The Power of ‘Why Not’ W/Donato Callahan
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Episode Description
Welcome to the On The Rise Podcast! In this episode, Jeremy Dyer sits down with Donato Callahan, a 26-year-old real estate entrepreneur who is redefining what early action and intentional learning can create. Donato shares how losing money in the stock market during COVID pushed him to pursue real estate, financial literacy, and ultimately time freedom. From building a PropTech company to sourcing commercial acquisitions and raising capital, Donato explains how momentum, mentorship, and asking “why not” changed his trajectory. This conversation delivers a powerful blueprint for young professionals and investors who want to take control of their future instead of waiting for permission.
Summary
Tip #1: Financial Independence Starts with Control
“The moment I lost half my money overnight, I asked why this was the only path I was taught.”
Donato explains how market volatility exposed the lack of control most people have over their financial future and sparked his pursuit of alternative investing paths.
Tip #2: Not All Financial Advice Is Good Advice
“Advice only works if it’s curated for your situation.”
He emphasizes that blindly following advisors, parents, or peers often leads to misalignment. Investors must understand context before accepting guidance.
Tip #3: Learn from People, Not Textbooks
“Before you start anything, talk to ten people who’ve done it for ten years.”
By stacking decades of experience through conversations, Donato accelerated his learning curve and avoided costly mistakes.
Tip #4: Momentum Beats Perfection
“No one ever got anywhere turning the wheel without hitting the gas.”
Donato credits massive action, even imperfect action, as the primary driver behind his early success.
Tip #5: The Power of ‘Why Not’
“When you ask why, the default answer is no. When you ask why not, the default is action.”
This mindset shift separates people who wait from people who move, especially early in their careers.
Tip #6: Build While Others Pause
“I started my first company during COVID when most people froze.”
Instead of waiting out uncertainty, Donato leaned into opportunity, using disruption as a launchpad.
Tip #7: Networks Create Leverage
“Being in the room puts you closer to the solution.”
Real estate success compounds when relationships create deal flow, capital access, and shared solutions.
Tip #8: Luck Favors Prepared Action
“I sent twelve emails. One changed my life.”
Preparation met opportunity when Donato cold-emailed podcasts, leading to a partnership that altered his career path.
Tip #9: Solve Real Problems with Technology
“I built the tool I needed when I was starting.”
Bright Investor was created to fill a data gap in residential investing by combining analytics, underwriting, and market intelligence into one platform.
Tip #10: Think Long-Term, Not Comfortable
“People who own assets benefit as inflation compounds.”
Donato urges listeners to focus on asset ownership, demographic trends, and positioning themselves where opportunity will exist years from now.
Resources and Links
Website
https://www.donatocallahan.com
Bright Investor
https://www.brightinvestor.com
Social Media
Instagram: @donato_callahan
Email
donato@brightinvestor.com
