Bootstrapped Web

Jordan Gal: 00:09

This is Bootstrap Web episode episode number 66. Welcome back, everybody. This is the podcast for you, the founder, who learns by doing as you bootstrap your business online just like we're doing. Today, we're gonna talk about decision making. The, difficulties, the the tips we've learned along the way, the tricks, some of the intellectual arguments surrounding it.

Jordan Gal: 00:34

It's gonna be good. My name is Jordan as always.

Brian Casel: 00:37

And I am Brian. I am Excellent. I am looking forward to this one. I think it'll be it'll be nice to get back having just an episode where we're, you know, talk through a bunch of stuff. We've had a couple of guests on recently.

Brian Casel: 00:51

We we will have guests on again in in the in the future, but we, you know, we like to mix in these these kind of episodes as well. So, you know, before we jump into our updates this week, I thought we'd just mention one of our newer iTunes reviews.

Jordan Gal: 01:06

Nice.

Brian Casel: 01:07

Got a new one here. This one comes from someone by the name of Sether Zero, he says, or she says, not sure. Essential, applicable, actionable, five stars. As a college student, I'm bombarded with tons of information daily. However, the greatest advice and education I get on a weekly basis doesn't come from the classroom, but the Bootstrapped Web podcast.

Brian Casel: 01:31

Brian and Jordan, thank you for being so willing to share your knowledge and experience with us. Well, thank you for tuning in, and glad to hear this is actually educational and not just two two bozos blabbering on the Internet. But

Jordan Gal: 01:45

Yeah. And good for good for he or she for, you know, getting to the sort of thing back in college. That's a that's a head start

Brian Casel: 01:52

for Mhmm.

Jordan Gal: 01:53

Compared to most people.

Brian Casel: 01:54

Yeah. It it really is amazing, like, how I I really do find podcasts, like, educational if you're if you're looking to get into a new field or a new industry. And not even necessarily just like, here are things I can teach you, but more just like hearing, you know, talking shop. You know, hearing how people talk about stuff in the real world, real practitioners of things, I think it's super important. That's why I love podcasts, love tuning into stuff like this.

Brian Casel: 02:25

So cool.

Jordan Gal: 02:27

Agreed. And today being a bit more of a, let's call it, regular episode, I feel like we haven't done an update in in a while. So why don't we you know, before jumping into the decision making topic, let's give a little bit of an update on us. It's been a while. Mhmm.

Jordan Gal: 02:43

I know I personally have some things that I've kinda kept private for a while that I'm looking forward to sharing. But why don't you kick things off with an update, Brian?

Brian Casel: 02:51

Yeah. I mean, you know, me too. I've I've actually a lot going on on my end right now that, unfortunately, I'm not really in a I can't really share too much of it. I hope I will in the next few weeks. But, you know, like these past few weeks, I it it has been a huge mindset shift for me.

Brian Casel: 03:10

And I'm going through a lot of changes kind of personally and professionally, thinking through a whole lot of things. And that that's a big reason why this episode topic came about today. But, you know, a couple weeks ago, I did talk about that I'm in the process of kind of moving on from from Restaurant Engine in terms of what I'll be focusing on full time. And so at first, you know, about a month or two ago, I was really kind of like urgent urgently looking for new products to to get into, to start building and and and building into the being the next thing. I've kind of put that whole thing on hold, and I'm stepping back from from the whole from that whole process.

Brian Casel: 03:51

And I'm trying to just really just, you know, take some time and space to think through everything and and explore all all the different options. And and I think just to kinda see where where that takes me. And yeah, so that that's kind of where I'm at at from a mindset shift. You know, one thing I I know for sure is I want to be focusing on the audience here and and and the newsletter subscribers. But the other thing I was listening to today was Tropical MBA, as I always do almost every week, their episode two eighty six.

Brian Casel: 04:26

They were talking about it was their comments on Alex Bloomberg's startup podcast. And so this was one of my favorite episodes of of Tropical MBA so far. You know, I I just thought that their thoughts on on the startup podcast were were right on. And it is a really great podcast, that that startup podcast and hearing that story.

Jordan Gal: 04:47

Entertainment wise, it's it's amazing.

Brian Casel: 04:49

It really is. And obviously, you know, Alex Bloomberg, you know, really knows how to produce a well, a well produced podcast for sure. But yeah, like the story, as I was listening through it, you know, getting into the VC stuff and launching this, this his new venture, you know, Gimlet Media, the podcast kind of network that he's starting. There were there were a lot of points in there where I was listening to it, and and I was just really questioning the whole the whole direction. And I and I couldn't I really just couldn't agree more with what Dan and Ian were saying about this in in their episode this week.

Brian Casel: 05:26

So, we'll link that up in the in the show notes.

Jordan Gal: 05:28

Yeah. And a and a lot of it had to do with the default thinking, that was being done by Alex, that that VC was the only path. That if you're gonna do a tech startup, then you have to raise a bunch of money from VCs, and and no other options were discussed. Like, maybe that's for narrative purposes or a a lot of it, I think, comes from the fact that Alex is an employee. Right?

Jordan Gal: 05:54

He's he's worked for someone for a very long time, and I think bootstrapping and the mindset around bootstrapping would be pretty foreign to him. I think it would be more foreign to someone who's been a longtime employee than, hey, I'm gonna do a startup. And that means what I think it means, what I always see and hear about. Yeah. And that means going to raise money.

Brian Casel: 06:15

Yeah. And and, you know, it it it did seem that way. And it seemed like, like the whole idea of bootstrapping or starting small and gaining traction and growing from there, that it at least the way that he told the story in the podcast, it's like almost like that didn't even occur to him, You know? And I think it was like

Jordan Gal: 06:35

not sure if that's right.

Brian Casel: 06:36

Right. Maybe not. But that's how the story came across. And it's almost like, you know, well, I want to start a new company. I want to go out on my own for the first time.

Brian Casel: 06:48

I guess this is what people do. Right? They go get investors and VC. Like, what what else is there? And and I think just that that story or that mentality is so common.

Brian Casel: 06:59

And maybe less so these days, but that's partly because we're we're in this circle of, you know, but

Jordan Gal: 07:07

Unfortunately, with the popularity of this thing, I think it has reinforced very powerfully that exact stereotype and default thinking that when you do a start up, it means this path of VCs and and raising much money. Yeah. The the truth is even even the VC industry is isn't really like that anymore. Now there's a ton more seed stage

Brian Casel: 07:30

Yep.

Jordan Gal: 07:31

And there are smaller amounts of money being put in there first. But it is interesting. I had a conversation with a friend recently who's telling me about trying to raise money for his company and how they made the mistake of starting the business and getting customers. And they said, hey, we're gonna make some progress, and then we're gonna show investors how much progress we made on such a limited budget and limited resources. And the problem with that was the the numbers, the reality got in the way of the pitch.

Jordan Gal: 08:01

So they'd said, we this is how it's been going for six months, and all the investors came back with, well, it's not blowing up, so why should we invest? They really would have been better off like Alex to say, I have an idea. It's going to be huge. Give me money now before the numbers and reality got kinda got in the way.

Brian Casel: 08:18

Yeah.

Jordan Gal: 08:18

So it's it's a tricky thing. Once you enter that world, it's like a a house of mirrors. You know, it's not quite the same type of reality that we deal with where it's, you know, revenue, expenses, profit, can you keep going? How much do you have to reinvest? Like, much more concrete.

Brian Casel: 08:32

Yeah. But I mean, like, when I got into doing products, and I I came at it from a from a freelancer's point of view. I never got into this whole thing as like a dream of starting a business or really being an entrepreneur. It was only in recent years that I kind of started thinking of myself as as an entrepreneur. And, you know, I always looked at it like, look, clients used to pay me for my time.

Brian Casel: 08:55

And, and then it was like, well, let's try to build something that customers would pay for, you know, it that like the whole idea of getting investors and VC and all that stuff, just, I knew it was out there, but it didn't really interest me. And it almost seemed like way over complicated. I, you know, that that's that was my path into all this. I would see guys like like AD and WooThemes and like, oh, I made a made a WordPress theme and sold it and paying customers and Mhmm. And then kinda grow grow from there.

Brian Casel: 09:25

But

Jordan Gal: 09:26

Yeah. That makes sense when you think of it that way. I didn't come from the freelance background into it. But I think I guess, I would say most of the bootstrap community and bootstrap kind of movement and and mindset is from that point of view. And that that makes a lot more sense that someone in that point of view wouldn't say, so I'm gonna stop everything I'm doing.

Jordan Gal: 09:45

I'm gonna stop making income entirely. I'm gonna go raise money for an idea, and then I'm gonna take a salary and be like an employee working with investors and a board of directors. And it's kinda like, that's too too big of a leap. Like, why why would you do that?

Brian Casel: 09:57

Yeah. Exactly. That's that's exactly the mentality that I came at it from. And I and I think you're right. I think a lot of us in this space to it in that direction.

Brian Casel: 10:07

I think that's why we're seeing more and more like we were talking with Rob last week about the growing popularity and the growing community around the idea of micro ISVs, know, bootstrapping a startup, making the transition from a job or from client work into products?

Jordan Gal: 10:27

Right. Well, I would say the majority of people come from that mindset. I I don't, and I know a lot of people I'm agnostic. I just wanna make as much money as I possibly can as quickly as I can with as much freedom as I can. And sometimes those are all intention, but I I always saw bootstrapping as just, like, the logical way to do it.

Jordan Gal: 10:47

Mhmm. It gives you the highest probability of success with the most control, and maybe it's not as potential money as as big of potential money as the VC thing, but it's much more likely. So maybe the expected return is higher. So it's that that that kind of calculation can can lead you to the same place.

Brian Casel: 11:05

Yep. So so what about your update this week?

Jordan Gal: 11:08

Okay. So something I guess I've been kinda sitting on that I felt was necessary to keep private for a long time, and now it's no longer necessary. Right. So I'll I'll back up. In December, so a few months ago now, out of the blue, I get an email saying, hi.

Jordan Gal: 11:31

I'd like to discuss acquiring CartHook. Always a nice email to get. The the x factor was that the email was from someone I recognized, a a relatively well known person in the online space. So I I took it seriously. You know, it was very exciting.

Jordan Gal: 11:51

So that increased and cranked up the intensity of the whole experience, let's say. It made things much more real, and it kinda made me perk up and pay attention and relook at Cardhook, as maybe maybe a bigger opportunity than than I was thinking. So the acquisition didn't work out for a number of reasons, that I don't think is appropriate to get all the way into, but it it didn't it didn't make sense at the end of the day. We decided to keep to go our own ways and kinda wish each other luck, very friendly. It was it was actually a great experience all the way around.

Jordan Gal: 12:32

I came away with it with more respect for the person than before, so it was it was a great experience that way. But what that did is it it heightened expectations. And so once the once the the the decision was made to not do it and go our own separate ways, it almost left like this void of, wait a minute. I thought maybe this thing was gonna go one direction. Right?

Jordan Gal: 12:55

You can't let that influence that kind of a decision. It didn't make sense. And so just because the excitement was there, didn't make sense to just subordinate the business decision to the excitement, which was fine. I felt that that was the appropriate

Brian Casel: 13:09

Right. Because when you're when you're envisioning the the first option, like the the acquisition, all of a sudden, you know, I I mean, the vision becomes something different. But but then once that that is now off the table, it's like, alright. Well, how do we recreate that same sort of end vision given the new given the current direction?

Jordan Gal: 13:28

Exactly right. Going right back to the way I was doing things before almost seemed unreasonable. Like, so I'm just gonna take whatever expectations and excitement ahead and just kinda go right back to keeping it on the side and a nice slow burn and doing some consulting and maybe some info products and that sort of thing. So that's that's kind of the explanation, one of the explanations for going all in on card hook. Right?

Jordan Gal: 13:53

That's not the explanation. It's just it was one of the original triggers that said, wait a minute. Maybe this thing is a bigger opportunity than I am giving credit for. Let me relook at it again. And then that's that's what helped make the decision to say, you know what?

Jordan Gal: 14:08

In 2015, let's just go all the way in. Let's go all in on Cardhook. With that void being there of excitement, I guess, I don't know if you wanna call it luck. It's not luck. What what happened was I recently brought in a new cofounder, a partner.

Jordan Gal: 14:27

And I talked about that a little bit, but this is all part of the same story. A few weeks after we decided to go our own ways, the potential acquirer and I, I got a random opt in to the lead magnet on karthook.com. But I am, I guess, aggressively minded, and this is where the part where luck leaves and action takes over. I saw someone sign up. I looked them up.

Jordan Gal: 14:58

I went to LinkedIn. I went to their Twitter profile. Turns out they work with like with like a venture development fund in New York. So these are like these these shops that are popping up in in like New York and San Francisco in these markets that that help groom and prepare companies to go the VC route. So at the very least, said, you know what?

Jordan Gal: 15:20

That's interesting. Let me reach out to this person. So I reached out to them on Twitter and said, hey, I saw you signed up. I saw you work for this cool looking company. You know, what's the deal?

Jordan Gal: 15:28

Do you wanna talk? They came back to me and said, actually, it's not about me. It's about my, you know, my my superior, my my boss who asked me to look into things. I said, alright. Cool.

Jordan Gal: 15:40

Let's let's dig further into this. Another few days led to someone else signing up for the lead magnet, and I saw that they were linked to them on Twitter and on LinkedIn. I said, wait a minute. This is all a conspiracy. Something's happening behind the scenes.

Jordan Gal: 15:56

People are talking about me. I need to get involved in this and see see what's going on. So that's when I kind of more aggressively pursued and said, look. Let's let's talk. That is how I found my cofounder.

Jordan Gal: 16:10

So he opted in. Someone opted in, then told him about Cardhook from the Mixergy interview, the the the the sixty minutes that changed my life essentially. Everything comes out of that Mixergy interview, more or less.

Brian Casel: 16:26

I you know, you you you told me about the about meeting the cofounder and everything, but I I didn't realize that's actually how the dots were connected.

Jordan Gal: 16:34

Oh, Somebody signs up for the lead magnet, and and Jordan Gahl is not messing around.

Brian Casel: 16:39

Yeah. And I I wanted to clarify something. So about your lead magnet Mhmm. You're like, currently, your your current marketing strategies, you're not, like, driving a a whole ton of traffic at the lead magnet. And that's why Barely.

Brian Casel: 16:53

Every few sign ups for the lead magnet are, you know, they're popping up and you're able to kind of look into them individually. Right?

Jordan Gal: 17:00

Yeah. I get a few sometimes I'll get a few in a day, then I'll have a few that go without it. Yeah. But I'm not driving traffic to the marketing site. That's not the strategy right now.

Jordan Gal: 17:07

It's all about, like, outbound and and whatever else. But people who see the Mixergy interview go to the site.

Brian Casel: 17:13

Yeah. And and that is a you know, just to sidebar from from your story here. Right. Those of you who are starting something new and very low traffic, you get a a couple of of opt ins, a handful of opt ins. I mean, look what you can do.

Brian Casel: 17:30

Look what look what you can make happen with just an email address. You know? You you don't have to think Aggressively. Don't don't think in thousands. And and if you're not getting thousands of subscribers, things aren't happening.

Brian Casel: 17:42

You know? Start googling. Start digging into each and every Yeah. Every one of those first few opt ins, and who knows what can happen, you know?

Jordan Gal: 17:49

Yeah. And don't think in terms of the Internet and email and Twitter. Like, business happens in the real world. So make things appear, make things transfer from online to the real world whenever you possibly can. So that's that's what I did.

Jordan Gal: 18:06

So I kind of pursued this and figured out exactly who it was and everything, and I said, look, let's get on the phone. So that was the first time I spoke with my cofounder after that. His name is Ben Fisher. He's done a few really, really cool companies. He used to be in in ad, like, ad tech, so, like, advertising technology and advertising companies.

Jordan Gal: 18:29

He's got a design background. He's a developer. He built a company called called Alchemy. He started a lean startup machine. Just a bunch of cool stuff.

Jordan Gal: 18:37

He's a New York guy. So it turns out he's, like, look been looking into ecommerce for a while. So we got on the phone and just hit it off for, like, an hour and a half conversation about ecommerce, about SaaS, about just the mindset behind this business, and all these things that go into it. So then we basically said, cool. Great to meet you.

Jordan Gal: 18:56

Let's, you know, let's see what happens. Let's be in touch. So I had I had the feeling like this is this is supposed to work out. Like, this weird email opt in Twitter, like, roundabout thing, and then all of a sudden, I get on the phone and hit it off with this guy. Our skills are perfectly complementary.

Jordan Gal: 19:16

I was I was like, this is this is something. This is worth pursuing.

Brian Casel: 19:20

So But how how was he connected to the first per the from the He

Jordan Gal: 19:24

was a friend.

Brian Casel: 19:25

Okay.

Jordan Gal: 19:26

He's a friend in New York, and the friend that first opted in and saw the Mixergy interview and all that knew that Ben was looking into the e commerce world in general. And so he said, hey, Ben, you should check check this guy out. Gotcha. I just watched his interview. I checked out the site.

Jordan Gal: 19:41

So that's like a day later. That's when that's why he up. Mhmm. So the day after we get on our first phone our first phone call, I, like, I threw out the Hail Mary. I was like, look, this might be weird, but I feel like, you know, this is this weird fate thing.

Jordan Gal: 19:56

Like, this is supposed to work out. Let's let's get back on the phone next week. So we got on the phone again, hit it off again for another hour. It's like dating. This is like, oh, it's so exciting and Yep.

Jordan Gal: 20:05

You know. We're completing entire Oh, yeah. Exactly. So then

Brian Casel: 20:13

I

Jordan Gal: 20:13

just went full I went full bore aggressive. After that second phone call, I was like, look, man. Let's not waste each other's time. Let's see if this is for real or for not. Like, is this is this love or is this fantasy, you know?

Jordan Gal: 20:26

So he happened to be in in LA, and I was like, look, man. I'm gonna come down there. I'm gonna fly to LA. We're gonna work together for a few days. We'll see how we'll see how it goes.

Jordan Gal: 20:37

He was like, alright. If you're willing to do it, you know, I showed I showed a level of seriousness that that that commanded a serious response. Mhmm. Right? I was, look, I'm gonna drop down 500, get on a flight from Portland down to LA.

Jordan Gal: 20:52

I'm gonna not hang out with my kids and my wife, and I'm gonna come hang out with you, and we're gonna talk business. We're gonna work together. And he was like, alright. If you if you wanna come down here, then then let's do it. That went well.

Jordan Gal: 21:04

And so the next step was him showing the love back. He was like, alright. I'm gonna come to Portland. So he he did the same thing. So two weeks later, he came up to Portland.

Jordan Gal: 21:16

We worked together again for another few days. And that's when things started to get you know, nothing's a 100% easy. So he and my original cofounder, Charlie, the original developer, you know, how you get two developers working together. It's it's never straightforward.

Brian Casel: 21:32

Yeah. But now it just so I'm clear, Charlie, you're the original cofounder, from what I understand, he has kind of been out of the picture more recent in in recent months. Right? Like like He's out of the picture, but, like, he was working at a job and

Jordan Gal: 21:46

Oh, yeah. He's had a full time job for for a long time. Never out of the picture. It just it goes in waves.

Brian Casel: 21:53

I I guess, I mean, from, like, a day to day operations, like, together standpoint.

Jordan Gal: 21:59

It's pretty consistent. It's just that it goes through a quiet periods where it's like, hey. I need this or

Brian Casel: 22:04

Oh, okay.

Jordan Gal: 22:04

I have an issue with that. Yeah, he just kinda I mean, he he works hard. He works nights. He works weekends. Yeah.

Jordan Gal: 22:09

It's it's a complicated product, and and he does everything. He does hosting, databases, front end, back end, tracker, JavaScript, PHP. You know, he he has done everything, which is ridiculous. So so that's when things started to get kinda real when Ben was up here in Portland. And so, we needed to figure out a way to work together, and that's kinda what's been happening over the the past few weeks.

Jordan Gal: 22:38

And I kinda had to play, like, dad a little bit. Like, listen, developer one, developer two. You guys are smarter than I am. You guys are both of of equal caliber. Like, let's get me out of the way so you two can realize that working together is gonna be phenomenal instead of one of you guys having to do this or having to do that.

Jordan Gal: 22:55

Once we got over that initial hurdle, that's kind of where we've been over the past few weeks. And then, yeah, things things went from flirting to to dating, and and recently, we got we got married. Congratulations. We had thank you very much. Appreciate that.

Jordan Gal: 23:12

So we got we got the lawyers. We got the legal side of things done and drafted and signed and negotiated. And now, you know, now we have three cofounders, and that has changed everything.

Brian Casel: 23:25

Mhmm.

Jordan Gal: 23:26

Changed the mindset, changed the the game plan, the expectations, the potential. So that's it's unbelievably exciting. And it it's you know, money is, like, the point of business, but but there's a lot that goes on beyond that, even cynical. You know, I I can admit that. Two years ago, when I had the idea and was sitting with Charlie in a coffee shop, asking him if he was kinda crazy enough to to do this with me, it was amazing to get him on board and working together.

Jordan Gal: 24:03

And to go from there to now having, myself work on it full time, another very high caliber person working on it full time. We got this sales consultant who's working on it a lot. We've got outsourced people working full time on it. Charlie working part time. It's like all of a sudden, it's like this thing that lives Yeah.

Jordan Gal: 24:23

And and and has momentum.

Brian Casel: 24:25

It's really exciting, man. I mean, to, you know, to see the progress you've made over the last two years has been absolutely awesome. And, yeah, like you said, like, it's now here we are. It's like a real thing. And, you know, you're full time focused in 2015.

Brian Casel: 24:39

So, yeah, exciting stuff for sure.

Jordan Gal: 24:42

Yeah. So I'm happy to just be able to share it. And I think there are lessons throughout there that I don't need to, like, point out or dissect. I think the main theme is, you know, don't wait for things to come to you, man. Go go get them.

Brian Casel: 24:55

Yeah. Make them happen. For sure.

Jordan Gal: 24:56

Yep. Cool, man. So let's let's jump into the episode.

Brian Casel: 25:00

Yep. Topic I decision think that a lot of what you just shared there, a lot of what's kind of going on with me has really prompted this episode, which is about making decisions. And like you said, I mean, in the story you just shared, there were a number of decisions that you made along the way, whether it was getting on the phone with the guy flying down to LA.

Jordan Gal: 25:26

Saying no to the acquisition.

Brian Casel: 25:28

Yeah, saying no to the acquisition. Every one of those.

Jordan Gal: 25:31

How much how much equity to give? These, you know, these Yeah.

Brian Casel: 25:34

You know, the partnership scale, all that. So, like, every every one of those decisions, I'm sure, know, you I mean, we were talking about them as they were happening. Like, you went back and forth and weighing different options and, you know, what ifs, the pros and cons, like playing out different scenarios. You can do this all day, all week, all month, and all year long. But at the at a certain point, you have to decide one way or the other.

Brian Casel: 26:00

And otherwise, everything else is going to suffer until the decision is made. And so that is something that I've really been thinking heavily about these past few weeks because I personally made some very big decisions and and I'm still making decisions right now. And it's been it's been tough, but but you know, something that I was listening to about about three or four weeks ago, I was tuning into Amy Porterfield's podcast, which is called Online Marketing Made Easy. And it was her episode number 47 where she was interviewing her business coach, Todd Herman. And they were taking listener questions.

Brian Casel: 26:40

And one of the questions was, how can I overcome the fear of failure that constantly prevents me from making decisions? And it was like, somebody asked this question and I was like, you know, they must have been reading my mind because I'm every time I have decision, I'm I'm always faced with that fear of like, what if I make the wrong decision? Is is this gonna set me back? Am I gonna regret this? You know?

Brian Casel: 27:04

And all those things that go along with that. So Todd's answer made me kind of rethink this whole thing. And here's what it said. And I'm kind of paraphrasing this. This isn't his exact words, but this is basically what he was saying there.

Brian Casel: 27:21

He was saying the most successful people are eager to make as many decisions as possible every single day. And they're eager to make those decisions as quickly as possible, given the information that they're faced with in the moment. So they're not afraid to make the wrong decision. In fact, they want to make some they want some of those decisions to be wrong. And the reason is that because the reason for that is that they would result in learning opportunities.

Brian Casel: 27:48

And the more wrong decisions that a person can make, that actually makes them smarter and wiser, and it makes them better at making more decisions in the future. And it helps them make those decisions faster, you know, just simply from the fact of making a lot of decisions. And, you know, he he went on to say that there's this common misconception where if you give more time to a decision, then that's going to reveal more information and bring more things to light, and that's gonna help you find the right answer. Just if you just give it another day or another week to kind of, you know, debate back and forth. But that thinking is wrong.

Brian Casel: 28:32

And so we make our best decisions based on our past experiences. And so we're much better off just deciding one way or the other than doing that quickly using whatever information we happen to have at the moment, understanding that we probably don't have all the information, but just go with whatever you have in front of you, make a decision one way or the other. Because the right decision is always going to be based on your past experience, whether that's experience from things that have gone right or experience that from things that have gone wrong. That's gonna you know, I think this plays back into like trusting your gut. Like your gut is always going to your gut reaction on anything has a lot of wisdom baked into it just from your living your life and and and your past experience.

Jordan Gal: 29:21

Yeah. Even if you're not conscious of it. Yep. Sure. Reminds me of, like, multiple choice exams in high school.

Brian Casel: 29:28

Yes.

Jordan Gal: 29:29

Right? Like, your your your first instinct is usually the right one as opposed to overthinking it. You know, that now it applies to more complex decisions, but doesn't necessarily mean it changes the structure of the getting to the right answer.

Brian Casel: 29:42

Yeah. Absolutely. So you brought up another another link. What was that?

Jordan Gal: 29:48

So it's it's it's related. Right? And, yeah, this is it's a tricky topic because it's hard to train yourself. It's hard to change the way you normally do these things. Right?

Jordan Gal: 30:04

If you're just someone who likes to sleep on it, who likes to take the extra time, it's very difficult to force yourself to make decisions more quickly. I think it's a it's a struggle for most people. There are those people out there that are just super proactive and super decisive. I know personally I'm not that decisive. That's my instinct is not to just bang, make the decision very, very quickly.

Jordan Gal: 30:31

But over time, you do realize that taking additional time, it just costs time more than anything.

Brian Casel: 30:36

It it

Jordan Gal: 30:36

does not necessarily lead to a better answer. And when you brought that up, it it it brought to mind an article I read. I don't know where I found it's an article from 2007. This is from Marc Andreessen, and he's talking about age and the entrepreneur. Basically, when is the ideal age for an entrepreneur to maximize their, you know, their success rate or are younger entrepreneurs better because they're more risk loving or older because they're more experienced.

Jordan Gal: 31:08

And so there's a lot of studies that go around, not just entrepreneurship, but, like, creative output, whether that is art or math formulas or achievement of some type. So in the article, he talks about these these studies and how one of the more interesting conclusions, is that the quality of what you put out there, whether that's business, art, science, whatever it is, it doesn't really it doesn't vary nearly as much by age as as we think. And because of that right? Let me let me just read his his little piece on it. Mhmm.

Jordan Gal: 31:47

Quality of output does not vary by age, which means, of course, that attempting to improve your batting average of hits versus misses is a waste of time as you progress through a creative career. Instead, you should just focus on more at bats, meaning more output. So in our in our situation, it's more decisions, more businesses, more projects, more things launched, and trying to focus on improving your in this, he calls it your batting average, meaning how good you are at something. Like, if you're an artist and right. The analogy is if you're an artist that paints, you're much better off not spending an enormous amount of time on each painting, expecting to get better, and that your next painting will be amazing because you just spent so much time learning.

Jordan Gal: 32:38

The analogy is really just keep painting. Yeah. And and if you have 10 pieces of output and two of them are brilliant, you the same thing would have happened if you had a 100 outputs. 20 of them would have been fantastic. It doesn't really matter that over time your career changes.

Jordan Gal: 32:59

It's that you're kinda capable of what you're capable of, so you're really better off trying to put out there a 100 businesses, a 100 pieces of art, a 100 paintings, and having 20 great ones instead of trying to really focus hard on getting better at this decision and getting more information and testing and figuring out and surveying your customers. And you're really much better off launching more marketing campaigns and more ads and more products. So it's tied. It's what it is, it's it's it's proof that you should make decisions quickly because that will most likely lead to better outcomes.

Brian Casel: 33:33

Totally. And I I think anyone, you know, kind of creative creative minded creative minded can can really relate to that analogy there, you know, because I I like, I was listening yesterday to to a podcast about about music production and and composers. I, you know, I'm I'm still kind of involved in that world as well. And the guy was saying, you know, he was he was saying that that he he tries to write a new a new song, you know, to be used somewhere, like, every day. And like last week, he he created one that was just killer, like like out of the park, you know, really worked for the application that he was that he was writing for.

Brian Casel: 34:13

And then the next day, it was like crap. And at that point, you know, you can like totally psych yourself out, You know, by like, you know, how could I not match the quality that I did yesterday, but you have to go into it thinking like every day, if you're just creating, you know, you're still going to have this more or less the same batting average, you know, you're still, you know, you have to go into it knowing it it there there's power in numbers even even in in, like, creative, you know, output.

Jordan Gal: 34:45

I agree. There's there's a tension, though. If you think about your own career, I I have I have launched a relatively high number of different businesses since I started. Right? Since I left the investment banking world, I probably put out there, I don't know, eight or 10, like, actual business attempts.

Jordan Gal: 35:07

The the the problem is I see how, call it, two or three of those can be called moderate successes. The but the issue is I always feel like the next one, it's gonna be better than the previous ones. Like, I just learned all these painful mistakes, all these issues, all these different you do learn over time. Yeah. It's I guess what it what it is, it's it's a problem of surrendering to fate and saying, I'm just gonna try my hardest.

Jordan Gal: 35:37

I don't actually have that much control over this next business being a success. I just have to trust that I am learning along the way, but it's not guaranteed to be better than the previous ones.

Brian Casel: 35:48

Yeah.

Jordan Gal: 35:48

But If it doesn't work out, move on and launch another one. That one has a better offer.

Brian Casel: 35:52

And I think this gets back into, like, patience with the whole idea of making progress over a long extended period of time. Right? Like the like a batting average analogy. Right? I mean, a hitter will, you know, over time get better until they get past their prime or whatever.

Brian Casel: 36:09

But like the as they're getting better, as they're learning the game, as they're progressing in the game, they're gonna get incrementally better, like, one season to the next season to the next season. But they're not gonna get better exactly one day to the next day to the next day. The, you know, the the increase in the batting average is only gonna happen after a 162 games. You know? So you have to go into it like there

Jordan Gal: 36:31

I know who who has the patience.

Brian Casel: 36:33

Right. You know? And and and it I I think these number it's a numbers game on, like, so many levels. Right? Like, you you might try three different marketing campaigns this month and and see incremental progress, or you might start three different businesses over the course of five years and and two two might work out and one not.

Brian Casel: 36:51

You know? Right.

Jordan Gal: 36:52

It's it's easy to, you know, have a different AdWords campaign and say, oh, it's a numbers game. It's it's returning x amount, so let's let it run. Who cares? When it's like years of your life on a business, it's much harder to have patience. So it's it's almost like that's, like, too big.

Brian Casel: 37:08

Yeah.

Jordan Gal: 37:09

I think where this is more useful, like that, you can acknowledge as true in your career, and you can't really act on it. Can, like, oh, if this if this one's a failure and I chalk up these eighteen months to, you know, whoops, it didn't work out, the next one will be better. That's that's, like, too hard. But but where you can apply it is when something comes across your desk and you have to make a decision, whether it's, should I hire this intern or not? Should I work with this person?

Jordan Gal: 37:39

Should I hire this person to redo my marketing site? You know, right now, redoing the marketing site. Good example. I don't know what the right message is. It's a guess.

Jordan Gal: 37:48

Mhmm. I could spend weeks on it and say, I'm gonna get it right. I'm gonna serve in my customers. I'm gonna call everyone. And, yes, you should do some of that.

Jordan Gal: 37:57

But at some point, you have to just make a decision. The the truth is I would have been better off a month ago just going with what my gut was at the time with the information that I had at the time, and right now have a marketing site that's new with one specific message and then start getting feedback on it.

Brian Casel: 38:15

Right.

Jordan Gal: 38:16

And Right. That's what Rob did with with the trip. He was like, I didn't have it right. Oh, no. Not Rob.

Jordan Gal: 38:20

I'm sorry. Nathan Barry with ConvertKit, that great post he just put Yeah.

Brian Casel: 38:24

That was good.

Jordan Gal: 38:25

On on how to get to five K. He had it completely wrong. And he learned that only because he just launched with a with a guess and then heard back.

Brian Casel: 38:34

Right. And I wouldn't say he had it completely wrong either. I would say that's Off. That's what this is. That's what building a SaaS app is.

Brian Casel: 38:41

It takes so much time and so much trial and error. Nobody gets it right with the gradual increase. There's no hockey stick growth. We all know that. But even the gradual increase in growth doesn't happen overnight.

Brian Casel: 38:56

It takes so much trial and learning and making a lot of decisions and making a lot of mistakes before you can get to the stuff that works. Yeah. Yeah. So, know, one thing that I've been thinking a lot about lately is this idea of like, as we go forward in business and getting more experience and doing more things and making more decisions, do we actually get better at decision making? Or not necessarily get better or worse, but like is it easier or is it harder as we go on?

Brian Casel: 39:29

And I'm starting to feel right now that it's getting harder for me the longer I've been at this. I don't know if that's a maybe the fact that I'm getting a little bit older, have a family now, have a little bit more on the line than I did back in my 20s, know, that could play into But

Jordan Gal: 39:49

I think that's the big contributor.

Brian Casel: 39:51

Yeah. I think so too. I think another one though is that and this is probably the the less healthy contributor is that I look back on a lot a lot of decisions that I made in the last couple of years. And I've done a lot of good a lot of things that I am very proud of. And and I learned a lot of lessons the hard way, which I'm proud of those lessons as well.

Brian Casel: 40:12

But there are decisions that I can look back on and and say, I I made the wrong call there, and I can see what it cost me. Like, it cost me this many months of of a setback or something like that. You know. And and, you know, you can't dwell on that stuff, but but it's hard not to. But it at know, when I'm faced with a new decision with very similar things at stake, it's it's it's hard to take these decisions lightly now.

Brian Casel: 40:39

Whereas a couple years ago, I would have just said, fuck it. Let's just go with this and do it.

Jordan Gal: 40:44

You know? Yep. Yep. I yeah. I think both of those play into it.

Jordan Gal: 40:49

Past regrets, which we all have a healthy sized mountain in in back of us of, and the stakes being higher. You know, sometimes I feel like, some people I know who are, I don't know how to say this, less introspective. Right? They they they they're not any less smart. They just think about this stuff less.

Jordan Gal: 41:12

They're just more okay with just making decision moving forward. Mhmm. You know, and and sometimes you'll see you'll see successful people that way that they they don't dwell on past mistakes, and their their ego and their confidence just kinda stays consistent, and they just barrel through a lot of things that leaves other people scratching their heads. Like, how do they have the balls to do that? Yeah.

Jordan Gal: 41:36

It's also when the stakes get raised and you have a family and all that, and that's why I tried really hard to to become financially successful before having a wife and kids because I knew that doing that ahead of time would free you up. It'd give you more freedom and be able to take more risk, and, I was not able to do that. So it's it's harder when the stakes are raised.

Brian Casel: 42:02

Yeah. It is. And and I look back on the when I I made the decision to quit my job and become a freelance web designer. And I remember the the main justification I had for that at the time was, well, I'm single. I don't have a mortgage to pay.

Brian Casel: 42:16

If I'm gonna do this thing, I'm gonna do it now. And that's what I was telling my parents at the time. That's what I

Jordan Gal: 42:20

was What's telling my the downside?

Brian Casel: 42:22

Like, what's the downside, you know?

Jordan Gal: 42:23

Do it for a year at worst, move back into your parents' house for a few months and kind of get a job. Yeah, exactly. That's not that bad.

Brian Casel: 42:28

And now I feel like, you know, I don't have those same excuses anymore. But but I still wanna but I still wanna take the same kind of risks.

Jordan Gal: 42:39

Well, that's the that's the that's the the danger is that not only are you more careful in your decision making to a fault and you're more risk averse. So it's like not only are the decisions more important and have a bigger downside, you're also making worse decisions because you're, you know, you're scared and you're constrained and you're worried about this and you're looking at past regrets. It's a really hard thing to kind of get over. I think a lot of people struggle with this, and it's easy to envy people who at least appear to be making more decisions more quickly with less worry about the downside.

Brian Casel: 43:23

Yeah. But I think like with anything else, there is a balance. It does depend on what type of decision it is understanding what's at stake. You don't want to go into things blindly, and you do want to give things a certain amount of time. So I also kind of put together a couple of tips that I've been thinking about lately.

Brian Casel: 43:44

And just trying to these are things that I've been trying to change in in my approach to making decisions more recently. So, you know, one is asking for advice from advisors. And this is something that I've been that I think I mentioned around the turn of the year when we when we talked about like goals for this year or things that we want to improve. I feel like in recent years, I really only relied on myself or or didn't even share a lot of what I was thinking about with the people around me. And now I'm I'm making a conscious effort to try to just ask for advice, not be afraid to ask for advice from people.

Brian Casel: 44:25

And so I'm talking about like advisors like within in the mastermind groups, friend, you know, friends who who do this type of stuff for a living really help. But also other friends and and family, even people who don't aren't necessarily entrepreneurs or, you know, know this this field and whatnot, but they know you. They you know, they're they're close to you. And then and then they can give you feedback in different ways. So, you know, I've been asking my wife for plenty of advice, my parents, my brother, you know, there are there's a lot of value in just running running through the thought process and the things at stake and kind of explaining what's going on and just keep And saying it out loud.

Brian Casel: 45:09

Yeah. Saying out saying it out loud and and getting their take and their feedback on it, But

Jordan Gal: 45:14

Seeing their responses to what you're saying, like their Yeah.

Brian Casel: 45:17

Yeah. Their instinct. Yeah. Their gut instinct. I I think the big but here, though, is that it's too much to ask them, what should I do?

Brian Casel: 45:27

Like, it's not their place to tell you what to do. And that goes for advisors, friends, family, everyone. Their their only role in this is to kinda give you feedback and support you in your decision. You know, and I'm starting to really learn that. Because it's too much to ask, and it's not the right thing to ask someone, like to have that sort of responsibility for you.

Brian Casel: 45:51

And nobody wants to tell you what to do or what not to do, you know. And honestly, like at the end of the day, it's it's it's your decision to make, and you can only go on on on the things that that you know. But the feedback that you get, you know, just people telling you, well, you know, it sounds like you're you're saying this, and these are the things that I know about you. So that's what I'm hearing you say. That kind of feedback can be really valuable as you're trying to go through these big decisions.

Jordan Gal: 46:23

Yeah. I I like to listen to myself in those situations. Like, as I'm coming to someone for advice, let's say, I'm coming to my wife and saying, hey, should I right. Let's say the acquisition was a big decision. I I would listen to myself in which side of the decision I was defending.

Jordan Gal: 46:41

Mhmm. Right? So you're, talking to someone, you're like, yeah. But this and this is good about this side of the decision, but then there's this downside. But then on the other side, there's always something wrong with the with the other decision also.

Jordan Gal: 46:54

Right? So you can you're making these arguments to yourself, but you hear your bias and, like, which one you're defending a little bit more and which one you're just kind of throwing out there, which one you're positioning in a better light than the other. Exactly. Exactly. The bias that comes through in the way you describe it is like, that's where my gut is.

Brian Casel: 47:13

And very often, I've seen this happen a number of times, is the feedback that you get from someone as you run it by them. Typically, it's something along the lines of, well, as you're describing it, I can I can hear your your decision is already made, and it sounds like you're coming to me for permission to to take option a instead of option b? And that kind of reaction is telling in itself.

Jordan Gal: 47:40

That's an honest friend or mentor.

Brian Casel: 47:45

Another idea that I've been thinking of lately is just set a deadline. Just a little tip for you know, you you know you have this decision to make. You know you can't move forward. You can't start executing on any any sort of plan until some kind of strategic decision is made. So you gotta just say, alright.

Brian Casel: 48:02

This Friday, I'm gonna decide one way or the other.

Jordan Gal: 48:05

Mhmm. You know? I think that's very healthy. I have horrible discipline. And so what I do is I set a deadline with somebody else.

Jordan Gal: 48:13

And that that's one of the things that having a cofounder working on this full time with me has improved productivity. Because when I say, I'm going to get you x by Thursday

Brian Casel: 48:24

Right.

Jordan Gal: 48:24

There are a lot of micro decisions around producing x. Like, I will get you the copy for the new marketing site by Thursday. There are so many decisions that need to be made about what headline, what structure, what pricing page, what and the deadline just forces you to make all these decisions more rapidly because, like, I have to get this Google Doc shared by Thursday, or or I'm a Slacker. I didn't do what I said I was gonna do. But it helps, like, steamroll right over a lot a lot of the difficult decisions.

Brian Casel: 48:53

Yeah. Absolutely. Two more kinda quick ones here. You know, just remember the upside of making a wrong decision. So as you're as you're weighing, you know, the pros and cons and the different scenarios of like option a versus option b, just remember that you can go into this decision knowing that you maybe it's like a fifty fifty chance that you'll make the wrong decision on this one.

Brian Casel: 49:16

But even if you do, there there there's an upside to that because you're gonna learn a very hard you're gonna learn a really good lesson that that you can take with you into the next thing. And I think this comes back to I in many times in in my career so far, I've had this mentality of I just wanna get to the first try so that I can screw up a lot of things and then get to the second try. Because I know the first thing is not going to work out. And I think part of that relates to making decisions because, know, in general, you might be like fiftyfifty or whatever. You're going to make wrong decisions.

Brian Casel: 49:52

You have to go in knowing that and just expect to to learn some lessons from it.

Jordan Gal: 49:58

I think the the hard thing with with this piece of it, like focusing on, look, what's the worst that can happen? You know, you make a bad decision, you learn. The Where it becomes difficult is people convince themselves, myself included, that they can't go back, that this is a final decision. Mhmm. That if they make this decision, then they can't go back on it, they can't change it, which is almost never right.

Jordan Gal: 50:24

If I decided to change my pricing completely and change the marketing site and put it out there and I mean, no one no one knows. No one cares. You know? The audiences are so small. The it's not like the Wall Street Journal is gonna say, oh, card hook chain went back to their original pricing.

Jordan Gal: 50:42

Like, nobody nobody cares. You can make these mistakes and just go right back on

Brian Casel: 50:48

them. Yeah. Exactly.

Jordan Gal: 50:49

No no one will even notice.

Brian Casel: 50:50

Very, very, very few things are irreversible. Right? And I think the thing that we risk though is time. Like how much time is the wrong decision going to set me back here? And again, it's just not something that you really have control over.

Brian Casel: 51:06

You have to at the end of the day, make a decision one way or the other and accept that, yeah, it might result in a setback, but that setback also results in a huge lesson that you're going to be faced with the same decision again at some point. Brings it sooner. And at that point, you're going to work off of much better information, you know, because we always learn from our experience. The last one that I had here, and I guess we've kind of touched on this quite a bit is trust your gut, you know, and I was talking to a friend yesterday, explaining, asking for advice, explaining what I'm faced with and what I'm trying to figure out. And he told me, you know, he he asked me, listen, that so this question has helped me in the past.

Brian Casel: 51:51

And that is, you have a gun to your head. You you have to decide one way or the other right now. What is it? And that that question usually just brings the right answer immediately forward. Because that's what your gut is.

Brian Casel: 52:07

What is your gut telling you? You're leaning one way or just the right now. And that doesn't necessarily mean that you have to commit to that decision today. Maybe you still want to give it another day or two or something like that. But at least just asking that question tells you exactly, all right, I know where my gut is.

Jordan Gal: 52:27

Yeah. I think that's like the ultimate you know, at some point, whatever, if it's gonna be a deadline, asking people, worrying about this, at some point, that question needs to be addressed, and that that's probably what you should do. And don't worry about the consequences and this and that, and it's irreversible. I think we would all be better off if we if we ask ourselves that question. A lot of decisions, the things that stay on your to do list for, you know, two months, just what would you do if someone put a gun to your head right now?

Jordan Gal: 53:01

Just say the answer right now. And you're probably better off doing that today or tomorrow as opposed to waiting another month until you make the decision.

Brian Casel: 53:07

Yep. Absolutely.

Jordan Gal: 53:09

I'm gonna listen to this podcast a few times to take our own advice.

Brian Casel: 53:13

Yeah. Yeah. Me too. And and, you know, the other I guess, like, one more one more quick one that I just thought of is is the journal. And I I forgot how how much I I personally rely on this, especially in recent months.

Brian Casel: 53:25

Every day that I'm thinking through different decisions, I guess on the one hand, this might be causing me to take more time to decide. But at the same time, I find it really helpful to just write down all of my thoughts, different scenarios, pros and cons, downsides, upsides, worst case scenarios, best case scenario. You know, I write all this stuff down and just get it out of my head and written down. And number one, it helps me analyze and think think things through more clearly rather than when it's all, trapped inside my head. Number two, it really helps me to go back and read from a couple of months ago where my head was at on something.

Brian Casel: 54:06

Because I I find that I get really caught up in in the moment about getting excited about a new direction, and that really clouds out the other options that are on the table. And I can look back and it also helps me, like, internalize the lessons of of of wrong decisions is I I can look back at the at what I wrote at the time and Diagnose. And and kinda just see where my head was at and and and what I was what I was seeing and what I was not seeing at the time. You know?

Jordan Gal: 54:33

Yeah. The the last thing I wanna say about decision making, I think this is more in the context of of a group of people trying to make a decision. What I like to use is is the question of what what's what's your ideal? Like, because sometimes in in a group, people start assuming things, and they they they start putting these weird barriers in place that they that they, oh, Jordan, I assume that you didn't wanna spend this much money on a CRM because that sounds expensive, or I heard you say something three weeks ago about how this other tool is expensive, and this is the same price. So I'm not even gonna bring this up in as one of the options.

Jordan Gal: 55:14

You know? So and you don't know about all these assumptions that people hold. So what I'd like to ask is, what is your ideal? No constraints, no assumptions, nothing. If you close your eyes, what would that ideal be?

Jordan Gal: 55:29

And then describe that. And then let's see how close we can get to it.

Brian Casel: 55:35

Yep.

Jordan Gal: 55:35

Is it at least it, like, lowers everyone's, you know, built up assumptions in this weird web of, like, expectations. Like, I don't wanna suggest something because then they're gonna think something of it. So, I mean, CRM is one of the one of the big decisions we made over the past few weeks. It was it was a difficult decision. Everything has a pro and a con and this and it integrates with this, it doesn't integrate with that.

Jordan Gal: 55:57

At some point, it was just like, look, what's our ideal? We can't get all the way there in a reasonable way, so let's back up one stage, and that's what makes sense for us now.

Brian Casel: 56:06

So let's let's do it. Yeah. Cool. So it's good good good talk today. And Yeah.

Brian Casel: 56:14

It a

Jordan Gal: 56:15

good sign when at the end of the podcast, both of us are like, okay, we can can press stop now.

Brian Casel: 56:25

Yeah, this was this was really good. And as always, if you guys have any feedback on what we're talking about here today, we definitely want to hear it. So, you know, shoot us a tweet, email, whatever what whatever works for you. Keep the conversation going. And as always, you can dig into the backlog of episodes by heading over to bootstrappedweb.com.

Brian Casel: 56:46

And if you're enjoying the show, we'd appreciate it. Head over to iTunes and leave us a five star review. That always helps us connect with with more listeners, and we always appreciate that. So, yeah, we will we'll we'll see you guys next week.

Jordan Gal: 57:00

Talk to you soon.

Brian Casel: 57:01

All right. Later.