Founder Mode Episode 18 - Perfect Days With Your Ride-Or-Dies

Jason and I recently talked about how to manage your schedule as a founder. We talked about taking smart risks. We talked about why strong teams matter. Here’s my personal take on these topics from our chat.

How I Manage My Schedule as a Founder

As a founder, scheduling is key to my productivity. I rely on a system of Executive Assistants (EAs) to help me organize my day. I like to wake up at 5 AM. I begin my day with meetings. I often meet with my East Coast colleagues. I save my afternoons for deep tasks and workouts that can be done anytime.

Jason’s schedule is different. He does deep work in the morning. Then, he schedules meetings for the afternoon. The key lesson? Tailor your schedule around when you have the most energy.

My advice on scheduling:

“Start with a blank calendar and map out your ideal day. You won’t achieve perfection daily, but striving toward it keeps you focused and efficient.”

Why I Believe in Taking Bold Risks

Lots of big companies set rules that hold back creativity. This can make people less eager to take action. Personally, I prefer pushing the boundaries. As founders, we often need to take bold, calculated risks to succeed.

One example I always remember is Fred Smith, the founder of FedEx. He couldn’t pay the fuel bill, so he went to Las Vegas. He gambled the money, won big, and saved the company. For me, taking smart risks shows the mindset of a founder.

My view on risk-taking:

“The founders who built big companies took significant risks. Being a founder means pushing limits and sometimes making bold moves.”

Health Is the Foundation of Everything Else

Health is my foundation for success. Jason got an important tip from his physical therapist:

“You come into this world and leave with only one thing—your body.”

Good health is essential. Without it, professional success means little. Always prioritize taking care of yourself first.

My Current Tech and Non-Tech Favorites

As Jason checks out the Meta Ray-Ban smart glasses, I’m using the Tune Up Fitness massage balls. They’ve helped with mobility and stress relief. My curiosity and use of tech and non-tech tools help keep my mind sharp and balanced.

Building My “Boomer Ride” Team

I just talked about hiring people I’ve worked with in the past. I call this “Boomer Rides.” It mixes “boomerang” and “ride-or-die.” We don’t focus on skills when thinking about bringing someone back. I already know what they can do. It’s more about understanding where we both are in life and if it’s the right fit again.

Past success doesn’t ensure future success. It’s essential to reassess and ensure you’re still aligned.

Key Takeaways:

Set Your Ideal Schedule: Start each week with a goal, then change it if necessary.
Take Bold Risks: Smart risks can shape your path as a founder.
Put Health First: Good health is crucial for lasting success.
Try New Tools: Experimenting helps keep your mind sharp.
Build and Reassess Your Team: Find your “Boomer Rides” and review their fit often.

Final Thoughts

Setting clear goals is key to founder success. Work on your schedule, focus on your health, build your team, and be open to risks. My experience proves this. Plan your ideal week. Challenge yourself in a smart way. Stay close to trusted friends and family. Always prioritize your health.

These strategies are key for lasting growth as a founder.

“Define your perfect week, take calculated risks, keep your Boomer Rides close, and never underestimate the power of health or smart scheduling.”

— Kevin Henrikson

🎧 Listen to Episode 18 here: