You Have to Be in the Game [Raw Session]

00:00 — Being in it, not just winning

Hey, welcome back to Slow Builds.

So, we all know the saying, like, “You gotta be in it to win it.” And it's one of those sayings that sounds almost too simple, really. You hear it with lotteries, gambling, all kinds of stuff. There are a bunch of versions of it in every form, really. You gotta have your cards on the table. You gotta be in the game. If you're sitting on the sidelines, you're not playing.

But I've been thinking about it lately more because I actually think there's something in there that describes a lot of decisions I've made in my life. Not necessarily the winning parts—more probably the losing parts. And more the being in it part. That's what I believe in.

I think I've always had this thing where, if something genuinely interests me, eventually I'll want to experience it myself. I don't really want to spend ten years standing outside looking at it and wondering what would have happened if I tried that. I hate having regrets. I hate looking back on those things like that—the should'ves and could'ves.

And sometimes it's worked out very well for me. Other times it's cost me money. There are definitely things I did when I was younger that I look at now and think, probably should've done a little more research before I went all in on it. Maybe asked a few more questions. Maybe a little less confident when I didn't actually know what I was doing.

But even with that, I don't think I would want to completely remove that part of myself. Because a lot of what I know now came from actually getting into things, not just reading about them.

01:44 — Starting my first business

One of the bigger examples goes way back to when I started my first business. The company I was working for was basically a sinking ship. We were all losing our jobs, and we all could see the writing on the wall.

And I could see what most people were doing. You start looking around, find another company, get another job in the same industry, same stuff, same group of people, and you just keep moving forward. And there's nothing wrong with that. The stability, that staying in your lane—and that would've been the very safe move.

But there was an opportunity sitting there where a group of us could try something ourselves. And yes, I was naive and young. There was no point looking back now and pretending I had some brilliant business plan and knew exactly where it was all gonna go. I didn't. I knew software, I knew the work, and I knew some people. But actually running a company and finances and travelling and networking and budgeting is a totally different ballgame.

Still, I think it was basic: this company's going to go under anyway. This opportunity is right here in front of me. I can go get another job if I have to. If it fails, no loss. I get another experience under my belt. I got a little leeway before I really need to worry, basically. So why not see what happens?

So we did, and it changed the direction of my life. Not in this clean, straight line either, where I started a company, became successful, and everything worked out. I wish. It was very messy. There were times when I almost lost it. Eventually I had to bring myself back around, and I did okay.

But once I had done that, something changed. When that part of my life ended, getting a normal job wasn't automatically the only option anymore. I had already been self-employed. I've already made money myself. I knew it was possible because I'd actually done it.

So there was this feeling of, I'm already in this game now. Let's see if I can keep playing it. I can still get a better job later—better, I can get another job. I can get a real job. A nine-to-five, or work for a company, work for a corporation.

And eventually I did end up back working for a company in the end. But even that isn't really separate from everything that came before it.

04:01 — What the retail business led to

Years ago, when I also got involved in retail, my wife hated the idea. She wanted nothing to do with it. She's a little more cautious on things, so she's my guardrail. But sometimes I go a little freelance, and I'm hard to contain on that. So we went in on it. And I liked the idea, and we did it.

But retail is a beast that has ups and downs. It's constantly changing. You have a lot of employees, a lot of moving parts, inventory. So basically, in the end, financially, it was an extremely bad move.

But here's where it gets interesting. When you look back over that longer period, that business did last a long time. It kept a lot of people employed. A lot of close family members relied on it. It built a lot of relationships. Obviously, we had to deal with suppliers and customers, and it just kind of fizzled out in the end.

But one of the people I built that business with is connected directly to where I am today. I'm now part owner of the company I'm working with. And that's a relationship that came from us, my retail partner. And we turned that into something else, completely different, in the software world.

That's totally different. And you would never think that when we started a retail company, we would eventually, after losing a lot of money and a lot of headaches, a lot of pain, we would end up creating a software company. And now we're thriving, and we're doing quite well, and I'm just an employee. My wife was an employee, and most of my friends that I've got along the way are employees. So we're all part owners, part employees. So it's very awesome.

But it wasn't a straight line, and there were many downs along the way. But if I wasn't in it, what would have happened, right? And you don't always know what the return's gonna be. Sometimes it isn't the return you were looking for at all.

06:13 — Selling eyelashes with my kid

It doesn't have to be a company either. My kid wanted to sell eyelashes on Amazon, like, not too long ago. So from the retail business, I already had the know-how and the connections for the shipping side of things. So we had to figure out Amazon reselling, dropshipping, Alibaba, marketing, and all the things involved with that.

None of that turned into some massive business, but I got to figure out how those systems work. How do you find a product, fulfilment, what the margins are, how to use Amazon for selling and shipping, and figured out what goes wrong.

But I got to do some of that with my kid, and that's worth something to me. So we had an experience together.

So I think sometimes we look at experiments like that and judge them only by whether they turn into the final thing. If you try dropshipping, you don't build a million-dollar store, apparently it failed. I don't really see it like that.

If I spent an amount I could afford to lose, learned how the thing actually worked, and enjoyed doing it, that wasn't necessarily a waste of time or a waste of money. It might just have been an experiment, a learning experience.

It was definitely something I got to do with my kid, an experience we now share together and look back on fondly. And I know if an opportunity shows up again, I'm not starting at zero. I've touched it before.

07:45 — Investing without betting everything

Investing is another version of this for me. There are stocks I look back over the years and wanted to buy. Netflix was one of those, and I didn't. Other people talked me out of it. Sometimes I talked myself out of it. And looking back, you can drive yourself crazy doing that because, obviously, hindsight makes everything look easy.

I'm not gonna pretend every stock I wanted to buy would have been an amazing winner. There would have been plenty that went the complete opposite direction. I would have lost a lot of money.

But I noticed something about myself from those experiences. If there is something I'm really interested in, I believe there's something happening there, I'd rather have a little bit in it than spend the next decade watching it and wishing I had made the move.

That's different from betting everything on it. Like, I bought SpaceX exposure because I wanna be part of that. I bought Lemonade. There's another space one, Canadian-related, that I've jumped onto because I wanna see where it goes.

And any of them could turn to absolute garbage. I could lose all my money, but I'm in it to see where it goes. I'm in it because I believe in it, and I wanna be a part of it. So that's all I'm saying there. I'm not saying I know where those companies are going, and I'm definitely not saying someone else should go buy them.

The difference now is I have some capital I can allocate to things like that. Twenty-five-year-old me and almost fifty-year-old me aren't playing with the same resources. So the games have changed.

I can have some serious long-term investments, and I can also decide there are a few things where I want some skin in the game, basically, because I'm genuinely interested in seeing where they go. If it fails, I knew that was possible when I went in.

09:37 — Trying Airbnb for myself

That's part of why I'm looking at Airbnb right now. We already own a rental. We're going through a total hassle right now trying to get a tenant out and cleaning up the mess, and we've done it before. So now we're looking at, maybe we just Airbnb it and try to see what happens. And the opportunity's sitting there for us to try right now.

I've always been interested in Airbnb from the technology side, from their growth, their story, everything about it. And so now I wanna be part of the platform, see how the platform works. What makes a place perform better than others? What's the actual experience of running one? Is it worth the extra—is there extra work? Is it worth it?

I can read about it forever, watch YouTube videos, but at some point, if the numbers make enough sense and the downside is something I can handle if it doesn't work, I kinda wanna find out for myself.

Maybe a year from now I'll be sitting here saying Airbnb was a pain, and I should have just rented the place normally. That's possible. But then I'll know. It won't be always looking back and saying, could have and should have. I would have tried it. It would have been an experiment, and either it's gonna work or it's gonna fail. But either way, I know because I lived it, and I did it.

I call these things adventures. Everything to me—life's an adventure. Good or bad, it's an adventure. So it's another story to tell, and that's something I'm putting in the book because I really believe you gotta look at life as an adventure. Because otherwise it can be very depressing.

11:13 — Why I'm finally getting a Tesla

So again, another one like that is Tesla. It's obviously different because that's not—I kinda lost where I was going—it's not a business.

So Tesla's different because I wish—I didn't invest in it back in the day. I invested in it now. I've always wanted one. There was a lot of ups and downs, worry, concerns. But now, you've seen my other videos, I hope. I'm a believer.

There is a future with AI, with autonomous driving, driving becoming a utility, gas, solar, everything you can imagine. I believe it's the obvious winner. I believe it's the obvious choice—or maybe not the winner, but it's the leader of the pack. And I strongly believe that.

So that's why I'm finally gonna get one. That's something I've always wanted for years. I follow the company, follow technology. I watch EVs, keep a close eye on it, and even to the point where I always figured plug-in hybrid is what I wanted. But no, all in, all or nothing, basically.

So I'm getting one, and I'm excited to actually live with one and see what it's like instead of having an opinion just from the outside. That's part of this for me too. Not everything has to turn into money. Sometimes I just want the experience. And fortunately I'm at a point now where I can afford some of those experiences in a way that I couldn't twenty years ago.

Now, side note, I have a sixteen-year-old Jeep, and my wife has a fifteen-year-old Pathfinder, and we have a little tiny horrible car of a Kicks. And so you can tell where I'm going with this. I don't spend money on vehicles.

So to me, buying the Tesla, I do have to replace something. I believe it's a car I will buy that reduces the maintenance, the gas. Obviously, you heard what I drive—not easy on gas. So for me, it's buying something to replace that with little maintenance, but future me. And I want to drive an AI app while it drives me.

So anyway, I digress, and I'll just get back to the script.

13:46 — Learning AI by using it

So AI might be another clear example of me wanting—if you're not in it, you gotta be in it. So I use AI for everything now. Not because I think AI is perfect. The more I use it, the more problems I find with different models and different ways. But I want to understand what the technology actually changes.

I don't think I can really understand that by reading articles all day. I'm a developer. I can actually put the work into it. I can use it in my work. I can build with it. I can use it for writing, planning, research, these videos, automation, whatever I'm doing. Then I can decide where it's useful and where it's nonsense based on actually living with it.

14:28 — What YouTube is giving me

And like I said, YouTube is kind of the same here. This channel is not moving fast. I'm not sitting here pretending it is, but I'm enjoying doing it. I'm learning what it's like to make videos consistently. I'm finding out what I like to talk about.

I'm getting more comfortable. Not really. I waited till my family left to go for a walk so I could do this. Just turning on the camera isn't such a bad idea. It doesn't hurt me so much anymore.

But maybe the channel eventually becomes something a little bit bigger, I hope. But at the rate it's going, I don't think it will. I think it's just gonna be a place for me to vent and speak and put my thoughts out there.

But if I had spent the last year thinking about starting YouTube instead of actually starting it, I would know absolutely nothing more than I did before. Now I know what it feels like, and that matters to me.

15:22 — Can I survive being wrong?

The thing I do think has changed is how I get into these things. When I was younger, I was more naive. Something looked interesting, and sometimes that was enough. Now I'm more critical. I research more. I question things more. I try to understand where the catch is.

What's this going to cost? What happens if I'm wrong? How much time does it actually take? What's the downside that I'm not seeing because I'm excited about the idea? I let things sit a little longer too.

I don't think that makes me less willing to try. Hopefully it just means I'm a little better at deciding what kind of risk I'm taking. Because I don't think the lesson from any of these is that everyone should go take some giant risk. That's not what I'm saying at all.

The way I look at it now is probably closer to this.

I can survive being wrong. If I put money into an investment and it goes to zero, is that going to damage my life? If I try Airbnb and it doesn't work, can I turn the place back into a regular rental, or can I just sell it?

If YouTube never goes anywhere, am I still okay with the hours I spent doing it? Yeah, I think I am, because it's a venting place and just content I can use. I do want to finish my book, so there is content coming from the book into this, into the book. So there's something there.

If I buy something I wanted and it doesn't live up to expectations, can I live with that decision? That's a big one. So I'm more careful what I buy now.

And that's a better question than simply asking whether something's going to work, because I don't know if it's going to work. Nobody does.

16:54 — I'd rather find out

So maybe “You gotta be in it to win it” isn't quite the right way to say it, because winning isn't really what I'm talking about. Some of the things I've been in, I've lost.

I've lost a lot. I lost money. I've wasted a lot of time. I've made a lot of bad decisions, ruined relationships. I've done a lot of stupid, stupid things. There are things I would do completely different now.

But they've also connected me to people, taught me things, opened other opportunities, and given me experiences I wouldn't have had if I stayed on the sidelines. And some of those benefits don't show up until many years later. You may not even notice the building blocks you're laying down, the path you're laying for yourself.

And I think that's the part I've been noticing. Maybe because I am getting older and seeing my decisions now play and come to fruition. I'm still interested in what's next. I'm just a little more careful about how much I'm willing to put on the table.

But if something genuinely interests me, I've done my homework, understand that I could be wrong, and I can afford that downside, I still wanna be in the game. Because I know myself well enough at this point. I'd rather find out.

So, thanks for watching. I hope you liked it. Bye.