Uploaded January 2022 | Updated September 2026, 3 weeks ago
Today on Dough Roller, we are talking with Robert Leonard! Robert is an expert investor, entrepreneur, and podcast host! He attended University of Massachusetts where he graduated Cum Laude with a BSBA degree in Finance and Economics along with a MBA degree in Accounting and Finance. Robert then became a Certified Management Accountant (CMA) where he practiced as a financial analyst and corporate finance manager. He is an accounting and finance professional with an immense passion for stock and real estate investing, business, and entrepreneurship, which allowed him to quit his W2 position and begin his own real estate investment business.
He is currently the host of two podcasts, Millennial Investing and Real Estate 101 which are under The Investor’s Podcast group where he has recently became VP of growth and innovation. Robert is also a founder and managing partner of Piranha Capital, a boutique real estate investment firm.
In this episode, we talk about Robert’s journey to finance and motocross beginnings. We’ll learn about Robert’s story of his first real estate investment, and how it hooked him into house hacking. We’ll also discuss stock portfolios, bitcoin investment, and rules of thumb for property rental management. If you want to learn more about real estate investing, keep listening!
Episode Highlights:
00:00 - DoughRoller Intro
00:12 - Introducing Robert Leonard
00:42 - Entering the World of Race at 4
02:06 - How Can You Become a Driven Person
03:15 - Why Did Robert Consider Himself as a Black Sheep
04:54 - Getting the Best of Both Worlds
07:17 - Juggling Different Jobs With Time Management
12:09 - Working While in SHS as a Bank Teller
18:30 - Real Estate and House Hacking
24:43 - Where Do You Start When You Wanted to Invest
26:52 - Should You See Real Estate First Before Buying It?
31:04 - How to Know if a Property Is a Good Investment
33:29 - Dealing With Tenants Who Do Not Pay
34:52 - Portfolio on Index Funds, Stocks, and Other Investments
35:42 - Understanding Investment and Bitcoin
38:52 - When Is the Right Time to Buy and Sell in Crypto
43:15 - Building Networks and Scaling Your Business
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The Dough Roller Money Podcast is a finance podcast for easy-to-understand advice on managing your money. How to make it, give it, save it, spend it, and invest it in a way that puts you in control of your money and makes it work for you. This fun, relatable and honest podcast shoots straight and helps people understand the big picture as well as the nuances of owning your finances. From retirement planning, best practices for saving, paying off debt, smart investing and so much more. You don’t have to be a financial expert to listen, but you can become one!
Make sure you SUBSCRIBE so you won't miss any of our upcoming episodes!
➡️ bit.ly/DoughRollerYouTube
#realestate
#realestateinvesting
#realestatetips
Today on Dough Roller, we are talking with Robert Leonard! Robert is an expert investor, entrepreneur, and podcast host! He attended University of Massachusetts where he graduated Cum Laude with a BSBA degree in Finance and Economics along with a MBA degree in Accounting and Finance. Robert then became a Certified Management Accountant (CMA) where he practiced as a financial analyst and corporate finance manager. He is an accounting and finance professional with an immense passion for stock and real estate investing, business, and entrepreneurship, which allowed him to quit his W2 position and begin his own real estate investment business.
He is currently the host of two podcasts, Millennial Investing and Real Estate 101 which are under The Investor’s Podcast group where he has recently became VP of growth and innovation. Robert is also a founder and managing partner of Piranha Capital, a boutique real estate investment firm.
In this episode, we talk about Robert’s journey to finance and motocross beginnings. We’ll learn about Robert’s story of his first real estate investment, and how it hooked him into house hacking. We’ll also discuss stock portfolios, bitcoin investment, and rules of thumb for property rental management. If you want to learn more about real estate investing, keep listening!
Episode Highlights:
00:00 - DoughRoller Intro
00:12 - Introducing Robert Leonard
00:42 - Entering the World of Race at 4
02:06 - How Can You Become a Driven Person
03:15 - Why Did Robert Consider Himself as a Black Sheep
04:54 - Getting the Best of Both Worlds
07:17 - Juggling Different Jobs With Time Management
12:09 - Working While in SHS as a Bank Teller
18:30 - Real Estate and House Hacking
24:43 - Where Do You Start When You Wanted to Invest
26:52 - Should You See Real Estate First Before Buying It?
31:04 - How to Know if a Property Is a Good Investment
33:29 - Dealing With Tenants Who Do Not Pay
34:52 - Portfolio on Index Funds, Stocks, and Other Investments
35:42 - Understanding Investment and Bitcoin
38:52 - When Is the Right Time to Buy and Sell in Crypto
43:15 - Building Networks and Scaling Your Business
------------------------------------------------------------------------------------------------
The Dough Roller Money Podcast is a finance podcast for easy-to-understand advice on managing your money. How to make it, give it, save it, spend it, and invest it in a way that puts you in control of your money and makes it work for you. This fun, relatable and honest podcast shoots straight and helps people understand the big picture as well as the nuances of owning your finances. From retirement planning, best practices for saving, paying off debt, smart investing and so much more. You don’t have to be a financial expert to listen, but you can become one!
Make sure you SUBSCRIBE so you won't miss any of our upcoming episodes!
➡️ bit.ly/DoughRollerYouTube
#realestate
#realestateinvesting
#realestatetips
