Tales From the Hip-Hop Brand Strategist: Connecting Fashion, Music, & Strategy with Wes Henstock
Read time: 5 min
What do people typically get wrong about brand strategy? Why is a workshop so important? What does a strategist need to put on the line?
Wes Henstock is the Hip-hop brand strategist. Coming up in the world of fashion and music, he’s worked with folks like Damon John, and brands like Armani Exchange, DKNY, and Tommy Hilfiger. Wes is a Founder and CEO of Confid3ntial, a brand design agency and he is also an instructor at Level C, a brand strategy educational platform from the legendary Marty Neumeier.
In this episode, we dive into his journey and key pieces of wisdom for anyone interested in the world of brand.
WARNING: Explicit, entertaining, and educational
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In this episode:
The importance of strategy in the creative process
The power of strategy show & tell
Misconceptions about brand strategy
Workshops are critical to the alignment of the compony
Tips on running an amazing workshop
The Obituary Technique
The purpose of having a purpose
How strategy should be like Hip-Hop
Challenges in the healthcare industry
KEY LESSONS
Misconceptions About Brand Strategy
The term Brand Strategy is thrown around quite a bit and I wanted to hear what Wes had to say about it. To him, it’s really not that complicated, it comes down to a strategy that gives companies the best chance of winning.
“We can do all the foundations and all the frameworks we want, but at the end of the day, we have to use that work to then identify an opportunity or how we can minimize a risk for a company. To me, that's what strategy is.
This term brand strategy, we all do it, we're all guilty of it, but technically we're a business strategy”
And as a brand strategist, there is one critical job we all need to do:
“Just cause we’ve got a certificate doesn’t mean we’re strategists. A strategist needs to find the opportunity and then have the balls to say to a CEO this is what we believe is right. It’s gonna be scary, but you need to put it on the line… and we’re gonna help you through it”
Wes then talked about Wu-Tang and how only through their performance, releasing their tracks when they actually left an impression on people and that creates a brand. So if you have a brand strategy, you don’t actually become a brand until you activate it.
The Power of Strategy Show & Tell
Wes was very open about his dyslexia and when asked what he would say to Wes if he had a time machine, he would tell his younger self to embrace it and not to fret. I asked him specifically about his point-of-view about word vs. visuals and he had this to say:
“When we start creatively, we start with words, right? Let's talk about how this thing's gonna make us feel. Let's talk about how the impression or the perception we wanna leave. So before we start a project, let's talk about those words.”
We might start with words, a key part of his process is to turn it into a visual.
“Simplify the objective so it’s much easier to digest, much easier to sell. How do we visualize this strategy? Use Google and find me an image of what you’re trying to tell me…show and tell.”
Wes is most comfortable communicating through verse. He uses music, Hip-Hop artists, and metaphors when talking about his ideas and philosophy on brand. Even though some people don’t get it, he attracts the right people into his world.
Challenges in the Healthcare Industry
It was extremely interesting for me to get his take on healthcare as the Hip-Hop Brand Strategist and Wes offered his view on what’s challenging in healthcare
“You’ve got a risk of trying to being real but then really deterring people… People might be struggling with cancer and you want to hit’em with something real, creating that taboo, but is it really helping them?”
Ultimately, it’s the dance of being truthful and provocative, but asking yourself the question of “Is this helping them?”. So thinking beyond the ad, think beyond the brand video and get into spaces where you are helping people feel better.
“Why can't we create an app that goes along with a product that makes this person feel good? Why can't we create communities?”
Tips on Running an Amazing Workshop
The most important part of the process is the brand workshop, and I vehemently agree. Wes has a subtle opinion about this:
“If I could put you under the knife and operate on you for eight or sixteen hours - a full workshop - and it extended your life for 25 years, would you say no to me?”
Here are seven tips from Wes:
1/ Create a safe space for inclusivity and empowerment
“Some of the most successful strategies I've worked on that are being activated have come from the most unexpected person in the room. The person that's been given a voice for one time in their whole career in this business where they've actually just felt safe."
2/ Engage as large of a group as possible
"The point is, if we get everyone in that room, and you all align on this together, you all agree on this objective together, you all agree on this destination together, no one outside the room can then query it. You all know where you're going. You all decided this together."
3/ Learn and adapt constantly
"Every deck you create is because you've been challenged by something. So you add something to this deck... Let's adapt, let's test, let's learn."
4/ Be prepared for possible “oh shit” moments
“You need to remember, you cannot control the people, you cannot control the environment and you cannot control the time. Everything else you can prep for”
You can rework your frameworks, rework your deck to give you cues…once you’re in the room, you’re locked in”
Things Wes has in his “Magic Trolley”: Lozenges (he loses his voice), Allen wrench (a TV once came off), projector, candy, speaker, painkillers, markers, Post-its, water, energy drinks…
5/ Manage the energy of the room
The energy had dropped. You're a DJ at this point. You're playing a song. No one's dancing. They're like, I've had enough. I'm leaving the dance floor. You gotta read the room. So we put a different track on and we bring you back in and we change the energy and we try a different approach and we ask a few more prompting questions
6/ Straight and honest talk
“I've had some serious conversations with CEOs. 'This is where my belief in purpose is so strong that I've had to pull 'em (CEOs) aside and say, I just don't want you to give me this answer to shut me up to move on. Because if this is not an answer that you believe in, the rest of what we're gonna do right now is just gonna fall.”
7/ Support juniors, shadow seniors
“When I was doing it (first ever workshop), I was in a room and I had my boss at the time, or he'd be overshadowing… as a junior, you've got to get into rooms, you've gotta shadow, you've gotta observe”
Conclusion
Wes Henstock is the real deal. He’s grown up in the world of fashion and Hip-Hop as a creative powerhouse and now helping companies with strategies that can give them the best chance of winning. There are so many great gems in the episode that this short write up does it no justice. Go listen for yourself…