Vivek Ramachandran, founder of Pentester Academy and SquareX, joins Vandana Verma to trace his path from a curious young programmer to security researcher, educator, and repeat founder, while sharing how he structures leadership and protects long-term conviction.
Vivek’s interest in security began around 1999, after news of distributed denial-of-service attacks led him to find the Tribal Flood Network tool. Its C source code was beyond his knowledge at the time, so he began teaching himself programming. The idea that one person could build software with internet-wide impact captured his attention.
After IIT, he worked in low-level security engineering at companies including Cisco. A research opportunity at AirTight Networks led him to break a wireless cloaking technology and present the work at DEF CON in 2007. The experience showed him that his research could stand on a global stage.
He left salaried work to research from his parents’ home and created SecurityTube as a place to publish free lessons. Training organizations began inviting him to teach, and audience demand eventually led to paid courses, certifications, and the subscription platform Pentester Academy. After its acquisition, he founded SquareX to address browser-based endpoint security.
Pentester Academy did not begin with a business plan. Vivek wanted to document what he was learning and make it useful to others. That body of free material built trust with a global audience. When he released the first paid course in 2011, hundreds of people bought it so quickly that PayPal temporarily blocked the account as suspicious.
The episode reinforced a lasting principle: contribute to a community before expecting a commercial return. Pentester Academy’s early growth came from learners who already knew the quality of Vivek’s work. Subscription courses and cloud labs followed after the audience demonstrated a real need.
After exiting Pentester Academy, Vivek examined why end-user security remained weak. He believed browsers, laptops, and endpoints would remain central to productive work for at least the next decade because human limits constrain how much information can be used on smaller interfaces.
That long-lived problem became the basis for SquareX. Vivek initially funded research and the early team himself, then raised capital from Sequoia, whose team he already knew and respected. Despite prior success, he urges the new team to keep a beginner’s mindset rather than assume the previous company’s playbook guarantees another good outcome.
Vivek starts by reviewing what happened the previous day and where technical and go-to-market teams are blocked. He spends focused time with each group, while avoiding so many meetings that engineers lose the time needed to build.
Later in the day, he turns to strategy, future investors, potential angel participants, and recruiting exceptional people. The team regroups near the end of the workday for demonstrations or unresolved decisions. He summarizes the founder-CEO role as empowering others, making quick decisions, and then getting out of their way.
Entrepreneurship is difficult, and the team looks to the founder when plans fail. Vivek believes the leader must preserve realistic optimism because visible loss of hope spreads immediately. That expectation should not turn into treating people like machines. There may be occasional long days, but leaders should judge a person’s contribution over time and recognize illness, family obligations, and natural fluctuations in productivity.
Determination matters because advisers, investors, and the market will challenge the thesis. Feedback should be processed seriously, but the founder must still make the decision. Vivek recalls receiving dismissive comments about his Indian accent when he began selling education online; he chose to focus on the smaller group that valued the work.
He now limits prolonged, unproductive argument and invests his scarce time in people who add constructive energy. Healthy disagreement remains useful, but endless adversarial interaction can drain the focus needed to build.
Vivek expects a knowledge economy increasingly shaped by specialization. Rather than chase shortcuts, practitioners should choose an area that genuinely interests them and develop rare depth. He also sees an opportunity for more deep-technology cybersecurity companies to emerge from India, which already has the technical talent and a large security community.
