336. The UPS Store Small Biz Challenge: The Trading Secrets Behind Two Breakout Entrepreneurs

What does it take to turn a simple idea into a real business? On this special episode of Trading Secrets, Jason Tartick sits down with two entrepreneurs who competed in The UPS Store’s 2026 Small Biz Challenge after nearly 6,000 businesses applied—and both made it to the final three. The Laundry Basket, shares how it turned a $20 first customer into a growing, multi-city laundry and linen management business by focusing on convenience, recurring revenue, partnerships, B2B opportunities, and knowing her numbers. High Strung Raquets, explains how it identified a gap in the tennis and pickleball market, built a premium product around style and performance, and learned how to sell through wholesale, storytelling, and strategic partnerships. Jason and the founders break down the importance of differentiation, discipline, storytelling, social media, customer feedback, cash flow, scaling without becoming the bottleneck, and knowing when to work smarter instead of harder. Plus, both entrepreneurs reveal the trading secrets they learned from building their businesses—and why sometimes the best time to start is before you're ready. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Vivian Tu, aka Your Rich BFF, is back on Trading Secrets nearly three years after her first appearance—and a lot has changed. With over 10 million followers and $8.2M in annual earnings, Vivian breaks down exactly where the money comes from, including brand deals, speaking, books, and podcasting, plus the team and expenses behind that massive top-line number. She reveals why she invested over $1M of her own money into building Ask Dolly, her new financial wellness app, and why she chose to self-fund instead of raising outside capital. Vivian also shares how she’s grown her audience without spending a dollar on paid ads, why she still posts every day, and how the creator economy is evolving beyond traditional influencers. Plus, Vivian gets into the current financial uncertainty, emergency funds, high-interest debt, wedding budgeting after her Lake Como wedding went 3X over budget, and the $10K wedding expense she regrets. She also opens up about speaking on financial policy, whether she’d ever consider politics, and why her newest Trading Secret is knowing when it’s worth fighting for what you want. Host: Jason Tartick Audio: John Gurney Video: Marc Colcer Guest: Vivian Tu Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick and the Curious Canadian are back for another 30 Minute Thursday, breaking down the biggest stories impacting your money, career, and life. They recap Jason’s conversation with Andrew Spencer and Alex Bordyukov, including the future of Bachelor Nation, reality TV’s changing landscape, relationships, prenups, and how their careers and finances have evolved. Then, they dive into the economy through an unlikely lens: fast food. With Wendy’s franchisees facing bankruptcy, McDonald’s stock down and inflation continuing to pressure consumers, Jason and David break down what restaurant prices can tell us about the broader economy. Plus, Jason gives a personal update on his upcoming wedding plans, reveals why Cabo is currently the frontrunner, talks about moving out of his New York apartment, and reflects on entering a new chapter of life. They also discuss rising gas prices, mortgage rates, home prices, wage growth, and why making your money work harder matters. And David shares a real-life Trading Secret he put into action—moving his savings from a 1.75% account to one paying 4%. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Bachelor Nation’s Andrew Spencer and Alexe Godin join Jason to break down the money, career pivots, and relationship realities that came after Bachelor in Paradise. Andrew reveals how his income has grown from roughly $75K his first year after the show to $200K the following year—and why 2026 could be another major jump—while Alexe opens up about nearly $100K CAD in student debt, leaving her career as a speech-language pathologist after realizing content could pay roughly 3X more, and using her Paradise winnings to help wipe out debt and invest for retirement. The couple also gets candid about turning down the money for love on Paradise, why Andrew secretly strategized once a cash prize entered the game, their very different relationships with money, keeping their businesses and finances separate for now, and how their childhoods shaped what financial security and family mean to each of them. Plus, Alexe talks about pursuing acting, Andrew shares how he’s building a brand beyond Bachelor Nation, and they open up about navigating the pressure to get engaged, merge lives, and figure out what comes next. Host: Jason Tartick
Audio: John Gurney
Video: Marc Colcer
Guests: Andrew Spencer & Alexe Godin Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick and the Curious Canadian are back for another 30 Minute Thursday with a little bit of everything. Jason breaks down the latest Federal Reserve rate hike and what it means for your credit card debt, savings, and investments, while David asks how to put $10,000 to work, whether a high-yield savings account or CD makes sense, and how dollar-cost averaging can help you get invested over time. The guys also debate whether David should set up an LLC for his hockey consulting side hustle, what business expenses may qualify as deductions, and why keeping receipts and working with a tax professional matters. Then it’s all pop culture. Jason recaps a whirlwind week in New York City, including the US Open, celebrity events, and his upcoming night with Brad Pitt, while the guys break down the return of Chris Harrison to reality TV, the new show The Vow, and their thoughts on the latest season of Dancing With the Stars. Plus, a Starbucks rant, the rise of AI and robots, Jason’s week in NYC, and the real reason the Jesse James Decker episode was pulled and replaced with the Val episode. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Description:With a new season of Dancing With the Stars just around the corner, we’re flashing back and revisiting one of our favorite conversations with DWTS legend Val Chmerkovskiy. Originally recorded in 2023, Val opens up about his unconventional path from competitive ballroom dancing to becoming one of the biggest names on television, including why he initially resisted joining Dancing With the Stars, what finally changed his mind, and how his career evolved once he made the leap. Val also gets candid about the business of being a professional dancer, the financial realities of competitive dance, negotiating his value, building multiple streams of income, and why he would sometimes choose equity in a business over getting paid upfront. Plus, he shares the mindset that helped him navigate difficult seasons, career setbacks and the uncertainty of being dealt a bad hand: “delusional optimism.” From building Dance With Me Studios to turning his DWTS platform into a larger business ecosystem, this is a conversation about knowing your value, betting on yourself, and turning a passion into a career. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jessie James Decker has built a career by refusing to stay in one lane. From country music and reality TV to fashion, fitness, publishing, and entrepreneurship, Jessie has turned her creativity into a growing business empire—and she joins Trading Secrets to break down how she did it. Jessie opens up about growing up with very little, the childhood experiences that still drive her to prove herself, and the financial mistakes she made early in her career. She shares the money lessons she learned from her husband, Eric Decker, why surrounding yourself with people who are smarter than you can be a game changer, and how her biggest weaknesses have become some of her greatest strengths. She also gets candid about building Kitnish into a $60 million business, recognizing when she needed to step away from the CEO role, and why giving up operational control was one of the hardest—and smartest—business decisions she made. Plus, Jessie reveals how she built a fitness community of nearly 40,000 subscribers, why authentic content is outperforming highly produced social media, what she thinks is missing from today's music industry, her experience on Dancing With the Stars, and the money and relationship rules that have helped her and Eric navigate their careers together. And she leaves us with her ultimate Trading Secret: “It’s never no.” Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick and the Curious Canadian are back for another 30-Minute Thursday covering everything from Jared Freid’s relentless approach to success to Apple’s brand-new $2,000 foldable iPhone. The guys break down the biggest business takeaways from Jared’s return to Trading Secrets, including why asking for what you want, being scrappy, and putting yourself out there can create opportunities. They also debate whether the new iPhone is actually worth the price, talk podcast negotiations, the rise of athletes in pop culture, the US Open, football season, and the latest sports headlines. Then, for the first time ever, a Trading Secrets listener joins the show. Taylor Fraser shares her journey from accounting to teaching, how she turned her side hustles into a growing business, and how she and her husband launched Bluegrass Flow, a cold-pressed juice company now sold in 60+ retail locations. Taylor also opens up about teacher compensation, retirement, AI in education, entrepreneurship, using grants to fund a growing business, and the importance of building a career around something you genuinely love. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, Jason is joined by stand-up comedian, podcaster, and now first-time author Jared Freid for a conversation about the business behind comedy, betting on yourself, and how money, confidence, and relationships are more connected than we think. Three years after his first appearance on Trading Secrets, Jared returns with his second Netflix special, The Family Plan, and breaks down exactly what it took to get there. After spending roughly $80,000 producing his first special, Jared reveals why he invested around $100,000 of his own money into the second, how the licensing economics work, why he partnered with Betches for marketing power, and why that partnership means splitting the licensing fee 50/50. He also shares why landing in Netflix’s Top 10 in the U.S. and Canada for nearly a week still wasn’t enough to guarantee Netflix would finance his next special. Jared also opens up about the economics of his growing comedy career, revealing that touring and the U Up? podcast are currently his two biggest financial drivers. He breaks down the ownership structures behind U Up? and JTrain, why subscriptions have become increasingly important to podcasting, and why paid social partnerships remain more of a bonus than a core piece of his business. Beyond comedy, Jared gets candid about writing his first book, Walking Red Flag, including spending two years on the project, realizing after his first page that he needed a ghostwriter, and paying that expense out of his book advance. He also shares how stepping away from alcohol, his experience with GLP-1s, and rebuilding his relationship with his girlfriend changed his confidence and outlook on life. From investing six figures into your own career to prenups, joint finances, ghosting, dating economics, protecting what you’ve built, and why Jared says he’s never regretted taking a risk—this episode breaks down what it really looks like to build a career without waiting for someone else to give you your big break. Host: Jason Tartick
Audio: John Gurney
Video: Marc Colcer
Guest: Jared Freid Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick and the Curious Canadian, David, are back together for another chaotic 30-Minute Thursday—and they have a lot to unpack. From Jason’s trip to the U.S. Open and the eye-popping $108 million prize pool, to the $23 Honey Deuce and the bizarre world of Burning Man, the guys cover it all. They also dive deep into AI, the fear of giving bots access to our personal lives, the future of work and parenting, and how social media algorithms are increasingly shaping—and sometimes hijacking—our brains. Plus, they break down the latest Dancing with the Stars cast, debate whether Jason and David could survive Burning Man, talk about finally getting into Harry Potter, and reveal what they’re trying to do to take back control of their algorithms. Learn more about your ad choices. Visit podcastchoices.com/adchoices