Kevin Ryan has had a long and storied career as a pivotal force of New York City tech. He’s the founder and CEO of investment firm AlleyCorp, which has invested in a wide variety of startups, and is a serial founder, participating in the early stages of companies such as Business Insider, Zola, Gilt, Pearl Health, and Transcend Therapeutics. He helped build ad tech company DoubleClick as president and CEO in the 1990s and early 2000s, and Google later bought it for $3.1 billion in 2007, transforming the online advertising industry. He went on to co-found unstructured database provider 10gen, which later changed its name to MongoDB and went public in 2017.

Last Tuesday, I interviewed Ryan to discuss pivotal moments in company transformation for the benefit of the companies chosen for this year’s Startup Battlefield 200 at TechCrunch Disrupt.

As a part of the Startup Battlefield 200 program, the selected founders participate in pitch training workshops as well as a series of exclusive master classes with top-tier VCs, successful founders and operational experts. The virtual program aims to prepare and excite them for what is to come when they exhibit, demo and pitch at Disrupt in October.

During Ryan’s session, he offered a lot of useful advice for companies at all stages, from finding a great cofounder, to when and how to seek funding, to how a founder’s focus should change as a company scales.

But given his background with DoubleClick and MongoDB, I asked him how company founders should decide when and whether to take an acquisition offer, versus when they should hold on and try 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 everyone else?”

He added, “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 believe] 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 going to 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].”

He added that lot of founders don’t think clearly when it comes to personal wealth from an acquisition, chasing ever-bigger numbers instead of settling for a life-changing amount of money. And by not settling, they often end up with zero instead.

“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 added, “It sounds great to make 60, 90, 100. It actually doesn’t change your life very much.”  

You can watch the whole interview here.