TMBA556: Navigating the Dip

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On today’s podcast, we are sharing some personal insights, as well as three specific updates about our core businesses.

We are also announcing that for the first time in nearly five years, we are hiring a Community Facilitator for our private membership group The Dynamite Circle.

Later on in the episode, we’ll be exploring the idea of the moment in a business that Seth Godin refers to as “The Dip”.

You’ll hear why this “middle period” of running a business is so difficult, how it feels to be in that dip, and why so many people just can’t get out of it.

See the full transcript below


Listen to this week’s show and learn:

  • Why we’re hiring a Community Facilitator for the Dynamite Circle. (2:33)
  • What made us decide to make services and software a big part of the future of Dynamite Jobs. (9:08)
  • Why we’ve decided to write a book about one of our favorite topics to talk about on this show. (20:53)
  • The point where people who are starting a business seem to struggle the most. (25:21)
  • Some updates on our personal lives and our goals for the rest of 2020. (37:53)


Mentioned in the episode:

Before the Exit – Our New Book
TMBA Masterminds
Partner With Us
The Dynamite Circle
Dynamite Jobs
Dynamite Deals
Tropical MBA on YouTube
Seth Godin
The Dip by Seth Godin
That Remote Life

Enjoyed this podcast? Check out these:

TMBA526: Our Business Goals for the New Year
TMBA532: The Middle Game
TMBA550: Revisiting Our 2020 Business Goals


This week’s sponsor:

Today’s podcast is sponsored by Earth Class Mail.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian




Full Transcript

TMBA Ident

Dan: Welcome back to the TMBA Podcast. I am joined today, as is per the usual, we’ve actually worked out a non hourly rate. So I’ve got you in here on affordable retainer. And we’re happy to have you back Bossman.

Ian: That’s right. I feel like we’ve crossed some kind of chasm. Now I’m not hourly. I really feel like a part of the core team. Thanks for having me.

Dan: Yeah we gave you the whole talk about shower time and all that, we really want you to be part of this team. Speaking of part of this team, we got a lot of news today we’re going to share some personal updates. We’re going to talk about a role in our team that we’re hiring for. So if you’re crazy enough to want to work for someone as demanding as the Bossman, do listen on.

We’re also going to share some business learnings. I hesitate to call them tips. And then towards the end of the episode Bossman, we’re going to dig into some theory, specifically around this moment in a business we call ‘the grind’, or Seth Godin calls ‘the dip’. Why it’s so difficult, how it feels, the sorts of actions you take in that middle period of a business called ‘the grind’. And why so many people can’t get past it.

In fact, when I look at wealth journeys and entrepreneurship journeys, it’s really this middle period of ‘the grind’ or ‘the dip’, that is the make it or break it moment. So we’re going to dig into that a little bit all in the context of some general business updates in terms of what we’re up to.

Ian: It’s been an interesting last couple months because you’ve been locked down in Austin. And so what that means for us is we’ve had a lot of time to reflect on our relationship and the business and some great things are happening from that.

Dan: So let’s play some funky music or something and get into this thing.


Dan: So the first thing Boss Man is, for the first time in five years, we’re hiring a community facilitator for the ‘Dynamite Circle’. The last time we did a business update episode we talked about how central you know, the DC is to everything we do or the ‘Dynamite Circle’. It’s a classic private community. In fact, a lot of the elements to working on the Dynamite Circle feel more like you know, running a private Country Club or like these more community based businesses. Certainly, it is a business but we don’t always run it like a business.

We’re not doing necessarily like cost benefit analysis or profit margin kind of analysis on the kind of products we deliver, the sorts of events that we do, a lot of it’s just about like, ‘Hey, these are members, this what we think, you know, we all think would be cool to do together like let’s do it and see how it you know works sort of thing’. So basically since COVID, although we’ve had to cancel our in person events, which, and you know, I don’t know we haven’t said it yet on the show, but we had to cancel DCBKK.It’s an easy decision at this point, you know, DCBKK we already have nearly 100 people that have kept their full ticket price deposit in with us to say ‘I’m coming in 2021’. So that’s incredibly cool.

Now on the virtual side. It’s definitely like an emphasis and an opportunity there for us to do more virtually, for our members. You know, we’re still having these local events. But a big part of that community is facilitating masterminds. There’s all kinds of connections happening. There’s DC offers, there’s forum posts, there’s one off masterminds, there’s webinars, there’s all sorts of like mentorship situations. So in other words, we have like this wide variety of sort of virtual connectedness happening in that community. And it’s something we really want to focus on and improve.

And to that end, head on over to ‘Dynamite Jobs com’. You’ll see at the top of the site, we’re hiring for a remote community facilitator, someone to work with us on a day to day basis, to help make the DC stronger. Just basically increase our level of services because I didn’t really know what was going to happen in DC when all of our events would be shut down. But the membership seems to be going as strong as it ever has.

So it’s definitely something we want to focus on this year, improve and grow and you know, if the worst case scenario is that we can only get together in local areas which we have been doing. I mean, over the past few months, like the Austin membership has met up, and we’ve had picnics and stuff. But in terms of these sort of global meetups that we’re known for, if they were to have to go away for a few years, you know, we want to not only be prepared for that, but I think we can still supply an incredible amount of value to our membership.

Ian: Yeah, everybody kind of uses the DC in a different way we find. And, you know, for me personally, it was like, it was always like the highlight to get to see other members throughout the year. And that’s gone away. Sucks. I mean, it basically went away overnight. We had a bunch of plans this year, we had more DCX, which remember hosted events, planned than we ever had throughout the calendar and our two big events in Austin and Bangkok and just wiped right off.
So you know, as a team, and as individuals and as owners, like we’re all having to, like, recalibrate, ‘Okay, well how do we continue to, you know, strengthen these relationships and still talk about things that are important to us and not be able to do it in person’?

Dan: I mean, and the inside baseball there is, you know, last year at this time,
one of our team members, Catalina who’s just such a rockstar when it comes to hosting DC events, we were sitting with her talking man, ‘We might have 20 in person events next year’, looking at all the cities that were going to happen in and how many she was going to fly out to and all this and that was, that’s what she’s great at, and that’s what she loves about her job. And then just to have it all go away. That’s why we feel it’s important to go out and hire here and get somebody in the team really focused on the virtual side of things.

it’s an enormously high workload to facilitate the relationships of over 1000 entrepreneurs, whether it’s doing virtual workshops, or masterminds and we do a lot of this work, a good old fashioned elbow grease, you know, it’s like, a bunch of spreadsheets and emails and phone calls and all this. So we’re really looking for someone with a systematic mindset, someone that can, you know, have compassion and a one on one interaction, but also see the seed of an idea or a system and figure out how to deploy it out to a larger community. So it’s an interesting opportunity for somebody that has a business mind, but also, you know, loves dealing with entrepreneurs on a day to day business, day to day basis.

Ian: It’s been interesting, you know, going over this, this job ad with you, Dan, and just kind of like thinking about that role. There is probably a lot of opportunity to kind of systematise in the position for things that we haven’t done in the past. And I think that’s all good and great, and we’re going to do some of that. But then just getting back to what you started to talk about the beginning when we were describing this role is like, this is a community first, and it’s kind of a business second. And so I think a lot of the reason things haven’t been systematised is because if you start to treat it like that, in a community, things start to fall apart.

And this is a very difficult position in a lot of ways because it has high touch, because it matters the way that you talk to people because your interactions cannot necessarily just be systematised.

Dan: 100% I mean, we try to treat all our members like VIPs and that’s part of the cool part about being a part of a community. You know, and that’s part of what we try to deliver in our on in person experience. And we’re looking to get creative on how to do more, that virtually. And at local hubs, you would say our local chapters. So that’s kind of the vision going forward.

Hopefully, we can get somebody great on the team. And you’ll hear him here on the show. And we mentioned this job ad on the show because, historically, it’s going to be someone that’s listening right now. Or someone that knows someone, a friend or family member or colleague, who you listen to these two guys on the pod and you say, ‘Man, there’s an interesting connection here to be had’.

That gets us moving on to our second of three business unit updates, which would be ‘Dynamite Jobs’, like you said, Bossman. There’s been so much happening at ‘Dynamite Jobs’. We have a CTO now. And we want to build tools that help listeners of this podcast build their teams. What those tools are going to look like, a lot of question marks right now. So there’s gonna be a lot of embarrassing SaaS-ish episodes coming down the pike here because, let’s just come out and say it: me, you and the team at ‘Dynamite Jobs’ are building software tools for entrepreneurs.

Ian: Oh God, what are we doing?

Dan: And if any of y’all are long term listeners, you know how that’s gone in the past. So if you want some drama, you know, go back and search for, you know, our last Sort of foray into the world of SasS. But the timing feels right on this. And the good news is: we need our own software tools. The reason for that is that. We’ve really started to lean into offering services. That’s right. Me and you run a services business. Sweet irony.

Ian: Of all the advice that we give out on this show. I’m pretty sure like not once have I said, ‘Start a services company’. Whoops.

Dan: ‘Hey, we’re so clever. we avoided the service thing, we went straight to product’, and here we are really leaning into services. And I’ll tell you why. Number one is because we need to bring cash flow into ‘Dynamite Jobs’ in order to keep the lights on. It is expensive what we do: all of the jobs that you see on the site every day, all of the design, the search, the filters, all of the emails that go back and forth to candidates to help out our members when they don’t want to get back to people and tell them they don’t get the job. So our team will do it for them. All that stuff. There’s an enormous amount of expense there. And there’s no better way to figure out what problems are valuable to people than asking them for money in return for solving them.

So we’ve experimented with a lot of different services over the years here, but here are the four that we’re currently offering. And we’re having some success with. So the first is an amplify product, which is essentially, there’s not a lot of one on one service. It’s basically like, I want to have the best job at ‘Dynamite Jobs’ for a week, get as many eyeballs on this job as possible. We do that through a variety of means, you know, number one is putting at the top of the site. Number two is proactively reaching out to candidates in our database. Number three is syndicating, potentially syndicating that job at other sites, running PPC campaigns, all that kind of stuff.

The number two product is a filter product. Okay, now you’ve generated so much interest for your job. How can I know just who the 10 best people are? Well, we can filter them for you.

So both of those products are like sort of 500 plus price points, but they’re not like ‘services level’ products, right, they’re more like productized services. Then, in terms of our higher end products, which we’ve been having the most success with thus far, we have a standard recruiting product, which is essentially, ‘We will recruit someone for you, we will do all the work. And we will do it with high level people’.

Ian: You said kind of traditional recruiting. There’s a couple differences actually, between traditional recruiting and us. Traditional recruiting generally takes a percentage of the salary, we do not, we take a flat fee. The other thing that traditional recruiting generally does is it poaches employees from existing companies. We haven’t started to do that yet. Maybe that’s something we’ll do in the future. But basically, we amplify the job, we post it where it needs to be posted around the internet and ‘Dynamite Jobs’, and then we’ve filtered through the best candidates, set up meetings, some type of call assessments, things like that. So there are some differences in, quote, traditional recruiting.

Dan: That’s an interesting point. So that brings us to software. And you know, one of the ways we’re trying to distinguish ourselves from a traditional recruiting firm is we want to essentially drive down the price of the outcome of getting someone great in your company or getting an effect. Or getting effective work delivered to your company.

You’re doing two things on the back end, you’re automating a lot of it with software so that you can move through the various hiring phases faster. And you’re focusing on it because you got people doing it full time. But then the second part of it is that we’re actually building an asset. So there’s this great blog post that I shared with the team, a few times now it’s called, ‘What about second place?’ It’s this idea of, if you’re hiring for, say, you know, a CTO, and you’ve got one candidate that went through three interviews, four interviews, an eight hour technical assessment, they had all the right qualifications, great. They’re hired.

We got paid, the company got their person, you know, winning deal. What about the 100 people that applied? And what about the 10 people that were actually pretty good? And what about the runner up who was actually really good. That’s an asset. And we feel like with a mixture of talent and software, we can find ways to get these people jobs and get companies these services and these employees faster and with less pain.

Ian: There’s a lot of pain.

Dan: That would be something that they’re willing to pay for. And so that’s kind of the thesis. And what’s been interesting about these products is they’ve all happened through referrals, email, and telephone. You couldn’t even find them on the website.

Ian: You can’t even find our website. That’s another story.

Dan: That’s another story.

Ian: Man, Google you know, I tweeted out a couple weeks ago, I was just so frustrated with all that, you know, SEO business, it’s like, you know, the great part about Google, squashing you or not acknowledging you is that you have to build a business that depends on word of mouth.

Dan: Yeah.

Ian: I think that that’s what we’re doing. And we’ve had some success there. And I’m very thankful for that.

Dan: I don’t know, how much more do we need to say about that? You know, there might be a lot of listeners that have seen, you know, we did like some back in the day, we did a wise match service for three or 400 bucks. And I think a lot of prospective customers would go to that and say, ‘I can have like someone on my team post my job posts at like six sites, so I don’t really see the value in that’.

Whereas, now with some hard work, some brainstorming some, some working with our clients, you say, ‘Okay, well, here’s what people want. They want an amazing person in a desk within 30 days, and they’re willing to pay a lot of money for it’. And so we’ll start there, and it’s been going really well. And I don’t know if that’s the endgame business model, but based on the early returns, I would say it’s a plausible ongoing business model, which is really good news.

I guess it’s a mix of like our niche expertise, with what would you say? Like, non-San Francisco/ New York startups and our willingness to do a flat fee and combining that with our platform. And that’s allowing us to have a relatively efficient approach to providing these services. Whereas like you said, traditionally recruiters charge an enormous amount of money. And often they don’t have very strong assets that they’re working with, whether that’s a focus platform, focused on an industry, they’re one off killers, they’re just gonna poach and get on the phone and go from zero to one for every single job.

Ian: You know, getting into the space, Dan, has been interesting just to see who the old players are and who the new players are. You know, every single day, there’s a new job board that pops up. I mean, we have all kinds of alerts set up. And it’s just like man, like people understand I think that things need to change. Trust me, another job board isn’t the way to do it. So if you’re thinking about doing that, just go ahead and squash that idea right now, because we did that two and a half years ago. And now we’re pivoting into this other kind of space, a job board isn’t the whole story here.

Dan: Not the whole story, but it was a cool part of our asset that we can provide to our clients now.

Ian: It is.


Dan: All right. I want to just let everybody know for the record, because this is gonna come up later in the programme, that Ian just made me cut out a big piece of information I was gonna give about dynamite jobs. Ah, you’re gonna hear about it in a few months on the show. But this is a critical part of this second phase of growing a business called ‘the grind’ that I think Ian and I are in right now. And one of the signs of it is constant paranoia.

Ian: This is really bringing me back to a time in our lives. You know, when we didn’t say ‘valet podium’ on our podcast for like, four years. I was like, every week, you’re like, ‘Alright, you want to talk about valet programmes’. I was like, ‘Hell no, we can’t talk about valet podiums, man. It’s how we’re making all our money, you kidding me’?

Dan: Get ready everybody. This is gonna become the worst podcast ever for the next six months. We’re gonna come out and be like, ‘Hey, we’re Dan and Ian we run ‘’Dynamite Circle. It’s a private membership community. We don’t talk about it. Where you run ‘’Dynamite Jobs dot com. We’re not really doing much over there just playing it cool guys.

Ian: Well, I think that we’re gonna talk a lot more about ‘Dynamite Jobs’ Oh, way more than we talked about in the valet industry and it’s obviously a way more competitive market and I think I’m ready for that. That’s fine. But there’s gonna be certain things and I’m not ready to divulge yet.

Dan: It’s competitive. Bossman’s waking up early, skipping rope. Has all his competitors up on the wall.

Ian: That’s right.

Dan: The third project in personal update we want to bring up is that we are working on a book, which I think is another constant theme of this podcast. So we sort of a book in the background maybe happening, maybe not. This one is moving along relatively quickly. It’s a simple idea. And we’ve actually gotten some writing assistance from our good friend, Kyla Gardner. So she’s coming on as an editor and a writer for that project. She has been on the show many times.

The idea has been, in some ways hammered out here on the show over the last 10 years through the guests and through our conversations. It’s called the ‘Thousand Day Principle’. And it’s been cool Ian, because, you know, one of the things I didn’t really want to do during this time is when obviously, we have a CTO at ‘Dynamite Jobs’, we have so many challenges at ‘Dynamite Circle’, we got this really cool book idea in draft. The last thing I want to do is say, ‘Hey guys, you know, I’m going to some hamlet in the mountains for two months to ‘question mark’, maybe write a book’. And so we decided that would be best to get somebody involved with that project to help us get to fruition.

Ian: Yeah, so basically during lockdown, you were staying in my trailer on my property, and we started to think about this book ..

Dan: By the way, this whole trailer thing is really following me around in a negative way.

Ian: Are you serious?

Dan: It’s been bad. Yeah, people, they think I still live in your backyard. Number one. I do not live in Ian’s backyard.And the second thing is, people were genuinely worried about me. They thought I had a gambling problem or something, that I couldn’t afford to be anywhere else so that it was like some shit going down. There’s not some shit going down. Okay, it was free rent, how are you going to turn it down?

Ian: And so just get back to the book thing, because I’m not gonna let you off the hook on this. You’re staying in my backyard in my trailer, again. I just want to go on the record saying that, it’s a nice trailer by the way.

Dan: So inspiring, in fact, that I thought I’ll just write a book in this trailer. I mean, this is amazing.

Ian: Well, so we started you know, you kind of pitched this idea and then for I think, probably a week we just started writing back and forth. You know, different ideas about this ‘Thousand Day Principle’, I was like, wow, this is really something here. And the idea was like, okay, you know, Dan’s gonna go write a book or whatever it is, like, hold on a second. And we kind of just laid out all the opportunities that we have on the desk. It’s like, well, dude, like, you know, we already wrote a book, mostly you, I wrote the foreword, but it was called ‘Before the Exit’, and it was about our exit from our physical products business. And I think it was great. It definitely served his purpose.

But it wasn’t some widely distributed book that had some large following or anything like that. So does it have the potential to have as much impact as the businesses that we’re working on right now like ‘Dynamite Jobs’? And I think like in that area in that arena, like we’re, you know, we’re a bit unproven. So part of the, the calculus for us this time around was like, ‘Okay, like, there’s some really good ideas here. Let’s see who we can get involved to hopefully get it to that level, but not have to spend all of our time and resources because we have this other opportunity kind of cooking’.

So I like our approach of getting Kyla involved because I think it’s a way that we can kind of do both, you know, it’s a way that we don’t have to lose you to that project. You can manage the project and be very much a part of it, but then also give your best energy to the ‘Dynamite Circle’ and ‘Dynamite Jobs’.

Dan: And there’s another element to it when you think about team building and hiring, which is, you know, me and you sat down a few years ago and wrote an Ebook with a crappy cover not optimised on Amazon and gave it out to our friends and stuff. And yeah, it wasn’t a serious project, and we didn’t know we were doing.

And now all of a sudden you think about if you want to have some impact, well, maybe you should get someone involved, that is a book publisher that has written books. that doesn’t know how Amazon works, right? It’s just the simple stuff we talked about on the show all the time. But why am I going to go from zero to learning all about this on my own and basically, frankly, pay for my lack of knowledge, whereas if you can partner with somebody who does have that knowledge, why not?

Ian: Well, I’m actually pretty happy we didn’t partner on the first one because you know, what’s very easy to happen on that first one is like, ‘Oh, I’m gonna get a professional publisher involved. I’m gonna get a professional writer, like, you know, spend a bunch of money and do all this stuff, right’? And then you have the kind of ‘wah, wah’. Yeah, yeah, well received, but not well distributed and all this stuff, right? So I’m actually glad that we did it that way, the first time because we actually had the experience of doing it now, we actually know what it takes to put it out. And now it’s like, ‘Okay, how can we put some real gasoline on this thing? How can we actually spend a little bit of money and push this thing forward’?

So, you know, it’s, uh, you gotta you kind of gotta have this small success I think, in the beginning to have hopefully a bigger success the second time around.

Dan: We’ll see how it goes. And I’ll tell you what, I just got an email from Amazon the other day buddy: $35 in royalties last month, and that

Ian: Wow,

Dan: That was just in one silo, of the greater Amazon world. So feeling pretty good about that. Well, Boss Man, what I wanted to talk about, em … Let me just quickly talk about ‘the grind’. And so the idea of the ‘Thousand Day Principle’, Ian and for the book, one of the cool things about it is we’re having to dig into it and ask ourselves like, ‘Is this like really true? Or is it just something we talked about’? And okay, well, if you take it at face value, what are some of the problems with the theory and where do people screw it up? What’s before the thousand days, what’s after the thousand days, and this idea that, you know, any entrepreneurial wealth journey, once you understand the thousand day concept, it includes a thousand days, you can find it you can find a moment when someone decided that they were going to take a step backwards in their lives in order to potentially have a bigger outcome in the future.

So again, the ‘Thousand Day Principle’ states that in order to recreate your profession salary from an asset that you own. That’s going to take you three years or 1000 days of full time effort. And so what we’re trying to do is take a look at the hundreds of stories that we’ve seen over the years, and try to figure out what are the qualities of those years.

And if you think about that day one, when you first put your product up on the web, people buy it, it can be a pretty amazing, life changing experience. But the reality is for a lot of people, they get hung up in that second year. And I would personally call this the hardest year of our first thousand day journey by a long way. It was 2009, was a very difficult year. And the reason is, is that your momentum slows. Okay, you sold some products on the web, congratulations, that’s like your ante to be in the game. But all of a sudden, all of the money that you’re making from those products is going back into the business.

Ian: Yep. You’re like: ‘Wait a second, wait a second, was this a trick’?

Dan: I heard, you know, our good friend Noah Kagan kept putting his personal money back into ‘Appsumo’ for seven years. So that’s a situation that as someone who’s extensively getting into business because you want to make more money, you want to have more income generating opportunities, it becomes counterintuitive. Well, now all of a sudden, I gotta, like, give all this money back into this thing that is supposed to be giving me money.

I mean, it’s obvious why you might want to do that. But it’s also obvious why I might say, ‘Screw this, I’d rather just get paid’. That’s what a lot of people do in year one, they figure out how to sell things on the internet. They go to a few conferences, they figure out their skill sets. They understand the internet and they just say, ‘I’m just going to make money. I’m just going to charge people money to do stuff for them’.

And that is the sign of someone who didn’t really trust that their investment in year two was going to pay off. Because again, the idea of the Thousand Day principle isn’t simply that you’re just being an entrepreneur for a thousand days, it’s that you’re progressing your asset through the three categories. And so the reinvestment back into systems and people are a critical part of that second year or that second epoch.

It’s a special brand of pain and suffering because, look, three years is a long time to be broke. And I’ll tell you what, one of the key things that second year is a disillusionment that you’ll start to have with your social network, in your family and friends. People that know you as a different sort of person are going to start to see you in this dark pain and suffering period, where you might be working all the time. You’re putting all your money back into your business, maybe you’re neglecting other areas, your life, family vacations, the weddings, your relationships.

Ian: Fashion.

Dan: All these things. Yeah. And I think it’s that social element that a lot of entrepreneurs aren’t prepared for either. Because the reality is, you might be wearing the bummy looking outfit and driving the bummy looking car not just for year number two, look, trust me the good car ain’t coming in year three. That’s not the punchline to this whole thing.

Ian: Year seven to ten.

Dan: The good cars come in five plus years. And the question for anybody with the legitimate cash flow asset in year three and a half is: why would you go straight 60 grand on a Mercedes right now, is that really the opportunity? And the answer is going to be no for nine out of 10 people that understand what we’re talking about with this thousand day principle.

A few other points here, Bossman, the networking that you start to do, starts to become more about your business and not your identity so much, if that makes sense. It becomes much clearer how meeting people can make an impact once you have an asset that’s separate from you. All of a sudden you can see the effect on that asset that conversation had and it’s no longer about, you know, fun or validation, or information nearly as much as it’s about the connection of platforms.

A typical mindset in this year number two will be constant paranoia, something we brought up earlier in the show. And, yeah, a little bit of a funny way, but also for real too, you’re in a precarious position. Like I said, you’re making what feels like a big financial risk. I think if you take a step back and look at entrepreneurship in the context of a career, or even compare it to a traditional investor, it’s actually not that financially risky. But dude, it sucks to like, not have money, it sucks to not have money for years, it sucks to see your friends having money, right? And not being able to do things.

That’s why we call this period, ‘the grind’. And so now you’re, you know, isolating yourself, you’re only hanging out with weird entrepreneurs that you dress equally poorly as you and now you’ve got some paranoia because there’s other competitors doing what you do and people are nipping away at your heels or your customers aren’t very happy with what you’re doing and there’s just all this bad stuff that seems to be circling around in year number two, when that sort of momentum slows.

If you take a look at the big picture, hey, you’re moving in the right direction. But it’s like you kick up dust in that first year. And in the second year, you got to deal with all of it. And you got to deal with it successfully in order to get out of your thousand days. And the biggest mistake people make in this year number two is they don’t focus on the asset, they don’t believe in it. And they instead put their personal needs and lifestyle before the business.

Ian: Well, Dan, I’ll say this. I didn’t really think that much about this stuff when we started our first business because we didn’t have a lot going on. We had kind of like, nothing to lose, you know, like in our 20s. And it was like, ‘Alright, I don’t go to a couple weddings, and, you know, I don’t have any money anyways, so like, who cares? You know, I’m just gonna, like work on this thing all day, because it’s got to be better than what I got right now’. So it was much easier to do that. So I think, you know, as we’re going through this with ‘Dynamite Jobs’, you know, in our late 30s, like some of these things, they’re actually coming up now for us again, but they’re different issues because we’re in a different phase of our life.

We do have a little bit more to lose, we do have a lot more personal things going on, because life is a little bit more complicated. And so I think, you know, the one thing that I’ve kind of realised, you know, in the context of the ‘Thousand Day Principle’ is – it feels more difficult a lot of ways to do this when you’re older.

Dan: I have been asked this question a few times by younger entrepreneurs that listen to the show, I’ll shout out to one Mitko, who’s member the DC is over at ‘That Remote Life’ podcast. He asked me about this. He said, ‘Look, it’s gotta be easier to do your second one thousand days, right? You got some money, you got connections, and all this kind of stuff’. And I think a lot of people would say, ‘Oh, it’s obvious that it would be easier’. But it’s not clear to me that it is. It’s not clear to me that if you want to put yourself on a wealth trajectory with a different asset, that’s not a direct parlay from your current assets, that you have to go through this process again. And it’s a lot of people that gain a certain amount of success they decide not to, and they go into careers that allow them to avoid something like ‘the grind’.

We talked about it recently with Rob Walling, and being an advisor and an investor, how you get to have a lot of the fun that you participate in when you’re building an asset without a lot of the stress and anxiety.

Ian: Yeah.

Dan: And you see a lot of people get into teaching or coaching. Because it’s really fun to share your knowledge with our people. There’s this classic dream of – go be a university professor at the end of your career and teach business. Hell yeah, that sounds baller.I love to do that hang out on campus and teach stuff about what we learned over the years.

My point, Ian, is basically, yeah, a lot of people. They, especially younger entrepreneurs, they see like, older entrepreneurs with a couple bucks a little bit experience and network and they say, ‘Oh, they’re in such a better position’. And some ways they are in some ways they aren’t so, you know, Mitko’s response to me was like, ‘So you’re saying like it’s a level playing field’. I didn’t have this response at the time, but part of me thinks, the playing field is level because you’re playing this one on one against the market. Nobody gives a shit what happens to you and your thousand day journey? No one is sitting there saying, ‘Oh, this person went to this school or this person looks like this or whatever’. I’m not saying you can’t use those things to your advantage and you should, you need everything you can get to get through this grind.

One of the things I’m trying to emphasise in the book is the wrong reading the ‘Thousand Day Principle’ is, ‘Oh, this is just another checklist to follow’. The right reading is this is a gauntlet to run that very few people get through and it is super hard, it will require all your resources you not just check a bunch of boxes like, ‘Well, now it’s time to optimise my website. Now it’s time to start an SEO campaign and now it’s time … ‘ my experience, people who get through the grind period, they’ve pulled resources from everywhere they can.

Ian: Yep.

Dan: And whether that’s partnerships, whether it’s deals, whether it’s you got to leverage payout from a third party on the side so that you can hire an employee instead of pay yourself, it’s things that don’t work out. It’s a lot of things, it’s tough. And it’s not clear that if you’re building something new that having a little bit of experience is going to accelerate this whole process.

Bossman Do you have anything else you want to say about the grind? I guess I’ll just say this, Ian, it’s turned out that by speaking about the ‘Thousand Day Principle’, time and time again, not only on the pod, in the Dynamite Circle forum, also on our pod shop episodes we did during the COVID lock down here, what started out as a funny thing that people were like, ‘Oh, yeah, I felt that, I felt that’, has turned into something that’s, you know, giving a little clarity around what this wealth journey looks like, what the entrepreneurship journey looks like, and what the common patterns and missteps are.

It’s exciting to sort of look at your life and say, Alright, like, I like what’s happening here. I think it’s exciting. I like that my downsides are protected. I’m gonna take three years, and I’m going to go on an adventure. And when most people are gonna grind it out their jobs and take a few vacations and that kind of adventure, like, this is what I want to do, I want to own my own life. And I’m willing to risk three years to try and do it, it’s pretty dope.


Dan: So just to recap, one of the biggest updates is that we’re hiring for a community facilitator. If you know anybody that would want to work with us on a day to day basis. This role is absolutely central to everything we do. You’ll be speaking with Ian and myself all the time. We’d love to speak with you. So check out that job listing. Our second update is the services and ultimately SaaS that we are building over at ‘Dynamite Jobs’. Our CTO made the joke that, ‘Everyone sees SaaS and they forget that it’s a software as a service’, you got to have the service part, if you want to have the software,

Ian: You got to.

Dan: You got to have a service. So we’re focusing on that. And then finally, we are working on a book version of the ‘Thousand Day Principle’, something that has emerged directly by observing guests of this show. And we get a lot of questions about personally, what are we up to? Everybody knows, maybe not all the listeners know that, you know, you’re an enormous car guy.

Ian: I am.

Dan: And it’s not just a thing where you’re shopping cars on the web and deal with them around and stuff, but you’re, you know, building them from the ground up and buying really interesting examples of classic automobiles that have a narrative to them and a history, and you’re speaking with the people who are doing that. And so it’s a big part of your life. It’s a really cool thing.

You also recently bought one of the coolest cars I’ve personally ever seen in person which is a Mini, I don’t know, it wasn’t Mini Cooper at the time was just a mini and with the wheel is on the right hand side, made for the British market, I’m assuming and we took a little cruise around the neighbourhood in it and it was just like smiles, like full time smile and everybody who saw the car waved to us.

And if you want to talk about, you know, what are the rich people doing? It’s like, if you want people to wave at you and notice you in a car, you should buy an affordable Mini and not some expensive Lamborghini that you’re gonna crash into a curb somewhere.

Ian: That’s right, you get a whole different crowd looking at you in your Lamborghini.

Dan: Twenty-two year old guys that use gel,

Ian: Exactly. I love driving that car around and again, getting back to your point about the best things in life you can’t buy. Classic Mini Coopers and depending on what they are, is like a really nice example which this one is and it’s really original, which this one is, it goes for a couple of bucks but this is on the lower end of the spectrum.

So you know, just talking about value to price it’s very high. This is not an expensive car, but it’s definitely a fun experience that you can have. So, personal updates I bought a classic Mini Cooper. I love it. I absolutely love it. It’s one of the most fun cars I’ve ever owned.You talking about how I spend my time. Some of the people that have been to my house for various different reasons. We generally have a party at my house for DCAustin, and on the property is my shop where I keep cars and motorcycles and stuff.

Dan: A lot of listeners of the show have been to your house, which is kind of a cool little backstory beneath the pod. Probably, you know, two or 300 listeners of the show have been to your house.

Ian: I’m building a race car. I mean, I’ve raced on and off, right, I’d like to race a lot more. But the truth is, it is kind of like a full time, part time job. And it’s hard to do with, you know, building a business and having a family and stuff like that, but, and I haven’t done it for the last couple of years. My son is now two and a half years old. So he’s getting to the point where he’s a little bit more autonomous.

Dan: Oh he’s autonomous, that’s definitely true.

Ian: We have a little bit more horsepower in the business. So my goal for next year is to race this car that I have been building for the last, I’m going to say working on it again, it’s been in the, ‘working on’, stage for two and a half years. But my goal is really in the next six to eight months to finish it up.

Dan: And as a third party observer, this car has always been like, ‘the culmination product project’.

Ian: That’s correct.

Dan: And is that attitude, this idea that everything you’ve ever learned about cars, your whole life is going to be represented in this one race car that’s going to be amazing. Has that stopped you from working on it more?

Ian: Yes, absolutely. I’ve taken on various other projects because I want to avoid all of my knowledge and expertise coming out in this one final product, I think is extremely daunting. And so I’ve actually had to like ratchet it back a little bit. So like, ‘Look, dude, this isn’t like a complete representation of you and everything that, you know, let’s just get this thing done’. That’s representative of a lot of things that we try to do, you know, I mean, you see it all the time in business, right? ‘Oh, I’m going to plan the perfect business and everything’s gonna go so right. And I sat around and thought about it for 10 years’. Yeah, that’s, that’s a stillborn business. And that’s kind of been this car for me.

Dan: I think it’s worth saying, you know, what kind of car it is and how much fun we’re gonna have with it. And so hopefully, we can at least have its exhaust note on the show someday.

Ian: It’s a Miata based chassis, but it’s pretty far from a Miata at this point. And it’s got a, it’s got an LS six in it, which is, well, they made that motor for a lot of cars, but it was in a Camaro, Corvette and a lot of other high horsepower, GM cars. So it’ll put out about 500 plus horsepower, and it will weigh about 2400 pounds to the power to weight ratio on that, and it’s better than a Porsche 911 turbo.

So it is going to be quite a handful. So yeah, I think in a lot of ways, and it is scary, because it is a representation of me in the things that I know or I don’t know. And so I haven’t actually put that out I think in a lot of ways. I’m more scared of that and a lot of ways that I am like getting judged on some of this business stuff, which is kind of weird for me. But you know, it’s because I’ve been doing it my whole life basically. Personal updates for you?

Dan: So my goal Bossman is I want to average .. I want to be a 70s golfer by the end of the year.

Ian: And what does that mean?

Dan: What that means is that would put me in that I don’t know the numbers exactly, maybe top 5%, it’s pretty rare.

Ian: Well, well, I’m sure Kim Jong-un is one.

Dan: Yes.

Ian: Donald Trump shoots 70.

Dan: Yeah.

Ian: So put you in their category.

Dan: For those of you who don’t play golf, unless you were on the college golf team or whatever. The number of people that you golf with on any given day can shoot a par 72 is, you might not even know any golfers like that, let alone a handful. So it just depends on what crowds you run in and stuff.

But golf is one of these games that doesn’t matter what your level is. You’re always competing against yourself. And it’s both mental and physical. And it’s also a way to connect with people. So it’s really cool. I have a golf trip coming up, I’m heading out to Colorado, where the balls fly longer, significantly longer because you’re a mile up in the sky. Hang out at some craft breweries and reconnect with some old friends. So that’s basically the game plan by the end of the year, I want to, you know, right now, my handicap is a 7.4 and average score is 82.5. So that’s a personal goal to average in the 70s, which I think is pretty doable. It basically makes it more fun. You know, you get to this level where you’re playing the sport, like as it’s meant to be played. Those are the updates.

We do episodes like this because we get email requests from you guys. So if you have anything you’d like us to address on the show, drop us a line or a voicemail. We’d love to hear from you. And that’s it for this one. We will be back as always, next Thursday morning.

Dan: Negative five UTC time.

Ian: Listen back to the previous episode, to understand why that’s important. See you guys next week. Ciao.

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