Sleep Well Investments

Sleep Well Investments

Deep Dives

SWI Pick #24: Digital Medical Toll Bridge, AI-Resilient

100% retention over nearly 2 decades, AI is a tailwind.

Trung Nguyen @SWI's avatar
Trung Nguyen @SWI
Apr 28, 2026
∙ Paid

Investing is simple - ‘buy quality and verify quality,’ but incredibly hard to execute. SWI has enjoyed a very good two and a half years, until one mistake and an AI-induced SaaS multiple compression brought the portfolio down. But changing strategy now would be a trajedy - ‘buy high sell low’.

Patience is required.

The good news is that my investment period runs until 2037, so what has happened in the past 6 months might not matter much in a few years, and definitely not in over a decade. I still believe that consistently (i) putting aside emergency funds, (ii) investing excess in high-quality companies, and (iii) staying invested through tough times will help me build a reasonable capital and knowledge base for my daughters’ future.

Today, I am putting money where my mouth is - I will initiate a starting position in SWI Pick #24 and add more over the next few quarters.

Learning from my mistake, this is a more predictable business and will be a smaller starting position.

  • #24 is a technology leader whose alternatives are legacy solutions and AI as an accelerator instead of a competitor.

  • The product is mission-critical to top-tier hospitals, 100% of whom renews long-term contracts lasting 5+ years.

  • Durable growth opportunity with a large whitespace and a market cap of under $10B.

  • Clean financials and prudent accounting, no debts, 50% of cash allocated to dividends, and capex-light.

  • Risks include high valuation, looming succession planning, legacy solutions fighting back, and AI still bringing uncertainties.

  • Why now? The business has been perennially expensive, but it has been bundled with the ‘AI SaaSapocalypse’, pulling the stock down by nearly 60% in the last 7 months from its peak, giving it a good time to buy in stages (dollar-cost-average) into a position, or at least to do the work now before we get a better entry point.


If you are new to SWI, here is the link to all write-ups.

What is Sleep Well Investments?

  1. Deep research on a few exceptional niche leaders.

  2. Patiently waiting and thoroughly following up for buying opportunities.


We will go through:

  • Investment Thesis

  • Why does it help us sleep well?

    • Mission-critical product, slow-changing customers

    • Founder-led management

    • Solid moats and barriers to entry

    • Organic growth opportunities

  • Limited competition

  • Risks - legacy fighting back, key man

  • Valuation

  • Sleep Well Scores

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