From Skype to Etsy: Leadership Lessons from Josh Silverman
An interactive timeline exploring the leadership lessons of Josh Silverman. Discover how his core principles were forged through the challenges and triumphs at Evite, Skype, American Express, and Etsy. This content is based on his speech at the 2025 Harvard Undergraduate Ventures-TECH Summer Program.
Leadership Timeline
Select a company to explore the key challenges, pivotal insights, and lasting lessons from that chapter of his career.
Career Philosophy: The 3-Year Sprint
Silverman advises against rigid, long-term plans. Instead, he uses a simple three-part framework to evaluate opportunities in 3-4 year "sprints."
Is it Impactful?
Can you do something you will be genuinely proud of? Does the work have meaning and a tangible outcome?
Will You Learn from Great People?
Will you be surrounded by smart people who will challenge you and from whom you can learn valuable skills?
Will It Create More Options?
After 3-4 years, will you have more opportunities and a more valuable skillset than when you started, not fewer?
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