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«S&P 500 — для ленивых. Настоящие деньги в другом месте». Экс-глава M&A в Mail.ru Алексей Милевский

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The episode is an interview with Алексей Милевский, former Head of M&A at VK/Mail.ru Group and a startup investor (via his funds Multiplayer and M9 Capital). The discussion focuses less on “financial investing” and more on how deals are chosen and why, for him, investing is primarily an active, high-involvement, long-term partner role, not passive capital allocation.

1) How Large Corporate M&A Creates “Scale” (Mail.ru Experience)

In his Mail.ru tenure, Milевский describes the company as an unusually deal-driven investment holding inside a large ecosystem—where M&A could significantly affect profitability and capitalization.

He argues that successful acquisitions are rare, especially in Russia, because deals must create real, measurable added value. That requires more than identifying synergy—it depends on speed and integration, and on finding situations where integration can truly work.

Examples mentioned:

  • Pixonic (games): acquired; later produced strong profit/dividend-like outcomes.
  • Consolidations in sectors like:
    • Foodtech (e.g., Delivery Club; later integrated under Yandex Food)
    • Scooter delivery
  • Growth in online education via acquisitions/mergers (e.g., early-stage players such as GeekBrains and Skillbox, and later consolidation).
  • Gaming consolidation and creation of an internal “gaming direction” after earlier studio mergers.

2) Why S&P 500 / Index Investing Isn’t the Main Point (Venture & Early Deals)

The host frames the question: if S&P 500 returns may outperform most funds, why take the extra risk of venture/startup investing?

Milевский’s response: purely financial logic is insufficient—the purpose is active participation, building companies, and creating value, not “beating an index.” He also explains venture’s structure: funds often follow power-law outcomes, where many fail and a few winners dominate results.

3) His Investment Model: “Early + Selective + Operational Partnership”

He contrasts his approach with:

  • Business angels, who often write many small checks and then step back.
  • Large VC funds, which frequently invest later when traction and financial indicators are clearer.

His model:

  • Invest earlier, often before product-market fit is proven.
  • Act as a partner in execution, supporting corporate development functions such as:
    • fundraising and legal structuring
    • strategic product vision
    • hiring key people
    • filling founder gaps in domain expertise or time
  • Keep the portfolio limited: roughly ~10 companies at a time, not hundreds.

4) What He Looks for at the Earliest Stage: Team, Founder-Market Fit, Product Signals

Milевский says the earliest-stage criteria are mostly:

  1. Team Including the founder’s ability to build vision, earn trust, and adapt during pivots.

  2. Market Size, growth drivers, barriers/advantages, and timing.

  3. Product Value proposition and early signals like customer feedback/retention.

He emphasizes pattern recognition developed by studying many companies and founders, rather than relying on a single metric.

5) “Casino” Risk vs. How He Filters Bets

While early-stage investing can feel like a “casino,” he claims filtering is still possible through:

  • assessing vision quality and founder capability
  • evaluating whether the founder can iterate toward market fit
  • looking for evidence the company can hire and execute
  • comparing to competitors and considering market dynamics (he even mentions doing an exercise compiling world-fund criteria)

6) Why He Avoids Passive Investing When He Has an Operating Role Elsewhere

He argues that if you’re operationally busy as an entrepreneur, treating investing as a passive project aimed at financial returns is counterproductive. Investing should be treated like a profession or a structured partner function—requiring time, attention, and involvement.

7) Why Russia Limits Capitalization-Based Growth

A key theme: high venture-like capitalization multiples are harder to achieve in Russia because:

  • fewer venture investors exist, and large checks are uncommon
  • participants often pay for facts/profits, not long-duration growth narratives
  • public-market multipliers are comparatively lower, making “venture math” less workable

Therefore, in Russia his approach often resembles direct/late-stage or buy-and-build, rather than classic venture growth bets.

8) How “Global Winners” Emerge Inside a Market (Venture Success vs Incumbents)

He discusses why sometimes new players beat incumbents: it’s not only capital or luck, but founder strength + execution + correct segment strategy. He also notes cases where the “ecosystem approach” used by giants wasn’t enough—sometimes new management execution reshaped outcomes.

For gaming, he highlights:

  • Russian-speaking teams’ creativity and storytelling
  • acquisition logic: buying teams and capabilities that are difficult to replicate inside bureaucratic corporations

9) Specific Case: Mihote / Mundfish (Atomic Heart) and Creative Differentiation

He describes how his involvement evolved with the Moon / “Mundi…” project (the subtitles refer to Mofiish / Mundfish and the game Atomic Heart):

  • He and the founder (Robert) initially met through deal-related conversations.
  • Later he joined to help structure investment/partnerships and connect the right ecosystem.

“Win” traits attributed to the team:

  • strong creative vision and world-building
  • storytelling creativity that wasn’t based on copying existing games
  • chemistry and win-win alignment with the founders

10) Personal Philosophy: Why Investing for Him

  • His primary goal is constant happiness and internal satisfaction, along with influence through building companies and supporting founders.
  • Money is described as secondary: he invests own capital and attention, and doesn’t chase a fund-building empire as an end goal.
  • He explains leaving Mail.ru as a moment where financial gravity and a new leadership/strategy horizon made it better for him to build something more independent.

11) Practical “Rules” and Life Skills

He emphasizes:

  • rapidly changing conditions and the ability to adapt quickly
  • AI/tools can accelerate work, but the key skill is maintaining the ability to think and focus amid information overload
  • methods for managing energy and sustaining high performance (sports, reboot/pilgrimage-style retreats, breathing practices)

Presenters / Contributors

  • Алексей Милевский — guest; former Head of M&A at VK/Mail.ru Group; investor
  • Александр — host / interviewer (“Sasha”)

Original video