Ankur Nagpal is a prominent entrepreneur and investor best known as the founder of Teachable, a platform that empowered creators to build and sell online courses, which he later sold for a reported $250 million. Now, as the founder of Vibe Capital, he is an active angel investor, backing the next generation of founders. His journey from a bootstrapped founder to a successful investor provides a wealth of practical, no-nonsense advice on building products, achieving financial freedom, and navigating the creator economy.

On Entrepreneurship and Building Startups

Nagpal’s approach to building companies is refreshingly pragmatic, emphasizing profitability, sustainable growth, and solving real-world problems over chasing venture capital hype.

1. "Don't start a business to start a business. Start a business to solve a problem."

2. "The only three things that matter in a startup are: 1. Building a product people want and will pay for. 2. Getting that product in front of said people. 3. Not running out of money."

3. "For the first two years of Teachable, my co-founder and I took home $0 in salary. We lived off savings and consulting gigs."

4. "I am a BIG fan of building profitable companies as a default. If you need to raise money, do it from a position of strength, not desperation."

5. "It’s better to have 100 people that love you than 1,000,000 people that sort of like you."

6. The "Cockroach" Mentality: Nagpal is a proponent of being a "cockroach"—a company that is incredibly hard to kill because it manages its finances wisely and can survive lean times.

7. "Your first 100 customers should come from manual, unscalable processes. Go to conferences, do 1-on-1 demos, and hand-hold them through the process."

8. "The biggest mistake first-time founders make is they think they are playing the 'startup' game. They're not. They're playing the 'small business' game."

9. Permissionless Apprenticeship: Instead of asking for permission to learn, just start doing. Rebuild a landing page for a company you admire, write spec copy—prove your value upfront.

10. "If you are not embarrassed by the first version of your product, you’ve launched too late." (A classic startup axiom he frequently references).

11. On naming his company: He originally called it Fedora, but a constant stream of support tickets about the Linux distribution forced him to rebrand to the more descriptive "Teachable."

12. "Most startups don't die of starvation, they die of indigestion. They try to do too much, too soon."

13. "Ideas are worthless. Execution is everything."

14. The Power of Side Projects: Teachable started as a side project to solve Nagpal's own problem—a desire to teach a course on marketing. The most authentic businesses often start this way.

15. "The best way to learn how to run a business is to run a business."

On The Creator Economy and Product Strategy

Having built a cornerstone company in the creator economy, Nagpal has a deep understanding of what creators need and how to build products that serve them.

16. "The creator economy is not new. It's just that the tools have gotten better."

17. "The future of education is not one-to-many, but many-to-many. Everyone is a teacher and everyone is a student."

18. "Don't just sell a course. Sell a transformation. People don't buy information, they buy a better version of themselves."

19. "The most successful creators are the ones who are most authentic. They're not trying to be someone they're not."

20. "The key to a successful product is to find a small, passionate niche and serve them better than anyone else."

21. "At Teachable, we focused on the 'middle class' of creators. Not the superstars, but the people who were making a full-time living from their passion."

22. "The best products are the ones that are simple, intuitive, and easy to use."

23. "Listen to your customers, but don't let them dictate your product roadmap. They'll always ask for faster horses."

24. Focus on the Job-to-be-Done: Customers weren't hiring Teachable to "build a course." They were hiring it to "make a living online." This framing changes everything.

25. "Your product is not your baby. Be willing to kill your darlings if they're not working."

On Leadership, Management, and Culture

Nagpal's leadership style is transparent and direct, with a focus on creating a culture of ownership and high performance.

26. "The most important job of a CEO is to not run out of money."

27. "Hire slow, fire fast. A bad hire can be toxic to a team."

28. "I'm a big believer in radical transparency. At Teachable, everyone knew our revenue, our churn, and our bank balance."

29. "Give your team autonomy, but hold them accountable for results."

30. "The best way to lead is by example. I would never ask my team to do something I wouldn't do myself."

31. Asynchronous Communication as a Default: He is a strong advocate for written, long-form communication to enable deep work and respect people's time.

32. "Culture is not what you say, it's what you do. It's the sum of the decisions you make every day."

33. "I don't believe in work-life balance. I believe in work-life integration. Your work should be a part of your life, not something you escape from."

34. "The best perk you can give your employees is a clear mission, a great team, and the opportunity to do meaningful work."

35. "Celebrate your wins, but don't get complacent. The competition is always catching up."

On Angel Investing and Wealth

After selling Teachable, Nagpal shifted his focus to investing through Vibe Capital, sharing his lessons on wealth creation and the mindset of an investor.

36. "The best angel investors are the ones who have been in the trenches themselves. They can provide not just capital, but also empathy and advice."

37. "I invest in founders, not ideas. I'm looking for people who are smart, scrappy, and have a chip on their shoulder."

38. "The biggest mistake I see founders make when fundraising is they're not prepared. They don't know their numbers, they don't have a clear vision, and they haven't done their homework on the investor."

39. "Don't raise money unless you have to. Every dollar you take is a dollar you have to return."

40. Financial Freedom is the Goal: "The point of making money is not to buy fancy things. The point of making money is to buy your freedom."

41. On his own journey: "For the first time in my life, I felt I had f*ck you money... The kind of money that meant I didn’t have to work for anyone else ever again."

42. "The most valuable asset you have as an investor is your reputation. Don't be a jerk."

43. "I'm more interested in the 'why' than the 'what'. Why are you building this? Why now? Why are you the right person to do it?"

44. "The best investments are the ones that are non-obvious and contrarian."

45. "Don't be afraid to pass on a deal. FOMO is a terrible reason to invest."

On Life and Personal Philosophy

46. "The best way to predict the future is to invent it."

47. "Your twenties are for learning, your thirties are for earning."

48. "Be a student for life. The world is constantly changing, and you need to be constantly learning to keep up."

49. "The biggest risk is not taking any risk. In a world that is changing so quickly, the only strategy that is guaranteed to fail is not taking risks."

50. "Don't compare your beginning to someone else's middle. Everyone starts at zero."

Sources

Ankur Nagpal's Blog - "The Only Thing That Matters": A foundational essay where he outlines the core priorities for any startup. Link: https://www.ankurnagpal.com/the-only-thing-that-matters

Indie Hackers - "How I Built and Sold a Profitable SaaS Business for $250M": A detailed interview covering the early, lean years of bootstrapping Teachable. Link: https://www.indiehackers.com/podcast/173-ankur-nagpal-of-teachable

Ankur Nagpal's Blog - "The Ultimate Guide to Bootstrapping": This post details his philosophy on why profitability should be the default and the benefits of being a "cockroach" startup. Link: https://www.ankurnagpal.com/the-ultimate-guide-to-bootstrapping

Ankur Nagpal's Blog - "Permissionless Apprenticeship": A popular essay explaining how to gain skills and experience by proactively doing the work without waiting to be asked. Link: https://www.ankurnagpal.com/permissionless-apprenticeship

My First Million Podcast - Interview with Ankur Nagpal: In this podcast, he recounts the full origin story of Teachable, including the original name "Fedora" and the pivot. Link (Reference): Search for "Ankur Nagpal My First Million Podcast" for various clips and transcripts.

The Pomp Podcast - "#521: Ankur Nagpal on The Future of The Creator Economy": An interview where he discusses the evolution of the creator economy and Teachable's role in serving the creator middle class. Link (Reference): Search for "Ankur Nagpal Pomp Podcast".

Ankur Nagpal's Blog - "The Teachable Operating System": An essay where he touches on the importance of transparency and internal communication as part of their company culture. Link: https://www.ankurnagpal.com/the-teachable-operating-system

Ankur Nagpal's Twitter Feed (@ankurnagpal): He frequently tweets about his preference for async communication and long-form writing in a remote work environment. Link: https://twitter.com/ankurnagpal

Vibe Capital Website & Ankur's Blog: His investment thesis and advice for founders are spread across the Vibe Capital site and his personal blog under the "Investing" category. Link: https://www.ankurnagpal.com/investing

Ankur Nagpal's Blog - "The $250 Million Exit": A candid post about the emotional and practical realities of selling his company and achieving financial freedom. Link: https://www.ankurnagpal.com/the-250-million-exit

Ankur Nagpal's Blog - "20s vs 30s": An essay reflecting on the different priorities and goals for each decade of a professional's life. Link: https://www.ankurnagpal.com/20s-vs-30s