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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118: How to Lose Money by Not Being in Touch with the Market with Sean Morrissey

Sean entered the Real Estate forum as an Investor in 2003 and now leads one of the premier residential property management firms in the Fox Valley area. Managing over 180 residential properties and hosting a team of Realtors assist homeowners throughout the western suburbs with the purchase or sale of their home, Sean's expertise and dynamic background can assist buyers and sellers in the Chicago real estate market. He hosts a podcast called Landlording for Life. Sean lives in Aurora with...


117: How to Lose Money by Picking the WORST Time to Buy with Mark Hentemann

Mark is a writer/producer and also an avid real estate investor living in Los Angeles. Originally from Cleveland, Ohio, Mark started out drawing caricatures at Sea World (where he was struck by lightning) before landing a job as a greeting card writer/illustrator in the Alternative Humor department at American Greetings. His cards got him hired to write for The Late Show with David Letterman in NY until 1999, when he moved to Los Angeles to join a new show called Family Guy. Mark’s been a...


116: How to Lose Money by Being Blinded by Success with Isaac Tolpin

Isaac Tolpin is one of the Founders of, the #1 Micro-Learning platform for influencers and companies. He’s a tech entrepreneur and futurist at heart, enabling brands to authentically connect and inform at scale with over $105 million in combined revenues from the companies he’s helped build. His success comes from understanding the relationships between human behavior, business and technology. This expertise has helped celebrity influencers and companies to transform their...


115: How to Lose Money by Purchasing a Home in a Real Estate Bubble with Cedric Van Duyn

This episode is for anyone wanting to achieve financial independence before retirement age. Learn about the signs of a housing bubble and how you can avoid the mistakes that Cedric made. Luckily failure is not final as long as you keep moving forward! Cedric is a native South African who married an American girl and is now a pastor in the Pacific Northwest. His journey with Real Estate has progressed from mistakes made in ignorance to an intentional strategy towards financial increase and...


114: How to Lose Money by Speculating in Commodities with David Stein

For reference, we talked about the difference between investing and speculating back in Episode 21. It was great having David on the show and we know you will enjoy hearing his wisdom! David Stein produces and hosts the weekly podcast Money For the Rest of Us where he weaves together stories, examples, academic research and media findings on topics related to money, investing and the economy. The podcast launched in May 2014 and has over 185 episodes and more than six million...


113: How to Lose Money by Investing in Volatile Assets with Hunter Thompson

Hunter Thompson is a full-time real estate investor and founder of Cash Flow Connections. Since starting CFC, Hunter has helped investors allocate capital to over 100 properties which have a combined asset value of more than $350,000,000. His experience includes investments in self-storage facilities, residential mortgage notes, mobile home parks, single-family acquisitions, hard money loans, office buildings, and multi- family real estate syndications. In connection with these...


112: How to Lose Money by Blindly Following Your Industry's Trends with Geoff Woods

Geoff Woods is the Vice President of The ONE Thing. After hearing the Jim Rohn quote that “you are the average of the 5 people you spend the most time with” Geoff set out on a mission to surround himself with high level CEOs and successful entrepreneurs. Fast forward just 10 months, Geoff went from employee to entrepreneur, launching a company with the co-authors of the best selling book The ONE Thing. Geoff has been featured in and is on a mission to teaching people how...


111: How to Lose Money by Selling a Product That Nobody Wants with Michael Zipursky

You NEED to find the right product (or service) to sell. In this episode, Michael shares his tips and lessons about finding the right thing to sell. Michael Zipursky is an author, lead-generation and marketing consultant, and entrepreneur. His work has appeared in the Financial Times, FOX Business, Maclean's, HR Executive, MarketingMag, Management Consulting Journal, and in several other media and publications. Michael runs Consulting Success, the leading consulting resource for people...


110: How to Lose Money by Not Taking Responsibility with Trever Crane

Not taking responsibility for your actions and words can lead to a world of pain. In this episode, Trever tells his story and aims to help people avoid some of the mistakes he made. Trevor Crane is a 11-time #1 bestselling author and the founder of Epic Author Publishing. Trevor helps business owners, speakers, coaches and consultants become IRRESISTIBLE to their ideal target clients, and consistently grow their LEADS, SALES and REVENUE. Host of the Greatness Quest podcast, Trevor can...


109: How to Lose Money by Failing to Value Your Time with Doug McCormick

What is your time worth? Doug McCormick offers actionable steps to avoid wasting time and how to value life's most precious asset: your time. Doug McCormick has a lifetime of experiences that provide the foundation for the framework, principles and tools in Family Inc. As a professional investor, he has spent two decades managing money for institutional clients such as insurance companies, pension funds, entrepreneurs and high net worth families. As Managing Partner at HCI Equity, Doug...


108: How to Lose Money by Not Raising Capital with Anika Janelle Pettiford

Do you need to raise money for your business to grow? Not always. But in same cases, as Anika describes, it is essential. Anika Janelle Pettiford is the founder of a group of companies under the Elani brand; including a creative agency, a publishing house and a digital retail empire that spans an array of categories. She also co-founded Iolani Research Lab, an engineering consulting firm with her husband Dr. Pettiford. Her illustrious career began in the tech field where she worked for...


107: How to Lose Money by Investing in Real Estate Out of Town with Todd Tresidder

If you are interested in real estate investing, early retirement, and personal finance Todd shares practical tips to help you succeed in areas that he experienced failure. Todd Tresidder graduated from the University of California at Davis with a B.A. in economics and a passion for creating successful businesses. A serial entrepreneur since childhood, Todd went on to build his own wealth as a hedge fund investment manager before “retiring” at 35. He grew his net worth from less than zero...


106: How to Lose Money by Jumping in Without a Plan with Jason Wright

We have all heard the saying "start with the end in mind" but few of us actually live that out. Jason shares practical insight about how to strategize and win in your business! Jason is the founder of the Intentionally Inspirational brand which began as a podcast that was created to motivate and inspire entrepreneurs. Since its inception, Intentionally Inspirational has evolved to include a weekly blog, published resources and a comprehensive offering of digital marketing services and...


105: How to Lose Money by Making Hasty Decisions with Kimberly Nguyen

Are you the kind of person who is prone to act first and ask questions later? This episode is for you! Kimberly Nguyen is a Co-Founder and Partner with DreamVest Capital Management and is primarily focused on overseeing operations, sales, and investor relations. This same belief is what inspired her to start her own real estate business over 12 years ago, and ignited her passion to create passive income in real estate for both herself and her clients. Despite her success in real estate...


104: How to Lose Money by Being Stubbornly Independent and Blindly Optimistic with Dr. Phil Carson

Dr. Phillip Carson is a Registered Pharmacist, Doctor of Pharmacy with license in MS and TN, and graduated from the University of MS School of Pharmacy. Phillip Carson, the Co-founder of the Life Transformation Medical Center and President of Carson Natural Health, LLC is a Pharmacist who thinks outside the box of traditional medicine. He believes in helping people find natural alternatives and integrative medicine solutions to their health problems. He is committed to leading people to...


103: How to Lose Money by Investing at the Wrong Time with Warren Hogarth

Timing is everything, or so they say. Warren has decades of experience in investing and brings invaluable knowledge on this episode of How to Lose Money. Warren Hogarth is the Co-Founder and CEO of Empower, a new consumer finance app that was one of Time’s best new apps of 2017. The Empower app helps entrepreneurs and side hustlers stay on top of their finances, get personal recommendations and save hundreds to thousands of dollars per year. Prior to launching Empower, Warren spent eight...


102: How to Lose Money by Not Charging Enough with Joe Kashurba

Not charging enough for your goods or services is a trap many entrepreneurs fall into. In this episode, hear how to avoid this pitfall and get insight on hitting the right price point. Joe Kashurba grew the freelance web design business that he started in high school into a digital agency with a virtual team and clients around the world. He went from building $300 websites to building $30,000 websites and managing 6-figure digital advertising budgets for some of the largest manufacturing...


101: How to Lose Money by Being the Smartest Person in the Room with Mark Podolsky

You NEVER want to be the smartest person in the room. Learn why. Mark J. Podolsky (AKA The Land Geek) is widely considered the Country’s most trusted and foremost authority on buying and selling raw, undeveloped land within the United States. He has been actively investing in Real Estate and Raw Land since 2001 and has completed over 5,000 unique transactions. Mark has achieved this level of success largely due to his core business philosophy – “Happy Customers Guaranteed.” Mark is the...


100: How to Lose Money by Not Reading a Contract with Brandon Hall

In this episode, Paul and Josh reminisce about how this podcast got started as well as the overarching themes that emerged from the past 100 episodes. Later in the episode, Brandon Hall tells a great story with actionable advice for anyone who regularly signs contracts. Brandon Hall is the founder and CEO of The Real Estate CPA, a CPA firm that works exclusively with individuals and businesses in the real estate industry. He previously worked for two Big 4 Accounting Firms and he has...


99: How to Lose Money by Choosing the Wrong Service Provider with Jason Payne

In this episode, Jason shares tips for choosing the right title company, but these tips can apply to anyone looking for a service provider in any business. Jason Payne is a hard money lender in Texas and works for ISB Capital. ISB Capital has been in business for 15 years and has lent over 400 million dollars to real estate investors doing flips and for new construction. ISB Capital is one of Texas’ leading sources of financing for new construction and real estate investor loans. ISB...


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