Trading Secrets

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
Upwork 
Scaling a business takes the right expertise at the right time. Upwork helps growing teams quickly bring in specialized freelancers—so you can move faster and take the business to the next level
Upwork.com
One Skin 
Founded by an all-woman team of longevity scientists, with PhDs in stem cell biology, skin regeneration, and tissue engineering – OneSkin is rooted in real science and expert research
OneSkin with 15% off oneskin.co with code TRADINGSECRETS
Booking.com 
If your vacation rental isn’t listed on Booking.com, it could be invisible to millions of travelers searching the platform. Don’t miss out on consistent bookings and global reach. Head over to Booking.com and start your listing today. Get Seen. Get Booked on Booking.com

On this 30 Minute Thursday episode, the Curious Canadian and Kathryn Hurley dive into the latest in pop culture while giving a behind-the-scenes look at life in their new home. Kathryn shares the hilarious quirks she’s discovered about Jason since moving in—from unexpected habits to everyday moments that make cohabitation anything but boring. It’s equal parts business, pop culture, and comedy.

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.

This episode of 30 Minute Thursdays features the Curious Canadian stepping in for Jason alongside Blake Horstmann, diving into the evolving DJ world—from turning a passion into a career to the realities of breaking into the industry—before shifting into a full Coachella recap, covering everything from behind-the-scenes insights and festival culture to a firsthand breakdown of Justin Bieber’s headline-making performance, all in a fast-paced, fun, and easy-to-follow 30-minute conversation.

This week, Jason is joined by Matt Halper and Eli Sones — the duo behind Two Friends, for a conversation on how they turned a college hobby into one of the most successful independent DJ brands in the world.
Starting as best friends making music for fun in middle school and college, Matt and Eli share how they took a leap after graduation with no real income, betting on themselves in an industry dominated by record labels. What began as small gigs paying a few thousand dollars quickly evolved into a global touring business but not without years of uncertainty, financial risk, and reinvestment.
They break down the real business of being a DJ today,  revealing why the majority of their revenue doesn’t come from music, but from live shows, brand partnerships, and building an experience-driven brand. From early days barely breaking even to landing six-figure deals and major residencies in Las Vegas, they explain how they scaled strategically while staying independent.
They also dive into the viral success of their Big Booty Mixes and why, despite millions of listeners, they’ve never made a dollar directly from them. Instead, they reveal how free content became their most powerful marketing engine, driving ticket sales, brand deals, and a loyal fanbase around the world.
Jason and the guys also explore the future of music and technology, including how AI is changing the creative process and lowering the barrier to entry for new artists and what that means for the next generation of creators.
Matt and Eli reveal all this and so much more in another episode you can’t afford to miss!
Pebl 
Pebl is an AI-powered global Human Resources platform built for founders, HR leaders, and operators who are hiring and supporting teams around the world
Go to hipebl.ai to get a free estimate.
Quince
Right now, go to Quince.com/tradingsecrets for free shipping and 365-day returns
WhatNot 
Whatnot is the largest dedicated live shopping platform, whether it’s beauty, collectibles, electronics, luxury fashion  — even cookies — sellers are building real, thriving businesses.
WhatNot.com
Momentous 
Head to livemomentous.com and use promo code TRADINGSECRETS for up to 35% off your first order