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INspired INsider Podcast


INspiredINsider Show with Dr. Jeremy Weisz features interviews with successful entrepreneurs, Ecommerce founders, & visionary leaders.

Leaders reveal deeply personal stories and explore the tough journey, big challenges, and mistakes that they overcame to achieve success.

You will find inspiring stories from: Founders of Atari, Baby Einstein, P90X, Einstein Bagels, Skymall, and many more.


Thank you for listening from your host of http://InspiredInsider.com Dr. Jeremy Weisz. Go to InspiredInsider.com for Full Video episodes. 

Mar 19, 2024

Greg Alexander is the Founder and Chief Investment Officer of Capital 54, where he decides which entrepreneurs to bet on and which firms to invest in. He supports entrepreneurs by helping them scale and exit their firms, and he does so by sharing how he scaled and exited his own.

Before opening Capital 54, Greg had two careers spanning 25 years. He co-founded professional service firm Sales Benchmark Index and served as CEO for 11 years. After scaling the firm, he successfully exited in 2017 by selling his interest. Before SBI, Greg was an executive at EMC Corporation, a leader in the data storage industry. He is the author of The Boutique: How To Start, Scale, And Sell A Professional Services Firm, among other books. Greg is also the Founder of Collective 54 and a Young Presidents’ Organization member.

In this episode…

Entrepreneurs aspire to build businesses they can sell for a profit in the long run. However, starting and scaling a profitable business can be a daunting task. In this regard, learning from experienced professionals who have successfully grown and exited their businesses is imperative.

Greg Alexander, a serial entrepreneur, was able to grow and sell his first boutique business for an impressive sum of $162 million. Despite facing numerous challenges in the journey, he overcame them with a winning combination of strong company culture, dependable team players, and an unwavering focus on the end goal. Today, he helps other founders achieve similar success by providing them with access to capital and creating a community where they can learn from his wealth of experience, make more money, work less, and ultimately achieve bigger and faster exits.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz chats with Greg Alexander, Founder of Collective 54, to discuss how he successfully grew and exited his business. Greg talks about the “F***up Fridays” culture strategy, the sales process exiting a brand and the lessons learned, how he leverages the community business model to scale Collective 54, and Capital 54’s investment criteria.