Kickoff Sessions

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


Listen Later

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


Support the show

...more
View all episodesView all episodes
Download on the App Store

Kickoff SessionsBy Darren Lee

  • 4.7
  • 4.7
  • 4.7
  • 4.7
  • 4.7

4.7

3 ratings


More shows like Kickoff Sessions

View all
London Real by Brian Rose

London Real

1,204 Listeners

The School of Greatness by Lewis Howes

The School of Greatness

21,099 Listeners

The Mindset Mentor by Rob Dial

The Mindset Mentor

13,500 Listeners

Tom Bilyeu's Impact Theory by Impact Theory

Tom Bilyeu's Impact Theory

4,690 Listeners

Bedros Keuilian Podcast Show by Bedros Keuilian

Bedros Keuilian Podcast Show

2,255 Listeners

The Game with Alex Hormozi by Alex Hormozi

The Game with Alex Hormozi

4,374 Listeners

The Diary Of A CEO with Steven Bartlett by DOAC

The Diary Of A CEO with Steven Bartlett

7,056 Listeners

Modern Wisdom by Chris Williamson

Modern Wisdom

3,769 Listeners

On Purpose with Jay Shetty by iHeartPodcasts

On Purpose with Jay Shetty

26,938 Listeners

The Daily Motivation by Lewis Howes

The Daily Motivation

912 Listeners

The Mel Robbins Podcast by Mel Robbins

The Mel Robbins Podcast

19,448 Listeners

First Things THRST by Mike Thurston

First Things THRST

89 Listeners

Tate Therapy by Top G

Tate Therapy

270 Listeners

BigDeal by Codie Sanchez

BigDeal

755 Listeners

Jack Neel Podcast by Jack Neel

Jack Neel Podcast

26 Listeners