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Bhaskar Sunkara helped build AppDynamics from a laptop on a couch to a $3.7 billion Cisco acquisition.
Bhaskar Sunkara was employee number one and founding CTO at AppDynamics. Over nearly a decade, he helped turn the company into a category-defining application performance monitoring platform before Cisco acquired it on the eve of its planned IPO. He is now CEO of Bicycle, where he is building AI analytics agents for revenue-critical business data.
This conversation centers on a hard shift in enterprise software: moving from systems that display information to systems that detect problems, explain causes, and take action. Bhaskar argues that dashboard-driven operations are dying because no team can manually monitor every product, region, supplier, conversion path, and technical dependency in real time.
He makes the same critique of chat-based analytics. Letting users ask questions in plain English improves access to data, but it still depends on someone asking the right question at the right time. Bicycle takes a different approach. Its agents monitor business signals such as bookings, checkout conversion, payment approvals, and orders, then work through a decision tree spanning technical, commercial, supplier, inventory, pricing, and external factors.
The discussion also breaks down how Bhaskar and the AppDynamics team created focus before scale. They narrowed the product to Java, sold to operations rather than developers, built specifically for production, and used production proofs of concept to establish trust. That confidence eventually led to a self-service product customers deployed in production without assistance.
Bhaskar also explains why Bicycle chose transactional industries including travel, retail, and payments, where delayed decisions directly translate into lost revenue. He walks through the company’s “DEAL” framework: detect, explain, act, and learn.
In Today’s Episode We Discuss:
00:01 Introducing Bhaskar Sunkara
00:24 From India to Silicon Valley
03:59 Lessons from Building AppDynamics
07:10 Why DevOps Remains a Fuzzy Concept
08:52 Selling to Operations Instead of Developers
10:20 Running Proofs of Concept in Production
12:21 Launching AppDynamics Lite as a Self-Service Product
14:23 Cisco’s $3.7 Billion AppDynamics Acquisition
16:34 Learning Enterprise Scale Inside Cisco
18:05 The Origin of Bicycle
19:42 Turning Business Signals Into Action
21:47 From Business IQ to Proactive Analytics
23:43 Moving from CTO to CEO
25:08 Bicycle’s Product Evolution
28:38 Choosing Travel, Retail, and Payments
31:21 Reducing Resolution Times Across 45,000 Locations
34:49 Why Dashboard-Driven Operations Are Dying
37:01 Why Companies Are Over-Indexing on Chat
40:03 Selling Analytics to Business and Data Teams
42:00 Building the Cursor for Analytics Teams
43:36 How AI Is Changing Product Development
46:23 Prototyping Products With Claude
47:27 Bicycle’s Long-Term Vision
50:01 Rapid-Fire Founder Lessons
53:23 The Most Overrated Startup Metric
Pull Quotes
“Dashboard operations driven by dashboards are kind of dying.”
“You have to get the revenue back on track. You’re losing money.”
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