MFM #167: Answering Your Questions On Investments, Businesses and Life

About this video

Sam and Shaan answer audience questions about their personal investments, philosophy on hiring friends, biggest insecurities, and future plans. They discuss their portfolios (Sam favors index funds and conservative investing; Shaan takes bigger bets in crypto and startups), their experience running a rolling fund, why they haven’t started new companies despite opportunities, and their approach to balancing side projects with full-time work.

Key takeaways

• Sam keeps roughly 90% of his net worth in index funds (primarily S&P 500), with smaller allocations to individual stocks (HubSpot, Airbnb) and angel investments; Shaan takes a more aggressive approach with significant crypto holdings and larger startup bets, inspired by investors like Chris Sacca who go ‘all in’ on winners
• Hiring competent friends can work if you establish clear boundaries upfront about the business-vs-friendship dynamic and ensure they perform; mixing incompetent friends with business typically damages relationships and should be avoided
• Sam prioritizes delivering results over strict hours at his employer (Twitch), unlocking time for side projects (podcast, newsletter, angel fund) through efficiency, hiring others, and explicit agreements with leadership; Shaan emphasizes not mixing friendships with employment and maintaining professional distance
• Both hosts are cautious about starting new companies because the opportunity cost is high—each person can realistically do it only 3-4 times in their life; Sam is focused on his current role at HubSpot while considering a passion project he never wants to sell; Shaan found his long-term project in the podcast and content creation after initially pursuing other ventures
• Shaan acknowledges admiring ambitious figures (including controversial historical leaders) for their ability to mobilize people and manifest ideas, separate from moral judgment of their actions; both hosts grapple with insecurities around intelligence, impact, and whether their work matters relative to mission-driven founders

Episode details: published April 5, 2021 · 6.4K views · 52:59 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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