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Guess This Song In One Note Guy On TikTok Powered Entrepreneurship


Guess This Song In One Note Guy: On TikTok Powered Entrepreneurship 

Away from the standard story of influencers with a dream to be heard and recognized, Derrick Castenholz started social media to prove a point to his team, keep his business rolling during tough times, and minimize marketing budgets. 

While many may not know him by his name, he is best recognized as the “Guess This Song guy,” Today, we sit down with him to learn more about his inspiring journey and how he started the one note challenge that made viral video after another. 

Guess This Song In One Note Guy: On TikTok Powered Entrepreneurship 

Who Is “Guess This In One Note Song Guy”?

Guess This Song In One Note Guy: On TikTok Powered Entrepreneurship 

Based out of Detroit, Michigan, Derrick is a musically talented, family-oriented creator who worked as a financial advisor for over 18 years before dropping it to pursue his music career and become the life of endless parties and events.

He tells us,” Music has been a significant part of my life since my early years of upbringing when I was learning all instruments, that built my confidence to master the turntable.”

With no marketing or social media experience, Derrick Castenholz traversed the social media space with hopes of finding what resonates with a majority to help reach a niche audience. 

When and Why Did You Take Your Business to TikTok?

Guess This Song In One Note Guy: On TikTok Powered Entrepreneurship 

Like many business owners who had no pre-existing social media presence before the pandemic, Derrick’s push toward content creation was influenced by the fear of losing his business during challenging times. 

He tells us, “I’ve always believed that social media can work wonders for businesses. I loved the idea of free organic reach, but my duty towards my team as a founder is what pushed me to pick up the camera.” 

He adds, “I originally wanted other team members to give it a shot as they may be more familiar with the space, but all were hesitant. So I, a man of almost 50 years, decided to give it all I’ve got, and here we are a few years later with over 500k followers..” 

With his relatively new business relying solely on word of mouth and paid ads, Derrick managed to go from 3 to 4 team members to over 10 active DJs and turned unprecedented threats into an opportunity for growth. 

Tell Us About How things Took Off

Guess This Song In One Note Guy: On TikTok Powered Entrepreneurship 

“I like to call the starting phase “seeing what sticks,” after a long back and forth of trying to find what works, I settled upon studio videos inspired by the old TV show Name That Tune, along with live Q&A sessions.”

However, the pivotal moment for Derrick’s business was when he started getting feedback from followers, building relationships, and creating an outlet of discussion, which in return brought the “Guess The Song in One Note” Challenge into existence.

Derrick explains that the street interviews that he considers a golden ticket for DJ DC Productions were originally the idea of a fellow DJ based in Seattle who proposed that Derrick should take his studio sessions to the streets and get real-time reactions. 

Is Content Creation Limited to Business, Or Will You Take the The Influencer Route?


Can you help him out? What is it?

♬ original sound – DJ DC

“All my attention is focused on growing the company, and we’ve been seeing a constant increase in clients through TikTok, so diverging from that into other creative pursuits will hinder the progress of the original mission.”

Navigating the online space with tunnel vision to expand and grow DJ DC Productions, Derrick is firm on his goal to build an entertainment empire and discover new areas of opportunity for him and his team. 

What Formats Worked For Your Business? 

Answering our question based on performance, engagement, and the feedback received from people, Derrick suggests the following formats for businesses to save time in the experimenting phase:

Street Interviews 

“Street interviews are long hours of work, but viewers want to see something genuine, especially if there is an exciting reaction because some of these challenges are difficult.”

Street interviews get the highest level of engagement, yet they’re one of the most time-consuming video formats for the minimal level of control you have over it as a creator.

Engaging Challenges

“The “Guess the Song in One Note” challenge goes beyond content creation, it’s not consumable content. it’s more of a fun online game in the form of a video.”

He breaks it down telling us, “Challenges gain popularity for engaging viewers in an emotional journey. When creating challenges you’re not only putting out content for consumption, but also building a relationship through interacting with viewers and interviewees.”


“I sometimes host live Q&A, take special song requests to incorporate in my next videos, and do the guess the song in one-note challenge live. I think it’s a faster way to build trust and is an algorithm-favored format.”

What Makes A Good Street Interview? 


Did you know the name of it?

♬ original sound – DJ DC

Relevance Of The Topic

“You’ll find that some of my best-performing videos are for popular artists and bands like AC/DC and anthems like Darude Sandstorm.” 

He emphasizes that the best-performing interviews are those based on relatable matters and that street interviewers must establish their questions or challenges upon common knowledge to get the best reactions. 

The People You Interview

“It’s the people. You have to find someone genuinely interested but also someone that others can relate to in terms of how they speak, dress, and react.”

“I’ve had some priceless reactions, and even if they don’t end up guessing the right song, their energy alone qualifies as a viral video because what are the odds of guessing a song from one note?” 

Derrick believes that viewers put themselves in the place of the interviewee, adding, “If they know the answer, they want the person to win, but if they don’t, they’d love to see them lose.

Offering An Incentive 

“Participants are much more open and excited to get the right answer when there’s an incentive involved; it doesn’t have to be a costly prize, but when there’s a reward, participants will care more about what you have to say, and shift into a competitive mindset.”

What’s Your Long-term Objective?

While other creators strive to pursue Hollywood roles, sell merchandise, and collaborate with bigger brands, Derrick’s long-term goal is to shift from being the center of the brand to being a CEO and handling only the business side of DJ DC Productions.

Aside from the end goal, Derrick is dedicated to keeping his staff active and allowing each passionate individual on the team to become a full-time DJ like himself. 

Tips For Entrepreneurs and Business Owners

Shift To Social Media 

“Venturing into the social media world, I knew absolutely nothing. I started content creation to prove a point to my guys, and it worked.”

“My advice for businesses in a similar niche is to save the marketing budget paid to promoters and third-party companies and pursue free exposure while the opportunity lasts.” 

Do Not Get Discouraged. 

Derrick stresses that well over 8 billion people on this planet, and at least 1% of them will find your product or service worthwhile.

He says, “New creators and brands on social media should adopt the positive mindset of viewing the growth process as simply locating your audience. Discover a few formats that people will remember you for and double down on them.” 

Try Street Interviews

Derrick holds a firm belief that the potential for leveraging street interviews extends across a broad spectrum, encompassing virtually any brand or business. Wrapping up his answers, he tells us”All it takes is a skilled camera operator, two microphones, and a strong sense of determination, and you’re poised for success.” 

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Moe is freelance writer and content creator who enjoys interviewing influencers and learning about their journeys to success.

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