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🎙️ Cheeky Pint: A Cheeky Pint with serial entrepreneur Pieter Levels

Serial entrepreneur Pieter Levels on building in public and living as a digital nomad

🌲 Evergreen 🎧 Podcast 👔 Business

🎙️ Cheeky Pint: A Cheeky Pint with serial entrepreneur Pieter Levels

PODCAST INFORMATION

Cheeky Pint
A Cheeky Pint with serial entrepreneur Pieter Levels: Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
John Collison (Host)
Pieter Levels (Guest) - Serial entrepreneur, digital nomad, founder of Nomad List, Remote OK, and PhotoAI
Episode Duration: approximately 22 minutes
Full Transcript on Substack: https://cheekypint.substack.com/p/a-cheeky-pint-with-serial-entrepreneur

🎧 Listen here.


HOOK

Pieter Levels, the most prominent indie hacker who has built multiple million-dollar businesses entirely by himself, shares his unconventional wisdom on entrepreneurship, digital nomading, and why VC-backed startups often burn money without creating real value.


ONE-SENTENCE TAKEAWAY

The indie hacker approach of building sustainable, profitable businesses without venture capital can lead to both financial independence and personal freedom, as demonstrated by Pieter Levels' portfolio of successful solo ventures.


SUMMARY

This episode of Cheeky Pint features John Collison in conversation with Pieter Levels, a serial entrepreneur known for building multiple successful businesses entirely by himself, including Nomad List ($700k ARR), Remote OK ($3.4 million revenue), and PhotoAI ($600k ARR). The conversation explores Levels' journey from being a 12-year-old trying to make money online to becoming one of the first YouTube creators and eventually a successful indie hacker.

Levels discusses his philosophy on entrepreneurship, contrasting the indie hacker approach with the VC-backed startup model. He expresses frustration with companies that raise massive funding without having real traction or users, advocating instead for validating ideas and building sustainable businesses first. Despite having VC interest, Levels has never raised funding, valuing the freedom and ownership that comes with building profitable businesses independently.


The conversation touches on Levels' experience as a digital nomad who has lived in over 40 countries and 150 cities. While he recommends travel for expanding horizons, he acknowledges the loneliness and psychological challenges of being untethered from one's foundational culture. He credits Patrick McKenzie (patio11) as an early inspiration for showing that it's possible to make honest, clean businesses online.

Levels discusses the power of personal branding, noting that his 125,000 tweets over 10 years have helped build his reputation to the point where he can sell $50,000 worth of preorders for a book before writing it. He also talks about the growing importance of ChatGPT referrals, which have grown from 4% to 20% of his traffic in just one month.

The conversation also explores Levels' approach to automation, particularly in moderating his 40,000-person community using GPT to handle conflicts impartially. He also discusses investment philosophy, criticizing home country bias and recommending simple index funds for most people.


Levels shares his thoughts on European entrepreneurship, launching the EU accelerationism movement to address regulatory burdens that hold back European talent. He reflects on Stripe's API evolution and offers suggestions for keeping it simple and user-friendly.

The episode concludes with Levels contemplating the future, expressing gratitude for his current lifestyle and openness to change while emphasizing his happiness with his current path of building businesses and traveling with his girlfriend.


INSIGHTS

  1. The indie hacker approach of building sustainable, profitable businesses without venture capital can lead to both financial independence and personal freedom.
  2. VC-backed startups often create unrealistic expectations of becoming unicorns, when a $10 million per year business with full ownership would be more valuable for most founders.
  3. Digital nomading expands horizons and changes people fundamentally, but it can be lonely and psychologically taxing as one becomes untethered from their foundational culture.
  4. Personal branding built through consistent content creation (like 125,000 tweets over 10 years) can create significant business opportunities and trust.
  5. AI tools like ChatGPT are rapidly becoming important traffic sources and can help automate business operations, such as community moderation.
  6. Most people would be better off with simple index fund investments rather than complex wealth management products or home country bias.
  7. European entrepreneurship is held back by regulatory burdens and a cultural skepticism toward business success, despite having talented people.
  8. Simple, user-friendly APIs are crucial for developer tools, as most people want to get started quickly without complexity.
  9. Automation is essential for indie hackers to manage multiple projects without getting overwhelmed by operational work.
  10. The most successful indie businesses solve real problems the founder personally experiences, rather than chasing market trends.


FRAMEWORKS & MODELS

  1. Indie Hacker Business Model: Building sustainable, profitable businesses without venture capital funding. This model prioritizes validation before scaling, ownership retention, and organic growth. It allows founders to maintain control and build businesses that generate significant income ($1M+) without the pressure of becoming a unicorn.
  2. Digital Nomad Lifestyle Framework: Living and working remotely while traveling the world. This framework emphasizes the transformative power of travel for expanding horizons while acknowledging the psychological challenges of becoming untethered from one's foundational culture. It requires rebuilding social connections and adapting to new environments continuously.
  3. Personal Brand Building Strategy: Creating a strong online presence through consistent content creation over time. Levels built his brand through 125,000 tweets over 10 years, establishing himself as a trusted authority. This personal brand becomes a valuable asset that can be leveraged for new product launches and business opportunities.
  4. Automation-First Business Operations: Implementing AI and automation tools to handle routine business tasks, allowing solo founders to manage multiple projects simultaneously. Levels uses GPT for community moderation and other operational tasks, reducing the need for hiring and management.
  5. EU Accelerationism Movement: A crowdsourced approach to identifying and addressing regulatory barriers to entrepreneurship in Europe. This framework involves gathering ideas from thousands of people, upvoting the most promising solutions, and advocating for changes that make it easier to start and run businesses across Europe.


QUOTES

  1. "What I hate most about VC stuff is when you see people burn money. You probably hate this as well. A company of no users raises $50 million, $100 million, and you're like, 'What is this product?' Like, it doesn't have any traction and it's just hype." - Pieter Levels
  2. "But if you're a founder and you raise money, you kind of need to go big or bust, right? It's hard to stay in between. You can't make $10 million a year. You kind of need to make $100 million a year. You kind of need to become a unicorn." - Pieter Levels
  3. "The money in your bank account is how much value you added to society. And in Europe, that completely does not... They really think different. In America, you get much more respect for being an entrepreneur." - Pieter Levels
  4. "It was extremely lonely. I was like, 'This is amazing.' And then you lose contact with the grounds of your own culture, your home country. And everything's fine, people are nice, but you're like… It fundamentally removes your foundational culture at some point." - Pieter Levels on digital nomading
  5. "I think of course it's part of it [personal branding], but I also work really hard, because I tweeted, I think, 125,000 times over 10 years, so it's like 40 tweets a day." - Pieter Levels
  6. "ChatGPT, a month ago, was... So, if you have the Google traffic, that's like 100%. ChatGPT was, like, 4%. Now it's 20%." - Pieter Levels on the growth of AI referrals
  7. "It's very important to invest your money well. And most people don't know personal finance. Like, you don't get it in school. You save money, but your money, your cash, disappears the moment you have it." - Pieter Levels
  8. "I think it's actually good that it's going so bad in Europe now, because it's almost like the patient is so sick—finally, Europeans are like, 'Maybe we should do something.'" - Pieter Levels on European entrepreneurship
  9. "Keeping that [original Stripe mentality] is so important, keeping the original soul of the company. And I think you're doing a great job. Because essentially, I don't want to go into Stripe to do anything. I want to go there to see how much money I make, and I want to go back to my coffee and code a little bit." - Pieter Levels
  10. "I'm just very happy. I'm every day grateful to be able to live this life, and it's so good. So thank you." - Pieter Levels on his current lifestyle


HABITS

  1. Build businesses that solve your own problems: Levels creates products to address challenges he personally faces, ensuring genuine demand and understanding of the problem space.
  2. Maintain consistent online presence: Levels tweets approximately 40 times per day, building his personal brand and staying connected with his audience over a decade.
  3. Automate business operations: Use AI tools like GPT to handle routine tasks such as community moderation, allowing you to focus on creative work and new projects.
  4. Invest simply and avoid home country bias: Levels recommends index funds like the S&P 500 rather than complex investment products or concentrating investments in one's home country.
  5. Travel to expand horizons: Levels advocates for digital nomading as a way to fundamentally change one's perspective, while acknowledging the psychological challenges involved.
  6. Keep projects running: Levels maintains many of his 70+ projects even if they generate small revenue, preserving internet history and maintaining URLs.
  7. Validate before scaling: Rather than raising large amounts of funding, Levels advocates for proving a business concept first and growing organically.
  8. Learn from successful indie hackers: Levels credits Patrick McKenzie (patio11) as an early inspiration for showing that honest, clean online businesses are possible.
  9. Advocate for regulatory reform: Levels actively promotes changes to make entrepreneurship easier in Europe through his EU accelerationism movement.
  10. Stay flexible and open to change: While committed to his indie hacker path, Levels remains open to new experiences and opportunities, including beginning to invest in other startups.


REFERENCES

  1. Stripe: The payment processing platform that Levels has used extensively since 2014, noting how it enabled him to start making money online.
  2. Patrick McKenzie (patio11): An early inspiration for Levels, who demonstrated that it's possible to make $60,000 annually with simple online businesses like Appointment Reminder.
  3. Nomad List: Levels' business that reached $700k ARR, helping people find places to live and work remotely.
  4. Remote OK: Levels' business that reached $3.4 million in revenue, connecting remote workers with job opportunities.
  5. PhotoAI: Levels' business that reached $600k ARR, demonstrating his ability to create multiple successful products.
  6. EU accelerationism (EU/acc): A movement started by Levels to address regulatory barriers to entrepreneurship in Europe, inspired by Beff Jezos' e/acc movement.
  7. ChatGPT: The AI tool that has grown from 4% to 20% of Levels' traffic in one month, showing the increasing importance of AI referrals.
  8. Vanguard: The investment company that Levels recommends for simple index fund investing, particularly for Europeans who may have limited options.
  9. Go Effing Do It: A 10-year-old product built by Levels that still runs on Stripe, helping people commit to goals with financial stakes.
  10. Cursor: An AI coding tool that Levels has invested in, showing his expanding interest in the AI space beyond just using the tools.



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