My First Million – "If You Want a Rich Life, Watch This Before 2026"

Date: December 31, 2025
Hosts: Sam Parr and Shaan Puri
Guest: Jesse Itzler
Main Theme:
How to design and live a "rich" life—one defined by memorable experiences and personal intention—by implementing Jesse Itzler’s practical system for planning your year, balancing ambition with fulfillment, and moving from reactive living to proactive, meaningful action.

Episode Overview

In this energized, idea-packed episode, Shaan Puri sits down with serial entrepreneur and adventurer Jesse Itzler at Jesse's house to uncover Jesse’s step-by-step system for planning a remarkable year. Jesse, famed for selling a jet company to Warren Buffett, co-founding Zico Coconut Water, and living an epic, adventure-filled life, shares candid advice and tools to help anyone intentionally craft a richer, more memorable life in 2026. The conversation covers confronting the time-suck of daily obligations, clearing physical and mental clutter, annual self-audits, planning signature adventures (the Japanese “misogi”), the power of handwritten thank-you notes, and surrounding yourself with like-minded people.

Key Discussion Points & Insights

1. The “Rich Life” Philosophy

• Jesse isn't just admired for his financial success but for his intentional, joy-driven life.
• Quote: "We don't lack time, we lack a system." (Sean, 00:19)
• The episode's central question: How can anyone architect a life that doesn't just happen on autopilot but is instead a highlight reel of self-chosen adventures, growth, and fulfillment?

2. Playing Life on Offense, Not Defense

• Jesse: Most people default to letting work and other people’s priorities fill their calendar, then squeeze life in the cracks.
• Instead, life should go first—then work gets scheduled around it.
• Quote: “We tend to play life on defense. Like, our calendars fill up with other people's requests... before you know it, what do we have to show for a whole year?” (Jesse, 00:51, repeated for emphasis at 02:41)

3. Step 1: Get "Light" (Declutter for Momentum)

• Action: Begin the year by eliminating unnecessary baggage—physical, digital, and mental.
• Examples:
  • Delete unused apps, cancel wasteful subscriptions, donate unworn clothes, clean workspace, organize car, reach “inbox zero”.
• Psychological Impact: Small early wins build momentum and foster a sense of readiness and control.
• Quote: “Just doing the simplest action gave me momentum... I just cleaned out the cup holder, the simplest possible action. And right away, I was, like. Felt a little lighter...” (Sean, 07:44)
• Jesse’s Rule: If you’re 50/50 about keeping something, give it away; “Someone needs it more than me.” (Jesse, 10:29)
• Timestamp: [06:02 - 11:26] – Detailed ‘getting light’ strategies

4. Step 2: Year-End Review & 'Life Audit'

• Like any good business, close out the year with a review: What worked? What didn’t?
• Life Audit Exercise:
  • Imagine your life as a blender: finances, fitness, relationships, career, family, etc.
  • Rate your overall “happiness” on a scale of 1–10.
  • Identify the 2-3 areas (your “pain points”) that are dragging your score down—these are your focus for next year.
• Quote: “B minus is good, but you don't want to go through life as a B minus.” (Jesse, 15:27)
• Review your highlights (“calendar as highlight reel”), document memorable moments, and notice gaps.
• Thankfulness:
  • Write handwritten letters to people who enriched your year. This is for gratitude, networking, and solidifying relationships.
  • “Ink stain in the brain”—handwritten notes stick with people. (Sean/Jesse, 21:03)
• Timestamp: [11:31 - 22:52] – Annual review and gratitude rituals

5. Step 3: Proactive Planning for 2026—Jesse’s System

• Sequence Matters: Don’t jump to resolutions. Start with clearing clutter, self-auditing, and positive reflection to build the foundation.
• Quote: “Anyone can have a good year... Who the wants to have an okay year? ...Our goal is to get you excited about this.” (Jesse, 23:22)
• Jesse’s Three Planning Anchors:
  1. Misogi (Signature Challenge):
     • Do ONE “year-defining” thing—a big challenge or adventure that takes you way beyond your comfort zone. “If you can do that from now until you’re 87...that’s 50 monumental things you’ve accomplished.” (Jesse, 26:48)
  2. Kevin’s Rule (Mini Adventure, Every Other Month):
     • Every two months, plan something you normally wouldn’t do—trips, creative experiments, unique experiences.
     • “If you can’t take one day every six weeks to do something for yourself…what are we doing?” (Jesse, 28:10)
  3. “Big Rocks” (Pre-Schedule Important Personal Events):
     • Before filling your calendar with work, lock in family milestones, travel, and moments of connection.
     • “Work will always be there. I’m just planning me before my work.” (Jesse, 23:54)
  4. One New Winning Habit Each Quarter:
     • Rather than failed resolutions, pick one positive habit to layer in every three months. Over a year or two, they accumulate powerfully.
     • Examples: Drink 100oz water daily, meditate ten minutes, never late for meetings.

6. Mindset: What Trips Most People Up?

• Trap: “More isn’t better; better is better.”
  • Overwhelm comes from setting too many goals. Focus on one clear, meaningful target at a time.
• Balance is Yearly, Not Daily:
  • Don’t expect to have perfect work-life harmony every day; look at your life in “seasons.”
• Energy Allocation:
  • At week’s start, ask: "Where do I want to put my energy?"
  • Use an evening routine to map out the next day’s priorities instead of winging it.

7. The "Eight Boxes" (Life To-Do List) System

• Draw eight boxes/categories that matter most: Adventure, Travel, Marriage, Health/Fitness, Kids, Business, Family, Personal Finance, etc.
• Fill each with dreams, goals, and long-term aspirations.
• Review regularly; when inspiration or opportunity arises, pull from these boxes to shape your year.
• Quote: “It’s out of my head and it lives... it gives me a blueprint for where I’m going.” (Jesse, 44:56)
• Mental Model: This is the “Life Resume” – as important, or more, than your professional one.

8. Building Your Crew & The Power of Community

• You may not have close friends for adventures right away; share your goals, take initiative, and like-minded people will appear—often later in life.
• Sean: “That might be one of my things I put on here is like build a crew to do these things with.” (48:30)
• Involve your network, family, and community to enrich and compound your experiences.

9. How to Stay Ambitious Without Feeling Rushed

• For “one-way door projects” (books, big launches), don’t rush—finish, then make it 10% better.
• Quote: “If I wrote a half-assed version of that book, I would have beaten myself up forever. So that’s how I feel about those kinds [of projects].” (Jesse, 52:02)

Notable Quotes (with Timestamps and Attribution)

• “We don't lack time, we lack a system.” (Sean, 00:19)
• “We tend to play life on defense... what do we have to show for a whole year?” (Jesse, 00:51/02:41)
• “I've always thought of myself as the CEO of my company, but not the CEO of my life.” (Sean, 02:30)
• “If there’s a jump ball, 50/50… then someone needs it more than me.” (Jesse, 10:29)
• “B minus is good, but you don't want to go through life as a B minus.” (Jesse, 15:27)
• “You should be able to, at the end of each year, define that year by something you did—a Misogi.” (Jesse, 26:48)
• "More isn't better. Better is better." (Jesse, 38:05)
• "You need a system. If you wait, your calendar is going to fill up and other people are going to determine where your energy goes." (Jesse, 41:24)
• “Ink stain in the brain.” (Sean, 21:03) – on the memorable impact of handwritten letters
• “This isn’t about planning the most perfect year; it’s about planning something that you’re excited about.” (Jesse, 31:37)
• “I have this like creative bucket list. So for me, one of my... probably where you have adventure for me would be creative projects...” (Sean, 48:55)

Timestamps for Key Segments

• Jesse’s “Get Light” Method: [06:02 – 11:26]
• Life Audit & Annual Review: [11:31 – 17:56]
• Writing Thank You Notes: [17:56 – 21:54]
• Planning a ‘Signature Year’ - Misogi/Kevin’s Rule: [23:22 – 32:15]
• How to Build a Life Resume / Eight Boxes: [42:37 – 48:55]
• Building Your Crew & Community: [47:32 – 48:55]
• Creative Projects, Avoiding Life Overwhelm, and Reflection: [48:53 – 52:12]

Closing Thoughts

Jesse’s system—rooted in trial, error, and lived experience—puts adventure, intentionality, and connection above mere busyness. “Richness” comes from designing your year around purposefully chosen milestones, relationships, and new habits, then letting your work and obligations fill in around them. No matter your resources or stage of life, the essence is to act, review, and play aggressively—because nobody wants to look back and realize they lived a “B minus life.”

Takeaway:
If you want a richer, more intentional year, get light, close out your year with reflection and gratitude, proactively schedule big challenges and mini-adventures, and create living systems—on paper and in habits—that make this possible. “You need a system. If you wait, your calendar is going to fill up and other people are going to determine where your energy goes.” (Jesse, 41:24)

Listen to this episode for the full energy, stories, and practical examples that can turn your 2026 into a year you’ll never forget.