Finding Freedom Through Passive Investing W/Chad Ackerman

Nov 25

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Episode Description

Welcome to the Freedom Point Podcast! In this episode, Jeremy sits down with Chad Ackerman, a 30–year corporate HR leader turned passive investing coach who now helps professionals build time freedom through real estate. Chad shares his journey from long commutes, burnout, and uncertainty to discovering passive investing as the scalable path that finally aligned with his lifestyle goals. He breaks down how he transitioned out of his W2, the fears he had to overcome, and why he believes community and goal setting are the most overlooked tools for new investors. Whether you're overwhelmed by information, unsure how to take that first step, or worried you're too late to start, Chad offers clear frameworks and real–world examples that make the path forward far less intimidating. This conversation is packed with practical guidance, mindset shifts, and actionable strategies for anyone ready to unlock time freedom.

Summary

Tip #1: Time Freedom Starts With Clarity

“If a guy from HR can do it, anybody can do it.”
Chad explains that his real turning point came when he defined what time freedom actually meant in his own life. Clear goals reduce emotional decisions and eliminate distractions.

Tip #2: Education Creates Confidence

“Education prepared me to take that leap.”
Through podcasts, books, and meetups, Chad built enough knowledge to identify real estate as a scalable path without needing to become a landlord or give up his W2 prematurely.

Tip #3: Passive Investing Unlocks Scale

“I realized I could scale without swinging a hammer.”
His shift from single–family to passive multifamily investing came when he learned how syndications work and how they eliminate the day–to–day operational burden.

Tip #4: Goals Dictate the Right Deals

“My first investments were misaligned because I didn’t know my goals yet.”
Chad stresses that understanding whether you want cash flow, equity growth, or tax benefits helps filter out 50 percent of the noise instantly.

Tip #5: Fear Is Normal—But Action Teaches Faster

“Taking action teaches you more than any amount of analysis.”
Analysis paralysis keeps many investors stuck. Chad encourages finding the smallest safe step forward to build momentum and confidence.

Tip #6: Community Reduces Risk

“I won’t invest with an operator my community never heard of.”
Chad’s experience with Left Field Investors shows the power of learning from peers, avoiding groupthink, and leveraging shared knowledge to vet operators.

Tip #7: Network With Intention, Not Agenda

“Be genuine. Give as much as you take.”
Real trust comes from authentic conversation, curiosity, and adding value—not from chasing connections or trying to sell.

Tip #8: Market Cycles Are Opportunities

“Now is a great time to be an LP.”
Distress, rising interest rates, and operator shakeouts have created better opportunities and clarified which operators have staying power.

Tip #9: Your Risk Profile Matters

“Everybody’s risk tolerance is different.”
He encourages investors to build a personal buy box to cut emotional decision-making and evaluate deals more objectively.

Tip #10: There’s No ‘Too Late’—Only ‘Start Now’

“I didn’t start until my late 40s.”
Chad reminds listeners that success doesn't require starting early—it requires starting intentionally, with the right tools and guidance.