Jai Shekhawat founded Fieldglass, a cloud-based VMS platform, in 1999, grew it to be the largest vendor management software firm in the world, then sold it in 2014 for $1 billion. He's raised capital, launched, grown and sold a business. Today, as a board member, adviser and investor, he has a broad view of the entrepreneurial field as well as opportunities to advise those who haven't yet had his experience. There are two lessons he says he now likes to pass along.

"One of them was make sure you have prepared your landing spot well before you land," he says. "There will come a moment when the phone doesn't ring, there are no emails. It's going to feel really good for a few days because you get to breathe again. But then comes the issue of relevance — so now what are you? You’re no longer running this entity. Preparing the groundwork for that is very important."

In his case, he says he had been running the firm for so long that it was easy for him to say it's time to do something else with his life. He decided to think about his future in terms of a portfolio — what are the things he's always wanted to do and what's been neglected?

Many of his personal interests, he says, had been starved. What he recognized was that if he didn't close certain doors, then other doors would never open.

The second piece of advice he carries with him is because selling a business is usually a monetary event of significance, former owners can suddenly get contacted by people offering opportunities.

"And the advice I got was to do nothing for a year," he says. "Just sit on your hands, do nothing for a year, let everything settle down, and then get used to the idea of having some resources."

Shekhawat spoke on the Smart Business Dealmakers Podcast about the experience from soup to nuts — fundraising, growth, selling and life after.