Retirement Answer Man

Welcome to the last episode in the Entrepreneurship in Retirement series on Retirement Answer Man. We have been discussing the dream of entrepreneurship after retiring during the past three episodes of this series. This episode closes the series as I interview 3 different entrepreneurs that got sick of the rat race and struck out on their own. These entrepreneurs have very different stories about how they launched and lived their dream. They share what motivated them to entrepreneurship, how they started, and what their lives look like now. Listen to this episode to learn from their retirement lessons as you embark on your own entrepreneurial journey.

Vinnie quit his dream job to strike out on his own and now has so much time freedom that he never wants to retire

Have you ever heard about people that say they never want to retire? That is the case of my friend Vinnie. Vinnie was a sports photographer. He had a dream job at a newspaper traveling the world and photographing major sporting events. Vinnie won several awards for his photography but still only made about $15 an hour. Once his wife got pregnant with his first child he realized that his dream job was unsustainable for a family. This spurred him to pursue opening a freelance photography business of his own. After several years Vinnie pivoted his business to something that would free his time more than his wedding photography business. Listen to the valuable lessons Vinnie relays and hear why he doesn’t plan to ever retire.

Is entrepreneurship right for you? Carey Green doesn’t think it’s for everyone

After more than 20 years as a pastor, Carey Green lost his passion for his career. He knew he needed to start his own business after discovering that a change in career fields wouldn’t pay enough money to support his family. He did some audio editing for an online friend and soon discovered his niche. Carey has learned to scale his business slowly over time by implementing systems that will allow him to step away from the day to day operations. This will allow him more time freedom as his podcast company grows. Listen to this episode to hear why Carey feels that entrepreneurship is not for everyone.

Mark Ross helps those that are considering a pretirement stage to their retirement

Mark Ross worked for 30 years in public service at the parks department. At age 58 he retired after realizing that he should be doing something else with his life. He just wasn’t quite sure what it was. Mark says that letting go of a steady paycheck was the scariest thing he has ever done. Although he wanted to work, he wanted to do so on his own terms. This transition has led Mark to become a coach to those in their 40's and 50's who are contemplating pretirement. He has so much to teach his clients about how to discover the possibilities of pretirement and how to implement them. Listen to Mark’s retirement lessons for those considering a pretirement phase of their retirement.

What can these guests teach you about entrepreneurship?

All three of my guests come from very different backgrounds and have pursued their entrepreneurial dreams for different reasons. They each have valuable lessons to teach our listeners about many aspects of entrepreneurship. If you are considering opening any sort of business in retirement you’ll want to listen to the entire Entrepreneurship in Retirement series starting with episode 224. The lessons over the past four episodes are a great start to the research you will need to begin to get started on your own entrepreneurial journey.


  • [2:22] In July we will tackle social security so be sure to listen in if you have any questions


  • [3:14] Meet Vinnie, a sports photographer, turned wedding photographer, turned writer
  • [22:33] Meet Carey Green, pastor turned podcast editor
  • [39:05] Welcome Mark Ross, a solopreneur after 30 years in public service


  • [60:46] If you really want to pursue the entrepreneurial journey then meet some other people taking that journey


  • [61:58] Vince Pugliese has a group for those that are entrepreneurs, join it!

Resources Mentioned In This Episode

Next Thing Group with Mark Ross - get his free PDF to help you decide what to do next!

Email Mark Ross

Carey Green’s - Podcast Fast Track website

Vinnie’s website: The Freelance Tribe

BOOK - Freelance to Freedom by Vincent Pugliese

BOOK - 48 Days to the Work You Love by Dan Miller

BOOK - Don’t Retire Rewire by Jeri Sedlar

BOOK - Will it Fly by Pat Flynn

BOOK - Rich Dad Poor Dadby Robert Kiyosaki

BOOK - Lynchpin by Seth Godin

BOOK - Total Money Makeover by Dave Ramsey

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Ask Roger a question

Work with Roger

3-video Series: 5 Minute Retirement Makeover

Roger’s Retirement Learning Center

The Retirement Answer Man Facebook Page

Direct download: RAM227.mp3
Category:general -- posted at: 6:00am CDT