This CEO’s $1 billion side hustle started with a $5k credit card bet

This CEO's $1 billion side hustle started with a $5k credit card bet - Professional coverage

According to CNBC, 44-year-old Steve Sonnenberg turned his side hustle into a billion-dollar company called Awardco, which just hit a $1 billion valuation after raising $165 million in May 2024. The employee rewards platform counts major clients like AT&T and Hertz, letting workers redeem points for millions of Amazon Business items. Sonnenberg started the company in 2011 after his previous business WholesaleMatch collapsed following an FTC lawsuit that froze his assets and forced him into bankruptcy. With four young kids and “nothing left,” he charged $5,000 to a credit card to buy the Awardco.com domain while working other jobs. His current success stems from what he calls his entrepreneurial “superpower” – the ability to just start without hesitation and pivot constantly through obstacles.

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The pivot power

Here’s the thing about Sonnenberg’s “superpower” – it’s not some magical talent or genius insight. It’s basically just starting and then being willing to change direction constantly. He went from a physical trophy store concept to wholesale corporate rewards before landing on the current Amazon-integrated model. And when Amazon initially rejected them? His wife manually ordered products for clients while he cold-called corporations anyway. That’s not glamorous startup lore – that’s grinding through rejection after rejection. But it worked: by 2015, Amazon invited them to partner officially.

From bankruptcy to billions

What’s really striking is the timing of his comeback. Most people would take years to recover from having their assets frozen and business destroyed by an FTC lawsuit. Sonnenberg? He started his next company immediately. “What does any crazy entrepreneur do? You always have another [idea] on deck,” he says. That mentality – treating failure as just a temporary setback rather than a final verdict – seems to be the real differentiator. He built Awardco while working freelance web design jobs and later at Qualtrics, proving you don’t need perfect conditions to start something meaningful.

The future of employee rewards

With their recent $165 million funding round and billion-dollar valuation, Awardco’s positioned to dominate the employee recognition space. The Amazon Business integration gives them a massive advantage – employees get access to millions of products rather than being limited to some corporate catalog of boring options. And honestly, in today’s remote work environment, digital rewards that people actually want could become table stakes for retention. The question is whether they can maintain that startup agility as they scale. Sonnenberg’s pivot-heavy approach suggests they might actually keep that flexibility.

The real lesson here

Look, we hear about “fail fast” all the time in startup culture. But Sonnenberg’s story shows it’s not just about failing – it’s about what you do immediately after. He didn’t take a break to “find himself” or write a post-mortem. He started building the next thing while dealing with bankruptcy and supporting four kids. That level of resilience, combined with the willingness to change direction constantly, seems to be the actual secret sauce. And maybe that’s the real takeaway for anyone thinking about starting something: perfection is the enemy of progress. Just start. Then figure it out as you go.

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