Brutally Honest Talk About Quitting Your 9 to 5 to Start a Business - with Steve Rolle Artwork

Digital Trailblazer Podcast

Learn how to build a legitimate, profitable online business from the ground up without the shiny objects, hypey gimmicks, and without the stress and overwhelm.

Your hosts, Todd and Leah Rae Getts take you inside the businesses of successful entrepreneurs and show you the online marketing strategies they used to go from ground zero, working 9-5 jobs, to building successful 6 and 7 figure online businesses.

Whether it’s high-ticket coaching, consulting, online courses, agencies, affiliate marketing, network marketing, Amazon FBA, or eCommerce, you’ll learn the online marketing strategies that successful entrepreneurs are using right now to take their online businesses to the next level...

We cover everything from Facebook ads and Instagram ads, to content marketing, SEO, social media marketing, branding, video marketing, webinars, sales call scripts, sales funnels, email marketing, AI and automation, and more!

All Episodes

Digital Trailblazer Podcast

Brutally Honest Talk About Quitting Your 9 to 5 to Start a Business - with Steve Rolle

October 13, 2026 • Leah Getts & Todd Getts • Episode 238

0:00 | 53:25

Episode 238: Need more Leads and Traffic in your business? This will help: https://join.digitaltrailblazer.com/visibility-lab

Many coaches and course creators quit their 9-to-5 the moment their business has a few good months, only to watch revenue dip, savings drain, and stress take over. Others stay stuck, convinced that more time is the only thing standing between them and success. Either way, the business runs them.

In this episode, we speak with Steve Rolle, author of The Future You Choose, and talk about the brutal reality of making the transition from 9 to 5 job to full time entrepreneur. He teaches us how to tell when your business is truly ready to support you. You’ll discover the hidden levers behind consistent revenue, why time is rarely the real bottleneck, and the costly savings mistake that sinks many new entrepreneurs.

About Steve Rolle: Steve is an entrepreneur, investor, host of the Rolle With Steve Podcast, and author of The Future You Choose. Raised in a low-income household in Washington, D.C., he started small side businesses while serving full time in the U.S. Army. Those early experiments grew into multiple companies that have generated more than $100 million in combined sales across e-commerce, manufacturing, and distribution.

Over two decades, Steve has launched, scaled, and exited businesses built to run without the founder in the day-to-day. Today he helps people spot overlooked opportunities, turn side hustles into real businesses, and build lasting financial and time freedom.

Connect with Steve:
https://steverolle.com/links
https://steverolle.com/

Want to SCALE your online business bigger and faster without the endless hustle of networking, referrals, and pumping out content that nobody sees?

Grab our Ultimate Ad Script for Coaches, Agencies, and Course Creators.

Learn the exact 5-step script we teach our clients that allows them to generate targeted, high-quality leads at ultra-low cost, so you can land paying customers and clients without breaking the bank on ad spend.

Grab the Ultimate Ad Script right HERE - https://join.digitaltrailblazer.com/ultimate-ad-script

✅ Connect With Us:
Website - https://DigitalTrailblazer.com
Facebook - https://www.facebook.com/digitaltrailblazer
TikTok: https://www.tiktok.com/@digitaltrailblazer
X (Twitter): https://x.com/DgtlTrailblazer
Instagram: https://www.instagram.com/DigitalTrailblazer