Aakash Gupta and the essay that became a career

The essay had taken a weekend. The audience took a second try. In March 2021, Aakash Gupta published an argument about Roblox on his personal website and watched almost nobody arrive. He was working at Epic Games in Cary, North Carolina, and the idea had grown out of the kind of conversation that used to happen in an internal channel about the games business. Gupta thought Roblox might become something like a shopfront for game makers. A few people may have found the page. He has recalled roughly 30 visitors. Then he put the essay on LinkedIn.

People answered. Old colleagues reappeared. A former debate partner sent a note saying the piece had opened his eyes. Gupta had published the same idea in two places, but only one of them had people standing around it. The lesson was plain enough for a product manager: distribution was part of the product.

Five years later, Product Growth is his full-time work. He reports more than 236,000 subscribers to the newsletter, a second AI publication with more than 231,000, and a podcast with over 150 episodes. He has also built a live program for people trying to land product roles. Those figures are his own published counts. The more interesting number might still be the first one: about 30 visits to a piece he believed was worth writing.

The conversation that left the office

Gupta’s path to writing began inside product and growth teams. He has described starting in software engineering before becoming a product manager at a startup in 2008. His later work took him through thredUP, Epic Games, Affirm and Apollo.io. By 2020, he was at Epic in Cary, with a half-hour commute each way. When office work moved home, one small part of working life lost its usual setting: the casual exchange of interesting links and half-formed theories.

He had enjoyed contributing to an internal games-industry news channel. By the spring of 2021, the conversation there had slowed. The Roblox thought seemed too good to leave in Slack, so he researched it over a weekend and wrote it for a wider audience. It was his first public test of something product people do routinely at work: notice a pattern, make an argument and see who disagrees.

The LinkedIn response changed his routine. He wrote about games, technology and product management, then stayed in the comments to talk to readers. In his account, he had barely posted on LinkedIn before the Roblox piece. The replies offered something traffic numbers could not: proof that somebody had taken an idea home and turned it around.

“Your article on Roblox opened my eyes!”A message from a former debate partner that Gupta says he remembers.

There was an accidental teacher in the next act. After weeks of watching videos about writing, YouTube served him a David Perell video. Gupta followed the trail to Perell’s writing course, Write of Passage, paid $4,000 and entered with more than 15,000 LinkedIn followers. The course sharpened an idea already visible in his posts: his particular experience lay where technology, products and growth met. During that period he launched the Product Growth newsletter on Substack.

A newsletter with a day job

At Affirm, Gupta led product growth while the newsletter grew on nights and weekends. He has written about work spanning the mobile experience, customer messages, financing and an affiliate business. He reports that Affirm’s annual revenue rose from about $300 million to $1.2 billion during his tenure. That is a company-wide change, not a result to assign to any one person. His role nevertheless gave his writing a useful constraint: the person explaining growth was still living with product decisions.

The writing had no single clever formula. It took long research, a clear angle and a schedule that had to survive a demanding job. He found that short posts could travel while the deeper essays built a library. During a family trip through Europe in 2022, he wrote brief posts on his phone over espresso while his son napped. In his telling, he did not open a laptop during those two months. The image is pleasingly ordinary: an ambitious publishing plan reduced to a phone, a coffee and a small window of quiet.

When work at Affirm became more consuming, his publishing slowed. The company laid off nearly a fifth of its staff in February 2023, and Gupta has said he was among those affected. He restarted the newsletter and social posting that day. A product career had supplied his material; now the work of explaining product decisions was becoming an occupation in its own right.

He later became VP of Product at Apollo.io. In late 2023 he left that job to focus on Product Growth. He said publicly that the creator business was already earning more than the VP role. Money alone does not explain the decision, but it removed one obvious objection. He traded a senior title and a company’s roadmap for a publication whose next issue would always be due.

The writer has to run the business, too

Product Growth became a publishing operation. In 2024, Gupta counted 88 deep dives and about 462,000 words. That is more a record of sustained work than a claim of literary merit. It meant choosing subjects, interviewing people, editing, sending, measuring the response and coming back again. His product background supplied the vocabulary for that cycle, but it did not make a blank page less blank.

The audience did not rise in one clean line. In a fifth-anniversary post, Gupta described several moments when he thought the newsletter’s growth had stalled: a move from Epic to Affirm, reduced posting during his work at Affirm, the decision to leave Apollo, falling LinkedIn engagement and changes to Substack recommendations. His account is a publisher’s version of a familiar product problem. A channel works until it changes. Then the product has to deserve attention somewhere else.

His publications have also narrowed and widened at once. Product Growth still deals with product strategy and career moves, but AI now occupies much of his attention. He started AI by Aakash as a separate newsletter covering what is happening in AI. On The Growth Podcast, he talks with practitioners including Wix co-founder Nadav Abrahami, product discovery teacher Teresa Torres and people building AI products at large technology companies. The interviews give the written advice another texture: someone else must explain what happened when a promising framework met an actual team.

The podcast has passed 150 episodes by his count. A recent episode asked Zapier CEO Wade Foster about the company’s rubric for AI fluency. That is a characteristic Gupta question. What do companies say they value, and what do they ask people to demonstrate? The answer interests an operator, a writer and a candidate preparing for an interview for different reasons.

“I love talking about tech, products, and growth.”Aakash Gupta, describing the focus he chose for Product Growth.

From advice to practice

Gupta’s career material has moved closer to the job search itself. He publishes free interview cheat sheets and runs Land a PM Job, a live cohort with lectures, coaching, AI-tool practice and interview preparation. His site says the first two cohorts sold out. This is a different promise from a newsletter. A reader can take or leave an essay; a student expects a useful change in how they work or present their experience.

His current advice to aspiring AI product managers emphasizes visible work. He recently described a sequence that ends each skill with something a candidate can show: a prototype, a documented agent workflow, a set of evaluations. The tone is practical because the hiring question is practical. Can a person describe an AI feature, spot its failure and decide what should ship?

That focus also completes a circle. In 2021, Gupta had to learn that an unpublished argument had no audience and that a published one still needed a place to meet readers. He now asks product candidates to make their work inspectable. The settings are different, but the action is similar: turn private effort into evidence someone else can examine.

A useful kind of repetition

There is a risk in retelling any creator story as a neat ascent. This one was interrupted by job changes, slow periods and distribution shifts. It also benefited from a career in companies whose names opened doors and gave Gupta real product questions to write about. Both parts matter. The first essay worked on LinkedIn partly because a network was already there to receive it. The newsletter lasted because he kept giving that network new work to judge.

Today his professional identity is less a single job title than a set of recurring appointments. A newsletter issue arrives. A guest sits down for an interview. A cohort meets to prepare for interviews of its own. Gupta can move among those formats because the central question remains close to the one that sent him down a Roblox rabbit hole: how does a product find its people, and what happens after it does?

The answer changes with the product, the platform and the year. The habit is simpler. Notice something worth explaining. Do the research. Put it where other people can answer back. Then, if they do, write the next one.