Shailesh Kumar: Value Investing Expert, Small-Cap Specialist, Founder of Astute Investor’s Calculus

For Keynotes, Panels, Podcasts, Guest Lectures, and Virtual Events

About Shailesh Kumar

Shailesh Kumar is a long-term value investor, small-cap specialist, and founder of Astute Investor’s Calculus, a research platform focused on disciplined, evidence-based portfolio construction. With more than two decades of experience applying value investing principles to real portfolios, Shailesh specializes in small-cap research, capital allocation, and risk-adjusted compounding using frameworks such as the Kelly Criterion and Shannon’s Demon.

His methodologies combine intrinsic value analysis with systematic decision-making, helping investors build durable, resilient portfolios capable of compounding through all market cycles. His early investing books continue to circulate widely and remain in demand across secondary marketplaces.

Shailesh also co-founded Arbor Trading Post, a Michigan-based handcrafted leather goods brand, and speaks on entrepreneurship, founder-led growth, and building intentional businesses.

Signature Topics

Investing & Markets

Value investing frameworks that work in real markets
Small-cap research and due diligence
Kelly Criterion position sizing made practical
Systematic compounding using Shannon’s Demon
Behavioral discipline and risk management
Portfolio construction for long-term wealth
Building diversified portfolios with asymmetric upside

Entrepreneurship & Leadership

Building founder-led companies with intention
Craftsmanship, sustainability, and brand authenticity
Scaling product-based businesses
Operational discipline in small business
Mindset, visualization, and consistent action
Lessons learned building two parallel ventures

Why Event Organizers Book Shailesh

Real-world investing experience

Shailesh does not speak from theory. His content comes from real portfolios, real decisions, and the exact frameworks he uses to compound wealth over time.

Clear, structured insights

Shailesh presents complex ideas — Kelly Criterion, small-cap valuation, risk-adjusted returns — in a way that is accessible, pragmatic, and immediately useful.

Engaging storytelling

As both an investor and an entrepreneur building a handcrafted goods brand with his family, he brings a compelling combination of rigor and humanity.

Dual audience appeal

Shailesh speaks to investors, entrepreneurs, business owners, and teams seeking clarity, discipline, and long-term thinking in fast-changing markets.

High-quality, evergreen content

His frameworks and principles do not rely on market fads or hype. They stand the test of time.

Formats Offered

Keynote Talks (in-person or virtual)
Panel Discussions
Podcast Interviews
Guest Lectures for Universities or Accelerators
Workshops & Masterclasses
Fireside Chats

Recent & Featured Appearances

2026 schedule now being finalized — accepting select invitations.

What Audiences Say

“Shailesh brings clarity and structure to investing topics that most speakers make unnecessarily complex. His frameworks are timeless, actionable, and deeply grounded in real-world experience.”
— Event Host

Book Shailesh for Your Event

For speaking inquiries, podcast invitations, or collaboration requests, please reach out:

Email: shailesh@astuteinvestorscalculus.com
LinkedIn: https://www.linkedin.com/in/shaileshkumar1/
Website: https://AstuteInvestorsCalculus.com