They were all started by entrepreneurs in their second (or third) act:
For starters, the second time around, you can bring all of your knowledge, contacts, and capital to a new idea, but I also think there are subtler factors that often make second acts more successful than the first:
1. You’ll feel less pressure.
When you are scraping tooth and nail to make something of your first business, every decision feels like do or die. Like a 16-year-old driving on the highway for the first time, new entrepreneurs tend to be a little heavy on the wheel, blowing every small problem into a life-threatening emergency (I know I did). In a second act, entrepreneurs mellow a bit and have a steadier hand at the wheel. Once a business owner has become financially independent, the pressure to succeed to feed your family is off.
2. You’ll be a better leader.
Being a bit mellower, entrepreneurs in their second acts often are better bosses. They tend to be a little more willing to give others credit and let juniors make mistakes — within reason — instead of micromanaging every detail. Like a parent who enjoys coaching his kids more than playing, the second-act business owner wants to succeed as part of a team, not just as an individual.
3. You’ll be motivated by a higher cause.
Once entrepreneurs are no longer motivated exclusively by making money, they are forced to find larger reasons for doing what they do — to start to think of how they can have a bigger impact on the world and make a difference. Being motivated by something other than money makes a founder much more likable as a leader and, therefore, better able to attract good people — loyal employees, partners and board members who want to contribute to a cause — to their mission.
So go ahead and build your first business — get the pressure, the mistakes, and a little bit of success out of the way. Then sell it and get to work on an even better second act.