You're ready to jump into the waters of entrepreneurship...or maybe you aren't, but you ARE curious. What questions should you ask yourself BEFORE you lay down your hard earned money to invest in inventory, systems, and people? Happy Friday! Today we ditch our usual Friday format and instead offer up a super special game show edition of SB! On today's show we'll quiz Chief Side Hustler and the host of the Side Hustle Show, Nick Loper, plus regular contributors Paula Pant (Afford Anything) and OG on THE questions an entrepreneur should ask before creating a start-up. Think you have what it takes to create your own business? Play along with our cast and find out!
After we have our fun with the game show, Joe will ring up Justin Pogue, the author behind Rental Secrets. We'll talk to Justin on how to get more value out of your dollar by using insider knowledge to lower your rent and earn yourself more leverage.
Plus, with Nic Loper on the roundtable, we'll answer a specially-themed entrepreneurial question from Reddit. The user writes that they'll very possibly be fired from their day job soon, but that they're starting up their own business and things are beginning to go well. What should they do?
A big thanks to Quickbooks for supporting Stacking Benjamins. You can save an average of $600 annually by paying your employees with Intuit QuickBooks Payroll. Check it out today at Intuit.me/sb.
Another big thanks to Native for supporting our podcast as well. Get 20% off your first purchase by visiting nativedeodorant.com and entering promo code SB during checkout.
What Hidden Fees and Costs are Sneaking Money From Your Wallet? (SB1583)
Quit Saving Sooner, Live Freer (SB1582)
From Legal Briefs to Bistro Feasts: Erin Wade's Story (SB1581)
It's Easier Than Ever To $%*! Up Your Money (SB1780)
Inspiring Financial Independence Stories and Lessons from Missteps (LIVE from CampFI Midwest 2025) SB1579
Lobsters, Lincoln, and Financial Lessons (SB1578)
How to Lose Money in the Markets: The Game Show Edition (SB1577)
Pension Perils: Lessons from the Dallas Fund Fiasco (SB1576)
Mastering Retirement Planning (plus Real Estate Commission Negotiation) SB1575
Turning Goals Into Adventures: Transforming Your Financial Journey (SB1574)
Three Dads Share Tips and Stories on Teaching Good Money Habits (Jon Acuff & John Lanza) SB1573
Touchdown Tips to Boost Your Financial Game (featuring ex- NFL star Brandon Copeland) SB1572
How Much Can a Great Coach Truly Help? A Roundtable Discussion (SB1571) Greatest Hits!
Mark Cuban Shares Frugal Tips -- Should We Care? (SB1570) Greatest Hits and Earn & Invest Replay
Is a Latte Going to Ruin Your Retirement? (SB1569) Greatest Hits!
Stop Delegating Your Financial Decisions! (Bola Sokunbi AND Susan Tompor) SB1568 (Greatest Hits!)
Top 5 Metrics You Need To Know To Build a Better Financial Plan (SB1567) Greatest Hits!
Extreme Rentals: Should You Rent Everything? (SB1566)
Stop Losing Money on Your Company Benefits (SB1565)
Feeling Cynical? That May Be Costly For Your Wallet and Career (SB1564)
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