For fifteen years, Aakash Gupta got paid to figure out why people buy things.
He had done it at Google, then at Affirm, then at Apollo, where the company more than tripled in valuation while he was running product.
By the time he decided to build something of his own, he’d done the work enough times to know what a winner looked like.
The app was called Rap to Beats. It would pull in 300,000 monthly active users at its height.
It would also fail to make money, and leave Aakash back at square one.
So in 2021, he decided to start a newsletter on Substack that took him back to his superpower — building and managing enterprise-level product.
Four years and 151,000 subscribers later, Aakash was bringing in over a million dollars a year.
It was what Aakash had layered underneath that had taken it to seven figures, and it was something almost no one in the creator economy had thought to build.
A Unicorn, an App, and the Lesson That Stuck
Aakash Gupta started his career as a software engineer, but it didn’t take him long to figure out that the part he cared about wasn’t writing the code. It was deciding what got built in the first place.
He moved into product management in 2008 and spent the next decade and a half climbing through some of the most demanding product teams in tech.
Google, Epic Games, thredUP, and Affirm, where he led growth product. And then eventually Apollo.io, where he became VP of Product, helping the company grow from a $750 million valuation to $2.5 billion.
The work was always the same underneath. Figure out what people would actually pay for, build it, measure it, cut what wasn’t working, and do it again.
Somewhere in the middle of that run, he turned his attention to building something of his own.
Rap to Beats was an iOS app that let users record themselves rapping over premier DJ beats, share their tracks, and climb a global leaderboard.
It worked. The app climbed to a Top 5 ranking in its category, scaled to 300,000 monthly active users, and held a 4.5-star average review.
What it didn’t do was make money.
The in-app purchases were live. The user base was huge. The reviews were strong.
But the revenue never came.
So in 2015, he decided to shut it down and went back to corporate product work, carrying a lesson that would shape everything he built afterward.
A product 300,000 people use is not the same as a product 300,000 people will pay for.
Engagement is not demand, and “traction” is not a business.
It would be another six years before he tried building something of his own again.
When he did, these same lessons would be the first thing he would reach for.
Crickets, a Forwarded Post, and the Number He Wouldn’t Stop Tracking
In March 2021, six years after Rap to Beats, Aakash hit publish on his first Substack post.
The newsletter was called Product Growth, and it was about exactly what he’d spent fifteen years doing — building, growing, and managing products for some of the biggest tech companies in the world.
The first post was a deep-dive on Roblox, framing the platform as the Shopify of gaming.
The post sat on his personal site, and was read by almost no one.
In his words, “crickets”, doing nothing for the audience he was trying to build.
The lesson came fast. Publishing in a place nobody visits is not a writing problem. It’s a distribution problem.
He decided to start cross-posting everything to LinkedIn and X.
The same deep dives, broken down into shorter pieces, pushed into feeds where readers already were.
The newsletter began to grow, and by 2023, it was big enough to test whether he could charge for it.
He turned on a paid tier at $150 a year and ended up converting 0.2% of readers from free to paid.
Most newsletter writers have no idea what their conversion rate is, but Aakash published his, set a target of 1%, and started working toward it.
Then something happened that he didn’t see coming.
One of his deep dives got forwarded around inside Meta.
A wave of paid subscriptions arrived from people working at the company. Then another wave.
Aakash went back through his archive, looked at which pieces had triggered the same effect at other companies, and started writing more of them on purpose.
He noticed something else.
Buyers wanting to expense the subscription had to draft an email to their manager, so he wrote the email on their behalf and put it on his About page.
By 2025, the paid newsletter alone was bringing in $33,000 a month, sitting on top of a free list of over 100,000 readers.
The newsletter was the foundation. The rest of the business would build on top of it.
He launched a podcast covering the same ground in long-form interviews with senior product leaders, and turned the audience into sponsorship inventory.
Newsletter and podcast sponsorships together added another $30,000 a month.
He then built a 12-week cohort called Land a PM Job, co-taught with senior operators from Meta and other unicorns.
The first cohort sold out in three weeks.
On the side, he ran a small coaching line at $1,400 a month, deliberately capped, because the conversations gave him direct insight into what his readers were struggling with — material that fed straight back into the writing.
Each piece of the business served a very specific purpose.
Total revenue continued to build, and in 2025, crossed a million dollars a year.
A Newsletter, Run Like a SaaS Company
Most newsletters are run on instinct.
The writer publishes, watches the open rate, hopes the conversion comes, and adjusts based on a feeling about what’s working.
Aakash ran his differently, because for fifteen years, he’d been paid to measure growth at a surgical level, then adjust accordingly.
He had been trained to find the moments where users want to act and something gets in the way, then remove the thing in the way.
He would look at where revenue was actually coming from and double down on whatever was producing it.
He would cut the things that didn’t earn their place, even when those things felt important.
Run a SaaS product like that for fifteen years, and the instincts become permanent.
Look back at what Aakash actually did with the newsletter, and the moves stop looking like clever marketing decisions.
The Meta forward was a senior product person noticing a pattern, working out why it had happened, and rebuilding the content design around it.
The expense email on his About page was friction removal in its purest form.
A buyer wanted to act, something small was sitting in the way, and Aakash took the work off their plate.
The decision to keep coaching at $1,400 a month was a resource allocation call about where his time produced the most value across the whole business.
The answer was that an hour of coaching was worth more as an input to the writing than as a revenue line.
The published conversion rate, the public target, the disciplined tracking of what was working and what wasn’t — it was all measured and monitored.
It looks like how product managers run products.
That’s the discipline that turns a newsletter into a business.
Bringing the Same Lens to Your Own Work
There are four questions worth asking of your own business if you want to see the sort of success that Aakash has had.
The first is about willingness to charge for what you build.
Aakash learned this lesson the hard way at Rap to Beats.
300,000 people can use a product they love, and not one of them want to hand over a dollar for it.
If your writing is genuinely valuable (particularly in a commercial setting where it helps a reader make money or save money) then the question worth sitting with is whether you can charge for it.
There are plenty of writers on Substack who charge a fee for access, but there are probably a lot more who could or should be charging for their work and don’t.
The second is about measurement.
Once you do charge, the number that matters is the percentage of your free readers that convert to paid.
Aakash published his rate at 0.2% in 2023, set a target of 1%, and worked toward it.
A target gives you something to move against. Without one, you’re just hoping the number gets better.
The third is about removing friction.
Aakash spotted that buyers wanting to expense his subscription had to write an email to their manager themselves, and he removed that work for them.
Every business has equivalent moments.
Put yourself in your buyer’s shoes and walk through what they actually experience.
How do they find the product?
What questions do they have about it?
Are you answering those questions clearly?
How many clicks, fields, and decisions sit between wanting to buy and being able to buy?
That walk-through alone can change the trajectory of how your business performs.
The fourth is about what’s actually generating revenue.
Every part of your business is either making money or costing you something.
The free webinar that takes a week to prep, hours to maintain and update, and converts almost no one.
The lead magnet that built the list two years ago and now just sits there looking dated and does next to nothing.
Cutting what isn’t working and doubling down on what does is a discipline, but one worth pursuing without apology.
Aakash built a million-dollar business by treating his newsletter like a product. The same lens, applied honestly, will show you what yours could become.