EP46 | James Windon - From Lawyer to Billion-Dollar Founder: The Mindset of a Serial Entrepreneur episode artwork

EPISODE · Jul 11, 2025 · 1H 33M

EP46 | James Windon - From Lawyer to Billion-Dollar Founder: The Mindset of a Serial Entrepreneur

from The Dynamic Podcast · host Brendon and Rianon

In this powerful episode of The Evolv Podcast, we sit down with James Windon—serial entrepreneur, former lawyer, and co-founder of Flare HR, which sold for over $1 billion.James unpacks the mindset that took him from corporate law to building one of Australia’s most successful tech ventures. We dive deep into what it really takes to start a business—from choosing the right co-founder, to navigating self-doubt, to staying grounded through rapid growth.This isn’t just a highlight reel of success. James opens up about the hard lessons learned across multiple ventures, how identity shifts when you go from employee to founder, and why discipline, adaptability, and self-awareness are non-negotiable for high performers.Whether you're launching your first business, scaling your tenth, or simply trying to level up your mindset—this episode is a goldmine of insights from someone who’s walked the path.👉 Tap here to learn more or get started: dynamicrecov.com.au/offerYou can find him on socials:LinkedIn: linkedin.com/in/jameswindonGet in touch:Email: ⁠[email protected]⁠Instagram: ⁠@evolv_podcast⁠YouTube: ⁠The Evolv Podcast⁠TikTok: ⁠@evolv_podcast⁠Listen on Spotify: ⁠The Evolv Podcast⁠Listen on Apple Music: The Evolv Podcast

In this powerful episode of The Evolv Podcast, we sit down with James Windon—serial entrepreneur, former lawyer, and co-founder of Flare HR, which sold for over $1 billion.James unpacks the mindset that took him from corporate law to building one of Australia’s most successful tech ventures. We dive deep into what it really takes to start a business—from choosing the right co-founder, to navigating self-doubt, to staying grounded through rapid growth.This isn’t just a highlight reel of success. James opens up about the hard lessons learned across multiple ventures, how identity shifts when you go from employee to founder, and why discipline, adaptability, and self-awareness are non-negotiable for high performers.Whether you're launching your first business, scaling your tenth, or simply trying to level up your mindset—this episode is a goldmine of insights from someone who’s walked the path.👉 Tap here to learn more or get started: dynamicrecov.com.au/offerYou can find him on socials:LinkedIn: linkedin.com/in/jameswindonGet in touch:Email: ⁠[email protected]⁠Instagram: ⁠@evolv_podcast⁠YouTube: ⁠The Evolv Podcast⁠TikTok: ⁠@evolv_podcast⁠Listen on Spotify: ⁠The Evolv Podcast⁠Listen on Apple Music: The Evolv Podcast

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EP46 | James Windon - From Lawyer to Billion-Dollar Founder: The Mindset of a Serial Entrepreneur

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This episode was published on July 11, 2025.

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In this powerful episode of The Evolv Podcast, we sit down with James Windon—serial entrepreneur, former lawyer, and co-founder of Flare HR, which sold for over $1 billion.James unpacks the mindset that took him from corporate law to building one of...

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