What Investors Want Now: Cash, Not Decks — Checchia

Capital has not disappeared. It has become harder to please, and founders who could raise on a deck two years ago are finding the same conversation goes differently now. What does the money actually want to see? Robert G. Checchia’s answer is cash, and his explanation of why runs from the Japanese bond market to the exit queue in private equity.

Checchia is a CFA charterholder and, at the time of recording, Chief Financial Officer of Benzinga. The company is a breaking-news and analysis provider covering the US markets. It sells to retail investors by subscription, to brokerages and asset managers who pass the analysis on to their own clients, and to advertisers, which he describes as the smallest part of the business today.

What follows sets out why he expects the unwinding of the dollar trade to continue, what he reads into the prices people are paying for collectibles, why private equity is sitting on its holdings longer, and what all of it means for a company trying to raise. It is the material a founder needs before setting a valuation, and the material an investor needs before underwriting one.

A CFO Who Arrived Mid-Way Through a Private Equity Hold

Checchia joined a business already owned. In his words, “I arrived at year two of the investment”, with a brief to bring maturity to the finance function: accounting, planning, reporting, transparency and governance, built from the ground up.

What the role became is the more interesting part. Because his team automated and streamlined much of the reporting, his own week now looks closer to a chief operating officer’s than a chief financial officer’s, spent building businesses rather than analysing them.

He connects that to a shift he has been reading about among consultants leaving the big strategy firms. Where the usual next step was private equity or venture capital, the largest destination now is an operating role. Having been a consultant himself, he is comfortable naming the difference: analysis is deep and interesting, but an operator carries accountability for a result.

Owners recruiting a finance chief can take a practical read from this. The question worth asking in an interview is not what the candidate would analyse, but which functions they have personally rebuilt.

Why He Expects the Dollar Trade to Keep Unwinding

His diagnosis of the macro picture is monetary. Expansion in the United States has been too loose, he argues, and fiscal sustainability insufficient, with the result that overseas holders are selling down their US Treasuries.

Japan sits at the centre of it. Interest rates there have been extremely low for as long as anyone can remember, which made the country the world’s financier, and that behaviour is now changing. On his reading the carry trade unwinding is at the tip of the iceberg rather than near its end.

I don’t see any change in monetary fiscal policy happening in the US at the moment. So, nothing indicates to me that it’s going to be a reversed trend.

The consequence he draws is a multipolar one. Safe-haven status for the dollar is being challenged, in his view only at the beginning of that process, and investors will hold a broader basket of stores of value in response, including gold, exposure to the Chinese yuan and physical assets.

His near-term forecast is specific: “So, I see 12 months of stability upwards and then 12 to 24 after that of unwinding a little bit more of the US equity markets.”

Treasurers and allocators can treat that as a testable view rather than a mood. It names a direction, a sequence and a rough timetable, which is more than most macro commentary offers, and it can be checked against what happens.

What Collectible Prices Tell Him About Liquidity

The evidence he finds most telling is not in the bond market at all. Having worked in finance throughout his career and watched the NFT cycle come and go, he now sees people bidding up vintage whiskey, art, Pokémon cards and toys from the 1980s.

His interpretation is unsentimental. When buyers pay those prices, it says less about the objects than about the quantity of money looking for somewhere to sit, which he reads as inflation being allocated to everything rather than value being stored.

That is why his own money goes elsewhere. Cash-producing assets are where he is heavily invested personally, on his own account, in equities and in real estate, the latter on the straightforward argument that the United States cannot build houses fast enough for its population.

For business owners the distinction is the one that matters most in a repricing. An asset that throws off cash can be held through a bad market; an asset that only appreciates has to be sold to be worth anything, and the selling window is exactly what closes first.

Longer Private Equity Holds as a Valuation Signal

The second piece of evidence is how long sponsors now sit on what they own. Across multiple sources he recalls seeing, the average holding period has stretched from 4 to 5 years to seven, and in some cases to between 7 and 10 years.

His reading of that is not about patience. If the valuation multiple underwritten at entry is no longer available at exit, the rational move is to keep the asset, collect the cash it produces and wait for a better moment. A lengthening hold, seen that way, is a quiet mark-down.

Founders planning an exit inside a fund’s life should note what this does to the queue. A sponsor holding for longer is a sponsor whose next fund needs realisations, which eventually shapes what they are willing to pay for the next asset in.

What a Company Now Has to Show to Raise

The host put to him a shift she had observed in European venture, where seed and pre-seed funding dried up and series A became the effective entry point, with revenue or a working beta as the minimum. He agreed and extended it.

His account of what allocators want is blunt: proof rather than presentation, generated cash rather than a model of it, EBITDA and recurring revenue rather than a minimum viable product. Adding artificial intelligence to a concept, in his description, no longer substitutes for a business.

That filter is the same one visible in the collectibles and the holding periods.

Founders should read the change as one of sequencing rather than of appetite. Capital is still available, but the evidence has to exist before the raise rather than being funded by it, which pushes the hard work of building revenue in front of the fundraise instead of after it.

AI Inside a Financial Publisher, and Why Nobody Was Cut

Benzinga is deliberately repositioning from a financial publisher into a financial technology company, a shift he attributes partly to a chief executive with a technology background. The concrete measure is hiring: from no data scientists or data engineers three years ago to a team of 15, working on productising the information the company holds.

Internally the tools are used heavily, for analysis, trend review and understanding who the audience is. The editorial line is the opposite, since every piece of content published is human produced and verified, and the video output, including the morning show, is deliberately not automated.

We haven’t fired a single person and we don’t intend to because of AI.

Distribution is where the technology changes the commercial picture. Search optimisation has given way to what he calls generative engine optimisation, and most of the company’s traffic is no longer organic, arriving instead through aggregators, major brokerage apps and partnerships with AI providers whose platforms now carry the content.

Marketing leaders should notice which half of that is defensible. The tools are available to every competitor, so the asset is the human-verified content and the distribution agreements, not the automation.

What separates one company from another in his account is whether it produces cash or promises it. That test is being applied at every level at once, by allocators pricing a seed round, by sponsors deciding whether to sell, and by investors deciding what to hold while the dollar’s position is renegotiated.

Robert G. Checchia set out his reasoning at greater length in Cash Flow Over PowerPoint Hype What Investors Want Now Benzinga CFO Robert Checchia on the GrownLearn podcast.

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