Secrets of Post-Exit Happiness

Summary

In this insightful interview, Shane Nean, the founder of Jun Bank and Easy Texting, shares his journey from being a nightlife entrepreneur to a successful investor and author. He discusses the challenges of transitioning from an operator to an investor, the importance of learning from mistakes, and the value of introspection and decision-making skills. Nean also reflects on his health journey, the impact of his mother's resilience, and his focus on being remembered as a good father and husband who contributed positively to society.

Takeaways

• 🎓 Shane Neuman's educational background includes studying computer science at NYU and initially pursuing a pre-med path, reflecting his early interest in medicine.
• 💡 His first entrepreneurial venture was a failed startup during the dot-com boom, which taught him valuable lessons about the tech industry and its volatility.
• 🌃 Shane's transition into the nightlife industry came from recognizing the inefficiencies in nightclub operations while picking up his girlfriend from work, leading to the creation of Junebug, a software platform for bars and nightclubs.
• 📈 Junebug's success was amplified by the addition of ticketing services, capitalizing on a market gap where smaller venues were not served by existing giants like Ticketmaster.
• 📲 The idea for EasyTexting emerged from Junebug's need to communicate with customers via text messages, which eventually became a separate, successful business due to high demand.
• 🔄 Shane's decision to sell Junebug and focus on EasyTexting was driven by the realization that EasyTexting had greater growth potential and was a 'shiny new object' compared to his long-standing commitment to Junebug.
• 💸 The sale of EasyTexting was prompted by burnout and a desire to spend more time with his new wife, reflecting a shift in life priorities after nearly two decades of non-stop work.
• 🏖 Post-exit, Shane experienced a period of adjustment, realizing the importance of not only preserving but also growing his wealth, which led him to learn investment strategies.
• 🧘 Shane's health journey included an intense focus on physical well-being, including cold plunging, weightlifting, and experimenting with various health supplements and practices.
• 🤔 The importance of introspection and learning from mistakes is highlighted by Shane's experience, emphasizing the value of personal growth and the adoption of new skills even after achieving success.
• 💡 Shane's humility and willingness to learn from experts in different fields, such as wealth management, demonstrate his adaptability and commitment to continuous improvement.

Q & A

What was the turning point for Shane Neuman that led him to become an investor?

Shane Neuman realized he needed to learn how to become a good investor after not wanting to start another business, recognizing that being a good investor is very different from being a good operator.

What are the two businesses that Shane successfully built and exited?

Shane successfully built and exited Junebug, a digital events powerhouse, and Easy Texting, the largest business SMS software platform in the US.

How did Shane's background in computer science influence his entrepreneurial journey?

Shane's background in computer science provided him with the technical skills to build platforms and software solutions, which he leveraged to create Junebug and Easy Texting.

What was the initial business idea that led to the creation of Junebug?

The initial business idea for Junebug came from Shane's observation of the inefficient pen-and-paper system used in nightclubs where his girlfriend worked, which led him to develop a platform to run nightclub and bar businesses.

What niche did Junebug fill in the market, and how did it grow the business?

Junebug filled the niche of providing a software stack for nightclubs and bars, similar to what Toast does for restaurants, and it grew by adding ticketing services when there was no existing solution like Ticketmaster for smaller venues.

What was the inspiration behind starting Easy Texting, and how did it evolve?

The inspiration behind Easy Texting was the realization that they had access to a lot of phone numbers and the emerging popularity of texting through devices like Blackberries. It started as an internal solution for Junebug and evolved into a standalone business due to its high demand and potential.

Why did Shane decide to sell Junebug, and what did he do with the capital from the sale?

Shane decided to sell Junebug because he saw more potential in Easy Texting and wanted to focus on growing that business. He used the capital from the sale of Junebug to invest in Easy Texting.

What challenges did Shane face during his transition from an entrepreneur to an investor?

Shane faced challenges such as learning to delegate, dealing with burnout, and shifting his mindset from a builder's mindset to an investor's mindset, which required a different approach and skillset.

How did Shane approach learning to become a good investor after his exit?

Shane approached learning to become a good investor by surrounding himself with experts in various fields, learning from them, and taking small bets to learn before developing his own investment thesis.

What is the book that Shane authored, and what is its significance?

Shane authored the book 'Nightlife: Lessons How I Conquered the Business of Partying with Tech', which shares his experiences and lessons learned from building businesses in the nightlife industry.

What advice does Shane give to new investors who have recently sold their companies?

Shane advises new investors to find good mentors, learn from them, and not to avoid certain asset classes but rather understand them well. He also emphasizes the importance of learning from mistakes and not taking investment too seriously to the point of losing focus on other aspects of life.