Ep 224: Lazy but Smart: How Kira Shishkin Creates Freedom Through Systems

In this episode of the Lazy Entrepreneur Podcast, Kristy sits down with Kira Shishkin, CEO of informed.now and a seasoned serial entrepreneur. Kira has built four companies across different industries, including crypto infrastructure, publishing, and consumer tech. With a background that spans Ukraine, Israel, and the United States, he brings a truly global perspective on resilience, leadership, and building businesses that last.

Kira shares how he has applied the principles of what he calls “lazy entrepreneurship”—not about avoiding work, but about creating efficiency and freedom through smart systems, delegation, and automation. He explains why mastering tasks before delegating them makes hiring more effective, how to communicate clearly within international teams, and why prioritization is an essential daily discipline for entrepreneurs.

This conversation is packed with practical advice for entrepreneurs who want to scale their business without burning out and who are ready to shift from doing everything themselves to building smarter, sustainable systems.

Key Takeaways:

• Master before you delegate: Learn the task yourself so you can give clear feedback and evaluate success.
• Hire early and wisely: The right hires accelerate growth, while the wrong ones slow it down.
• Prioritization is a discipline: Always order your to-do list by importance, not randomness.
• Communication is non-negotiable: Build a culture of proactive honesty, especially in international teams.
• Systems create freedom: Use technology and processes to make your business run without constant founder oversight.
  
  

👉 Connect with Kira Shishkin:

https://l.informed.now/kira  

https://informed.now/

To automate LinkedIn outreach, you can use Kira's partner status with Dripify: https://try.dripify.com/kira