Turning a neglected, 17-year-old side project into a $26k/mo business

Buster Benson had big ambitions that had nothing to do with turning his back-burner project, 750 Words, into the 920k-user, $26k/mo product that it is today.

It was a side hustle, and an oft-neglected one at that. But after 17 years of slow growth, he quit his job and doubled down with the intention of growing it to $50k/mo within a year.

Here's Buster on the winding path that led here. 👇

The path of a curious monkey

I’ve spent 25+ years weaving through tech, writing, startups, burnout, and art, and am now focused full-time on growing 750 Words — my 17-year-old membership-supported private journaling platform used by thousands every day.

My work life started in 1998 after graduating with a bachelor’s degree in creative writing from the University of Washington. I was living just down the street from a hyped-up startup named Amazon.com and wondered to myself if I should leave my delightful job as a security guard at the Seattle Art Museum to jump into the frothy waters of the internet bubble to be a customer support rep on the night shift. That was certainly a turning point I could neither have predicted nor planned for, and maybe a bit like how college graduates today must feel.

My resume from that point forward resembles the path of a drunken, curious monkey, zig-zagging between big writing ambitions (a self-published novel in 2002, a viral article about cognitive biases in 2016, and a book about productive disagreements in 2019), running a real-world art and events space (McLeod Residence in 2006-2009), building small products and companies (43 Things, Health Month, Locavore, 750 Words), as well as participating in some exciting big companies (Amazon, Twitter, Slack, Patreon, and Medium), and making periodic swift emergency detours for burnout (2006, 2016, 2024), having children (2010, 2016), and global crises (2000, 2008, 2020) along the way.

I can trace a loose arc connecting these zigging and zagging dots with the theme of my interest in crafting words, technologies, and communities that try to make our lives feel more authentic and human.

Building $24k/mo community

750 Words is an online private journal that I launched in 2009. It creates space for you to brain-dump your thoughts and get some clarity in a world where we have almost no private space to think and reflect anymore. It encourages you to pour three pages of raw thoughts every day, and turns them into analytics, streaks, badges, and now things like AI prompts and reporting tools that reflect your own thoughts to you in often revealing and helpful ways.

It’s a humble lifestyle business, but it has managed to keep growing over the last 17 years because I think it taps into the deep need in our lives for a little time and space that we can call our own.

As of today, about 920,000 have signed up and over 13 billion words have been written. Over 5,000 people have written 100 days in a row or more, which inducts them into our prestigious Hall of Phoenixes, where they are invited to share a bit more about themselves. Even people who enjoy the deeply solitary act of private journaling enjoy a little community.

There are 470 people who have streaks over 1,000 days in a row, 197 with streaks over 2,000 days in a row, and 68 with streaks over 3,000 days in a row.

The site started as a free site, became a donations-supported site in 2010 when the server costs became significant, then shifted to a membership site in 2014, and continues today with 2 tiers of membership — $5/month for standard or $10/month to be fancy and get some additional features and support. The 200,000+ people who joined before becoming a membership site in 2014 were all granted a Lifetime free account, and we have happily honored that.

As of this moment, we have about 5,800 paying members and make about $26K/month in revenue. Revenue had been pretty flat from about 2019 to 2024 at around $20K, so this is the first time I've really tried to grow the site's revenue in its entire history.

My current goal is to grow it to $50K/month in the next year.

Getting started

As I said, I launched 750 Words in 2009... but didn’t “become a business” until 2016. It was a sole proprietorship until then.

It was built during a phase of my life when I was building a lot of things. Registering domains every week. Building little websites and apps for all kinds of whims. Starting companies and raising money. The ideas I was excited about all circled around behavior change and habit building in various ways. Most of these ideas and websites died of neglect — either I lost interest, or the idea couldn’t be realized in the way i imagined, or nobody else liked it.

Truthfully, 750 was no different from the rest in terms of being neglected by me. I had a newborn in 2010 and had closed down my previous startup, Habit Labs, to take a full-time job at Twitter, relocating to the Bay Area, and for many years, barely gave 750 enough attention to keep the servers up. Once, the domain even expired for a full day before realizing what had happened.

It lived in maintenance and support mode from about 2011-2020. However, to my surprise, 750 wasn’t like the rest in terms of being neglected by its users. Unlike all the other things I had built up to that point, this one continued to grow every month for years — even after moving from free to donation-supported to membership-based. And it generated enough income to pay for the servers and to also provide a nice part-time salary to my partner and wife-at-the-time, Kellianne, who answered all the support tickets and apologized for all the bugs I never had time to fix.

That forced me to take the project’s value seriously even when I couldn’t dedicate time to it. 750 turned into a business when we realized that there was enough interest in things to keep working on it — and because living in the Bay Area was expensive and this was beginning to contribute a meaningful amount to our costs of living.

I never would have guessed that a private journaling website would be the stickiest and most loved product I’ve ever built, but I’m grateful that it is! It’s a product that I not only love using myself, but that I also love building. I re-wrote the whole app in 2020 during the pandemic, and finally found a way to work on it full-time as of last October. The timing feels right to give this my full attention, but the timing is built on 16 years of luck, the patience of our users, and duct tape.

Building the product

I built the first version of the site using Ruby on Rails and jQuery on a shared server in about a week. I hired a designer to help me craft some of the badges. I added features here and there for the first couple of months when I could, but eventually, my attention shifted.

The biggest effort during those years was responding as promptly as possible to all the people who had lost passwords or that had broken a streak for either personal or bug-related reasons. Because it's about writing every day, and the day ends at midnight, there was often a big surge of people writing at the end of the day that would cause the site to crash and then streaks to be broken. The site has a strange architecture because most of the database queries are writing to tables instead of reading. In 2009, we were one of the only places doing the auto-save thing, and I wrote it all in jQuery in a way that probably wasn't optimized very well.

In 2020, I re-wrote the whole site and split it into a Rails API backend and a Vue frontend. Up until that time, I was working mostly as a product manager at various places and hadn’t been writing much code at all, and so was delighted to see how much these frameworks had improved over the previous 10 years.

In the last couple of months, I’ve re-written the entire frontend (upgrading Vue 2 to Vue 3), with the help of Claude Code. The leap in improvement enabled with AI is even more striking and fascinating to participate in, and the code of the site has never been in a better spot.

Metrics and models

My business model is to offer a monthly and yearly subscription for $5 that clearly delivers more value than it costs. About a year ago, I added a $10/month tier that includes new AI-prompt features (to offset the added cost of using LLMs). I've recently updated my user funnel and analyzed everything from visitors visiting the site to creating an account to starting a membership trial to paying for the first time, and then retention month to month from there.

Here are some raw numbers to give a picture:

• About 30-40k people visit the site every month (most new visitors are from search, but AI is also starting to be a significant referrer).

• On a slow month, we'll get 1,500 signups, and on a great month, we'll get 3,500 signups, so let's say 2,500 on average, or 7% of visitors sign up organically. It's around 9% from ads.

• I currently give everyone a 30-day free trial before trying to convert people to members, and this is the weakest part of my funnel. Only about 1.5% of people who sign up end up becoming a member in that first 30 days... mostly because there's no reason to do that during a free trial. The hope is that if people use the product and like it, they'll be more likely to become members when the trial is over, but in reality, a lot of people will give up and never come back if they don't see the value of the site immediately. Journaling is something that takes real energy investment to see the value come out, and I've never really tried to figure out how to get people there faster or more efficiently — because all signs say that once you do see that value, you become a member and stick around.

• While only 1.3% of people become a member in the first 30 days, about 6% of people become a member in the first 90 days, which I feel is pretty healthy, and that number continues to climb a bit more slowly over the next couple of years, up to about 10%.

• Then there's retention, which is probably the strongest part of the funnel, further validating that once people see the value, they stick around. Subscriber churn rate is about 2.5% per month, and retention for the first year is about 80% (and goes up for subsequent years). According to Stripe, this puts us in the 75th percentile of small businesses. I think keeping these numbers high is what I'm most proud of, and I attribute it to keeping prices low enough that it feels like a no-brainer to keep paying, even if you're not using the site every day. I like to think that if people use the site a few times a month even, that the $5/month is easy enough to justify.

Getting the retention rate healthy is definitely the first requirement to growth. And that has been healthy for pretty much the lifetime of the site. Now, increasing visitors and signups could help, but I think there's probably an even bigger opportunity in thinking more about how to activate more of the remaining 90% of signups that never become members. I'll be working on a mix of both acquisition and activation this next year.

Product-led growth and reddit ads

I consider growth to be one of my best strengths and one of my greatest weaknesses. For whatever reason, I am not a natural marketer, and for the most part, this project has succeeded due to the fact that it didn't really require marketing to grow. Otherwise, there's no way it would have survived that 10+ year dry spell in attention.

As a product thinker, I do think a lot about how products grow, and I respect the ruthlessness that a marketing perspective and a growth perspective bring to the table in terms of making sure a product actually addresses a valuable niche in the real world. I love studying funnels and cohorts and calculating the cost to acquire a customer and lifetime value, and the very tangible, data-driven, game-like delight of identifying campaigns that demonstrably bring in more value than they cost to run.

But I dislike having to compete for attention with marketing and ads because the more you understand how they work, the more you realize that there are ways to maximize that funnel that feel slimy. These take you away from the reason you're building a product, because you start realizing that being misleading in small (and large) ways does actually work.

So, not "having" to market has been an incredibly fortunate and privileged permission slip that has allowed me to avoid what I see are inevitable consequences of doing the most effective — but not entirely honest or authentic — marketing.

With all that said, I am currently in a phase of trying to increase the growth rate of 750 Words through paid marketing, SEO, optimizing for inclusion in AI responses (what a strange new world we live in), incentivizing referrals from existing happy users, etc.

At the moment, the strategy that seems to be having the most success is Reddit ads. That works for me because I appreciate that Reddit's a place where bullshit is less effective. It's still early days, but signs are promising.

Staying indie

My guiding light for 750 Words has always been to build the product through the lens of love, delight, simplicity, clarity, etc. Pure intrinsic motivations that I feel are at the core of this practice of private stream-of-consciousness journaling.

It helps, of course, that this wasn't ever turned into a project that HAD to grow — which is what happened to several of my other projects that turned into businesses, raised money, hired people, etc. There's no greater enemy of intrinsic motivations than the panic of having to convince a venture capitalist that you can 10X users and revenue in the next year NO PROBLEM... and then actually having to do it because you took their money.

Remaining independent is not a guarantee of success, but in my book, it's a necessary-but-not-sufficient kind of thing. Else, sooner or later, the enshittification fairy will come sit on you and force you to cry uncle and pay tribute to some other higher authority than yourself.

Only one type of success is worth all the work

This may not be the most conventional advice you'll get out there, but it's still what I believe to be the most important thing to get right from the VERY BEGINNING — because it is almost impossible to get back once it's gone.

Get your values straight and build something that, if it does become successful, you will be proud of contributing to the world.

And work with people in a way that builds respect and sharpens your integrity, rather than dulls it. Life is long and the people you work with in your early days will be your best resources and relationships and support network down the line.

Yes, it does seem a little quaint and maybe even backward to value these things when there is so much that can be done more quickly now without them. However, I've seen so many people get everything they ever wanted success-wise but with nobody to share it with other than other mercenaries. The inner delight and pride of having built something that feels like a true and authentic contribution to the world, with peers that understand you and celebrate with you when you succeed, is the only success that feels worth the cost of all the work.

What's next?

In October, I wrote up a strategy to double 750 Words' revenue within the next 12 months — from $26k to $50k/month. I'm excited to see how that goes.

I had a similar goal last year, but only grew the site about 25%, from $21K to $25K. A big chunk of that time went to a full site refactor and migration from the previous site (much needed after a couple of years of neglect), and it was more about onboarding my skills and the site itself to this new world of AI-assisted development.

We're in a great spot now to build on that foundation. The world is changing a lot, and I had to decide between going back to a big startup that would be eating the goat of AI for the next couple of years, trying to reconfigure and reinvent itself in order to survive, or to do what I could to learn and build something that could support me and my kids in the Bay Area for the foreseeable future. I chose the latter and am having a blast.

The strategy I have currently has the following primary pillars (not necessarily in priority order):

1. Increase SEO and "Answer Engine Optimization" to get more traffic from LLMs. It's an interesting new landscape and something that is exciting to learn more about.

2. Paid marketing. Reddit is already performing pretty well, so fine-tuning that to be always on, then expanding to other ad platforms.

3. Launching more courses like the One Month Challenge, Creating Space, and Silly Robot that provide writing prompts (sometimes using AI and past writing to create smart prompts) that address specific life situations, circumstances, and use cases.

4. Continue keeping existing users happy enough to stick around. Here's a recent post where people had 5 coins to toss into a wishing well, which led to a list of enhancements like more badges, better export, better search, and more writing prompt courses as features that they most wanted to see built.

Follow along

I share a lot about my thinking of running 750 Words on this blog/forum. Outside of this project, most of my social time is now spent in a number of private Discord communities, which is a little bit sad since I miss out on the serendipity of connections that would be more likely to happen in a public social network.

The time I do spend in public spaces is generally LinkedIn, Threads, and Bluesky. I sometimes write things on Medium and Substack, and archive them on busterbenson.com. Also feel free to email me at buster at benson dot fm. I'm not the best at replying quickly, but I do try to be available to people who want to talk about things, ask questions, or share ideas.