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Quick Q&A Setup with Listener Questions
Sam explains that Shaan is out for surgery, so he is running a short 10-15 minute Q&A. The questions come from listeners and Sam's Twitter followers.
- •Shaan is out for surgery, and Sam jokes it is a nose job
- •Format is a quick 10-15 minute Q&A
- •Questions were gathered from listeners and Twitter fans
- •Sam opens with a story about his wife's drawer of coupons and a Costco trip
Becoming a Dad and Fearing a Spoiled Child
Sam says his daughter is due November 1. He found reassurance about her physical wellbeing in the story of Sacagawea carrying her baby across America. His main fear is raising a spoiled kid or a drug addict, and he is thinking about how to withhold things from her to build grit.
- •Daughter is due November 1
- •Reading about Sacagawea carrying a baby eased his worries about her physical wellbeing
- •His biggest fear is a spoiled, indulgent child who won't work hard
- •Current thinking is to pay only for tuition and medical care and give nothing beyond that
- •He cites Rockefeller's wife, who said her joy was withholding things from her children to make them stronger
What Changed After Getting Rich: Confidence, Not Stuff
Sam recalls years on low salaries before selling his first company. He advises against big purchases in the first year or two and compares the effect to how amputees return to baseline happiness. The biggest change for him was confidence, though he still fears going broke.
- •Salary was $20,000 a year for four years before rising to $150,000 and then $350,000
- •He bought real estate and a fancy car early on and says that brings close to no happiness
- •He advises not buying anything crazy in the first year or two after a windfall
- •The amputee study illustrates how happiness returns to baseline
- •His confidence in starting and finishing things soared, but he still has fears about going broke that he works on with his therapist
Monthly Expenses and Lifestyle Details
Sam breaks down his spending, which rose from about $10-15K a month to about $20-25K. He lists the mortgage, summer New York rent, paid-off cars, and a low-key lifestyle. Extras include business class flights because he hates flying, and he budgets the rest, including using coupons.
- •Spending went from $10-15K to roughly $20-25K a month
- •Austin home cost $900,000, with mortgage and taxes around $5-6K a month
- •Summer rental in New York runs $10-13K
- •Two paid-off cars, a $120-a-week cleaner, and about $1,000 a month on gym and doctors
- •Hates flying, so he drives or flies business class; his house cost $30,000 to furnish
Alternative Business Idea: A Research and Data Company
Sam says that if not for Hampton he would have built a research or database company, guided by his Ikigai framework. He loves tracking data and deconstructing companies but couldn't find a go-to-market plan or a reason people would pay. He mentions CB Insights and PitchBook as models and says a non-compete kept him out of a business news email.
- •Ikigai is a Venn diagram of what the world wants, what it pays for, what you're good at, and what you love
- •He keeps databases, such as a CEO document tracking hundreds of biographies, and Notion pages deconstructing companies
- •He couldn't find a use case or go-to-market strategy for a research company
- •A one-year non-compete blocked a business news email
- •He sees research businesses as stodgy, under-innovated, and potentially big
The Most Painful Feedback Sam Received
Sam describes three painful moments. His friend Neville Madora told him to grow up after seeing a moldy towel and to stop asking intense questions. A media CEO dismissed The Hustle as never making over a million a year. Breakups also stung and left him sensitive to rejection.
- •Neville Madora, his best friend, gives him blunt but loving feedback
- •Neville called out his bachelor habits and his overly intense questions with new people
- •A media startup CEO said The Hustle would never top a million dollars a year, and Sam believed him for six months
- •Breakups still sting and motivate him to prove people wrong
- •Sam says he is sensitive to rejection
Overhyped Business Models: Web3, Newsletters, and Internet Fame
Sam calls NFT and Web3 businesses nonsense from inferior entrepreneurs. He says newsletters have become a treadmill in a far more competitive space, with much derivative content. He also finds chasing popularity on social media empty and says he regrets trying to become internet famous.
- •NFT and Web3 ventures are nonsense in his view
- •Newsletters are a treadmill and far more competitive than when he started, though he'd still start one
- •Content businesses are very hard to sustain for two or three years
- •Chasing social media popularity feels empty compared to building a company or focusing on family
Moving to San Francisco: Meetups and the Anti-MBA Book Club
Asked how to build a network when moving to San Francisco, Sam says moving to a big city young is great. He lived in SF for eight years and would still be there if not for his anger at the government. He attended many meetups and started a free book club called The Anti-MBA, which he advertised on Craigslist and meetup.com and which grew an email list of about 2,000.
- •Sam lived in SF for eight years and says it was 100% worth it
- •He went to huge numbers of meetups through meetup.com
- •The Anti-MBA book club read a book a month with an expert guest, and Sieva Kazinski was an early attendee
- •He posted his own notes online, growing a 2,000-person email list
- •The club came from his jealousy of people who attended schools like Stanford
How Sam Met Shaan Through a Cold Email
Sam tells how he met Shaan. He saw a TechCrunch article about Shaan's incubator, Monkey Inferno, and cold emailed him to host a Hustle Con pre-dinner at Shaan's office. Shaan said yes.
- •Hustle Con was Sam's event
- •A TechCrunch article showed Shaan's impressive Monkey Inferno office
- •Sam offered to handle food and cleanup in exchange for hosting the pre-dinner there
- •Shaan agreed and joined the dinner, which started their relationship
Finding Peers and Succeeding Together
Sam recommends cold emailing many people, focusing on ambitious peers rather than established figures. He says he and friends like Ryan Hoover helped each other and grew together. He admits it takes ten to fifteen years but says it's worth it, and that being around people making a dent in the universe was addictive.
- •Reach out to tons of people through cold email
- •Target peers who seem like they're going places, not those far ahead
- •Friends like Ryan Hoover, who started Product Hunt, were buddies before success
- •Help each other selflessly; his friends volunteered at his events and he helped them when they needed it
- •Building these relationships takes 10 to 15 years, and some friends were artists rather than financially successful
Going to Meetups Today and Wrapping Up
Sam describes a recent visit to San Francisco where a listener invited him and his wife to an AI meetup and hackathon. He found it magical to be around a group working on something non-mainstream and encourages going to such events. Shaan and Sam then wrap up the Q&A.
- •A fan recognized Sam at a farmers market and invited him to an AI meetup and hackathon
- •The event felt magical because of the group working on something non-mainstream
- •Sam encourages attending such events
- •They note other questions weren't answered and promise another Q&A later
Publisher timestamps
- 0:00Intro
- 0:42What is top of mind as you become a dad?
- 3:30What's the biggest difference in your lifestyle now that you're effing rich?
- 8:00What were your alternative business ideas if you didn’t do Hampton?Read this chapter
- 11:30What was the most painful thing someone told you and how did that change you?Read this chapter
- 15:00What’s one trendy business model you think is over-hyped?
- 17:00What did you do when you arrived [at SF] to start laying the foundation to meet interesting people and business builders?Read this chapter
