He spent a good portion of his childhood and adolescence on the wrong path, joining a gang when he was just 13 and started getting into countless fights. As time passed, his exploits grew more brazen; in his effort to earn his own income and ease his family’s financial burden, he turned to peddling contraband goods such as duty-unpaid cigarettes and pirated VCDs. He was often on the run from the police, at times avoiding arrest by a hair’s breadth. After years of being a “straight-F student” in school, there came a point he decided to pick himself up and put effort into studying for his Singapore-Cambridge GCE O-Level examinations, eventually scoring remarkably well and exceeding the expectations of his teachers and peers. He went on to pursue a diploma in Biomedical Science, a course of study he was always interested in.
At the age of 19, while still studying for his diploma, he signed a bond with the Singapore Armed Forces to serve a regular military career after his study. Wynnberg thought he had been set on the right path in life, but his relief did not last long as he soon started making good money from his side hustles and picking up the undesirable habits of drinking and gambling—experiencing five- to six-figure daily swings in the casino at his peak. His attendance and grades at school plummeted, eventually resulting in his expulsion.
When Wynnberg enlisted shortly after, he had difficulty adjusting to the military lifestyle of strict discipline, a stark contrast from the freedom of the high life he was living just before. Unable to cope, he went AWOL, and was also charged with insubordination of his superiors. He was sentenced on two separate occasions, and spent a total of 12 months locked up in the detention barracks. Because of his poor performance, he was discharged from his regular service and had to repay close to $40,000 for breaking the bond he had signed.
After he had completed his national service, Wynnberg’s life had no lack of dramatic experiences: almost getting shot in a confrontation with four men in San Diego, spending a night locked up in a Thai police station for drunk driving, and surviving 2 skydiving crashes, amongst many others. Wynnberg wants to take all the lessons he has learnt from these experiences and share it with others. Fast forward to now, after having successfully pulled himself out of his self-acknowledged “degen phase,” Wynnberg knows the difficulty of getting one’s own life back in order and staying on the right course without distraction. For the past 5 years, he has been living with a newfound purpose to empower as many people as possible.
In 2015, Wynnberg embarked on a journey to build his legacy and leave a positive impact on the world by helping people excel in their business, life, and income. With his quintessential rags-to-riches success story of sacrifice, hard work, and perseverance, as well as the unique and charismatic way he communicates it, Wynnberg has inspired many audiences, appeared on TV, and been featured on news publications such as Forbes, USA Today, Yahoo! Finance, and many more.
2017 was an eventful year for Wynnberg. It was the year he obtained his United States Parachute Association (USPA) ‘A’ license and successfully completed more than 50 solo jumps. Just prior to that, he miraculously survived his second near-fatal skydiving accident, an experience that motivated him to publish his first book, Think Act Prosper, something which he had been putting off for years. The book turned into a business conference, and subsequently a magazine featuring the world’s best thought leaders and business experts such as Brian Tracy, Kerri Kasem, Evan Carmichael, Elena Cardone, David Meltzer, Kim Perell, and many more.
A strong believer of education, Wynnberg has been actively helping underprivileged children in the Southeast Asia region. In 2019, to embody his own beliefs, he decided to further his own education by pursuing an MBA degree at Murdoch University.