Steve Jobs Still Casts Long Shadow At Web Summit


As Published on http://techcrunch.com/2014/11/08/steve-jobs-still-casts-long-shadow-at-web-summit/ byRon Miller

I spent this past week in Dublin at Web Summit, and I couldn’t help but notice, we are still fascinated, dare I say obsessed with the late Apple co-founder Steve Jobs more than three years after his death. If you knew the man or even had a meeting with him back in the day, interviewers wanted to hear about it.

Heck, even TechCrunch got into it this week with a retrospective of never-before seen Jobs photographs. It seems if you had any connection to Jobs, you’re in demand. Take former Apple CEO John Sculley as an example. He was famously lured to Apple by Jobs in 1983, but the honeymoon was short-lived and Jobs left under a cloud of animosity in 1985 to start NeXT Computers. Sculley was a successful executive before he joined Apple. He left Apple profitable 11 years later, and he’s done quite a bit in the 20 years since he left the company, but you would never know it.

All anyone wants to hear about is what Steve was like, and his involvement in forcing Jobs out of the company (although he disputed just how that went down). Almost 30 years after the fact though, we’re still talking about it and dissecting the politics of the situation, and asking Sculley about what happened. He is famous by association and it’s a strange dynamic.

But it wasn’t just Sculley who got asked about Jobs, so did Drobox CEO Drew Houston who was asked about a single meeting he had with Jobs in 2009. This wasn’t the first time he talked about this. In fact, he gets asked about it all the time. Why? Because we want to hear stories about the man. For Houston, it was by all accounts a surreal experience where he met a hero who wanted to buy his company. But he wasn’t there to sell and it never went much further than that because as Houston pointed on stage at Web Summit this week, if you don’t want to sell your company, don’t take meetings about selling your company. It ended there, but five years later just because Houston had a conversation with the guy, we still want to hear about it.

In the closing session of Web Summit, U2 lead singer, Bono appeared on a panel with House of Cards producer Dana Brunetti and Eric Wahlforss, co-founder of SoundCloud. There was lots of industry talk of course, but moderator David Carr of the New York Times had to ask Bono about a meeting with Steve Jobs five years ago in France (millionaire’s talk) when he infamously told him iTunes looked like a spreadsheet. Bono was surprised that for a guy who was so concerned about design, that Jobs didn’t make iTunes prettier. To be honest, the look of iTunes in my view is the least of its problems, but once again he had a face-to-face with Jobs and the world wanted to hear about  it.

Jobs died over three years ago, but his influence on the technology industry will very likely go on for a long time to come, and if Web Summit was any indication, our desire to hear stories about a man who had so much impact on the industry will likely continue too.

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About Shailendra Nair

AI Generalist & Executive Tech Leader in Insurance & Benefits Tech. Driving growth, trust, and resilience from AIG to Marsh McLennan. I am an AI Generalist and Executive Technology Leader with a career dedicated to reimagining how insurance and benefits ecosystems work in a digital first world. My expertise spans Insurance & Benefits Tech, digital transformation, and cybersecurity, with a proven ability to turn technology into both a growth engine and a resilience enabler. I have worked with global leaders such as PepsiCo, Allianz, AIG, and Marsh McLennan, experiences that gave me a rare mix of perspectives across insurance carriers, broking, and benefits advisory. This combination allows me to design solutions that balance global standards, local compliance, and client expectations while driving measurable business value. My strength lies in full stack insurance technology leadership, covering Property & Casualty, Life, and Benefits. I bring hands-on expertise in infrastructure, cloud, security, and enterprise architecture, combined with data platforms, AI automation, and digital ecosystems. Having led across this spectrum, I can translate complex technology into practical outcomes that deliver trust, scale, and innovation. As an AI Generalist, I focus on impact: • Building automation first operations that scale efficiently. • Designing chatbots and intelligent assistants to empower employees and clients. • Deploying AI-driven QA frameworks to improve speed and accuracy. • Exploring agentic AI roles to support compliance and transformation. My philosophy is simple: technology should reduce friction, inspire confidence, and accelerate growth. I design platforms that enhance sales, revenue, and client stickiness, proving that tech can directly enable business outcomes. At the same time, I remain deeply client centric a solution enabler who thinks out of the box to solve real challenges and deliver measurable ROI. 🌍 What excites me most is reimagining benefits ecosystems for the future of work. Employees demand seamless digital first experiences, organizations need efficiency, and regulators require trust and security. My mission is to build ecosystems that are secure, resilient, innovative, and human focused.
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