Kevin Ryan has had a distinguished career as a key player in New York City's tech landscape. He is the founder and CEO of AlleyCorp, an investment firm that has backed numerous startups. Ryan has been instrumental in launching companies such as Business Insider, Zola, Gilt, Pearl Health, and Transcend Therapeutics. He also played a crucial role in building DoubleClick as its president and CEO in the 1990s and early 2000s, leading to its acquisition by Google for $3.1 billion in 2007, which revolutionized the online advertising industry. Furthermore, he co-founded 10gen, which later rebranded as MongoDB and went public in 2017.

Recently, I had the opportunity to interview Ryan about pivotal moments in company transformation, particularly for the founders participating in this year’s Startup Battlefield 200 at TechCrunch Disrupt. This program provides selected founders with pitch training workshops and exclusive master classes with prominent VCs, successful founders, and operational experts, gearing them up for their presentations in October.

During Ryan's session, he shared valuable insights for companies at various stages, covering topics from finding an ideal co-founder to when and how to pursue funding, as well as how a founder’s focus should shift as a company scales. Given his extensive background with DoubleClick and MongoDB, I asked Ryan how founders should decide when to accept an acquisition offer versus holding out for a potential IPO.

“There’s no formula,” he stated. “What I’m considering is, first, what do our prospects look like? We shouldn't be delusional—how much are we growing, what will the company look like in three years, and what are the exit strategies? Also, how many other buyers are there, and how do we compare to others?”

He emphasized the importance of the time factor: “If we’re worth $100 today, four years from now, we need to be worth $200 just to break even due to risks and costs. Are you prepared as CEO to believe we’ll be worth $300? If so, we should hold on. But if you think it’ll only reach $150 or $170, we should probably sell now, because markets can close unexpectedly.”

Ryan suggested that many founders should consider selling earlier rather than aspiring to become the next Mark Zuckerberg, who famously declined a $1 billion offer from Yahoo in 2006.

“I believe more people should sell than actually do,” he remarked. “You might hear about the $20 billion company that turned down an offer, but there are countless examples of founders who could have sold.”

He noted that many founders don’t clearly assess their personal wealth from an acquisition, often chasing larger sums instead of accepting a life-changing amount of money. This pursuit can lead to them ending up with nothing.

“I recently had a conversation where someone could sell now for $30 million, which is life-changing,” he said. “A year later, they could pursue many opportunities. But in reality, making $60 million doesn’t significantly increase happiness compared to $30 million; however, $30 million is a huge difference from zero.”

Ryan concluded, “While it sounds appealing to aim for $60, $90, or even $100 million, the truth is it doesn’t impact your life as much as you might think.”