“Market value fuels the ego, makes you feel like a big deal. But income fuels the yacht.”
Steve Selengut spent 40 years building a portfolio management system that most financial advisors never teach and Wall Street rarely promotes. In this conversation, he walks through the mechanics of income investing, why founders are uniquely positioned to understand it, and what it takes to start generating reliable cash flow from a portfolio regardless of what the market is doing.
Most founders build income-generating businesses and then park that income in portfolios that do nothing. Income investing is the discipline that changes that equation, and Steve Selengut has spent 40 years refining exactly how it works.
His framework starts with a principle that is easy to state and rarely practiced. A profitable company should pay its shareholders. That conviction became a quality filter, a selection methodology, and ultimately a system that had him earning four times his New York salary from his portfolio by age 34.
The vehicle at the center of his approach is the closed-end fund, a trust structure purpose-built for income investing that trades on exchanges and must distribute the vast majority of its earnings to shareholders. Steve targets yields between 9 and 10 percent annually.
The framework will feel familiar to any founder who has managed inventory, measured turnover, or applied the velocity of money to a business. The mechanics are the same. The discipline is the same. The guardrails replace guesswork, and the system demands less than an hour a day.
If income investing is not already part of how you think about your portfolio, this conversation gives you a place to start.
• Income investing is built around cash flow, and Steve explains how to construct a portfolio that generates it consistently.
• Closed-end funds are the core vehicle, and understanding how they work changes the way a founder thinks about where money should live.
• The velocity of money applies to portfolio management, and Steve walks through how disciplined profit-taking compounds returns over time.
• Diversification across sectors functions as an active strategy, and Steve explains why owning everything positions you to benefit wherever gains occur.
• Managing this approach takes less time than most founders expect, and Steve describes what a typical day looks like.
Rick Meekins ( https://rickmeekins.com) is a serial entrepreneur, strategic business disruption advisor, podcast guest, and host of The Relentless Pursuit of Winning Podcast, where he explores what it actually takes to build, lead, and sustain meaningful businesses. With over 30 years of experience working alongside founders and leadership teams, Rick focuses on helping companies develop and implement disruptive advantages and developing platforms to explore and distribute human insight.
Interested in working together, having Rick speak, or partnering with the show?
Start here: rpowpodcast.com/contact/
01:38 Steve’s Origin Story: Stock Certificates and a Father’s Advice
04:44 Building an Income Machine from the Ground Up
09:30 Why Market Timing Fails and Income Holds Steady
11:10 The Four Pillars of Sound Investing
13:34 Closed-End Funds Explained
19:30 Municipal Bond CEFs and Tax-Free Income
22:11 Retirement Planning for Business Owners
27:33 Setting Guardrails: The Discipline Behind the System
31:00 Diversification as an Offensive Weapon
35:46 The Community, the Book, and the FIRE Course
40:52 Defining Winning and Staying Motivated
Steve Selengut spent four decades doing what most financial advisors never attempt: building a system entirely around income. He managed 110 million dollars in client assets as a solo practitioner and retired from advisory work in 2023 because his portfolio made the decision easy. His book Retirement Money Secrets received recognition from the American Literary Foundation and has reached thousands of readers rethinking what a portfolio is supposed to do. Steve now teaches that system at theincomecoach.net ( https://theincomecoach.net).
If this conversation challenged the way you think about what your portfolio should be doing, Steve has built an entire course designed to take you further. His FIRE course on income investing walks you through the process of building a portfolio that generates reliable cash flow, step by step, in your own time. As a listener of this show, Steve is extending 25 percent off to you personally. Reach out at theincomecoach.net (https://theincomecoach.net) and mention this episode to claim it.