Should I Leave My $500,000 Job for My Side Hustles?

EntreLeadership

Ramsey Network

Management, Entrepreneurship, Business

4.7 • 4.4K Ratings

🗓️ 15 April 2026

⏱️ 9 minutes

🔗️ Recording | iTunes | RSS

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Summary

Playing it safe might be costing you more than you think. In this episode, Dave Ramsey takes a call and breaks down how to confidently transition from a high-income W-2 job to business ownership by focusing on proven growth, not just savings. Next Steps: 📞 Have a question for the show? Call 844-944-1070 or send us a message: https://ter.li/ask-us 📚 Learn about the EntreLeadership System™: https://ter.li/system-p 💻 Get EntreLeadership Elite™ for your business: https://ter.li/elite-p ✉️ Sign up to receive tactical tools, advice and resources in your inbox every week: https://ter.li/enl 🏢 Attend EntreLeadership Summit: ttps://ter.li/Summit-Leadership 🎤 Attend EntreLeadership Master Series: https://ter.li/masterseries 📖 Order Dave’s book, Build a Business You Love: https://ter.li/b4kru2 Connect With Our Sponsors: Go to Belay Solutions or text ENTRE to 55123 for their free resource! Go to Christian Healthcare Ministries and use code ENTRE for a 50% credit towards your first month of membership. Visit NetSuite today to learn more. Listen to More From Ramsey Network: 🪑 Front Row Seat with Ken Coleman 🎙️ The Ramsey Show 💸 The Ramsey Show Highlights 🧠 The Dr. John Delony Show 🍸 Smart Money Happy Hour 💰 George Kamel Ramsey Solutions Privacy Policy Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	From the headquarters of Ramsey Solutions, this is Entree Leadership.
0:12.2	I'm your host Dave Ramsey with over 30 years of experience leading in the trenches right alongside you.
0:17.1	If you got a question for the show, go ahead and click the link in the description.
0:21.0	We're glad you're here.
0:22.4	All right, Jeff is with us in Kansas City.
0:24.9	Hi, Jeff. How are you?
0:26.9	Doing well, sir. How are you doing?
0:28.5	Better than I deserve. How can I help?
0:31.5	Well, one, appreciate the opportunity to speak with you, diving right into it.
0:37.2	I own a couple of businesses, and I am looking at
0:41.4	when is it the right time to exit my W-2 to focus on those businesses. Right now, I'm in technology
0:49.4	sales, and my W-2 income is between $250,000 to $500,000 a year.
0:54.8	And then my wife and I have a one and a half and a three-year-old.
0:59.4	My wife runs business number one, which is an event rental company.
1:04.4	It does about $500,000 in revenue.
1:07.2	We started that in three years ago.
1:10.3	And then last year, we purchased a moving company that does about $500,000 in revenue.
1:16.0	And I have a partner that owns 20% that runs the day-to-day on that.
1:21.2	Both businesses are debt-free.
1:23.4	Well, the profit on those two businesses.
1:25.5	Yes, sir.
1:26.2	The moving company is about 15 to 20%.
	...

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