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How I Invest with David Weisburd
How I Invest with David Weisburd•August 25, 2025

E204: Going All In: The Risks and Rewards of Concentrated Investing

Here's a 2-sentence description for the episode: Rafael, the founder of Cross Capital, discusses his investment strategy focused on backing software businesses across the Americas, with a particular emphasis on the Brazilian tech ecosystem and a concentrated portfolio approach. The episode explores the unique characteristics of growth equity investing, the potential for market-leading companies to compound value, and the emerging role of AI in transforming regulated industries.
Solo Entrepreneurs
Business News Analysis
Venture Capital
Rafael Alvarez
David Chen
Paul Allen
Tyler Soson
Warren Buffett

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Compelling StoriesPremium
  • Strategies & FrameworksPremium
  • Thought-Provoking QuotesPremium
  • Statistics & Facts
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Similar StrategiesPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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Podcast Summary

In this episode, Rafael shares his journey from top-tier growth equity firms to launching Across Capital, a concentrated fund focused on software businesses across the Americas. He dives deep into Brazil's remarkable fintech ecosystem (02:20), explaining how hyperinflation and progressive central banking created fertile ground for innovation, while exploring his concentrated portfolio strategy of just 10 companies that forces "ruthless prioritization" (07:02). Rafael also discusses why growth equity differs from venture capital in prioritizing consistency over power laws, how his firm's QiTech investment became a potential fund returner (10:54), and the compounding advantages of market leaders in an AI-driven world.

Speakers

Rafael Alvarez

Managing Partner at Across Capital, previously investment professional at Summit Partners and Vulcan Capital (Paul Allen's investment arm). Brazilian-born investor focused on cross-border technology investments across the Americas, with a concentrated 10-company portfolio strategy that has generated multiple fund-returner outcomes.

David Chen (Host)

Host of the How I Invest podcast, conducting in-depth conversations with leading investors and entrepreneurs. Known for exploring investment strategies and career insights with industry professionals across venture capital and growth equity.

Key Takeaways

Build High-Conviction, Concentrated Portfolios

Limit your portfolio to 10 companies maximum—concentration forces ruthless prioritization and deeper diligence. When you only get 10 shots, you lean into your edge and drive meaningful partnerships rather than buying call options. (07:07) This scarcity mindset changes how you source, engage, and select investments, creating powerful alignment with entrepreneurs.

Master the 17-Month Relationship Strategy

Invest in relationship-building 17 months before making an investment decision. This extended courtship allows you to earn your seat at the table with entrepreneurs and build conviction to move with efficiency and speed when they're ready to transact. (09:08) Focus on 30 opportunities per quarter in your middle funnel to identify your 2-4 annual investments.

Institutionalize Your "What Really Matters" Framework

Create a systematic process where every investment memo includes a slide limiting critical success factors to no more than five key drivers. (17:02) When re-underwriting investments, objectively assess performance against these specific metrics using quantitative measures wherever possible. This prevents retrofitting narratives and maintains disciplined decision-making.

Size Positions Based on Conviction, Not Diversification

Don't default to equal-weighted positions—increase allocation to your highest-conviction bets over time. QiTech started at 12.5% allocation and grew to 20% as the company consistently beat projections. (15:08) Back your winners when they demonstrate superior risk-adjusted returns rather than spreading capital thin across mediocre opportunities.

Focus on Consistency Over Power Laws in Growth Equity

Target consistent 3-5X returns with strong downside protection rather than chasing binary 10-30X outcomes that could zero out. Build portfolios where capital impairment risk is minimized through stage selection, deal structure, and company IP analysis. (13:03) This approach enables concentrated portfolios while preserving upside potential through proper position sizing.

Compelling Stories

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Strategies & Frameworks

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Thought-Provoking Quotes

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Statistics & Facts

  1. QiTech grew 200% plus year over year with EBITDA margins in excess of 50%. (05:15)
  2. PIX (real-time payments rail) has achieved penetration of 80% plus of the adult population in Brazil. (03:39)
  3. QiTech represents a 20% position in Across Capital's fund and was valued close to $2 billion in the latest round, up from their initial $300 million investment. (11:06)

Additional Context

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Key Takeaways Table

Available with a Plus subscription

Critical Analysis

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Similar Strategies

Available with a Plus subscription

Books & Articles Mentioned

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Products, Tools & Software Mentioned

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