S 02 | Ep 4 How to Build , Exit , and Build Again : Shane Neman ’ s Formula for Growth Shane Neman is a serial entrepreneur , venture capitalist , and real estate developer who built two bootstrapped businesses from scratch , exiting both profitably . After dropping out of NYU Medical School , he founded JuneBug , a full - stack operating system for the nightlife industry that predated most of the tools venues now take for granted . That business eventually revealed the opportunity behind his second company , EasyTexting , which became the largest business SMS platform in the United States before he exited that as well . In this episode , Shane discusses how each venture grew out of a problem he watched someone struggle with firsthand , and why that pattern continues to drive his investment decisions today . He talks candidly about what it took to sell software to nightclub owners in 2001 , including taking meetings at 3 in the morning and accepting cash payments , and how becoming the incumbent in a niche nobody else wanted eventually gave him the leverage to set his own terms . He also unpacks his barbell investment strategy , placing bets on deep tech categories like AI , quantum , and robotics on one end , and on physical assets he believes are essentially disruption - proof on the other . That thinking led him to acquire the operations of the Santa Monica Pier , which he describes as a forever asset in one of the country ' s top tourist markets .