That jarring silence is what hit Dr. Tony Jacob hardest after selling his multimillion-dollar business. One day, he was the CEO, fielding hundreds of messages, making crucial decisions, and leading a team across dozens of locations. The next? Nothing. Just the echo of his own thoughts.
This is the reality no one tells you about when you sell your company. Your calendar empties. Your phone stops ringing. The purpose that drove you for years vanishes, replaced by a daunting question: “What now?”
How Does life Change Immediately After a Business Exit?
The day after selling his company, Dr. Tony Jacob experienced something unexpected: silence.
Many entrepreneurs initially enjoy their newfound freedom. “There’s two or three months where you really revel in, ‘Wow, I’ve got a lot of free time. What am I going to do with myself?'” Tony explained on the Lifestyle Investor podcast. But this honeymoon phase eventually gives way to deeper questions.
“After you come out of it, it can be very disorienting,” he notes, “especially because your day-to-day was so vastly different. You might be home more with your family. Your friend group has changed.”
Such a profound change in routine demands adjustment, regardless of newfound financial security.
Why Should you Wait Before Making Major Investment Decisions?
After his exit, Dr. Tony Jacob made a counterintuitive choice: he waited a full year before making significant investments, a patience that proved invaluable for his long-term success.
“Having money burning a hole in your pocket is a dangerous thing,” Tony warns. “There is nothing wrong with waiting, maybe a year or even two years and really understanding what you’re getting yourself into.”
What financial structures work best after a major exit?
Following a significant liquidity event, entrepreneurs must decide how to structure their assets. Many establish a family office, an organization that manages investments and finances for a wealthy individual or family.
Dr. Tony Jacob outlines several approaches to this challenge:
- A single family office supporting your family.
- A multifamily office serving 50-200 families.
- A collaborative arrangement where friends pool resources.
- A hybrid approach combining professional management and self-directed investing.
“It’s not one size fits all,” Tony emphasizes. “You can definitely hybridize it to whichever way you want.”
His own evolution into a family office structure happened naturally. “I was building into this family office, which was a term I was unfamiliar with in 2021… really. 2023 was when I realized that’s what I was doing.”
How Does the Entrepreneurial Mindset Shift When Becoming an Investor?
The transition from entrepreneur to investor requires a fundamental shift in thinking. While building a business demands concentration of resources, preserving wealth requires diversification and strategic allocation.
“The diversification game is a different game than the accumulation game,” Tony explains. Most entrepreneurs build wealth through concentration in their business, but preserve it through diversification across multiple asset classes.
This shift can be challenging because the skills that made someone successful as an entrepreneur don’t necessarily translate to investing. “I didn’t really know how to invest,” Tony admits. “I kind of had to learn trial by fire, make a couple of mistakes along the way.”
Becoming an effective investor means developing new expertise and adopting a longer-term perspective than many entrepreneurs are accustomed to.
What Role Does Education Play in Post-Exit Success?
For Dr. Tony Jacob, education became a critical focus after selling his business. “One of those things you do is you start learning new things and I love to learn,” he explains.
This learning process includes both formal education, such as joining investment groups, and learning through experience. Tony believes in balancing education with patience: “We can rush into education, but let’s not rush into investing.”
The educational journey often involves connecting with others who’ve walked a similar path. Tony emphasizes the value of community in navigating post-exit life, noting the importance of learning from those with more experience.
This commitment to continuous learning helps former entrepreneurs avoid costly mistakes and make more informed decisions about their newfound wealth.
Questions About Post-Exit Investment Evolution
Q: How long should I wait after an exit before making major investments?
While every situation differs, Dr. Tony Jacob recommends waiting at least a year to develop investment knowledge and clarity about your goals. This patience helps prevent emotional decisions that often come with sudden liquidity.
Q: Should I manage my investments myself or hire professionals?
Most successful post-exit entrepreneurs use a hybrid approach. Start by understanding investment basics yourself, then gradually build relationships with trusted advisors who have specialized expertise. As Tony explains, there are many ways to structure this arrangement based on your needs and preferences.
Q: How important is estate planning after a business exit?
Estate planning is crucial after a major liquidity event. Completing estate planning before an exit is ideal, as it creates more tax strategy options and simplifies the process. After an exit, estate planning becomes more complex but remains essential for protecting and transferring wealth.
