Career Stories: “With Great Risk Comes Great Reward”

April 18, 2024


Career Stories: “With Great Risk Comes Great Reward”

A (Tech) Road Less Traveled with ISC's CEO Jeff Osborn

by Elizabeth Drolet


"When you're a kid working with venture capitalists, everybody talks about taking their money and running to a tropical island…and nobody ever does. But I did," Jeff Osborn, president and CEO of Internet Systems Consortium (ISC), a leading developer of DNS (BIND) and DHCP open-source software, said.

"I was 37 years old. I took 15 years off, raced sailboats all over the Caribbean, and blew a king's ransom having way too much fun," he continued. 

Jeff has made many notable contributions to his over 35-year career in the commercial Internet industry. He is a serial entrepreneur and an angel investor. He has played several leadership roles in open-source software and hardware companies working in 3D printing, the most well-known being MakerBot Industries. He was featured in the Netflix documentary Print the Legend, which tells the history of the race to bring 3D printing to the forefront of society. 

When talking to Jeff, it's obvious a fire burns deep in his belly. His 6'2” stout frame and outgoing personality leave an impression. He oozes charisma and doesn't shy away from a challenge. U.S. President Thomas Jefferson said, "With great risk comes great reward," and Jeff's story is a testament to this.


Jeff attended a small liberal arts college in Hartford, CT, where he received a B.A. in Economics. Communications was his entry into the Internet. It was the mid-'80s and his second job out of college would land him in the trenches of the start of the public Internet revolution. 

The Dawn of the Public Internet Revolution

"We didn't know it back then. But we were working on one of the first four Internet nodes." 

It was a small startup based in Santa Barbara, CA.

"I was working with a company that made the OEM equipment for the Digital Equipment Corporation (DEC), and we made statistical multiplexers. Then, we came up with what is now known as a router. It was then an X.25 packet assembler/disassembler or PAD."

He then worked for another startup on the MIT university campus. 

"We were the 96th .com to be registered. Last I looked, there are currently 130 or 140 million .coms in the world, so we were really at the beginning of everything."

"I went into it and gave it all I had, failed, and lost everything"

Unfortunately, his first startup went bankrupt or, as Jeff describes it, "the start to any good story." Jeff also declared bankruptcy and lost everything. 

"I believed in the power of the Internet. I went into it and gave it all I had, failed, and lost everything. It took my house and my car. I drove from Massachusetts to Virginia in 1992 with a suitcase, a furious wife, a rusted-out Jeep, and two dogs, and that was it."

Friends and family warned Jeff about getting involved in a startup and placing his bets on this new thing called the Internet.

"Most people didn't believe in the future of the Internet. The advice was always to work for the phone company. Be smart. And then, I went through bankruptcy in April of '92, and three years later, I made $25,000,000. And suddenly, everybody's like, 'We always believed in you.'"


"Screw that noise"

A job opportunity opened at UUNET Technologies. Jeff ran the Sales, Service, and Installation Department. UUNET was the first commercial Internet service provider. 

It was also where Jeff struck gold. Over the years, Jeff had watched many of his twenty-something colleagues become multi-millionaires and then return to their 80-hour work week and spend their lives chained to their desks. 

A chance encounter while attending college at the tender age of 18 gave him the nerve to later say, "screw that noise." Jeff was leaving his dorm when he noticed a 55-year-old man in a suit waiting outside his neighbor's door. The man introduced himself as his neighbor's dad.

"We ended up talking some more, and I found out he was there visiting his son for the last time as he was in the fourth stage of lung cancer."

"What's even sadder is that he had worked his butt off all his life, rarely taking vacations or spending time with his kids." 

That's when a moment happened that changed his life. 

"The man bore his eyes into my soul and said, 'Don't be like me,' and that left a mark." 


"So I got — what has been the best job in a lifetime of great jobs" 

Jeff retired and launched a 42-foot carbon fiber catamaran into the Caribbean waters. The boat became a record breaker for overnight races from Fort Lauderdale to Key West and Miami to The Bahamas. 

"It was a tremendous amount of fun, but I eventually got bored." 

At this time, 3D printers were breaking out as the next big thing and had caught Jeff's attention. He put together a team of "kids" and began building 3D printers on a small scale, which then led to a much larger scale at Makerbot Industries. 

"And after Makerbot was sold, I went to many old friends and said, 'Back in the nineties, you guys were all trying to hire me, and I took 15 years off. Am I too late?'"

Jeff was right on time. 

Ten years ago, ISC was experiencing a significant revenue loss and needed a major reputation makeover. Jeff was told if he 'could fix it, he could run it.' Jeff rose to the challenge and ISC significantly improved. 

"So I got — what has been the best job in a lifetime of great jobs." 


The Secret to Good Business

According to Jeff, the secret to building great companies is valuing the people who work for you and investing in their quality of life.  

"I can assure you that everyone who works for me hears three things: I really appreciate your work. How can I help you? What can I do to make your life better?"

He added, "You almost always win by treating people well, and you almost always lose by letting most people affect how you feel. All you have to do is be kind. Although nobody takes it seriously, it's the root of every religion on earth."

Jeff lives by a golden rule of mutual respect. 

"It doesn't mean letting others treat you like a doormat, but it does mean treating people how you want to be treated. I'm not the smartest guy in technology, but I am great at understanding what people want and giving it to them."


Don't be Afraid to Get Called Crazy

Words he lives by are, "find where the conventional wisdom is wrong. Make sure you are right, and then bet everything against it."

And, of course, don't be afraid to be called a little crazy. 

"We can't imagine a world without the Internet. But from '84 to '94, we were the lunatics; don't be afraid to be crazy," he said. 

Jeff has been a member of NANOG since 2013 and represents our community's incredible professionals. Are you interested in serving as a mentor or being mentored by the tech leaders in our community? Join our mentorship program. Find out more here.



Elizabeth Drolet

Elizabeth Drolet is NANOG's Multimedia Story Producer

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