This is an excerpt from the book Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons on Building Great Companies, written by N. Louis Shipley and Patricia Favreau, Wiley, February 2026.
Regardless of what age founders embark on their entrepreneurial journey, there comes a time when an exit ramp looks increasingly attractive. However, some founders keep on driving rather than letting go of the steering wheel, even if it ends up hurting their company in the long run.
Bob Brennan once served as CEO of Iron Mountain, a company he helped grow into one of the largest storage and information management services in the world servicing more than 225,000 organizations, 95% of which were Fortune 1,000 companies. Now, years after stepping down from his leadership position, he quips, “It’s not a long way from ‘there goes Bob Brennan’ to ‘who’s Bob Brennan?’”
While Bob’s comment shows a keen level of self-awareness and a sense of humor about transitioning out of a position of influence, this sentiment often underpins why some entrepreneurs hold onto their company well after it makes sense to sell or step into a supportive role under new ownership. Because entrepreneurs often overcome great odds to found and grow great companies, it’s no surprise they have a hard time letting go—after all, it’s their “baby.” No one else, they may reason, truly understands the ins and outs of running the company at scale.
It’s important to avoid the temptation of making the company your identity.
But often, there’s another element at play: the level of commitment involved in growing a company may result in over-identifying with the leadership role. If you’re not grounded, I am the founder is a few steps away from who am I beyond being the founder? It’s important to avoid the temptation of making the company your identity.
Selling your company: best practices
While selling your company may bring up a range of complex emotions, you don’t want emotion driving the process. Think clearly about what you want before moving forward. Here are some best practices:
Begin with the end in mind
Entrepreneurs sell a lot more than just their company. Everything created within this space is up for sale: the product, intellectual property, brand, work culture, customer contact information, and reputation. This is why it’s so important to start your entrepreneurial journey with the end in mind. By mastering each topic we’ve explored and dissected in this book, you better position yourself for a strong finish. In particular, by assuming the role of chief salesperson, you will hone active listening skills to better understand what potential buyers need and have more experience in negotiation tactics, which will go a long way in setting yourself up for a premium exit.
Market your company’s scarcity value
It’s important to differentiate your company from other competitors looking to sell. Emphasize to potential buyers not only your product’s unique features but also the depth of your customer relationships and the breadth and maturity of your employees.
Understand the realities of your ownership stake
If you own 100% of your company, the decision for price and terms is yours alone. If you own less than 50% of the company, your board of directors—most often comprised of investors and independent directors—must vote on the decision to sell and at what price. The sales skills you’ve honed over the years will come in handy if you need to convince your investors that it’s the right time to sell. Be aware that it may take compromise to reach a deal.
Even if product synergies are strong, if there is a cultural mismatch, the acquisition will fail.
“Sell” your workplace culture
According to Tom Bogan, former CEO of Adaptive Insights and former vice chairman of Workday, “Culture is the single most important determinant of success or failure when large companies acquire smaller companies. Acquiring companies consider a start-up’s culture as much as they look at product strategy and sales growth when considering an acquisition.” In short, acquirers want to know if the prospect company’s employees will enjoy working for them and buy into their company’s mission and culture. Even if product synergies are strong, if there is a cultural mismatch, the acquisition will fail.
Learn how the acquisition process works
If you are being acquired by a larger company, be aware that each company acquisition is a unique transaction. For example, an acquirer may offer to pay you cash or company stock for your business or an “earn out” where you get paid over a predetermined period of time. A deal like this is likely to have performance conditions that the acquired company must meet for you to receive payment. The acquirer may also require you to remain at your company for a certain period.
Fix your problems
Potential buyers do not want to inherit a company’s problems. It’s imperative to improve areas where a company is underperforming before attempting to sell. If it’s evident that your sales are slowing down or your product needs upgrading or your work culture is subpar, you may inadvertently signal that you must sell. This puts buyers in a better position to negotiate and drive down your asking price.
Ideally, you want buyers to approach you about selling your company. If it’s thriving, buyers will offer a higher price than if you put the company on the market or sell through a broker. In essence, great companies are bought, not sold.
Excerpted with permission from the publisher, Wiley, from Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons on Building Great Companies by N. Louis Shipley and Patricia Favreau. Copyright © 2026 by John Wiley & Sons, Inc. All rights reserved. This book is available wherever books and eBooks are sold.
