I Rewrote the Boomer Script — My Millennial Entrepreneur Journey

Learning from the Past, Shaping the Future

There's a secret I'm willing to share that might not be popular with my fellow millennials: I learned a lot from my Baby Boomer dad. Watching him work long hours—60, 70, even 80 hours a week—growing his business, shaped my early understanding of what it means to build something meaningful.

When I started my first business, I followed a traditional path that many Baby Boomers took. Life was seen as a three-act play: the first act was about self-discovery and figuring out your purpose; the second act involved building a successful business; and the third act was about living a life of significance beyond the business itself.

But I’m still a millennial. So when I sold my first business at a young age, I felt like I was missing something. I regretted the sale almost immediately, and months turned into a year as I searched for my next step in life. I had broken the script and was looking for personal purpose. My phone wasn’t ringing anymore, my name wasn’t on a truck, and I had no one to work with.

That’s when my dad gave me some advice that helped me realign with my peers. He told me, “Don’t fall in love with your business. Fall in love with business.” It was a simple but powerful message that resonated with me.

What Millennials Value

Millennials have big plans for their lives, but those plans don't always follow a straight path. We value meaningful work, and that meaning can evolve over time. Our first act was defined by the dawn of the new millennium and significant technological changes. We adapt, which is why we often have multiple jobs throughout our careers. In fact, according to Gallup, 21% of millennials changed jobs in 2024.

We’re also ambitious. The Exit Planning Institute conducted a nationwide survey of business owners in 2023, called the National State of Owner Readiness Report. Among the surveyed generations, millennials had the highest percentage of companies with annual revenue over $100 million—20%. They were also more likely to track business value formally, with 65% of millennial owners doing so compared to 47% of Gen X and 33% of Baby Boomer owners.

Another key trait of millennials is our tendency to spend. According to a report from Boston Consulting Group, millennials with household incomes over $250,000 were the most likely generation to spend on luxury goods. For us, growing the value of our company isn’t just about harvesting wealth—it’s about planning for a "boomerang exit," where we buy or invest in another company after selling our current one.

In fact, 85% of millennials plan to buy or invest in another company post-exit, which is significantly higher than other generations, including Gen Z.

Focal Points for Exit Planning

So, where should millennials focus when it comes to exit planning?

1. Drive Value, With Framework

The good news is that no generation focuses more on exit planning education than millennials. The 2023 National State of Owner Readiness Report showed that our generation is most likely to believe that having a transition strategy is important for the future. We are also more likely to be familiar with all of our exit options and seek outside advice at a higher rate.

However, we often struggle to stick to a framework for driving value in our businesses. That’s where a Certified Exit Planning Advisor (CEPA) can help. The Value Acceleration Methodology used by CEPAs calls for a three-year strategy, followed by a one-year plan, which is executed through 90-day sprints. This structured approach helps prepare for a boomerang exit and builds a business that will be attractive to potential buyers.

2. Focus on Financial Planning

Good exit planning requires balancing what the Exit Planning Institute calls the "Three Legs of the Stool"—business planning, personal planning, and financial planning. While millennials excel at personal planning, we often need to focus more on financial planning, especially since we tend to earn to spend.

According to the 2023 National State of Owner Readiness Report, only 40% of millennials named their personal financial advisor as their most trusted advisor, lagging behind Gen X and Baby Boomers. Don’t think of your financial advisor as just a retirement advisor. A diversified portfolio can help you navigate your business exit and re-entry while still meeting your current financial goals.

3. Decentralize

As a generation, we're less likely to want the long workweeks that Baby Boomers prized. We prioritize work-life balance, having seen our parents regret not having it. Even though we’re less likely to hold onto a business for a long time—48% of millennial owners plan to transition within five years—we still need to align our personal and business goals.

Focusing on driving value in people, systems, customers, and culture can help your business run smoothly while allowing you to spend more time on the things that matter to you outside of work.

Lean Into What Makes You Great

Generational differences aren’t about deficiencies—they’re about what defines us. Knowing your strengths as much as your weaknesses can help you identify your goals and find support for the areas you're not naturally inclined to focus on.

Finding a diverse team of advisors can help you achieve your goals and live the life you want—both at work and at home. Ideally, this team should be led by a Certified Exit Planning Advisor, someone who can assess your business, personal, and financial goals and guide a team of advisors to set you up for success and significance.