#263 Dakota Robertson - Writing Online Made Me $1M+ by 26

Kickoff Sessions

Watch This NEXT: https://www.youtube.com/watch?v=HlK2P76_ZZs

Dakota Robertson didn’t build a $1M business by going viral—he did it by mastering the fundamentals.
He built a system that works—and stuck to it.
In our conversation, he shared the exact steps he took to go from barely making ends meet to running a million-dollar writing business by 27.
Most writers focus on the wrong things:
- Trying to appeal to everyone instead of a specific audience
- Writing without a simple goal or system
- Being afraid to sell their work
But Dakota kept it simple and focused on what matters:
- Clarity
- Solving specific problems
- Consistency in execution
Here’s what we covered in the episode:
- How Dakota turned tweets into long-term revenue
- The unsexy habits: discipline and iteration
- How to find niches that pay—even with a small audience
- Why selling is a skill—and how writing builds trust
- Why solving problems beats entertaining every time
This isn’t just a conversation about writing—it’s a roadmap for freedom.
Freedom to work anywhere.
Freedom to grow without limits.
Freedom to turn your ideas into income.
If you want to learn how to write online and build a business that lasts, this is the episode for you.
Connect with Dakota: https://www.instagram.com/yodakota/?hl=en

(00:00) Introduction to Dakota Robertson
(01:10) Overcoming Addictions
(08:10) Life in Colombia
(11:42) Why Dakota Shut Down his Agency
(14:30) Running an Agency vs. Coaching Business
(17:36) Understanding Your Client
(19:42) Helping Others Achieve Freedom
(24:17) Breaking Free from Scarcity Mindset
(27:29) Lessons Learned from Mentors
(32:08) Sahil Bloom’s Five pillars of Wealth
(37:10) Dakota's Early Life
(42:41) Processing Loss and Moving forward
(50:17) Trying Ayahuasca
(52:24) The Importance of Fatherhood and Raising Kids
(58:27) Social Trends and Political Correctness
(59:58) Eastern Medicine, Ayahuasca, and Alternative Healing
(01:03:04) Personal Experiences with Energy Healing
(01:06:25) The Challenge of Growing an Audience
(01:07:52) The Curse of Knowledge in Teaching
(01:10:25) Would Dakota Ghostwrite a Book?
(01:16:03) Understanding Your Audience
(01:18:27) Building Credibility in Your Niche
(01:24:11) The Reality of Building a Sustainable Brand
(01:30:37) Dakota’s Personal and Business Goals
(01:36:04) Learning from Alex Hormozi
(01:41:32) Lessons from Software Development and Startups
(01:45:22) Overcoming Delusions in Business Growth

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Chapters

1. Achieving Freedom Through Online Writing (00:00:00)

2. Navigating Personal Habits and Entrepreneurship (00:03:54)

3. Building a Lead Generation System (00:10:29)

4. Finding Freedom Through Self-Improvement (00:21:30)

5. Investing in Skills for Long-Term Success (00:30:34)

6. Navigating Family Struggles and Addiction (00:35:23)

7. Navigating Family Tragedy and Self-Healing (00:42:41)

8. Social Dynamics and Alternative Medicine (00:55:04)

9. Creating a Unique Brand Framework (01:07:33)

10. Navigating Niche Expertise and Business Growth (01:21:09)

11. Scaling Business Growth Through Strategic Planning (01:28:54)

12. Challenges in Software Development and Funding (01:41:04)

13. The Genius Behind 600k a Month (01:46:22)