SUMM

Many first-time entrepreneurs make the mistake of starting in highly competitive or "cool" industries (e.g., AI, restaurants), which often leads to failure.
It's easier to succeed by targeting less crowded markets with less competition, even if they seem less glamorous (e.g., funeral homes, pest control, government form software).
Andrew emphasizes "fish where the fish are," suggesting entrepreneurs seek out small fishing holes (niche markets) with lots of fish (demand) and few fishermen (competitors).
Early wins in simple, service-based businesses help build confidence and momentum.
Choosing a business you enjoy and that plays to your unique strengths or "unfair advantage" increases odds of success.
Repeatedly going into business models where others have failed is risky—many industries are tough for reasons not obvious from the outside.

Starting a business that's too hands-on can become a job you dislike unless it reaches scale (with employees, systems).
Scale allows founders to move away from daily repetitive work and focus on what they love (e.g., sales, digital marketing).
"Lazy leadership" is useful: quickly delegate or avoid the tasks you hate to maximize satisfaction and efficiency.

The decision to choose between a digital/software business and a physical/real-world business (like pressure washing) depends on your unique skills and advantage.
Look for profit opportunities in adjacent industries—for example, restaurant vendors (cleaning services, suppliers) might be more lucrative than owning the restaurant itself.
Success often comes from leveraging your background and skills in an industry you understand deeply.

Find the most profitable application of your existing skills (e.g., shift focus from low-paying clients to higher-budget clients such as realtors or wealth managers).
Repeatedly refine your focus to discover where the best return on effort exists.

Many fail by entering industries with lots of historical failures or active, aggressive competition; this is rarely outsmarted with just better execution.
Flashy, highly competitive ideas (like productivity apps, bars, or local news) are often traps with low odds of success and high stress.
Boring, "unsexy" businesses may prove surprisingly lucrative and less competitive (e.g., government form-filling services).
Bootstrapped businesses can scale large without raising venture capital, potentially reaching hundreds of millions in revenue, especially in less crowded markets.

Bootstrapped (lifestyle) companies are not inherently small; they can become sizable if the business model has a strong moat (brand, network effect).
Venture scale requires burning significant capital, often best reserved for massive, highly competitive or technologically complex opportunities.
Entering a space already targeted by venture capital requires a different set of expectations; bootstrapping works best where the market is too small for VC interest and competitive intensity.
Sustainable success often comes from smaller, focused, and non-VC-appealing niches.

Great businesses have a strong moat, such as a beloved brand or significant network effect making them difficult to disrupt (e.g., Letterboxd, Coca-Cola).
High switching costs (e.g., Salesforce) can provide defensibility, though this is less consumer-friendly.
When buying businesses, Andrew leaves successful teams in place, making minimal changes, and seeks businesses that are resilient, not easily broken by staffing changes.

People issues are the root of most business problems; filtering for high-quality, compatible people is critical.
Bad hires are rarely fixed by coaching; if there's doubt about someone, swift action is better.
CEOs and key hires will follow their instincts and experiences, not your guidance—align hiring with actual experience and expertise needed.
Hire fully-formed, experienced people for specific needs rather than solely for potential.

Andrew uses AI tools (notably Lindy) to automate most email, calendar, CRM, and task management, replacing the need for a personal assistant.
Builds and manages multiple AI agents to process routine tasks, enhance productivity, and improve organization.
Other AI tools used: Replit for coding/web projects, Limitless for personal record-keeping, Claude and Gemini for writing and large document processing, Perplexity for research.
AI is used for creative productivity hacks—automated meeting preparation, personalized recommendations, medicine cabinet inventory, and more.
The AI "stack" supports work that previously required several team members.

Job displacement driven by AI is already underway in research, translation, assistants, and administrative support.
More advanced AI could dramatically alter all knowledge work, especially if models achieve the capabilities predicted by leading researchers.
Short-term changes are often overestimated, long-term shifts underestimated; in the medium term, many new opportunities will emerge even as established roles disappear.
Andrew advises becoming highly proficient with AI tools to build wealth and remain relevant as the landscape evolves.
Prompts may become more important than coding itself as AI interfaces become more natural and automation increases.

Money and external achievement do not resolve internal sources of anxiety or unhappiness.
Anxiety, stress, and negative comparison persist at all levels of wealth.
True happiness is not found in chasing ever-increasing milestones; reframing the pursuit of money (e.g., towards philanthropy) and reducing attachment to possessions increases satisfaction.
Medication (SSRIs for anxiety, ADHD medication) had a far greater positive impact on Andrew’s happiness than money or business success.
Societal stigma around mental health medication is often misplaced; addressing root personal challenges, even with medication, can be transformative.
Discovery of ADHD led to greater self-understanding and improvements not only professionally, but also in personal life and relationships.

Andrew recommends two books: "The Laws of Human Nature" by Robert Green (on psychology and behavior), and "How to Get Rich" by Felix Dennis (insights into wealth, its drawbacks).
Favorite recent product: Madic robot vacuum (machine vision-powered home cleaning).
Life motto: "Easy choices, hard life; hard choices, easy life."
Memorable personal story: Met Steve Jobs as a teenager, demonstrating that asking boldly can lead to surprising experiences.
Invitation to contact Andrew if visiting Victoria, Canada or if considering selling a high-quality business that fits Tiny’s acquisition criteria.

I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson