From the Diary of Riley Kaminer

Why the record of how an investment firm thinks becomes an asset over time, according to the founder of ClearCritical.

A lot of fund managers think about content episodically, says Riley Kaminer. “They decide they need to raise a fund, launch a strategy or get some press, and suddenly communications become important. Then the activity stops once the immediate need goes away.”

Riley describes what that leaves behind. He has worked with investment firms that were “doing genuinely interesting things for years but had almost no public record of it.” The thinking existed inside the firm, in conversations with LPs and in investment committee meetings. “When they wanted to grow, they effectively had to start from zero.”

He has made the same point in public. “LPs aren’t just backing brands per se, but backing managers that they’ve grown to trust over time,” he wrote in a LinkedIn post. He pointed to PitchBook’s finding that three firms, Andreessen Horowitz, Thrive Capital and Founders Fund, took in 48.1% of all capital raised in the first half of 2026, and drew his own conclusion: “The major asset these funds and managers have isn’t just capital; it’s reputation.”

Riley is the founder of ClearCritical, a content and communications firm that, as he puts it, “helps investment firms and founders turn their ideas, expertise and track records into a body of work that builds trust over time.”

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What ClearCritical Does

ClearCritical focuses primarily on investment firms and the companies around them. Riley says it helps VCs, private equity firms, family offices, asset managers and founders explain what they do and how they think. The work can mean investor letters, LP updates, thought leadership, newsletters, websites, case studies, media strategy, and LinkedIn or other communications.

Where the work starts is the part Riley stresses. “Most content providers treat the investment industry like another sector they can learn. We come at it from the other direction. We already spend our time around investors, founders and financial markets, so the starting point is understanding the substance. The writing comes after that.”

The goal, he says, is “pretty simple: someone should be able to look at a firm’s body of work and understand what it believes, why it believes it and how that thinking has developed over time.”

In one post he told readers to pay attention to the last two words of his line that reputation can compound: “over time.”

Why Reputation Compounds

Riley’s thesis, in his own words:

“I think the bigger opportunity is building a body of work over years that shows how you think, what you believed at different points in the cycle, and whether you were right. That becomes an asset in itself.”

Riley Kaminer, Founder, ClearCritical

That, he says, is what he means when he says reputation compounds like capital. He made the same case in a post about how people find content. He wrote that “the right LP may not be looking for a manager today,” and that they “might encounter the post months, or even years later.” At that point, he wrote, the post is not old content but “relevant evidence discovered at precisely the right moment.” In another post he called a firm’s content archive “an unpaid member of the investor-relations team.”

He describes ClearCritical’s work with the firms from the opening this way: “We helped turn that thinking into a consistent body of work: investor communications, articles, newsletters, media coverage and a clearer online presence. Over time, they had something they could point to. A prospective investor could see what the firm had been saying six months ago or two years ago, rather than simply taking today’s pitch deck at face value.”

The mistake, in his view, is a common one: “The mistake is treating every piece of content as a standalone marketing asset. The real value comes from what all those pieces add up to over time.”

From Journalism to ClearCritical

Riley has worked as a freelance tech writer and researcher since June 2017, and he says his work has been featured in outlets including Forbes and The Times. He is a contributing writer at Refresh Miami, where, as his profile puts it, he writes “features and news stories about tech innovation in the South Florida region.” The other role he names is his research work at StateUp, where he was an Associate and then Principal (Ecosystem) between 2019 and 2022.

He describes his path as running from journalist and researcher, to working closely with investors and founders, to founding ClearCritical, which his profile dates to September 2020.

He says journalism changed how he works with clients.

What Journalism Taught Him

“Journalism teaches you very quickly that nobody owes you their attention.”

Riley, Founder, ClearCritical

When he writes for a publication, Riley says, he learns to ask: “Why should somebody care about this? What’s actually new here? Where is the story?” Those sound obvious, he says, “but a lot of corporate content never really answers them.”

Years of interviewing founders and investors taught him to get past the first answer. “Often the interesting point comes ten minutes later, when someone stops giving you the version they have repeated 100 times and starts explaining what they actually think.” He brings that to clients. “My job is often to interview them, challenge an assumption, ask the follow-up question and find the idea underneath the talking points.” In a post, he put the same idea in one line: “Writing is basically due diligence on your own opinions.”

It is also a habit. “I ask a lot of questions. I’d much rather spend another 15 minutes on an interview than start writing before I understand what somebody is actually trying to say.” And having been on the receiving end of pitches for years, he says, he knows the gap that matters: “A company can think something is extremely important internally while there is almost no reason for anyone outside the company to care.”

One of his longtime editors, Nancy Dahlberg, has been, in his words, “such a great mentor for me over the years, helping me fine tune my journalism work and always pushing me to get to the next level.”

AI and the LinkedIn Feed

Asked for a hard moment, Riley did not name a single event. “It’s not necessarily a hard moment, but I think that the rapid rise of AI has been challenging for us all in various ways. I choose to see it more as an opportunity than a threat, but there are days when I struggle with all the AI-spurred disruptions.”

In one LinkedIn post, he wrote that 41% of long-form LinkedIn posts are now written by AI, “start to finish, then pasted in,” and that the companies and executives who keep showing up in feeds “are posting less often and making each one worth an allocator’s actual attention.” In another, on LinkedIn and AI, he wrote: “remember the tool was never supposed to replace the thinking.”

Where Riley Is Now

Riley is based in Miami, Florida, where he runs ClearCritical as its founder. The people he most wants to reach are “fund managers and investors who understand that communications should be part of how they build a firm, rather than something they turn on when they are fundraising.” If the article leads to more firms building this into how they communicate with LPs, he says, “that would be a great outcome.”

Outside work, he splits his time between writing and “a slightly excessive amount of travel.” He calls himself “a novice sommelier,” and says: “I love wine and much of my travel is to discover new wine grapes, regions, etc.” He is “happiest getting to know a city through its food, history and people.”

As for what comes next, Riley says: “I want to make ClearCritical the firm investment managers turn to when they want to build a body of work that will still matter five or ten years from now.”

Five Reflections from Riley

1. Why should somebody care? Nobody owes you their attention, so ask what is actually new and where the story is.

2. What did they say ten minutes later? The first answer is often the version someone has repeated 100 times.

3. Who will find this in two years? A post can reach the right reader months or even years later, after an introduction or during due diligence.

4. What did you believe at that point in the cycle? A body of work shows how you think over time, and whether you were right.

5. Would anyone outside your company care? A company can rate something as extremely important internally while nobody outside has a reason to care.