Selling shares in a downturn to cover living starting in 2023 and has stayed there since. Higher refinancing costs are the main risk.
How the $100,000 Portfolio Adds Up
Name
Rate Annual
Annual Dividend Income
Paychex
4.08%
$1,020
Gladstone Investment
6.54%
$1,635
Gladstone Capital
9.81%
$2,454
Gladstone Commercial
9.91%
$2,477
Total
7.59%
$7,586
These four positions together generate $7,586 in annual passive income on a $100,000 investment, a combined yield of 7.59%. Paychex contributes $1,020, Gladstone Investment adds $1,635, Gladstone Capital adds $2,454, and Gladstone Commercial brings in $2,477.
Monthly payers make compounding faster. Each reinvested distribution buys more shares, and those shares start earning the following month. Over time, that cycle can grow the income stream without adding new capital. (We rounded up seven of our favorite monthly payers in a free report if you want more names on that schedule.)
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Lee Jackson has covered Wall Street analysts’ equity and debt research and equity strategy daily for 24/7 Wall St. since 2012. His broad, diverse career, including a stint as creative services director at an NBC affiliate in Austin, Texas, gives him unique insight into the financial industry.
Lee Jackson’s journey in the financial industry spans more than 30 years, including nearly two decades as an institutional equity salesperson at Bear Stearns, Lehman Brothers, and Morgan Stanley. His career spanned pivotal sell-side Wall Street events, from the dot-com rise and bubble to the Long-Term Capital Management debacle, 9/11, and the Great Recession of 2008. This reflects his resilience and adaptability amid market volatility.
Lee Jackson’s practical financial industry experience, gained through a career at some of the biggest banks and brokerage firms, is complemented by a lifetime of writing across various platforms. This unique combination allows him to shed light on the intricacies of Wall Street in a way only someone with deep insider experience and knowledge can. Moreover, his extensive network across Wall Street continues to provide direct access for him and 24/7 Wall St., a privilege few firms enjoy.
Since 2012, Jackson’s work for 24/7 Wall St. has been featured in Barron’s, Yahoo Finance, MarketWatch, Business Insider, TradingView, Real Money, The Street, Seeking Alpha, Benzinga, and other media outlets. He attended the prestigious Cranbrook Schools in Bloomfield Hills, Michigan, and has a degree in broadcasting from the Specs Howard School of Media Arts.

