logo
episode-header-image
Aug 2021
58m 44s

495: The Science Behind Taking Risks (an...

BIGGERPOCKETS
About this episode
It often seems like the most successful people are the ones who take the most risks. There’s no surprise that at one point, billionaire entrepreneurs were given the choice to either stay where they stood or leap for something greater. This is something that today’s guest, Sukhinder Singh Cassidy, understands. She’s helped lead some of the biggest companies a ... Show More
Up next
Jul 31
How to Analyze a Rental Property Step-by-Step (15 Years of Experience)
This is how to analyze a rental property step-by-step in 2026. You don’t need to do any complicated math, you don’t need to sign up for a course, and you don’t need to have previous rental property experience. I’ve tweaked this process over the past fifteen years of investing to ... Show More
43m 10s
Jul 29
How Much One “Ordinary” Rental Property Has Made Me in the Last 6 Years
Real estate investors often talk about cash flow, or the profits from flipping a house, but rarely the total impact that buying a rental property and holding it for multiple years can have on your net worth. If you’ve never done the math, it’s significant. In many cases, a single ... Show More
34m 23s
Jul 27
The “Repeatable” Strategy That Helped Him Buy 6 Rentals in 6 Months (Working a W-2)
Worried you’ll come up short in retirement? When Brian Waters ran the numbers, he realized he was still decades away from being able to leave his nine-to-five. He needed a lifeline, and he found one in real estate investing. In just five years, he has scaled to 20 rental properti ... Show More
38m 4s
Recommended Episodes
Aug 2021
Building Wealth, Overcoming Failure & Rethinking Risk Taking w/ Sukhinder Singh Cassidy EP 1150
<p>Today's guest is Sukhinder Singh Cassidy. For more than 25 years, she’s been a leading tech entrepreneur and CEO who’s grown, scaled, and advised for companies like StubHub, Google, Amazon, and more. She’s currently the Founder and Chairman of theBoardlist, a talent marketplac ... Show More
1h 29m
Apr 2025
Ready to take the leap? This is the home for bold risk-takers and aspiring entrepreneurs.
What’s the boldest risk you’ve ever taken? For entrepreneurs, risk is the heart of the journey. In our newest season of This is Small Business, host Andrea Marquez takes you behind the scenes with founders who’ve turned "maybe one day" into "let’s do this!" Join Andrea as she dig ... Show More
2m 52s
Aug 2021
Ep. 996: Sukhinder Singh Cassidy Interview with Michael Covel on Trend Following Radio
<p>My guest today is Sukhinder Singh Cassidy, a leading technology executive and entrepreneur, board member, and investor with twenty-five years of experience founding and helping to scale companies, including Google and Amazon. Most recently, she served as president of StubHub a ... Show More
49m 27s
Apr 2025
To Make Better Decisions, Think Like a Venture Capitalist
Venture capital firms notoriously embrace risk and take big swings, hoping that one startup will become a monster hit that pays for many other failed investments. This VC approach scares established companies, but it shouldn’t. Stanford Graduate School of Business professor Ilya ... Show More
24m 44s
Jul 2022
2 Types of Business Risk | Ep 413
It's risky business, people! Today, Alex (@AlexHormozi) talks about the top business risks that are made by many new entrepreneurs, show you how each risk works (with different scenarios played out), the best ways to approach these, and how the wealthiest figure out ways to play ... Show More
17m 46s
May 2024
What Venture Capitalists Can Teach Companies About Decision-Making
Venture capital firms notoriously embrace risk and take big swings, hoping that one startup will become a monster hit that pays for many other failed investments. This VC approach scares established companies, but it shouldn’t. Stanford Graduate School of Business professor Ilya ... Show More
27m 4s
Feb 2025
Forget the corporate ladder — winners take risks | Molly Graham
Success in your career looks different for everyone — but no matter your industry, you'll need to take risks. Company and community builder Molly Graham shares three key skills to learn before jumping off the metaphorical cliff, outlining a path off the corporate ladder and into ... Show More
12m 8s
Apr 2024
A Roadmap for Today’s Entrepreneurs
Many people aspire to entrepreneurship but we all know it's a high-risk endeavor. Bill Aulet, the Ethernet Inventors Professor of Entrepreneurship at the MIT Sloan School of Management, has for decades studied what it takes for start-ups to succeed and advises the next generation ... Show More
27m 14s
Nov 2023
The Bridge to Billion: Navigating Towards Business Success (on The Life Coach School) Pt.1 - July ‘22 | Ep 92
Get the unfiltered memos I send my team as we scale Acquisition.com to $1B+: Leila's Letters 
28m 42s
Jun 2023
Exploring the Major Pitfalls (and Wins) in Business
Today, we’ll hear about: •       The best way to transition leadership in family business •       Vic Keller’s tactics to his entrepreneurial success •       A caller with an enormous amount of risky business debt •       The questions you need to ask yourself when deciding betwe ... Show More
49m 41s