For VCs, the game right now is musical chairs

In many ways, there has never been a better time to be a venture capitalist. Nearly everyone in the industry is raking in money, either through long-awaited exits or because more capital flooding into the industry has meant more money in management fees - and sometimes both.

Still, a growing number of early-stage investors are becoming wary about the pace of dealmaking. It's not just that it's a lot harder to write checks at what feels like a reasonable clip at the moment, or that most VCs feel they can no longer afford to be price sensitive. Many of the founders with whom they work are being handed follow-on checks before figuring out how best to deploy their last round of funding.

Consider that from 2016 through 2019, an average of 35 deals a month featured rounds of $100 million or more, according to the data company CB Insights. This year, that number is closer to 130 of these so-called mega-rounds per month. The froth is hardly contained to maturing companies. According to CB Insights's data, the median U.S. Series A valuation hit $42 million in the second quarter, driven in part crossover investors like Tiger Global, which closed 1.26 deals per business day in Q2. (Andreessen Horowitz wasn't far behind.)

It makes for some bewildering times, including for longtime investor Jeff Clavier, the founder the early-stage venture firm Uncork Capital. Like many of his peers, Clavier is benefiting from the booming market. Among Uncork's portfolio companies, for example is LaunchDarkly, a company that helps software developers avoid missteps. The seven-year-old company announced $200 million in Series D funding last month at a $3 billion valuation. That's triple the valuation it was assigned early last year.

It's an awesome company, so I'm very excited for them," says Clavier.

At the same time, he adds, You have to put this money to work in a very smart way."

That's not so easy in this market, where founders are inundated with interest and, in some cases, are talking term sheets after the first Zoom with an investor. (The most absurd thing we've heard are funds that are making decisions after a 30-minute call with the founder," says TX Zhou, the cofounder of L.A.-based seed-stage firm Fika Ventures, which itself just tripled the amount of assets it's managing.)

More money can mean a much longer lifeline for a company. But as many investors have learned the hard way, it can also serve as a distraction, as well as hide fundamental issues with a business until it's too late to address them.

Taking on more money also oftentimes goes hand-in-hand with a bigger valuation, and lofty valuations comes with their own positives and negatives. On the plus side, of course, big numbers can attract more attention to a company from the press, from customers, and from potential new hires. At the same time, The more money you raise, the higher the valuation it is, it catches up with you on the next round, because you got to clear that watermark," says Renata Quintini of the venture firm Renegade Partners, which focuses largely on Series B-stage companies.

Again, in today's market, trying to slow down isn't always possible. Quintini says that some founders her firm has talked with have said that they're not going to raise any more, explaining that they cannot go faster or deploy more than their business model is already supporting For others, she continues, You've got to look at what's happening around you, and sometimes if your competitors are raising and they're going to have a bigger war chest and [they're] pushing the market forward and maybe they can out-hire you or they can outspend you in certain areas where they can generate more traction than you," that next check, often at the higher valuation, begins to look like the only path to survival.

Many VCs have argued that today's valuations make sense because companies are creating new markets, growing faster than before, and have more opportunities to expand globally, and certainly, in some cases, that it is true. Indeed, companies that were previously believed to be richly priced by their private investors, like Airbnb and Doordash, have seen their valuations soar as publicly traded companies.

Yet it's also true that for many more companies, valuation is completely disconnected from the [companies'] multiples," says Clavier, echoing what other VCs acknowledge privately.

That might seem to be the kind of problem that investors love to face. But as been the case for years now, that depends on how long this go-go market lasts.

Clavier says that one of his own companies that did a great Series A and did a great Series B ahead of its time is now being preempted for a Series C, and the valuation is just completely disconnected from their actual reality."

He says he's happy for the outfit because I have no doubt they will catch up. But this is the point: they will have to catch up."

For more from our conversation with Clavier, you can listen here.