#913 From Wall Street to Main Street: Jim Pfeifer’s Passive Income Playbook

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

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4.9 • 675 Ratings

🗓️ 23 June 2025

⏱️ 38 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Welcome back a returning guest-someone who’s made a huge impact in the passive investing world and continues to be aleading voice in the space, Jim Pfeifer. Jim, co-host of the Passive Pockets Podcast and when we last spoke a little over a year ago, he shared his journey transitioning from an active realestate investor to a full-time passive investor. Since then, he’s been busy growing his community, Left Field Investors, which recently merged with Bigger Pockets to create what is now Passive Pockets—a thriving network designed to empower limited partners through connection, education, and access to high-quality deals.

We’re catching up on everything Jim’s been working on and what’s new in his world!

Connect with Jim: https://www.linkedin.com/in/jimpfeifer, https://passivepockets.com/podcast/

Highlights:

3:08 - Why Jim Left Wall Street for Passive Investing

6:00 - How Left Field Investors Was Born

9:22 - The Difference Between Being “Passive” and Being “Hands-Off”

14:45 - Why the Operator is More Important than the Deal

21:30 - Market Cycles and Opportunity Timing

28:05 - Advice for New Passive Investors

Quote: “True wealth is freedom over your time—not just returns on your money.”

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!
If you’re a high net worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.
Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.
Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

Transcript

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0:00.0	You've been searching for the best way to generate passive income in your life and heard that real estate is a great way to do it.
0:09.4	But you're tired of all the so-called gurus who are all talk and no substance.
0:15.3	Get ready to celebrate because Kevin Buck has spent 14 years successfully making it happen. This is the real estate investing for
0:23.6	cash flow podcast. Now, here's Kevin Bup. Hey guys, Kevin Bup here, and I want to welcome me to another
0:32.1	episode of the Real Estate Investing for Cash Flow podcast. Our mission is to help you build and maintain
0:36.7	massive amounts of cash flow
0:38.4	through income producing real estate investments. And guys, today I'm excited to welcome back a
0:43.1	returning guest. He's been on, I guess it's been about a year and a half or so, someone who's
0:47.3	really made a huge impact in the passive investing space, you know, the limited partner space
0:52.2	and continues to really be a leading voice for all accredited investors, you know, limited limited partner space and continues to really be a leading voice
0:54.4	for all accredited investors, you know, limited partners. I guess not accredited as well. And so Jim
1:00.0	Pfeiffer, excited to have him back here. Guys, for those that don't know, Jim is the, the co-host of
1:05.1	Passive Pocket's podcast. And, you know, when we last spoke, again, about a year and a half ago,
1:10.1	he, you know, in that podcast episode, he, about a year and a half ago, he, you know, in that podcast
1:11.3	episode, he really shared his journey. We talked about him transitioning from an active real estate
1:16.3	investor to a full-time passive investor. And, you know, since then, he's been, he's been incredibly
1:21.0	busy. He's growing his community left field investors, which, which we'll talk about this today as
1:26.2	well, it recently merged with bigger pockets
1:28.4	to create what is now passive pockets. And so passive pockets is a network that really offers
1:34.7	resources and helps empower limited partners, limited investors through, you know, connection,
1:39.5	education, and other various resources. And so guys, in today's episode, we're just going to be
1:43.6	catching up. We're catching up with Jim to see what's, you know, what he's working on and what he's up to,
	...

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