Winning with Communities & Creators

An Interview with Sasha Kaletsky

It’s fair to say that a lot of the people who post regularly on X (formerly known as Twitter) are much better at tweeting than they are at operating or advising a business in the real world.

One exception to this rule is Sasha Kaletsky, Co-Founder of Creator Ventures (backers of Beehiiv, FaceIt, Bounce and many others) and my latest guest on The Raffi Report.

I had been excited to talk to Sasha for some time — he’s a newsletter writer himself over at Consume Our Internet. With regard to digital consumer economies, he’s one of the most thoughtful folks that regularly publishes online. In a bit of a twist from past editions, rather than publishing a transcript of our conversation, below you can find the full video interview.

We cover everything regarding online influence, tooling for Creators, retail media and emergent ad networks.

Before you dive in and (hopefully!) enjoy, I wanted to provide the main takeaway I had after reviewing this chat a few times.

Put simply, Sasha is an independent thinker. In a world where people increasingly lump their own beliefs in with whoever shouts the loudest, there’s a smaller well of original thinking.

To take but one example, all throughout the hype-phase of the Creator Economy in 2019, right up until today, Sasha has maintained his position that these customers offer “the unholy trinity” of “the sales cycle of an enterprise customer, the churn of a consumer and the purchasing power of a SMB”.

Now this viewpoint has been proven true, but there was indeed a time where the broad consensus across startup-land would have you believe that YouTubers paying £5.99 a year for a video editing tool could yield multiple venture scale exits.

Let’s be clear: there are countless world-class founders building in the Creator space still, but let’s also admit that many folks were high on their own supply.

Anyway, the point is not to bash anyone or anything, it’s to emphasise that whether you’re working in a big multinational business or a ten person company, you can and arguably should go against the grain.

Whether your goal is achieving cultural relevance, growing your MQL pipeline or educating your customer base — the best marketers sit back and form their own opinion, rather than trying to copy and paste a playbook they found online.

Perhaps the best introduction to this conversation, in the end, comes from Jeff Bezos: “What I’m really asking you to do is to embrace and be realistic about how much energy it takes to maintain that distinctiveness. The world wants you to be typical—in a thousand ways, it pulls at you. Don’t let it happen.”