The 11 E-books I Wish Existed When I Started LoginRadius (So I Wrote Them)

I founded LoginRadius in 2013. We crossed one billion users on the platform somewhere around 2021, and by then I had filled a personal notebook with the things I wish someone had told me at the start. The cybersecurity-founder playbook did not exist in 2013. The CIAM category did not exist. Identity-as-a-service was three vendors and a debate about whether it was a category at all.

So I had to learn most of it from making the mistake and writing down what the mistake had taught me. Eleven of those notebooks have now become e-books. They are the books I would have given my 2013 self.

Each one is a specific painful lesson, written from the inside out. Each is ungated, free to read in browser, and downloadable as a PDF at guptadeepak.com/ebooks/. I covered the un-gating decision in why I un-gated all my e-books in 2025.

1. The Cybersecurity Entrepreneur

The lesson behind it. In 2013, every founder book I picked up was either a Silicon Valley memoir written for a general audience or a B2B SaaS playbook that assumed your buyer was a marketing director. None of them prepared me for selling to a CISO at a regulated mid-market company who needed two compliance audits, an InfoSec questionnaire response, and a SOC 2 Type II before signing a $40,000 contract.

What it actually covers. The cybersecurity-vertical version of the founder playbook: the buyer's actual procurement process, how to position against incumbents whose moat is largely procedural inertia, how to handle the security-questionnaire avalanche, when to invest in compliance certifications, how to think about vertical SI partnerships, and the founder-CEO-as-trust-signal problem unique to security categories.

Who it is for. The technical founder of a cybersecurity startup somewhere between seed and series A.

2. CIAM Buyer's Handbook

The lesson behind it. When LoginRadius was selling its first hundred CIAM contracts, our buyers were learning the category in real time, often from us. We were doing the educational work that should have been spread across the industry, and we were paying for it in long sales cycles. A buyer who has read a vendor-neutral handbook before talking to vendors closes 40% faster than a buyer who is learning the category during the sales cycle.

What it covers. The actual CIAM evaluation framework: what to look for, what to discount, how to weight pricing models, integration complexity, vendor lock-in risk, regulatory fit, and migration paths. Vendor-neutral on purpose, with named examples of the categories of decision that go wrong.

Who it is for. Anyone running a CIAM evaluation, especially in an industry where the buyer is technical but not an identity specialist.

3. Passwordless and Passkeys: The Enterprise Guide

The lesson behind it. Every "death of the password" prediction since 2014 has been wrong about the timeline. We at LoginRadius shipped passwordless features into product roadmaps three times before the market was actually ready. The technology was correct; the ecosystem was not. The enterprise rollout playbook needs to start with the question "what kills the rollout" rather than "what enables it."

What it covers. The passwordless and passkeys deployment guide for enterprises, including the rollback scenarios, the help-desk training requirements, the fallback architectures, and the IAM-team conversations that actually determine whether the project ships.

Who it is for. The enterprise IAM lead who has a passwordless mandate and is trying to figure out whether the mandate is achievable in the timeline they were given.

4. Zero Trust Playbook for B2B SaaS

The lesson behind it. Zero trust as a buzzword became indistinguishable from zero trust as an architecture by about 2019. We saw RFPs that listed "must be zero-trust" as a requirement without specifying what the buyer actually meant. The playbook a B2B SaaS team needs is different from the one a CISO at a F500 needs, and most of the published zero-trust material assumed the latter audience.

What it covers. The B2B-SaaS-specific zero-trust playbook: the architectural decisions, the third-party-risk implications, the SaaS-to-SaaS data flow problem, and what zero trust does and does not mean when your entire business runs on someone else's infrastructure.

Who it is for. The B2B SaaS founder or platform engineer who has to answer zero-trust questions on enterprise security reviews.

5. B2B SaaS Security Playbook

The lesson behind it. Most of what we learned at LoginRadius about B2B SaaS security was learned from incidents and near-incidents that nobody wrote down publicly. The space was running on shared informal knowledge and luck. The playbook needed to be written.

What it covers. The full security-program checklist for a B2B SaaS company from seed through series C: what to build in-house versus buy, when to hire the first dedicated security engineer, the realistic SOC 2 and ISO 27001 timelines, the vendor management problem, and the incident response runbooks that actually get used.

Who it is for. The founding team or first security hire at any B2B SaaS company that has just gotten its first enterprise inbound.

6. IAM Career Playbook

The lesson behind it. The best IAM engineers I ever hired at LoginRadius came from non-traditional backgrounds. They were former web developers, former system administrators, former QA engineers who had picked up identity along the way. There was no career path documentation for them, no clear sense of what to learn next or what the career ladder looked like.

What it covers. The IAM career path from associate to staff to architect to CISO, with specific skills, certifications, and project portfolios needed at each transition, and the lateral moves (consulting, product management, founding) that the playbook supports.

Who it is for. The mid-career engineer who has accidentally become the identity expert at their company and is wondering what comes next.

7. Breaking Into Cybersecurity

The lesson behind it. The early-career version of the IAM playbook. The cybersecurity hiring market is structurally biased against the people who would be best at the work: career-switchers, self-taught engineers, people without four-year computer science degrees. We hired them anyway at LoginRadius and they were consistently among the strongest contributors. The playbook documents how to get past the gatekeeping.

What it covers. The actual early-career cybersecurity entry paths in 2026: which certifications are worth doing, which are signaling theatre, how to position non-traditional experience on a resume, how to interview for technical security roles without a CS degree, and the specific subfields that hire most aggressively from non-traditional backgrounds.

Who it is for. The career switcher trying to break into cybersecurity in 2026, especially without a CS degree.

8. Cybersecurity Breaches Decoded

The lesson behind it. Every major breach in the last decade has been blamed on a different proximate cause and the same underlying causes: weak access management, poor secret hygiene, third-party trust failures, and detection gaps. Engineers who learn the underlying causes get better; engineers who only read the breach summary do not. The book exists because the public coverage of breaches is consistently bad at explaining what actually happened at the technical layer.

What it covers. Case studies of the most consequential breaches of the last decade, with the actual technical root cause, the missed detections, the recovery path, and the lessons that generalise.

Who it is for. The security engineer who wants to learn from the field's most expensive mistakes.

9. AI Agents: The Security Nightmare

The lesson behind it. Agentic AI is rebuilding the identity-and-access surface from scratch, and the existing security frameworks do not handle it. We are watching the same mistakes that the early SaaS era made with OAuth and SAML being repeated in 2026 with agent permissions, tool-use authorisation, and machine-to-machine identity.

What it covers. The threat model for agentic AI in production, the specific failure modes (prompt injection, data exfiltration through tool use, multi-step privilege escalation), the authorisation patterns that actually work, and the operational practices for running agents in regulated environments.

Who it is for. Anyone shipping agentic AI to enterprise customers, especially in regulated industries.

10. AI Search Visibility Guide

The lesson behind it. The cybersecurity vendors that own the next decade will be the ones who get cited by ChatGPT, Claude, and Perplexity when a buyer asks for the best vendor in a category. The path from being a Google-ranked vendor to being an AI-cited vendor is not obvious, and most published GEO guides are written for general B2B SaaS, not for security.

What it covers. The full AI search visibility playbook: how to instrument the measurement, what to publish, what to structure, what to schema-mark-up, how to monitor citation share, and how to recover when a competitor pulls ahead in the AI shortlist.

Who it is for. The marketing or growth lead at a B2B SaaS company that has noticed AI traffic is starting to matter and does not have a playbook for it.

11. Solo Founder AI Playbook

The lesson behind it. The leverage available to a solo or two-person founder in 2026 is roughly 10x what it was in 2013 when I started LoginRadius. The AI tooling stack is real and it is changing the calculation on what is fundable, what is buildable, and what is shippable. The playbook for using it without becoming a vibe-coded mess is genuinely different from the playbook for using it as augmentation on a 50-person engineering team.

What it covers. The solo-founder workflow for using AI as a force multiplier: which tools, which guardrails, which tasks to delegate, which tasks not to delegate, how to maintain quality as the codebase grows, and how to think about the technical debt that AI tooling produces.

Who it is for. The solo founder, indie hacker, or two-person team who is trying to build a serious product in 2026.

The twelfth e-book

I have a working draft titled "The Cybersecurity CEO's First 100 Days," which is the operating manual I wish I had when LoginRadius hit the transition from founder-led to professionally-managed. It is the hardest one to write because most of the lessons are about the parts of the job that founder memoirs systematically sanitize.

If there is a twelfth e-book that you wish existed, the suggestion box is open. The honest test for whether to write one is whether I would have paid serious money to read it in 2013. The eleven above all pass that test. The ones I have not written yet are the ones I am still figuring out.

Adjacent reading: bootstrapping growth for B2B SaaS startups and a decade of building a password company cover the LoginRadius journey in long-form essay format.