How to Lose Money: Business Stories | Life Lessons | Navigating Failure-logo

How to Lose Money: Business Stories | Life Lessons | Navigating Failure

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169: How to Lose Money by Raising a $50 Million Real Estate Fund with Mark Mascia

Mark Mascia has had over 17 years of real estate investment experience and a career portfolio valued at over $2 billion. Mark founded Mascia Development, LLC in 2006. Prior to becoming an entrepreneur, Mark oversaw half a billion dollars in development projects in Manhattan while he worked for Archstone, a former Fortune 500, publicly traded real estate company. From early on, Mark has been working closely with some of the country’s wealthiest family offices and continues to do so today with...


168: How to Lose Money by Not Checking Your Spam Email with James Kandasamy

James Kandasamy is the principal at Achieve Investment Group, a vertically integrated investment company actively engaged in multifamily acquisition, asset management, property and construction management. A well-known multifamily operator, James has over 4 years of multifamily experience, and 6 plus years of experience in real estate overall. In addition to his work, James has built a reputation for creative marketing tactics to find motivated sellers and unlock hidden value in multifamily...


167: How to Lose Money by Surviving Hurricane Katrina with Anna Myers

Anna Myers is the vice president of Grocapitus Investments, LLC, teaches underwriting for MultifamilyU, and co-hosts a real estate investor meet-up in the San Francisco Bay area. With an extensive background as a programmer in systems architect in the tech industry, she uses these skills to evaluate multifamily deals, identify key investment markets, and implement systems and processes to acquire and manage multifamily assets. Anna partnered with Neal Bawa to purchase 500 units of apartment...


166: How to Lose Money by Saying "No" on Shark Tank with Maneesh Sethi

Maneesh is the founder of Pavlok and Shock Clock, helping people change their habits for good. In 2008, Maneesh took a two year break from studying at Stanford to travel and start, a travel blog about credit card hacking and digital nomads. In 2012, his article, “Why I Hired a Girl on Craigslist to Slap Me in the Face- And How it Quadrupled my Productivity”, went viral. In 2013, he took that idea to start a company that earned almost 8 figures in revenue over the last...


165: How to Lose Money by Buying Cheap with Vinney Chopra

Vinney Chopra’s success in real estate investment and syndication is a testament to the power of enthusiasm, passion, persistence and positivity. He came to the United States from India over 40 years ago. He had only seven dollars in his pocket, but he knew without a doubt that the opportunities offered by this country were within reach because he had a vision for his life plus the commitment to learn, work hard and sacrifice to achieve his goals. He has successfully completed 27 multifamily...


164: How to Lose Money by Buying Apartments in the Sticks with Fernando Angelucci

Fernando Angelucci is the 27-year-old senior managing partner of Titan Wealth Group based out of Chicago. He first read Rich Dad, Poor Dad when he was 16 and subsequently started his first business at the age of 19 while attending the University of Illinois at Urbana-Champaign. When Fernando graduated with a bioengineering AG degree in 2013, he went on to work in a Fortune 50 company and immediately started investing in single family homes on the side. By the age of 23, he was able to...


163: How to Lose Money by Not Vetting Your Partners with Adam Adams

Adam started investing in real estate in 2005 after repositioning his first apartment community in 2007 from a $2 million value to a $4 million value in 12 months as a property manager. Adam bought his first multifamily apartment building. Since then, Adam has managed several single family “fix-and-flips” and holds over 100 multifamily rental doors. Adam is the organizer of Colorado’s most active real estate group, and he hosts the "Creative Real Estate Podcast”. Adam has been a guest on...


162: How to Lose Money by Trying to Do it All Yourself with Jason Hull

Jason Hull’s personal mission statement is to inspire others to love true principles. This means he’s all about figuring out what works and sharing it with others. Jason is the world’s leading property management growth hacker, and enjoys helping property management business owners grow their businesses. He’s the host of the "Door Grow Show", founder of the Door Grow Club, a free Facebook group for property management entrepreneurs, and the creator of The Seed Program: The Ultimate...


161: How to Lose Money by Trusting a Seller on Their Word with Zach Beach

Zach Beach works with, located in Newport, Rhode Island. He works alongside his wife, Kayla, brother-in-law, Nick, father-in-law, Chris, and a great support team. He’s a successful real estate investor, completing over 100 deals in under 3 years and continues to buy and sell property without using his own cash, credit or investor’s money. Zach is co-authoring their second book, The New Rules of Real Estate Investing. At age 25, Zach decided to jump into the family...


160: How to Lose Money by Losing All Your Customers with Ian Ippolito

Ian Ippolito is a serial entrepreneur and the creator of the investment analysis website called The site has over 12,000 visitors per month and has been featured in USA Today, Bloomberg News,, Curbed and more. Ippolito is also the founder of a private investor club for alternative investing, with over 1,300 members and over 1.35 billion in investable assets. In 2001, Ippolito created one of the first remote work websites from an extra bedroom...


159: How to Lose Money by Doing Something Crazy with Brendon Lundberg

With a vision to build the safest, most consistently effective and appealing solution to the epidemic of chronic pain, Brendon Lundberg co-founded Radiant Pain Relief Centers. He combines his mission to change the way chronic pain is treated with deep experience and healthcare management, marketing, business development and sales. Prior to opening the first center in 2014, Brendon played key operational and business development roles for two Portland-area Business Journal and Inc. Magazine...


158: How to Lose Money by Saving a Couple Hundred Bucks with Terry White

Terry White is a long-time business owner and investor. He’s a graduate of the University of New Mexico and began his career as the controller for the largest title company in New Mexico. In 1987, he started his first business, First Financial Escrow, Inc. Over the years, his business grew until in 1997 he purchased the real estate contract division from the largest bank in New Mexico. October 2017 marked First Financial’s 30th year in business. In 2004, Terry started Sunwest Trust, Inc. to...


157: How to Lose Money by Buying at the Top of the Market with Brian Burke

Brian Burke is president and CEO of Praxis Capital, Inc., a vertically integrated real estate private equity investment firm, which he founded in 2001. Brian is also a member of the Praxis Investment Committee. Praxis operates on multiple platforms, currently managing active syndications for the acquisition of single, multifamily and opportunistic residential assets in the U.S. growth markets. As a recognized real estate expert, Brian has been a frequent speaker at real estate forums and...


156: How to Lose Money by Accidentally Flipping a House with Lee Kearney

Lee Kearney is one of the nation’s most active and successful single-family real estate investors, having flipped over 7,000 houses in the last decade, totaling over $500 million in property under his SPIN Real Estate company. Lee is known as the leading expert in understanding and leveraging real estate market cycles. He has been on the front lines of flipping homes, and his passion and expertise come into play as he inspires and educates real estate investors at all levels through his...


155: How to Lose Money by Chasing the Wrong Dream with Ellie Perlman

Ellie Perlman is a real estate investor who owns 2,000 units across the U.S., worth over $250 million. Ellie is the founder and CEO of Blue Lake Capital, a real estate investing firm specializing in multifamily investments. At Blue Lake Capital, Ellie helps investors grow their wealth and get double-digit returns by investing alongside her in large multifamily deals that they wouldn’t otherwise have access to. Prior to founding Blue Lake Capital, Ellie was a commercial real estate lawyer and...


154: How to Lose Money by Signing Bad Contracts with AJ Osborne

AJ Osborne has been in real estate since the early 2000s. He created Bitterroot Holdings, a self-storage company that has a $100 million asset holding portfolio. He got his start in insurance running one of the largest brokerage firms in the northwest.


153: How to Lose Money by Relying on Your Insurance to Protect You with Scott Smith

Scott Royal Smith is a real estate investor and asset protection attorney in Austin, Texas. He graduated from Albany Law School and began his career in high-stakes corporate litigation. Scott learned the key secret he now uses to defeat lawsuits, that they are a business. Through his defense work, he targets defeating lawsuits before they are even filed by making sure the business part of a lawsuit no longer makes financial sense for a plaintiff to proceed. Scott founded Royal Legal...


152: How to Lose Money by Investing in Single Family Homes with Joe Fairless

Joe Fairless is a full-time real estate investor that started buying multi-family properties in 2013 and now controls over $400 million of real estate, with a portfolio of over 4200 units. He’s personally raised over $100 million from private investors for real estate investments. Prior to that, he was the youngest VP at an award-winning advertising agency in New York City. He’s the host of the world’s longest running daily real estate iTunes podcast, “Best Real Estate Investing Advice...


151: How to Lose Money by Taking an Equity Stake with Kevin Monaghan

Kevin Monaghan’s wide-ranging experiences, from production assistant on NBC’s “The Office” and “Parks & Recreation” to building one of the largest Financial Expat Consulting firms in China, prepared him for the work he does today, which is aligning the interests of business owners, partners and investors to structure compensation models, maximizing clarity and rewards. Currently based in Charlotte, North Carolina, Kevin founded the Intuitive Compensation Group, where he uses his skills...


150: How to Lose Money by Investing in Toilets, Tenants and Trash with Scott Meyers

Scott Meyers is the nation’s leading expert in self-storage. After becoming a penniless landlord in the single-family rental and apartment business, he began investing in self-storage. He saw the light and quickly sold all of his single-family rentals and apartments to create a small empire of self-storage facilities nationwide. His company’s focus on syndicating self-storage deals and helping others to launch their own self-storage business to enjoy a lifestyle free from toilets, tenants...