In this Investor Insights Skull Session, I had the chance to sit down with Lee Roach, a private investor whose work I’d been following through Twitter and his Substack, The Value Road. He emphasizes the importance of understanding company fundamentals and being contrarian in market pullbacks and aims to reach $100,000 in annualized income on Substack to become a full time investor.
Investor Insight Skull Sessions are deep discussions with investors to learn about their investing journey, investing process and favorite ideas.
I think what will resonate with a lot of readers is how unglamorous and grounded Lee’s path into investing has been. He didn’t come up through Wall Street or finance school. He found his way in through history books, the Great Recession, and eventually a thrift-store copy of The Intelligent Investor. That curiosity slowly turned into a disciplined value framework shaped by real-world scars: early losses in hype-driven sectors like green energy and cannabis, followed by a shift toward businesses he could actually understand.
Industrial companies, asset-heavy balance sheets, boring operations are where he sees his edge. He’s very clear about what he avoids (biotech, speculative tech, anything he can’t value with confidence) and equally clear about why writing matters: public feedback forces rigor, exposes bad assumptions, and sharpens conviction. That humility, knowing what you don’t know, is something many investors never develop.
Even though Lee likes investing in smaller companies, he’s comfortable moving outside that box. For example he’s owed stocks like Dollar General Corporation (NYSE:DG) and United Natural Foods, Inc. (NYSE:UNFI).
As a microcap investor who craves information arbitrage, what I really liked about Lee’s approach is how catalyst-driven it is and that he’s constantly hunting where the market is overreacting: missed filings due to auditor changes, cybersecurity incidents, failed acquisitions, regulatory overhangs: situations where the business is intact but sentiment is broken.
He’s not chasing momentum and likes to separate temporary noise from permanent impairment.
His process is straightforward, but not easy: screen relentlessly, focus on enterprise value and net asset value, wait for something to “snap back,” and sell when the original thesis plays out, not because the stock is up.
There’s also a refreshing transparency here. Lee shares his portfolio moves, tracks his results, and openly talks about volatility and mistakes. We chatted about small-cap industrials, legacy media as a deregulation play, and even distressed bonds as a potential strategy.
