This week Matt Cohen welcomes Anthony Lacavera, an entrepreneur known for founding Globalive and Wind Mobile.

Anthony shares his journey from starting his first business after graduating from the University of Toronto to challenging the Canadian telecom giants with Wind Mobile. He discusses the lessons learned from his successes and failures, his passion for innovation, and his latest ventures in the Caribbean telecom industry and the matchmaking space with Pair Us. Throughout the conversation, Anthony highlights the importance of resilience, transparency, and fostering meaningful relationships in both business and life.

About Anthony Lacavera

Anthony Lacavera is the Founder and Chairman of Globalive, a venture capital firm and operating company based in Toronto, Canada. Since establishing Globalive in 1998, Anthony has been involved in creating and leading several companies across industries like telecommunications, technology, and media. Among his notable ventures is WIND Mobile, a Canadian telecom company that was sold for $1.6 billion in 2015. Recently, Anthony co-founded Pairus, a platform combining traditional matchmaking with AI, and serves as Chairman of Paradise Mobile, a telecom initiative in Bermuda.

In addition to his entrepreneurial activities, Anthony has been active in media and technology. He founded Globalive Media in 2018, where he hosts "Beyond Innovation," a program that covers developments in technology and innovation. He also contributed to Bloomberg Television, focusing on technology, telecommunications, and entrepreneurship. Through Globalive Capital, Anthony has invested in over 200 early-stage companies and is involved in various mentorship programs supporting new entrepreneurs.

Anthony's career began after he earned a degree in Computer Engineering from the University of Toronto.

In this episode, we discuss:

(01:55) The founding of Globalive and its first big success with Wind Mobile

(04:11) Why transparency was the key to Wind Mobile's success

(06:10) The story behind trying to buy back Wind Mobile in 2022

(08:04) The challenges of foreign ownership restrictions in the Canadian telecom industry

(09:27) Re-entering the telecom business with Paradise Mobile in the Caribbean

(11:25) His biggest financial loss and what he learned from it

(12:50) The importance of self-awareness and learning from failure

(14:54) What Globalive looks for in startups: Founder resilience and self-awareness

(17:38) The importance of investing in your health and longevity as a founder

(20:00) Transforming the matchmaking industry with AI and human connections with Pair Us

(21:45) Why human connections are crucial for longevity and happiness

(26:45) How Anthony incorporates learning from every interaction into his daily life

(28:19) Why patience and long-term thinking are critical for entrepreneurial success

(31:16) The role of AI in transforming business

(36:45) Balancing giving advice with letting founders learn on their own

(38:04) Why taking care of your health is essential for sustained success

Fast Favorites:

📲 Favorite Tech Gadget: Samsung Z Fold6

📚 Favorite Book: The Science and Technology of Growing Young by Sergei Young

🤔 Favorite Life Lesson: Every single interaction you have with someone, think about what you can learn from that person, and journal it.

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