Best of Bootstrapping: Bootstrapped an AI Security Startup to $10M+

Osprey Security Founder Rohit Anabheri had effectively used the Bootstrapping Using Services technique to bootstrap an AI-Powered Enterprise Security venture to mid eight figure revenues when we spoke in 2023. In that process, he had turned down offers for venture capital.

Sramana Mitra: Let’s start by introducing our audience to yourself and then we’ll come to the Osprey Security journey in a moment. You are a serial entrepreneur, yes?

Rohit Anabheri: That is correct.

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Building an AI Platform Company for Real-Time Applications: Vantiq CEO Marty Sprinzen (Part 2)

Sramana Mitra: Okay. But standard VC route at the time was different from the standard VC route of today because the number of, the amount of money that VCs used to invest was much smaller. The VC fund sizes were much smaller. It was actually the way venture capital should have been.

The Accelerator Conundrum: Playbook for B-to-C Entrepreneurs

B-to-C startups are notoriously high-risk. The failure rate is brutal. The temptation to chase scale with venture funding is strong—and often fatal. Most accelerators feed this temptation. They want viral growth, app downloads, and DAUs—regardless of whether there’s a business model behind it.

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The Accelerator Conundrum: Playbook for Ecommerce Entrepreneurs

Ecommerce is seductive. It promises scale, global reach, and fast-moving consumer engagement. But here’s the truth most founders don’t hear in traditional accelerators: Ecommerce is brutal. It’s low-margin, logistics-heavy, and customer acquisition costs can eat you alive—unless you operate with ruthless discipline.

Building an AI Platform Company for Real-Time Applications: Vantiq CEO Marty Sprinzen (Part 1)

The world is severely short of AI talent to build complex solutions. It is essential that platforms offer layers of abstraction on top of which systems can be built without getting deep into the weeds. Vantiq is innovating with such a platform and offering excellent business model options including revenue sharing, outcome-based pricing, etc. Very cool company.

The Accelerator Conundrum: Playbook for Entrepreneurs Building 2-Sided Marketplaces

Two-sided marketplaces are deceptively complex. Founders often underestimate the difficulty of igniting both sides of the equation—supply and demand—simultaneously. Add to this the noise of accelerators pushing scale-before-substance, and you have a recipe for premature failure.

The Accelerator Conundrum: Playbook for Solo Entrepreneurs Bootstrapping an Ultralight Startup

You’re a solo founder with a big vision but limited resources. Smart. The conventional startup path isn’t built for you. An “ultralight startup” strategy focuses on extreme leanness, rapid validation, and achieving profitability with minimal overhead. It’s about building a sustainable business, on your terms, without needing a team or external capital initially.

The Accelerator Conundrum: Playbook for Founders Bootstrapping with Services

You’re a founder leveraging services to build your product. Smart move. This strategy provides immediate revenue, funds product development, and offers direct market validation – all without premature dilution. It’s about building a sustainable foundation, on your terms.