Podcast Summary: "Fail Forward: Ari Rastegar on Lessons That Built an Empire in Austin"

The Mello Millionaire with Tommy Mello
Episode Date: October 3, 2025
Guest: Ari Rastegar (Founder & CEO, Rastegar Capital)
Theme: Building, Scaling, and Learning from Failure on the Road to Real Estate Success

Episode Overview

In this episode, Tommy Mello sits down with Ari Rastegar—widely called the “Oracle of Austin”—to delve into the real, gritty lessons behind building a multi-billion-dollar real estate portfolio from humble beginnings. With a focus on resilience, contrarian thinking, and the crucial role of relationships, Ari shares insights on failing forward, reading deeply, and designing a life of meaningful achievement beyond money.

Key Discussion Points & Insights

Embracing Failure and the Truth About Success

• Ari opens with raw honesty about his relationship to failure, noting, "The only thing that I've got really good at at this point in my life is failing. And I promised myself...if I ever got to the other side, I would tell the truth." [00:00]
• Failure as a catalyst: “To me, failure is learning how to win.” [00:42, Ari]
• Action and inertia are at the core, as Ari insists, “All success is about inertia, is about action.” [00:27, Ari]

Humble Beginnings: From Speech Impediment to CEO

• Ari recounts his challenging youth—struggles with a speech impediment, community college, pizza delivery jobs, and pressure as the child of Iranian immigrants. [02:04]
  • “My dad said, you know, being an Iranian immigrant and having the dictatorial, typical Iranian father said, after you become a lawyer, you can be an exotic dancer for all I care.” [02:07, Ari]
• Law school hustle: Building his first houses using scholarship money and cold-calling local builders. [02:47]

Building Community and the Real Value of Real Estate

• Transitioning from law to real estate: "Building community is really what, is really what I love." [03:11, Ari]
• Portfolio scale: Over 38 cities, 13 states, nearly every asset class, with projected value over $10 billion—and “I own 100% of the company. I never took corporate capital at the corporate level.” [04:19, Ari]

Strategy: Singles & Doubles, Not Home Runs

• Risk philosophy: Focused on “singles and doubles” (16–18% IRR) rather than risking everything for huge returns:
  • “We’re not looking to make huge returns, because making huge returns means you took a huge amount of risk, a hundred percent.” [04:52, Ari]

The Power (and Tedium) of Cold Calling

• Ari describes early hustle: 50–70 cold calls a day to build relationships, with cold calls lasting “three to five seconds.” The grind pays off with that one breakthrough. [05:39-06:33]

Building Relationships: Serendipity by Design

• Ari’s networking hacks: Becoming a regular at Il Molino in NYC—befriending staff, creating ‘serendipitous’ introductions to connect with movers and shakers. [06:41]
• On empathy and true friendship: “Once you have commonality, you have empathy. And when you have empathy, you have everything.” [07:50, Ari]

Money is a Tool, Not the Goal

• Ari reflects: “Money is a tool. Money is a catalyst. Money on its own is absolutely worthless...I’ve made money. I’ve lost money...but it’s the way it moves through your hands.” [09:45, Ari]

The Value of Deep Reading

• Both Ari and Tommy share the books that shaped them:
  • Tommy: “The E-Myth Revisited,” “Richest Man in Babylon,” “Ultimate Sales Machine” [10:29]
  • Ari: Advocates novels as mind-expanders. “I have found there to be more substance and more expansion in reading the best novels in the world than reading any of the personal development books.” [11:03, Ari]
  • Top recommendations: “100 Years of Solitude,” “Moby Dick,” Dostoevsky, Chekhov, Dickens [12:09, Ari]

Time, Compounding, & the False Scarcity of Youth

• Advice to his 20-year-old self: “Time is much more limited than, than I treated it at the time...Looking back...the small little bits of effort...could have turned into strategic delegation much earlier.” [13:11, Ari]
• Warren Buffett as proof: “He wasn’t a billionaire to 65 years old...the greatest thing he ever did is live to 95.” [13:11, Ari]

If He Started Over with $10 Million

• “I would spend at least a year traveling the world...to awaken parts within me that had not been awakened. And then from that place, be comfortable walking into the unknown...” [14:46, Ari]

On Negativity and Social Media

• “Only miserable people do that,” Ari says on online negativity. He reveals past struggles with anger and entitlement, rooted in family trauma from fleeing Iran. [15:57, Ari]

Seeing the Future: Austin, Storage, and Human Nature

• On his reputation for spotting trends: “I wish I could tell you I was as clairvoyant then as it has appeared to be…people have certain core values...Water is one of them, nature is one...We’re amazingly similar, repetitive, and predictable.” [16:55, Ari]
• Guiding principle: “Keep things as simple as possible, but no simpler.” [17:56, Ari]

Technology and the Fourth Industrial Revolution

• “AI is the new electricity...not a separate thing, but an underpinning catalyst for everything that follows.” [19:06, Ari]
• Believes this is “the most interesting and exciting time to ever be alive...technology at its best is an extension of humanity.” [20:39, Ari]

Rapid Fire: Concrete Lessons and Favorite Books

• On real estate books: Recommends “Rich Dad, Poor Dad” and “Think and Grow Rich,” but again pushes for great novels to expand possibility. [20:48]
• Most expensive lesson: “The astronomical price of procrastination.” [22:00, Ari]
• Sun Belt vs. Coastal Cities: Sun Belt is the best 7–9 year bet, but “there is a gravitational pull quite literally to the coast...the whole universe is inside of you, quite literally.” [22:15-23:32, Ari]

Ari’s Book: "The Gift of Failure"

• “The first line of the book is, I hope you fail. I hope you fail a lot. That’s all I’ve known how to do.” [23:34, Ari]

Noteworthy Quotes & Memorable Moments

• Ari Rastagar on failure:
  “I hope you fail. I hope you fail a lot. That’s all I’ve known how to do.” [23:34]
• On money:
  “Money on its own is absolutely worthless. It’s a tool...I’ve had billions and billions of dollars go through my hands throughout my career. And I’m just getting started.” [09:45]
• On empathy:
  “Once you have commonality, you have empathy. And when you have empathy, you have everything.” [07:50]
• On procrastination:
  “The astronomical price of procrastination.” [22:00]
• On time and youth:
  “Time is much more limited than I treated it at the time.” [13:11]
• On authenticity in relationships:
  “Building really authentic relationships is a text message a couple times a week...versus some grandiose gesture.” [08:54]
• On AI/technology:
  “AI is the new electricity.” [19:06]
• On opportunity:
  “This is the most interesting and exciting time to ever be alive for so, so many reasons.” [20:39]

Timestamps for Key Segments

• [00:00] – Ari on failure as the other side of success
• [02:04] – Ari’s unlikely journey from community college to CEO
• [04:19] – Building a $10 billion portfolio solo
• [04:52] – Risk, IRR targets, and “singles and doubles”
• [05:39] – “That one cold call” that changed his life
• [06:41] – Networking hacks and building relationship capital
• [09:45] – Money as a catalyst, not a goal
• [11:03] – Why great novels beat business self-help books
• [13:11] – Advice to his 20-year-old self about time
• [14:46] – What Ari would do with $10 million today
• [15:57] – Ari on overcoming anger, entitlement, and family legacy
• [16:55] – Reading human nature, Austin’s growth, investing cycles
• [19:06] – Ari’s perspective on artificial intelligence
• [20:48] – Top recommendations: Real estate books and novels
• [22:00] – Hardest/Earliest lesson: price of procrastination
• [22:15] – Sun Belt vs. Coastal cities
• [23:34] – Ari’s book title and philosophy on embracing failure
• [24:13] – Closing advice: “Sit in divine silence and listen”

Closing Reflection

Ari leaves listeners with a call to unplug from noise and lean into moments of silence:
“Close your eyes for a second and sit in that divine silence and listen.” [24:37]

In summary, this episode is a masterclass in failing forward, intentional relationship-building, and the art of consistent, compounding effort over a lifetime—delivered with humility, wit, and the rebel spirit that built an empire in Austin.

Recommended For: Anyone seeking raw, practical wisdom on achieving long-term wealth, leadership through adversity, and finding deeper meaning behind entrepreneurial success.