I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson Structured Notes from Interview with Andrew Wilkinson - Introduction: This blog post summarizes key takeaways from an interview with Andrew Wilkinson, co-founder and CEO of Tiny, a holding company often referred to as the "Berkshire Hathaway of the internet." The conversation covers various aspects of starting and scaling businesses, leveraging AI for automation, and the relationship between happiness and wealth. Finding a Great Startup Idea - Focus on your interests: Don't chase trendy ideas like restaurants or cafes, which are notoriously difficult and competitive. Instead, consider less popular but potentially profitable niches. "Fish where the fish are": Charlie Munger's advice emphasizes finding underserved markets with less competition. High competition leads to lower margins. Start small: Begin with a manageable project to gain early wins and build confidence. Don't try to deadlift 300 lbs on day one (analogous to launching a highly complex and competitive startup immediately). Initial wins are crucial: Early success builds momentum and belief in your abilities. Andrew's first web design agency provided this crucial early win. Avoiding a Job You Hate - Consider scalability: A small-scale business (like a solo pressure washing operation) is essentially a job. Focus on scaling to a point where you can delegate tasks you dislike. "Lazy leadership": Prioritize delegating or automating tasks you hate to focus on aspects you enjoy. Non-software businesses: Don't automatically gravitate towards software-based businesses. Consider your unique skills and advantages. Andrew's strength in sales allowed him to succeed in various industries. Identify profitable niches within your passions: Explore related areas within your interests to find opportunities. Andrew's passion for movies led him to invest in Letterboxd. Identifying Valuable Problems - Experience matters: Realistically assessing the value of a problem requires life experience and understanding of market realities. Understanding market value: Knowing what customers are willing to pay is crucial. Andrew's understanding of the real estate market informed his marketing strategy. Gut feeling and mental models: Experience and accumulated knowledge contribute to a gut feeling about the viability of an idea. AI can help refine this intuition. Leverage AI: Use AI tools like ChatGPT to analyze market data, assess business models, and understand industry challenges before committing significant resources. "Boring is Good" - Avoid hyper-competitive markets: Overly popular industries often attract intense competition, making it difficult to succeed. Focus on niche solutions: Addressing specific, underserved needs can lead to success even in seemingly boring areas. A form-filling software for government assistance is a good example. Avoid repeating past failures: Don't enter markets where others have consistently failed unless you have a truly innovative approach. Andrew learned this lesson with a bar venture. Business model over management: A great business model is more important than a brilliant management team. Lifestyle Businesses vs. Venture-Backed Companies - Bootstrap businesses can scale: Contrary to popular belief, bootstrapped businesses can achieve significant growth. Tiny's success demonstrates this. Tolerance for burning money: The main difference between bootstrapping and venture capital is the tolerance for financial risk. Moats and network effects: Focus on businesses with inherent advantages like strong brands or network effects to achieve sustainable growth. Choose your "big hairy audacious goal": Venture capital is often necessary for highly ambitious, capital-intensive ventures. Smaller, less competitive opportunities allow for bootstrapped growth. Market size matters: Small markets may be less attractive to venture capitalists, offering a competitive advantage for lifestyle businesses. Keys to an Amazing Business Model - Focus on "moats": Look for businesses with strong brands, network effects, or high switching costs to create a sustainable competitive advantage. Find businesses that are hard to mess up: Prioritize businesses with resilient structures and loyal customer bases. Don't disrupt for disruption's sake: Focus on creating value and solving real problems rather than simply disrupting existing markets. Long-term perspective: Invest in businesses with staying power, aiming for long-term growth and profitability. People and Management - People problems are the only problems: Focus on hiring and retaining high-quality individuals. Careful screening is essential: Thoroughly vet potential employees to avoid hiring difficult or problematic individuals. Don't try to change people: Hire individuals who already possess the necessary skills and fit the company culture. "If you think about firing someone, fire them": This heuristic helps identify potential problems early. Hire for what you need, not potential: Focus on hiring fully formed individuals with the required skills rather than relying on training and development. Let CEOs lead: Allow CEOs to operate autonomously, aligning their vision with the company's goals. Andrew's AI Stack and Use Cases - Tool Primary Use Case Notes Lindy.ai Workflow automation and AI agent creation Automates email management, calendar scheduling, CRM updates, etc. Replit Rapid web development and web app creation Uses Claude 4 for design and copywriting. Limitless Daily life recording and analysis Used for personal and professional reflection, relationship improvement, etc. Claude Writing ChatGPT General-purpose tasks Gemini Processing large datasets (e.g., medical records) Perplexity Deep research for meetings and conversations Replaces the need for a dedicated researcher. AI-powered automation: Andrew extensively uses AI to automate various aspects of his work and personal life. Reduced reliance on human assistants: AI has replaced the need for a full-time assistant for email management. Enhanced productivity and focus: AI tools help maintain focus and overcome challenges associated with ADHD. Improved communication and relationships: AI aids in clarifying communication and improving relationships. The Impact of AI on Jobs - Palm Trio analogy: Current AI capabilities are like the Palm Trio – a preview of future possibilities, but not yet fully realized. Potential for job displacement: Many knowledge work jobs are vulnerable to automation. The "single prompt" question: Will all jobs eventually be reducible to a single prompt? Adaptability and new skills: Focus on developing skills that complement AI, such as prompt engineering, business creation, and human interaction. Long-term uncertainty: The long-term impact of AI on employment is uncertain, with potential for both job displacement and the creation of new, unforeseen roles. Happiness and Money - Money doesn't buy happiness: Increased wealth did not alleviate Andrew's anxiety or improve his overall happiness. Internal vs. external factors: Happiness stems from internal factors rather than external achievements. Comparison and competition: The constant comparison with others fuels unhappiness, regardless of wealth. Reframing money: Andrew found happiness by redirecting his wealth towards philanthropic endeavors. Mindfulness and simplicity: Reducing material possessions and avoiding ostentatious displays of wealth contributes to contentment. Medication for mental health: Andrew found significant improvement in his mental well-being through medication for ADHD and anxiety. Key Takeaways and Summary This interview with Andrew Wilkinson provides valuable insights into entrepreneurship, AI, and the pursuit of happiness. Key takeaways include: Focus on niche markets with less competition. Start small and build up gradually. Leverage AI to automate tasks and enhance productivity. Prioritize building a strong team and fostering a positive work environment. Happiness is not solely dependent on wealth or external achievements. Address underlying mental health issues to improve overall well-being. The interview underscores the importance of adaptability in the face of technological advancements and the need to focus on solving real problems while leveraging the power of AI. Andrew's journey from barista to (former) billionaire offers a compelling narrative of both entrepreneurial success and the pursuit of genuine fulfillment. You’ll really grasp the difference between just creating designs (outputs) and being accountable for the actual results your designs achieve (outcomes) – it’s a game-changer for how you think about your work. This section helps you see how the designer's role is evolving, becoming less about execution and more about high accountability and driving the product vision, which might even blur the lines with a product manager's responsibilities. If you're looking to grow your career in design, you'll pick up some valuable, perhaps counterintuitive, advice on how to navigate by focusing on creating tangible outcomes, especially in today's fast-paced environment. You'll understand the unique value you bring as a designer, particularly your ability to rapidly prototype and test variations to quickly learn and achieve desired outcomes, effectively 'shortcutting' long processes. See, designing for growth is a high accountability, high agency role, right? And maybe the simple way of saying this is you're expected to create outcomes rather than just outputs. Yeah these might just be great outputs but not great outcomes. That is the main difference. What is the primary distinction between 'designing for product' (outputs) and 'designing for growth/revenue' (outcomes)? According to the speaker, what characteristics define a 'designing for growth' role? When a designer embraces an outcome-driven role, whose responsibilities tend to become 'blurry' with theirs? What 'counter-intuitive' advice is given for a designer looking to grow their career in the current environment? What is highlighted as something 'only a designer can do' in an outcome-driven environment, enabling shortcutting the process? You’ll realize why chasing 'cool' business ideas might lead you straight into a crowded, low-profit market, and how to spot unique opportunities where competition is scarce. You’ll understand why your first business should be something simple and easy to win at, building your confidence and momentum before tackling bigger challenges. You’ll learn the crucial difference between creating a true business and just creating a job for yourself, especially if you want to avoid getting stuck doing tasks you hate. You’ll discover how scaling your business and strategically delegating tasks can free you up to do what you love, rather than getting bogged down in the day-to-day grind. To truly be productive, you must intentionally create pockets of deep, uninterrupted work. It's not about working harder, but working smarter by eliminating distractions that fragment your focus. What is identified as a significant challenge people face in today's environment? What is the primary method suggested for becoming truly productive? Which of the following actions are recommended to support deep work? How is deep work compared to a muscle in the transcript? What specific technique is mentioned as a good starting point for developing focus periods? You’ll hear why focusing on 'boring' businesses, like software for filling government forms, can actually be incredibly profitable because fewer people are chasing them. The speaker shares a powerful personal story about losing $10 million by trying to compete in a 'sexy' but crowded market, giving you a real-world warning about popular trends. You’ll discover why it’s often a mistake to dive into business models where many others have already failed – sometimes the model itself is flawed, not just the management. You'll get a clear picture of the difference between complex, high-risk ventures (like running a bar) and simpler, more robust ones (like enterprise software), helping you spot better opportunities. You need to simplify complex ideas into digestible chunks. Avoid jargon unless absolutely necessary and explain it. What is identified as the first principle of effective communication in the transcript? According to the transcript, what should be done with complex ideas to make them effective? What advice is given regarding the use of jargon? What is the primary benefit of consistency in messaging, as stated in the transcript? You'll quickly realize that the idea of a 'lifestyle' or bootstrapped business being small is often a myth; you can actually build something massive, even doing hundreds of millions in revenue, without ever raising venture capital. This clip helps you see that the real difference between a bootstrapped company and a venture-backed one often comes down to how much money you're willing to 'burn' – and that burning cash isn't always necessary for growth if you choose the right market. You'll learn to redefine business success beyond just maximizing market share; it's about building a company you love, having a great life, and creating something valuable that people genuinely appreciate. You'll get a super helpful metaphor: 'fish where the fish are, but not where the professional fishermen are,' which is a smart way to think about finding market opportunities that are perfect for you but might not interest big venture capitalists. But he says that the most successful, most impactful organizations and people operate from the inside out. They start with why, then they'll move to how, then they'll move to what. If you want to attract specific, ideal, aligned clients, then you've got to be super clear on your specific why. According to Simon Sinek's framework, what is the most impactful sequence for organizations and individuals to operate? When a coach effectively communicates their 'why,' which part of the brain is primarily influenced to drive client action and engagement? What is a primary benefit for coaches who are 'super clear on their specific why'? Which of the following is NOT mentioned as a key benefit of a coach being clear on their 'why'? Why does the speaker suggest that 'my why is to help people' is not a specific enough 'why' for a coach? You’ll hear Andrew explain his journey from the stressful world of starting businesses to the calmer, more successful strategy of buying them, inspired by how Warren Buffett operates. You'll learn about his key philosophy: finding businesses with a 'moat' – something that makes them incredibly hard to mess up, whether it's a super strong brand or a powerful network effect where every new user makes the service better for you. You'll discover how his company, Tiny, approaches acquisitions with a surprisingly hands-off strategy, often leaving existing management in place to ensure a seamless transition. He shares a fascinating example of their acquisition of Sorado, the world's largest DJ software, and how his personal passion for DJing gave him a unique edge in understanding and valuing that business. So there's a lot of things that don't make sense from a physics perspective when you think about them when it comes to the brain and how it's actually working. If you are focusing on the things that are really, really, really important to you, your energy levels will be disproportionately high for those things. According to the speaker, what is often counter-intuitive when considering the brain's function? What happens to your energy levels when you focus on things that are really important to you? The speaker suggests that our understanding of the brain often clashes with what scientific discipline? What is the core idea being presented regarding energy and focus? You'll quickly understand why many business challenges aren't about the product or process, but fundamentally about the people involved. You'll realize why hiring someone with the intention of 'changing' them, much like in a relationship, is a strategy that rarely pays off. There's a straightforward, almost brutal piece of advice that will make you rethink holding onto employees you have doubts about. You'll hear a counter-intuitive take on hiring for current capability versus just potential, especially when it comes to leaders who, like 'elephants,' tend to follow their own instincts. The first step to effective delegation is clearly defining the outcome you want. And remember, delegation isn't about offloading work, it's about developing your team. What is identified as the crucial first step for effective delegation? According to the transcript, what is a common mistake leaders make when delegating? What is stated as the foundation of successful delegation? Beyond offloading work, what is the ultimate purpose of delegation emphasized in the segment? Instead of daily reports, what does the speaker suggest leaders should set for delegated tasks? You'll discover how tools like Lindy AI can completely revolutionize your inbox, acting like a super-efficient assistant that handles everything from categorizing emails to drafting replies, saving you tons of time. Get ready to be amazed by how platforms like Replit allow you to build complex web projects, like websites and web apps, all on your own, letting you ditch the need for large teams and truly unlock your creative potential. You'll hear about the 'Limitless' device, a wearable AI that records your day and helps you recall conversations, promises, and even gain surprising insights into relationship dynamics—it's like having a personal memory assistant and a therapist rolled into one. You'll also learn practical ways to use general AI like Gemini and ChatGPT for highly personal tasks, such as managing your health by training it on your medical records or even your medicine cabinet, offering truly personalized advice. The true secret to achieving anything significant is to focus on the process, not just the outcome. What's the smallest step I can take today to move towards that goal? According to the speaker, what is the 'true secret' to achieving anything significant? Instead of dreaming about the finish line, what actionable question does the speaker suggest asking? What does the speaker identify as the builder of momentum towards achieving big results? Which of these is given as an example of a 'smallest step' towards writing a book? You’ll hear how current AI tools are already changing roles like researchers and assistants, much like a 'Palm Trio' moment before the full 'iPhone' revolution of AI hits the mainstream. The discussion delves into a fascinating, somewhat unsettling idea: could jobs, even a CEO's role, eventually boil down to a 'single prompt' that AI executes, radically redefining what 'work' means? You’ll get some really practical advice: the best way to navigate this AI shift isn't to fear it, but to become incredibly proficient with these tools, using them to build wealth and discover entirely new, unexpected opportunities. The speaker shares a crucial mindset shift: it’s not AI that will replace you, but rather someone very good at using AI, so you should really lean into integrating these tools into your daily problem-solving. I'm a big advocate of just being very intentional. So if I'm dating, I'm dating to marry. I'm not just dating to date. I'm not dating to just fill up time. What is the speaker's primary approach to dating and relationships? According to the speaker, what is the ultimate goal when they are dating? What does the speaker identify as the main challenge in finding a partner? As one grows, what does the speaker say they increasingly learn about themselves? Why has the speaker been single for a while, according to the transcript? You'll really get a sense of how chasing extreme wealth, even to billionaire status, doesn't actually silence your inner critic or bring lasting happiness. The speaker offers a relatable insight: your internal 'anxiety loop' doesn't magically vanish just because your external circumstances improve or you move to a new, exciting place. You'll hear a surprisingly candid story about how even multi-billionaires still compare themselves to others, revealing that the struggle with 'keeping up with the Joneses' is a universal human experience. This part powerfully shows that no matter how much you achieve, the core anxieties often remain, leading you to realize the true source of contentment lies elsewhere. The first step to effective decision-making is to clarify your values. Finally, consider the long-term impact of your choices, not just the immediate gain. According to the speaker, what is the initial step towards effective decision-making? What is a potential consequence of not having clear values when making decisions? Why does the speaker recommend gathering diverse perspectives? What aspect of decision-making should be considered beyond immediate gains? You'll discover a fascinating shift in how he views wealth, realizing that giving away a significant portion of his money actually brought him more peace than accumulation ever did. You'll hear his incredibly personal account of how medication literally turned down the 'volume' on his anxiety, offering a profound sense of relief that changed everything for him. Prepare to be surprised by his journey to an ADHD diagnosis – it challenges common perceptions and highlights how addressing it transformed not just his work, but also his personal relationships. He bravely tackles the stigma around mental health medication, inviting you to rethink why we readily accept pills for physical ailments but hesitate when it comes to our brains, and even shares a smart tip about DNA testing for the right fit. when you're first starting out and you're trying to gain momentum, it's probably not the best choice to be putting out. what you need to be doing is building that no, like and trust factor with people. And you do that by actually sharing your unique experiences. Your unique perspectives. Your unique voice. According to the speaker, what is a common first piece of content for many new creators? Why are quote graphics not ideal for new creators trying to gain momentum? What key factor should new creators focus on building with their audience? What is the primary risk if a new creator primarily shares someone else's content?