🔴 3 moves to bet your next 10 years on

The most valuable information exchanges are moving from public platforms to private communities. It's a shift that's reshaping how creators build sustainable businesses.

Jordan DiPietro has spent two decades in media, climbing from financial analyst at The Motley Fool to Chief Growth Officer, then later becoming CEO of Hampton, the exclusive high-priced community for tech founders. Along the way, he’s witnessed the rise and fall of trends that dominated the creator landscape: the short-form content gold rush, the podcast explosion, and the paid newsletter boom.

Recently, he left his CEO role to work as an advisor and write his own business newsletter, Signal // Noise.

In this episode:

— Natalia Pérez-González, Assistant Editor

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By Natalia Pérez-González

Jordan DiPietro's crash course in sustainable media began as a young financial analyst at The Motley Fool, where he spent 12 years learning that successful content businesses optimize for customer lifetime value (LTV), not attention metrics.

By the time he joined, in 2009, the company had long since weathered the dot-com crash — shedding most of its staff before reinventing itself with a subscription model that set the stage for long-term stability.

This inspired Jordan’s first rule for long-term creator success: build direct relationships with your audience, not dependency on platforms or intermediaries.

"If you came up through The Motley Fool, you understand database marketing and segmentation better than most people," he told us. While other publishers treated editorial and marketing as separate functions, The Motley Fool framed them as different points in the same buyer journey.

At The Hustle, he worked alongside Sam Parr and the team that would inspire a new generation of business newsletters, sharpening his instincts on audience development in an era where growth meant creativity, not just ad spend. Then, as CEO of Hampton, the high-ticket founder community Parr founded after The Hustle, Jordan helped scale a business model that measured value by trust between members.

These experiences revealed something that would reshape his view of the creator economy: the most valuable information exchanges weren't happening in public anymore; sustainable creator businesses require deep expertise in your domain plus sophisticated audience development systems.

"Some of the most successful tech founders are finding solutions to their problems in their communities first, not in Google or ChatGPT," Jordan remembers realizing during Hampton’s board meetings. Members were sharing proprietary AWS configurations, revealing complex system setups, and discussing acquisition strategies they'd never post publicly. This level of trust bred a comfort and transparency nearly impossible to find on open platforms.

Based on everything he's seen over the last two decades, Jordan distilled three bets he believes those in the broader content industry should seriously consider over the next decade.

At The Motley Fool, “audience” meant millions of readers. At Hampton, it meant a curated circle of executives who shared sensitive information they’d never post online. The difference between the two was reciprocity; creators who architect two-way value exchanges — who seed rituals and then decentralize control — will outlast those chasing impressions.

In the early days of YouTube and Instagram, the formula was “grow big, figure out revenue later.” That doesn’t work anymore. Jordan argues the sequence is still build first — but what you build must be trust, anchored to a downstream strategy. At The Hustle, growth was always tied to a monetization ladder, even if the cash came later. At Hampton, members paid not just for content but for confidence that the people around them were vetted, aligned, and credible.

After two decades, Jordan sees three edges creators can lean into: attention (distribution), taste (curation), or trust (relationship depth). He’s played all three. At The Motley Fool, it was attention through SEO syndication. At The Hustle, taste in identifying what stories resonated. At Hampton, and now in his newsletter, Signal // Noise, it’s trust — the kind where readers email him for advice on business decisions, or tell him they’d join him in any venture, even if he started a carpet company tomorrow. “That’s optionality,” he says. “And it comes from trust.” (Read more on this below under Steal this Tactic).

A few things that stuck with me as I listened through this week’s conversation:

Connect with Jordan on LinkedIn.
Subscribe to Signal // Noise here.

Jordan’s three-arbitrage framework provides a diagnostic tool for understanding which type of value you're uniquely positioned to create, and which battles to avoid.

To determine your strategy, you need to ask yourself: What do people actually value about your work?

Attention players should focus on platform optimization and conversion systems. Taste players should develop deeper expertise and more sophisticated curation systems. Trust players should prioritize transparency, consistency, and relationship building over growth metrics.

This is what most people think the creator economy is about, but Jordan argues it's becoming the least sustainable path. Attention arbitrage means you're competing purely on your ability to capture eyeballs across platforms — follower counts, view metrics, viral moments.

"If that's your game, if that's what you're great at, awesome. Then play that game and do that all day long," Jordan told us. But recognize the economics: you're competing in the most crowded space with the fastest commoditization timeline. Platform revenue sharing remains minimal, and converting viral attention into sustainable income requires additional business infrastructure that most creators haven't built.

The trap: confusing vanity metrics for business metrics. Having millions of views means nothing if you can't convert that attention into revenue streams that outlast algorithm changes.

Taste arbitrage means your audience trusts your filtering mechanism more than your original creation ability. You excel at synthesizing complex information, identifying trends before they hit mainstream, or presenting familiar concepts through compelling new frameworks.

This path requires deeper expertise but creates more defensible differentiation. Jordan points to the explosion of newsletter operators who've built six-figure businesses not by creating original research, but by curating and contextualizing information better than anyone else in their niche.

The key insight: in an information-overloaded world, good filters become more valuable than good generators. Your audience pays for your ability to sift through noise and surface what actually matters.

Trust arbitrage takes the longest to build but creates the most business flexibility. Jordan mentioned people telling him they'd join a theoretical carpet business he might launch, despite his complete lack of industry expertise. "I don't know anything about carpets, but it tells me people trust me,” he says.

Outside of personal charisma, trust is built through consistent reliability, transparent communication, and demonstrated competence over time. Trust allows creators to pivot between verticals, launch new products, and weather platform changes because the relationship transcends any specific content category.

Trust arbitrage creates optionality — the freedom to pursue multiple revenue streams because your audience follows you, not your content format.