I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

1. Consider SSRIs for Anxiety

If experiencing chronic anxiety that significantly impacts your life, consult a doctor about SSRI medication, as it can effectively reduce internal ’nasty voices’ and provide profound relief, much like treating a physical ailment.

2. Consider ADHD Medication

If diagnosed with ADHD, explore medication options, as it can significantly improve focus and executive function, transforming a ‘Times Square’ brain into a ‘quiet library’.

3. Seek Diagnosis for Self-Understanding

Pursue diagnosis for conditions like ADHD to gain self-understanding, even if you don’t medicate, as it enables lifestyle adjustments, dietary changes, and improved communication strategies with loved ones.

4. Make Hard Choices for Ease

Embrace the philosophy that ’easy choices lead to a hard life, while hard choices lead to an easy life,’ consistently opting for difficult decisions (e.g., firing, shutting down projects) when necessary, as they often lead to better long-term outcomes.

5. Reframe Wealth for Good

Reframe your relationship with wealth by directing a significant portion (e.g., 90%+) to philanthropic causes, shifting the ‘win’ from personal gain to making a positive impact, which can increase personal happiness.

6. Reduce Spending for Happiness

Consciously reduce excessive spending and accumulation of material possessions, as having more ‘stuff’ and the associated management can lead to decreased happiness and feeling ‘owned by your stuff’.

7. Maintain Humility and Normalcy

Actively strive to maintain a normal, humble lifestyle by driving a regular car, meeting people on neutral ground, and dressing modestly, to avoid appearing ‘out of touch’ and foster genuine connections.

8. Fish Where The Fish Are

Seek out business niches with lots of opportunity and little competition, rather than crowded markets where everyone is fighting for the same resources, to increase chances of profitability and success.

9. Avoid Repeatedly Failed Models

Do not enter business models where others have consistently failed, even if you believe you can do it better, as the underlying business model often dictates success more than management.

10. Seek Businesses with Moats

When evaluating businesses, look for those with strong ‘moats’ – competitive advantages like powerful brands, network effects, or high switching costs – that make them difficult to disrupt and ensure long-term staying power.

11. Start Small, Build Muscle

For first-time entrepreneurs, avoid highly rigorous and competitive ventures like the ’next great AI company.’ Instead, choose a simpler business to gain initial wins and build confidence, similar to starting with baby weights in a gym.

12. Seek Initial Business Wins

For first-time entrepreneurs, choose a simple business model that allows for immediate positive feedback and builds confidence, providing a crucial ‘first win’ to encourage continued effort.

13. Prioritize People Over Problems

Recognize that most business challenges are fundamentally ‘people problems,’ emphasizing the critical importance of surrounding yourself with smart, great people to navigate any disaster.

14. Carefully Filter Hires

Dedicate significant time to carefully filtering potential hires, ensuring you work with people you genuinely enjoy, as dealing with difficult individuals can make life incredibly stressful.

15. Don’t Try to Change People

Avoid hiring people based on the hope that you can change or mentor them into being a good employee, as personal experience suggests this rarely works out.

16. Fire Immediately if Doubting

If the thought ‘should I fire this person?’ crosses your mind even once, act on it immediately, as it’s often a signal that the person will not work out in the long run.

17. Hire for Need, Not Potential

Focus on hiring individuals who are already ‘fully formed’ and possess the exact skills and capabilities needed for the role, rather than solely hiring for potential and expecting to coach them into the desired employee.

18. Listen Closely to Intentions

When hiring, especially for leadership roles, listen incredibly carefully to candidates’ words and past experiences, as people generally gravitate towards doing what they’ve expressed or are good at.

19. Avoid Micromanaging Leaders

For leaders like CEOs, avoid trying to pull them in a specific direction or coach them against their natural inclinations, as they are likely to ‘sandbag’ ideas they don’t believe in, making efforts ineffective.

20. Leverage Unfair Advantage

When considering business ideas, identify and leverage your unique ‘unfair advantage’ and what you excel at, as this forms the foundation for a strong and differentiated offering.

21. Find Profit in Your Passions

Explore industries related to your passions, but then ‘sniff around’ to identify the profitable niches or service providers within that industry, rather than directly pursuing the passion itself if it’s not lucrative.

22. Pivot to Profitability

Combine your passion and skill set, then be willing to pivot slightly to find the most profitable application of those abilities, as demonstrated by shifting from small local web projects to higher-paying startup work.

23. Understand Problem’s Realistic Value

Before pursuing a business idea, gain a deep understanding of what people are realistically willing to pay to solve a particular problem, as this knowledge is crucial for identifying worthwhile opportunities.

24. Validate Ideas with AI

Leverage AI tools like Claude or ChatGPT to thoroughly research and validate potential business ideas, asking for breakdowns of numbers, challenges, regulatory moats, and operational costs to avoid ‘stupid businesses’.

25. Embrace Boring Business Ideas

Focus on ‘boring’ business ideas, such as form-filling software for government assistance, because they attract less competition and can generate significant revenue, unlike flashy, overfished markets.

26. Avoid VC-Backed Competition

If you’re bootstrapping, generally avoid directly competing with venture-backed businesses in the same space, as they have significantly more capital to burn, making it an uneven and difficult fight.

27. Avoid Commercial Fishing Holes

For non-venture-backed companies, seek out markets that are too small or unexciting for venture capitalists (’trawlers’), allowing you to build a profitable business without intense competition.

28. Scale to Delegate Hated Tasks

When starting a business, aim for a scale where you can hire employees to handle tasks you dislike, allowing you to focus on aspects you enjoy, transforming a ‘job’ into a true ‘business’.

29. Practice Lazy Leadership

Embrace ’lazy leadership’ by actively seeking to delegate or eliminate tasks you dislike as quickly as possible, becoming ‘Teflon for tasks’ to optimize your focus and enjoyment.

30. Master AI Tools for Wealth

For those in the workforce or new grads, become incredibly proficient with current AI tools to build wealth, which can then be diversified into investments like compute and energy, preparing for future economic shifts.

31. Become Proficient with AI

Actively integrate and become highly proficient with AI tools in your daily work, as those who master AI will likely replace those who don’t, making it a critical skill for career longevity.

32. Use ChatGPT for Flow State

Leverage ChatGPT to overcome mental blocks and ‘stay on track’ when encountering difficulties, especially for those with ADHD, enabling a continuous flow state and faster problem-solving.

33. Utilize AI Voice Mode

Actively use the voice mode feature in AI tools like ChatGPT to interact more naturally and efficiently, avoiding the need to type questions and enhancing the problem-solving experience.

34. Automate Workflows with Lindy.ai

Utilize Lindy.ai to build custom AI agents and workflows for tasks like managing emails (filtering, labeling, responding), scheduling, and calendar management, effectively replacing full-time administrative work.

35. Add Emojis to Calendar Events

Implement an AI agent to automatically add relevant emojis to every calendar event, creating a visually appealing and easily scannable schedule.

36. Automate Networking with AI

Create an AI agent that automatically researches contacts’ locations, updates your CRM, and proactively suggests networking opportunities when you travel, based on your schedule and contacts.

37. Use Replit for Web Projects

Utilize Replit as a ‘vibe coding platform’ to quickly build websites and web apps, leveraging its AI capabilities to generate designs and copy in specific styles, reducing reliance on large teams.

38. Use Limitless for Memory

Wear a Limitless device to record your daily interactions, allowing you to later query the AI to recall promises made, review conversations for communication improvement, or even reflect on personal growth.

39. Use Gemini for Large Data

For processing and analyzing extremely large datasets, such as extensive medical records, utilize Gemini 2.5 due to its superior capacity compared to other AI models.

40. Use Claude for Writing

Employ Claude for extensive writing tasks, as it is found to be the most effective AI tool for generating high-quality written content.

41. AI for Personalized Health

Digitize your medicine cabinet and current medications (e.g., via photos) and train an AI model on this data to receive personalized health advice, such as supplement recommendations or warnings about drug interactions.

42. Automate Meeting Preparation

Create an AI agent that automatically researches individuals and meeting contexts 30 minutes before scheduled calls, providing a concise summary via text to ensure you’re well-prepared.

43. AI for Commonality Discovery

When preparing for meetings, use AI to identify commonalities between yourself and the other person, generating conversation starters and ‘fun things to talk about’ to build rapport.

44. Get Checked for ADHD

Entrepreneurs, in particular, should consider getting checked for ADHD due to its prevalence in the demographic; use ChatGPT to ask initial screening questions or consult a doctor for formal testing.

45. DNA Test for Med Compatibility

Before starting SSRIs, consider a DNA test (e.g., 23andMe) to understand how you metabolize different drugs, allowing you to choose a medication with fewer potential side effects.

46. Ask Big for Greatness

Don’t be afraid to ‘ask big’ or ‘ask for amazing’ in your pursuits, as even if you don’t get exactly what you asked for, you might still achieve something great, as demonstrated by getting to meet Steve Jobs.