Listen to The Confident Investor Podcast: New Episode Every Week

Confident Investor Insights

Cryptocurrency Investing with Brock Pierce, Founder of Blockchain Capital

the confident investor Dec 22, 2020

This week my guest is Brock Pierce, a prolific cryptocurrency investor, and venture capitalist. Brock is considered a pioneer in the digital currency market and has raised more than $5 billion for companies he has founded. He's an early investor in Bitcoin and the Chairman of the Bitcoin Foundation, as well as Founder of Blockchain Capital, Mastercoin, &

His company Blockchain Capital was named the most active FinTech venture fund by PitchBook. He also spearheaded development in the world of internet gaming, with companies like Internet Gaming Entertainment (IGE) and ZAM. Brock was named among the top 20 wealthiest people in the cryptocurrency market by Forbes.

Today we discuss why it’s important to follow your passion instead of money, how to drive impact in everything you do, and how to play the long game as an investor.

Blockchain as the World-Changing Technology

Brock’s passion for blockchain extends far beyond the incredible returns he saw as a...

Continue Reading...

Global Market Trends with Kyle Bass, CIO of Hayman Capital Management

Uncategorized Dec 15, 2020

Have you wondered what drives the richest, most successful investors? What’s that chip on their shoulder that makes them wake up every morning and think “I need to beat yesterday’s returns” again and again. 

Today we’ll be diving into those questions with one of the biggest names in the American banking world, Kyle Bass. Kyle is an  American hedge fund manager, founder and Chief Investment Officer of Hayman Capital Management, a $2.2B dollar Dallas-based hedge fund focused on global events. His investment strategy is focused on finding global macro opportunities that arise when significant events occur that affect our population and economy. 

Kyle’s most famous trade was in 2008 when he successfully predicted and bet against the US housing market in the run-up to the ’08 financial crisis. This one trade made him $500M in profits for his fund. He was also one of the first to raise the possibility that Greece would default on...

Continue Reading...

How to Invest in Real Estate with Janine Yorio, Head of Real Estate at Republic

the confident investor Dec 08, 2020

Janine Yorio is a professional real estate investor who does both personal and institutional deals. She’s Head of Real Estate at Republic and this week on The Confident Investor Podcast, she explains why she’s still bullish on cities, why real estate is like watching golf, how to think about varyings levels of real estate risk, and how to develop confidence as a beginner.

We also discuss different real estate investing options, from fix and flips to new development projects. Janine explains how an Apple store or a Walgreens can revitalize a street to the investor’s benefit, and why crowd-investing is a great choice for new investors who want to start investing in real estate with as little as $100.



Real Estate Investing Is All About Long-Term Thinking


Compared with all the excitement of investing in crypto or the stock market, real estate can seem like watching paint dry. But the fact is, in the best real estate investments, almost nothing...

Continue Reading...

Mission-Driven Investing with Nick Shekerdemian, Founding Partner at The Venture Collective

Investing in startups is often at least a ten-year game, once you put your money in you’re in the journey for the long haul, because when you’re angel investing in a startup, you are coming in at the earliest stages. You’re taking a bet on a founder’s vision at least ten years down the line, and betting that the team today has the competitive advantage to build the company they say they will. 

To be able to invest confidently you need to know the right questions to ask, and you need to feel good about the research and positive signals, so you can create enough conviction that this company will succeed in the future.  

While it’s essential as an investor to consider the long-term financial rewards, more and more investors today are recognizing the importance of also considering the social impact returns of their investments. 

In the future, the fastest-growing startups will be the ones that have a double-bottom line of profit and...

Continue Reading...

How to Find Your Investment Niche with Cheryl Cheng

Cheryl Cheng is a General Partner at BlueRun Ventures and today she shares her experience both as an individual and institutional investor. Before she became a partner at an early-stage venture capital firm, Cheryl developed a keen eye for effective business operations, which she leverages to confidently invest in new companies.

It’s from that perspective that Cheryl shares key skills every investor should bring to the table and advises new investors on how to develop a mutually beneficial relationship with founders.

As an investor, Cheryl is focused on investing specifically in the future of digital health. We discuss the role of passion in investments and how to leverage your skills and expertise to find an investment niche that works for you. 


Combining Business Operations and Investing

Cheryl started her career at an investment bank as a mergers and acquisitions specialist. Her task was to source and evaluate opportunities for early-stage investing. At that...

Continue Reading...

Jesse Middleton on Finding Your 50x Startup Growth Scenario

the confident investor Nov 17, 2020

This week on The Confident Investor Podcast, I’m speaking with Jesse Middleton, a prolific venture capitalist and a General Partner at Flybridge Capital Partners. Jesse was an early executive at WeWork and went on to co-found WeWork Labs. Before he joined Flybridge, Jesse was an active angel investor and in our discussion, he shared advice for all new startup investors.

We also discuss why it’s so important to find startups with strong communities, meet the founders (and what to do if you can’t), and how to diversify your early investments to create the highest potential return for your investment portfolio. 

From a Software Engineer to a Venture Capitalist 

Jesse always knew he would go into tech. He started out as a software engineer in information security and when he moved to New York, he was lucky to get involved in WeWork early on. He co-founded WeWork Labs, and now, he considers that moment to be the beginning of his venture career. 


Continue Reading...

What Makes a Great Investor with Erika Nardini, CEO of Barstool Sports

My guest today is Erika Nardini, the CEO of Barstool Sports, the next-gen sports media brand. Since she arrived in 2016, the revenue has grown 1100% and the company now hires 240 employees. She shares advice for investors from a CEO’s point of view..

In her impressive career, Erika has launched 35+ brands in sports, entertainment, female lifestyle, business, and sports betting. She’s been named Adweek’s most powerful women in the sports businessShe’s passionate about consumer companies and investors who have a true enthusiasm for their products and brands. 

Today we discuss the spirit of winning, the relationship between CEOs and investors, and the makings of a truly great company.

“If you have the stamina to keep growing, that's when things become really exciting.” - Erika Nardini


The Spirit of Winning: Erika’s Leadership Style

As a USA National Champion gymnast, the pro athlete mindset has greatly informed how I...

Continue Reading...

Tim Draper on the Power of Investing without Fear

Tim Draper is a legendary Silicon Valley venture capitalist. His investments include Skype, Hotmail, Tesla SolarCity, and SpaceX. Tim is a true visionary and in this episode, we get to learn from his incredibly rich investment experience.

Tim is also a leading spokesperson for blockchain technology and he has investments in over 50 crypto companies. He created the concept of viral marketing that was instrumental to the success of Hotmail and Skype.

He will tell us how he chooses the startups to invest in, what are the key features of an investment mindset, and how to get over fear and take the first step towards becoming a confident investor.

“If you're not making money, you're not doing anybody any favors.” - Tim Draper


How to Pick the Right Industry 

When it comes to smart investing, you always want to catch the next technological wave. Tim jumped on the internet wave and saw his investments grow as the internet transformed almost every industry in the...

Continue Reading...

How to Become an Angel Investor: The Basics for Beginners

 What is an Angel Investor?

An angel investor is someone who invests his/her personal funds into a startup in the earliest days of the startup’s growth. This is also called seed investing. It's an exciting time to be a startup investor. There are more promising startups than ever before and opportunities to access these investments have finally become available to everyday investors, just like you. 

Angel investors are in the business of finding potential startups to invest in and put in their money before anyone else does. The payoff comes five to ten years down the line when a startup either gets acquired or IPOs. 

Angel investing has traditionally only been reserved for high-net worth individuals… however, that’s all changed. Now you can become an angel investor too. 


What do you mean I can be an Angel Investor?

There’s never been a better time to get into startup investing. Before 2016, angel investing was not an option for an...

Continue Reading...

The 3 Biggest Lies People Believe About Money


Most people believe that all money is created equal, and more money equals more success. 

The truth is all money is not created equal. There's money that works for you, and there's money that works against you. The money that you have in your savings account is just sitting there, doing nothing for you. In fact, you could actually be losing money when the bank savings rate is lower than the inflation rate. 

We all have this illusion of safety, but if you’re not investing money, you’re losing money. This is a fundamental truth that no one ever teaches you. 


Most people think that more money is the end goal

It’s not. More time is the end goal. More freedom is the end goal. Money is simply a means to create more freedom in your life. Most people are a slave to money, to their salaries, and never get off the hamster wheel. 

If you’re working for money, but not making your money work for you, it’s time to...

Continue Reading...

Learn from the best investors in the world