My 10 Key Takeaways from the Diligence Wealth Club Summit 2026
- ckcbiz40
- Aug 12
- 6 min read
In early July, I attended our 4th Diligence Wealth Club Summit 2026, which I blogged about last year when I was one of the panellist here: My 10th Year Investing milestone: On stage as panelist for Diligence Investment Membership club meet-up(19 Jul 25) .
Note: This post was originally contributed by me on Dividend Titan's blog here:
This year, our Diligence members community grew under Willie’s leadership (https://www.dividendtitan.com/) and with an audience of more than 120, we moved to the larger Vine ballroom at Metropolitan YMCA.
At the start of the event, I am grateful Willie gave special mention to me for contributing my posts on his site (see outlined in red in photo above). You can find the posts here: (a) 5 Big Mistakes Beginner Singapore REIT Investors Make ; (b) Is Stoneweg Europe Stapled Trust's 8.6% Yield a Turnaround Story? and (c) https://www.dividendtitan.com/the-one-singapore-reit-you-need-to-own-as-a-dividend-investor/
It still feels surreal. I have grown from a Diligence member attendee (in 2023 and 2024) to a panellist on stage in 2025 and turned guest contributor this year in 2026 and reviewing our Diligence meet up here! What next for 2027? 😁
As usual, Willie shared his insights into the market trends and his investing wisdom.
Thereafter, we had a panel of 3 members ranging from new investors to seasoned investors for the fireside chat, who shared their insights on navigating today’s markets.
I have distilled them into 10 key takeaways (4 of Willie’s insights and 6 lessons from the panel of members) for investors and how they can shape our investing mindset below:
Willie’s Insights
1. Stock markets at all-time high and market concentration
Willie opened by showing that index concentration (how S&P500 is now dominated by a handful of mega-caps stocks) at all-time high, a pattern historically preceded periods of market bubble unwinding.
He highlighted to watch for a few critical signs, e.g. Overly rich valuations, IPO and M&A booms, excessive debt and over-expansion etc.
The message? Even if history doesn’t repeat itself, it rhymes, and bubbles form (and burst) when optimism outruns fundamentals.
2. Beware the AI Hype and AI fear narrative
Willie shared headlines highlighting sky high valuation for AI firms like Anthropic and Open AI and SpaceX’s IPO debut.
The AI buzz narrative suggests hype is fuelling the market highs and AI fear is used to justify continued risk-taking.
The takeaway: while AI is powerful and innovation is real, hype can inflate prices beyond fundamentals. As investors, we need to separate long-term value creation from short-term speculation so that valuations do not detach from reality.
3. What to watch out for in 2026 and beyond
Looking ahead to 2026 and beyond, Willie would focus on more predictable winners such as Hyperscalers (Alphabet, Microsoft, Amazon, Meta) and fundamentally sound analytics firms (Moody’s, S&P, MSCI, Fair Isaac).
Focus on moaty businesses with durable advantages, fall back on underlying business quality.
4. Dividend as Anchors and Growth Fundamentals
Willie also shared on how dividend-focused portfolio performance showed steady growth despite shocks (inflation, geopolitical risks, FOMO, hype and fear).
Stick to discipline in valuation and dividend growth. Key takeaway: dividend growers provide resilience and stability in volatile markets and helps investors stay grounded.
During the tea break, owing to Willie’s introduction of me earlier at the start of the session, several members came up to chat with me and seek advice.
I am grateful for the great conversations we had during the short 15mins, and experiences shared, during which I realised we have many crouching tigers and hidden dragons amongst our members and their guests! There were folks who invested in private equities, wanting to invest in listed companies now, business owners, veterans in MNCs, investors with 6-digits in cash/SRS looking to deploy etc.
Members also asked me several questions, for e.g. What REIT(s) to buy now? How much dividend yield to target? How to deploy our CPF? Favourite stock idea for the moment etc.? Maybe I’ll blog about some of these in my next few posts, so stay tuned!
After the tea break, we moved on to the fireside chat with a panel of 3 Diligence members with varying backgrounds and investing experience:
· TL - A senior quantity surveyor investing in dividend and growth stocks.
· HY - A procurement specialist with roughly 2 decades of investing track record.
· YM - A former quant investment manager, who retired years ago and invests full time now.
Due to PDPA reasons, I have blanked out their faces in the photo above [Left to Right: TL, HY, YM and Willie]
Amongst the questions Willie and fellow members asked the 3 panellist include:
(1) How they got started in investing and challenges along the journey,
(2) How the investment portfolio or investing strategy evolved,
(3) What was 1 biggest investment mistake or lesson learnt,
(4) How do investors manage their psychology or how do we handle market drawdowns or when the market is at an all-time high?
(5) What advice would the 3 panellist give our members, when they want to get started investing?
What TL, HY and YM shared were the hard-won lessons who lived through crashes, including their hits and misses, regretful bad decisions. Below are the six lessons that stuck with me the most:
1) NO investor or traders have a crystal ball — protect your capital first
YM shared even professional fund managers do not have a crystal ball, and they lose money too. Long term success doesn’t come from predicting the next hot stock but from disciplined money management, position sizing, and surviving multiple market cycles.
Always protect our capital first, and the upside will take care of itself. Remember - Our first win occurs at the point of buying the stock at the right price, not at the point of selling.
That means limiting our downside, avoiding excessive leverage and diversifying our portfolio so that one or two bad investments will not wipe us out.
2) High yield does not mean sure win
HY shared that he lost ~S$300,000 investing on 2 high-yielding REITs whose prices keep plummeting through the COVID crash. However, without analysing the business, he averaged down and bought more relying on the attractive yields rather than whether the dividend yield is sustainable. Ultimately they cut dividends and he had to cut loss.
The lesson – High yield alone never tells the full story. We have to look at the business fundamentals, growth or at least the sustainability of the dividends when we invest.
3) Stay invested through downturns — every crisis is also an opportunity
A few panellists shared that their portfolio fell up to 40% during the 2008 Global Financial Crisis.
Yet those who stayed invested and bought more of the quality companies (e.g. DBS, OCBC) who’s fundamentals remained strong at depressed prices due to irrational fear reaped long term rewards when markets recovered.
Mental strength is important, if we sell everything at every panic, we give up the dividend income we were relying on. Stay in the game long enough to act decisively when it matters, i.e. buying at prices you won’t sell, selling at prices others won’t buy.
4) Psychology matters more than headlines or spreadsheets
Fear, greed, ignorance, panic, and FOMO caused more damage in the stories than bad stock-picking ever did. The conclusion: analysis and numbers only get investors halfway.
The rest is temperament — not checking your portfolio regularly, not chasing headlines or sentiments, and having a process you trust enough to fall back on when things get uncomfortable. The best portfolio is the one that lets you sleep at night.
5) Build the foundation early, then let compounding do the work
Before investing aggressively, build an emergency fund and fully cover our insurance needs first, so that we are never forced to sell investments to cover a sudden unexpected short-term need.
Save consistently and treat volatility as an opportunity to buy solid companies at great prices. Build up investing knowledge, start early, start small, because compounding over decades gives our portfolio time to work its magic, and such long runway is far more powerful than chasing short-term gains or FOMO.
6) Importance of a mentor or trusted source of investing guidance that fits you
The panellists also highlighted the importance to have experienced investors/guidance alongside our investment marathon.
Follow experienced investors or mentors who share their full track record, including the losses — not just the wins. Be comfortable with these mentors’ approach and strategy.
Make sure their game plan align with your objectives. It is also important to diversify and be at peace with different portfolios based on our own investment objectives, timeline and different risk appetites.
Conclusion
As we concluded our 2026 Diligence summit, I am reminded that investing is as much about mindset and discipline as it is about numbers.
Crashes will come, hype will fade, but businesses with strong moats and growing dividends endure. Hope you have gained insights from this sharing too! Until next year’s Diligence meet up, see you!
To your money and health,
Mr MoneyandHealth (Mr MH) 🥰
Disclaimer: The author is NOT endorsed by any companies mentioned above to write this post. The author may have been, is still vested, will be investing into several of the companies mentioned above. The above article is purely the author expressing his layman views and babbling nonsense, please forgive if it doesn't make sense. The above article is NOT financial advice, and NOT a recommendation to buy or sell any stocks or REITs. Pls do your own due diligence and/or consult a qualified financial advisor before making any moves or taking any actions. Pls note that past performance or track records is not an indicator or guarantee of future performance or potential.
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