illustration of a man pushing a giant rock up a mountain to represent chapter 12 of Greg Lindberg’s new book

Chapter 12: Greg Lindberg’s Early Business Failures

3 min readDec 12, 2022

In Chapter 12 of his autobiography about his time in prison, Lindberg speaks openly about the failure and challenges he experienced.

The book, titled 633 Days Inside: Lessons on Life and Leadership, is a tell-all recounting of his prison time, including all the gory details and some incredible insights into the benefits he’s taken from his time behind bars. It’s also a personal growth story that has a little something inspirational for everyone.

Lindberg writes, “Fail early and fail often. Failing late can be disastrous.”

Greg Lindberg’s Working-Class Upbringing

Greg Lindberg’s grandparents were plumbers and auto mechanics, and his parents taught him the importance of hard work and discipline.

Lindberg fondly recalls his grandfather’s ledger book, in which he recorded each penny of income and expense. He earned 8 cents an hour. His father, who never took a day off while Lindberg was growing up, also left a lasting impression on him.

Lindberg was the youngest of five children, and there wasn’t much in terms of treats and spoils. There was always food on the table and a roof over their head, though. Greg Lindberg learned early on that hard work and perseverance can help them overcome hardships or failure.

Entrepreneurial Beginnings

In Chapter 12, Lindberg sheds light on how he created and grew his business.

“I started a business in 1991 with $5,000. I was an undergrad at Yale at the time and saw an unmet need in the home care market for regulatory compliance information, and launched a home care newsletter.

“By 1998, my business consisted of 12 people working out of one room full of folding tables and computers. We were struggling to meet payroll and pay our printing bill. During the 1990s, we built products in the health care space and started looking at acquisitions.

“My first acquisition was for $17,000 in the travel ticketing space just before it was disintermediated. That first failed acquisition taught the group a lot about how not to acquire companies.”

Failure and Adversity

When Lindberg’s company faced adversity in 1998, he was able to overcome it. Over half of home care agencies’ customers left in less than six months because of changes in regulations. The company learned from this and figured out how to remain disciplined in cutting costs as revenues declined.

Later that year, Lindberg’s company faced an even more significant setback.

“My business almost died in 1998, and we were able to diversify our revenue streams and rebuild cash flow,” he writes. “By 2002, we were able to close a ‘stretch’ acquisition for $8 million, which gave us a foothold in the medical coding space.”

Onward and Upward

Despite these setbacks and others he details in 633 Days Inside, Lindberg continued an impressive growth trajectory. He also overcame a potentially life-threatening health crisis.

“In 2006, we acquired a health care business with $4.8 million in EBITDA [earnings before interest, taxes, depreciation, and amortization]. We put into place new management and implemented our core values using lessons from several prior turnarounds,” Lindberg writes.

“We then launched over a dozen product lines. Fourteen years later, that business has multiplied its customer base and has an EBITDA of more than $74 million.

“In 2007, we opened our first offshore office in Faridabad, India. It became a center for excellence in software development, finance, and leadership. It allowed us to buy companies under stress, cut costs, and invest in development at the same time. Today, we have more than 1,800 employees in India.

“In 2009, I survived a brain tumor. I was, fortunately, able to return to work within a few days after the successful surgery.”

Chapter 12: Greg Lindberg’s Early Business Failures

Greg Lindberg’s Working-Class Upbringing

Entrepreneurial Beginnings

Failure and Adversity

Onward and Upward

Related Articles

Written by Greg Lindberg