Overview

Wealth management reality: After selling Teachable for $250M, Ankur discovered private banking delivered underwhelming 6% returns (vs 13% S&P) with high fees, revealing that most financial advisors sell lifestyle perks rather than superior investment performance, potentially costing clients millions over a lifetime.

Tax optimization as alpha: While most investors won't significantly outperform indexes, substantial advantages can be gained through tax strategies like direct indexing (buying individual stocks for tax-loss harvesting) and Roth IRA optimization, which allowed Peter Thiel to turn $1,700 into billions tax-free.

Health as the new wealth: A major shift toward proactive wellness is occurring, with companies like Function Health ($100M revenue in 2-3 years) offering comprehensive testing and personalized plans, while alternative food systems (like Amish farm networks) are gaining popularity among health-conscious consumers.

Sports as investment and community: Ankur invested in the Chennai Super Kings cricket team (valued near $1B) while finding community through basketball leagues, highlighting how sports serve both as investment vehicles with multiple revenue streams and as crucial social connectors for adults.

Content

Personal Finance and Background

Ankur criticizes common sources of financial advice (parents, TV, salespeople) as unreliable and shares his personal experiences with making money through internet ventures.

Ankur's background includes:

- Making his first millions at age 20 through viral Facebook apps (personality quizzes) - Founding Teachable, an online course platform - Selling Teachable for around $250 million when he was around 32 years old - Earning approximately $100 million from the sale

Before selling Teachable, Ankur was financially modest, paying himself only a $150,000 salary while living in New York.

After selling Teachable, Ankur conducted an A/B test with his money:

- Gave half to Goldman Sachs to invest - Invested the other half himself to learn about investing

Private Banking Experience

Ankur's experience with private banking was underwhelming:

- Portfolio averaged only 6% return compared to S&P's 13% - High fees (50-120 basis points) for mostly vanilla, index-based investments - Inappropriate investment strategies for a young investor, like excessive fixed income allocations

He discovered private banking primarily sells lifestyle and status, not just financial services:

- Perks include concierge services like event tickets and dinners - Fee structure means clients don't feel the direct pain of high costs - Over a lifetime, fees could potentially reduce portfolio by millions of dollars

Ankur concluded that flat fee financial advice is potentially more cost-effective, and while financial advisors can provide value, percentage-based fees become increasingly inefficient at higher wealth levels.

Investment and Tax Optimization Strategies

Ankur's main investment thesis is that most people won't achieve significantly differentiated investment performance, and indexing (like S&P 500) can be a solid strategy.

He believes tax optimization is where real "alpha" (advantage) can be found for investors, highlighting several strategies:

Direct Indexing Strategy:

- Involves buying individual stocks in an index instead of a fund - Allows for tax loss harvesting by selling losing positions - Can potentially generate 30-40% usable tax losses - Example: Invested $250K, generated $16,000 in tax loss harvesting while maintaining same performance as S&P index

Tax Efficiency Recommendations for high-tax-bracket individuals:

- Municipal funds (no federal taxes) - Treasury bonds (no state/local taxes) - State-specific municipal funds - A tax-optimized approach can increase yield from 3-4% to 6-7%

Ankur notes that for lower-income individuals (e.g., $50K revenue), focus should be on increasing income rather than complex tax strategies, as tax optimization is most meaningful at higher income/investment levels.

Additional tax optimization techniques mentioned:

- Easy ACAT rollover between brokerages that generated significant tax losses - Potential tax advantages of municipal bonds over money market funds

Roth IRA Strategies

Background on Roth IRA:

- Created by William Roth for middle-class retirement savings - Allows after-tax contributions with tax-free growth - Originally had income limits (around $150,000)

Key Roth IRA features:

- Contributions are made with after-tax dollars - Investment growth is completely tax-free - Can withdraw contributions at any time - Full investment withdrawals allowed at 59.5 years old

Peter Thiel example:

- Placed PayPal founder shares in Roth IRA when valued low - Grew account to $5 billion - Will retire next year with no tax liability on the gains - Specifically turned $1,700 of founder's shares into $27-28 million in a Roth IRA

Mega Backdoor Roth IRA strategy:

- Allows contributing up to $70,000 annually through a 401k - Combined with regular Roth IRA, can contribute $77,000 per year - Potential to accumulate around $30 million by retirement if consistently invested - Considered a "loophole" that the IRS has attempted to legislate against

Historical context: 1970s top tax rates were around 80%, and government incentivized retirement savings by bringing tax revenue forward.

Health and Wellness Trends

The conversation shifts to discussing a major shift towards proactive wellness, moving away from the traditional reactive medical system.

Cultural attitudes are changing, with health and wellness becoming a status symbol, driven by influencers like Brian Johnson who promote advanced health optimization.

Companies like Function Health are rapidly growing (reaching $100M revenue in 2-3 years), offering:

- Comprehensive blood testing (30+ tests in a single draw) - Personalized action plans through concierge-style consultations - Focus on preventative lifestyle modifications rather than just treating symptoms

Improved healthcare infrastructure enables:

- Convenient blood testing options - Easy access to personal medical records - Simplified health data retrieval

Ankur shares his personal experience, discovering his biological age (40) is higher than his chronological age (37), with an upcoming consultation to provide a personalized health improvement strategy.

He believes people are increasingly unwell, particularly in the US, noting issues with fertility, gut health, and allergies.

Alternative Food Systems and Personal Health

Ankur discusses his approach to food sourcing:

- Purchases raw milk from an underground Amish farm network - Gets meat from an Amish farmer, finding it significantly better quality than typical U.S. grocery store meat - Describes the purchasing experience as feeling more authentic and almost like a "contraband" transaction - Notes feeling physically better when eating this food compared to standard U.S. food

He invested in a testosterone company, with a key criterion being the founder's physical fitness.

Ankur suggests potential business opportunities:

- A model combining health and aesthetic services - A concierge service focused on physical appearance and health optimization - Businesses that help people "break out" of the standard US food system

Travel and Credit Card Points

Ankur discusses strategies for using airline/credit card points:

- Mentions having approximately 7 million Amex points - Uses points strategically to buy tickets for family members - Finds points helpful for purchasing tickets parents would otherwise refuse

He's interested in creating a concierge service for booking travel using credit card points, noting that points can provide significant value beyond their dollar equivalent.

References a service called flightfox.com that helps book flights, which costs $20 per ticket and involves a human finding optimal flight options.

Briefly mentions the potential market for buying/selling miles, suggesting there's untapped value in this area.

AI and Personal Software Development

Ankur has a computer science background but hadn't coded extensively in 10+ years.

He recently re-engaged with coding through AI tools:

- Built internal workflow automation tools for his business - Currently developing a personal task management app for home-related tasks - Sees growing potential for AI-assisted personal software development

Home Management and Cultural Perspectives

The conversation explores the complexity of managing household responsibilities, especially for single individuals.

They discuss differences in home maintenance skills between those who grew up in the US versus outside the country:

- Noted stereotype about Americans being handy/self-reliant - Among some immigrant communities, having someone do repairs is seen as a status symbol - Shared an interesting detail about Home Depot's free monthly workshop attracting Indian families

Padel Sport Discussion

Padel is described as a tennis-like sport gaining popularity in New York:

- More athletic than pickleball - Played on a slightly smaller, wider tennis court with a back wall - Uses a depressurized tennis ball - Allows ball to bounce off back wall during play - Originated in Latin America and Europe, now expanding to the US

Court and market dynamics:

- New York courts cost around $300/hour and are frequently booked - US currently has approximately 1,000-2,000 courts (compared to 20,000 in Spain) - Seen as a potential business opportunity in tier two cities - Google trends show rapidly increasing interest

The sport uses a competitive rating system:

- Similar to ELO scoring - Ratings are entered by players after matches - Highly competitive, with players taking rankings very seriously - Powered by a company called Playtomic that has built a rating/tracking app

Padel attracts professional, competitive individuals in their 20s-40s and is seen as the speaker's second-largest expense after food in New York.

Adult Friendship and Sports Communities

Making friends as an adult, especially for fathers, can be challenging.

Strategies for meeting people include:

- Connecting through children's school networks - Participating in structured sports leagues - Finding community through shared activities

Ankur is deeply committed to a basketball league:

- Prepares extensively for weekly games - Uses AI camera footage for team analysis and coaching - Engages in detailed post-game discussions and strategy review

Cricket was a significant passion in Ankur's childhood (ages 8-14):

- Played internationally in his home country - Recently purchased a stake in a valuable cricket team

Sports Team Investment

Ankur invested high seven figures (personal contribution around 20%) in the Chennai Super Kings, an Indian cricket team:

- Team valuation is close to $1 billion - The team has won six championships in a 15-year-old league

Indian Premier League (IPL) insights:

- Third richest league globally - By TV rights per game, it's second only to the NFL - Total league revenue exceeds European soccer leagues - Cricket is India's dominant sport with massive market potential

Ankur views this as a stable investment unlikely to lose money, though not expected to generate tech startup-level returns.

He's interested in being an active owner and potentially drafting players and being directly involved in team management.

Sports Team Valuation and Business Strategy

The NBA is expanding, adding two new franchises (likely in Vegas and Seattle):

- New franchises expected to be valued around $5-6 billion - Significant value appreciation over time (e.g., Mavericks bought for ~$200 million, now worth much more)

Sports teams have multiple revenue streams:

- Media rights - Potential tax write-offs - Real estate opportunities - Potential sports betting integration - Capped player expenses

Two primary operational approaches for team owners:

1. Run profitably (likely means less competitive) 2. Spend heavily to win championships, hoping for high future sale value

The discussion concludes with observations about sports media rights and monetization strategies:

- Finding undervalued media rights is a critical business approach - U.S. sports leagues (especially NFL) are exceptionally skilled at monetizing viewership - U.S. leagues are more efficient at extracting financial value than European leagues

Ankur mentions hosting a conference sponsored by HubSpot and The Hustle, and provides his contact information: Twitter and Kerry.com for tax optimization.

How to retire with millions (and pay $0 taxes)