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Home » Insight VC explains the biggest mistakes that prevent founders from raising big rounds
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Insight VC explains the biggest mistakes that prevent founders from raising big rounds

userBy userMarch 10, 2025No Comments5 Mins Read
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Given how much money VCS is putting into AI startups these days, it may seem like it’s decided. If it’s not AI, then they won’t write big checks.

But that’s not exactly what’s going on. The deals are more subtle at the moment, Ryan Hinkle, managing director at VC Insight Partners, said in a recent Equity Podcast.

Our Insight Partners manage our $90 billion assets, so we invest at every stage. It is known to have written huge checks in itself and stacked up in huge rounds. Insight, for example, will co-led the December $10 billion deal. He participated in Abnormal Security’s $250 million Series D in August (led by Wellington Management). It is using Clearlake at the end of 2023 to jointly lead Alteryx’s $4.4 billion PE take private deals.

Hinkle, who started out as an intern in 2003 when the company was 10 years old, explained how the company’s pace of check writing has grown.

“When we joined Insight, we were raising a cumulative $1.2 billion with four funds. At that point, we only put $750 million in capital into our investment. We’re doing more than $1 billion per quarter today,” he said.

“All of these decades, $750 million has been invested, and this is like a good month for us today,” he joked. (Insight raised $12.5 billion for XIII’s flagship fund.)

He said that growing companies that do not sell AI as core technology (e.g. Last Cycle’s beloved, SaaS companies, etc.) can still raise healthy checks. But the multiples they can expect – compared to revenue – isn’t that high.

The funding round is “30% lower on ARR-based multiples than in 2019,” he said. “Stocks are increasing as corporate revenues are rising significantly, but multiples are still low.”

Hinkle likes to call these current times “a great reset” and says, “it’s very healthy.”

However, there is one big thing founders can do to maximize the transactions that Growth VCS offers, and it’s not just stamping AI across the company’s marketing material. It’s far more important and far more common. Financial infrastructure.

Show finances

Startups do not need to participate in the Growth Round (Series B and later), but they don’t necessarily need a CIO, but they need a system that provides details beyond recent customer acquisition and their cousins ​​and their repetitive annual revenue.

That number became popular with the rise of SaaS when startups signed multi-year contracts with customers but were unable to recognize revenue only after they were billed. Today, startups want to make profits for the recent month, and have been completed with 12, arr.

The financier Hinkle wants is that startup leadership can answer everything about business, including margin impact, customer retention rates, “every step from quote to cash, every step from giving customers a payment to being paid, and more.

“Can I create an anonymized customer record for me for all transactions with each customer?” Hinkle asks. This should include both the invoice and some contract details.

“And if it requires more than pressing a button, the question is, ‘OK, is it all preserved? And why is it potentially scattered?” he said.

In many cases, young startups start with a Kluged system with billing data in one place and are contracted somewhere. The reservation data and contract period may be located somewhere. And no one has reconciled it all.

For many people, especially those with impressive growth rates, working on these mundane financial systems will not prioritize adding product features that will lead to more contracts.

“When you’re 100% growing, I’ll get it perfectly, spoiler alerts, metrics are good,” Hinkle said. But at one point he warned that growth would likely hit the skid from his competitors.

“All of a sudden you need to improve your sales math, unit math,” he said. “And if you can’t see it, it’s hard to know which lever you’re affecting.”

Founders who don’t document their financial minutes hurt themselves during the VC’s hard work process. And it will almost certainly hit the check size or rating.

“We’re still in the aftermath of this hangover reset. “Many of us were seriously burned.”

Once founders were able to walk away with a great check from a good revenue growth chart and a clear vision of the future. Today, “If you can’t see it with your own eyes, it doesn’t exist,” Hinkle said. “Therefore, there’s a focus on these metrics.”

It is true that some VCs will overlook that level of hard work and invest anyway, as they are still “intoxicated” by the number of growing numbers, Hinkle acknowledged.

But he warned, the problem never fades. As a company grows and acquires more customers in more transactions, financial governance becomes more cumbersome when it doesn’t have a system of tracking and coordination in place. The sooner the founders handle it, the better the business will later become.

Here are the full interviews he discusses about this, as well as other topics like:

Why startup success is not tied to a single location, but rather the abundance of opportunities in Silicon Valley creates a “mercian” employment culture, making it difficult to maintain employees and make important differences between Silicon Valley buildings and Silicon Valley including access to financial management and venture capital


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