How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James

The Money Mondays

Dan Fleyshman

Business, Entrepreneurship

4.3 • 483 Ratings

🗓️ 4 August 2025

⏱️ 47 minutes

🔗️ Recording | iTunes | RSS

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Summary

In this powerhouse episode of The Money Mondays, Dan Fleyshman brings together two incredible entrepreneurs who are reshaping the way people build wealth, invest capital, and give back.• Gary Lipsky, founder of Break of Day Capital, shares how he went from producing indie films and running youth programs to managing $100M+ in real estate assets. He breaks down real estate syndications, how to spot red flags, and why passive investing is one of the smartest wealth plays for busy professionals.• Douglas James, a Navy veteran turned tech founder, walks through his evolution from lead generation agency owner to co-creator of LeadFi, a cutting-edge platform using proprietary data and AI to supercharge high-ticket sales. He opens up about losing 8 figures, hitting rock bottom, and rebuilding with faith, focus, and purpose.In this episode you’ll learn:• Why hands-off real estate investing creates true freedom• How to evaluate IRR, cash flow, and cap rates in deals• The power of AI and real-time data for qualifying leads• What both men teach their kids about charity and legacy• Why neither plans to hand over massive wealth to their children without preparationFrom real estate to revenue tech, this episode is a blueprint for how to make, grow, and give money, with purpose.Like this episode? Watch more like it 👇Watch ALL Full Episodes Here: https://www.youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6k---The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place! Subscribe: https://www.youtube.com/@themoneymondays?sub_confirmation=1Dan Fleyshman,The Money MondaysLearn more here: https://themoneymondays.comWatch all the podcast episodes: https://youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6kLet’s Connect...Website: https://themoneymondays.comPodcast: https://podcasts.apple.com/us/podcast/the-money-mondays/id1663564091Twitter: https://twitter.com/themoneymondaysLinkedIn: https://www.linkedin.com/company/the-money-mondays/about/TikTok: https://tiktok.com/@themoneymondaysFB: https://www.facebook.com/The-Money-Mondays-110233585203220/

Transcript

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0:00.0	Ladies and gentlemen, welcome to a special edition of the Money Monday's podcast, where we
0:10.3	cover three core topics, how to make money, how to invest money, how to give it away to charity.
0:15.7	Our next guest has accumulated a ton of real estate.
0:19.5	He's been overseeing a real estate empire, if you will,
0:23.1	helping investors deploy capital into safe investments, strategic investments, tax benefit
0:30.2	investments, and all things related to real estate. It's called break of day capital. His name
0:34.5	is Gary Lipski. Now, as we go through this, I want you to consider maybe you're not a real estate investor or maybe you're going to do it in the future. But there's people in your life from your past, present, and future that may be very interested in real estate or may need real estate in their life. And that's why these podcasts are important. Not all episodes will be for you. There might be someone that owns a chain of restaurants, maybe someone owns a clothing line, or maybe someone like this with Gary that is deeply involved in the real estate space. Don't just listen for yourself. These podcasts are designed are for people in your life from your past, present, and future. So without further ado, Gary, if you can give us a quick two minute bio,
1:11.7	so we get straight to the money.
1:13.1	Yeah, thanks for having me, Dan.
1:14.2	Appreciate it.
1:16.0	Been entrepreneur since I was a young kid.
1:20.5	Had a restaurant delivery service, like a DoorDash
1:23.1	and a postmates in college, because we saw that they were doing it in Boston where we were living.
1:28.7	And so we started one in New York City, co-produced three low budget independent films in my 20s.
1:36.9	Then it's funny. I've kind of had three different lives.
1:41.2	I started an after school, outdoor ed, and leadership development company where we were serving 9,000 at-risk youth throughout Southern California.
1:49.0	And then I had been investing in real estate for a while and got into it full-time when I
1:53.6	sold that company at the end of 2016 and been doing real estate full-time ever since and built up a great team and
2:04.8	quite a bit of portfolio. So at first it was your own capital, just focused on buying some
2:10.0	things for yourself. What did you like at first? What was your first things you were interested in?
2:14.2	Well, I love the, it was a great way to build wealth where I had control.
2:20.0	When I invested in the stock market or other things, I felt like there was a lack of control
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