We’re excited to introduce you to the always interesting and insightful Sam Jennings. We hope you’ll enjoy our conversation with Sam below.
Sam , looking forward to hearing all of your stories today. Can you share a customer success story with us?
In 2001, the musician Prince had just completed a tour, and he wanted to release his first ever live album. I was working for him at the time on creative internet projects, but he tasked me with creating the album package. Combing through hundreds of photos taken by Afshin Shahidi, and reading through hundreds of fan reviews we had collected on Prince’s official website, I set about to create a package that inspired the listener as much as the concertgoer. I wanted to connect that energy to the album package, and get people excited all over again Prince’s live experience.
The album was called “One Nite Alone… LIVE,” and was released in the fall of 2002. The finished package was a long box filled with 3 CDs, a poster, and a tall booklet that was filled with photos and quotes from the fans who had attended the shows. Prince was very happy with the end result, and we sold out of them from his website store. At that time, Prince and I had created an online business that sold merchandise and music directly from Prince’s own company. It was one of the first artist-owned online businesses ever.
Almost 20 years later, The “One Nite Alone… LIVE” album was scheduled to be re-released, and Sony, the company handling the re-release, asked me to redesign the entire box set and update it for a new audience. This time it would consist of a 4CD/1DVD package, plus a booklet, and an entirely new version of the package released for vinyl. It was both meaningful and challenging to revisit a project that I had collaborated with Prince on. I realized it was my first time working on a Prince project without him, since he had left us years earlier. It was my goal to honor our first collaboration and give it some new life. I had grown as a designer tremendously in 20 years and had a few new tricks up-my-sleeve to dust off the old package with. And working on the vinyl version was a whole new challenge that I was eager to rise up to.
“Up All Nite: The One Nite Alone Collection” was released in 2020 and I was very proud of the finished product. With some re-edited photos, new images, updated fonts, and a more streamlined presentation, I felt I delivered something that honored the past, but was fresh enough to be considered it’s own release. It was an honor to get to work on this project 2 separate times, and once again feel that connection to Prince’s music that had been such a big part of my life.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I grew up in Chicago and attended college at the School of The Art Institute of Chicago (SAIC). It was at SAIC in the mid-90s that I discovered the internet as a creative tool, building websites, creating digital art, and really delving in to this new paradigm. I began to seek out connections with like-minded people who were in to the things I was in to, and the internet provided a worldwide network of people I had things in common with. One of those things was a love of the musician Prince’s music. I connected with other fans in Chicago and I started throwing get-togethers and event, all the while building up a database of Prince fans worldwide.
In 1998, Prince decided he wanted his fans to create a website for his charity, Love 4 One Another. I was asked to join the collective working on the site, and my years building websites professionally got the site launched and in line with Prince’s vision. Prince and I then began a collaboration that led to the first ever artist-owned online music service, Prince’s NPG Music Club (NPGMC). The NPGMC gave Prince an unheard of direct channel to his biggest fans, sending them new music on a monthly basis for a small fee. For years Prince had been trying to figure out a way to circumvent the record business and their chokehold on all the channels to his audience. The NPGMC was free and clear of all industry middlemen and gave Prince the unique ability to release music on the timeline he chose.
The NPGMC evolved and changed over the years, but in 2006 it was recognized with a Webby Award for Best Celebrity Website, and Prince himself was given a Webby Lifetime Achievement Award.
Since working for Prince, I have had full time design positions with Pearl Jam, Microsoft, EBONY Magazine, Avril Lavigne, and local agencies here in Los Angeles.

Have you ever had to pivot?
My biggest career pivot came in 2011. I had moved to Seattle to work with the band Pearl Jam, but that collaboration only lasted about 2 years. So while in Seattle, I began to look for my next job, ideally with another band or artist. After months of looking, it just wasn’t happening. I did small freelance projects for Steve Miller Band, Gorillaz, David Bowie, and a few more, but they didn’t lead to the full time position I was looking for. Being in Seattle didn’t help. If I could do it again, I would have immediately moved to Los Angeles, but I was hoping to move with my next position, whether that was in LA, NYC, Chicago, Atlanta, Boston, etc.
So being in Seattle, and getting nowhere in the music space, I decided to try my hand at UX Design at Microsoft. To say it was a departure from what I had been doing would be a tremendous understatement. But the team I interviewed with took a chance on a ‘rock star web designer’ and hired me to work on UX projects for the Microsoft Office Team. This was a huge career pivot. I wound up spending the next 5 years learning about working on large teams, corporate structures, principles of UX design, consumer testing, and so much more. And I will say that Microsoft is a great company to work for. The pay is outstanding, the benefits are even better, and all the people I worked with were immensely talented.
In the end though, I decided the UX life was not for me. I missed the creative energy of the entertainment industry, and I wanted more ownership of my projects, not just part of a massive team effort. I moved to Los Angeles and never looked back. I suppose that could be career pivot number 2, righting the course of my career back to entertainment.

Where do you think you get most of your clients from?
The best source of new clients has always been networking. With very few exceptions, I have gotten all my professional design gigs from word-of-mouth. Someone will know of a need and recommend me, or existing clients will bring me along on a new project or new line-of-business. Of course doing a great job is a must-have part of the equation. And as long as I deliver a strong project and prove I am easy to work with, I’ve had no problem getting recommendations to new and exciting opportunities.
Contact Info:
- Website: https://samjennings.com
- Instagram: @samjennings3000
- Facebook: https://www.facebook.com/samjennings3000
- Linkedin: https://www.linkedin.com/in/samjennings/
- Twitter: @samjennings
- Other: https://twitch.tv/samnation3000

