When Kass Lazerow’s first e-commerce venture collapsed into bankruptcy, the financial loss was only the beginning of her troubles. The 54-year-old entrepreneur watched relationships shatter as friends and family who’d invested in her business saw their money disappear—and in one particularly painful case, a relative actually sued her.
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Yet from this devastating failure emerged one of tech’s most remarkable comeback stories. The same couple who faced financial ruin and personal betrayal would eventually sell their second company for a staggering $745 million, proving that entrepreneurial resilience can overcome even the most crushing setbacks.
The Devastating Collapse of Golf.com
In August 2000, just two months after the Lazerows’ golf score tracking platform Golf.com was acquired by e-commerce retailer Chipshot, Mike Lazerow received the phone call every entrepreneur dreads. The Chipshot CEO informed him the company was headed toward bankruptcy, rendering the 3 million shares of stock they’d received in the acquisition completely worthless.
“It sucked,” Kass recalls. “We had to look our investors in the eye and say, ‘we basically failed.’” The situation was particularly painful because their first $1 million in funding had come primarily from family members and friends, many of whom didn’t understand the high-risk nature of e-commerce startup investments.
Personal Relationships Shattered by Business Failure
The financial collapse triggered a cascade of personal consequences that far exceeded the monetary loss. “We definitely lost friends,” Kass states bluntly. The awkward conversations explaining why she couldn’t simply return the money to family members created rifts that never healed.
Most painfully, one family member actually filed a lawsuit against the couple. This legal action from within their own family underscored how deeply the business failure had damaged personal relationships, turning what should have been supportive connections into adversarial ones.
The experience taught them harsh lessons about mixing business with personal relationships, particularly in the volatile world of retail and technology startups where even promising ventures can collapse unexpectedly.
The Remarkable Turnaround and $24 Million Recovery
In a move that demonstrated both courage and belief in their original vision, the Lazerows bought back their company for $500,000 that same August. Over the next six years, they rebuilt the business focused on golf content and technology, ultimately selling it to Time Inc. for $24 million.
While many of their initial investors were too burned by the first failure to reinvest, those who did participate in the second round saw complete recovery of their original investments plus substantial returns. This redemption arc proved crucial in restoring some of the damaged relationships and professional credibility.
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Building Buddy Media Into a $745 Million Exit
With their next venture, Buddy Media, the Lazerows applied the hard-won lessons from their first failure. They secured financing exclusively from professional venture capital firms that specialized in startup investments, avoiding the personal complications of friends-and-family funding entirely.
The strategy paid off spectacularly when Salesforce acquired Buddy Media in 2012 for $745 million. This massive exit validated their persistence and demonstrated how proper funding structures can support growth without jeopardizing personal relationships.
Critical Lessons for Entrepreneurs Raising Capital
Kass now offers blunt advice to other founders based on her painful experience: “Have accredited investors who wouldn’t mind losing the money.” This approach ensures that financial backers understand the risks inherent in startup investing and won’t face personal hardship if the business fails.
The distinction between professional investors and personal connections became the cornerstone of their future funding strategy. Professional investors, including the chief executive officer of venture firms, typically approach investments with clear-eyed risk assessment rather than emotional attachments.
Broader Implications for Startup Culture and Funding
The Lazerows’ story highlights critical issues in entrepreneurship and investment culture. As other business sectors face their own challenges—from emerging technology concerns to healthcare policy impacts—the fundamentals of appropriate funding sources remain constant.
Similarly, just as businesses must navigate cybersecurity threats and adapt to technology platform changes, entrepreneurs must structure their financial foundations to withstand potential collapse. Even in sectors experiencing rapid growth like renewable energy, proper investor selection remains crucial.
From Personal Failure to Professional Triumph
Kass Lazerow’s journey from business failure and personal betrayal to nine-figure success represents one of entrepreneurship’s most powerful narratives. The experience of bankruptcy, while devastating, ultimately provided the foundation for their future achievements.
Her story serves as both cautionary tale and inspiration—demonstrating that even the most crushing professional setbacks can become stepping stones to extraordinary success when approached with resilience, learned wisdom, and strategic changes to business practices.
The transformation from being sued by family to selling a company for nearly three-quarters of a billion dollars stands as testament to what entrepreneurs can achieve when they learn from failure rather than being defined by it.
