Lazy but Smart: How Kira Shishkin Creates Freedom Through Systems
In today’s fast-paced world of startups and scaling companies, the word “hustle” often gets glorified. But what if success didn’t come from working harder, but from working smarter?
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That’s exactly the philosophy of Kira Shishkin, CEO of Informed, a consumer platform designed to help people navigate misinformation and reclaim the dignity of being truly informed. A serial entrepreneur, Kira has built four companies across industries—crypto infrastructure, publishing, marketplace platforms, and now consumer tech.
Born in Ukraine, raised in Israel, and now based in the United States, Kira’s global background gives his a unique lens on entrepreneurship, leadership, and building teams across cultures.
In this podcast article, we’ll dive into the key lessons from his journey, including:
Why delegation and hiring are the most leveraged decisions for entrepreneurs.
How to communicate effectively across international teams.
The importance of prioritization and system-building.
Why “lazy entrepreneurship” is actually the smart path to freedom.
The Entrepreneurial Journey of Kira Shishkin
Kira describes his career as a blend of experimentation, resilience, and adaptability. He has successfully navigated industries as diverse as crypto, publishing, and enterprise technology incubation.
But his fourth venture, Informed, feels different. It’s his first consumer-facing company, and it reflects his deeper mission: helping people cut through noise and misinformation in a world where attention is constantly hijacked.
His entrepreneurial story underscores a powerful truth: success in business isn’t linear. Each venture built the foundation for the next, adding new skills and lessons to his toolkit.
Why Delegation is the Most Leveraged Decision an Entrepreneur Can Make
One of Kira’s biggest insights is that hiring the right people is the single most leveraged decision an entrepreneur can make.
He emphasizes two important rules:
Master a task before delegating it.
“I try to give away tasks I’ve already mastered,” Kira explained. “If you don’t know what good looks like, how can you evaluate someone else’s work?”Hire for clarity, not mystery.
Too often, founders hire for tasks they don’t yet understand. This creates blind spots, frustration, and wasted resources. Instead, entrepreneurs should learn enough about a process to give meaningful feedback before bringing someone on board.
The result? Delegation becomes a growth multiplier instead of a liability.
Communication in International Teams: A Non-Negotiable Skill
With a team spread across multiple countries—including the Philippines—Kira has firsthand experience with the challenges of global collaboration.
For him, the non-negotiable in communication is simple: proactive honesty.
He values team members who speak up immediately when something doesn’t make sense or when they hit a roadblock. In his words:
“If there’s an issue slowing you down, don’t wait—escalate it right away.”
Kira also points out that communication challenges aren’t just about language barriers. They often stem from cultural differences in how people are taught to voice concerns.
For example, in some cultures (like the Philippines), team members may hesitate to raise issues out of politeness or fear of “bothering” others. Great leaders recognize this and create a safe space for proactive communication.
Prioritization: The Habit That Shapes Productivity
One of Kira’s most practical pieces of advice for entrepreneurs is about prioritization.
He doesn’t just make to-do lists—he makes ordered lists.
“Every time you make a list, put it in order of importance. Don’t just write tasks down randomly. Force yourself to rank them.”
This micro-habit ensures that even on the busiest days, the most important tasks get done first. It also creates clarity for his team, who can see where priorities truly lie.
Lazy Entrepreneurship: Why Working Smarter Creates Freedom
Kira jokes that he builds his businesses in “lazy ways.” But his version of laziness isn’t about avoiding work—it’s about creating efficiency and freedom.
He defines lazy entrepreneurship through three pillars:
Systems Over Supervision
He builds autonomous systems that don’t depend on his presence. From marketing to operations, he creates processes that allow his team to run independently—and even onboard new hires without his involvement.Technology as a Multiplier
He doesn’t just settle for the first tool he finds. Instead, he shops around for the best software, tests multiple options, and invests in the one that creates the most automation and efficiency.
For example, he spent months testing LinkedIn automation tools before finding one that truly worked for his team. That patience turned into huge long-term savings in time and stress.Hiring Early
Instead of waiting until the business hits “success,” Kira recommends hiring as soon as possible—because the right hires accelerate success instead of slowing it down.
Lazy entrepreneurship, in his words, is not about doing nothing. It’s about removing yourself from low-value tasks so you can focus on vision, growth, and freedom.
Handling Bad Hires and Wrong Fits
Of course, not every hire works out. Kira has faced situations where talented people simply weren’t the right fit for the task.
His approach? Decide quickly whether to let them go or reassign them to a role better suited to their strengths.
“Sometimes it’s not the wrong person—it’s the wrong task.”
This mindset allows his to retain great talent while protecting the business from prolonged mismatches.
Anticipating Needs vs. Reacting in Panic
One of the biggest lessons Kira shared was the value of anticipating needs.
Whenever possible, he shops around for solutions before they become urgent. That way, he avoids locking into long-term contracts with the wrong tools or vendors.
But when emergencies arise, he recommends short-term commitments and keeping a running list of what you wish your current tools or systems did better. That way, you can upgrade intelligently when the time is right.
Key Takeaways from Kira Shishkin
Here are the biggest lessons entrepreneurs can apply today:
Master before you delegate. Know what good looks like so you can evaluate effectively.
Prioritize communication. Especially in international teams, proactive honesty is everything.
Always order your to-do list. Prioritization is a daily discipline.
Build systems that don’t require you. Freedom comes from autonomy.
Shop around for tools. The wrong tech can waste months; the right one can save years.
Hire early and smart. Great hires accelerate success—bad hires stall it.
Anticipate, don’t react. Plan ahead so you’re not forced into poor decisions.
Kira Shishkin’s story proves that entrepreneurship isn’t about doing everything yourself—it’s about creating systems, empowering people, and making smart decisions about where your time goes.
From Ukraine to Israel to the U.S., from publishing to crypto to consumer tech, her journey is a masterclass in resilience and adaptability. And his philosophy of “lazy entrepreneurship” reminds us that true success comes not from endless hustle, but from building smarter.
If you want to learn more about Kira and his current mission, visit Informed or connect with him directly on LinkedIn.
Because at the end of the day, entrepreneurship is not about being busy—it’s about building businesses that give you back your time, freedom, and impact.
Connect with Kira on LinkedIn.
