Alex Macdonald. A $300M Exit is No Reason to Retire
Feb 18, 2025
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In this conversation with Alex Macdonald, Founder of the $300M digital concierge company Velocity Black, he reveals his post-exit mindset. Rather than retiring, he dove into building SQL to avoid the existential crises many face after selling a business. Alex discusses the emotional toll of transitioning from entrepreneur to investor, the importance of community over individualism, and the significance of maintaining connections. He challenges conventional happiness, emphasizing that true fulfillment often springs from embracing struggle and cultivating kindness in leadership.
Entrepreneurs often find greater fulfillment in launching new ventures after a successful exit, avoiding the potential identity crisis that can arise.
The journey of Velocity Black exemplifies the importance of adaptability, as it pivoted from a mobile payment service to a successful digital concierge platform.
Prioritizing health and wellness is essential for entrepreneurs to enhance decision-making abilities and maintain resilience in a high-pressure environment.
Deep dives
The Role of Founders in Value Creation
The discussion highlights a prevalent belief that there's a surplus of capital available, yet a scarcity of talented individuals capable of creating valuable businesses. Founders who possess the tenacity and creativity to build and innovate are in high demand, as fulfillment often derives from the act of creation and value-building. The speaker emphasizes that many successful entrepreneurs find greater satisfaction in starting new ventures rather than taking extended breaks after an exit. This iterative process allows founders to apply lessons learned from past experiences, fueling their desire to build once more.
The Evolution of Velocity Black
The journey of Velocity Black serves as a case study in adaptability and innovation. Initially launched as a mobile payment service, the company had to pivot due to unsustainable economics, transforming into a successful digital concierge platform. This move was met with initial skepticism, as it predated the widespread adoption of artificial intelligence, yet ultimately proved to be fortuitous. Leveraging existing relationships and enhancing customer experiences became key factors in the business's growth, leading to significant revenue increases in a highly competitive market.
Transitioning Post-Exit
For many entrepreneurs, the transition after an exit can lead to an identity crisis, yet this speaker notes the importance of having a new venture to avoid stagnation. Engaging in a new business allows founders to channel their energies positively and provides a sense of purpose, preventing a descent into unproductive habits. The discussion reveals that for successful founders, continued involvement in building companies can enhance their fulfillment and helps mitigate the psychological challenges associated with life post-exit. This proactive approach avoids the potential pitfalls of being left without focus or direction.
Health and Well-Being in Entrepreneurial Journeys
The importance of health and well-being is underscored as crucial to maintaining performance in the high-pressure environment of entrepreneurship. The speaker shares personal experiences of how the COVID-19 pandemic prompted a reevaluation of health habits, leading to significant lifestyle changes. By prioritizing exercise and nutrition, entrepreneurs can enhance their decision-making abilities, ultimately benefiting their businesses. A conscious commitment to wellness offers a competitive advantage, enabling leaders to navigate the demands of entrepreneurship with greater resilience.
The Nature of Desire and Fulfillment
A deep exploration of the concepts of desire, fulfillment, and happiness reveals the complexities that define an entrepreneurial life. The speaker asserts that desire can be a double-edged sword, motivating progress while also delivering distress when fueled by comparison or greed. True fulfillment comes from dedicating oneself to meaningful pursuits rather than chasing transient happiness. By focusing on impactful work and the betterment of others, one cultivates a sense of purpose that reinforces a more resilient and rewarding life.
Legacy and Community in Post-Career Journeys
The conversation underscores the significance of legacy and community for individuals transitioning out of their primary careers, particularly athletes. As many athletes face the abrupt end of their sports careers, building an enduring legacy through impactful investments becomes vital. The speaker emphasizes educating athletes on making informed decisions, thus preparing them for a fulfilling life beyond sports. By fostering a sense of purpose and community, post-career individuals can anchor themselves, using their experiences to support meaningful ventures that benefit society.
What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business?
This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why?
Well, Alex has seen enough of his post-exit founder friends getting stuck in full-blown existential crisis after they sold their company. He didn't want that to happen to him. I think honestly, if I had had that void, it probably would have not led to a productive use of my energy. I'm actually very happy that I had something immediately to jump into. And yeah, that's led to me not having to go through that challenging period that I see a lot of my friends go through, questioning their identity and everything.
In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL.
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