Matt Schaup Coaching & Mastermind

Matt Schaup's entrepreneurial journey began at rock bottom. At 20 years old, he was "a couple hundred thousand in debt" with "a hundred dollars to my name." A banker had humiliated him, telling him he "wasn't good enough to make it in banking." That moment crystallized his initial purpose: "I decided 10 years ago, I said, hey, I'm going to be a millionaire as quick as possible." He remembered painting houses in college and decided to launch a residential painting company in Northern Colorado.

The painting business exploded. From nothing, the company generated $500K in year one, $1M in year two, $1.2M in year three, and by 2015 was doing $2.5M annually. Over the full decade, the business accumulated roughly $20M in cumulative residential painting revenue. By age 34, Matt had climbed what he calls "the million dollar mountain" and had built a team-managed operation that generated about $500K in annual net profit. However, something shifted.

As Matt's painting business matured, he started getting "accidentally" asked to speak and coach other business owners. These unexpected opportunities revealed something crucial: there was a void in the coaching space. While there were thousands of coaches and speakers with great content, Matt observed that few truly helped clients discover their deeper purpose and unique story. He started testing the coaching market in January 2016, initially juggling multiple revenue streams: one-on-one CEO coaching, his proprietary "life plan process" (a two-day facilitated session), keynotes, book sales, and a developing webinar product.

Among all his coaching initiatives, the mastermind group emerged as the fastest revenue generator. Launched at $99/month with a hard cap of 100 members, it reached 87 members by the interview date—generating approximately $8,700 in monthly recurring revenue. The mastermind offered daily inspirational videos from Matt, weekly conference calls featuring six, seven, and eight-figure entrepreneurs as guest speakers, interactive mastermind calls, and access to his developing video coaching product. Members wanted consistent exposure to Matt but couldn't yet afford his big-ticket one-on-one coaching rates.

Matt deliberately chose not to expand the painting company to $5M+, despite having the operational capability. His reasoning was clear: "It's not my purpose." He realized he "didn't bring other people up the mountain" with him and found no deeper meaning in chasing higher revenue from a geographically-limited service business. The digital coaching business offered unlimited scalability and alignment with his actual purpose.

At the time of this interview (early 2016), Matt was operating two distinct income streams: his self-managed painting company generating approximately $500K annually in net profit, and his rapidly-growing coaching business generating revenue from masterminds, one-on-one coaching, keynotes, and book sales. His unique positioning—going from $200K in debt to multimillionaire by 30, then choosing to help others find their purpose rather than chase more money—became his most powerful marketing asset. His authenticity and congruence between his message and his lived experience were what attracted customers, not generic inspiration platitudes.