DiscoverThe Executive Connect PodcastSerial Entrepreneurship: Navigating the Risks and Rewards
Serial Entrepreneurship: Navigating the Risks and Rewards

Serial Entrepreneurship: Navigating the Risks and Rewards

Update: 2024-05-25



Welcome to the latest episode of the Executive Connect Podcast. Host Melissa Aarskaug spoke with Jeremy Lessaris, a seasoned entrepreneur with a diverse background in building and selling businesses across various industries. Jeremy shared the highs and lows of his journey, insights into the payments landscape, the impact of technology, and offered valuable tips for scaling and exiting businesses. Learn about the challenges and opportunities in today's entrepreneurial landscape and get practical advice on growing your business.


Key Takeaways:


00:00 - Introduction


05:30 - The Evolution of Payments Technology

·         The payments landscape has become increasingly seamless, allowing for quick and easy transactions.

·         Despite the convenience, small to medium-sized businesses often bear the brunt of high transaction fees, which can be predatory.

·         Machine learning can help small businesses negotiate better transaction rates.

·         The convenience of modern payment systems often hides the high costs for smaller companies.


09:03 - Impact of AI and Machine Learning

·         AI and machine learning are transforming various industries, including payments and customer interactions.

·         There's a growing value in handcrafted, human-interaction-focused businesses as a counterbalance to AI-dominated services.

·         AI's influence will likely increase, but human-centered crafts and services will see a resurgence.

·         The blend of technology and human touch can create unique opportunities for businesses.


19:33 - Strategies for Scaling Businesses

·         Focus on sales and revenue as the primary drivers for scaling.

·         Bootstrapping can lead to more disciplined and careful financial management.

·         Building a strong sales foundation is crucial before addressing other aspects of the business.

·         Bootstrapping helps entrepreneurs prioritize profitability and sustainability.


20: 36 - Mentorship and Networking

·         Having mentors and a strong network is invaluable for entrepreneurial success.

·         Mentors can provide guidance, support, and valuable insights that are crucial for growth.

·         Seek out mentors who can offer practical advice and support based on their experiences.

·         Building a network of supportive individuals can significantly impact your business journey.


27:35 - Balancing Work and Personal Life

·         Striving for a balance between work and personal life is essential for long-term success and well-being.

·         Entrepreneurs should build businesses that align with their desired lifestyle rather than compromising their personal lives.

·         Consider how business decisions impact your day-to-day life and overall happiness.

·         Aim for business models that support a healthy work-life balance to avoid burnout.

·         By focusing on these key takeaways, listeners can gain a deeper understanding of the current entrepreneurial landscape, the importance of technological integration, and practical strategies for achieving business growth and personal fulfillment.


Guest Bio:

Jeremy is a serial entrepreneur, investor, and former global marketing & communications executive. Over the past two decades Jeremy has founded and led eight of his companies to successful exits. Jeremy is currently the Founder & CEO of Payment Brokers, a fintech company, focused on AI-enabled cost reductions.

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About Melissa Aarskaug:

I’m an energetic executive with 15+ years of experience steering companies to new heights of growth and scale. An engineer at heart (I started my career as an engineering manager on one of the world’s largest concrete bridges), I’ve become a trusted leader and business builder in the technology and cybersecurity space. 

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Serial Entrepreneurship: Navigating the Risks and Rewards

Serial Entrepreneurship: Navigating the Risks and Rewards

Melissa Aarskaug