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From corporate conferences to startup workshops, Jimmy’s talks are practical, motivational, down to earth and unforgettable.
Speaking Topics:
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From Microsoft to Startup Founder: The Truth About Leaving a Corporate Career
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Building a Social Impact Business: How to Profit & Create Change
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How to Drive Corporate Innovation & Think Like a Startup
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Is Capitalism Broken? Rethinking Profit, Purpose & the Future of Business
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Jimmy speaks on a variety of topics around entrepreneurship, innovation, and the future of work. Popular talks include:
From Microsoft to Startup Founder: The Truth About Leaving a Corporate Career
Leaving a high-paying, secure corporate job to start a business isn’t just risky it’s terrifying. Jimmy knows because he did it. In this raw, honest, and humorous talk, he shares the truth behind leaving the corporate world, the biggest mistakes he made, and how he rebuilt his career as an entrepreneur.
Key Takeaways:
✔️ Why most people quit their job for the wrong reasons
✔️ The reality of entrepreneurship vs. the dream
✔️ How to transition from corporate leader to founder without going broke
Perfect for: Corporate professionals considering entrepreneurship, career changers, and startup founders.
Building a Social Impact Business: How to Profit & Create Change
Is it possible to make real money and real impact at the same time? Absolutely—but most businesses get it wrong. Whether you're launching a startup or leading a corporate initiative, this talk explores how to build a purpose-driven business that thrives financially while solving real-world problems.
Key Takeaways:
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Why “doing good” is a competitive advantage in today’s economy
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The 3 biggest myths about social impact businesses
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How to attract investors, customers, and talent by embedding impact into your model
Ideal for: Entrepreneurs, investors, accelerators, and corporations looking to integrate sustainability and social impact into their strategy.
How to Drive Corporate Innovation & Think Like a Startup
Big companies want to think like startups, but most fail. Bureaucracy, risk aversion, and short-term thinking kill innovation before it starts. Jimmy shares lessons from leading innovation teams at Microsoft and advising corporate leaders on how to create fast-moving, entrepreneur-driven cultures that actually produce results.
Key Takeaways:
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Why most corporate innovation fails (and how to fix it)
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How to build internal startup teams that move at speed
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The “intrapreneur mindset” how employees can innovate within large companies
Perfect for: Corporate executives, leadership teams, and innovation hubs inside major organizations.
Is Capitalism Broken? Rethinking Profit, Purpose & the Future of Business
The old model of capitalism growth at any cost is dying. But what comes next? In this provocative talk, Jimmy challenges business leaders, investors, and policymakers to rethink the role of business in society and explore how companies can be both highly profitable and deeply purpose-driven.
Key Takeaways:
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The flaws in traditional capitalism (and what’s replacing it)
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How businesses can create financial and social value at the same time
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The rise of impact-driven startups and responsible investing
Ideal for: Corporations, investors, policymakers, and anyone rethinking the future of business.
Why Book Jimmy Cockerton?
Organisers from corporations, universities, and startup accelerators have all trusted Jimmy to inspire their audiences. Here’s why he’s a sought-after speaker:
Proven Corporate & Startup Experience
Jimmy served as Microsoft’s Head of Impact, where he spoke to and led large teams in a Fortune 50 company. He’s also the founder of two startups and an active venture investor. This unique blend of corporate savvy and startup grit means he connects with audiences from both worlds and shares insights that resonate deeply.
Engaging Storyteller
As a speaker, Jimmy is known for his engaging, conversational style. He doesn’t just lecture – he tells stories, asks questions, and gets the audience involved. Expect plenty of real-life examples, a dash of humor, and an inclusive atmosphere where everyone feels inspired to participate.
Actionable Takeaways
Audiences leave Jimmy’s talks motivated and equipped to take action. Whether it’s a new framework for validating ideas or a mindset shift about failure, Jimmy ensures every attendee gains something tangible to apply in their own career or business.
Book Jimmy Cockerton for Your Event
Ready to inspire and empower your audience? To inquire about booking Jimmy for a speaking engagement, simply fill out the inquiry form below. Let us know about your event and what you’re looking for, and our team will get back to you promptly with details and availability.