly interesting to me because I remember you know it was a video of his that I was watching and ah. Maybe he was telling me I hired him for some consulting at 1 point and you know 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 you know like I’m massively in debt I’ve tried all of these ventures. Everything is not working out you know and I mean just credit card bills in a shoebox and he said you know I decided one day to sit down. And just figure out how much of a loser I really am totaled up. You know, pulled out every credit card statement right? totaled up everything that he owned right? and this is again like I think the 90 s um.

01:17:35.82 – Ryan Coisson
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, 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 It’s overwhelming and it’s on my mind all the time and it’s bad right? Then he built a plan right? and and.

01:17:57.72 – Brian David Crane
Yes.

Diversification and Risk Management

01:18:06.58 – Brian David Crane
Um, and it’s bad. Yeah.

01:18:13.42 – Ryan Coisson
Things took off and you know John went on to have a tremendous career and I believe he’s still you know building successful businesses just sort of in private. Um, 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 that’s so important because then you can kind of decide. Well, what do I want to do about this if anything not everybody needs to or or maybe um. You know wants to um I guess needs to is probably the wrong way to say it not everybody wants to most people need to um, but you know if if what I’ve said resonates you know I’m going to be doing a lot more writing and you know releasing trainings and and content on onlineoption.com

People are welcome to kind of follow along. Um you know, um, 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. And learn about what we’re doing. But um, yeah, 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.

Actionable Steps for Financial Stability

01:19:55.88 – Brian David Crane
So I do have 1 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 um. How does this look like you sit down and you go like here’s my here’s my monthly income statement and it’s from your business. It’s from your different investments. It’s 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? yeah you um, you start from what do? 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. Um, you know I think early days for someone who hasn’t really done this kind of stuff before. You know 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 one hundred and eighty 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. You know I live here in Texas at the moment and yeah, everything here is more and more expensive and so but it doesn’t mean that I’m not going to.

Go pay $8 for a matcha latte. I’m still gonna do it seven ninety five. That’s crazy. Um, but ah yeah, so I would start thinking about offense and defense right? and

01:21:50.51 – Brian David Crane
Um, thought what? um is that what matches a lot they cost right now in Austin.

01:22:05.26 – Ryan Coisson
You know 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 about that? Yeah, so you mean that they should set up. Let’s assume they have an llc that they should be doing the Scorp election and paying themselves a salary out of that lllc so that then they can funnel. Ah wow I don’t know if it’s then they can funnel but that way they can fund things like a solo 4 1 k 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 is you want to have some form of whether it’s a solo four zero one k you’re maybe the only person on salary or something like that in that instance, um. And you’re contributing. I think the max for that is like you can do twenty two and a half thousand personally or maybe it’s 23 this year and then the business can contribute you know like forty three 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. You know. Um, 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 $68000 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? ah a 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. Um, but that in and of itself is a huge win.

01:24:06.51 – Brian David Crane
Um, 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. Um. Learning about the markets should probably follow advice from someone like Warren Buffett and just buy the index. Um, and 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. You know I think then think about your actual objective and end goal. This is always the most important thing. Um, 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 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 um 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. Um that I follow and here’s the. 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. Ah, 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 and and and and studying and but than just sitting here trying to read and understand and go oh well. What’s the forward p ratio? What’s this? What’s there where you earn this and you know all 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, yeah, 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 ah, a serial entrepreneur starting new things all the time and you know 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. You know, Um, and again think about you know if you have children. There’s all sorts of things that you can do.

Personal Stories and Entrepreneurial Challenges

01:27:35.41 – Brian David Crane
Yes.

01:27:45.52 – Ryan Coisson
Ah, 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, that’s the.

01:28:03.78 – Ryan Coisson
Um, and just taking yeah, it’s just like little steps moving forward and and you can even go back through I mean I remember at 1 point to go back to John Reese’s story thinking you know how do people get in massive credit card debt right? and. You know 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 you know I was in a really tricky situation. Um, thankfully I got my yeah I got myself out of it. Um, but you know there was a dramatic swing but I think about people who get into these situations and then they just sort of defer Defer Defer Defer I don’t want to look at it I don’t want to.

01:29:05.10 – Brian David Crane
Um, tricky.

01:29:19.24 – Ryan Coisson
Think about it. You know, 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. Ah you know 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 $50000 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. You know so again, my point at sort of sharing that kind of stuff is if you don’t know. Right? What the situation is like, 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. You know 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.

Balancing Business and Personal Life

01:30:46.44 – Brian David Crane
Um, funny. You have a tremendous amount of self-discipline. Yeah, really yeah I think so like what is that? Um, what do I attribute that to?

01:30:48.70 – Ryan Coisson
Maybe.

01:30:58.29 – Ryan Coisson
Um I don’t know um, I did sports so you know I was ah in gymnastics and other sports and did martial arts and you know, kind of a lot of things that required discipline I think growing up. You know some of my heroes. Um, you know, I had a long lineage of family members. You know that those who lived in Europe as well as the US were military folks. You know so there’s obviously that component of discipline a lot of my heroes growing up, you know in the eighty s 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, you know, just air about them this presence of discipline and you watch any of those kinds of old you know, action movies and it was always the leading.

01:31:37.36 – Brian David Crane
Um, 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. Um, 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 ah like an honest assessment of where I was at and I’m I’m paraphrasing I was your story about John Reese which wasn’t you but um, like I looked at it 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 ah yeah, definitely two traits to admire so cool. Thank you Ryan um, yeah, we will put into the show notes.

01:32:28.53 – Ryan Coisson
Um, yes.

01:32:37.36 – Ryan Coisson
Um, 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 try to get the name out there alright cool I’ll talk with you later.

01:32:53.93 – Ryan Coisson
Um, awesome. I appreciate it Man cool. Thanks for having me.