The one thing I would temper, is that we don’t know for sure if there would have been better ways to monetize.

This is a fair point, and I do want to avoid the Armchair QB issue, where it's easy to make something The Team didn't do sound like it would have been successful, once matters are already decided and whatever was picked clearly failed.

That said, I think that over their lifespan, especially their time at peak, there must have been opportunities and options for monetizing that Reddit failed to fully exploit or embrace. I think that so many other people have made so much money off of Reddit over the years that Reddit Inc not getting their share feels like it must have involved missed opportunities.

At the very least, I don't think that the existence and community of Reddit is inherently impossible for Reddit to profit from.

I apologize in advance, this train of thought ran long and late; it's a really unique situation that touches on some stuff I think is super interesting.

Monetizing reddit required some very unconventional thinking compared to typical approaches at tech startups. Which kind of does loop back to how I closed above - I think that some of what has slowly gone wrong with Reddit over the past decade is rooted in tech startup culture itself, and that tech startup culture very highly values founders, tech people, software solutions, metric-able sales tactics ... and can massively undervalue soft/social skills and knowledge more aligned with Humanities' fields.

Starting off trying to go user-supported on somewhere between a donation basis and a soft-gamified award system is very tech startup - build a good software product users like to interact with, then ask the users to support the company, ~but make it fun~. That their next option was then to transition to ad sales using things like in-community placement to "target" is a fairly equivalent model of creativity - the users aren't donating enough, so lets serve a couple ads just to cover the gap.

Now, fully: I have biases here. I'm from a branding and communications background and my academics was 'community'. With that starting point, I don't think Reddit ever truly understood how significant and how impressive what they had built, from a community perspective, really was. Or how massive a commercial opportunity many of those communities represent if approached correctly.

As a very surface example, I think something like 90% of niche hobbies are fundamentally based around goods or services of some sort, and have companies competing to access the hobbyists as a targeted market. Reddit has hosted the dominant communities for many of those hobbies for a decade or more. Yet Reddit has never visibly attempted to leverage that.

Something I'm sure has been suggested and I strongly suspect has been rejected because it's complicated and has a long payoff scale would be selling abstract 'community membership' to companies buying ads. Not just placing the ads, but a much more comprehensive, but less strictly tangible, package of traditional ads, product placement, community management, and communications coaching. Redditors really like supporting "their own" and they tend to value even corporate entities that can engage on their level and participate in community membership; companies that can proverbially "take off the suit and shitpost" can Fellow Kids their way to financially valuable relationships with communities. Reddit being able to offer an advertiser a package similar to the level of support Victoria provided AMA celebrities during her time with the community - meets the successes that a company like Ghost Ship sees in their level of community engagement around Deep Rock Galactic.

It definitely is more complicated than just that and that model has other separate sales barriers, especially as a starting program. Equally, it cannot offer the concrete outcomes many large companies currently look for, while being a challenge to price accurately for smaller companies etc - I absolutely acknowledge that it would be hard. At the same time, I'm also wanting to note that this approach would be playing into an existing model for many companies' engagement with relevant consumer groups on Reddit already, and when done well the approach has a massively proven track record and clear payoff. Without necessarily following the exact model I'm speculating about above, but using it as an example of ways that Reddit could have been working to add value and and support to a space that already exists with proven (advertising) marketplace demand.

TLDR; at the very least, there absolutely were ways Reddit could have monetized its strengths rather than just its traffic.