From Side Gig to Billion-Dollar Success: The Pivot Power

USAFri Nov 21 2025
Starting a business from scratch is tough, but turning a side hustle into a billion-dollar company? That's next-level. Steve Sonnenberg, the CEO of Awardco, did just that. His secret? He's not afraid to take risks or face setbacks. In fact, he sees them as part of the journey. "Starting is my superpower, " he says. "I just pivot fast when things don't go as planned. " Awardco, now worth $1 billion, began as a side project after Sonnenberg's previous company, WholesaleMatch, faced legal trouble. With his assets frozen and his business closed, Sonnenberg was left with nothing. But he didn't let that stop him. He used a credit card to buy the domain for Awardco and started building it on the side while working other jobs. The road wasn't smooth. Amazon initially rejected Awardco, but Sonnenberg didn't give up. He kept pushing, signing up corporate clients and even manually ordering products on Amazon for his employees. His persistence paid off when Amazon finally partnered with Awardco in 2015, automating the ordering process. Sonnenberg's background in the awards industry gave him an edge. He knew the space was outdated and ripe for disruption. "I was 100% confident we were going to find success, " he says. But he also admits to being a bit naive, a trait he believes many successful entrepreneurs share. Building a successful business after a major failure takes resilience and confidence. Sonnenberg's story shows that it's not about instant success, but about learning from failures and keeping going. As he puts it, "Start, then pivot, pivot, pivot, pivot. That's the story of Awardco. "
https://localnews.ai/article/from-side-gig-to-billion-dollar-success-the-pivot-power-4b5b1966

questions

    When Steve Sonnenberg's wife was manually ordering products on Amazon for Awardco's employees, did she ever consider starting her own side hustle?
    How did the legal and financial challenges from WholesaleMatch shape Steve Sonnenberg's approach to risk management in Awardco?
    If Awardco's initial idea was a physical store selling trophies, does that mean Steve Sonnenberg was literally awarding himself trophies for his entrepreneurial spirit?

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