Serial Entrepreneurship: Navigating the Risks and Rewards

Guest:Jeremy LessarisSerial Entrepreneur | Founder & CEO, Payment BrokersHost:Melissa AarskaugExecutive Connect | WebsiteYouTube: @ExecutiveConnectEpisode Overview:In this episode of Executive Connect, host Melissa Aarskaug speaks with Jeremy Lessaris, a seasoned serial entrepreneur who has built and sold eight companies across different industries. Jeremy dives into the realities of entrepreneurship—from the wins to the wipeouts—offering candid insights into the evolution of payments tech, the growing influence of AI, and the art of scaling a business sustainably. Whether you're in the early stages or planning your next exit, this episode offers practical guidance on staying ahead without burning out.Timestamps:00:00 – Introduction05:30 – The Evolution of Payments Technology09:03 – Impact of AI and Machine Learning19:33 – Strategies for Scaling Businesses20:36 – Mentorship and Networking27:35 – Balancing Work and Personal LifeConnect With Us:Podcast Website: https://www.executiveconnectpodcast.comYouTube: https://www.youtube.com/@ExecutiveConnectSocial:LinkedIn: https://www.linkedin.com/in/melissa-aarskaug/TikTok: https://www.tiktok.com/@melissa_aarskaugX: https://x.com/melissaaarskaug

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This is the Executive Connect Podcast - a show for the new generation of leaders. Join us as we discover unconventional leadership strategies not traditionally associated with executive roles. Our guests include upper-level C-Suite executives charting new ways to grow their organizations, successful entrepreneurs changing the way the world does business, and experts and thought leaders from fields outside of Corporate America that can bring new insights into leadership, prosperity, and personal growth - all while connecting on a human level. No one has all the answers - but by building a community of open-minded and engaged leaders we hope to give you the tools you need to help you find your own path to success.