The Code To Winning – EP069

"$50,000 DEAL CHANGED EVERYTHING: THE BLUEPRINT TO REAL ESTATE FREEDOM"
Guest: Jamil Damji
Host: Kagiso Dikane
Date: November 7, 2025

Episode Overview

This episode of The Code To Winning features Jamil Damji, an internationally acclaimed real estate investor and educator, best known as co-founder of Keighley (Kegley) and the visionary behind Astro Flipping. Jamil shares his unconventional journey into real estate, the pivotal $50,000 wholesale deal that changed his life, lessons from losing millions in the 2008 crash, and the core philosophies that now underpin both his entrepreneurial approach and mentorship. With raw honesty, he discusses the critical importance of integrity, building collaborative networks, and elevating the standards in an industry often criticized for lack of transparency. For aspiring and established entrepreneurs alike, this conversation is packed with practical strategies, cautionary tales, and empowering mindsets for winning – in business and in life.

Key Discussion Points & Insights

1. Origins: From “Failed Doctor” to Accidental Real Estate Mogul

Jamil’s Background & Family Expectations
- Grew up in an Indian family where success meant becoming a doctor or engineer
- Struggled academically despite high grades because he lacked genuine passion for medicine
- “...I wasn't authentically a doctor... I'm grateful that whoever it was that made the decision that said no to me did that because my life is so much better than it would have been if I was a doctor.” — Jamil [06:46]
Early entrepreneurial pursuits included taking over a failing internet company at 21 (“sold more websites in one week than they had in a quarter”) [10:07], only to discover zero margins.

2. The First Wholesale Deal: A $50,000 Paradigm Shift ([13:06]-[16:41])

The Pivotal ‘For Rent’ Sign
- Spotted a property he'd tried to rent months prior; after extended vacancy, asked the owner if she’d sell
- Negotiated a $350k sale price, then found a buyer willing to pay $400k
Discovering Transactional Engineering
- With no capital, cold-called attorneys for advice.
- Attorney David Steed introduces the ‘skip transfer’ (now known as contract assignment/wholesaling):
  - “You want to do what's called a skip transfer… What you're going to need is two contracts… you're going to buy the property for 350,000… On the second contract, you're going to be the seller and you're going to have the $400,000 price. So you're going to buy it for 350, you're going to sell for 400. Everything else on those contracts has to match.” — Attorney advice, paraphrased by Jamil [15:23]
Fear & Scarcity After Windfall
- “I have this cashier's check that I'm fearful of cashing. I didn't cash that thing for months... I was fearful. I was still living in lack... guarding that 50,000 with my life.” — Jamil [16:41]
- That deal becomes the catalyst to systematize finding off-market opportunities via ‘for rent’ ads.

3. The Rise—and Fall—of a Young Millionaire ([18:14]-[23:21])

Scaling Up
- Repeated the process, flipping properties and small apartment buildings—“For a few years, just stacked money… ended up a millionaire in my 20s.”
2008 Crash & Humbling Loss
- Bought into deals himself to “level up,” overleveraged, and the financial crisis wiped him out:
  - “…I lost all of those buildings. I was negative $1.8 million at the end of it.” [21:54]
- Reflections on Canadian vs. US banking systems and how foreclosure worked differently [22:23]

4. Reinvention: Laughter, Family, and a New Real Estate Chapter ([24:02]-[30:59])

Flees into stand-up comedy in LA to recover emotionally.
Sister saves family assets back in Canada, turning two ‘joke’ properties into nearly $1 million via reinvestment and sober living projects [26:25]
Jamil returns to real estate out of financial necessity after proposing to his wife, leveraging Phoenix’s depressed post-crash market:
- “...in Phoenix you could buy these condominiums for, like, $25,000... and they were renting for, like, 800 bucks a month.” [27:55]
- Rediscovers wholesaling through Craigslist, wholesales two short-sale contracts to a cash buyer in minutes, and recognizes his unique skillset [29:45]
- “I have this skill set that can make tens of thousands of dollars and I'm able to literally do this in my sleep… what am I doing?” [30:26]
- Marks 12-12-12 (December 12, 2012) as the rebirth: moving from LA to Phoenix to begin again [30:44]

5. Building Keighley: From Anonymity to Industry Leadership ([31:58]-[43:31])

Avoids attention due to past trauma, operates as ‘secret weapon’ for local realtors, builds reputation for reliably closing deals
Partnership formation origin story:
- Young hustlers Josiah Grimes and Hunter Runyon show their worth by quickly selling Jamil’s deals—“Who the hell are these two kids?” [36:08]
- Impressed by their systems/tech, writes a check for $1 million—birth of national venture Keighley (Kegley) [37:24]
- Keighley’s value: Dispositions as a service, building large “buyers lists” efficiently, enabling reliable closing for other wholesalers [37:55]
- Elevates industry standards—“We wanted to help wholesalers fulfill their promises… Keighley became successful because that was a massive problem.” [41:39]
Insight on industry’s transparency problem:
- “Wholesalers will put a seller under contract, put $10 EMD down... not close, file a memorandum, and the seller goes and packs all their things in a U Haul... and no one’s closing...” [39:03]
- “The lack of transparency is just irrefutable... I don’t believe in lying.” [40:38]

6. The Power of Collaboration: Pace Morby Partnership & Industry Abundance ([43:55]-[51:18])

Organic partnership with Pace Morby forged over mutual adversity—helped Pace through a Ponzi scheme perpetrated by a local investor
Healthy competition & collaboration as a business edge:
- “I didn’t care if Pace beat me on a deal... If there was a resource I had that he needed, I’d give it to him... That defines healthy competition...” [50:06]
- Led to “Pace and Jamil Does America”—a grassroots movement growing from 13 to 1,300 attendees at meetups [51:18]

7. The Heart of Sustainable Success: Integrity, Energy, and Frequency ([51:50]-[68:03])

Host probes on how to ensure integrity in a sales industry prone to cutting corners:
- “I really do believe that... I've tapped into a frequency... there's transparency, there's truth, there's honor, there is love... Your life is being lived on the inside out...” [52:16]
- “Money, my friend, is an energy and there's a frequency to it. And if you can tap into that frequency, then abundance is impossible not to have; you are abundance.” [53:02]
- “To be happy, to walk away from a few extra bucks if it means keeping your integrity intact, that's powerful...” [54:23]
Memorable Story: The ‘No Wasted People’ Donut/Indian Food Miracle ([59:03]-[66:53])
- Jamil recounts a story (inspirational and layered) about a string of small, seemingly random acts of kindness leading to a powerful, undeniable coincidence—a prayer answered to the minute via an Indian food delivery to a homeless woman, instilling the message that “there are no wasted people, there are no wasted moments ever.” [66:55]

Notable Quotes & Memorable Moments

On Perspective Shifts & Opportunity

“Most people would go into that meeting and say, I can buy this house for $350,000, which… would be the normal thing to do. But my mind didn’t work like that. I went in and I said, hey, here’s an address of a lady who’s interested in selling her house. What would you pay for that?... So now I have a $50,000 problem to solve, because I can buy the house for 350 grand. I can sell the house for 400 grand, and I don’t have any money. What do I do?”
— Jamil Damji [00:40]

On Scarcity and Abundance

“I didn’t cash that thing for months, bro. I folded it up, I put it in my wallet and I just walked around with it... I was fearful. I was still living in lack... I didn’t think that that could happen again.”
— Jamil Damji [16:41]

On Integrity in Real Estate

“The lack of transparency is just irrefutable. And so that along with all of the unfulfilled promises that sellers have had with wholesalers is the reason why we built Keighley. Because we wanted to… help wholesalers fulfill in their promises. If you're going to go contract a house with a seller, we're going to help you sell that deal. Because the reputation of this industry is being tarnished by people who are just walking away.”
— Jamil Damji [41:39]

On Collaboration

“That defines healthy competition as well. Amazing competing... But you're still collaborating and working together—lifting, which is the entire purpose of what competitions are meant to do.”
— Kagiso Dikane [50:12]

On Integrity and Energy

“I don't believe my success is because I'm really good at wholesaling. I think that I've tapped into a frequency and in that frequency there is transparency, there's truth, there's honor, there is love... I have to be inside what I am outside. And that's why you see the integrity.”
— Jamil Damji [52:16]

On Miracles and Every Moment Counting

“There are no wasted people. There are no wasted moments ever.”
— Jamil Damji [66:55]

On Winning

“Winning to me is living what I am inside every day. Having a life where I get to live what I am inside truly, authentically, every moment.”
— Jamil Damji [67:38]

Timestamps for Important Segments

[00:40] — The $50,000 “Skip Transfer” deal that began it all
[16:21] — Paradigm shift & fear after receiving the check
[21:54] — Losing $12 million in the 2008 crash
[29:45] — Returning to real estate through Craigslist
[37:24] — Founding Keighley with new partners
[41:39] — The ethics problem in wholesaling & how Keighley addressed it
[50:06] — Collaboration and healthy competition with Pace Morby
[52:16] — The real secret to success: energy, frequency, and integrity
[59:03-66:53] — The Portland ‘donut’/Indian food miracle: “There are no wasted people”
[67:38] — Jamil’s definition of ‘winning’

Further Resources & Contact

Instagram: @jdamji
YouTube: Jamil Damji
Keighley and Astro Flipping: See episode links for programs and courses

Final Takeaway

This episode is a masterclass in creative real estate, resilience, the importance of executing with integrity, and the courage to trust-fueled collaboration over scarcity. Jamil’s journey from “broke kid with a phone” to industry leader is packed with practical strategies, cautionary wisdom, and deeply human stories that underscore his code to winning: live authentically from the inside out, and trust that no act or moment is ever wasted.

The Code To Winning – EP069

"$50,000 DEAL CHANGED EVERYTHING: THE BLUEPRINT TO REAL ESTATE FREEDOM"
Guest: Jamil Damji
Host: Kagiso Dikane
Date: November 7, 2025

Episode Overview

Key Discussion Points & Insights

1. Origins: From “Failed Doctor” to Accidental Real Estate Mogul

Jamil’s Background & Family Expectations
- Grew up in an Indian family where success meant becoming a doctor or engineer
- Struggled academically despite high grades because he lacked genuine passion for medicine
- “...I wasn't authentically a doctor... I'm grateful that whoever it was that made the decision that said no to me did that because my life is so much better than it would have been if I was a doctor.” — Jamil [06:46]
Early entrepreneurial pursuits included taking over a failing internet company at 21 (“sold more websites in one week than they had in a quarter”) [10:07], only to discover zero margins.

2. The First Wholesale Deal: A $50,000 Paradigm Shift ([13:06]-[16:41])

The Pivotal ‘For Rent’ Sign
- Spotted a property he'd tried to rent months prior; after extended vacancy, asked the owner if she’d sell
- Negotiated a $350k sale price, then found a buyer willing to pay $400k
Discovering Transactional Engineering
- With no capital, cold-called attorneys for advice.
- Attorney David Steed introduces the ‘skip transfer’ (now known as contract assignment/wholesaling):
  - “You want to do what's called a skip transfer… What you're going to need is two contracts… you're going to buy the property for 350,000… On the second contract, you're going to be the seller and you're going to have the $400,000 price. So you're going to buy it for 350, you're going to sell for 400. Everything else on those contracts has to match.” — Attorney advice, paraphrased by Jamil [15:23]
Fear & Scarcity After Windfall
- “I have this cashier's check that I'm fearful of cashing. I didn't cash that thing for months... I was fearful. I was still living in lack... guarding that 50,000 with my life.” — Jamil [16:41]
- That deal becomes the catalyst to systematize finding off-market opportunities via ‘for rent’ ads.

3. The Rise—and Fall—of a Young Millionaire ([18:14]-[23:21])

Scaling Up
- Repeated the process, flipping properties and small apartment buildings—“For a few years, just stacked money… ended up a millionaire in my 20s.”
2008 Crash & Humbling Loss
- Bought into deals himself to “level up,” overleveraged, and the financial crisis wiped him out:
  - “…I lost all of those buildings. I was negative $1.8 million at the end of it.” [21:54]
- Reflections on Canadian vs. US banking systems and how foreclosure worked differently [22:23]

4. Reinvention: Laughter, Family, and a New Real Estate Chapter ([24:02]-[30:59])

Flees into stand-up comedy in LA to recover emotionally.
Sister saves family assets back in Canada, turning two ‘joke’ properties into nearly $1 million via reinvestment and sober living projects [26:25]
Jamil returns to real estate out of financial necessity after proposing to his wife, leveraging Phoenix’s depressed post-crash market:
- “...in Phoenix you could buy these condominiums for, like, $25,000... and they were renting for, like, 800 bucks a month.” [27:55]
- Rediscovers wholesaling through Craigslist, wholesales two short-sale contracts to a cash buyer in minutes, and recognizes his unique skillset [29:45]
- “I have this skill set that can make tens of thousands of dollars and I'm able to literally do this in my sleep… what am I doing?” [30:26]
- Marks 12-12-12 (December 12, 2012) as the rebirth: moving from LA to Phoenix to begin again [30:44]

5. Building Keighley: From Anonymity to Industry Leadership ([31:58]-[43:31])

Avoids attention due to past trauma, operates as ‘secret weapon’ for local realtors, builds reputation for reliably closing deals
Partnership formation origin story:
- Young hustlers Josiah Grimes and Hunter Runyon show their worth by quickly selling Jamil’s deals—“Who the hell are these two kids?” [36:08]
- Impressed by their systems/tech, writes a check for $1 million—birth of national venture Keighley (Kegley) [37:24]
- Keighley’s value: Dispositions as a service, building large “buyers lists” efficiently, enabling reliable closing for other wholesalers [37:55]
- Elevates industry standards—“We wanted to help wholesalers fulfill their promises… Keighley became successful because that was a massive problem.” [41:39]
Insight on industry’s transparency problem:
- “Wholesalers will put a seller under contract, put $10 EMD down... not close, file a memorandum, and the seller goes and packs all their things in a U Haul... and no one’s closing...” [39:03]
- “The lack of transparency is just irrefutable... I don’t believe in lying.” [40:38]

6. The Power of Collaboration: Pace Morby Partnership & Industry Abundance ([43:55]-[51:18])

Organic partnership with Pace Morby forged over mutual adversity—helped Pace through a Ponzi scheme perpetrated by a local investor
Healthy competition & collaboration as a business edge:
- “I didn’t care if Pace beat me on a deal... If there was a resource I had that he needed, I’d give it to him... That defines healthy competition...” [50:06]
- Led to “Pace and Jamil Does America”—a grassroots movement growing from 13 to 1,300 attendees at meetups [51:18]

7. The Heart of Sustainable Success: Integrity, Energy, and Frequency ([51:50]-[68:03])

Host probes on how to ensure integrity in a sales industry prone to cutting corners:
- “I really do believe that... I've tapped into a frequency... there's transparency, there's truth, there's honor, there is love... Your life is being lived on the inside out...” [52:16]
- “Money, my friend, is an energy and there's a frequency to it. And if you can tap into that frequency, then abundance is impossible not to have; you are abundance.” [53:02]
- “To be happy, to walk away from a few extra bucks if it means keeping your integrity intact, that's powerful...” [54:23]
Memorable Story: The ‘No Wasted People’ Donut/Indian Food Miracle ([59:03]-[66:53])
- Jamil recounts a story (inspirational and layered) about a string of small, seemingly random acts of kindness leading to a powerful, undeniable coincidence—a prayer answered to the minute via an Indian food delivery to a homeless woman, instilling the message that “there are no wasted people, there are no wasted moments ever.” [66:55]

Notable Quotes & Memorable Moments

On Perspective Shifts & Opportunity

“Most people would go into that meeting and say, I can buy this house for $350,000, which… would be the normal thing to do. But my mind didn’t work like that. I went in and I said, hey, here’s an address of a lady who’s interested in selling her house. What would you pay for that?... So now I have a $50,000 problem to solve, because I can buy the house for 350 grand. I can sell the house for 400 grand, and I don’t have any money. What do I do?”
— Jamil Damji [00:40]

On Scarcity and Abundance

“I didn’t cash that thing for months, bro. I folded it up, I put it in my wallet and I just walked around with it... I was fearful. I was still living in lack... I didn’t think that that could happen again.”
— Jamil Damji [16:41]

On Integrity in Real Estate

“The lack of transparency is just irrefutable. And so that along with all of the unfulfilled promises that sellers have had with wholesalers is the reason why we built Keighley. Because we wanted to… help wholesalers fulfill in their promises. If you're going to go contract a house with a seller, we're going to help you sell that deal. Because the reputation of this industry is being tarnished by people who are just walking away.”
— Jamil Damji [41:39]

On Collaboration

“That defines healthy competition as well. Amazing competing... But you're still collaborating and working together—lifting, which is the entire purpose of what competitions are meant to do.”
— Kagiso Dikane [50:12]

On Integrity and Energy

“I don't believe my success is because I'm really good at wholesaling. I think that I've tapped into a frequency and in that frequency there is transparency, there's truth, there's honor, there is love... I have to be inside what I am outside. And that's why you see the integrity.”
— Jamil Damji [52:16]

On Miracles and Every Moment Counting

“There are no wasted people. There are no wasted moments ever.”
— Jamil Damji [66:55]

On Winning

“Winning to me is living what I am inside every day. Having a life where I get to live what I am inside truly, authentically, every moment.”
— Jamil Damji [67:38]

Timestamps for Important Segments

[00:40] — The $50,000 “Skip Transfer” deal that began it all
[16:21] — Paradigm shift & fear after receiving the check
[21:54] — Losing $12 million in the 2008 crash
[29:45] — Returning to real estate through Craigslist
[37:24] — Founding Keighley with new partners
[41:39] — The ethics problem in wholesaling & how Keighley addressed it
[50:06] — Collaboration and healthy competition with Pace Morby
[52:16] — The real secret to success: energy, frequency, and integrity
[59:03-66:53] — The Portland ‘donut’/Indian food miracle: “There are no wasted people”
[67:38] — Jamil’s definition of ‘winning’

Further Resources & Contact

Instagram: @jdamji
YouTube: Jamil Damji
Keighley and Astro Flipping: See episode links for programs and courses

$50,000 DEAL CHANGED EVERYTHING: THE BLUEPRINT TO REAL ESTATE FREEDOM || JAMIL DAMJI || EPISODE 069

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Summary

The Code To Winning – EP069

Episode Overview

Key Discussion Points & Insights

1. Origins: From “Failed Doctor” to Accidental Real Estate Mogul

2. The First Wholesale Deal: A $50,000 Paradigm Shift ([13:06]-[16:41])

3. The Rise—and Fall—of a Young Millionaire ([18:14]-[23:21])

4. Reinvention: Laughter, Family, and a New Real Estate Chapter ([24:02]-[30:59])

5. Building Keighley: From Anonymity to Industry Leadership ([31:58]-[43:31])

6. The Power of Collaboration: Pace Morby Partnership & Industry Abundance ([43:55]-[51:18])

7. The Heart of Sustainable Success: Integrity, Energy, and Frequency ([51:50]-[68:03])

Notable Quotes & Memorable Moments

On Perspective Shifts & Opportunity

On Scarcity and Abundance

On Integrity in Real Estate

On Collaboration

On Integrity and Energy

On Miracles and Every Moment Counting

On Winning

Timestamps for Important Segments

Further Resources & Contact

Final Takeaway

Summary

The Code To Winning – EP069

Episode Overview

Key Discussion Points & Insights

1. Origins: From “Failed Doctor” to Accidental Real Estate Mogul

2. The First Wholesale Deal: A $50,000 Paradigm Shift ([13:06]-[16:41])

3. The Rise—and Fall—of a Young Millionaire ([18:14]-[23:21])

4. Reinvention: Laughter, Family, and a New Real Estate Chapter ([24:02]-[30:59])

5. Building Keighley: From Anonymity to Industry Leadership ([31:58]-[43:31])

6. The Power of Collaboration: Pace Morby Partnership & Industry Abundance ([43:55]-[51:18])

7. The Heart of Sustainable Success: Integrity, Energy, and Frequency ([51:50]-[68:03])

Notable Quotes & Memorable Moments

On Perspective Shifts & Opportunity

On Scarcity and Abundance

On Integrity in Real Estate

On Collaboration

On Integrity and Energy

On Miracles and Every Moment Counting

On Winning

Timestamps for Important Segments

Further Resources & Contact

Final Takeaway