Episode Details

Want to start dividend investing but don't know where to begin? Or maybe you already have a portfolio and want to transition toward dividend income without creating a massive tax bill?That's exactly what we're tackling in this episode of the Dividend Stockpile.I'm joined by Jenny Harrington, CEO and Portfolio Manager at Gilman Hill Asset Management, where she manages the firm's Equity Income Strategy. Jenny specializes in dividend income investing, making her the perfect person to help answer these questions.We walk through the process of starting or transitioning to dividend investing, from evaluating individual companies and dividend safety to choosing between dividend ETFs and individual stocks.We also tackle an important listener question from an investor with a 60/40 portfolio containing stock ETFs, individual bonds and bond ETFs with significant long-term capital gains who wants to transition toward a dividend-focused strategy without unnecessarily creating a huge tax bill or taking on too much portfolio risk.In this interview, we discuss:- How to get started with dividend investing step by step- What makes a dividend-paying company a high-quality investment- Dividend growth vs. current dividend yield- How to identify potential dividend traps- Dividend ETFs vs. individual dividend stocks- High-income ETFs such as JEPI and SPYI- How options-income ETFs fit into an income portfolio- How to transition an existing 60/40 portfolio toward dividend investing- Managing significant long-term capital gains during a portfolio transition- Balancing tax efficiency with portfolio risk- Jenny's top advice for investors starting their dividend journeyOne of the biggest mistakes new dividend investors can make is focusing only on the size of the yield. We discuss why dividend sustainability, business quality, growth, valuation and total return all matter when building an income-focused portfolio.Whether you're just starting out, approaching retirement, or trying to transition an existing portfolio toward generating more income, this conversation provides a practical framework for thinking about dividend investing.Jenny's Dividend Investing Book: https://bookshop.org/a/115069/9781804090466Jenny's new book (launching 11/17/26): https://bookshop.org/a/115069/9781804095287