Starting Up Sooner vs. Later
Bootstrapped Web. It's May 12. It is beautiful weather out here on the East Coast Of The United States. Gordon, how are doing, buddy?
Jordan Gal:I'm doing well. It's like there's so much to talk about. Maybe we should podcast more often.
Brian Casel:I don't I don't know if I can handle more
Brennan Dunn:than once a week.
Jordan Gal:This is I know. No. It's flying by. It's flying. My Brian and were just saying every we just, like, turn around for a day and then come back, and it's Friday, we're doing a podcast.
Brian Casel:Yep. Yep. You know, like, once a year or so, I actually, like, update my Twitter pinned tweet.
Jordan Gal:Okay.
Brian Casel:It's it's usually something like promoting my business or something. Yeah. Today, for the first time, after, like, nine years of host of cohosting this this podcast with you, I I put Bootstrap Web as my pinned tweet.
Jordan Gal:Oh, fun. So
Brian Casel:You know, I like, we talked about how I I like to ask questions on like, ask for listener questions on Twitter. I'm gonna use this thing on that's pinned on my Twitter as, like, the running thread going forward. That's where I'm gonna post my notes for what we're what we're gonna talk about this week. Okay.
Jordan Gal:Cool. I I like it. I'm looking forward to being able to access that. Did did you say nine years?
Brian Casel:I think so, dude. Like, 2014 is when we started.
Jordan Gal:Yeah. Yeah. So speaking of 2014 I'm sorry. It's, yeah, 2014. So this week, I did an interview with our friend Andrew Warner at Mixergy, and I googled where the last time I was on, and it was 2014.
Brian Casel:Really? That that far back?
Jordan Gal:Yes. Yes. Nine years.
Brian Casel:Wow.
Jordan Gal:So Andrew and I had a hell of a conversation going back. Last time I was on Mixergy, I had just sold my ecommerce business and was starting Cardhook as the car demand of an app. I was I remember where I was. I was in a rental house in Portland while we were doing our big trip to see where we wanted to move, and it was this month in Portland. I remember the house.
Jordan Gal:I remember the Wi Fi was sketchy. I was so scared because I was so excited to be on Mixergy, which was
Brian Casel:Yeah.
Jordan Gal:You know, that that's all I listened to.
Brian Casel:It is such a thrill. Like, I I was on it, I think, twice. And same thing, it was a really long time ago. Like, I think I think I was on it maybe in 2015.
Jordan Gal:Yeah. And you did very
Brian Casel:beginning episode? I yeah. Earlier, I did like a course over
Jordan Gal:there, but
Brian Casel:then I then I did an interview, but it was about like the very beginning of audience ops or maybe even like restaurant engine. Yeah. It was it was far back.
Jordan Gal:Yeah.
Brian Casel:Then I hung out with Andrew. This was a couple years ago. Hung out with Andrew at at his office in in San Francisco. He's great guy.
Jordan Gal:He had got something, like, whiskey or something.
Brian Casel:Yeah. And and it was just,
Brennan Dunn:like, such a thrill to, like, see his recording room and, like, I it was, like, amazing.
Brian Casel:You know?
Jordan Gal:Yeah. I don't know if it has video. I think it does. But if you look at this this, like, this week's video, he and I got so gray, man.
Brian Casel:Oh, yeah.
Jordan Gal:Yeah. Which is comparable.
Brian Casel:All the
Jordan Gal:all the hair in the in the videos went gray, but I guess it's still there, so we won't complain.
Brian Casel:Fun fact. I met you, Jordan, through Andrew and Mixergy.
Jordan Gal:That's right. That's right. That's how we originally got connected with the mastermind group with Brennan Dunn and a few others, Matt. And then we realized that we lived, like, ten minutes away from each other.
Brian Casel:It was it was, like, the craziest coincidence. Like, yeah, we we joined this mastermind group, and then we met up for coffee, like, the next week in Connecticut.
Jordan Gal:Yep. Love it. Love it. Cool. So we we got a lot to talk about.
Jordan Gal:We got Alright. Things on Twitter. I had a board meeting this week. I feel a lot better right now. I'm getting more sleep.
Brian Casel:Yeah, man. Alright. We'll get we'll get into that. I'll talk a little I got a couple small things, like, still like, with Clarity Flow, we we've turned the corner with the new branding and everything. I wanted to catch up on some things.
Brian Casel:So there was one question from last week about getting into more sales demos with this move to Clarity Flow. Okay. So that's starting to take, take shape. And then I also wanted to, respond to and and hear your thoughts on on what Justin Jackson and Aaron Francis have been. Well, Justin Jackson started this whole thread and blog post about like, he gave a take on should you or shouldn't you start or or bootstrap a business when you have young kids.
Jordan Gal:Okay.
Brian Casel:And so I some really interesting thoughts and takes. And then he and Aaron Francis sort of, like, debated both sides of that.
Jordan Gal:Okay.
Brian Casel:And I've been sort of, like, shaping some some thoughts as I've been thinking about it. But Okay. Yeah. Thought we'd get into it.
Jordan Gal:I am unshaped because I don't know what the conversation is like or where the debate is. So I and I I asked Brian not to tell me so that I could react Yep. On the air with my honest first thoughts.
Brian Casel:Yes. Yeah. So so, yeah, where should we begin?
Jordan Gal:Let's see. Why don't I cover the board meeting quickly, and then maybe let's jump into either your business or we can talk about the starting business.
Brian Casel:Let's do it.
Jordan Gal:Kids. Okay. So if you recall a few months ago, we had our first board meeting, and that was my first formal board meeting. At Cardhook, I was the only board member. We didn't have board meetings, and I liked it that way.
Jordan Gal:But now I'm, you know, putting on my my big boy pants with the fiduciary responsibility and millions of dollars of other people's money. What goes along with that is a board and quarterly board meetings. And the board meeting makes for an interesting, like, marker in the business's progression because it creates something on your calendar where there's, like, a bit of accountability. Right? You're gonna talk about how did the last three months go and what is the plan for the next three months.
Jordan Gal:Last time was the first one of the year, so we did an annual budget. So now you're looking back on that budget to test your assumptions and projections on how things are going. So it adds a a significant layer of accountability to running the business. It's still early stage. So it's not like, you know, guidance of a public company.
Jordan Gal:If you miss things by, you know, x amount, then it's not good. It's it's not like that. It's more fluid.
Brian Casel:Mhmm.
Jordan Gal:And, fortunately, our board is very supportive, and we speak with them regularly outside of the board meeting. So it's not like we don't talk for three months and then talk. I speak with them Yeah. On the meetings.
Brian Casel:Can you remind us, like, who's in on the board meeting?
Jordan Gal:Okay. So officially, the board is myself and Rock and our lead investor, Hyun, at March Capital. Uh-huh. But we have our lawyer sit in and Jessica to talk about the product side, right, VP of product, and also JP, our investor from Felix Capital, observes. So we've got more people around the table.
Jordan Gal:We've got a lawyer there. It definitely has the feel of a formal meeting.
Brian Casel:In person? Or Zoom. Zoom. Zoom.
Jordan Gal:Right. There's one person since LA. I'm in Chicago. One person in Ljubljana, another person in Portland, and another two people in Portland, actually, and another person in London. So we're we're all over the place, so Zooms would make sense.
Jordan Gal:So it made for a it's not like it's a stressful week. There's just a decent amount of work to do.
Brian Casel:You you wanna I was gonna I was gonna ask, like, what does the prep look like? Like, how how much of your time and energy goes into prepping for this?
Jordan Gal:So it's a deck. Right? Slides, in a Google presentation. And the truth is a lot of that work is offloaded. Meaning, I go to Elizabeth, our director of marketing, and I say, update this slide with this quarter's numbers.
Jordan Gal:So it's not like I'm doing that work, but I'm responsible for it getting done. Same thing with Sam that does the sales and the biz dev. So we're getting all the numbers. What what I'm responsible for right. Jess does the same thing with the product.
Jordan Gal:Rock does the same thing with the tech. The part that requires work and conversation and thinking and, like, focus on is strategy. What happened since last time that went well? What didn't go well? What went according to plan?
Jordan Gal:What's a surprise. And given everything we've learned, what's the plan moving forward? What adjustments are we making? What are we keeping the same? What are we changing?
Jordan Gal:And the the goal the goal is to convey information and have a bunch of people around the table that really, really care about the success of the company and get the input of other people. And sometimes that's valuable from the people's input. It's also valuable from what you learn about yourself and your thinking as you go through the exercise of writing these slides articulating what's happening. You can almost hear yourself like, oh, I don't actually feel confident in this point of view that I'm saying. Or as I'm speaking, it feels obvious what we should be doing.
Jordan Gal:Or as we're listing out the things we're doing, I can feel in my gut we're doing too much. So all these things, it's like a venue to take a time out
Brian Casel:You know, that away
Jordan Gal:from the day to day and, like, synthesize.
Brian Casel:I I I've said this before, but, like, whether you have, like, your formal quarterly board meeting, like, and it's and and there's real responsibilities there, or you have a mastermind group or and and I have some of that, or or I do my, you know, big, snow, tiny comp retreats with some people. And you put this preparation into, like, presenting Mhmm. And and recapping and and and, like, a review of of what happened in the past year or the past quarter or the past month. Like, that is so valuable just going through that exercise. Even and like, I even sometimes do it and I don't even share it.
Brian Casel:And I just like as if I'm presenting it just to just to go through like a a review process.
Jordan Gal:It's so helpful. Even if you're not presenting it. But right. They they serve the same purpose. When you go to Colorado and talk in front of four or five people that know you and your business for years, it's it's it's really, really similar in whatever.
Brian Casel:I mean, you you have to, like, it it's it's a way to filter out the bullshit.
Jordan Gal:Mhmm. Makes it go public with some accountability there. Yeah.
Brian Casel:Yeah. Yeah. It's so because you can make all sorts of excuses when you're just yourself in your office. Yes.
Jordan Gal:You know? Because you
Brian Casel:And you don't even realize that you're doing it. But when you have to tell someone else about it, that's when you realize.
Jordan Gal:Yeah. You you know what I think about that? I think you have to make excuses for yourself. If you don't, you will lose your mind criticizing yourself and acknowledging the mistakes that you've made and how you could have done better on all these other things. You have to live with a certain set of excuses on why things aren't going perfectly
Brian Casel:Yeah.
Jordan Gal:Daily, constantly, or you will hate yourself.
Brian Casel:And look, I I also really believe in the power of of your personal story. I think that's why I I I get so much value out of being a cohost of this podcast. But it the same is true for doing a review with with with the with the group in Colorado or your mastermind group. It's like you're you're continuously adding to your story and telling a narrative Mhmm. Of this happened, and that happened, and and this was the result of that.
Brian Casel:And if I look back a year ago, this was the the seed of why this ended up happening. Like, you gotta, like, think about it in terms of a story Yeah. Because that's that's how we start to make sense of of and and start to, like, pull away lessons. You know?
Jordan Gal:Yeah. So it's it's always a valuable experience. It's not easy, and it makes for a stressful week even if I'm not worried about, you know, that accountability and people being upset or I'm not worried about that. But it it you buzz on a higher, plane for a few days. Mhmm.
Jordan Gal:And my wife sees it and, you know, I'm just in the back of my mind. That's what I'm thinking through and how I'm gonna talk about this and present this and and why I believe this way and why we're going in that direction.
Brian Casel:So it's like the takeaway. Are you getting energy out of this coming out of it?
Jordan Gal:So the general take in terms of I can't be very specific. But the general take is a stronger, more precise focus on our ideal customer instead of just talking to everyone. Right? There was a stage in the company where we just needed people to use the damn checkout. And whatever it took, just get in and process payments with us and give us feedback and ask for features.
Jordan Gal:And that era is starting to fade into the background. And now it's time to really zero in on the right ideal merchants that will take us to the promise land, take us to where we need to be over the next two years. And when you do that, you have to review everything. You have to review your messaging, your language. For us, it's a question, should you have a pricing page at all?
Jordan Gal:If all of your competitors and people in your space have a contact sales and request a demo and don't have a pricing page at all, you have to align everything. The design, the copy, the messaging when you send an outbound email, the things you say on the phone, the things that you call a document, it's an order form and not a contract, it's all gotta line up. So it is
Brian Casel:Like really embracing like the, the enterprise play.
Jordan Gal:Okay. So even even that, one of the most important things that came out of the conversation is that we are not going enterprise. We are mid market.
Brian Casel:Okay.
Jordan Gal:Because enterprise in the e commerce world is $500,000,000 and up. Right? That's the the giant
Brian Casel:It's like what what do we all even define as like mid market? Like, feel like there's a lot of SaaS that mid market would still be pretty
Jordan Gal:Well, look. In in my experience in the world that I've done business in, a a company that does a $100,000,000 a year is a big ass company, and I think of it as enterprise. And and and one of the things that
Brian Casel:came Yeah. In the grand scheme of things, that's, like, mid market.
Jordan Gal:That that's right. And one of the things that came out of the board meeting itself when we when we were, like, after the presentation, we said, okay. Let's, like, kinda have it out. What's on your mind? What's the first thing that comes?
Jordan Gal:What are the things that you wanna say but feel bad about saying? Like, let's have it all out. The thing that I said was I think we're being imprecise in our language and one person thinks of enterprise as this, another one thinks of this. You need a different type of person to run an enterprise sales process, all this stuff, and we have to be more precise in the language because our ideal customers are between 10 and $100,000,000 a year.
Brian Casel:Right. And I guess the the important thing is, like, what what do they call themselves? Right? Like, you're the person you're you're selling to, do they when they introduce themselves, do they say we're we are a mid market sized business? Or what do they how do they use that word?
Jordan Gal:Right. Because that right. Because they they have their own context, and they look up to companies and look down to companies and so on.
Brian Casel:Because, like, the goal is for your copy to, like for them to be like, yep, that's me. Right?
Jordan Gal:It's it's every touch point. Yeah. Every because if you the dangerous thing about that sales process is if you don't match expectations, in some ways it's like a checkout process. If you don't match expectations, you spook people. Mhmm.
Jordan Gal:If you say, let's get on a call and you're the CEO and you want you go on the first demo call, they're like, that's not serious enough.
Brian Casel:Mhmm.
Jordan Gal:Or if you try to rush into, do you wanna start a trial before they've talked to legal, you're playing out of order. One of the big things that we'll do over the next few weeks is a review of our sales process, which starts with the ideal customer profile and then moves outward from there and looks through our material and the case studies and the demo and the PDF that we send after the just the whole thing to review.
Brian Casel:Nice. Yeah. Exciting.
Jordan Gal:Back to work, basically. More work.
Brian Casel:Yeah. Dude. Always. Always more work.
Jordan Gal:Okay. How about you? That's that's on my side.
Brian Casel:I mean, things are going pretty well right now. I've same thing. Still a ton of work to do and still a ton of things that are happening, but I really feel good about the fact that we have turned the corner. We are fully Clarity Flow now. Zip message is in the rear view.
Brian Casel:It redirects, like and the what's what's a huge relief about that is is that, basically, everyone on my team and myself, those projects of rebranding are done. Like, we're not working on rebranding projects anymore. Now now we can everyone on the team can now focus on new features, building out new marketing campaigns, projects for Clarity Flow. Like, that's a huge relief because, frankly, the the rebrand really pushed our road map further out than I would have liked because we just took so many hours and it was so complex. But I mean, the good news is that we are seeing now the third month in a row of noticeable growth.
Brian Casel:Yes. And is it that feels really great because there were many months before that where we were just not growing very much. And to to see it start to break out three months in a row so, you know, now now I'm now I'm looking ahead around like, okay, so how do we keep this growth rate going through the rest of the year? I mean, so far, this this is a result of the price increase that started about a month and a half ago. So this is all new customers coming in and and and paying higher prices than our legacy customers.
Brian Casel:So I'm starting to, like, map out the rest of the year. We we are working on a bunch of big features that will push a lot of new value into our middle and upper tiers. So that's gonna that's gonna drive more upgrades, I expect, you know, this summer. And then the other thing that I'm looking ahead to is handling all of the the legacy customers and promoting incentives for them to upgrade early. But ultimately, by the end of the year, we're going to upgrade all of them.
Brian Casel:So that's going to be a change and and like a whole thing to navigate, like giving them plenty of advanced notice of the price increase and all that.
Jordan Gal:Yeah. You can do that the right way and the wrong way.
Brian Casel:Yeah. Yeah. So I've trying to carefully plan that. Like it's like, I've done all the work for getting the new prices and the new brand out for anybody new who's discovering us now. The the next thing later in the year will be looking at the the legacy customers.
Brian Casel:I guess I'll sort of touch on something that came up last week.
Jordan Gal:Sure.
Brian Casel:And that's sales demos. So Yeah. Pascal had a really good question last week. I didn't have time to get to it, but it's but he I'm gonna read his tweet. He said, because people are going to be I'm just gonna read here.
Brian Casel:One second. Because people are I can't read some of this. Because people are going to be officializing such a large part of their coaching business communications on Clarity Flow, how confident are you that you won't need to do demos in sales for growth?
Jordan Gal:Okay. There's interesting assumptions inside of that.
Brian Casel:Yeah. Like, assumption I think the assumption in the tweet is that, like, I'm I'm tied to the idea that we're not gonna do sales demos, and that's just not the case. I definitely expect to be doing sales demos. In fact, I did one this morning. And actually, part of the calculus when I decided to not only niche I decided to niche down to coaches and think about this larger vision for the product, one data point in that calculus was like, yes, I actually do want to move away from not not away from self serve.
Brian Casel:That's always gonna be there, but I I wanna introduce the opportunity to have a sales demo process. Because I feel like the previous iteration of the product under Zip Message what was a little bit too self serve, too light touch and, like, low priced and not optimal for, like, a sales demo process.
Jordan Gal:Okay.
Brian Casel:But but now since it is a significant a a more significant piece of software, a more significant adoption process, higher price point, you know, it's essential to a coach's business, that deserves more of a conversation and and concierge and handholding and personalized onboarding. And and I think there's even an opportunity for getting into, like, some paid, like Onboarding setup, onboarding services, paid migration services, stuff like that. So I just see that as an opportunity, not a problem. It's part of the calculus.
Jordan Gal:Couldn't Yeah. Like, for
Brian Casel:right now, it's me doing sales demos. Mhmm. Obviously, I expect at some point we'll have a salesperson doing that. And and then just optimizing it every step of the way from from the from the request process to prepping a new demo to delivering the demo to the follow-up to to an onboarding sequence. Like, all of this is, like, super raw right now.
Brian Casel:We have nothing like, I literally just have a incredibly basic contact form on our website that just we have a demo request. It just says, like, request a demo, like, send us an email, and then we'll get you on a call. And and even with just that, like, raw, like, almost nothing, I've had multiple demo requests in the last, like, two weeks. And it's it's it's almost, like, surprising because, like, you can just go through and sign up for your own account. But but I think that I think that that does speak to this market buying this type of software.
Brian Casel:There's some segment of this market that wants a demo. Yes. We're we're almost we're barely even offering it at this point. Right. People are asking for a demo.
Jordan Gal:Everything on your site is try it free. Yes. And at the very bottom in the footer, there's a link that says get a demo. So people are
Brian Casel:re People are hunting that down, filling out the form and saying, would like a demo, please.
Jordan Gal:Okay. So I was gonna ask you if if inserting the demo and sales process is is coming from you or from the market?
Brian Casel:It's something that I've been wanting to do.
Jordan Gal:Okay. So you you wanna do it. It's not just people are demanding it.
Brian Casel:Right. I just have haven't had the time or bandwidth to, like, actually set up the Can
Jordan Gal:I ask what your what your goal is? When when you say you wanna do it, is it because you think that'll close more business? Is because you'll learn more? Is it to match the expectations of the market? Some combination of everything?
Brian Casel:All all of that. Yes. I also think that the I think demos tend to naturally attract a more serious buyer.
Jordan Gal:Amen to that. Amen.
Brian Casel:And and so they they produce more valuable customers. That's that's been my experience. Yeah.
Jordan Gal:I I have to agree with you.
Brian Casel:I and I've I've done lots of demos in my previous businesses and and sales. Like, Audience Ops was a complete sales process the whole way through, and you you definitely learn a like, I've I've been doing a lot of customer research calls for Clarity Flow, but I haven't had I haven't really gotten into the cadence and the routine of sales demo calls, especially when it's inbound and they request it. That's a whole other dynamic.
Jordan Gal:And That's great.
Brian Casel:Like, it's it's an opportunity to sell, obviously, but it's to me, it's much more an opportunity to learn. Because what I wanna do over the next several months is, like, really hone in on, like because I I've done this in previous businesses where I know that, like, going through a 100 of these sales calls over over a couple of months, I start to really dial in on, like, what are the questions that every lead is asking? How do we have better and better answers to those questions and answers to these objections? And you just start to really dial that in. It it's just a whole learning process.
Brian Casel:And then all all of that, you know, objections answering folds right back into the product. Like, how do we make sure that we have the perfect product to deliver what they're asking for? You know?
Jordan Gal:Yeah. And you, yeah, you you get a lot of fodder. You get a lot of material to work with on copy and materials. We we're big on materials, man. It it really matters when when you talk to someone and they ask you after this call, can you send me a case study that shows someone that switched from BOLT to Rally?
Jordan Gal:Totally. Because that's what we're considering doing. And then you realize, oh, we need to create that and then we need to market it and put it into a blog post and
Brian Casel:put it on the website. Yep. Yeah. And I and I have none of that right now.
Jordan Gal:Like Yeah.
Brian Casel:That's We're so we're so behind and and it's but that's how in in my experience, like, that's how it progresses. Right? Like, I remember in Audience Ops, like, I did hundreds of these demos before I ever had a a premade slide deck to show them. And then I did hundreds with a slide deck of me presenting the same slide deck live, really dialing that in before I recorded a version of that and and get and had a recorded demo to show them. You know?
Brian Casel:And then I and then I figured out what the follow-up cadence should be. And, like, you just it's just like an MVP. You just build on it piece by piece. Plus, frankly, I am just I'm struggling with finding the hours to put in. Like, because I'm I'm spending so much time on the product on these features.
Brian Casel:We're building out payments. We're getting a mobile app ready. We're doing programs and community spaces coming up. Custom domains is actually gonna be the next one that's pretty close to shipping. So I'm trying to push all this all this stuff out the door.
Brian Casel:And, like, the unfortunately, the the sales demo stuff and the marketing projects are still I'm struggling to to find time to give those things.
Jordan Gal:Yeah. But I but
Brian Casel:I need to find I I need to find the time somehow. So that's gonna be a a challenge. Yeah.
Jordan Gal:Okay. But you're on the right track. A few months in a row of growth. Yeah. So do you wanna get into this debate?
Brian Casel:Yeah. Let's do it.
Jordan Gal:I'm curious. I I always love bringing out the personal. I I I sit here in my office, in my house. Right? And I I I feel like there's, like, this barrier Mhmm.
Jordan Gal:Of in this room and then out out of this room. Same.
Brian Casel:You know?
Jordan Gal:And and I really enjoy when the conversation, whether it is with a colleague or, like, this podcast or something else where it kind of reaches out into the house because that is I mean, it's more important to me than what's in in the room.
Brian Casel:100%. Yes. Okay. So I I think this will be interesting. Alright.
Brian Casel:I'll I'll try to recap my high level understanding of of what's what's been said so far from Justin Jackson and and and Aaron Francis. So Justin started, like, a Twitter thread and then a blog post, kind of making the case. And I'm I'm such a fan of both Justin and and Aaron. So this
Jordan Gal:is Yeah.
Brian Casel:This is really, really
Jordan Gal:judging two hours down. It's just opinion stuff.
Brian Casel:Justin's take was essentially kinda arguing for, you know what? It might be smarter in general in the in the broad strokes that if you are a parent of young kids, and I think we're talking about, like, you know, babies, toddlers
Jordan Gal:Yeah. Close to the fire. Like, before
Brian Casel:before yeah. You're you're just trying to survive. Right? Yep. If you're in that phase of life within your family, it's worth considering pushing off the entrepreneurial dream a few years until until your kids grow up and maybe have a bit more space to work with in your life to fit in Okay.
Brian Casel:Your your first start up. Okay?
Jordan Gal:This is a very personal preference stuff where we're in.
Brian Casel:Okay. I think Aaron came on Justin's podcast to argue the the opposite. And and Aaron, I think, is is the father of of two young kids, I think two years old. And and and I I really love how Aaron's how he puts like, he's in his, like, maximum effort era.
Jordan Gal:Okay. It's it's motivation.
Brian Casel:Yep. Yeah. Put in the the after hours, like, full time job plus
Jordan Gal:a hard to bed, look at them sleeping in the crib and say, oh my god. I gotta get going. I gotta go.
Brian Casel:And and, like, yeah, kind of like hustling. You know? Know there's a lot of, like, anti hustle in in some circles, but, like
Jordan Gal:Yeah. That's fine.
Brian Casel:This is the time to do it. Right? Yeah. So I I have some thoughts on it, and I think great points were made on on both sides of that. There there were a few factors in this debate that I feel like went a little bit undiscussed.
Brian Casel:At least I I I missed them. So okay. I mean, I I just tend to be on team. Like, start as soon as you possibly can. Earlier in life, the better.
Brian Casel:Younger in life, the better. Now I I completely understand and respect that, like, every purse personal situation is different. Your financial situation may may be different. Your family dynamics Yep. You know, family first.
Brian Casel:Like, don't don't put your your family or life or your personal health at risk, obviously. Right? But if if you're talking about, like, the the question or even, like, your own, like, internal debate of, like, should I go for it or not Mhmm. I think you I think you and your partner, if if it's something that you want, you you need to find a way to to make it worth work in a healthy way. And that and that might actually mean putting that that might mean a few things.
Brian Casel:Working more more than normal hours. Mhmm. It might mean taking a pay cut for a while than what you might than what you would have been used to making or or you could be earning at a at a job. It it there's obviously some sacrifices. And I think I think Aaron and Justin made some really good points about what what those sacrifices actually are.
Brian Casel:It's it's you know, this this thing that we we do is hard, and it's and it does require a lot of sacrifice. But I I think the point that I wanted to get across was there is also risk in waiting. There's also risk in pushing it off further down the line. I think that it does actually get harder to be successful as a first time entrepreneur later in life than than if you at least start that process earlier in life. I I just think you know, like, put put the kids question sort of aside for a second.
Jordan Gal:Right.
Brian Casel:If you can make it work when you're younger, the like, it it there you have a little bit more going for you. And and the and I and I don't want I I know that we have I know that there are plenty of people who who find amazing success later in life. I'm not saying that's not possible.
Jordan Gal:Sure.
Brian Casel:But I think that a lot of them have been at it for a while. Right?
Jordan Gal:Yeah. Or they use the context built up in their career up until that point.
Brian Casel:That's that's my point is like like, I'm a big believer in like, you have to get through a lot of fails to find the wins. So the sooner you can start those fails, the better.
Jordan Gal:Yeah. I I I could I I think that's just what tends to happen. I don't think that's necessary.
Brian Casel:Yeah. No. I obviously, you could hit it on the first one, but, like, but I'm just saying, like, that that's just a philosophy that I've always like, I know I'm gonna fail in the first few tries. I just gotta get through those as quickly as possible so I can learn and and make progress. I think there's that.
Brian Casel:I think there's also, like, the the more small wins that you can build up earlier in your career, whether it's learning how to how to build and sell and ship a product, maybe maybe building a small business and selling it and leveraging the the the financial outcome to to self fund and bootstrap your next thing. You you and I both have have done that a few times in our careers. Like, you know, I I just think that there's a lot of benefit to getting on the getting on the horse earlier than than than making your very first stab at entrepreneurship be later in life.
Jordan Gal:Yes. Okay. So here's my question, though. The one of the reasons it's better overall or the two of us at least think it's better to start earlier is because you have less at stake.
Brian Casel:Exactly.
Jordan Gal:More people depending on you. Ideally, you don't have a mortgage. All these things that get built up in your responsibility stack over time. So in some ways, that does make the argument to hold off. If you but it look.
Jordan Gal:The whole thing is so context based. If you have never been an entrepreneur and you have two young kids, like, that's completely different than if you've been an entrepreneur for your whole life, and this is what you used to. Or it also depends what you have in savings. Yes. I mean, there there's it's like an impossible question.
Jordan Gal:Like, who's the best basketball player ever?
Brian Casel:Right? It's like, oh, you
Jordan Gal:debate forever because it's just fun to debate.
Brian Casel:But the answer is Jordan.
Jordan Gal:Okay. Alright. We we agree there.
Brian Casel:Like the I I exactly. I mean, it's obviously, like, every situation is different.
Jordan Gal:My take is always, always the freedom of choice. That is the point of this country.
Brian Casel:Mhmm.
Jordan Gal:The the thing that this country does better than everywhere else, it's the reason my parents left their home country and came here is because you can do whatever the hell you want. Mhmm. And that I think some of the things on Twitter and LinkedIn and in that universe, I don't like getting advice from people. I don't like hearing other people give too much advice that's overly opinionated. I don't like hearing this is what you should do.
Jordan Gal:This is what you need to do. If you're not doing this, you're doing that that whole thing is bullshit. Yes. The the whole point, the whole goddamn thing about not only this country, but entrepreneurship and and free enterprise and the ability to start your own business to begin with is you should do whatever the hell you want. And if you and that thing in your belly and you just had your first kid and you've got 5,000 in your checking account and you look at your new six week old baby and you say, I gotta get my ass going now.
Jordan Gal:That whole thing I've been thinking about for the past ten years, it's time to start it now, then fucking god bless, man. That's what you That's what you do.
Brian Casel:Yeah. And I I really do think there's a there is that personal fire. Like like, I think a lot a lot of us doing this just feel like this has to happen at some point. So when is the optimal time to make it happen?
Jordan Gal:Yes. It's But, like, if,
Brian Casel:you know
Jordan Gal:It is. Yeah. Now I'm a little worked up. Anything that prevents that that kernel that's that's forming inside someone to go start their own business, it's it's like this unnatural it's a self limitation.
Brian Casel:Yep.
Jordan Gal:And and it doesn't matter what you say about what those limits are. It's still self imposed. If you are in a completely stuck financial situation and you have a ton of responsibilities, it is still up to you what you do with your time. Anything is an excuse. Everything is an excuse.
Brian Casel:Yep.
Jordan Gal:And and if you allow those excuses to prevent you from starting a business, then that's exactly what what you have arranged. I was gonna say what you deserve. That's a little harsh. It's exactly where you are. That's that's if you have not broken through over the hurdle that says, I have all these reasons not to do it, I'm still gonna do it, that just means you haven't gotten there yet, and you're you are where where you are.
Jordan Gal:It's not like a Yeah.
Brian Casel:Look. And I mean, look. There's just no like, the the point here is to be brutally honest about the reality. Like, it does take sacrifice. I I I know that every every person has sacrificed something, you know?
Brian Casel:Yes. Again, you you and every person has has their own personal limits on what is acceptable and not acceptable. Right? That's right. But, you know, it it just does.
Brian Casel:And and I think that I I just remember when I was 25 years old, I was employed at a at a web agency, and I remember making the decision to quit and become a full time freelancer. And my literal justification that I was explaining to, like, my parents and my girlfriend, who's now my wife, and, like, you know, I was like, you know what? We don't have kids. We don't have a mortgage. I'm not getting paid all that much anyway at that job.
Brian Casel:Like, if if I'm going to take this leap, like, now feels like a pretty safe time to do it rather than being later in life. Because I have many friends who who waited until later in life, until making, you know, and now they're making 6 figures, and now they do have kids, and now they do have, you know, a mortgage. And it's it's it's just harder. You know, a lot of them still still manage to make that jump, but a lot of them don't because it's just so much harder to make the necessary sacrifice when you're later in life. You know, it's just like that's that's the and and I and I think that there's also an element of, like, you you gotta get even now, like, for me, I'm I'm still making less than I would like to make personally as in terms of my income and and what I could be making on the job market.
Brian Casel:Right? Yep. But No point. That's a I mean, obviously, there's a I have a financial runway and and and a history in in my business and all that. Like, it's I I've put the chess pieces in place to get to where I
Jordan Gal:am right now.
Brian Casel:But the
Jordan Gal:Unfortunately, I think both of us have to acknowledge we would have made more money if we went the corporate track. No. Zero question. At least in my mind, zero question. We would be better off financially today if I had stuck with my Solomon Smith Barney investment banking job.
Jordan Gal:No question. Probably by an order of magnitude.
Brian Casel:So Yeah. I mean, I wasn't in the banking industry, but I I I also think that I I would be making more every year up
Jordan Gal:here now.
Brian Casel:But I but I also strongly believe that, like, I have a pretty valuable asset that I that I own, and that's my business. You know? Yeah. That's right. The I but I do wanna a little bit argue the flip side because I feel like Justin Jackson Okay.
Brian Casel:Did a really great job in his career. I love observing people's careers, by the way, and, like, the moves that they make year to year. Really? That I
Jordan Gal:I love it.
Brian Casel:I I think it's that's why I love podcasts.
Jordan Gal:Yeah. Okay. Okay. So you you like following along that that journey and narrative.
Brian Casel:I I I'm always fascinated when people are making major career moves and and a chess game that is your career. I love that. Okay. That I
Jordan Gal:think that's interesting. I I have been thinking about that recently because you and I, my friend, we are no spring chickens anymore. No. Yeah. So I I think about that sometimes.
Jordan Gal:And
Brian Casel:Yeah. I'm seeing some gray hairs in both of the both sides of our Zoom call right now for sure.
Jordan Gal:My general take, like, my conclusion when I look at the whole thing and I ignore the mistakes of the past and I don't regret them and all that, my general conclusion is I'm really motivated to make this work big. Same. That's that's my conclusion overall is all the stuff that happened in the past and where we are in the timeline, like, it's not too early. It's not too late, but, like, it would really be nice if this hit because I it does not sound nearly as appealing to start a new company five years from today as it did at 28 and or 33 or this or like, you know, it it feels like a bigger deal.
Brian Casel:I mean, look, there you know, again, if if you can get if you can get your your financial, like, savings in order and your family and and your of course, like, goes without saying, like, your spouse, your partner, who's truly a partner in this
Jordan Gal:Like it or not.
Brian Casel:Has to be has to be on board, you know. And and I think all of us who who do this would say, like, we have an amazingly supportive family to to make it happen. Right. I hope so. The you know, like if let me try to get my thoughts in order here.
Brian Casel:Mhmm.
Jordan Gal:You should speak about Justin Jackson's point or like his like
Brian Casel:Yeah. I I think that, like, you know, doing it if if you are in a in a position where you just have to have the full time job, there's no getting around it to pay the bills, there are still things that you can do to to put yourself To just start. In a position to start. And that doesn't that doesn't even have to mean, like, literally starting a business while you're still employed, but you can do things that will benefit you later when you start a business. You look at Justin Jackson, he he was talking about how he, you know, he had the snowboard chops, then he then he closed those up, went to employment for several years to get his bearings with his family.
Brian Casel:But you know what he did during those years? He built an audience.
Jordan Gal:That's right.
Brian Casel:Amen. He had a podcast and a newsletter and a membership and you know, maybe made a a little bit of cash on that, but mostly he's building an audience. So that by the time he later in life when he was building businesses, that's a huge asset. I don't care what anyone says about audiences. It makes it easier when you
Jordan Gal:start. 100%. You know, it's impossible to tell what element or what percentage of the success of transistor is related to that. But
Brian Casel:It's a head start. Mean, you might be I I I'm sure he would he would attest to that. Right.
Jordan Gal:Years of work.
Brian Casel:Yeah. And I I remember listening to his podcast back in the day. Product people, I think it was called.
Jordan Gal:Yeah. That's right.
Brian Casel:You know, like, but and and that is and that's the kind of thing that if you are in a place where you just don't have the hours in the day or the energy to put in the early mornings or the late nights because you gotta pay the bills, you gotta do the full time job, at least you can get on a podcast one hour a week, or at least you can write a newsletter. You know, like, that's that's a that's a actually a a pretty small investment
Jordan Gal:You can do something.
Brian Casel:To do something to grow an audience. You know?
Jordan Gal:Yes. I think we're all I think we would all pretty easily agree on while entrepreneurship is incredibly important and we want everyone to be able to follow their, like, dreams in life, none of us wanna see someone put their family in a Of course. Terrible spot. But what that means is different for everyone. I took a preposterous amount of risk with a young family in terms of, like, debt and whatever else, and that was just my risk tolerance and preference.
Jordan Gal:And my older brother would never do that. And that's something that he and I talk about in just acknowledging there are differences in personalities. He's an entrepreneur. I'm an entrepreneur. But there there are differences in your willingness to take on risk.
Jordan Gal:And everyone's personal situation is different. This and that. So yes, we really people take on I also think
Brian Casel:that if you're going for a job, there are more strategic jobs to take than others. Right? True. I thought Aaron made a really good point about this. Like, his role right now at PlanetScale, it's it's it's in the same sort of industry and and space, but it but it's also like he does coding for his startup, but more like courses and content for for his job.
Brian Casel:So it's like a different a different balance. Or or you might be in a role that could where you can learn a ton about a a part of the industry or or a skill set that you can leverage in your own business. Like, there are things that you can do that are still beneficial to your future business endeavors in in an employment situation. You know?
Jordan Gal:That's right. Amen.
Brian Casel:Yeah, man. But but I'm I'm still on team. Go for it when you're younger.
Jordan Gal:Yep. That's right. What else? I I I I had an interesting experience this week. I I went to Twitter.
Jordan Gal:Okay. So here's what happened. I'm closing down a corporate entity that has a four zero one k attached.
Brian Casel:Oh, yeah. I wanna hear about this.
Jordan Gal:Okay. So I have been looking at that and thinking, okay. It's got a few bucks in there. It's not crazy, but it's a significant amount of money, and it's pretax. And I have always been frustrated by the four zero one k system because you have so little freedom over your own money.
Jordan Gal:So great. You get to put it away directly from your paycheck, and it gets put pretax. It can grow pretax. Fantastic. The issue is all you can do is basically say, well, 50% stocks and 50% bonds or seventy five twenty five or not.
Jordan Gal:Like, you have no control over what it's buying. I remember I have I have an email. I have the goddamn email. I emailed the people, and I said, I wanna buy Tesla stock.
Brian Casel:Mhmm.
Jordan Gal:I I I don't know what it was. $50,000 or something at the time. And I said, I just wanna buy all Tesla stock with with this money. And they were like, no. You can't do it.
Jordan Gal:And if you look at when I sent that email and what has happened, it'd be worth, like, $750,000 or something ridiculous.
Brian Casel:Right.
Jordan Gal:And that has always bothered me. And so what I what I what I'm seeing now is when
Brian Casel:I You're saying, like, you you just wanna you you would wanna, like, allocate the actual stock purchases in
Jordan Gal:the four zero one k. Control over my own money for god's sake. Yeah. So this is an opportunity. When you are closing down a corporate entity, you get to do something with the four zero one k.
Jordan Gal:You get to roll it over. So instead of just rolling it over into, like, Rally's four zero one k and have be in the exact same position, I thought this is the opportunity to to go the self directed route. Mhmm. So there are a whole bunch of different options, and they're all confusing, and no one really tells you what you should and shouldn't do. And so it's like this weird scenario of, oh, I thought I wanted a self directed IRA.
Jordan Gal:Mhmm. Because then you can you can buy a specific stock. You can invest in real estate. You can invest in startups. You can do whatever you want with the money.
Jordan Gal:So I looked at a bunch of different options. And I went to Twitter, I asked people about it. And fortunately, I got an introduction from Drew Sanaki.
Brian Casel:I don't know if
Jordan Gal:you know Drew. He's in the ecommerce world. Great guy. Smart entrepreneur and smart person overall. He pointed me toward a company that helped me set up a solo four zero one k.
Brian Casel:Yeah. I remember looking into this years back.
Jordan Gal:Right. So I thought self directed IRA was gonna be right for me. The issue with the self directed IRA is that you need, like, a service provider. And then when you look into the service providers, it's not that much control over your money. So there's like this checkbook thing versus noncheckbook.
Jordan Gal:It's basically like, do you have a checkbook and an account? So I looked into something called Alto IRA, which looks great. But then what I realized was if I wanna make an angel investment out of it, which is one of the things, you know, Peter Thiel kinda made that popular. Have you heard of Peter Thiel's thing? So Peter Thiel, our What?
Brian Casel:Like, bringing angel investments into your
Jordan Gal:Our our boy Peter Thiel invested in Facebook out of his IRA. So all of the profits from his $500,000 in the first investment into Facebook are all nontax. I mean so right. So that's a billion dollar move. Right?
Jordan Gal:That's unbelievable. And that story is so good that it popularized this idea, and now everyone's making startup investments out of their retirement account Wow. For for better or worse. So I I wanna be the next Peter Thielberg.
Brian Casel:In the dark on all this stuff. I just I'm just like a
Jordan Gal:I I think most people are. And some
Brian Casel:people set it and forget it. Like I'm just looking at two inch. Like, I know it's costing me potential upside, but I just don't have the time or energy to become an expert on this, and I would fuck it up anyway. So I just I think that's how much safe options, the the set it and forget it. That's been my philosophy.
Jordan Gal:Yeah. That's fine. As long as you got something growing pretax, it's all good. So I'm I'm I some people are also too into it, they're, like, super optimizers, and then, like, turns me off. So, anyway, it turns out that it it would be it would be much more difficult than I would want to invest in in startups.
Jordan Gal:You basically have to have the the founder, like, go create an account with Alto IRA. And that's like, well, what are we talking about? No no one wants to do that. Mhmm. So it turns out if you have an LLC that you are the sole member of, if you are self employed and make like $500 a year when I still do some consulting stuff for my brother, so I have a little bit of income in this in this LLC, and that's enough to qualify you for a solo four zero one k.
Jordan Gal:And that is, like, held in a trust. And then you go to Chase Bank and you open up an account, and then, like, you got a bank account. You have a pretax bank account to do stuff. You can write investments for real estate. You can write a check for a startup.
Jordan Gal:You can buy Bitcoin. You do whatever you want because it's like really your money. As long as you don't pull it out of that trust Mhmm. Into your personal, you you're you're good on the the tax front.
Brian Casel:Interesting. That's what you're doing.
Jordan Gal:So all all you founders raising seed rounds, call me. There you go. Yeah.
Brian Casel:Very cool. Yeah. I just like that. Yeah, man. I, you know, like, a a financial adviser for startup entrepreneurs who are too busy on their business to care to research and learn all this shit, I'd shut up and take my money.
Brian Casel:That's what I want.
Jordan Gal:Yeah. I I I hear you. My my younger brother who has a lot more money than I do, he he advises, to go with, relationship. Like, find someone that you actually trust. This is what they do for a living.
Jordan Gal:You could just ask them the question instead of going to Twitter or things like that. But I I have not not made that leap.
Brian Casel:Yeah. Or going to ChatGPT. I've been dude, I've been I've been really, like, using it more and more. Just, like, asking it for not really advice, but, like, how does stuff work? Like, I just, like, ask questions to like like, if I'm planning, like, a big new feature, like, help help me strategize on the approach on this, or, like, how does this system typically work?
Brian Casel:Give me some basic information so that I can start to make some decisions. Like, I'm just using it more in the day to day than I did before. It's really interesting.
Jordan Gal:It is it is growing in value, and it's like insidious where once you get it lodged in your head to go that path when looking for an answer. Our development team has started to use it more. I think they just use it to build a Chrome extension. Nice. It's tough to identify which website is using, let's say like a specific e commerce platform.
Jordan Gal:We asked it how to identify things and here's a bunch of sites that use it. What's unique about them? Yeah. It's kinda wild, man.
Brian Casel:It it is wild. Like, I I was planning out our new payments feature. We're gonna be using Stripe Connect, which will be my first time working with Stripe Connect on a on a big feature. And, like, we're just at like, so just in the very early stage, technical planning and feature scoping and shaping, I'm I'm trying to ask all these questions like, what's what's possible? Like, if I can I design the feature this way?
Brian Casel:Will users be able to do this or that? Like, is that an option? And, like, you know, and it gave me really good information that I can then use to shape the feature. You know? And I'm I'm also we've started to use it in in our marketing work.
Brian Casel:And I'm I'm at this point right now where I'm hiring I'm looking to hire some writers for for blog content for for Clarity Flow, and I just can't get my head around the idea of, like, how could we not use GPT four as an integral part of our article writing process. It it almost seems ridiculous not to use it. Mhmm. I I definitely think that there's a there has to be a human element in content creation, especially to make sure that our brand voice and our and connection to our product and all all that is there. But filling out a 3,000 word article, like, it just seems a little ridiculous, like, not to rely on chat GPT, especially GPT four, for, like, a significant part of that process.
Brian Casel:Just gotta figure out the right workflow and how to do it well and how and have it not just regurgitate garbage and, like but
Jordan Gal:Yeah. It does feel like writing is that first territory where it it it is significantly disruptive.
Brian Casel:Yeah.
Jordan Gal:Yep. That's right. Yeah. Our, our director of marketing is going out on maternity leave soon, and I am feeling very lonely. I don't know what to do on the marketing.
Jordan Gal:I have so much work to do. So I wouldn't be surprised if we rely on on on GPT much more.
Brian Casel:Yeah, man.
Jordan Gal:Yo. It's Friday.
Brian Casel:Let's do it. Let's do it. I think we're gonna actually fire up the grill for the first time tonight.
Jordan Gal:Nice. Used my smoker for the first time since I moved here Awesome. Yesterday.
Brian Casel:That's like the first thing you you shipped over. Right? It's like, get the smoker in place. Okay. Now we're set.
Jordan Gal:Yes. I got real ambitious so I threw away I gave away the the other barbecue because I was like, I'm gonna get, like, the super legit thing, but I haven't gotten it yet. So I'm relying on my smoker right now, but it works as a as a grill too. Nice. I look forward to all of that version of life while my kids are bouncing on the trampoline and I could, like, sip sip a beer and smoke some meat.
Brian Casel:Hell, yeah.
Jordan Gal:Yo. Thanks for listening, everyone.
Brian Casel:Alright, folks. See you.
