Exit Paradox Alex Macdonald. A $300M Exit is No Reason to Retire
Feb 18, 2025
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.
AI Snips
Chapters
Transcript
Episode notes
Lunch on Alex
- Alex Macdonald met Anastasia Sapan on the day news of his $300M company exit leaked.
- Their mutual friend jokingly insisted Alex pay for everyone's lunch, which he did.
Velocity Black's Journey
- Velocity Black, Alex's first business, started as a mobile payment app.
- It pivoted to a digital concierge service, eventually acquired by Capital One.
Building for Fulfillment
- Alex started his second company, SQL, before selling Velocity Black to avoid an existential crisis.
- He finds fulfillment in building and believes founders should build again.