Avi Freedman’s startup has proven to be an important part of the technological infrastructure helping enterprise businesses run post COVID-19.
During our interview on the DealMakers podcast, he described how he fell into the world of computing, applying to startup accelerator Y Combinator, the pros and cons of bootstrapping your startup versus raising venture capital money, and the post coronavirus fundraising landscape.
Finding A Fascination For Computing
Avi Freedman was born and grew up in the middle-class suburbs of Philadelphia. It was the 1980s when you had Radio Shack instead of Microsoft and Apple Stores.
His mother was a lawyer and his father a doctor. Then his uncle who was a cardiologist and MIT grad gave Avi a book that changed everything.
It was a book called Instant Basic. He ended up going to his father’s hospital to spend nights hacking and programming. He was just eight or nine years old.
Freedman’s grandparents also owned a manufacturing company. He used his newfound love for technology to automate their business and upgrade from index cards.
He then replicated that experience for other businesses and would go to computer shows to buy parts and build machines himself.
Avi then went on to study at Temple University. He brought in his own machines and set up a public UNIX system for running multi-user games.
He had become addicted to the T1 line at school, but at the time he was graduating you still couldn’t pay for dial-up internet service at home. He ended up creating Philly’s first ISP.
Learning The Ropes Of Business
Avi was recruited to AboveNet to run engineering. They became the world’s third-largest web hosting company and went public.
At AboveNet, he learned about the frustrations and challenges of being a founder and the head of a company that is out to scale. He learned the tough balance of being in control enough to make things happen while avoiding micromanaging, which can strip all the benefits from making great hires and sabotage their potential contributions.
After AboveNet, he joined Akamai. A company at which he stayed with for another 10 years, and through another IPO.
At Akamai, he learned what it was like to go through a severe economic crash, as well as finding love for projects.
The company was raising hundreds of millions of dollars and growing fast when the bubble burst. Not only did more than half of their customers stop paying, they completely went out of business.
Still, Avi used this time to start hobby and side projects that became very successful. Including some of the first decentralized and distributed applications for the internet. One sold for millions of dollars.
Then before starting his own company, he did a stint with ServerCentral as CTO, working on cloud infrastructure.
Avi came up with the business idea for what would become his own company Kentik. He already had a company that could be a customer of it. He did a mock-up for it. Not only did people show interest, they already wanted to buy it, signaling great product-market fit.
He did the math and calculated that even a seven percent increase valuation would justify the dilution of joining a startup accelerator given his lack of network with investors and desire to build a high-growth SaaS company.
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