In the early stages of entrepreneurship, passion means pouring your blood, sweat and tears into creating a viable business. But even then, why do most startups eventually fail? And why isn’t longevity more common in entrepreneurship? Is it a lack of traction? Money? Drive?
Eric Becker, author of The Long Game, says, “The number one reason that companies fail is not understanding what the reality really is and then confronting it, no matter how uncomfortable that might be.”
As the founder and co-chairman of wealth management firm Cresset, an asset management business, Becker summarizes what is steering—and more importantly, sinking—companies. His main argument is that companies face a “distortion of reality” that prevents them from growing.
Holes in the Plan
At a company’s startup stage, progression is rapid. Becker calls this the invention/creation phase, where, essentially, every aspect is close-knit and “scrappy.” As the business expands, it becomes institutionalized, and it grows structured and larger; therefore, it must adapt to a new skill set.
The second focus is culture. He notes that this is when companies need to get comfortable with recognizing when someone isn’t a good fit on their team or when the company has outgrown some employees. While these issues are considered minor, they can compound and cause greater consequences.
He details these points in his book, which was inspired by a company he saw listed in a local business publication 30 years ago. It was a family-owned small business that lasted 200 years because they kept pivoting.
“I’m like, ‘How does a small family business last 200 years?' That’s the Civil War and depressions and recessions and pandemics before we had a pandemic; they’d already been through it before, so it piqued my curiosity,” Becker says.
He ended up interviewing them and then began to study patterns of organizations and businesses that lasted over 100 years to understand “the value of what’s old, what’s proven, what has stood the test of time.”
Here are Becker’s key points from The Long Game:
The myth-busting mindset: Older companies are often viewed as bureaucratic, but it’s actually false. These companies develop survivability DNA, take action, and overcome disasters and challenges.
Moments of truth and trust: In business and real life, there are 15 to 25 decisions that significantly shape the future. In entrepreneurship, these calculated decisions are make-or-break moments.
Right people: Plan for the future generations. Select people who see themselves as vital parts of the organization. These individuals hold immense responsibility and safeguard your business.
Ethical succession: Proper succession planning goes beyond choosing someone you know or who is in line to inherit the business. “Many people pick their successor [for the incorrect reasons] because it feeds their ego,” Becker says. Choosing someone who understands the company and can carry it forward is how a business can ensure long-term adaptability and growth.
The Super-Proof Trick
Becker launched his company, Cresset, nine years ago by embracing core values. They’ve grown exponentially since, and now, the company is owned by the employees and its clients. He stresses that longevity doesn’t exist without the right vision and culture to grow.
“That act of entrepreneurship and of a startup is [that] you have to have the willpower,” Becker explains. “You are willing your idea to come into reality, and everything is against you. The status quo is against you. No company that’s preexisting wants you to succeed. They want you to fail, because if you succeed, it’s coming at their expense.”
He also advocates for super-proofing (also known as future-proofing). Entrepreneurs must first understand the power of compounding—not just money, but knowledge, relationships and pieces of their business.
Knowledge grows just like money: “The earlier you start to learn something, the better you’re going to be three years and five years from now,” he says.
The same applies to relationships. “Think about your own most powerful relationships in your life and how meaningful and valuable they are to you,” Becker advises. In the future, those relationships should compound as well for strong business relationships.
This is achieved by hiring passionate individuals aligned with the company’s vision who are willing to take risks. Financial discipline and ongoing improvements to the business model keep the business propelling.
Evaluating Leadership
Great leadership carries weight when it comes to thriving as a business while maintaining happy employees. Becker sees leadership as balancing two components: competency and humanity.
Leaders who can execute plans effectively, with the right skills and experience, combined with leaders who bring human qualities of empathy, curiosity and inspiration, can navigate those challenges. Becker says this is what he continues to seek in leaders—and in himself.
“I work on it in my own skills and development, even at 63 years old, where I’m always looking to see, Where can I get better at this as well?" Becker says. He encourages everyone to keep learning from others and oneself, as the human element will never fail us if we count on it, especially in the realm of AI.
Tried-and-True Results
Becker says people are always looking for what’s new and innovative. New, fast-paced methods and strategies are indeed at the helm of change. However, he emphasizes that older business knowledge and wisdom should not be underestimated since they paved the way for advancement.
“I’ve now learned there’s so much that we can benefit from these organizations that have stood the test of time, and we need to knit that together with our fascination and what’s new, and put them together,” he says.
Featured image from PeopleImages / Shutterstock.com
This article was first published in the May/June 2026 issue of SUCCESS Magazine. Get your copy here.
