Strategically Broke Year

Shaan's philosophy of being "strategically broke" - intentionally living on minimal income to maximize freedom, learning, and adventure in your early career.

The decision to be strategically broke

• Graduated college with a $120,000/year job in a boring industry he didn't care about
• Quit after a month and a half to pursue a sushi restaurant business idea (Sabi Sushi - "the Chipotle of sushi")
• Had $25,000 prize money from a business plan competition split between 3 people = $8,000 each for a year
• Didn't even know how much life actually costs as a college kid - everything was just provided
• Made a conscious choice: either wake up everyday worried about money, or commit to spending the year "strategically broke"

The trade-off framework

• Looked at friends who were investment bankers: "money rich, time poor"
• Decided to flip it: be "money poor" but rich in other areas
• If making 10-12x less money, needed to be learning 12x more than entry-level jobs
• Entry-level jobs don't teach you that much - you learn the same task repeatedly, not a wide breadth of skills

What being "strategically broke" optimized for

1. Time richness - freedom and flexibility of schedule
2. Adventure richness - travel with friends, do fun stuff
3. Learning richness - learn 12x more than a traditional job would teach

The learning advantage

• Learned about diverse topics: sushi, restaurant operations, margins, P&Ls
• Pitched investors, negotiated leases, understood real estate
• Discovered liquor license hack: licenses are on public file with lease amounts, used this intel in negotiations
• Core skills: sales, marketing, brand building, design, video editing, blogging
• Philosophy: "high action" - shit ton of action, DIY everything, hiring, firing, learn as many lessons as possible

Living on minimum

• Slept on air mattress
• Hammered a garbage bag to the wall with a nail (no proper trash setup)
• Drank from a free Gatorade cooler from a gym
• Made side money coaching basketball at a school for autistic children
• Tutored college students in stats for $25-30/hour
• Calculated the minimum amount needed to earn for max freedom

The key insight

• Money is a tool for freedom
• When you're young, don't optimize for stacking dollars in the bank account
• Instead: optimize for freedom, learning, adventure, and fun
• Calculate the minimum money needed to do that
• Still applies this principle to companies: calculate minimum funding needed just to get to the next milestone (like 1,000 customers who love the product)

Validation from successful people

• Dharmesh (billionaire founder of HubSpot) said the same thing about his first business
• Did random stuff not knowing anything - first business was successful
• Second business he thought he knew the "proper ways" - screwed it up
• Lesson: "Just because I was ignorant doesn't mean I was wrong"
• You might actually get a bunch of things right when making it up as you go