The Stacking Benjamins Show

John Warrillow has built and sold many businesses, and has created a business value builder system used by thousands of businesses worldwide. With many, many years of experience under his belt, John knows a thing or two on how to bring value to a business. Today, he brings that wealth of knowledge with him to help make better financial sense for your family. Tune in for an insightful discussion featuring case studies, interesting stories, and maybe a new way of looking at your family's financial picture.Hot take incoming: every time you make a bad financial decision and lose big (let's say shorting GameStop to the tune of $200,000), maybe you should blame someone else and sue them to recoup your losses! Sound crazy to you? Tell that to Christian Iovin, the man suing leading Reddit investor "DeepF$%kingValue" over his part in the short squeeze. During our headlines, Joe and OG give a thorough deconstruction detailing how the "get-rich-quick" mindset can lead a person down some strange paths - including thinking that a social media figure is responsible for your investing choices. While we aren't without sympathy, we break down how Iovin willingly made his choice on what he thought was a great deal at the time, and offer up some sound advice to not get yourself caught between a rock and hard place - short squeeze or otherwise).We'll keep today's theme going with our second set of headlines. Bill Gates is now officially "meh" on Bitcoin (it's an improvement!), and financial advisors are ready to back the truck up to crypto.Now hold on a second if you think you know where this is going. We're not here to preach #teamcrypto or denounce the movement either way. What we are saying, like in our interview with John Warrillow, is that you need systems. We've said the same thing about Tesla and Apple, and the rules don't change for Bitcoin. The biggest danger to your portfolio isn't a Redditor or Capitol Hill, it's you. The best thing you can do for your bottom line is taking yourself OUT of the equation.Enough of that, moving on. Finishing out today's show is a Haven Life line question from Zac. He asks... (checking notes...)... is putting $20 a week into a somewhat random stock that has shown positive growth a good idea? Truth be told, we could have went a lot of different ways with this one. I'm proud to say the guys put some thought into this one, and not only give Zac an answer, but dive into some explanations on different stock analysis theories.Of course, Doug always gets some airtime for his trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's the next step after you finally "make it"? While it's easy to scoff at the problems of people who are financially set, it's not uncommon to lose a sense of purpose once you jump out of the rat race. Bigger questions start to come up: what's your real purpose in life? What type of legacy are you leaving behind? How will your personal relationships be impacted by your new-found financial status? What type of impact do you want to make on the world? Shining a new light on these ideas that often don't receive enough attention is Jennifer Risher, author of We Need To Talk: A Memoir About Wealth. We'll talk to her today!Taxes, taxes, taxes.It's that time of year again. Joining us to talk all things taxes during our headlines segment, we welcome tax software expert extraordinaire, Hannah Rounds from The College Investor. Whether you're a landlord, charitable giver, paying off college debt, contributing to an HSA, or anything in between, Hannah has great advice ensuring you won't be leaving any cash on the table.Plus, Fidelity recently held an AMA (ask me anything) on Reddit. The thread gathered A LOT of attention, but not for the reasons you'd think: everyone had Robinhood on their mind. While Reddit users did comment on the GME/Robinhood debacle, there was a bigger question: why in the world does Robinhood have such an incredible user interface, while many of the other big-name brokerages and bank apps seem to be stuck in the first episode of Wandavison?We'll finish out the show with a Haven Life line question from one listener who has finally come to their senses with Robinhood. Listener Taylor has invested with the company for years and he's ready to jump ship. The big question? How can he change move his investments to another brokerage without taking a big capital gains hit? We'll give him many options so he (and you!) can move on to greener pastures.Naturally, we'll also give Doug his airtime halfway through the show. FAANG stocks used to be all the rage, but some investing pros are looking to the future and is giving one company the boot. Find out which one during Doug's trivia.Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling stuck? Maybe it's time to move. Of course, it's a lot easier to write about moving than actually planning and doing it. And while a move may pay off in the long run, there could be a hit initially to your finances. With that in mind, today we ask our round table contributors: what exactly would encourage you to move? Better location? Pay? Maybe you want to escape the harsh Detroit winters? (I'll let you guess who had that complaint). It's a fun conversation that covers a breadth of topics in true Stacking Benjamins fashion. Helping us out today are our round table regulars: Paula Pant from the Afford Anything podcast, Len Penzo from the LenPenzo.com blog, and our very own OG.Halfway through the show, we'll give our contributors a break while Joe talks everything alternative investments with Michael Weisz, co-founder of alternative investments company Yieldstreet. During their interview, Michael covers everything from the company origin stories - a shocking reality check that a large percentage of everyday consumers were locked out of the alternative investments sector - to helping investors by cutting down average IRA rollover times from forty days to six. If you've ever wondered about other investment choices outside of stocks, bonds and funds, this is one interview for you.We'll end today's show with our MagnifyMoney segment. Caller Kevin tells us that his father passed away last year. While he isn't attached to the credit card debt his father left behind, he's heard the horror stories of banks hounding family members after a loved one's death. Kevin asks: what's the best strategy for dealing with the looming creditors? We'll give Kevin some heartfelt advice that we hope can make this time a little easier.Of course, we'll give Doug his airtime halfway through the show, and he's keeping things Texarkana Classy with today's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you have money conversations with the people in your life without making things awkward? From asking the boss for a raise to having a tricky money chat you'd rather not have with a family member, and even to opening honest lines of communication with your partner - money can be a scary topic to broach. We bring good news: it doesn't have to be. Erin Lowry, the mind behind the Broke Millennial series, joins us today to share how you can move beyond the "pit in your stomach" feeling when it comes to money conversations, and the answer (really) is easier than you'd think.Plus, during our headlines... let's just say the local Texarkana Chamber of Commerce isn't too happy with how we've been portraying the small quaint town of Texarkana. Chamber of Commerce President, Bubba "Tex" Mext had a few words he wanted to share with us, and - lucky for you - we caught it all on tape, and we're sharing it here today.Of course, we won't leave you high and dry either. When we find some clean airtime, we'll also discuss a piece about the growing popularity of HSAs. While the book is still out on investor sentiment towards a dual HSA/401k investment approach, it's not the worst idea to consider for your larger financial portfolio. We'll explain why during our headlines.During our Haven Life Line, we'll answer a call from Maz, who has more questions about the GameStop situation. What are the big lessons to take away here? What should investors have learned? How can people do better in the future?Naturally, Doug can't let Tex Mext make so much commotion without having a few words on the matter himself. Better brush up in your Lone Star knowledge, because Doug has Texas on his mind today during his trivia.Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think you can't network like a pro because you're an introvert? Better put your party hat on and take a shot of liquid courage, because our guest today is coming in with strategies and techniques that'll turn anyone into a lean, green, networking machine. (Without resorting to sending out hundreds of spam emails). Our guest, Matthew Pollard, has helped multiple businesses become million-dollar ideas, and he assures us it has a lot less to do with having the skills of a smooth talker, and a whole lot more with honest connection and preparation.Having trouble with the law? While the long arm of the government may be able to seize your bitcoins, today's piece shows that by forgetting a key piece of information, you don't have to worry about your bitcoins ever really going goodbye - but good luck cashing anything in for your retirement. Plus, we'll cover why everyone's favorite mortgage strategy, velocity banking, is an off-the-rails fun way of paying down your debt... until it all comes crashing down around you.Plus, during our Haven Life line, Justin tells us he's interested in buying stocks for his daughter. Her favorite game, Roblox, is about to go public, but the company is doing a direct listing. Justin asks: Are direct listings as bad as IPOs for everyday investors? Is there anything he should know about before getting involved? We'll give Justin the rundown, and even throw in a few of our favorite apps to get kids started on investing.As always, we'll save some time for Doug's network-based trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Love is in the air, and today, no matter your relationship status, you're gonna LOVE our discussion on your relationship with money. How is it? Is it healthy? Growing? Worrying? We'll discuss all of the emotions around money on today's show, featuring a cast of financial media peeps including Paul Ollinger from the Crazy Money podcast; Paula Pant from the Afford Anything podcast; and our very own OG.Plus, just in time for Valentine's Day, there's big news from the financial app for couples called Zeta. The founder of Zeta, Aditi Shekar is back, to share all of the details. If you have a relationship with someone AND you're trying to mix money in any way, you'll want to hear their news.Of course we'll still all have opinions for a lucky listener on today's MagnifyMoney.com call AND we'll battle it out over Doug's Valentine's Day themed trivia question. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Well, we went and added a comma. You weren't counting, but mom was. Today we'll share the money lessons we've learned over our first 1,000 (wow, have we really made that many?) episodes. Plus, we'll hear from many of our friends you'll recognize from the financial community. We'll share a monster list of our favorite books and resources, but all of the things that we've learned on our journey over the past (near) decade.During our headlines, we'll double up on the experts. First, we'll talk to Dirk Izzo, president and GM of Hospitality at NCR, who'll share how restaurants embraced innovation and kept revenue flowing in the face of unprecedented challenges. In our second piece, we'll invite the man who literally wrote the book on silver investing to explain the craze in the silver markets hitting the news lately. What was happening while we were all watching Gamestop? It turns out, a TON. David Morgan will share his best tips on today's show.As always, we'll save some time for Doug's trivia.Finally, thank you Stackers for making a thousand episodes of this little podcast a reality. We couldn't have done it without you. Enjoy the show.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

It seems absurd now, but Netflix co-founder Marc Randolph was told early on that his company name would never work. Today, he's going to give us some of the same advice he's giving on his new podcast, "That Will Never Work." We'll discuss fighting fear, hiring the right team, having conviction in your ideas, and more. And don't worry if you aren't interested in becoming an entrepreneur. We also asked Marc how to interview better (he's interviewed thousands of people) AND how to ask your boss for a raise. In fact, you'll be surprised what he has to say about raises.Wondering what's going on in the world of fintech? During our headlines, we'll share the newest developments in tech that helps you manage money better. From advancements in technology making your information more secure against hackers to new-new digital banks promising more consumer-friendly resources and more, there's a ton of interesting developments on the horizon. We'll cover many of them. Plus, we'll tackle a headline about Jeff Bezos stepping down from Amazon. Do you think he finally reached his magic number and has enough to retire? Maybe he gave of the lattes and buckled down? Probably not, but that won't stop us from talking about setting goals, retirement, and more.We'll finish today's show with a question we often get about 401k plans. After you leave a company, should you move your funds? Josh left the basement a voicemail explaining that he likes keeping his investments in one place so it's simple to stay focused on the big picture. However, Josh won't be able to contribute to the Thrift Savings Plan after he retires from the military. He asks: is there a benefit to keeping his money in the account? Would he be missing out on anything if he rolls his TSP over to a Roth IRA?As always, we'll save some time for Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you get to the top of your game? How far would you go to keep your business and personal social groups aligned with your goals? We'll quiz our roundtable, plus get their thoughts on the number one goal they're trying to attain currently. Our contributors this week are Sandy Smith from YesIAmCheap.com; Paula Pant from the Afford Anything podcast; and Len Penzo from the LenPenzo.com blog.After we finish talking about goals and dreams with our roundtable we'll pivot to our interview with Brian Hamilton, the co-founder and CEO of the new digital bank One. There's been a lot of great improvements in the digital banking industry, but Brian found a problem: it was hard to find a good bank that offered all the features someone would want. His solution? Make one. During our fintech segment, we'll dive into the making of One with Brian and talk about good business values, vision, and the digital banking landscape.During today's MagnifyMoney call we'll tackle a question on credit card rewards. Alan tells us he and his wife have been playing the rewards game and got up to $10,000 in 2020. He says it seems like a great side hustle and ask for our thoughts.As always, we'll give Doug some airtime halfway through the show to have this week's trivia game show. If you happen to be knowledgeable on the annual revenues of Wisconsin-based shower head companies, this one is for you.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

We've told plenty of incredible underdog financial stories on the podcast, but none like the one's you'll hear today. More than recovering from 6-figure debt or learning how to balance their budget, today we're excited to bring you the stories of the first black Americans, some of whom survived slavery, but who all went on to become millionaires. Shomari Wills, author of Black Fortunes, joins us today to bring incredible stories of fortitude, challenges and surpassing hardships.We're sticking with the financial "comeback" theme during our headlines. Think you should throw in the towel on the whole financial independence thing because you've made a few mistakes? While you may not have the star power to pay off a $9 million tax evasion bill, like today's headline focus, Mike "The Situation" Sorrentino, your path to independence isn't over because you've wracked up some debt or made some bad decisions. Plus, a big life insurance company just was sold to another. If you're a client, what happens to your policy? We'll describe how it all works on today's show.Of course we'll also throw out the Haven Life Line to a lucky listener AND save time for some of Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices