San Eng

Speaker and Coach

San Eng

I speak and coach, selectively, for boards, CIOs and investors, East and West. Thirty years investing across 15 countries. Teaching is learning, and coaching is my way of giving back to the community.

Talks on

East/West AI
What each side is building and what it means for capital
Greed vs Fear investing
Lessons from both sides of the table, as founder and investor, and the discipline behind The Ten Commandments of Investing
Parenting: Raising kids who earn their wins and can stand on their own
Startups: Building and backing founders in the AI era

Chairman, WorkOptional. Lectures at Wharton alumni events.

Dozens of talks, lectures and podcasts
Teaches in the University of Waterloo AI-CTO Program
Co-author of The Ten Commandments of Investing, a WSJ and USA Today best seller

Invite San to Speak or Teach

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Every talk connects to East/West AIpha, the WorkOptional briefing for investors.

Watch San

San on life in 10-year chapters, financial independence, and coaching the next generation.

San Eng speaker reel, 2 minutes 22 seconds

Get Diversified Podcast EP10 and IVYFON Family Office Forum | 2:22

Speaker reel: on life, wealth and family

Watch the reel

Signature talks

Two core talks on East/West AI and investing, the heart of WorkOptional, plus talks on parenting and startups.

01
Core talk | East/West AI

East x West AI: Making the Two AI Worlds Work Together

Outside China, half the AI revolution is invisible.

What each side is building, from DeepSeek, Qwen and Kimi to the Western leaders, and what it means for capital. Audiences leave able to make the two AI worlds work together.

The heart of East/West AIpha, the WorkOptional briefing that helps investors read both AI worlds.

02
Core talk | Greed vs Fear investing

Greed vs Fear: Both Sides of the Table

Buyers and sellers feel the same greed and fear. Discipline decides who comes out ahead.

San has raised $250M+ as a founder and deployed $500M+ as an investor, so he has felt greed and fear from both chairs. He pairs that view with the discipline behind The Ten Commandments of Investing, a WSJ and USA Today best seller. Audiences leave with a discipline for decisions made under greed and fear.

The investor discipline WorkOptional brings to AI era markets in East/West AIpha.

San also speaks on

Parenting

Earn the Puppy: Raising Kids Who Can Stand on Their Own

San grew up in New York's Chinatown with parents in garment factories and won a scholarship to Exeter. He shares practical ways to raise kids who earn their wins and stand on their own, and why kids can tell when a win was bought for them.

Startups

Building and Backing Founders in the AI Era

What founders need from backers and what backers look for in founders, now that AI changes the cost of building. Founders and investors leave speaking the same language.

Short bio for programs and introductions

San Eng is Chairman of WorkOptional.ai and co-author of The Ten Commandments of Investing, a WSJ and USA Today best seller. He teaches in Waterloo's AI-CTO Program with Prof. Felix Arndt. He has invested across 15 countries for thirty years.

Featured talks, lectures and podcasts

From upcoming summits back through lectures and podcasts.

AiSEAN Summit 2026
Upcoming

8 to 9 Dec 2026

AiSEAN Summit 2026

Hilton KL Sentral, Kuala Lumpur | Featured Voice and Advisory Council

I join AiSEAN Summit 2026 in Kuala Lumpur as a Featured Voice and member of the Advisory Council. My talk: East x West AI: Making the Two AI Worlds Work Together. Format to be announced.

Event page

AI-CTO Program
Ongoing

2026, weekly

AI-CTO Program

University of Waterloo, Conrad School, with Prof. Felix Arndt | Teaching

I teach CTOs to own the AI stack: architecture choices, AI agent governance, build versus buy, and how to lead when the tools change every quarter.

Conrad School

Phuket Summit 2026: AI Marketing and SEO Summit

3 to 5 Apr 2026

Phuket Summit 2026: AI Marketing and SEO Summit

Centara Grand Beach Resort, Phuket | Speaker

AI marketing through an investor's filter: most teams buy tools, the winners rebuild how they operate. I shared the #10Cs lens from Book 2 on distribution, trust and compounding.

Event page

Investments in Practice: Greed vs Fear

12 Sep 2025

Investments in Practice: Greed vs Fear

Sasin School of Management, Chulalongkorn University, Bangkok | Guest lecturer, MBA Investments class

How investors behave when the money is real. Greed writes the check, fear signs the loss, and discipline decides who compounds.

Sasin School of Management

The Hospitality Edge, S02EP09

1 Oct 2024

The Hospitality Edge, S02EP09

The Hospitality Edge podcast | Guest

I discuss raising capital and using AI for property management: automated leasing, maintenance and guest messages. People remain essential for judgment and trust.

Listen on Spotify

The Impact of AI and Robotics on Our Work Optional Future

29 Aug 2024

The Impact of AI and Robotics on Our Work Optional Future

Penn/Wharton Club of Greater Tampa and Harvard Alumni Club, South Tampa | Speaker

What AI and robotics do to work: which jobs compress, which margins expand, how leaders redeploy people early. Automate the repeatable, amplify the human.

Get Diversified, EP10

5 May 2023

Get Diversified, EP10

Get Diversified podcast with Melvin Landry Jr. | Guest

San shares lessons from multifamily real estate and how families should think about concentration. He explains how to balance focused positions with diversification.

Watch on YouTube

IVYFON Dallas Family Office Summit

25 to 26 Oct 2022

IVYFON Dallas Family Office Summit

Ivy Family Office Network, Dallas | Panelist, family office portfolio diversification via real estate

Family capital thinks in decades. Rigorous fundamentals, respect for debt and a long-term view still find real opportunity in real estate.

Watch the panel

Invest Florida Show, EP224

22 Mar 2021

Invest Florida Show, EP224

Invest Florida, a real estate podcast | Guest

Central Florida multifamily from an investor's seat: basis, operations and tenant reality.

Listen to the episode

More talks, lectures and podcasts

On request
The Board's AI Questions: Build, Buy or Wait
Talk for boards and directors, drawn from the AI-CTO Program at the University of Waterloo | Speaker
10 Jun 2026
In Search of My 2nd Brain: Still Lost on AI Agents
WorkOptional.ai meetup, online | Speaker
3 Jun 2026
Billion Dollar Apartment Developer Podcast, EP533
Podcast | Guest
21 Jan 2026
AI Productivity Meetup: Tools and Tricks for Startup Entrepreneurs
Online | Speaker
10 Jan 2026
WGON Radio Tampa, real estate interview
Radio, Tampa | Guest
7 Aug 2025
Sneak peek of Book 2, The Ten Commandments of Investing in the Age of AI
Bangkok, with Dr. Felix Arndt | Speaker
May to Jun 2025
WorkOptional meetup host series
Bangkok and online | Host and speaker
16 Apr 2025
WorkOptional networking and AI marketing night
Bangkok | Host and speaker
28 Mar 2025
Can AI Autonomously Run Your Short-Term Rentals?
Online, with Luca Zambello and Ariel Cochrane | Speaker and host
10 Sep 2024
Easy Win AI Real Estate Show, EP618: How AI Is Taking Over Property Management
GowerCrowd podcast | Guest
4 to 5 Dec 2023
IVYFON Miami Family Office Forum, Real Estate 2024 panel
Ivy Family Office Network, Miami | Panelist
20 Oct 2023
The Naked Truth About Real Estate Investing, EP297
Podcast | Guest
17 May 2023
Penn/Wharton Club of Greater Tampa learning event
Tampa | Host
2 Feb 2023
St. Pete VC Fast Pitch
St. Petersburg, Florida | Investor panelist
Mar 2022
The Exit by Flippa, EP77: Always Be Prepared for an Exit
Flippa podcast | Guest
Earlier
Greed vs Fear seminar
CEIBS, Shanghai | Guest lecturer
Earlier
Greed vs Fear seminar
University of Nottingham Ningbo China | Visiting lecturer
Since Feb 2025
Host, WorkOptional AI Builders, a recurring series in Bangkok and online since Feb 2025

Talks and coaching are education only, not investment advice.