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Andrew Wilkinson: Tiny Holdings

Jul 26, 2022 1h 15m 34 insights
My guest is businessman and investor Andrew Wilkinson, who has made a career out of channeling his entrepreneurial spirit, but he knows that sometimes that energy can be a double-edged sword. We discuss the lessons learned acquiring 40 companies, why he struggled to find happiness and what changed, mimetic desire, competing with venture-backed companies, hiring and firing CEOs, getting back up after million dollar mistakes, and so much more. -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/ Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/ Follow Shane on Twitter at: https://twitter.com/ShaneAParrish
Actionable Insights

1. Perform a Dopamine Detox

If feeling hollow or losing meaning, conduct a ‘dopamine detox’ by completely abstaining from stimulating inputs (phone, email, music, podcasts, social media) for an extended period (e.g., a month). This can reset your brain’s reward system and allow you to find pleasure in simple activities again.

2. Implement Self-Binding for Habits

Acknowledge that willpower is often insufficient and implement ‘self-binding’ strategies to remove temptations and stimuli from your environment entirely. This could involve not keeping unhealthy foods in the house or using screen time limits on devices with a trusted person holding the passcode.

3. Prioritize Sleep to Manage Stress

When feeling stressed or overwhelmed, check your sleep status, as being underslept can magnify problems and negatively impact your emotional resilience. Prioritize adequate rest to maintain perspective and effectively manage challenges.

4. Maintain a Consistent Sleep Ritual

Establish and adhere to a consistent bedtime ritual, including winding down activities like watching TV, reading, and using low light, to ensure you fall asleep at the same time each night and improve sleep quality.

5. Just Get Started

Avoid the ’endless loop of research and never doing’ by taking action and getting started, as this prevents paralysis and allows for learning through doing.

6. Hire to Learn, Not to Perfect

Instead of perpetually measuring and delaying, hire the ‘wrong’ person first to gain immediate experience and learn what is truly needed. This approach prioritizes action and learning over seeking perfection upfront.

7. Recognize Mimetic Desire

Be aware of ‘mimetic desire,’ where you desire things simply because others around you desire them, rather than from an intrinsic want. This awareness can help you avoid endlessly striving for external validation and appreciate what you already have.

8. Curate Your Social Environment

Intentionally choose your social environment to avoid mimetic desire and unnecessary competition. Surround yourself with people whose values align with a lifestyle you genuinely desire, rather than constantly striving for what others have.

9. Identify Intrinsic Motivations

Reflect deeply to understand your true intrinsic motivations, such as a ‘sense of safety and security,’ rather than being driven solely by external desires modeled by others. This self-awareness helps align actions with genuine personal fulfillment.

10. Harness Anxiety for Productivity

If you experience anxiety, try to harness it for productivity by focusing on ticking off to-do items. This approach allows you to channel anxious energy into tangible accomplishments.

11. Adopt “Pleased, Not Satisfied” Mindset

Cultivate a mindset of being ‘pleased, but not satisfied,’ which allows you to appreciate current achievements while remaining driven to continuously improve and find better ways of doing things.

12. Trust Your Team & Delegate

Delegate effectively and trust your team, as removing yourself from daily operations can reveal their capability to perform excellent work independently and allow you to focus on higher-level decisions.

13. Cultivate Financial Discipline

Operate with financial discipline, especially when capital is scarce, by focusing on running a profitable business from day one. This approach fosters resilience and sustainable growth.

14. Focus on Profitable Niches

Seek out ‘boring’ but profitable niches where outcomes are predictable and competition from venture-backed companies is low. This strategy, often described as ‘fishing where the fish are,’ helps avoid high-risk, capital-intensive battles.

15. Tailor CEO Hiring to Company Stage

Adapt your CEO hiring strategy to the company’s stage: for later-stage companies, seek experienced leaders from similar industries who have scaled businesses to at least double the size; for early-stage companies, look for risk-averse number twos or threes from scaled companies who can take a concept and grow it.

16. Prioritize Trust and Vision Alignment in CEO Hiring

When hiring a CEO, prioritize ethics and trust (e.g., ‘would I let this person babysit my kids?’). Additionally, ensure strong alignment with their vision and strategy, as you cannot dictate their approach once hired.

17. Allow People to Learn from Experience

Recognize that you likely ’never, ever had any luck changing anyone’s mind,’ as people often need to come to their own conclusions and gain experience, even if it means making mistakes.

18. Embrace Learning from Mistakes

Embrace mistakes and ‘wrong’ hires as valuable learning opportunities, using them to ‘calibrate’ your understanding and identify what ‘good’ looks like in future endeavors.

19. Cultivate a Sense of Pace

Develop a ‘crazy sense of pace’ by immediately talking about new ideas, giving them a name, or creating a logo to make them feel real and push them forward. Prioritize getting started over perpetual planning to avoid inaction.

20. Avoid Deals with Bad People

Steer clear of negotiations and deals with individuals who act in bad faith or manipulate, as such partnerships inevitably backfire. As Charlie Munger advises, ‘you can’t make a good deal with bad people.’

21. Prove Concepts with Own Capital First

Before inviting external investors, prove concepts and ventures internally using your own capital. This approach, as practiced by successful investors, mitigates psychological stress and ensures conviction in the business model.

22. Seek Inefficiencies in Private Markets

Explore private markets for investment opportunities, as they can be less efficient than public markets and offer better deals, especially when founders are looking for buyers who align with their values rather than just financial gain.

23. Build Trust with Founders in Acquisitions

When acquiring businesses, build trust with founders by addressing their core concerns: fair compensation, care for employees, and the long-term legacy of their business. Emphasize a sustainable, non-disruptive approach to foster successful partnerships.

24. Disregard Daily Stock Fluctuations

For long-term investments, disregard daily stock price fluctuations, as they are irrelevant unless you are selling. Focus instead on the underlying earnings growth of the business, which the market price will eventually reflect.

25. Prioritize Exercise and Healthy Eating

Recognize that exercise and eating well are fundamental to overall health and well-being, forming the core of a healthy lifestyle.

26. Use Health Monitoring for Behavior Correction

Utilize health monitoring tools (e.g., glucose monitor, smartwatches) to gain insights into your body’s responses and correct behaviors, such as avoiding foods that negatively impact sleep. However, avoid obsessive monitoring and limit deep dives into health science to prevent anxiety.

27. Create External Incentives for Goals

Establish external incentives or social ‘shame’ mechanisms with trusted friends to help enforce commitment to personal goals, making it harder to break habits due to the undesirable consequence.

28. Engage in Structured Conversations

Participate in structured conversations, such as confidential entrepreneur forums or using prompt cards like those from School of Life, to foster deeper connections, gain impartial perspectives, and learn what’s truly happening in others’ lives.

29. Leverage Wealth for Learning & Connections

Utilize wealth to connect with fascinating people and expand your knowledge, such as by funding research labs to gain access to world experts or by hosting events to bring interesting individuals to your community.

30. Invest in Local Community Impact

Invest in projects and businesses within your local community, such as starting a news business, building a hotel, or acquiring local institutions, to make a tangible impact and foster a more interesting environment.

31. Prioritize Kids’ Love & Well-being

Prioritize ensuring your children feel loved and cared for, as this is the ultimate personal success, rather than seeking external validation or material achievements.

32. Cultivate a Love of Learning in Children

Encourage a love of learning in your children from an early age, hoping they can enjoy educational pursuits without the pressure of immediate financial necessity, allowing them to explore their passions freely.

33. Avoid External Validation & Ostentation

Resist the urge to seek external validation through material possessions or public displays of wealth, as these often fail to bring true satisfaction and can make you a target for criticism or envy.

34. Fund Scientific Research

Consider funding scientific research through a foundation, applying business skills to help bring lab discoveries into clinical practice and make a tangible impact on health and well-being.