For the longest time, I measured success by how many new people clicked signup every week. It felt like winning, even though my overall user count stayed completely flat because of churn. I finally paused all outbound efforts for a week and just emailed the people who had been sticking around for a while. Their feedback wasn't about needing flashy new features; they just pointed out basic friction points that made them want to pull their hair out. Fixing those three small things did more for my retention than months of acquisition campaigns ever did. When you hit a plateau, do you double down on marketing, or do you go talk to your existing users?

We offered a generous free forever plan for over a year hoping users would naturally upgrade as they grew. Most stayed on the free tier forever and treated us like a free utility.

Last month, we killed the freemium plan and switched to a strict 14-day free trial. Sign ups dropped slightly, but our paid conversion rate doubled almost immediately.

Did freemium work as a growth engine for you, or did it just cannibalize your revenue?

I watched a stranger use our product for the first time last week. Screen share, I just stayed quiet and watched.

It was painful

She skipped the welcome screen, missed the main button, and spent almost two minutes in settings looking for something that was right on the dashboard.

Everything we thought was obvious wasn't.

Spent years treating every email, DM, and support ticket like an absolute fire. turns out most of that urgency was totally self imposed.

Stepping back and letting messages sit for a few hours gives you long stretches of focus and half the time people solve their own issues anyway. The tricky part is when users or clients assume slower replies mean you care less about them.

How do you balance staying sane with keeping people happy when you stop responding instantly?

Most businesses and startups rely on VCs.

I would briefly write it as follows:

I wrote a long essay following a talk I gave at AI DevCon in Brooklyn last month.

It starts out with an anecdote about hunting ChatGPT in December 2022 and goes on to explore what I think will be necessary to thrive as code becomes a commodity:

In December 2022, I hunted ChatGPT on Product Hunt.

It ranked #1 product of the day, then the week, and went on to be named Product of the Year.

Having co-founded a YC-backed conversational AI startup in 2018 (long before LLMs) I recognized in ChatGPT the missing ingredient that would have made that venture viable.

The future we d anticipated had arrived. I could revisit my old problem, or I could expand my area of potency by raising and deploying my own venture capital fund.

I chose the latter.

Three years later, on December 9th, I watched a 24-hour window on Product Hunt cross 500 launches roughly double what I observed throughout the preceding 825 days. Only 13 were featured; most were unremarkable.

The LLM has fundamentally shifted the economics of software development.

As someone with a dual vantage point being the #1 Product Hunter while investing in AI startups I watch the floodwaters rise in real-time.

What s become clear: SaaS is dying; VC is withering . Building software is not uniquely compelling. Code has become a commodity.

What most people miss about commoditization is that when a product or resource becomes abundant, it doesn t just get cheaper. It unlocks new and previously uneconomic uses.

When users cancel right after their trial ends, it's easy to panic and think "We're charging too much." So the instinct is to offer discounts or lower the price barrier.

But whenever we dug into exit surveys, price wasn't even the top complainti t was usually that they didn't reach the "aha!" moment fast enough to justify any price tag. Lowering the price wouldn't have saved them if they weren't getting value.

For founders who went through early monetization: how do you diagnose whether churn stems from pricing structure or a failure to communicate core value quickly?

I have been thinking about this while working on integrations with third-party platforms.

Imagine a user connects their CRM, payment provider, or another external service. Everything works initially, but a few weeks later, an API token expires or the provider starts rate-limiting requests.

There's this weird pressure in tech where being available 24/7 is treated like the ultimate badge of honor. I tried stepping back from answering every random comment and non-urgent email right away, and honestly, half the people just went ahead and figured the solution out on their own. It made me realize how much time I was wasting babysitting threads that didn't need me. Have you ever tried going radio silent for a few hours, and did anything actually break when you did?