Trading Secrets

This week, Jason is joined by Kyle Cooke — entrepreneur, reality TV personality, DJ, and founder of Loverboy — for a conversation on what it really takes to build, scale, and fight to save a consumer alcohol brand in real time.
Kyle shares the full story behind Loverboy today — from once scaling to 30 employees, 200-plus distribution agreements, and national attention, to now operating with just three full-time employees while navigating cash constraints, distributor challenges, and millions of dollars in debt.
He breaks down the unique economics of the alcohol industry — including why brands are legally required to go through distributors, how wholesalers and retailers cut into margins, and why selling alcohol is far more complicated than most consumer products.
Kyle also opens up about the financial pressure behind the scenes, including personally guaranteeing a $4.2 million SBA loan, still owing roughly $2.9 million, and needing to generate over $100,000 a month just to cover the loan payment after taxes.
Beyond the numbers, Kyle shares the emotional reality of entrepreneurship — putting $500,000 of his own money back into the business, laying off employees, losing his COO, managing strained vendor relationships, and nearly facing the possibility of bankruptcy.
He also explains how the support from Summer House fans helped save Loverboy through direct-to-consumer sales, merch pre-orders, and renewed demand after he vulnerably shared the company’s financial struggles on the show.
Jason and Kyle also get into the impact of reality TV on business, why Loverboy’s fan base remains so loyal, how public attention can both help and hurt a brand, and why Kyle has intentionally avoided capitalizing on personal drama in a way that feels cheap or exploitative.
From SBA debt and distribution nightmares to multiple revenue streams, DJing, brand partnerships, and rebuilding Loverboy with a leaner team, Kyle gives a raw and honest look at what it means to keep showing up when the business, the money, and the public pressure are all hitting at once.
Kyle reveals all this and so much more in another episode you can’t afford to miss!
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Host: Jason Tartick
Co-Host: David Arduin
Audio: John Gurney
Video: Marc Colcer
Guest: Kyle Cooke

This week on Trading Secrets, Jason Tartick is back with the Curious Canadian for another 30 Minute Thursday! The two break down the biggest moments from the Kentucky Derby and Met Gala, share some hilarious stories from Jason’s parents being in town, and recap this week’s conversation with Tom Patterson — including the business lessons, brand-building insights, and unexpected moments from the episode.

This week, Jason is joined by Tom Patterson — co-founder of Tommy John — for a conversation on what it really takes to build a nine-figure brand from scratch in one of the most overlooked categories in apparel.
Tom shares the full story behind Tommy John — from walking away from a stable six-figure career in medical device sales to betting everything on a simple idea: fixing a problem he personally experienced with men’s undershirts. With no background in fashion, no industry connections, and just a few thousand dollars, he set out to create a better product — one that would eventually disrupt the entire category.
He breaks down the early days of the business — spending roughly $5K to create his first 200 shirts, selling on consignment, getting rejected by retailers, and relying on sales skills to get in the door. From folding inventory himself to traveling store-to-store training sales associates, Tom shares what it actually looked like to build the business from the ground up.
Tom also dives into the financial realities of entrepreneurship — funding the business with savings, 401(k) money, and credit cards, going years without paying himself, and navigating the constant pressure of cash flow in the early stages.
The turning point came when Tommy John landed in major retailers and later experienced explosive growth through non-traditional marketing — including a breakthrough moment on the The Howard Stern Show that led to record-breaking sales and ultimately shaped the brand’s entire marketing strategy.
Tom explains how the company scaled from a startup to a nine-figure business, including the importance of product innovation, brand differentiation, and building a loyal customer base in a highly competitive space. He also shares how strategic partnerships, celebrity endorsements, and a diversified marketing approach helped fuel long-term growth.
Beyond the business, Tom opens up about the personal side of the journey — including the stress, burnout, and panic attack that forced him to reevaluate his leadership style, priorities, and overall approach to building the company.
From burning the boats and betting on himself to navigating growth, risk, and long-term scaling, Tom gives a raw and honest look at what it really takes to turn a simple idea into a category-defining business.
Tom reveals all this and so much more in another episode you can’t afford to miss!
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The boys are reunited! 30 Minute Thursdays are officially back to normal—and so is Jason. After a long “work trip,” Jason reunites with David to get caught up on everything he missed. David fills him in on the latest—from Stagecoach stories to what’s been happening in the market—before the two dive into a hilarious recap of last week’s episode featuring Jon Bouffard.

This week, Jason is joined by Jon Bouffard — creator, entrepreneur, and one half of one of the most recognizable couples brands on the internet — for a conversation on what it really takes to build a business from nothing and scale it into a multi-six-figure operation.
Jon shares the unconventional path that led him here — from making $15/hour across a series of jobs, including teaching, working at Wells Fargo under a fake name, and serving as a vocational counselor, to eventually pivoting into occupational therapy where he capped out financially and began searching for something more.
Everything changed when he partnered with his now wife, Alex, stepping into the world of wedding videography. What started as a creative side hustle quickly grew into a full-time business, scaling from $3K to $10K per wedding — but also came with burnout, long hours, and limited upside.
Jon breaks down the turning point — when brand deals began replacing wedding income, allowing them to shift fully into content creation. He explains how their business evolved into a six-figure-per-deal model, what brands are really paying for, and why consistency and relatability have been the foundation of their success.
He also opens up about the realities behind the scenes — the pressure to constantly create, the mental toll of staying relevant, and the discipline required to keep showing up even when you don’t feel like it.
Beyond the business, Jon shares insight into how he and Alex divide responsibilities, manage finances, and maintain a strong partnership while building together — including why they prioritize simplicity, avoid unnecessary spending, and focus on long-term stability over short-term flash.
The conversation also dives into bigger-picture topics — from the future of the creator economy to the challenges of transitioning into traditional media, and the importance of protecting your personal life in an increasingly public world.
From $15/hour jobs to building a scalable digital business, Jon gives a raw and honest look at what it takes to bet on yourself, stay consistent, and turn creativity into a career.
Jon reveals all this and so much more in another episode you can’t afford to miss!
Subscribe to the Trading Secrets podcast!
Host: Jason Tartick
Co-Host: David Arduin
Audio: John Gurney
Video: Marc Colcer
Guest: Jon Bouffard
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