On this week’s 30 Minute Thursdays, Jason Tartick and David are back breaking down the biggest moments from their conversation with Kyle Cooke. They unpack the future of Loverboy, the realities of scaling a consumer brand, and the honest business conversations that had everyone talking.

Plus, the guys dive into the latest pop culture headlines, trending business stories, and Jason shares what happened when he visited the restaurant he recently invested in. From entrepreneurship lessons to reality TV chaos, this episode delivers the perfect mix of business and entertainment.

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

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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This week on Trading Secrets, Sistersnacking joins the show to dish on everything behind the scenes of the food influencer world. From their go-to favorite restaurants to the wildest brand deals they’ve ever landed, nothing is off the table. They break down how they actually make money in the food industry, what brands don’t want you to know, and the hustle it takes to turn snacking into a serious business.

Plus, they open up about what’s next—hinting at the possibility of creating their own cookbook and sharing the kind of recipes their audience has been begging for.