Whenever I'm in speaking with successful business owners, the conversation often veers toward the endgame. That is: What are you going to do after you cash out?

You've got some interesting choices. Do you give back to the community (start another business; become an angel investor)? Or do you reap your well-earned rewards and treat yourself to that Tesla or island getaway?

Giving Back

The decision isn't cut-and-dried. Universally, top entrepreneurs credit their success to the community that supported them. So the desire to give back should be strong. But it's a decision that matters more than you think. A vibrant business community is a robust ecosystem of companies, employees, investors, and mentors. If successful business folks stay engaged, it helps the community prosper.

I call this the "cycle of reinvestment."

It sounds great in theory. But there’s always a glitch. An acquired company could be forced to move. And, not infrequently, the founder may also leave town--or just stay put and disengage.

Here's how it ideally works: The founder launches a startup. The capital used to support growth-;and the cash that goes along with it--flows into the community (which means jobs and business opportunities). The founder sells out and is rewarded. Then, in most cases, he or she launches another business, becomes an investor in a startup, or maybe even both. One region where entrepreneurs are taking the lead to build a network like this is in my own backyard: in North Carolina’s Research Triangle Park (read about RTP's ecosystem on ID8 Nation, on online magazine featuring startup communities). The Blackstone Entrepreneurs Network identifies serial entrepreneurs--folks who have run multiple businesses--and brings them together as a team to work with founders of young ventures. 

The Blackstone project demonstrates that it is important for the business community to keep former owners involved. Keep the gift giving, in other words. Surprisingly, local leaders don’t know how to keep the cashed-out in the fold. And often, the former owner doesn’t know how to get involved in the first place.

So, how to make your postsale period work? Some advice:

Coach: Ex-business owners know markets, customers, and what mistakes to avoid. Make connections with companies that interest you and become an informal adviser. Universities often have startup programs and accelerators and are looking for experienced mentors. You can also seek out the "connectors" in your community: that dealmaker, attorney, or accountant.

Teach: With the proliferation of entrepreneurial programs, universities are looking for instructors with entrepreneurial experience. Nothing helps the cycle of reinvestment more than an influx of rookies. My class at UNC, "Launching the Venture," has produced more than 100 real companies over the past 10 years.

Invest: For ventures you believe in, lead a capital round, form a syndicate, or make introductions. Join an angel group, or become a limited partner with an established venture fund in the early-stage market and help the firm do due diligence on the rising stars. In the Research Triangle, for instance, about 60 percent of the serial entrepreneurs and investors know one another; in Silicon Valley, the figure is much higher: almost 100 percent. That’s a great network for young companies to tap into. 

Get involved in the community: Sponsor meet-ups and events to build the business network. Draw your best talent to these events. Lend your expertise to forming a network of business leaders that get things done. Does building a entrepreneurial ecosystem really work? Well, I can tell you this: Among "technology-intensive" regions, according to my research, dealmaker-rich areas, like the Valley and Boston, always perform better than other metro areas. 

The lesson for experienced entrepreneurs? Sell out, by all means. But for the sake of your community, keep buying in.