Sumit Siddharth, widely known as Sid, joins Vandana Verma to discuss the self-belief behind entrepreneurship, lessons from building and selling a security business, and his people-first approach to angel investing and mentoring.
Sid grew up in Lucknow and graduated from IIT Kanpur in materials science and engineering. Although his degree was not in computer science, access to IIT’s network and hacking competitions helped him discover the field he wanted to pursue.
He began his career at NII Consulting in Mumbai and later moved to the United Kingdom. In 2013 he founded NotSoSecure, which Claranet Group acquired in 2018. Sid exited two years later. In 2021 he started The SecOps Group and became involved with additional companies as a co-founder, investor, or mentor.
Connect with Sid on LinkedIn.
Sid decided while still in school that he would attend an IIT, despite having no family precedent for it. Publicly writing that goal on a notebook invited ridicule, but it also reflected a combination he now seeks in entrepreneurs: passion and self-belief.
IIT then provided a different lesson. Surrounded by students with exceptional ranks and academic habits, he quickly realized that copying another person’s strengths would not work. A very low early score forced him to understand his own capabilities and find another route. The experience combined discipline with adaptability: when preparation had been imperfect, the immediate task was still to solve the problem and get the job done.
Through his Disruptors initiative, Sid invites early-stage founders to approach him for investment and support. He distinguishes his approach from advice offered only in return for equity: when he believes in a company, he invests both money and time.
His first filter is the relationship with the founders. Financial models, product-market fit, and go-to-market plans matter, but an early investor will work closely with the people behind them. Sid prefers partnerships where both sides welcome difficult calls and enjoy solving problems together. His role is often to help turn an idea into a scalable business by clarifying its proposition, audience, marketing, constraints, and next strategic decision.
He avoids becoming the technical authority in companies whose founders know their domain better. Instead, he focuses on strategic questions: what makes the product distinct, whether the intended customer is correct, which bottleneck limits growth, and whether an introduction or unconventional marketing idea could help.
Running and advising several companies creates constant competition for attention. Sid does not claim to have achieved perfect balance. His practical method is compartmentalization: each company must be treated as an independent entity, and frustration in one should not spill into another.
That separation also prevents a struggling company from pulling every other venture down with it. Collaboration among portfolio businesses can be useful, but collective support should not become collective failure. Sid values the startup principle of failing fast because experience helps him recognize earlier when an approach is unlikely to work.
He describes the common thread across hacking, company building, and life as problem solving. Experience changes the scale and type of the problems, while efficiency comes from solving more difficult problems with greater clarity and less wasted time.
Research and entrepreneurship both begin in uncertainty. New ideas create exciting chaos, but eventually that material must be distilled into a proposition others can understand. Sid sees a mentor’s role as helping founders remove enough noise to think clearly, not taking control of the company.
His advice is to let an idea mature before quitting a job. Founders should ask why someone will buy, what happens when an assumption fails, whether the company can scale, and whether the likely outcome is a lifestyle business or something larger. Self-belief should be supported by validation rather than used as a substitute for it.
At the same time, he warns against waiting forever. Before launching his first business, someone reminded him that the worst plausible outcome was returning to penetration testing. Understanding a survivable downside gave him the confidence to try.
Sid also discusses The SecOps Group’s independent cybersecurity exams. They test practical ability in a setting closer to a real engagement, where practitioners can use tools and internet research. The initiative separates examination from training and keeps the focus on the technical skill being assessed.
