Quitting his venture-backed startup to make $300k/yr from small
bets
Louie Bacaj quit his lucrative job and built a venture-backed startup. Then, he quit that too and started placing "small bets". Now, he's making $300k+ per year across his portfolio.
Here's Louie on how he did it. 👇
Quitting a lucrative career
I had a long career as a software engineer, climbing the corporate ladder to lead other engineers.Â
I was one of the youngest senior directors in Walmart Global Tech. But I felt like I’d reached the top of that traditional path.
Many of the VPs and Executive VPs, who were the next level up, had been doing the same thing over and over for decades to get there. They sat in lots of pointless meetings, traveled wherever the company sent them, left their families waiting around for them, and dealt with loads of bureaucracy. They were paid well for it, but the ones I talked to didn’t seem all that happy.
To me, that would have been hard to swallow. And the money, while it was incredible, just felt like a ball and chain to keep me there — and a muzzle to shut me up.
So I decided to quit my traditional career and become an entrepreneur. I had already diversified all the money I'd made in tech into real estate and rental properties, so that gave me courage — I had income from offline businesses.
Taking a "small bets" approach
After quitting my job, I spent a few months trying to do a venture-backed thing. We raised around $1.5 million.
But a few months into that venture, it became pretty clear to me that it wasn't going to work. We had no customers, and we were grinding on the same thing over and over. But we had taken money from people we knew. I felt a moral and ethical obligation to keep trying to get them a return. It was a terrible feeling and gave me a huge amount of anxiety.
After a little over a year of banging my head against the wall to make that venture-backed thing work, I ended up resigning and did my best to wind that down in an amicable way by helping the folks who wanted to keep going find my replacement.
After winding my activity in the VC-backed thing down, I found my way toward placing smaller bets.
I saw other people making a living in interesting ways. Some did courses, some did books, some did small SaaS apps. It was fascinating to me.
At that same time, I started having some minor success on Twitter and had a few viral posts around career advice for software engineers, so I ended up recording a short course in about 4 days. That made over $50k the first year. That same year, I wrote a short book, built tools, and all sorts of other things with varying degrees of success. All in all, I ended up making about $100k, all with a bunch of seemingly unrelated things.
People took notice and helped in various ways. Some amplified the products they got value from. Some invited me to partner in various projects. And in 2023, I cleared $200k from all of these activities.
Then, in 2024, well over $300k. None of this is including consulting or real estate.
Online businesses got harder and easier
On one hand, as COVID and lockdowns wound down, I think doing business online got a little harder. It was certainly not impossible, but harder than when there was a huge number of people locked up in their homes and their only outlet was the internet.
But on the other hand, some things seemed to get easier. Building has never been easier than right now. You can get AI to write a large chunk of the code, and you become tech lead for your own stuff, forcing AI to provide more quality outputs.
So, in 2025, I have gone deep into this path of building things with AI. These days I largely use Claude to code.
Thanks to AI, I have been able to make some great progress into more seemingly unrelated things like game development. I built a few free games (1, 2) and a few SaaS apps like Lightweight Analytics.
The advantages of a boring tech stack
In the age of AI, it is really important to have a go-to tech stack.Â
One of the advantages of AI is that it can write a lot of code really fast. But if it does that in a stack you are not familiar with, it will be really hard to understand, modify, extend, and so on.Â
Sticking with things you know well — boring tech — is an advantage because you can easily see where the AI went wrong.
That is why my go-to stack for web apps is boring old Asp.Net with Razor pages, and SQLite for the DB. I was using Azure and Serverless functions, Cosmos DB, and all kinds of stuff trying to get fancy early in my journey, and it was a huge mistake, costing a lot more money than a simple web app running on a VPS somewhere.
Get off Azure. Get off AWS, it's a waste of money for 99% of the people reading this.
Obviously, when I am building a native iOS app, like I did with WalkWrite, an app that uses local models to transcribe audio notes, I can’t use my go-to stack, so I am forced to learn something new. But even then, I do my research and make sure to pick some sort of stack that I can keep reusing.
Leverage time boxes
I’ve found the hackathon style of building something within a time-boxed window to be really advantageous, especially now in the age of AI.
The risk many indie builders have is to delude themselves that, “One more feature will make it so everyone wants this thing.” This was the trap my partners and I were locked into with the venture-backed thing. But a lot of times, it's way better to take a week or two, do a hackathon for yourself, and build a brand new, totally unrelated product. Especially if you feel motivated and inspired about it.
And honestly, this style of working is a good style even if you are adding features to an existing project. If you don't time-box it, you'll burn a lot of resources.
Have a plan for getting your first users
A lot of my early customers for each of my various products came from Twitter.
But I think social media has changed. Twitter has certainly changed. How to get customers has changed. And I've changed too.
But even with all that change, there are a few things I've learned that aren't going anywhere.
First of all, it’s been really helpful for me to have a general idea of where I think my first few users will come from.
I’ll formulate a sort of thesis of how many users I might be able to get from a certain channel. Maybe I’ll tweet about the thing a few times. Maybe I’ll write about it in my newsletter. Maybe I'll run some free workshops. Maybe I’ll make some YouTube videos about it. Or maybe it's more of an SEO play and I need to optimize those pages.Â
But before I build the thing, I will think through and test the channel for the initial set of users. And I'll figure out what sort of growth loop might work.
Of course, all of this is guesswork, but it is worth doing. Building without any idea of where you might get your first few users is a recipe for burning a lot of time.
Word of mouth
Overall, I'd say most of my growth comes from word of mouth. If a product is good, people will tell other people about it.
No amount of hammering people you don't know will change their minds and make them buy. But word of mouth can bring a lot of strangers in and give them a reason to trust you.
And sometimes that word of mouth can be engineered by building growth loops. It's an amazing thing when it works.
A case for one-time payments
I have experimented with more than a few online business types, from info products to software to communities. And I have experimented with many types of online payment models. I would say one-off purchases where someone pays you and you deliver the thing and the transaction is complete is my favorite.
As a software engineer switching to entrepreneurship, I had been conditioned to love SaaS and recurring revenue. But that comes with support requests, servers, product uptime, and other things to worry about.
Building things and talk to people
Like I said, this is the best time ever to be building things. So build things!
You'll learn a lot by taking action. By putting things in front of people.Â
My other piece of advice is something that I often need to remind myself of too: Talk to a lot of people. Don’t just build in isolation.
It's really easy to be a hermit when you are a software engineer. But to make money with things, you need to solve other people's problems. And it's really hard to do that without talking to people.
So force yourself if you have to. Talking to people is never a waste of time.
What's next?
Earlier this year, I had my third baby and have been enjoying the time freedom that being an entrepreneur has given me. I just build while the baby naps. This is the first kid I was around for all the time. With the other two, I worked at a startup and had to go back to work fairly quickly.
I also realized that it's kind of lonely to build by yourself, at home all the time. So, I recently decided to get involved with the guys who started and run a community called Write of Passage. They are starting something new called Act Two and I will be a minority partner, teaching mostly beginner vibe coders how to build their apps. I've picked up some tricks in the last few months about how to get better outputs from these AIs, so I'll be sharing those. And beyond lessons, Act Two is about taking action, accountability, and community. If you are interested in this, the 5-week live program starts this week.
So, for the immediate future, my goal is to run a great program and help people that way, all while hopefully building some tools for the Act Two community.
Long term, my only goal is to avoid having to beg my old boss back at Walmart for a job back. So far, so good.
Follow along
To learn more about me, you can sign up for my newsletter. I send occasional updates and things I am learning the hard way. You can also find me on Twitter, but I am less active on there these days. And my thoughts are a little more raw there.
Leave a Comment
Love the small-bets + time-boxing playbook. For one-time products, which channel got your first 10 customers fastest—X threads, newsletter, or YouTube?
That sounds too abstract. I would enjoy reading how exactly you did your 100-300K and how to repeat it on our side
nice post. it could be improved by providing a list of the top 5 revenue-producing things that Louie built. the article is kind of vague and could be improved with more specificity about what Louie built, how long it took to build and produce income, and a reflection from him about building that product.
also, the Act Two link 404s
as a follow up article, it would be really helpful to know how exactly Louie tests an idea with potential users. show us the actual reddit post or tweets he has used to pitch an idea to potential users and get signal that the idea is worth building. would be very useful to us here trying to figure that out.
hey Alex, its a great point of feedback, I will ping James (who interviewed me) to get the 404 for act two fixed, this is the link to that: https://www.act-two.academy/
But to make things a little better and more concrete, this was one of my first products to make some real money in my first year:
https://lbacaj.gumroad.com/l/career-advice-for-engineers
Then I followed it up that same year with these two:
https://lbacaj.gumroad.com/l/newsletterlaunchpad
https://lbacaj.gumroad.com/l/beginnerrealestate
In parallel I also became 50% owner of https://smallbets.com/
There of course many other projects, and tools, like TapeX, and ThreadX that only worked out to a few grand in revenue, and a few other tools that did not work out. And of course there are many others I have built this year, some they linked to above.
I find this the most interesting part and they never mentioned one of his products
hey Rahim, they mentioned at least a few above, like act-two, lightweight analytics, the two games, but I tried hard to not make it too promotional and not link out to a lot of different things.
But if you are interested in some of the things I built early on in my journey, these are the products that brought in most of that first $100k in my first year:
https://lbacaj.gumroad.com/l/career-advice-for-engineers
https://lbacaj.gumroad.com/l/newsletterlaunchpad
https://lbacaj.gumroad.com/l/beginnerrealestate
But there are others that made less.
Great story Louie,
As someone in a similar space trying to come up with "small bets" I've been stuck in the loop of finding an idea and dissecting it to the point that the idea no longer seems viable to me. What advice would you give to someone struggling to come up with meaningful ideas to pursue?
This is tricky because I too can, and have gotten in my own head about things too. So I totally relate.
My opinion is if you really inspired to work on an idea, especially to make money with it, you should just make sure you can fit into some time frame: two weeks, a month etc. And you should run at it before the motivation & inspiration goes away. I have gotten a lot more done by making the ideas smaller. You can always add more to ideas that work.
If it's a sort of passion project or something you enjoy, and its not about making money, then you can approach it with a different lens I think. But ideas for money, after a tiny bit if research, its better to just build it quickly and learn from that I think.
But I totally understand how you can get stuck over analyzing, or see someone else doing it and say screw this etc. It's happend to me, but if its small enough then there is hopefully no time for that to happen, you have the thing and trying it out.
There are other ways of course, but this has been my approach the last few years and it's worked.
Hey Louie, really inspiring journey! 🙌
I love the “small bets” approach and the time-boxed builds seems like such an effective way to test ideas quickly without burning out. Your point about sticking to a “boring” tech stack also resonated, especially now with AI generating code fast using what you know saves so much time fixing things.
Curious: when you have multiple small ideas at once, how do you decide which one to focus on first?
Tania, which idea to focus on is a great question. I dont have an easy answer.
But I think I have gotten to a point now where I keep a backlog and work through them in these time boxed chunks. I built a few games and things this year that afterward turned out just ok. But I am glad they were small enough and I built them because I still learned. And most of all they are off my plate. It's really easy to get wrapped up and paralyed I think: which one to tackle first? which one will work best? those are all great questions and its very hard to predict what will work.
I think you have to get a point where you let the inspiration & motivation pull you, build the thing, but be emotionally disconnected from the outcome. That way even if it does not work out, you did not burn too much into it, and you can get on with the next idea and work on that too.
Some ideas might work out better than others and you can chose to invest more into them etc. This has been working for me.
The small bets approach is such a refreshing counter-narrative to the "go big or go home" startup culture. Your point about the psychological weight of VC funding really resonates - that moral obligation to investors can become paralyzing and push founders away from what customers actually want. I love how you've essentially created a portfolio approach to entrepreneurship, spreading risk across multiple smaller projects rather than betting everything on one big vision. The "boring tech stack" philosophy is brilliant too - using familiar tools means you can focus on solving problems rather than fighting infrastructure. Your experience with one-time payments vs SaaS is particularly interesting for indies considering their business models. It's inspiring to see someone build sustainable income ($300k+) without the typical unicorn playbook. Thanks for being so candid about both the struggles and the successes!
Really appreciate how candid this is. A lot of people glamorize the “quit your job and build SaaS” path, but your story shows both sides — the stress of going the VC-backed route and the relief of focusing on smaller, more flexible bets. I like the way you framed the boring tech stack too; it’s refreshing to hear that simple and maintainable usually wins.
The “time-box” approach especially resonated with me. It’s so easy to get stuck in endless feature creep, but shipping something quickly and moving on feels way more sustainable. Thanks for sharing all of this — it’s motivating to see someone build a solid life and income without chasing the stereotypical “big startup” dream.
Love how grounded this is. The “boring stack + AI” point really resonated — I ship faster when the base is familiar enough to spot AI’s mistakes.
I’m curious about your “one-time payments” approach: how do you know early if a product fits that model instead of SaaS?
Thanks for sharing your path, especially the balance between small bets and family.
Respect for building a $300k+ portfolio on your own terms...
hey louie, really appreciate you sharing the full journey — it’s a reminder that there’s no single path to sustainable income from tech. the small-bets approach makes a lot of sense, especially today when AI lowers the barrier to ship usable products fast. i’ve noticed similar patterns among indie saas founders: one-off revenue from niche products often outperforms recurring models early on, provided you validate demand and focus on high-leverage features. your point on time-boxed builds is spot-on — it’s the closest we get to testing market-fit without burning months of dev time. would love to hear how you prioritize which small bets get your attention first.
I have a different answer for you for existing projects vs new projects, Suno.
In terms of new projects, I sort of chase what I am most motivated to work on and what I think might have the best odds.
For example, I am going to launch a game on the app stores and charge a few dollars, this is after building a few for free and launching those to sort of learn the ropes. I am doing this because I actually really enjoy building these but also I am fairly confident I have it down now where I won't spend six months on it. And can get something out in about a month.
In terms of existing projects and adding to them, I like to go by whats working best. So if a tool has very few users so far I wont invest too much into it, ill leave it out there, maybe that might change as SEO picks up or something else happens. But if something is working and its clear I can get a return on my time if I add more, then I will for sure add more. It's much easier to know with stuff thats working and when there is data and build on it from there, this has been my experience.
But I definitely do not neglect new ideas, or oppertunities, especially ones I am really inspired to try. I just make sure I can fit them into some form that wont burn a lot of my time and resources.
I am not sure if thats the best way to do it, but so far I have enjoyed doing it that way and its worked out fairly well.
really appreciate you sharing such a detailed and transparent journey. Your “small bets” approach, time-boxed hacking, and focus on simple tech really resonate with what I see working well for indie SaaS founders today.
Your mix of diversified projects, early user channel testing, and leveraging AI like Claude for coding is impressive—and clearly effective. One thought I had that might add extra structure is formalizing how you score and prioritize new bets based on learning potential, ROI, and niche interest before full builds, coupled with micro-launches for hyper-targeted validation. Using AI not just for code but for rapid prototyping, landing pages, and early feedback might tighten those loops further.
not sure if you’ve experimented with any of that kind of structured prioritization or rapid AI-powered validation?
That’s a bold move—sometimes smaller, focused bets bring more freedom, stability, and long-term upside than chasing big, high-burn venture.
Louie, this hit deep. Walking away from prestige and pressure to build on your own terms—that’s founder clarity. I’m building White Waters Sentinel, a civic tech platform for pipeline security in Nigeria. Bootstrapped, live, and driven by urgency. W2S2 was born from watching communities face oil theft, pipeline vandalism, and silence. Nigeria lost over 37 million barrels to theft in 2021 alone—crippling revenue and trust. W2S2 is my way of turning frustration into infrastructure. Your story reminds me that small bets aren’t small when they’re rooted in purpose.
I agree, that's exactly it
This resonated. Thanks for sharing!
"asp . net with Razor pages" is just the best!!
Most people try to scale one project vertically but there are many people like yourself that decide to scale horizontally. Why go through the stress and anxiety as you mentioned trying to make one thing work to the moon when you can have multiple smaller apps/saas products working well. Nice job!
The power of focus and flexibility can be seen in quitting a venture-backed startup to pursue small bets. Choosing sustainable income over scaling risk illustrates how building the largest company isn't always the key to personal success.
By focusing on independence, sustainability, and creating value without interference from investors, James Fleischmann was able to earn $300k annually by quitting his venture-backed startup.
Loved this arc ; trading the VC treadmill for small, time-boxed bets and a calm profit target. The “boring stack” choice (simple hosting, lean DB, minimal dependencies) plus a first-users thesis is such a clean way to cut risk. Also really resonate with choosing one-time payments when it fits the value moment instead of defaulting to SaaS.
Curious: across your bets, what single constraint improved your hit-rate the most (tight scopes, strict deadlines, or audience-first distribution)? And which channel ended up durable vs. just spiky; SEO, community, or direct email?
P.S. I’m with Buzz, we ship conversion-focused Webflow sites and pragmatic SEO for product launches. Happy to share a quick 10-point GTM checklist if useful.
Absolutely loved this journey — it’s inspiring to see someone navigate the shift from corporate to indie with such clarity and honesty. The “small stakes” mentality and focus on time-boxed building really hits home. Thanks for sharing so openly!
Thats really inspiring
As a result of leaving his venture-backed startup, James Fleischmann earned $300k annually by making small, smart bets - showing the power of independence, focus, and strategic decision-making.
LGTM
Hey Louie, thanks for sharing your story. It's inspiring. Re: lightweight analytics, which channels do you use to acquire traffic?
The switch from VC grind to small bets with tight time boxes felt like sane, repeatable progress. The “boring stack” take, having a first-users thesis before building, and leaning on engineered word-of-mouth all ring true. The case for one-time payments over default-to-SaaS is a refreshing reminder to optimize for calm profit, not overhead.
Curious: across your portfolio, what single activation best predicts revenue; first successful ship inside a 1–2 week box, first organic referral, or first paid one-off? And if you had to over-index for the next 60 days, would you pick more hackathon-style sprints, deeper content/SEO, or doubling down on one compounding product?
P.S. I’m with Buzz, we build conversion-focused Webflow sites and pragmatic SEO for product launches. Happy to share a short GTM checklist if useful.
🚀 From Corporate Ladder to “Small Bets” Success
1. Leaving a High-Paying Career
Louie Bacaj rose quickly in tech, becoming one of the youngest senior directors at Walmart Global Tech.
Despite the prestige and pay, he saw the next rung of leadership as repetitive, bureaucratic, and unfulfilling.
He had already invested his tech earnings into real estate and rentals, giving him financial breathing room to take risks.
Decided to leave corporate life to pursue entrepreneurship.
2. The Venture-Backed Detour
Raised $1.5M for a startup after quitting his job.
Struggled to gain customers; felt moral pressure to deliver returns to investors.
After a year of stress and little traction, stepped away and helped transition leadership.
3. Shifting to “Small Bets”
Inspired by others making a living from small, independent projects (courses, books, SaaS tools).
Gained a following on Twitter with viral posts about software engineering careers.
Created a short course in 4 days → earned $50k in the first year.
Wrote a short book, built tools, and experimented with multiple small projects.
First year of “small bets” brought in around $100k from a mix of unrelated income streams.
đź’ˇ Key Lessons So Far
Diversify early: His real estate investments gave him the freedom to experiment.
Small bets reduce risk: Multiple smaller projects can add up to significant income.
Leverage audience: His Twitter following became a launchpad for products.
Speed matters: Quick execution (like the 4-day course) can validate ideas fast.
yes i am agreed