Kevin Ryan has had a storied, long-term history as one of the most pivotal forces in New York City tech. He is a founder and chief executive officer of investment firm AlleyCorp, which has invested in a wide range of startups and was involved in a series of successful startups, such as early companies Business Insider, Zola, Gilt, Pearl Health, and Transcend Therapeutics. He helped build the ad tech company DoubleClick during his tenure as president and CEO of the 1990s and early 2000s; Google later bought it for $3.1 billion in 2007, transforming the online advertising business. He co-founded MongoDB as well as 10gen, which is now known as MongoDB and went public in 2017.

Last Tuesday, I spoke with Ryan to discuss standout moments in transformation for the companies selected to Startup Battlefield 200 at TechCrunch Disrupt this year.

By the way, founders selected for the Startup Battlefield 200 program will participate in pitch training workshops and a series of exclusive master classes with top-tier VCs, successful founders, and operational experts. The virtual program is intended to get them prepared and geared up for what awaits them when they exhibit, demo and pitch at Disrupt in October.

During his session, he provided loads of super valuable advice for companies at every stage-from finding a fantastic cofounder, to when and how to seek funding, to how a founder's focus should change as a company scales.

But, of course, with his background at DoubleClick and MongoDB, I asked him, how do company founders know when to hold 'em, and when to fold 'em, or whether and when they should take an acquisition offer versus trying to go public?.

"There's no formula but what I'm thinking about is, one, what do our prospects look like?" he said. "Let's not be delusional-how much are we growing, what is this company going to look like in three years, what are the exit strategies, then how many other people-other buyers-are there, how are we doing relative to everybody else?"

He says, "Most people underestimate the time factor, so if we're worth $100 today, four years from now it's got to be worth $200 just to break even because of risk, cost of capital, things like that. So are you signing up as CEO [because you think] that we're going to be worth $300? If you really believe that then we should hold on.". But if you just think it's gonna be $150 or $170, we should probably sell today because also you need to factor in: Markets can close at any time. You and I over 25 years could name many things we didn't see coming. The Ukraine war. No one saw inflation coming. No one saw many things coming….and all of a sudden everything's dead.

By and large, he said, more people should sell earlier, rather than holding out to try and become the next Mark Zuckerberg, who famously turned down a chance to sell Facebook to Yahoo for $1 billion in 2006. Disclosure: Yahoo owns TechCrunch.

"I think more people should sell than probably sell on average," Ryan told me. "You're definitely going to read the story of the $20 billion company that turned something down, but there are a lot of other examples of people that could have sold."

But that's not to say the founders thought hard about personal wealth, he said. Many just go for ever-bigger numbers instead of getting a life-changing amount of money. And by not settling, they very often end up at zero.

"I had this conversation the other day," he said. "Someone could sell now and they're going to make $30 million. $30 million is an incredible amount of money. It's life changing, right? And they can… a year later go off and do so many things. And you know what? $60 million doesn't make you much happier than 30, right, but 30 it makes a big difference from zero."

He says, "It sounds great to make 60, 90, 100. It actually doesn't change your life very much."