Founding Partner 888vc | Building GRO8 | Venture Capitalist | Strategic Advisor | Fordham Alumni New York
50,000 customers begged Adobe not to kill boxed software. But, Shantanu Narayen did it anyway. That single decision turned Adobe from a $3B desktop software company into a $23B cloud empire. 📌 The recession that forced a rethink: 2008–09 exposed the flaws in the CD-based model like long release cycles, no recurring revenue, unpredictable cash flow. Narayen’s response? Disrupt Adobe before someone else did. 📌 The Creative Cloud gamble: He scrapped perpetual licenses and went all-in on subscriptions. The fallout were a $200M revenue dip, 50,000+ angry customers, and Wall Street’s skepticism. But he refused to blink, over-communicating the long-term vision until the market caught up. 📌 The payoff: • Revenue grew 7x under his leadership • Market cap increased nearly tenfold • 90%+ recurring revenue today Adobe became the playbook for legacy-to-cloud transformation copied by Microsoft, Autodesk, and more. 📌 The leadership philosophy: He leads by influence, not titles. He sets “unreasonable expectations” to stretch teams beyond comfort zones. And he treats failure as tuition, not shame. 📌 The current test: A failed $20B Figma acquisition. FTC lawsuits over subscriptions. Competitive pressure from Canva and AI-native design tools. Whether Narayen adapts again will decide his final chapter. But his call to kill Adobe’s old business model will remain one of the boldest CEO moves in tech. All in all, Shantanu Narayen proved this: the riskiest move is protecting the status quo. #Leadership #Transformation #CaseStudy #StartupLessons
Exectly!! Big risks, like changing Adobe’s old model, can lead to huge success. Great post!! ROHIT BAFNA
I love how Narayen treated failure as tuition, not shame. That mindset is what separates transformational leaders from the rest.
Yes lots of money for the company but as a customer I hate the high cost of software in the cloud now. It continues to charge forever and you never own anything. The cost have jumped astronomically compared to buying boxed software that you could use for a long time.
Shantanu’s move shows that real leadership isn’t about pleasing everyone — it’s about betting on the future when the present feels safe. Killing the status quo turned Adobe into a model for transformation and recurring growth. Sometimes the boldest risk is the one everyone hates at first.
One of the greatest tech leaders in the history of mankind!
i like the “The leadership philosophy”: lead by influence, not titles. Set “unreasonable expectations” to stretch teams beyond comfort zones.
Yes, it takes a lot of guts to make such a bold decision. It easier to observe the outcome in hindsight but at the time that decision was taken it would not have been an easy one. I've been in Adobe during its 8 best years of growth and wholeheartedly acknowledge the influence Shantanu and his leadership had on the growth of the company and its employees.
Adobe’s journey shows that real growth often comes from disrupting yourself before the market forces you to ROHIT BAFNA!
Senior Solutions Architect, Working on integration of Streaming Data, Streaming Analytics, Traditional AI and Generative AI
5dNo lessons just pure bragging. I can proudly say Once I had lunch with Shantanu with him sitting right next to me on the same table. He just became the CEO. That time Adobe share was at around 40 USD. I have seen it touching 10 times of that after this licensing change.