Justin Tan: hiring a GM instead of selling Video Husky

Full transcript

Edited for reading. Select a time to play the audio from that point.

How Video Husky started (00:00)

Alex: You know how post works. You’re the post man. Fix everything in post. All right, where to start? Video Husky, done-for-you video editing. 2014 you kicked off?

Justin: No, way later. 2018.

Alex: Was it ‘18? OK. What was the inspiration? Why did you want to do video editing?

Justin: Way back then, I guess it’s seven years now, it was when video was becoming a real thing on social. It’s weird to say, but the internet finally allowed you to actually watch enough video. So pre-TikTok, pre-Reels, pre-Shorts. It was the time that Facebook advertising was really going towards video. I was trying to do video Facebook ads and couldn’t really find a good way to do it. I happened upon Design Pickle’s model for graphic design, and I thought, oh, we can do this for video editing. That’s pretty much the inspiration behind the idea.

Two t-shirt businesses and Facebook ads (01:08)

Alex: And your background was e-comm? You’d had success in e-comm prior.

Justin: Background? I don’t really have a background.

Alex: No, you’ve got a background. You’ve got a profile.

Justin: Before that I was doing e-comm. I had a wholesale t-shirt business, and then an entirely other online t-shirt business. I don’t know how it ended up being about t-shirts. They were two entirely independent things, but that was the common thread. The e-comm was where I had learned mostly about Facebook ads, doing print-on-demand t-shirts.

Ten customers in 90 days (01:42)

Alex: OK, so we can give you the nickname the t-shirt baron. I remember talking to you back in the day, which, if you kicked off in 2018, must have been around 2018, 2019. One of the things that struck me early was that you got paid acquisition. It seemed to me like the engine of what you were growing at the start, and I think you did pretty well with it. That was learned from the prior businesses, right?

Justin: Yeah. I remember we had this conversation. I started Video Husky, the first iteration, on March 1st. I remember very clearly, because it was: 90 days, got to get 10 customers, or I’m not doing it. And that happened. But it took all the way until the end of August before I thought, oh, let me try Facebook ads. I don’t know why it took me so long, given that was my own background. But we did it, and at that time, in 2018, ads were cheap as chips. And nobody else was doing it at the time, so it actually worked out really well.

Alex: That’s funny. That’s a Kiwi reference, by the way. Cheap as chips.

Justin: You stay here long enough and before you know it you’re saying all kinds of weird things.

Alex: You’re hitting the cuzzies and the bros.

Justin: Yeah, a little bit here and there.

Alex: Yes, I love it.

Straight from validation to scale (03:10)

Alex: All right, so 90 days, 10 customers. Talk me through, well, not then to now, because that’s going to go for 45 minutes of uninterrupted goodness. What was the next threshold you got through after those first ten? Because that’s a validation stage, right? You feel like you’ve actually got something.

Justin: Yeah, that’s a validation stage. After that it almost went straight to scale. From, say, quarter four of 2018 to the end of 2019, the 15 months after that, it was just straight growth. There was a huge need at that time. All the way up to maybe quarter one of 2020, right before COVID, it was bringing on new customers, bringing on new editors, scrambling, doing as much as we could to lock things in, occasionally having to turn people away. It was a wild time.

COVID takes 30% of revenue (04:20)

Alex: Did you peak around COVID, or towards COVID? What was the impact of COVID?

Justin: COVID’s impact was pretty big. The growth in 2019 was up and up, with editors, customers, revenue, everything. The one thing that wasn’t really up was profit, because we always had to bring on new editors in advance of new customers, and there was scaling and new websites and all these things. It’s not e-comm. It’s not like we had to do a big batch order. But it was still a phase where you have to put cash in.

I remember in January of 2020 I said, OK, I’ve got to get a handle on this, because we were now way over the 83, 84K mark. So in January it was: OK, I’m going to do this right. Let’s start figuring out what the right P&L should look like. I came across this company, Clever Profits, and they had this thing, the Perfect P&L. They showed you how much you should be paying for each sector of your agency business. I thought it was great.

The only problem was, when we started with them it was February, I think, and then in March COVID hit. So you’re working with a certain top line, and then all of a sudden 30% of the top line goes away. I thought I was being responsible and doing the right thing, and then it just went straight into firefighting.

One round of layoffs and a 20% pay cut (06:04)

Alex: So did you need to let people go?

Justin: Yeah. We did one big round of layoffs, and then everybody remaining at the company agreed to a 20% pay cut, which was very nice, actually. It was a very, very rare instance, but everybody was OK with it.

Alex: And that was just so you could stay afloat, I guess? Keep the lights on?

Justin: Yeah, essentially. At that time it was a big town hall, and it was, OK, blind vote. Are we letting go of more people, or are we all taking this together on the chin? And everybody agreed to take it together on the chin. So that was very interesting. I think it’s the one out of 50 situations where you can actually do a group pay cut.

Alex: Yeah, very, very rare. So what was the team size then? Where did you end up during COVID?

Justin: I think at that point there were maybe 40, 45 people. Maybe 50, even, shaved down to 40, something like that. I don’t even know. It’s been a while.

Why he spent big on brand and design (07:22)

Alex: Yeah, for sure. As far as the product itself, what you provide. I remember back in the day a big thing for you was having a brand and having an identity. At one point I think you wrote something about it on Twitter, in a thread probably. You were talking about this website that you built, and it was pretty expensive, and then you actually looked at the numbers.

This stuff to me is great, because I’m of two schools of thought. You’ve got a really painful problem that you solve, and you can just do the thing we did with WP Curve back in the day. If you go back to the Internet Wayback Machine and look at it, it almost makes your eyes bleed, it’s that ugly. But the problem was so significant that people would hit the PayPal pay button and do it. You can get away with that. I know of a few productized services that have had terrible design for seven or eight years and have still been able to solve the problem.

But you were pretty gung-ho on brand and pretty gung-ho on design. So talk me through your thoughts around investing early in design and brand. By the way, I personally love the brand. It really has a character and an identity, which I think is awesome, and there’s a lot of pride in that. And was it a Twitter thread you wrote about it?

Justin: I don’t know. Maybe. I wrote quite a bit more in 2022, I think, but definitely not at the time. Maybe I had a blog post somewhere. That might have been it.

I thought branding was quite important at the time, and maybe this comes from a more e-comm background. You had Shopify, and Shopify instantly made everything look nice. If you were a Shopify storefront, you had to compete against Amazon. On Amazon you have all the trust, the authority, etcetera. So the one thing you could do compared to Amazon was look good, because Amazon is so standardized.

So I always wanted Video Husky to look good, because that’s the first impression you get. And as an online-only store, you’re not even hiring the editor when you make the decision, because you haven’t met your editor yet. So you’re trusting in something. And a brand, it’s like Tinder, right? You make a judgment call in the first three seconds. Every other company, which admittedly at that time was two other companies that did a similar model to us, had very, very ugly sites. It was an instant differentiator.

Now, going back, would I spend that much money on the site? I don’t know. But on the flip side, it’s what, six, seven years later now. The site still looks good. It’s still very unique, I think. And I think it will stay that way for the next five-ish years, so we don’t have to go for a rebrand anytime soon. Some pros, some cons, I guess.

Alex: Did you see a difference in conversion?

Justin: At that time there was a slowdown in the top line and the number of customers we were getting, or an increase, essentially, in the cost per customer from paid ads. The site came online, and then it went right back down to what we really wanted it to be. It lasted that way from the beginning of Q4 of 2019, when we began, all the way into quarter two of 2020, when shit hit the fan.

Why video is harder than graphic design (11:05)

Alex: Shit hit the fan. I like that. Cool. So, challenges with the model, challenges with what you do. When I looked at Video Husky I was like, if you can pull this off, it’s a brilliant service, because there are so many moving parts. In my opinion it’s very high touch until you get to a templated kind of model, where you know what your client wants. So there’s a ramp to onboarding and maybe a ramp to success. How did you go about running an efficient team when the service is that high touch? What did that actually look like?

Justin: I think this is one of the struggles of video compared to, say, graphic design. I remember even Russ talking about this way back when. He talked about how graphic design is easier because it’s a 2D medium. It’s so much easier to understand and replicate something. Video editing is a 3D medium. Not in the physical sense, of course, but you have to think through time.

On top of that, you’re not end-to-end responsible. In graphic design you can be end-to-end responsible for creating everything. Video requires good footage, and that makes it very difficult to guarantee a good end result.

So for us a lot of it came down to better onboarding, especially for the less technically capable. You could split our customers right down in half: the people who had a video background, who understood how to shoot, who understood how to edit, and the people who were still recording with their MacBook Pro cameras and no mic. You almost have to have a different onboarding process for each.

The best customers already make video (12:58)

Alex: OK, so it started with onboarding. Back in the day the project management system you used was Wrike, I think.

Justin: Yeah.

Alex: I remember seeing how you’d configured this thing. You did a lot of work on configuring it to fit your workflow, and we went back and forth on a bunch of workflow-level tips. But did you see patterns in the relationship between the complexity of what the customer needed and their LTV? What patterns did you start to see emerge over that time? I have my hypotheses of what it would be, but sometimes the data is very different.

Justin: It’s interesting, because it’s quite different now. I was hands-on in Video Husky all the way to 2021, and it’s now 2025. What’s going on now is very different to what happened back then, so it’s two different conversations.

At least back then, the people we found were the best customers were those who consistently already created videos and who were bottlenecked by editing. If you’re trying to work with somebody for whom it’s their first time doing video, and they’re looking for an editor, well, we fit into their systems, not the other way around. So you almost have to already have a backlog of a lot of footage, ideally good footage, and a vision of what you want. Those are the people we worked best for.

If you already had that backlog and that need, and you didn’t want to go through the difficulties of hiring somebody, and you just wanted to be able to scale up and down, because maybe your work or your publishing schedule is seasonal, that’s who we found were really good customers.

Taking revenue you know will churn (15:05)

Alex: And for the folks who were more at the beginner level, is that something where, during the sales process, you’d qualify them in and out? How did you manage that? Or did you go, OK, we’ll take the revenue and we’ll try to figure it out as we go?

Justin: I think for the most part we did take the revenue, even if we knew there was a very reasonable chance that they would not stick around for a long time. Maybe, going back, there’s a better way of running this business. But I would think in terms of: all the ad money is spent, the marketing money is spent, so we may as well recoup the funds.

Which is OK if you have empty editor slots. The problem is when you are hiring additional editors in order to fill that need, but that demand isn’t long-term. Then you end up with higher overhead, and that higher overhead means you need more revenue to cover it. So this is where the sizing of the business also matters quite a bit, I think.

The birthday problem at 50 people (16:10)

Alex: By sizing, do you mean there’s a threshold at which you can operate where it’s profitable and customers are satisfied? What does sizing mean?

Justin: It’s the difference between, call it, a software business and a service business, especially a service business that you’re not personally delivering. There is a point at which your team gets bigger and bigger and bigger, and it’s just so much more complicated to run.

The best example, which I used to joke about, is birthdays. When you have a team of five people, it’s very easy to celebrate birthdays. Ten people, you can still do it. Maybe it’s once a month, essentially, and you still send a birthday message. What happens when you have 50 people? You’re sending birthday messages every week. It becomes more and more difficult to make something work for everybody.

It’s that thing where you can no longer know everybody on a first-name basis. You can no longer keep in touch. And that distance, especially in an online business, I think makes things trickier. If you’re in an office, you have to give the benefit of the doubt, because you see the human. Online, it’s very easy to just default to: oh, why can’t things be this way or that way?

Alex: Yeah. Jason Cohen has a really good article about this. I think it was related to WP Engine. He’s saying that as you scale out, things that are tiny problems when you’ve got a thousand customers become much bigger problems at ten thousand, and logarithmically at a hundred thousand. Obviously that tracks. Those can be big business risks. They can be meaningful things that can actually be spanners in the works.

Recovering from COVID, then burning out (18:11)

Alex: What size did you find was the happy medium, where things were humming?

Justin: I don’t know if there’s a size. Things just got better after I hired a general manager.

And this is maybe to each their own. Let’s go back to that timeline. In Q2 2020 we lost 30% of our revenue overnight. So you’re in firefighting, and we had maybe two weeks of cash in the bank, so not a ton. But of course they turned the money printer on, and they had that PPP loan, so all these businesses all of a sudden had all this extra money.

It took maybe another four to six months to get back to where we were. Then over the next six to twelve months, all the way towards the end of the year, call it roughly, thanks to Clever Profits and their profit statement guide, we were able to consistently eke out a profit. So we built a good two and a half, three months’ worth of cash in the bank, while still paying myself a good wage. Or a good wage at the time. God knows inflation has decimated that.

That took us all the way until towards the end of Q2 of 2021. We had redeveloped the sales process at that point. And it was around then that I just felt so, so, so burnt out from all the team managing. It felt like very firefighting-type work, and I wanted to figure a way out, essentially.

Three ways out, and why he didn’t sell (20:20)

Alex: So what were your pathways? What were your options at that point?

Justin: Essentially you have three options. One, can you scale your role back so you’re only doing the things you want to do? That was the first one. I’d already tried that. I didn’t really like it, and it didn’t provide enough mental space or bandwidth to let me go and explore the next thing. I didn’t know at that time what it was, but I had to figure that out.

The second option is to sell. Of course, if you were to sell, 2021 was the peak of all times to sell. I did not go down that path. Multiples at the time were very high. I had a friend who got their business marked up five, six, seven times, which was way above at the time.

Alex: Is that EBITDA or revenue?

Justin: Earnings. Not EBITDA, but proper earnings. And it was an agency. So at the time you could have got a lot out of it. But I just remember seeing a good number of people, yourself included, where the post-sale founder conundrum was way too strong. And at that point in life I didn’t have enough other things solid that I could have that part of my identity change that quickly.

My partner, who at the time and up to now is the same girl, of course, we were only a year, a year and a half, into our relationship. It was a still new-ish relationship. We had moved to Australia in COVID, I didn’t see our future being there, and I wanted to leave. We didn’t have a physical place that we were super set on, and we didn’t have a future direction that we were super set on. And her work, she also wasn’t totally thrilled with. So without something else solid enough, I didn’t really feel comfortable having this also go up and out the window. That was my thought process at the time.

Alex: There’s some real wisdom in that, man. I think sometimes when there’s a heap of change going on around you, it’s quite easy to just go, fuck it, I’m just going to change this too. I know a lot of YOLO people, you know what I mean? And sometimes that works.

Justin: Yeah. So that left the third option, which was get a general manager. I think it was Taylor Pearson. I talked to him at the time and he suggested it. So I thought about it. Look, one, you can still sell the business in the long run if you choose to. I’m talking to myself in the third person. It would in some ways make it more valuable, if everything else stayed the same. And it may be a good middle ground. Worst-case scenario, if it didn’t work out, you would at least be probably six months removed from the business, so maybe you’d feel less tired, less burnt out, and you could give it another shot. One way or another, it gave me more room to think through how and what I wanted to do. That was essentially the thought process behind it.

Handing over to Fred, and getting it wrong (24:09)

Alex: I like the fact that you think forward in periods. You run that decision, you jump ahead, jump ahead. OK, where’s that going to land me? Where’s that going to take me?

The pattern I’ve seen with the YOLO folks, who I love, the YOLO folks are great because they’re just like, I’ll figure it out. It creates an intense amount of stress. If you’re focused and you like to hustle, you can figure it out on the way down. You jump out of the plane and pull your parachute on the way down, and realize you don’t have one.

The identity part you talked about, with the post-sale conundrum. Given that you’d poured so much time and energy and effort into Video Husky, after you brought in a general manager and got them onboarded, where did that leave you personally? How did you feel about that? Where did you start to spend your time?

Justin: So we hired Fred, I think, at the end of Q3 2021, around August, September, something like that. And in the first six months, basically, we got the transition a little bit wrong. I met with Fred every two weeks. It was the wrong system. What ended up working, ironically, was just meeting once every three months. Every two weeks meant he felt like he always had to report some kind of a win. I was kind of in the business, kind of not. It didn’t really work out that well.

One of the changes he wanted to make, which at the time I was very rigid against, was figuring out the proper holiday schedule. Are we following American public holidays? Are we following Filipino public holidays, which is where the majority of our editors were? Or are we doing some kind of hybrid? He made a big argument for it. A lot of our staff had wanted clarity about it, which I had always been against. I’d always just wanted free-float leave. I will give you more leave days, choose yourself. At the time I didn’t respect, oh, people want to do Christmas with their families. Very stupid in retrospect. You learn these lessons.

Alex: Yeah.

Justin: I guess this is part of it: I grew up in a family where Chinese New Year’s a thing, not Christmas. A little bit different. You know, be more respectful of these things. But he was a very big proponent for it and I was a very big proponent against it, and he got caught in the middle, essentially. In trying to make this change he had to try to explain my points of view to the staff, which he didn’t believe in, etcetera. I put him in a very difficult, unfair position.

So after talking about it, it was: well, I’ve got to get out of your way for you to do your thing. So we just said, once every three months, there’s a certain baseline of net profit that we want to see, and we just operate on that. And that’s OK.

Alex: Is he incentivized for performance? So if you do better he ratchets up, and if you don’t do so well he ratchets down, that kind of thing?

Justin: Yes and no. At the time we just said, if there was significant growth, call it a significant increase in net profit, I promise to revisit, and we can have a discussion. Which a hundred percent would be the case in my book. We were just going to let it be an open-ended sort of thing. But we made sure that the base wage was at a good place that everybody was happy with, so it wasn’t like he would be unhappy if these things didn’t transpire.

Letting go of the reins (28:12)

Alex: How did you feel letting go of the reins and handing over the baby husky? I’m trying to find a husky joke. I’ve been thinking about it for 15 minutes.

Justin: It’s so hard to think back and be objective about it, because it’s been so long now that Fred’s been in charge of Video Husky longer than I’ve been in charge of Video Husky. Looking back, I remember thinking it was difficult. Now it’s just so far away, or a much smaller part of my personal identity. I think it’s a better balance, at least on my part. It was harder at the time. You feel more pressure, but then as time goes by you hit kinks, the kinks work themselves out, and then it’s OK.

For my own situation at that phase of life, having Video Husky as a consistent presence in my life, albeit a much smaller one, and not having completely cut it off, I think is a much better outcome than had I gone down the sale route. Even if maybe financially it wouldn’t have been. I don’t know. But emotionally, mentally, identity-wise, it definitely was.

The post-sale founder conundrum (29:50)

Alex: Post-sale founder conundrum. That’s quotable, that one. That’s a good one. How much of that have you seen in other folks who’ve gone through it, or versions of it? Or just yours truly? And what did you take away from it?

Justin: You come to mind, obviously, because we’re talking now, but it was a good number of people I talked to for whom this was an issue. Dan Andrews and Ian Schoen talked about it, of course, at Dynamite Circle, and then one or two other people I forget. I just remember thinking I didn’t want such a big change. I just wanted room.

And now, nothing has really stuck. There’s been no project that, revenue-wise, has been, oh yeah, this is an instant hit. But on an individual basis, I knew I didn’t want to manage a big team. I knew I didn’t want to run an agency. Beyond that learning, I’ve wanted to become more technically proficient, which has happened, which is good, and I would like my career to go down that direction. But past that, that’s pretty much most of what I have to show for the last three-ish years on an independent basis.

If you’d asked me in 2021 if I wished I’d have more to show for it, definitely. But on the flip side, I’ve never had a crisis moment, because I always knew Video Husky was still there in the background. It’s both financial support and, not emotional support, I don’t know if that’s the right word, but an identity support. If it wasn’t there, I think you’d feel very differently. Or I’d feel very differently, at least.

Purpose beyond the business (31:52)

Alex: Yeah, the conundrum is real. I talked to Craig Hewitt yesterday. We were talking about exit, and I tried to put him on the spot and ask what multiple he would be happy to exit Castos for. He didn’t really have an answer, because he’s like, well, I actually just really like what I’m doing. I’m enjoying software, I’m enjoying these challenges. In his life phase, and with what he’s trying to accomplish, it fits. It just makes sense. I guess there are trade-offs between getting something to the position where you can actually let it go and exit it, and being exited.

The pattern I’ve seen emerge from folks I’ve reconnected with is about the people who seem to be on a path where they’re quite steady. I don’t know if they necessarily know what they want, but they’re looking for a broader purpose, some sort of impact they can have. Often it’s through their business, and because of their business.

Jake, from back in the day, I got to catch up with him. One of the things he got involved with: a couple of his staff members were right into ukuleles. They built ukuleles. But through COVID they couldn’t build them, because you couldn’t have any non-essential exports and there wasn’t any market. He loves music and he loves the craftsmanship, so he got in as, I guess, a bit of a silent partner. He was able to help them create an Etsy store, a site and some nice branding, and have that type of impact.

Is there a broader impact that you’re looking to have at the moment? Are you involved in anything that gets you fired up, or any places where you put your time or your energy? Because I know you’ve got your hands full, new bub, that sort of thing.

A year abroad, Age of Empires and New Zealand (34:05)

Justin: From that period I was still, of course, looking for another career direction. But a lot of it also boiled back down to personal things I wanted to do. I’m not going to pretend I’m some major sacrifice story, but I started working from a younger age, 17 or whatever. That was my first business. So I didn’t really do the end of high school right, and didn’t really do college right. I wanted to do a year abroad with my girlfriend, so we did that properly. Did some work, but nothing stressful.

For me, I wanted to do all that before we settled and had a kid, which we have now. You can’t do that ever again once you have a kid, or only much, much later on in life. I don’t know what kind of money I’d have to take in order to say, that experience is now taken away from me. It’d have to be an exorbitant amount, because you can only have that experience of traveling in your 20s in your 20s.

I briefly tried, I don’t even know if it was briefly, but I wanted to go pro as a gamer, for a very, very niche game.

Alex: What game?

Justin: Age of Empires. I played it during COVID. I’d played as a kid, and I got super into the competitive scene. I had nowhere near the amount of talent necessary to even get to the top, but I had a lot of fun. I know people say video games are video games, but I enjoyed it a lot, so I can’t complain too much.

And then after our year of travel we had to find a place to live. We ended up bopping around, came to New Zealand, really liked it, and here we are. I guess that’s home for the foreseeable future.

Talking to people, and I guess you’re less nomad-y, but people in Dynamite Circle, where there was more of a nomad-type background: there is a debt, there’s a cost that you pay if you want to go back to normie life. You save money on not having a car and not having furniture, etcetera. I’ve got a backpack. But once you do settle down, all of a sudden you do need all those things. So you’re rushing to make decisions. OK, the car. OK, get a dog. OK, get a desk. Well, if I’m going to settle down, I want a nice desk. I want one monitor. No, actually, now I want two monitors. Actually, I want a standing desk and I want a nice chair. You think, oh, I’m not going to travel any more, then I want all these other things.

So the 18 months, I think it’s two years now, that we’ve lived here, it’s been maybe not a sprint, but a very high-intensity run, with a lot of personal stuff coming up, and just trying to manage all that.

Why coaching didn’t fit (37:24)

Alex: And so what are you doing these days? I know we talked about this in email, but where are you spending your time now?

Justin: I’ll back it up to 2022 to 2024, just briefly. I didn’t want to take on anything stressful, so I thought, oh, maybe I’ll just do some consulting, coaching. Did that. Did not enjoy coaching. Didn’t like it.

Alex: Tell me about that.

Justin: A lot of the challenge with coaching, at least for me, is that post-COVID the entire business landscape shifted. A lot of the arbitrage opportunities that were available pre-COVID are no longer there post-COVID, just through the sheer amount of competition and people coming online and working in that way. What was once a huge arbitrage opportunity, everybody’s figured out, from a cost of labor perspective, to Facebook ads getting more expensive, to Y Combinator companies going after the most basic software businesses now. A lot of the meat has already been eaten from the bone.

So it’s very hard to say, oh, I have this experience. Which is true, but number one, a lot more people now have the same experience. And most importantly, because the landscape shifted, everybody’s fishing out of the same hole. There aren’t going to be that many fish left. So I felt less comfortable doing coaching, because I couldn’t say, oh, well, I did this, so I can guarantee the same results. And I don’t really feel comfortable otherwise. Versus with a video, yes, I can’t guarantee how many views you’ll get on your video, but I can guarantee you’ll have a video at the end of this. So coaching and consulting wasn’t really the right fit for me.

A marketing job, then learning to code (39:32)

Justin: I then did a kind of extended stint at a friend’s company doing their marketing, first part-time, then for a very brief period full-time. It wasn’t really quite the right fit. I really like the guy, but it wasn’t the right interest area, and I don’t think the growth potential was as much there as we originally hoped. So I left that at the tail end of last year, quarter three.

And from maybe halfway towards the end of 2023 to the beginning of 2024, I started learning some basic programming. You start with HTML, a little bit of CSS, CSS became Tailwind. From there it just felt like a much better direction for me. Granted, this is right before vibe coding became a thing, so I don’t know how that plays out. Maybe there’s a lot more competition there, and that eats away at you. But it felt right.

Before leaving that last role I talked to my uncle and I said, look, I have these new random skills that I want to work on and test out. So I’ve been building websites for a few of the organizations he’s affiliated with, and helping grow one of their organizations’ YouTube channels. That has been a very interesting experience, being on the other end of Video Husky, since of course I hired our own people. But yeah, that’s mostly been it.

Betting a career on the next thing (41:13)

Alex: And in the future? There are lots of different pathways, if you wanted to go technical and work in a company, which it sounds like you tried a little bit. Do you have a view of where to from here?

Justin: I think my own personal desire is still, in the long run, to own and run a one-person, solopreneur, or at most small-team software product. My own personal strengths come from systemization, workflow optimization. It comes naturally to me, so I would like to work more in that area. And becoming more technically literate was the right thing to do for me.

The best example with something like vibe coding is that vibe coding is kind of like an iPhone. All of a sudden everybody can take better photos. But just because you have an iPhone doesn’t mean you stop hiring photographers. Nobody’s going to use an iPhone for their wedding photos. So I would still like to be technically proficient, even further than I currently am.

And over the long arc of a career, I’m 31 now, so call it another 35 years, there’s a lot of change to happen in the future. I think there’s a lot more that will happen in an online, AI-type space. Even if the competition is much harder and the arbitrage opportunities are much fewer, I think I’d like to spend most of my career gambling on the next thing, and the next thing, and the next thing.

Which is not advice I would give to most people. But all things considered, I have Video Husky, and you play it safe, play conservative to an extent, you have savings, and you can keep your own runway low. In my case I also have a very supportive family, and that goes a long way. With all these things, I would rather take those bets, because your outsized outcomes could still be 100% worth it, even if the chance of success isn’t high. That’s the direction I’d want to go down.

Freedom lines and defining success (43:40)

Alex: Maybe it’s a leading question, but when you think of an outsized outcome, is that in terms of personal growth? Is that in terms of revenue? What is an outsized outcome?

Justin: Revenue, of course, is one frame of it. One part of it is net profit, etcetera. But in terms of money, I think Dan and Ian talk about the freedom lines. Your freedom line is where you can go out to a restaurant and not think about how much you have to pay, or you can take any flight you want without thinking about money. Once you’ve crossed that freedom line, the next one is that much further away, right? Because the next one is, call it, somewhere between five and ten million, I think, for most people when you think about that kind of stuff.

That’s going to be a while away one way or another, so it’s not a rush to get there. If that ever happens. Maybe it doesn’t, and that’s OK too. But I could keep on trying to do something that I think I would like to do, which would be to build something out. I think it’s defining success in your own way, for lack of a better, less cliche way of putting it. I think that’s how I’d like to put it.

Advice to his younger self (45:15)

Alex: You’re a natural coach, dropping lines like that. All right, to round up the questions here. If you could talk to the Justin of way back, when you kicked off Video Husky, what advice would you give him, if any? And do you think you would listen, or would you just have to muddle through and figure it out for yourself?

Justin: I’d like to think I listened to you a fair amount.

Alex: You actually did. You were very coachable. I was always very excited to jump on our convos, because you would execute and you would learn and you would reflect, and there was plenty to work with. The people I would get frustrated working with sometimes were the ones where you’d have the same conversation week in, week out. At a certain point I’m like, you’ve just got to take an action, make a decision and learn from it. So in that regard, man, you were a dream. So much fun.

Justin: So much easier when you’re younger.

Alex: Yeah, you’re malleable, and you’re willing to be challenged and willing to learn, and there’s maybe a little less ego.

Justin: All right. I think two things, maybe, if I were to give advice to self. The first is, and maybe this is a dude thing, or more an ambitious dude thing, but there really are things that are worth more than revenue goals or success targets. It’s easy to think there are things that you just take for granted, that will come naturally in life. Oh, you’re going to have a wedding, or you’re going to have a life partner, or you’re going to have kids. I literally just took those things for granted when I was younger. It was going to happen sometime in the future.

In my case, I guess we’re not married, but we’re long-term committed partners, with a kid, with a dog. And now it’s like, oh, you can’t take those things for granted. I met my partner in a bar in Cambodia, and I don’t drink, so I don’t understand why I was at the bar. If I was there an hour earlier, or there an hour later, it wouldn’t have happened.

We’ve talked about it, especially since having a kid. I think in seven out of ten lives I don’t have kids, because it required meeting somebody like my partner. She’s just a very, very, very caring person. She will take the lead on this, and she’s just a loving person. And I don’t really have that. You know what I mean. It’s not my most natural forte. So it required meeting somebody who could do that, and I think it’s very easy to take all that for granted.

So that’s the first thing. What is tangible isn’t always the most valuable thing. And you see enough long-term relationships not work out that you go, ah, it’s not easy. It’s really, really, really not easy.

If you always need to win, you win small (48:58)

Justin: And the second, I think, is that there isn’t necessarily one definition of success. There are multiple paths that you want to consider. Then you also have to know that things come in waves. If you need to always feel like you’re winning, then one way or another you’re always going to be winning small, because you can’t have the time to invest in something big. I don’t know if that makes sense.

Alex: Play it back to me.

Justin: All right. OK, let’s use poker as an analogy. If, in your head, in order to be a good poker player you need to be winning a hand every 10 minutes or whatever, you need that reinforcement, then you’re always playing. The problem with always playing is there’s a chance you’re always losing, because at the end of the day the majority of hands you get are going to be crap. But if you’re patient, and you wait for the right opportunity, and you can build up for that opportunity, the one that is uniquely suited to you, then I think your likelihood of success is much higher.

I think this is where post-sale founder syndrome gets a lot of people in trouble. Even myself, to an extent. After leaving Video Husky, what did I do? I took, I don’t know, 15, 20K and sunk it into a bunch of random crypto tokens and whatever you want. Thank God it was only 20K. That could have been worse. Imagine I’d sold the business. Maybe it would have been 200.

You always need to go from one thing to the next thing to the next thing, and that can get you in trouble, because then you’re only seeing what’s immediately in front of you. The people who won out in the NFT, crypto craze of 2021 were the people who had been there since 2017. So if you’re properly thinking through your career and the long arc of time, you cannot always be winning. By definition, that can’t be the right way of doing it, because you have to know when the right waves are to ride. And in order to know when they are, you almost have to be wrong for a long enough period of time, because everybody will look at you going, what are you doing? I’m sure there’s a more eloquent way of putting that.

A little bit of money gets you in trouble (51:40)

Alex: The way I would frame that is that there’s a level of, excuse me, either unhinged or borderline insanity for founders who are doing something very far out, because they can see something that’s not there. In regular life, and I’ve had experience with this, if you’re seeing something that’s not actually there, then by definition your view of the world is warped for some reason. A founder who’s got this vision that’s 10, 15 years out, and they think they can see what it is, the level of conviction you need to have to accomplish that, by definition there’s a bit of insanity to it.

The other thing you touch on, and I think you’ve got the wisdom around this, is that there’s also a sense of a bit of a Midas touch. If you have a win, you think you’re kind of smart, and then you go into a different market, or a different vertical, or something else. It’s like, well, I can bring my skills to bear on this thing, and because I’m accomplished and I’ve done some things before, I should expect a similar level of success. Which I think is also a little bit of a trap.

Justin: Yeah, and I’ve seen that a bit. Think about it in terms of, again, going back to the ladders of freedom, of money. If you have no money, you have nothing to lose, so you don’t have to think about it so much. If you have a lot of money, assuming you’re not stupid, you’re also good to go. The challenge comes when you have a little bit of money. A little bit of money can get you into a lot of trouble. Look at the majority of people in Australia and New Zealand with their mortgages and leaky homes. You think you have something, but you can only gamble with a little bit so many times before you’re entirely in the red.

I think that’s also a post low-seven-figure founder challenge. It’s not quite enough to get you over the line, but you also don’t have the mindset of, oh, I can just go live in Thailand off a grand and a half a month and live very, very comfortably. You end up in this middle area, and if you’re not careful with that, it can go south very quickly, I think.

The next best thing, risk adjusted (54:33)

Alex: At least in my experience, I try to be honest about what I had on deck. If I had something compelling, and for me that was conviction, if I had high conviction I would relentlessly pursue it until that vision came true. And when you’re in the trough of that wave, and there’s nothing that’s really that compelling, and you don’t have that conviction, my point of view was: what’s the next best thing I can do, risk adjusted?

Justin: Yeah.

Alex: For me at that time, I coached for 18 months, two years, and I started to burn out on it, because I was just telling the same stories over and over again. I was repeating a lot. I almost needed a play button to tell this anecdote. I’m charging people a lot of money, they’re getting value, but internally I’m going, well, I’m not showing up 100%, and it feels disingenuous.

So what’s the next best thing? For me it was, OK, what would be the best company to work for where I could learn something? That’s how I ended up at Canva. Brilliant product, growing like a weed, those sorts of things. But then I get into it and I’m like, oh shit, I’m a terrible employee. I’ve made a huge mistake. But at that time, in that season, that was the next best thing I had on deck.

Sometimes it’s hard to look at these options. You almost want to will it to success. I’ve had a few half-baked ideas on different products. I had a look at a startup in the AI space, even went out and pitched some VCs, and I’m like, I’m not built for that. Getting rejected 20 times in a row on a concept where neither of us knows if it’s going to be true. I agree with all of your points. It’s whether you want to back it. But there’s some good stuff in there about recognizing where you are on the wave.

Eight months of live poker (56:46)

Alex: The other framework I think is interesting: there’s a guy, his name is Billy Murphy, and there’s another dude, Todd Tresidder, and it’s a gambling framework, EV. I think it’s expectancy value, or expected value. It sounds like you play a little bit of poker?

Justin: Another small phase of life. I ended up playing a good amount of poker here in New Zealand, because the New Zealand dollar’s cheaper than the US dollar. That was also a very fun time.

Alex: How’d you go?

Justin: I went pretty well. But again, you can’t make a career out of it. Or you can, but it’s very incompatible with family life.

Alex: What would you have to do to make that workable? Is that face-to-face, you’re playing tournaments and those sorts of things?

Justin: You’ve got two options, I guess. If you really want to do it, you have to do it online. You play nine tables at the same time, and then you’re just sitting in front of a computer grinding. If you want to do it in person, you play that many fewer hands, and that many fewer hands means your earnings are going to be lower. If you’re a good player, over a long arc of time you can expect to earn, I don’t know, five times the big blind. So if your big blind’s three bucks and you’re doing well, you’re earning 15 bucks an hour. So it’s also not really quite there. But it was a lot of fun.

Alex: How long did you do that for?

Justin: Maybe eight months, I think.

Alex: That’s a pretty decent stint. That’s a good nudge.

Justin: Yeah, that was two, three times a week at the casino, not that far away from here. I only did it in person. I didn’t do online. It was just for fun. At least I came out quite a bit on top. But quite a bit on top is like $2,000. It’s not life-changing or anything. But it was very enjoyable, and at least I can say, oh, I tried that, enjoyed it, it wasn’t the direction I wanted to go down, but it was a lot of fun.

Where to find Justin (58:58)

Alex: Cool. Well, I think that wraps it, man. That’s been so cool. I definitely read your blogs. If they’re still around, where can people read about you or connect with you? Are you still writing? Still posting stuff? What are you doing?

Justin: I did do a bunch of Twitter posts for a while. That also wasn’t the right fit. I guess that’s the thing: you just keep on trying random things. Going back to the poker, you have to keep trying and you have to hope something works out.

I don’t know. I still want to hear about how you ended up at Canva, and going to China to work. I couldn’t do that, and I’m Chinese.

Alex: When we wrap this recording we’ll keep the convo going, and I’ll give you the inside scoop on that. So to answer that question, people can’t find you online? They have to come to New Zealand to find you, or what?

Justin: I still have my website online, justintan.me, but I haven’t written on it in years now. Eventually, maybe at some point, we’ll redo it.

Alex: I’m flashing back. I’m having a bit of a moment here, but I remember you writing. Doing the personal writing was, at one time, the thing that was a priority for you. You wanted to create some space to be able to work on that.

Justin: Yeah, I did that for a while. That’s the thing: you try anything for six months, three months, call it, and if it doesn’t stick, then it’s OK. You tried it, and then you can move on.

Besides, I don’t know if you can see her, but I have a very, very sad dog that requires a lot of attention. See, she’s black and it’s dark over there. She’s in the shadow. She takes up all the leftover attention nowadays.