#181 - Engineer Your Career and Your Life: Timeless Career Advice and the Power of Small Bets - Louie Bacaj

[00:01:44] Introduction

Henry Suryawirawan: Hello, everyone. Welcome back to another new episode of the Tech Lead Journal podcast. Today, I have with me someone who is quite around in Twitter, right? Quite famous in Twitter. I have Louie Bacaj here. So his story and his career actually is pretty interesting. And today, we’re going to learn a lot about his story and journey, and hopefully we can learn some insights on how we can also utilize those stories into our career. So Louie, welcome to the show.

Louie Bacaj: Very glad to be here, Henry. Thank you for having me on. Excited for this conversation.

[00:02:14] Career Journey

Henry Suryawirawan: Right. So Louie, maybe in the beginning for those of us who probably haven’t heard about you yet. Maybe if you can do a short intro just to let people know who you are.

Louie Bacaj: Sure. So I’ve, I had a sort of decade plus career in tech. I started out as a individual contributor, sort of junior Java developer, and then climbed my way up to senior director. I worked at startups, venture backed startups that raised close to a billion dollars and grew like crazy. And I worked at big companies. One of the startups I was a part of was acquired by Walmart. I actually got to running their pharmacy tech there. All the modern tech in pharmacy. Very, very large team. 35 billion business for Walmart. And, you know, but I worked at Bank of America, a lot of places in that almost 15-year career. And then I left all of that behind right after the pandemic at the end of 2021. And I decided I’m going to chase my dreams of entrepreneurship and try to fend for myself out there. And that’s how I got into sort of placing small bets. And it’s sort of been my strategy for entrepreneurship over the last couple of years. It’s working out pretty well.

Henry Suryawirawan: I think hearing just your intro, right? Some people would find it really interesting and can relate to their career. So some of us work in big corporate. Some of us work in startups or, you know, like scale ups, right? And some of us also do some kind of consulting and entrepreneurship. So I think we’re gonna cover as best all of them as possible.

[00:03:36] Big Corporate vs. Startup

Henry Suryawirawan: So maybe in the beginning about your career, right? You seem to have worked in multiple types of companies like big corporates and also startups. So for people here, sometimes I can hear people asking what’s the difference? Maybe in your view, what will be some of the big key differences working in corporates and startups? And what do you think are pros and cons of each?

Louie Bacaj: Yeah. This is a great question. I mean, obviously I could go at length at this, but I’ll try to be concise and just give people a couple of quick nuggets. I think startups are about speed in my view, right? So if you join a startup, whether it’s venture backed or you’re doing it for yourself, you got to move fast. Quite often, you hear this saying, you know, move fast and break things. It’s true. You got to be able to move fast, build things, sort of plant these flags and take these little new beaches, and be comfortable with technical debt. Be comfortable that as the startup grows, hopefully, if it’s working out, you get the opportunity to go back and repay down that technical debt and take care of all of that.

Big companies are very different. It’s more about collaboration, working well with other people. It’s about making sure you’re not wearing a lot of hats. You get your little corner. And you’re trying to make sure that you write the best code possible. You’re trying to make sure that it’s extensible, that other people can work with it. These are the people that clean up the stuff that the people in the startup did after the acquisition, you know, the big companies, that is what they do. And, you know, a lot of times, startups have the opportunity to become big companies and they get to clean it up themselves, which is even better. But generally speaking, I think that’s sort of the major difference.

And in terms of, I think career progression, you end up moving a lot faster at startup. Especially when things are working out well, you’re wearing a lot of hats and you get to choose, in fact, you know, what you like more. If things are working out at some point, you get to choose whether you want to go into management, because they’re desperate for people in various areas, when things are working out. When things aren’t working out, the learnings I would say are still pretty good at startups. But, you know, obviously the money might not be as good if things don’t work out.

One of the nice things about big companies is you get a very, very steady paycheck, usually, at market rate for most of the bigger companies. But, you know, you progress a little bit slower, both because you’re not wearing a lot of hats, but also I think, they’re already pretty set in terms of organizational structure. And so you need the room to move up. You need some opportunity. Whereas in the startup, I mean, every other month there’s some new opportunity. And so I’d say these are the major differences. I could keep going, Henry, but I’m going to stop right here, I think, on this one.

[00:06:02] Wearing Multiple Hats

Henry Suryawirawan: Right. So there are pretty interesting points that you raised just now. So one thing in particular that you mentioned quite a number of times is about wearing multiple hats. So I think for some people, this can be a struggle or a challenge as well, having to wear multiple hats. So tell us what are some of the biggest challenges when you work in the startups and you have to kind of like assume multiple hats and have to, maybe, learn as you go as well, right? Because most likely, you may not be exposed to those kind of things before and you have to learn and do at the same time. So maybe a little bit tips on this part.

Louie Bacaj: Yeah, I mean, most software engineers, especially like on the junior to sort of mid levels side, I would say, are pretty used to having tickets broken down, having things handed to them, being told, look, this is what you need to do. And you go off and you do that. I mean, in a startup, stuff like that is a lot rougher. You might not even have a product manager.

For example, I was at a company called Jet. And the CTO came to me and said, look, the marketing team, the marketing function of the business, need help. They need to build some tools because they’re doing a lot of, they’re spending a lot of money on advertising. It’s very inefficient. They’re sending emails, but they’re like double emailing people. They’re doing all kinds of crazy stuff. It’s really bad. And we in engineering have to help them in some way. There was no product manager. So now you have to act as the product manager interfacing with this business unit, trying to figure out, okay, what do you need exactly? How do we break this down into something that we can deliver in the next month or two or whatever it is?

And then, you know, if it turns out that it’s really big, you now need to like put on your manager hat, go back to the CTO and say, I need more help. You know, like, the scope is huge. If you want to support it, maybe we could do it. Or maybe we have to like cut this down and figure out a way to give them something much smaller. So these are the sorts of things that, I think, you end up becoming a manager, you end up becoming, you know, you become your own manager, you become your own product manager, and your own engineer. All in one package. And you got to try to deliver something that works and adds business value. And if you can do that, I mean, then the sky’s the limit. Because you’re picking up all these various skills. And it’s actually very, very valuable to the market, obviously, almost anywhere. Even at big companies, they value that kind of experience. You build up a lot of sort of tacit knowledge, stuff that you can only acquire with experience. So I don’t decide. That’s what I’d say about multiple hats, Henry. I don’t know if I missed another part of that question.

[00:08:18] Self-Upskilling Rapidly

Henry Suryawirawan: Yeah, I think that’s kind of like sum it perfectly, right? Well, one thing maybe I could just add on is how do you upskill yourself that fast, right? Because sometimes you may not have peers who can actually tell you what to do or coach, right? And you have to do it all by yourself. So maybe how do you upskill yourself? Maybe looking back from your story and journey, right? How do you upskill yourself?

Louie Bacaj: This is… This is a great question. And I think you sort of need to look for mentorship. You’re sort of grasping at straws, almost, I call it. You know, you’re just grabbing wherever you can, whatever you can, because you need it. For somebody who doesn’t like that type of pressure, it can be very difficult. I mean, you know, I was reading books, frankly, on both product management and business and marketing, because I was interfacing with these people in marketing. But some of the business leaders in marketing, specifically this one woman that ran marketing, she ended up becoming an amazing mentor for me that I used her tactics that she used to manage her people and her business to manage my engineering teams later.

You know, so I was learning from her. I was learning from my CTO, from the EVP of engineering. I was going back to people in the product organization who were very busy and just saying, look, can I pick your brain about this? The business wants these three things. What would you do? You know, like just, you know, I have to make a decision. I have to build one of them. And, you know, and so you’re grabbing these information. And it can be very overwhelming. And, you know, frankly, looking back, I worked some crazy hours to achieve all of that. I wish I could just tell you just do one, two and three and you’re just going to do all of this. But actually, I was working like 12 hour days for like two years. And, you know, I’m very fortunate because it worked out. But if you imagine doing that and then it doesn’t work out and then, you know, I mean, of course, you still gain the skills, but you don’t get the rewards.

And so it can be a risk that you’re taking. It’s a decision that you’re making at that point. Number one, you’re making a decision, you’re taking a risk by going to a startup. Number two, now you’re taking a second risk because you’re foregoing some of your personal time to keep working late or whatever it is to acquire these other things that we’re talking about. These other hacks that you need basically to do the job right. And so these are all things that people need to make the sort of trade offs that they need to make themselves. It’s not something that I could tell them what to do, but this is how I did it, you know.

Henry Suryawirawan: Also, I think it depends on the culture of the company, right? Whether they tolerate mistakes or maybe a time for people to learn and upskill themselves. So I think this is also definitely very relatable to me, because there was one time where, when I work as a consultant, right, I didn’t know exactly what was assigned to me. And I have to kind of like learn one day before I pitch it to the client. So I think this kind of situations always crop up, especially technology now moves very fast. So I think it’s pretty difficult to know exactly what you’re doing.

[00:10:56] Louie’s Rapid Career Progression

Henry Suryawirawan: So one thing that I look at your career, you seem to have a progression really, really fast. It was even covered in Gergely Orosz’s newsletter once. So I think you climbed up from like a senior engineer up to senior director within about 8 to 10 years. That was pretty fast. So maybe if you can look back and tell us that story, how do you actually made it so fast?

Louie Bacaj: Yeah, Gergely has a wonderful newsletter, The Pragmatic Engineer. I’m a huge fan of this one for software engineers. Every piece is like sort of timeless. And he went in depth and, you know, one of the interesting things that sort of the first five years or so of my career were actually, I’d say, pretty average like I said, junior Java developer. Then sort of a mid level engineer and then senior engineer. Nothing out of the ordinary for the first few years. I would say I got the fundamentals in right. I even went back and did a master’s while I was coding for, uh, I think Bank of America at the time. So I worked at a couple of different companies as an individual contributor primarily. And then I sort of went to the startup. And, you know, the startup took off like a rocket. I mean, it did really well.

Within a year, we had 10 million customers on this e-commerce site. And we had to build this thing from scratch. This is in 2014, 2015. It wasn’t as easy to build scalable systems back then. Azure had just launched. It was just kind of getting going. It had a lot of issues, for example. AWS was there for a while. But we were sort of trying to compete with Amazon, so we weren’t trying to build on their platform. So we had to figure some things out in this startup.

But the point is that I caught a wave. You know, I caught a wave, I think, in terms of that, in terms of that progression. But I also leaned into the wave. And I think this is really important because, you know, you could have a wave and just choose not to surf. You know, you could… You know, I mentioned that I put in those crazy hours at that time, because I saw the way it was going. I could see every week there was tons of new customers. So this means that this is working. So this means that my risk that I’m putting in is probably going to pay off on the other side. I mean, the probabilities are good. And so I’m willing to take that risk. And I was sort of at a point in my life, I didn’t have kids yet. I actually had my first kid while I was working at that startup.

But, you know, so I made these trade-offs, my wife and family, and I decided, look, I’m going to lean in for a year or two. I’m going to see what happens. It may or may not pan out. And in those two years, I’d say I probably got more, more experience in those two years than most people get in, you know, five, six years. And it’s just because the timelines are very compressed. I was working 12 hour days. I was building like crazy. And then six months into it, I’m going back to the CTO and saying, look, the only way I can deliver all these things is if we hire a couple of people. So then I’m hiring and I’m growing a team. And then after I’m growing my first team, things are going really well with that. Then now we have a second and a third team. And then now it’s, you know, after that we got acquired by Walmart. So we layered even more teams and we had a much bigger business. These are the things. I caught the wave. I decided I’m going to surf. And I leaned into it. And it just you know, it just sort of took me.

But I think people need to make these decisions, sort of. If you have no opportunity where you’re at to grow, and you see that there’s no opportunity, it doesn’t make sense to put 12 hour days, 14 hour days. Again, it’s a personal decision that you need to make. There’s other factors you might consider. But for me, the opportunity was there. I felt like I’m an immigrant. You know, I was hungry. I decided I’m going to grab this bull by the horn and see where it takes me. But yeah, so I don’t know if that exactly sort of answers it, Henry, but it was basically a little bit of luck, and being at this startup that was taking off. I sort of consciously made the decision to join this startup.

I actually took a pay cut, a small pay cut to join this startup, because I thought the learnings were going to be really good. I felt like, okay, I’m taking a risk and if it works out, it might work out really well. I liked that the founder had already had multiple successful exits. I liked that they had capital. I liked the tech stack they chose. There were so many things that I liked about that, that gave me confidence that this is probably a good path. And then I decided to take the risk, but it was a very conscious risk. And so I did get a little bit lucky that it worked out, but I also chose to lean into it. So I’d say those are the two key sort of components. You need to get a little lucky and you just need to put in the work, you know.

Henry Suryawirawan: Pretty good insights. I think first you need to have the opportunity, of course, right? You need to be able to be there when the opportunity comes. And then I think the second thing is very, very important, right? Lean into the opportunity because sometimes some people have the opportunity. But they actually, maybe they have no interest taking a new role, wearing multiple hats, or whatever that is, right? So they decide not to surf, like what you said. So I think leaning in is definitely key.

Louie Bacaj: Yeah. I think sometimes they have the opportunity and it’s not like they don’t want to, but maybe they can’t. They’re not in a point in their life where they can take advantage of it, you know. And so there’s many factors unfortunately that go into it. But I think if you have the opportunity and you see the odds are good. And it’s all about odds, you know what I mean? Even the small bets stuff that I’ve been doing, I just, this is how I think about things. Like, what are the odds that this two weeks of work that I put into this thing is going to pay off? And then I make the decision whether I’m going to do it. I think people need to do that. Like what can they risk? What can they afford to risk their, you know, nights and weekends or whatever it is. Obviously, that’s a personal decision. You know, it’s not easy to make that decision.

[00:16:00] Getting Comfortable with More Senior Roles

Henry Suryawirawan: So one thing I think as you progress very fast, right? You go from IC to management. And I think there are many challenges when you transition from being an IC into management. And even you seem to take like more senior director role, something like that. The job can become really more abstract. And some people find it also challenging to actually know what they should be doing at that level. So maybe from your experience, how can you suggest people to probably do better in terms of working with more abstract stuff, even finding the problems to solve, managing people, and things like that?

Louie Bacaj: Yeah. I mean, it definitely becomes more abstract. And now it’s a very different job. I would say once I had sort of two levels. Once I was manager of managers, it was totally abstract. I mean, you’re so disconnected from the code, basically that you might as well be on the moon, you know. So it’s a totally different job. It’s a people management job now. And, of course, you know, that has its own risks, right? That has its own risk, because most of the, you know, at least in our field, most of the people that go into these jobs used to be engineers. Now those skills atrophy. We’ve seen layoffs, especially at the management layer where people want flatter organizations, less managers. So there’s all kinds of trade offs with making this decision.

But I would say if you make the decision to go down this path, then you have to lean into it. You have to get good at it. You have to read the right stuff on it. You have to build the right skills. You have to build the communication skills, you know, Being heads down and programming is a very different thing than negotiating for headcount, negotiating for your people to get promoted and helping people progress in their careers, caring deeply about people. It’s a very different thing. And so I think, you got to lean into the thing that you chose, right? Whether, you know, I mean, if it turns out that you don’t like it, then I think you should reverse course and do the thing that you like and the thing that you’re good at. But if you do do it, you obviously have to try to pick up as much as you can all of the different sorts of things.

I would say, you know, some things that help make it less abstract is that, you know, I saw a lot of people going to the sort of director and senior director and EVP, CTO, whatever, and they didn’t… They just spoke to the people that were under them. I think this is a huge mistake.

I mean, you know, I hate to make comparisons between organizational management and like military and stuff like that. But there’s some lessons to be drawn there. They’re really good at managing people in the military. And so, the thing that some of these generals do, you know, they don’t just talk to the people that report. They go talk to the soldiers on the front a lot. And so I think it’s really important that you don’t lose that, that you somehow keep one-on-ones with people that are even two levels below you, right? And even if you’re the CTO and it’s four levels or five levels below you, you should still pick a few of them. And once every six months, once every year, speak to them, you know, and I think it’s really important.

Even if you’re just having coffee. Even you’ll be surprised what kinds of things you find out. That was one of the things that I think helped me immensely. I basically took people out for coffee and I bought them the coffee. So I just, I think I had one of my junior engineers once tell me, you know, you take out like 20 people a week for coffee. I’m pretty sure you’re spending like 2,500 out of pocket on these coffees every, you know. I would take one or two a day, every day out. And we would just talk on a coffee walk and talk. But they would, I would, I’d say it’s totally worth it because you’re spilling all the beans. Now I know exactly what’s happening with this project. I sort of knew, but now I know, you know, there’s no question in my mind about how it’s going. Even, I’m in the meetings with the business and the product and all of that. But now, you know, I also know what the person in my org on the ground is actually blocked on or struggling with or what they need help with. This was immensely helpful to me.

So that removes a little bit of the abstraction. It’s impossible to get rid of it entirely just because you’re not doing the work yourself. But I think it’s actually very, very helpful to keep those things going. And in fact, one of the things I recommend to people a lot is, you know, not just talk to people that report to you or level below you, but even, you know, set up one-on-ones with people in the business. And of course, now you’re talking a lot of one-on-ones, but you don’t have to do it every week. I mean, you do it once a month. And it’s just the relationships that you build, even again, even if you’re just having a cup of coffee and a walk and talk. The relationships you build, you never know when you’re going to have to negotiate on something. You never know when you’re going to need help. You never know when you’re going to need support, you know, for a project or to pay down some tech debt or whatever it is. Those relationships end up being immensely helpful or support for a promotion. You know, like having someone on the business, support your promotion is huge. I used to recommend this stuff to my reports as well. It wasn’t just something that I did. It’s something I told them to do. You know, you’re talking to me. Have you had a one-on-one with your business partner? Like, you know, take them out for coffee. You can just spend the 2.50 or 5 dollars on them, you know. But yeah, I think you’ve got to find ways to remove that abstraction, basically, Henry. It’s not a freebie.

And one other trick that I sort of I’m lucky I did, because I feel, you know, I was probably, you know, I was probably lucky, my career, I moved into management pretty quickly at Jet and then it just went from one level to two levels to a manager of managers very, very quickly. I never lost the coding skills. You know, I always kept them. Maybe if you put me on the team, I was like one of the worst engineers. But, you know, at that point, when I was a senior director with like tons of reports, but I could still code. I mean, I could still look at someone’s pull request. I could still see what’s coming in. I could still understand the system. I could understand the architecture. I could understand these things. You never want to lose that stuff entirely. And it’s very easy in big companies to drop that stuff. And I think that’s a huge mistake, basically, for senior directors and above to lose sight of that because that’s the stuff that’s actually you’re responsible for whether you like it or not. You know, even though your job is people, they’re still going to blame you if the system goes down. You know.

Henry Suryawirawan: Yeah, exactly. So I think being still hands on, I think it’s very, very important, no matter what kind of levels you are, right? Especially the fundamentals, right? Because these things maybe rarely change. The architecture, the design, scalability problems, and things like that. So definitely being hands on. And the other one I like is like building relationships, right? Not just, with the people that you are very close with, but sometimes with your skip levels, with your business stakeholders, and things like that.

[00:21:55] Tips on People Managementx

Henry Suryawirawan: So managing people is also one aspect, very, very big when you go into that management role. So if you can give maybe some tips, like what worked for you when you manage people at that point, right? Especially you manage not just one team but multiple teams within the organizations.

Louie Bacaj: I’d say there’s a couple of things. If some people might not like hearing this but, you know, obviously, hiring great people is a huge. You know, you show me your friends, I’ll show you your future. But this is like especially true for colleagues. Even the people that are under you, you want to have a say, even two levels below you. You want to be in the interview loop. You don’t want to drop off. Just, it’s too easy to drop off, in fact. But you want to have at least a small conversation and understand who they’re hiring and why they’re hiring them. And I always loved hiring just great people that I was certain that they were going to make some sort of impact and add value. And then maintaining those relationships is really, really important, right? Having good relationships with people below you, to the side of you, above you, everywhere in the org that you can sort of muster them.

And then there’s a third point that I wanted to make. Fighting for people. And I saw so many people mess this up. So many people in leadership mess this up. If someone has done their part like they have gone above and beyond for your organization. And now it’s time to come the calibration meeting, or you have to have them promoted. Organizations can only support so much promotion, right? And so it’s going to be your person or someone else’s, and they’re going to put everything on the table and say, well, you know what, this person deserves it more. I mean, sometimes you got to really go to bat for your people, especially when they’ve done what they’re supposed to do. This has almost never failed me.

And I am…, especially when I believed that someone did the things. And I mean, I fought. I screamed at people. When you do that, you’re risking in a calibration meeting with lots of other directors and stuff like that, you’re risking your reputation by doing that. But you have to put it on the line. And the thing is like, if you don’t do that, then don’t be surprised when people leave you. You know, they’re not growing. If they feel like they’re not, don’t be surprised when they leave you, don’t be surprised when they check out, don’t be surprised when all the bad things that can happen in an organization start to happen. I mean, you know, you have a lot of roles as a director, senior director, but I’d say the thing that’s most useful to your team is for you to go out and get them the things that they need, the resources that they need, but help them with their careers, especially when they do their part.

And so this, I think, is a huge one should not be taken lightly, especially for people that go into management. A lot of engineers that go into management naively believe that there’s no politics, you know. Everyone’s just going to do the right thing. They’re used to code, right? The code executes one, two, three, it jumps and then comes back around. It’s going to behave the same way every time, right? And so the naivete is, okay, these are smart people. They used to be engineers themselves. They’re going to do the right thing. And my person is going to get promoted. And so they don’t fight that hard. They think it’s just a matter of executing the program.

No, no, no, no, it’s not. Now you’re dealing with people. Now you’re dealing with leaky abstractions. Now all kinds of things can go wrong. All kinds of unexpected things can happen. And if you don’t do your part to handle every possible edge case that just pops up randomly right in front of you, then I think you’re going to fail. What’s going to happen is, you know, you might be doing everything right in terms of what you’re telling people to do, the way you’re managing them. They might have great clean code and then they still leave you. Why do they leave you? Well, because they can’t grow. Now you’re a manager, now you’re responsible for their career. If you don’t do that part, it’s like a chicken that doesn’t lay eggs. It’s no good, you know.

Henry Suryawirawan: Right, I love that analogy. So yeah, I think definitely very, very important. Very true to me as well, right? So when you go into management, not only it becomes more abstract, but some kind of politics and maybe bureaucracy will be something that you need to deal with, right? Because that’s how the management and the organization works, right? So maybe in a small startup, it is less pervasive. But I think in the bigger organization, even though it’s just like a hundred people, right? There will be definitely this kind of things.

[00:25:41] Timeless Career Advice for Engineers

Henry Suryawirawan: So you mentioned a few things about fighting people’s promotions and, you know, making sure they grow, right? So I think you also have a course, right? Timeless Career Advice for Engineers where you distill some of the core principles of engineering careers and maybe tips also for people to get promoted. Maybe if you can kind of like summarize what are the key learnings from there, so maybe for people who are interested, they can also take the course?

Louie Bacaj: Yeah, I mean, the course is just a very simple. It was sort of my first small bet as an entrepreneur. I said, you know, I was building all this SaaS and it wasn’t making any money. And we were struggling to sell the software that I was making. And I said, look, what if… I have all this knowledge. I mean, decade long career and I banged my head against the wall to learn some of this stuff. I might as well package it up and see what happens. And I did, and it did really well. And in fact, that’s how Gergely found me. And it’s led to so many opportunities for me, Henry.

But it’s an interesting thing because all I did was I said, look, if you were a pretty new engineer on my team and I really liked you and I wanted to see you succeed, what would I tell you? I’m assuming that people haven’t told you this stuff. Maybe you’re a mid level engineer, I don’t know, senior, something like that. Definitely, not principal or whatever because at that point, you probably know most of these things. Someone’s told you along in your career. So I said, what would I tell someone junior, mid level up to senior if I had about an hour and a half with them? And I just put it all down and I just basically spoke very candidly in that thing and just exactly what I would tell some of my own reports. In fact, what I told a lot of my own reports. And I would say there’s a couple of things there that I think are are interesting for the listeners in a very compressed fashion. I have a few rules of thumb.

I mean, number one is like engineers all the time sort of make this mistake that if their head’s down and they just do the work that they’re going to be rewarded. And it’s just not how it happens because, again, leaky abstractions and human beings on the other side. There’s political things, there’s the reality of the situation of finite resources to promote people. All these things are stacked against you and you might not realize it.

So a good chunk of the thing is just about the second part, to getting promoted, which is always about making noise. Engineers almost don’t like hearing this, because it’s kind of sounds like the squeaky wheel gets the grease. The one that’s the loudest gets promoted. But I think, fundamentally, thinking about it like that is wrong. Because if you are only the squeaky wheel and you’ve added no value, then at some point you’re going to get found out. You know, the Peter principle where you cap out, at some point you just can’t move up anymore. And so if you’re just making noise and you’ve added no value, people are smart. And when there’s a lot of resources at stake, like promotions and things like that, more money, more equity, whatever it is, they’re going to figure it out.

And so that’s not my recommendation at all. My recommendation is be heads down, add the value, do great work, but don’t forget to make the noise. And make the noise means, talk to your manager’s manager. Tell them what you did. It means tell the business what you did, you know. Like, fundamentally, people don’t bother saying that. One of the things that helped my engineers get promoted immensely in my organization is the thing I’m probably most proud of. It’s not just that I got promoted fast. It’s that a lot of people got promoted fast with me. And fundamentally, the difference was that they would tell the business, they would talk to the business and they would understand exactly all the metrics and things. And they would speak their language and say to the business, look, we move conversion from 1% to 2%. Or you know, these ads that we’re running, they’re much more efficient. We’re spending way less money. And so now the business goes and sends an email to me, to the CTO. Even if they don’t send it to me, you could ask them to send it. You could say later in the year, hey, my manager’s nominating me for a promotion. Can you write a small blurb about our interactions together? You know, just be honest. You don’t have to send it to me, send it to them. And I think, you know, when you have that relationship and when they know what you did, now suddenly you just stack in the deck, you know, in your favor.

This is the part about making noise. Now, if you haven’t done all those things, you can’t go and ask somebody to write you a small blurb about all the good things you did. So my recommendation is, add the value but also make the noise. Because if you skip that second part, it could be devastating, basically. You just worked your butt off for nothing. You got none of the rewards and that is devastating, I would say in a nutshell. You know, of course, there’s all kinds of things to factor in and to worry about, like do you actually, have you been enough? Cause you need to spend a little bit of time at role? Promotions are always about what else you can do for them. I think a lot of people mistake this. It’s not just about what you did. I mean, what you did is just sort of a way to try to convince them that you can do more. And a lot of people mistake that. They just assume I did this, this, and this, I should be promoted.

And one of the best ways to convince people that you can do more is to have the business come in and say, well, we have all this other stuff that we need. If we only had somebody that could build it, take it over, whatever. Now suddenly you know you have room for scope increase, which is really what promotions are about, right? But this all goes into that making noise part of it. And I think a lot of engineers… I sort of tweeted this recently, but this is a fundamental thing that I realized at some point is like, once you realize how many of the rewards in this world go to people that just make noise, you realize that you cannot afford to not make noise. It’s devastating to you if you don’t do that part. And so it’s very uncomfortable for engineers and you’re leaning into bragging, you’re leaning into keeping a brag doc and all kinds of stuff that feels uncomfortable. Sales, you’re selling yourself. You have to do that. Otherwise, you won’t progress as fast, unfortunately. It’s the reality of the world.

Henry Suryawirawan: Yeah, I like the making noise part, right? Because like what you said, right? Even though you made good work. It is sometimes, most of the times actually, it’s not enough, right? So somebody needs to know that you’re doing the good work. It’s not just your manager, right? He could just be the only person who knows about the good work, but that doesn’t work as well, right? So I think making noise, self promoting yourself and even building personal brand, right? It could be within the organization or it could be also externally, right? Or social media and things like that. So I think definitely that’s a very timeless advice.

[00:31:24] Going Into Entrepreneurship

Henry Suryawirawan: So let’s move to the second part of your career journey, right? So you mentioned you have worked all the way up, up to senior management, senior director. But you decided to actually quit all of that and become a self entrepreneur. So this is, I think, becoming also a trendy thing, right, especially after pandemic. Many people start to kind of like question about their career. And one optional path is actually to become self entrepreneur like yourself. So tell us maybe, like, how is the thought process back then and what made you decide so?

Louie Bacaj: I’m going to tell you a couple of regrets that I have, Henry, and they lead back into what we just talked about. Even though I was working my butt off at Jet and all these things, I still managed to put out a couple of side projects. And some of them actually did okay, you know. But I would say, fundamentally, those side projects helped me immensely. I mean, they helped me, number one, when I was a director, putting out a side project. Of course, I had to do it quietly. I couldn’t just, I didn’t want people in my organization thinking, this guy’s leaving for his side pro… I mean, you don’t want those things to impact you. But you could do it. You could launch something. You could find a way to bring some traffic to it, even anonymously, right? Like if the tool is good or whatever. But even though those things never paid off, I could never quit my job because of my side projects. In some way, that knowledge of gaining even 15 customers, using some brand new tech stack, some brand new technology, came back to me in the other stuff. Because when my engineers were talking about some new tech, I had already used it. I had already like customers in this other side using it.

Now my regret with all of this is that I didn’t take it as seriously as I should have. I was making really good money with the being a senior director of engineering and all these things, especially at Walmart after the acquisition. Tech has very competitive salaries and all of that. And I feel I wasn’t as rigorous as I could have been. I mean, of course, I had the insight, the passion for the side projects, the lessons from having customers, even doing customer support on a project was super helpful. But if I had been a little bit more rigorous in my selection criteria, if I had picked the right types of side projects, I could have had things that made money after I quit my job in 2021. So that’s my number one regret.

So the first tip for anyone listening is, the types of side projects you pick matter a lot. And so, and I guess the first tip is have side projects, because they’re going to help you even if it doesn’t take off, even if it doesn’t become a huge thing, it’s going to help you immensely, just because you’re learning something new. You’re gaining domain knowledge outside of the thing that you do at work. You know, you’re gaining domain knowledge with customers, with marketing, whatever it is. You’re gaining new communication skills. I mean, you have to promote the thing now. You have to bring some people to it. So I would say have some side projects.

And the number two, be rigorous about your selection criteria. Pick things that don’t cost a lot of money to keep running. It’s part of our small bets philosophy. A bunch of us have gotten together in this community and we’re all trying to do these things that make money. And so the way that you pick them matters a lot. And the amount of time that you invest matters a lot. And so, I maybe spent six months on one side project that had some AI elements in it. And then ultimately ended up failing, you know, that’s six months of nights and weekend. That’s pretty devastating. If I had picked better, if I had made some small tweaks to that, maybe that could still be around today and you never know. Over that time period, and now I’ve sort of grown a smaller audience, maybe now that thing could, you know, have a vastly different outcome than it did back then. And so this is my tip to people is basically have side projects and be rigorous in the things that you pick. Don’t just pick something willy nilly and all of that.

And so anyway, I say that because, hopefully, that’s helpful. But you know, in my own journey, I decided around the end of 2021 that I had saved up a little bit of money. I’d actually invested a little bit in some real estate here in the US. Not a lot, but just enough to kind of have some income. Even though, even if I was making nothing, I could at least have a roof. I have kids. Just have something from my family. So that was the big moment for me to say, you know what, if I don’t try this now, then I’m probably never going to try.

And so I really wanted to try. And I thought that I had the right skills. It’s just a matter of building the right things and all of that. And I sort of made my second mistake, which is the first mistake was probably not being rigorous about my side projects before I quit. And the second mistake is I took VC money. And when you take VC money, you’re almost creating a second job for yourself. And this is a very easy path for engineers. Because you’re technical, you can build things. These are things VCs love. And then it’s very easy to lock you up for four years eating ramen, making nothing, and then maybe the thing doesn’t pay off. And so, you know, I would say, you should be rigorous. I’m not saying don’t take VC money. I’m just saying that when you take VC money before you have anything, before you have money, the power dynamic is very skewed. They have all the power. You just took their money and you have a moral and legal and ethical obligation to try to deliver on their income.

So anyway, my brother and I quit at the same time. We took VC money and our VCs were great. There’s nothing against them. The thing is still going, in fact, and we have equity in it and all of that. But we decided after about a year or so that look, this VC world is not for me. Because, actually, as a software engineer, I can make money tomorrow. I mean, not as an employee, right? Like I can make money tomorrow. I could consult. I could put out a video course, which ended up making me, you know, 60 grand almost in that first year, that one small video course. I could do so many things to make money that are almost impossible when you are 100% all in, which is what the VCs want once they give you the money on this one thing. And you’re getting like a measly ramen salary, because you have no customers. You have none of that.

And so I would say, a few months into that journey, I sort of had this realization that, you know, I was getting anxiety. Like if it’s entrepreneurial journey, I have a family, even though I had some money from real estate. I might have to beg my old boss for a job again. I might be crawling back and say, please take me back, you know? To me that felt devastating. Like I felt like a quitter, you know, in my dreams. And so I said, no, screw this. I’m going to find a way to keep my dream alive. And so I went back to the folks at the VC back thing. And I said, look, I’m going to have to wind down. You know, I’ll help you, hand things off. I don’t want to just leave you guys high and dry. I made the commitment to help you. So I’ll help you with that. But ultimately this isn’t for me. I’m basically quitting. I’m resigning right now, but I’ll continue to consult and I’ll help you in all of that.

And so I decided that, look, I’m going to just place a bunch of small bets, see if I can get some of those to money, and then see what happens. And that’s exactly what I did. I basically put this course out. That was my first thing. I built two other SaaS products that year. Very small SaaS products. And another, I built a live course. I wrote a book. All these things are within the wheelhouse of the software engineer. But most of them, they almost don’t seem that sexy. But when your options are quit, give up on your dream and go back to full time employment or try these things, you might end up trying them. So this goes back to the whole idea of be rigorous about your side project, because you could do some of these things that I’m talking about, like small bets, even without quitting your job. Just learning these skills that you need to build an audience, to communicate, to sell, all these things that are very, very important.

Anyway, so my journey is, it was very windy. But I feel I’m in a pretty good place right now in terms of making money and all these surviving basically. I’m not rich or anything, Henry, but I’m surviving, I don’t have to go back and beg for a job, which is important, I think, to have a chance to have something take off, you know.

Henry Suryawirawan: Hearing what you just mentioned, I think one thing, if I can get it right. So you seem to value independence and maybe kind of freedom more. Was that the reason, the main reason why you decided to quit full time job? Because so many people dream about this, right? But it’s just the motivation to take the step and take the risk, which is probably a lot of anxiety.

[00:38:59] Sense of Freedom & Independence

Henry Suryawirawan: I mean, I also consider that sometimes, right? But of course, there are many factors, not just quitting the job and just pursue your dream, build some things, and it’s going to be successful, right? So tell us maybe what was the key reasons why you actually took the plunge and decided to quit the full time job?

Louie Bacaj: I mean, independence is a huge thing, right? Like when I was a senior director at Walmart, even tweeting something is not trivial, right? Like you could get.. And look, it’s not like they were bad to me or this is just normal big company stuff, right? Like if you tweet the wrong thing, you could get fired, right? And this is a very real thing that I think a lot of software engineers sort of contend with, which is why a lot of them go anonymous or whatever, right? But it’s just very difficult to build real relationships and all of that anonymously.

And so anyway, I think I had a colleague who was maybe a director at the time. He asked to be able to present on a topic that he had been working on at a conference. And they denied him, legal denied him. And part of the reason they denied him at the time was because that stuff was kind of sensitive and they said, no, no, no, we don’t want that out there.

And so, imagine that now you can’t go to a conference and you can’t speak because legal said no. And I mean, they own you, right? Like that’s what they’re telling you. Like by having that thing over you, they can fire you and take away your livelihood which is, you know, it can be pretty devastating. I mean, at the time I was planning on quitting anyway. So I was less concerned, I would say, about getting fired. But I just didn’t want to go out like that, Henry. Like I didn’t want to go out in a way where HR fires me. I wanted to go out with dignity, you know, like I wanted to go out like Michael Jordan, like hang the, hang the jersey up.

So part of it was just, I would say a sort of ethical and moral obligation to not go out there and bad mouth or say something bad while I’m working for these people. Again, it’s not that I was saying anything bad, it’s just very easy to misconstrue something or even say something that is a secret, let’s say, and then you get called by HR and then you let your team down. All these people that were depending on you to promote them or whatever, now they’re very upset because you just got fired, you know. You don’t want that to happen.

And I would say the more senior you become in an organization, the more of a problem this is. The more they own you, the bigger the gag order, the more stuff they make you sign. And this is the challenge, right? And so, I was at that place where I had the side projects, none of them were working, and I was convinced a big part of the reason they weren’t working is because I couldn’t just lean behind them and say, hey, this is my project, this is what I’m doing, buy it, for me. And if there’s something wrong, I’ll be the one to give you your money back. I’ll be the one to support you with it or whatever. You can’t do that. And so that I would say made me value freedom on a sort of different level.

And then, even in the VC world being all in means basically that you are just working on this one project, but that’s super risky, right? Because that one project simply may not work like everyone… And of course, you know, people say, oh, pivot and do this and that. It was not that easy to pivot when you’re in with partners and when you’ve told these people what you’re going to do. You have some sort of obligation to keep trying at that thing and the pivots are usually not pivots in a way that you’re not going to suddenly be like start doing courses or you’re not going to suddenly start doing like something radically different that has nothing to do with it, with the thing that you took their money for, because that’s not what they gave you money for.

And so you’ve committed to be all in, and that is even more of a gag order than like the big company thing. Because at least in the big company, you know, you don’t necessarily need to put in 12 hour days. But they control what you say afterwards and they don’t necessarily control it. They don’t necessarily control it up front. They sort of control it by the threat of firing you and taking away your livelihood and maybe embarrassing you because you got fired for saying something dumb. But anyway, so I would say that freedom is a huge, huge thing.

Look, I’m making maybe about, at this point, this is two years now into this journey, I’m making probably about a little over 200K a year now on my own, right? Between the small bets project I’m partners in with this guy, Daniel Vasallo and, you know, whatever little small bets that I have out there. It took a while. The first year I made about a hundred grand. And I remember tweeting how happy I was that I made a hundred grand on my own. But you keep in mind, I was making maybe, I was approaching a million dollars all in. I mean, you know, not in cash, but in equity, in all these things at Walmart as a senior director.

And so people are telling me, you know, they’re laughing at me. They’re saying, oh, you’re happy making a hundred grand. Like you used to make a million bucks. This is sad, you know? And so, yeah, it’s true. It’s sad. But I get to say what I want. I get to work with who I want. I get to work on what I want, when I want. I get to walk my kids to school. I don’t have to report to some office. I don’t have to show up to some other country, because we’ve got another team over there. And you can build this up, right? Like it doesn’t have to be a hundred grand forever. I mean, you’re working, so you’re going to do things. And so I would say to most people that the freedom is worth it, you know. Do it for the freedom when you need to survive, right? Like you want the freedom, but you need to make some money, because you need to eat. And so if you can somehow get the freedom and eat, then the sky’s the limit, because you’re going to do your best work. You’re going to find a way to carve some kind of path for yourself, I think.

And you know, you’re way more capable, especially in today’s world, right? Like think about where tech is right now, how valuable tech is, in general, how powerful the AI tools are, how much they can help you build, how fast you can build things. You’re like a modern day Michelangelo. You can sculpt your way to whatever you want, because you have these skills. And people, some people, they would give up their left arm for some of those skills that you sort of have. And so a lot of software engineers don’t value that stuff properly if they were on their own and trying things. They’d be shocked at what ways they’d find to make money while still retaining their freedom. I think I came to this realization with a windy road and after making some mistakes, of course. But you know, I think this is par for the course, you know, Henry

Henry Suryawirawan: Very inspirational. So thanks for sharing that story, right? So I think that’s really, really key, right? The freedom. Especially with the current situation where there are many layoffs happening and it’s sometimes not even your fault. You’re just maybe at the wrong end of the books or something like that, right? And you just got laid off. And if you don’t have these kinds of side projects or maybe other things that you can also bet on, I think it’s probably very devastating, right, to your career and to your personal identity, right? Because the job is probably all you have. So I think, yeah, what you’re saying is true. It’s becoming even more relevant for us these days.

[00:45:10] Small Bets

Henry Suryawirawan: And I think you have mentioned a couple of times about small bets. Some people may relate that with just like a simple thing, simple experiment that you do. But actually you do have a community called Small Bets to encourage people to actually do these kind of side projects and try to earn a thousand dollars, right? That’s kind of like a goal. So tell us a bit more about this project or this community.

Louie Bacaj: Yeah, so absolutely. So, you know this started as a course by this guy, Daniel Vassallo, who was an ex Amazon software engineer. He had a successful career himself. He took this same sort of plunge and path before me, you know? And I think this is one of the beautiful things about the world right now is one of the other sort of gifts is that we can learn from other people, right? Like they’ve done a lot of the thing that we want to do. And so Daniel had quit his cushy high paying job, tried entrepreneurship, banged his head against the wall, made mistakes, figured things out. And he put a little course together called ‘A Portfolio of Small Bets’. And it was about how he was making money online. And so that’s how it started. And then it evolved. And he put some principles together, rules of thumb. Basically things that he thinks anyone that wants to escape the nine to five, find a way to fend for themselves ought to do in order to succeed, right. And he learned that stuff the hard way. So that was basically the course.

And it turns out there’s a lot of people right now, especially as soon as the pandemic hit and all these other things that want to figure these exact things out. And so it grew, I mean, it went from a small course with 45 people in each kind of cohort live. He was doing the Zooms for three weeks and then that was it, basically. And then eventually it evolved into a Discord community. Now we’ve built our own tools. I was a community member. And then one day Daniel said, look, I think this thing has more legs. Maybe we could do more with it. We could build tools to help some of these people succeed. We could add other classes. We could have other people teach. We could turn it more into a platform.

That sounds very ambitious, but every single one of these things happen like a small bet itself. Like we said, okay, well, the first thing we need is we need some kind of website. Right now, everything is on this website called Gumroad and we don’t even have a landing page and we don’t have any way to register for events or any of that stuff. So first, we built a website. You know, that was pretty quick. And then later on, we started integrating more things into the community. We built a member directory, their projects. We added on the ability to have people come and teach our community, people that have figured out certain things. So if you want to learn YouTube, you get somebody who’s an expert, who’s done the thing, who’s grown an audience on YouTube. In fact, we have maybe more than one person teach you, because everyone has different experiences and is on talking about different topics. But so we had things that we were interested in learning ourselves in this world of fending for ourselves. We brought in people to teach us and it turns out that there’s a whole bunch of other people that are actually very interested in that same kind of thing and it sort of been evolving from there, you know.

And so it’s a project that makes money. Of course, we pay the people that come and teach and all these other things. But it’s a project that makes money and it pays me and Daniel something. Plus we are, we both have our own small bets. I’ve got my engineering course, as you mentioned, I did a thing on newsletters, teaching people how to start and succeed with newsletters. Daniel has a thing on how to do Twitter well. He has a book on AWS, in fact. So all these things, you know, everyone has different small bets that are placing, but we’re also part of this community learning from each other what works and all of that. And I’d say it’s good for people that are interested in side projects.

It’s good to help you a little bit to inject the rigor that I was talking about before because, you know, if you don’t have that, you could waste a lot of time, basically. You could make a lot of mistakes. And it’s a shame to burn, because probably the best way to do this, if I could go back, the best way to do this is with a bunch of my side projects and small bets would still be alive today. Even if they were only making a little bit of money, if I had rethought them slightly, if I had built them in a cheaper way, if I had factored these other things in, I would have increased my odds that one of these could have accidentally grown. When my audience grew or when someone talked about it randomly, whatever it is.

And basically that’s what the community is about, is to help people build up these skills needed in this world, now fending for yourself. Whether it’s audience building, getting some attention or with side projects. And it’s just for us to continue learning and continue going on this journey, basically.

[00:49:12] Learning from Small Wins

Henry Suryawirawan: Yeah. So I think one of the key thing that you advocate in the course as well is to actually ask people to build small projects, side projects, right? And many people still assume that if they want to become self entrepreneur, they need to build a startup. Like a startup that can go big and something like that. But actually one of the things that you advocate in the course is like, forget about building company. Let’s try to earn like a thousand dollars, learn from small wins instead of big failures. So if we can probably advise people, like why is this a key thing for us to consider about?

Louie Bacaj: Yeah. I mean you could very easily waste a lot of time company building, creating the LLC, doing all these things. And people will convince you that that stuff’s really important. And you know, it is important, like at some point it’s important. But not when you have no customers, I mean, having dark mode before you have zero customers is just not that useful. So these are little things that I think engineers can easily make these mistakes, because it feels like you’re working. It feels like you’re checking things off a list. It feels like you’re making progress, but it’s sort of fake progress. I mean, the only real progress is someone giving you money for something you made. And unfortunately, it’s one of those tough pills to swallow. And so that’s why we advocate for that.

But another thing that you mentioned, which is this idea of small wins. I mean, you learn so much more when something hits than from something just absolutely bombing out. And the reason why I say that is because many of my side projects, in fact, bombed out. They made no money, they got no customers. I had this side project called DealBit, which is basically the idea was that you could earn Bitcoin or Ethereum, sort of like Rakuten, but you earn Bitcoin or Ethereum and you integrate it with these APIs. And at the time I was working at Jet and I thought, look, this would be cool. Crypto is a cool new thing. And in fact, it taught me a lot about affiliate APIs, which then, you know, I was able to use in my career and actually helped me in Jet.

But the project, the point is the project really got no paying customers. And so what did I learn from that? The lesson that I learned at the time was that crypto sucks. And the reason why it sucks is because the fees are too high and they were high. I mean, it was like, it costs a lot of money to transfer something from an Ethereum wallet to another. So basically, if you earn $5 shopping on Steam or PlayStation or whatever, and the fee is $5 to give you that Ethereum, what did I give you? I gave you nothing. And so this was like, I was like, you know, this thing just doesn’t work, basically. This was sort of the takeaway that after some time, the fees were eating too much of it and people weren’t making enough. And so the whole thing sucks, I thought.

But there’s actually a company that made it work. You know, years later, they made it work. Why? I mean, things changed, the fees changed. Now imagine, if I had found a way to keep that project alive, instead of shutting it down, instead of all of that, if I had architecturally built it in such a way that, you know it could just be out there, right? Like maybe, you know, randomly it turns into some sort of small win or whatever. And so the point is that you almost learn nothing from failure. My lesson from that was not the right lesson, because someone else made that work.

And so you can extract all sorts of things from failures that are actually wrong. It’s not really why it failed. You just were unlucky. You were just at a bad time. You know, the same exact thing done six months later for no reason works. It’s a complicated system we live in this world. And there’s all sorts of edge cases and leaky abstractions and things going on that you just, there’s no way for you to account for that. But I mean, you can increase your odds. There are things you can do to sort of increase your odds.

And so the whole point is that basically to find ways to get some small wins. Because once you actually get a small win, even if you get 10 paying customers, now you have lots of lessons. Now those learnings, you can rely on them. You can ask this person, why did you buy it? What else do you need? You have so many ways to take it. Once you actually have a small win, there’s actually something in the Bible that I think Daniel Vassallo likes to quote, which is the Matthew effect and where the rich get richer, basically. It’s like if you have resources, you just start winning more. Well, it makes sense if you have customers, you know, you’re probably going to get more customers cause they’re going to tell other people about it. Now you have a thing that works.

And so this is why we push people to try to get something to money because that’s where everything is. That’s the road to heaven, you know, that’s the road to basically all the lessons, all the learnings. Once you’re interacting with other people, you’re building the right thing. You’re writing code that adds value. You’re building something that people want. However you want to put it, basically. And so we’re huge advocates of that.

And I think people make this mistake. They think they they naively believe that if I just keep, you know, digging into this thing, this thing is going to change the world in six months. And then. Six months comes and nothing happened and they wasted six months. That’s devastating again, right? Like now you just, you thought you were adding value, but you added value to no one and you wrote a bunch of code and it’s useless. And so I think you could still, you know, maybe get some small lessons from that. But imagine if you had real customers, you know. The lessons are just so much better. And this is the key to some of these principles that we push in the community.

Henry Suryawirawan: Thanks for such an inspirational message again, right? So I think for people who are interested in building something, side project, right? Start on self entrepreneurship. Don’t start doing something that is too big, get a small wins, right? First, of course, like find the passion, what you are trying to work on, right? So I think that’s very important. Be rigorous, like what you mentioned in the beginning. And also try to get the small wins instead of big failures. I think that’s a very key message to me.

[00:54:24] The Importance of Writing Skills

Henry Suryawirawan: So something that I also saw you with all these small bets, right? You actually started your journey by also building kind of an audience through writing. You are kind of like big on Twitter. So tell us about this journey, right? What did you learn, and why did you do that?

Louie Bacaj: So this is a great question. I think writing is just an incredibly powerful thing. Even in the age of ChatGPT, right, which is one of those things that, you know, of course, ChatGPT can spit out, LLMs and you know, they can spit out all kinds of text. But as an individual, sitting down and being able to communicate your ideas and putting them into the world, and concisely, right, because people are pressed for time. I mean, they don’t have time to read this massive story, you know, all of that. So you’re saving them time. I mean, the way I like to think about it is like, if I’m writing a tweet or a post or a newsletter or even when I was starting with this stuff and I still had a job, if I’m writing to my team, every extra word has to be multiplied by another human being on the other side. So if 10 people are reading it, that’s 10 people that have to spend a few seconds because I couldn’t concisely express myself. That’s pretty harsh, right? Like so there’s immense leverage to being able to communicate well, to being able to get your points across. And it’s in fact, how you get ahead very, very well if you get good at this skill, even in the age of ChatGPT.

But also I would argue that when you sit down and you sort of have to write these things down, you start thinking. You know, like you thought in your head something made a lot of sense. But then you start writing it down, and then you realize, wait, I missed this edge case or this actually doesn’t make sense anymore now, once you factor in this edge case. And that’s very good, because you’d rather know that it doesn’t make sense than think that it’s a good idea. Keep it in your head, let it bounce around, and maybe potentially down the road, put down code, build something, and it’s totally the wrong idea. It’s basically never going to work, because you just didn’t think through all the edge cases with it. And so being able to sit down and put your thoughts down, I think it’s just incredibly valuable.

So one of the things that I got from that was, that I recognized that immediately even before I quit my job is, wow, I mean, this stuff works. Even like when I was doing the annual reviews, I was injecting some of the playfulness from my writing that I was getting in my social media and other places. I was injecting it into people’s annual reviews. And then I have one guy come up to me and say, this is the best annual review I’ve ever read in my life. I mean, this is just. And so, stuff is powerful, man. It’s really, really powerful. And it’s just, it goes a long way. And so it’s worth investing into, even if in my view, you have no aspirations for entrepreneurship.

But then if you do actually have aspirations for entrepreneurship, then having a small little corner of the internet for yourself, I mean, that’s really powerful too. Now you have, if you build an app, you have some people that you can have look at it. You have some human beings, some attention that you could bring to it, which costs a lot of money in this world. Not only does it cost a lot of money, but I used to work at, you know, I ran all the ad tech at Jet. You know, I built all those systems. It doesn’t work. The ad tech doesn’t work anymore. People are basically sick of ads. The ads just don’t have the effectiveness. So you, even if you have money, even if you have capital, it doesn’t mean you could bring people to the thing. But the thing that works is relationships. You know, people liking you for something that you’ve, they’ll give you the time of day. They’ll try your app. They’ll give you feedback on it because you did something else for them. You helped them in some other way. This is powerful stuff. And you can’t get that unless you put yourself out there a little bit, unless you put what you know, unless you give it away, unless people have access to it.

And so anyway, I’ve managed to carve a smallish audience. There’s nothing big, but it is, you know, for me, I’m very, very happy because I definitely consider myself an awkward and introverted engineer that had to push himself quite a bit to learn some of these things. But they’re worth learning and they’re worth like the discomfort you have in the beginning doing these things. They pay dividends over a long enough career, they’re gonna compound, this knowledge, this asset knowledge of how these things work. It compounds significantly. And so I think, you know, I don’t know the rate of compounding, but it’s there. And I think it’s pretty high in today’s world.

So, yeah, my advice to people that are thinking about that kind of stuff would be to do it. Find other people that want to do it as well. If you have to, even if you’re in an organization, I mean, you know, write a blog post for your organization. Like start a blog for your company. Ask other engineers in the company and say, hey, who else wants to write a blog about what they’re working on? This kind of stuff is very valuable. It’ll help your company, but it’ll help you and it’ll help your career and it’ll help you even when you leave the company. And so, yeah. Do these things, basically no matter where you are, is my point. It just turns out that this stuff is valuable in a career, in entrepreneurship. It’s just valuable everywhere today.

Henry Suryawirawan: Yeah. I find that writing is a kind of like underrated skills, right? It is applicable in so many things, even though if you want to do YouTube videos or maybe TikTok and things like that, you still need to write kind of like a script, right? You need to write the key ideas and also distill the information that you want to convey. So I think writing definitely is a worth skill to invest for everyone. So thanks for sharing your story.

[00:59:18] 3 Tech Lead Wisdom

Henry Suryawirawan: So Louie, I think we’ve heard so many things, so many good things out of your story. Unfortunately, we have to wrap up. But I have one last question that I would like to ask you. This is kind of like a tradition in my show, which is to ask my guests to share the three technical leadership wisdom. So if you can think of it, it’s like an advice that you want to give to all of us. So what would that be?

Louie Bacaj: Yeah. I mean, you know, we touched on a lot of it throughout this call already, but I would say the big one is the people that you hang around, they’re going to influence you immensely. If you’re in an organization where the people aren’t that good, you need to leave. There’s no other way to put it. Show me your friends, I’ll show you your future. It’s a proverb for a reason, but I say, you know, show me your colleagues and I’ll show you your career, basically. And it’s true no matter which way you phrase it, no matter which way you do that one. So I would say a huge one is work with great people, find them, seek them out. And in today’s world, you could go follow them on Twitter. You could interact with them. There’s so many ways to get access outside of just an organization to get access to great people. So I say that one, that one’s a big one.

I would say, you know, my number one rule of thumb for people is add value, but don’t forget to make noise. I mean, if you’re just adding value and your head’s down then you’re not going to get the rewards, unfortunately. The world is a cruel place when it comes to that.

And then I guess the third one is we touched on be rigorous. We touched on have side projects. We touched on all of these things. And I guess the third one is a combination of those things. It’s just do things that have good odds of success and make that investment. If the odds are good, it’s going to pay off for you. So have side projects, be rigorous about them and do them with eyes wide open. And even, again, if you choose to invest 12 hours a day solely into the company you work in, be rigorous about that, right? Like run the numbers in your head. Do some small calculations. What are the odds that this thing’s going to succeed? How’s it going week over week? Don’t just be blind about these kinds of things. So be rigorous in your activities, I guess, is sort of the third leadership principle. So the people was the first one. The second one is be rigorous. And add value, make noise. Thank you, Henry.

Henry Suryawirawan: Yeah. Yeah. So thank you so much, Louie. So for people who like this conversation, they want to learn more from you. They want to follow you online. Is there a place where they can reach out?

Louie Bacaj: Yeah, I would say the best place is on Twitter @LBacaj. Actually this is the easiest way to follow me on Twitter is just to go to smallbets.com and both my Twitter and Daniel’s Twitter is right on, like literally on the landing page at the very top. So you could just click. And I say follow both of us. We’re both on this journey, sharing lessons from going from engineering into entrepreneurship and that whole thing. Yeah, so I think that’s probably the best place. Twitter and Small Bets. I’m always in there.

Henry Suryawirawan: If you haven’t followed Louie, I think I would suggest following him on Twitter, because he sometimes posts quite insightful tweets, right, for you sometimes to reflect and some things that you can learn as well to apply in your career and in your journey, right? So thank you so much for those tweets. So Louie, thank you for your time today. I hope people learn a lot from your story and your lessons.

Louie Bacaj: Thank you very much, Henry, for having me on. This was a great conversation.

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