Real Estate Investing School Podcast Episode 197

“Leaving Your 9-5 with Authority with Jesse Ray”

Date: September 30, 2024
Host: Joe Jensen
Guest: Jesse Ray (Founder, Growth House – entrepreneur-focused, co-living rentals, Phoenix AZ)

Episode Overview

In this high-energy episode, Joe Jensen interviews Jesse Ray, a former corporate sales rep who built freedom and career satisfaction through strategic real estate investing—with an emphasis on co-living houses for entrepreneurs. Jesse discusses his transformation from disenchanted salesperson to world-traveling community-builder, sharing his unique take on house-hacking, the power of intentional networks, and lessons learned building “Growth Houses” in Phoenix. They dive into Jesse’s story, strategies, notable stumbles, community-focused investing, and practical steps for listeners to follow his path out of the 9-5.

Key Discussion Points and Insights

1. Jesse's Exit from Corporate and "Not Selling Himself Short"

• Story of Corporate Exit: Jesse shares the pivotal moment he chose not to take another corporate offer after realizing his rental income surpassed the salary on the table.
• Quote [00:21]:

  “I appreciate you guys, but I’m not going to sell myself to you because you can’t afford me.”
  – Jesse Ray ([00:20:44])

2. How Real Estate Set Him Free: The Journey

• Background: Couldn’t find a job post-college, went back to being a cabana boy. Realized a need for change, got into personal development—catalyzed by reading Rich Dad, Poor Dad ([00:03:01]).
• Sales Experience: Entered copier sales at Xerox—struggled with rejection, persistence became a key life lesson ([00:04:03]).
• Building Wealth: Lived far below means, saved aggressively, pushed through “fear” (not analysis paralysis) around his first deal ([00:08:07], [00:09:49]).

3. The Power of Environment and Intentional Networking

• Big Move: Left Portland for Phoenix to “transplant” himself into a thriving, entrepreneurial environment ([00:09:49]).

• Quote [00:10:55]:

  "Before I even landed in Phoenix, I looked up Phoenix entrepreneurs, Arizona entrepreneurs...I went to a networking meetup just so I get surrounded by like-minded people before I even set foot in my own house."
  – Jesse Ray

• Intentional Househacking: Chose roommates who were business professionals or entrepreneurs ([00:12:04]).

4. Building the Growth House Model

• Genesis: First house with ambitious roommates led to demand for more rooms. Missed deal across the street spurred Jesse to door-knock the neighborhood—a “door-to-door” hustle that paid off ([00:13:40]).
• Quote [00:13:40]:

  "Saturday morning, I put my hat on backwards so I don’t look like ADT or pest control, and...pitch: 'I actually am homeless now, ’cause someone rented my house—are you looking to sell?'"
  – Jesse Ray

• Creation of Entrepreneur Homes: Second house acquired, built out the “Growth House” concept—targeting entrepreneur tenants, fostering a culture of support and accountability ([00:15:59], [00:16:24]).

5. From Rental Income to Global Travel

• Financial Freedom: Rental income enabled Jesse to ditch his W2, travel extensively (Cabo, Europe, Brazil, Tulum), and fully focus on business & community ([00:01:21], [00:02:25]).
• Quote [00:07:41]:

  “…for me, the easiest way to start was house hack. That’s why I ended up buying a house out in Phoenix.”
  – Jesse Ray

6. Challenges and Realities of Co-Living

• Headaches: Higher tenant turnover, more personalities, individual leases per room, managing furnished rooms, the need for regular cleaning ([00:36:29]).
• Systems: Regular house cleaners, admin assistant, “house manager,” handyman on call. Strict vetting (“Glass half empty or half full?”) and intentional community-building ([00:37:16], [00:39:25]).
• Quote [00:37:16]:

  "We always have contingency plans...start at 6-12 months per room...”
  – Jesse Ray

7. How He Fills the Houses & Grows the Community

• Cohorts: Initial aim was all-entrepreneur houses; now a mix of professionals and entrepreneurs, with “cohort” periods for deep dives ([00:23:07]).
• Events & Content: Growth House Masterminds (rookies and 7-figure earners), podcasting, content creation, plans for a TV show chronicling the concept ([00:21:56]-[00:25:24]).
• Referral System: Bonuses for tenant referrals, which has become a significant source of new tenants ([00:37:16]).

8. Why Community is Everything

• Central Thesis: Environment is a multiplier. “You become who you surround yourself with” ([00:52:09]).
• Quote [00:27:53]:

  “If we're all matches and you're dim right now, maybe you lost a couple deals…but someone else in the house walks down the stairs that just closed a deal—you get close enough to their lit match, you're going to get lit as well.” – Jesse Ray

9. Growth House Vision & Expansion Plans

• Current State: Three houses in Arizona (Phoenix, Tempe); plans to expand to Dallas, Austin, and other entrepreneurship hubs after refining the model ([00:28:32]).
• Long-term Goal: “Two to three houses in every major entrepreneurial city” ([00:28:32]).

10. Real Numbers: Co-Living House Hack Example

• Breakdown Example:
  • $25K down payment (5%) on $500K house
  • $30K remodel to add a bed/bath, convert carport to casita/ADU
  • PITI ≈ $5,250/month
  • $1,000+/bedroom x 6 rooms + $1,200/casita Airbnb = $7,200/month gross
  • Living for free (as resident) + $1,000/month cash flow; after moving out, $2,000/month net.
• Quote [00:41:52]:

  “You can make at least a thousand to $2,500 a month cash flow…numbers are very conservative…I do more than this on some houses.”
  – Jesse Ray

11. Overcoming Fear: ACTION Over Analysis

• Advice: Five years of “analysis paralysis” is really just fear—shortcut your journey with community, mentors, and coaching ([00:47:01]).
• Quote:

  “Don’t be like me and take five years of analysis paralysis, AKA fear. Go get started.”
  – Jesse Ray

Notable Quotes & Memorable Moments

• On Quitting Corporate for Good ([00:20:47]):

  “I appreciate you guys, but I’m not going to sell myself to you because you can’t afford me.”

• On Networking Intentionally ([00:10:55]):

  “Before seeing the house I just bought… I went to a networking meetup… just so I get surrounded by like-minded people before I even set foot in my own house.”

• On Building Community ([00:52:09]):

  "You become who you surround yourself with."

• Real Estate as a Time-Freedom Vehicle ([00:31:34]):

  “Financial freedom is actually when life starts... now you get to choose who you want to work with, who to partner with, what kind of business you want to run…”

• On Overcoming Hard Things ([00:06:13]):

  “If I do something that every day I wake up, I'm like, this sucks—but train that muscle every day…then everything else in the day is like, okay, I've done worse first thing in the morning.”

Timestamps for Key Segments

• [00:00:21] Jesse’s “I quit” moment and leaving the 9-5 “with authority”
• [00:01:21] Jesse’s post-corporate global travels & lifestyle
• [00:07:41] House-hacking as the entry into real estate
• [00:10:55] Intentionally building a new social/business environment in Phoenix
• [00:13:40] Door-knocking the neighborhood to land a second house
• [00:16:24] Launching “Growth House” and the impact of the first tenants
• [00:19:34] Comparison of corporate “prostituting yourself” vs. being your authentic self
• [00:23:07] House “cohorts” and evolving the model for scale
• [00:28:32] Current footprint and scaling strategy for Growth House
• [00:36:29] The logistics/headaches of co-living, systems, and tenant management
• [00:41:52] Detailed house-hack math and co-living numbers in today’s market
• [00:47:01] Overcoming “analysis paralysis” and importance of community & mentors

Actionable Takeaways

• Don’t Wait for Perfection: Begin with house-hacking, even if it means moving cities. Action and environment are more important than endlessly researching.
• Be Intentional with Your Circle: Curate both your physical living space and your professional networks.
• Co-Living Is for More Than Just Income: It’s a multiplier for growth, mentorship, and opportunity—especially for young, hungry entrepreneurs.
• Optimize for Systems: Use professionals—cleaners, assistants, managers—to keep “freedom” actually free.
• Financial Freedom ≠ Retirement: Use freedom as a springboard for more impactful projects, not an exit from purpose.

Book & Podcast Recommendations

• Book: Passive to Passionate by Brian Lubin
  (“…breaks down what to do when you start, and then after, once you hit that financial freedom.” [00:48:47])
• Podcast: Action Academy Podcast (hosted by Brian Lubin) [00:49:23]

Memorable Stories

• Jesse Living in the Kitchen: “I was remodeling it and living in the kitchen—you know, I sometimes don’t think all the way through on things.” ([00:16:24])
• ‘Undercover Billionaire’ Moment: Door-knocking his own neighborhood led to another property (“I put my hat on backwards so I don’t look like ADT or pest control…” [00:13:40])
• Traveling the World post-FI: From hiking Madeira to running with the bulls and retreating in Tulum ([00:01:21], [00:02:17])

Jesse’s One-Liner Motto

“You become who you surround yourself with.” ([00:52:09])

For more or to connect with Jesse: @thejesseray on Instagram or LinkedIn.

(Summary by Real Estate Investing School Podcast / For educational and reference use. Skip to timestamps for fast-forwarding to discussed segments.)