The CTO Show with Mehmet Gonullu

In this episode of The CTO Show with Mehmet, I’m joined by Ahikam Kaufman, Co-Founder and CEO of Safebooks.ai, a seasoned finance executive turned entrepreneur with deep experience across startups, public companies, and large-scale acquisitions.We explore why finance has lagged behind other functions in digital transformation, how AI is fundamentally reshaping financial governance, and why the modern CFO is becoming a transformation leader, not just a financial steward.This conversation goes beyond buzzwords and dives into real-world problems: broken audit trails, fragmented systems, compliance risk, and how AI agents can finally deliver real-time financial truth.⸻👤 About the GuestAhikam Kaufman is the Co-Founder and CEO of Safebooks.ai.He began his career in accounting, served as a CFO in Silicon Valley startups, experienced multiple acquisitions including by Hewlett-Packard and Intuit, and spent over a decade as an entrepreneur.Today, Ahikam is focused on modernizing the Office of the CFO by applying AI to financial data governance, auditability, and compliance at scale.https://www.linkedin.com/in/ahikam-kaufman-688310/⸻🎯 Key Topics Covered • Why finance was never designed for today’s data complexity • The two biggest blind spots in modern financial organizations • What “audit trail” really means and why it’s so hard to achieve • How AI agents bridge structured system data and unstructured documents • From quote to cash: tracing transactions across fragmented systems • Why compliance failures are often data problems, not intent problems • The evolving role of the CFO in the AI era • Where humans still matter and where machines outperform • Why AI makes regulation easier to meet, not harder • Practical advice for founders building in finance and compliance⸻🧠 Key Takeaways • Finance teams deal with massive data but are not trained as data teams • Fragmented systems create hidden compliance and cash-flow risks • AI can monitor 100% of financial transactions, not just samples • Real-time governance is now technically possible for the first time • CFOs are becoming transformation leaders, not just scorekeepers • The future of finance is continuous, automated, and exception-driven⸻🎓 What You’ll Learn • How AI changes financial accuracy from “material” to near-perfect • Why most financial errors happen even when teams do “everything right” • How AI reduces headcount pressure without removing human oversight • What founders must understand before building in fintech or compliance • How finance can finally get its own “single pane of glass”⸻⏱️ Episode Highlights (Timestamps) • 00:00 – Ahikam’s journey from CFO to AI founder • 05:00 – The two unsolved problems in corporate finance • 09:30 – Why audit trails break across modern systems • 14:00 – What really goes wrong when financial data is wrong • 18:30 – How AI understands contracts and financial documents • 24:00 – Humans vs machines in financial decision-making • 30:00 – The CFO’s evolving role in AI transformation • 36:00 – Regulation, compliance, and AI realities • 43:00 – Advice for founders building in finance⸻🔗 Resources Mentioned • Safebooks.ai • Topics: AI agents, financial audit trails, CFO transformation, data governance

In this episode of The CTO Show with Mehmet, I sit down with Khaled Nazif, COO of DSquares, one of the most influential yet quietly powerful enterprise loyalty platforms in the MENA region.Khaled shares his journey from Stanford and Silicon Valley back to the region, where he helped scale DSquares into a 150M+ end-user platform serving banks, telcos, governments, and large enterprises across 16 countries.We go deep into what loyalty really means today, why most companies still misunderstand it, how culture breaks at scale if you are not intentional, and what founders in emerging markets can learn from Silicon Valley without copying it blindly.This is a conversation about scale, systems, leadership, and long-term thinking.⸻👤 About the GuestKhaled Nazif is the Chief Operating Officer at DSquares, a leading white-labeled loyalty and engagement platform powering some of the largest enterprises and government programs across MENA and Africa.Before returning to the region, Khaled spent nearly a decade in Silicon Valley, earning his MBA from Stanford, founding a B2B SaaS startup, and later working at Zendesk. He brings a rare blend of operator discipline, startup grit, and enterprise execution to scaling regional platforms.https://www.linkedin.com/in/khalednazif/⸻🧠 Key Takeaways • Why loyalty is misunderstood and often wrongly treated as a cost center • How DSquares scaled without VC hype and stayed bootstrapped for 13 years • What it really means to move from a “pirate” startup culture to a “navy” scale-up • Why government loyalty programs are not an oxymoron • The importance of productization when scaling enterprise platforms • How culture breaks after ~150 people and what leaders must do proactively • What MENA founders can learn from Silicon Valley and what they should ignore • Why failure must be normalized for ecosystems to truly mature⸻🎯 What You Will Learn • How to scale enterprise platforms across multiple countries and cultures • How loyalty, data, and behavior change intersect at scale • Why leadership transitions matter more than founder heroics • How to think long-term when building in emerging markets • Why execution discipline beats hype cycles every time⸻⏱ Episode Highlights & Timestamps00:00 – Welcome and introduction02:00 – Khaled’s journey from Stanford to Silicon Valley05:30 – What DSquares really does and why most people don’t know it09:00 – Scaling loyalty across banks, telcos, and governments13:30 – Loyalty vs transactions: what most companies get wrong18:00 – Using data and gamification to influence behavior23:00 – Loyalty as a revenue driver, not a cost center27:30 – Bootstrapping DSquares and resisting VC pressure33:00 – Replacing a founder and scaling leadership responsibly38:30 – The 150-employee culture breaking point45:00 – Pirate vs Navy mindset and operational maturity51:00 – Silicon Valley lessons that actually work in MENA57:00 – Failure, risk-taking, and ecosystem maturity01:03:00 – Advice for founders building in emerging markets01:08:00 – Closing thoughts and where to connect with Khaled⸻🔗 Resources & Mentions • DSquares – Enterprise Loyalty & Engagement Platform : https://dsquares.com/ • Book referenced: Blitzscaling by Reid Hoffman

In this episode of The CTO Show with Mehmet, I’m joined by Alex Schlager, Founder and CEO of AIceberg, a company operating at the intersection of AI, cybersecurity, and explainability.We dive deep into why AI agents fundamentally change enterprise risk, how shadow AI is spreading across organizations, and why monitoring black-box models with other black boxes is a dangerous mistake.Alex explains how explainable machine learning can provide the observability, safety, and security enterprises desperately need as they adopt agentic AI at scale.⸻👤 About the GuestAlex Schlager is the Founder and CEO of AIceberg, a company focused on detection and response for AI-powered workflows, from LLM-based chatbots to complex multi-agent systems.AIceberg’s mission is to secure enterprise AI adoption using fully explainable machine learning models, avoiding black-box-on-black-box monitoring approaches. Alex has deep expertise in AI explainability, agentic systems, and enterprise AI risk management.https://www.linkedin.com/in/alexschlager/⸻🧠 Key Topics We Cover • Why AI agents create a new and expanding attack surface • The rise of shadow AI across business functions • Safety vs security in AI systems and why CISOs must now care about both • How agentic AI amplifies risk through autonomy and tool access • Explainable AI vs LLM-based guardrails • Observability challenges in agent-based workflows • Why traditional cybersecurity tools fall short in the AI era • Governance, risk, and compliance for AI driven systems • The future role of AI agents inside security teams⸻📌 Episode Highlights & Timestamps00:00 – Introduction and welcome01:05 – Alex Schlager’s background and the founding of AIceberg02:20 – Why AI-powered workflows need new security models03:45 – The danger of monitoring black boxes with black boxes05:10 – Shadow AI and the loss of enterprise visibility07:30 – Safety vs security in AI systems09:15 – Real-world AI risks: hallucinations, data leaks, toxic outputs12:40 – Why agentic AI massively expands the attack surface15:05 – Privilege, identity, and agents acting on behalf of users18:00 – How AIceberg provides observability and control21:30 – Securing APIs, tools, and agent execution paths24:10 – Data leakage, DLP, and public LLM usage27:20 – Governance challenges for CISOs and enterprises30:15 – AI adoption vs security trade-offs inside organizations33:40 – Why observability is the first step to AI security36:10 – The future of AI agents in cybersecurity teams40:30 – Final thoughts and where to learn more⸻🎯 What You’ll Learn • How AI agents differ from traditional software from a security perspective • Why explainability is becoming critical for AI governance • How enterprises can regain visibility over AI usage • What CISOs should prioritize as agentic AI adoption accelerates • Where AI security is heading in 2026 and beyond⸻🔗 Resources Mentioned • AIceberg: https://aiceberg.ai • AIceberg Podcast – How Hard Can It Be? https://howhardcanitbe.ai/

Raising capital looks easy from the outside. In reality, it is one of the most misunderstood parts of building a startup.In this episode, Mehmet sits down with Daniel Nikic, a global investment researcher who has analyzed over 15,000 companies across the US, Europe, and the Middle East. Together, they unpack the hard truths founders need to understand about fundraising, investor psychology, market geography, and why most rounds fail long before the first term sheet.This is a grounded, no-hype conversation about what actually drives investment decisions in 2025 and why “easy money” is often the biggest illusion founders believe.⸻About the GuestDaniel Nikic is the founder of Coherent Research and a global investment research professional with deep experience across North America, Europe, and emerging markets. Originally from Canada and now based in Croatia, Daniel has worked with investors, family offices, and founders worldwide, helping evaluate companies across stages, industries, and geographies.His work focuses on due diligence, market opportunity analysis, and understanding the human and cultural factors behind investment decisions.⸻Key Topics Discussed • Why most fundraising fails before it even starts • The biggest misconceptions founders have about “easy capital” • How geography actually impacts investment decisions • Why the Middle East is not fast money despite capital availability • Founder psychology, stress, and emotional control as investment signals • What investors look for beyond pitch decks and valuations • The difference between angels, VCs, family offices, and accelerators • Why urgency and FOMO often kill deals instead of closing them • How AI is changing investment behavior and decision-making • Realistic timelines for closing funding rounds in emerging markets⸻Key Takeaways • Capital is not free money. Investors expect returns, discipline, and execution. • Geography still matters, but trust and relevance matter more. • Founders who rush fundraising often lose credibility. • Investors back people they trust, not just ideas or decks. • Being organized and prepared beats hype every time. • Fundraising is a relationship-building process, not a transaction.⸻What You Will Learn • How to target the right investors at the right stage • Why mixing angels, VCs, and family offices too early backfires • How investors think about risk, timing, and founder maturity • What “smart money” really means beyond capital • How long fundraising realistically takes and why patience matters⸻Episode Highlights & Timestamps(You can fine-tune timestamps once audio is finalized) • 00:00 – Introduction and Daniel’s global background • 04:00 – Patterns from analyzing 15,000+ companies • 07:30 – Geography vs psychology in startup success • 10:45 – The Middle East investment misconception • 15:20 – Why capital follows trust, not hype • 18:30 – Choosing the right investor type early on • 22:40 – Check sizes, valuations, and regional differences • 27:00 – AI, FOMO, and modern investment behavior • 32:00 – Why urgency kills fundraising deals • 36:30 – Realistic timelines to close a round • 41:00 – Final advice for founders raising capital⸻Resources & Links • Daniel Nikic on LinkedIn: https://www.linkedin.com/in/daniel-nikic/ • Website: https://www.danielnikic.com/

In this episode, Gabriel Jarrosson, founder and managing partner at Lobster Capital, breaks down what truly drives breakout startups inside the world’s most competitive ecosystem.Before becoming a YC-focused investor, Gabriel built seven startups, failed four, and bootstrapped one to one million ARR alone — no co-founder, no employees, no AI.Today he invests exclusively in YC companies and shares how he evaluates founders, why early traction beats everything, how YC creates unstoppable momentum, and how AI is reshaping the next generation of builders.⸻About Gabriel JarrossonGabriel Jarrosson is a serial founder turned YC-specialized investor and managing partner at Lobster Capital. He has built seven companies, exited three, and invested in more than 100 YC startups. Gabriel also hosts The Lobster Talks and has grown a fast-rising media presence supporting early-stage founders.https://www.linkedin.com/in/gabrieljarrosson/⸻Key Takeaways • Why solo founders can still win big when they embrace urgency, automation, and creative resourcefulness • The mindset required to scale without waiting for funding or a co-founder • YC founder patterns: technical teams, relentless execution, and high velocity • Why YC attracts the world’s strongest builders and why it’s nearly impossible to replicate • Gabriel’s 2 percent rule for selecting the best companies in every YC batch • Why early revenue and market pull matter more than ideas and hype • How AI is changing the definition of what a “lean team” can achieve⸻What You Will Learn • How top investors evaluate teams, traction, and momentum • How YC creates an environment that rewires founders to move faster • Why some geographies struggle to reproduce Silicon Valley outcomes • How to think about automation, support systems, and scaling with AI • How founders outside the US can become YC-ready • What Gabriel regrets missing as an angel investor — and what he learned from it⸻Episode Highlights & Timestamps00:00 — Introduction01:30 — Seven startups, three exits, four failures03:00 — Bootstrapping to 1M ARR as a solo founder07:00 — The role of AI in scaling today10:00 — Why YC is a category of its own14:30 — What YC founders have in common18:00 — Why “local incubators” fail to replicate YC21:00 — How Gabriel selects winners27:00 — Getting into competitive YC deals33:00 — The media edge in venture37:00 — Becoming YC-ready as a non-US founder46:00 — Gabriel’s biggest miss50:00 — Closing thoughts⸻Resources Mentioned • Lobster Capital: https://www.lobstercap.com/ • The Lobster Talks podcast: https://www.youtube.com/@lobster-talks