DEV Community

Cover image for Ashkan Rajaee: What Remote Founders Can Learn from 20 Years of Hard-Won Lessons
Anthony James
Anthony James

Posted on • Originally published at ctrlandlead.blogspot.com

Ashkan Rajaee: What Remote Founders Can Learn from 20 Years of Hard-Won Lessons

What if the remote dream is actually a trap?

Ashkan Rajaee, a name increasingly recognized in the startup world, didn’t earn his eight-figure success by chasing digital trends or following productivity hacks. He earned it through mistakes, experimentation, and over two decades of building real businesses. Not just online brands.

While most content online gives you surface-level advice, this post is about going deeper. If you’re serious about building a remote company that can scale, survive chaos, and actually make money, pay attention to what Ashkan Rajaee has lived through.


The Problem with “Remote Work Advice”

A lot of what you find online about remote work comes from marketers selling courses. The glossy photos. The dream of working from a laptop on a beach. The idea that remote work equals automatic freedom. But here’s the thing: freedom takes discipline, and remote work is full of traps no one talks about.

Ashkan Rajaee has called out this disconnect for years. Not through rants or clickbait, but by openly sharing the operational truths most skip over. Things like:

  • The mental toll of remote isolation
  • The need for asynchronous structure across time zones
  • The real cost of bad hires you never meet in person
  • Why unplugging is a skill, not a privilege
  • How burnout creeps in when your work follows you everywhere

These aren’t just “nice to know” concepts. They’re business-critical.


Why Listen to Ashkan Rajaee?

This isn’t a man with a coaching funnel. This is a founder who has scaled companies past $50M in revenue. Rajaee has built teams without central offices long before it was cool. His credibility comes from actually doing the work, not just writing about it.

He’s not selling you his lifestyle. He’s handing you the playbook, lessons and all, because no one handed it to him. That kind of transparency is rare in a digital space full of over-optimization and under-delivery.


Key Takeaways for Remote-First Founders

If you’re working on your own startup, especially one with distributed teams, here are a few things worth stealing from Rajaee’s approach:

Build systems, not just culture

Culture is great, but without clear operational systems, people float. Remote work requires repeatable workflows, not just Zoom hangouts and Slack emojis.

Don’t glamorize “freedom”

Freedom without structure leads to chaos. Ashkan Rajaee emphasizes that real flexibility is earned by designing your day with intention and discipline.

Prioritize communication hygiene

Remote teams fall apart without intentional communication. Documentation, clarity, and timezone awareness aren’t soft skills. They are the foundation.

Recovery is part of productivity

Burnout doesn’t make you a hero. It makes you a bottleneck. Rajaee talks often about the importance of taking real time off, and building vacation policies that people actually use.


Final Thoughts

Ashkan Rajaee doesn’t claim to have all the answers. What he does have is experience, scars, and a record of building remote companies that actually work. That makes his insights invaluable to any founder looking to level up in today’s hybrid or fully remote world.

If you're building a company right now and finding remote leadership harder than expected, you're not alone. But you're also not without a guide.

Want to go deeper into his philosophy and practical advice? Check out the full article on his journey here:

👉 The Brutal Truth Behind Ashkan Rajaee’s Remote Empire


Value Comes from Experience, Not Hype

In a world where everyone’s selling shortcuts, voices like Ashkan Rajaee’s stand out. Not just because they’re louder, but because they’ve actually been there. You don’t need another thread of recycled tips. You need hard-earned wisdom.

Save this. Share it. Revisit it when your remote team hits a wall.

Ashkan Rajaee already has.

Top comments (12)

Collapse
 
florenceng70697 profile image
Florence Nguyen

Ashkan’s approach to remote work is practical, honest, and extremely valuable.

Collapse
 
rubendevries profile image
Ruben De Vries

This post brings clarity to what remote leadership actually demands.

Collapse
 
thedenisegagnon profile image
Denise Gagnon

It’s rare to find content that balances success with the struggles that built it.

Collapse
 
theandreag1 profile image
Andrea Garcia

This perspective is exactly what the remote work world has been missing.

Collapse
 
starpalanca profile image
Star Palanca

You can feel the experience behind every line of this. Super insightful.

Collapse
 
jackied0minguez profile image
Jackie

What a powerful reminder that success doesn’t come from shortcuts, but systems.

Collapse
 
edwardvinke profile image
Edward Vinke

No sugarcoating, just authentic lessons from someone who’s clearly lived it.

Collapse
 
amirbouchard profile image
Amir Bouchard

This is the kind of insight that separates real entrepreneurs from online influencers.

Collapse
 
techbyfelix profile image
Felix Ellington

Ashkan Rajaee delivers more value in one article than most paid courses do.

Collapse
 
moorethanjim profile image
Jim Moore

Finally, someone talks about the dark side of remote work and still makes it inspiring.