Dean Rud on Bootstrapping Success: From DIY Music to Boooooost Marketing
Dean Rud, founder of Boooooost Digital Marketing, has traveled an unconventional path to success, beginning with his time in a touring punk rock band. From bootstrapping his band's recordings and tours to leading a thriving digital marketing agency, Dean’s entrepreneurial spirit was forged through the DIY ethics of the punk rock community. His story offers a unique blend of creativity, independence, and passion, which he now channels into helping businesses grow through digital marketing. We asked him to reflect on his journey and how it shaped his current venture.
Did you see your current venture as a possibility when you were touring the world in a punk rock band?
Dean Rud, the founder of Boooooost Digital Marketing, has an unconventional path that led him to the world of digital marketing. His journey began in a place far removed from the corporate environment — as a member of a touring punk rock band.
The DIY ethic ingrained in the punk rock community played a significant role in shaping Dean's entrepreneurial mindset. "We bootstrapped most things on our own, including recordings, record production, and tour bookings," Dean explains. “Digital marketing was one of the tasks I typically volunteered for, and while I didn’t foresee this exact business, it feels like a natural extension of what I’ve been doing since the late ‘90s.”
Boooooost's ethos is not far removed from Dean’s early punk rock days. At its core, Boooooost is focused on building communities through education, information, and entertainment — much like how punk bands would rally their fans around shared values and experiences. “It’s about making a positive impact on as many lives as possible, whether that’s through music or marketing,” says Dean. This fusion of creativity, independence, and drive to make a difference has become the heartbeat of Boooooost Digital Marketing.
How has your business changed since its inception?
“Change has been the only constant,” says Dean when reflecting on how Boooooost has evolved since its inception. In the fast-paced world of digital marketing, where SEO algorithms and ad platforms shift daily, adaptability is crucial. “Every day we get a little better at delivering value to our clients, and every day the online marketing landscape changes just a little bit,” Dean adds.
To thrive in such a dynamic environment, Dean has developed a business philosophy rooted in frameworks and principles that transcend the constant changes in tactics. While Boooooost initially offered a wide range of digital marketing services, from website development to SEO and content creation across various industries, Dean foresees a more focused future. "I can see our focus narrowing on the horizon, and that’s going to be a significant shift for us," he notes. This shift will allow the company to refine its services and further elevate the value it delivers to clients.
What is a typical workday for you?
For Dean, no two workdays are the same. Balancing his professional life with family responsibilities, he divides his work into two to three parts throughout the day, often between school drop-offs and pick-ups. "Most entrepreneurs I know value this autonomy and flexibility of time more than anything else," he says.
Boooooost operates on what Dean calls “seasons” — periods that focus on varying priorities. Some seasons may prioritize “doing” over “planning” or “learning,” while others strike a balance between working in the business and on the business. This approach allows him to maintain flexibility while ensuring that all aspects of Boooooost, from client work to business strategy, receive the attention they need.
What have been some successes in your entrepreneurship journey?
When asked about his successes, Dean’s answer is as straightforward as his approach to business: “Not giving up.” Persistence has been a key factor in his entrepreneurial journey, alongside being present for opportunities when they arise and, as he puts it, "making our own luck." Dean also credits his hands-on experience in life and business for helping him navigate challenges and seize success.
One recent success for Dean has been his growing ability to adapt and incorporate evolving strategies into Boooooost’s digital marketing services. For example, refining his SEO offerings and customizing services to meet the specific needs of diverse clients has been a notable achievement.
What are some obstacles you've come across?
Dean is candid about the challenges he's faced. Surprisingly, most obstacles, in his experience, have been self-imposed. "I was very slow to start this business because I convinced myself I needed to plan everything out perfectly before engaging with the first client," Dean says. This "paralysis by analysis" was one of the earliest challenges he had to overcome, and it required both self-reflection and courage, along with support from peers.
Another major challenge has been the complexity of SEO, Boooooost’s primary service offering. "SEO is difficult to systemize because clients have such varying levels of understanding of its value," Dean explains. This diversity has made it tricky to streamline offerings, but it’s a challenge Boooooost continues to refine as the company grows.
Comparing where your business is today and where it was when you started, what has been the key(s) in helping you grow?
Dean points to four key factors in Boooooost’s growth: focus, commitment, persistence, and community. Staying focused on the mission and committed to long-term goals has been instrumental in Boooooost’s success. Persistence has kept the company moving forward even in uncertain times, while community — both the community they build for clients and the one supporting Dean personally — has provided the foundation for growth.
What led to your working with Guildstreet?
Dean’s introduction to Guildstreet came through one of the best marketing channels — word of mouth. "It came from another happy Guildstreet client," Dean says with a smile. “There’s no better recommendation than that.” This referral reflects one of Dean's core beliefs: happy clients lead to more opportunities. It’s a philosophy that has served Boooooost well as they continue to expand.
What advice do you have for anyone starting their own business?
Dean offers several practical insights for those considering launching their own business. First, he emphasizes the importance of getting organized early on to handle the influx of information and attention that comes with entrepreneurship. He recommends reading "Building a Second Brain" by Tiago Forte to help manage this.
For those still hesitating to take the leap, Dean suggests reading "The Millionaire Fastlane" by MJ DeMarco, which can provide clarity on the decision to become an entrepreneur. Once you’ve committed, Dean advises focusing on your target market and creating value for them. He references “$100M Offers” by Alex Hermozi as a helpful resource for refining your offers and finding product-market fit.
Dean also encourages new entrepreneurs to get in touch with their "why," a concept popularized by Simon Sinek. "It's crucial to understand not just what you're doing, but why you're doing it,” Dean emphasizes
Lastly, Dean advises new business owners to start today, keep going, and not be afraid to pivot when necessary. “Just make sure you make informed choices,” he adds. And one last tip? "Start the SEO work on your website right away to plan your content properly."
Dean Rud’s journey from punk rock tours to running a successful digital marketing agency highlights the importance of perseverance, adaptability, and staying true to one’s roots. Through Boooooost Digital Marketing, Dean continues to apply the DIY ethic he learned in the punk community, helping clients build communities and grow their online presence with the same passion and energy that once fueled his music career.
Connect with Dean Rud today
https://boooooost.com/
Written by Justine Beaulieu
