About three years ago, I had the opportunity to work with a global business, they were worth about $2bn.
They had asked me to develop some repositioning work, to move them from competing in their category, into a new space - a new category, so they could not just a category leader, but in a category of one.
There are lots of super interesting brands who are (arguably) in a category of one.
Sometimes they define the category, and others follow. Sometimes they’re eponymous to the point where any other brands don’t really matter. Sometimes they’re niche, and no-one would have the experience or chutzpah to step into the same space.
I remember working on Reckitt Benckiser for a couple of years, and marvelling at what seemed to be a portfolio of categories of one type products, they’re interesting beasts.
So the opportunity to ‘create’ an entirely new category was something I jumped at.
Then we got into budget conversations.
“We’re moving quickly, we need to announce this in the next month”.
They had put aside around $5k for strategy.
Putting aside the budget for a moment - the idea they wanted to reposition their entire business, and had given themselves less than a month, is hilarious at best, offensive at worst.
Bringing the budget back to the table - the shift in to a new category was the plan to see themselves more-than-double their market value. But their investment into that shift? I’ll let you do the math.
I declined.
Not because I didn’t want to do the job.
Not because I didn’t need the money.
Not because I didn’t think I could do a good job.
But because I knew how under-valued, under-appreciated, and under-utilised the work would be.
When you buy advice for $1m, you sit up and pay attention.
When you buy advice for $1, you can easily ignore it.
(📣 Wanna share your stories of working as an independent strategist? Let me know. )
Each week, I’ll try to profile one of our members, so you get to know each other better, and find folk you might want to connect to. Shout if you fancy having your face here.
Hey, I’m Carlyn Sylvester
Originally from Washington, D.C. and currently living in Los Angeles with my deaf senior bunny Bubs.
I’ve spent most of my career leading and building zero-to-one teams and initiatives at consumer-facing, content-driven brands like Spotify, Glossier, YouTube and most recently Netflix.
I left corporate 9-5 just over a year ago and am advising/consulting, while also working on a personal venture of my own.
I’m finding my consulting sweet spot is partnering with founders and leaders at early-ish ventures/brands in creative industries, at the intersection of content and consumer. I primarily do a combination of brand x innovation x incubation strategy work for creative businesses that have found early product-market-fit and are now looking to build and grow.
Also important -- I find inspiration in the little things in life: hygge, hot dogs, reality TV, national parks, my library card, and fly fishing.
I had a lot of fun as the fractional marketing/strategy lead for a small, family-owned dairy brand here in California, who was looking to evolve from a wholesale/retail model to D2C subscription. I spent six months working with them on the “what” and “why” and “how” – and also fleshed out their content/marketing strategy + longer term resourcing model. I had never worked with cheese before…Learned a lot and also got to spend quite a bit of time outside / on the ranch.
I’m especially enjoying working with creative-first entrepreneurs working on early creative businesses. Some recent examples: Working with the MD/Head of Brand at a boutique creative agency to think through how to incubate a new business model and his newly established team; working with an award-nominated producer on the ‘Season 2’ sponsor and content strategy of her high-reach podcast; working as a thought partner to the founder of an indie music label / media company who recently left ‘the majors’ to start building on his own.
Three things I’m reading/consuming/loving at the moment:
Watching - Severance. Haven't been this into a show since LOST. I love diving into the Reddit post-episode discussion rabbit holes, reading through everyone's theories/conspiracies...and sometimes even rewatching.
Listening - I live in LA and our local public radio station (KCRW) has amazing DJs -- great for music discovery. Also, in a past/future life I would do sync licensing for tv/movie soundtracks, so I often pay extra close attention to music/score choices. Some of my recent favorites on repeat: "God Walked Down" by The Allergies (from Severance S2), "I Would Die 4 U" - Holly Humberstone (from Shrinking S2), "Paraiso" - Gizmo Varillas, "Soul Finger" - The Bar-Kays
Reading - Two recent reads that sat with me for days afterwards: Playground by Richard Powers, All Fours by Miranda July. I'm also loving July's Substack, too.
Doomscrolling - I'm into this "foreshadowing" edit trend!
I spoke to Tan Doan, creative at The Crown & Co, a creative content studio specialising in storytelling for paper and screen, about their new project, exploring the parallels between run culture and entrepreneurship, and to celebrate people who drive positive change in their communities.
Q. What is Run Don't Walk?
A. We're a platform all about celebrating people who are doing things differently - whether they're starting a business, creating a new product, or building a community. We want to share their stories to inspire others and show that they can do it too. So the goal is to encourage people to take action - whether that means finally launching that business they’ve been talking about forever, getting involved with a local community project, or signing up for that writing course they've always wanted to do. The name 'Run Don't Walk' was a way to sum it up - as in, don’t overthink it, have some fun and go for it.
Q. Where did the surprising insight/overlap between runners and entrepreneurs come from? Why do you think there's a parallel?
A. We’ve always felt that whether you're a casual 5k park runner or an elite athlete, the key thing is 'showing up'. You've got to be wired a certain way to drag yourself out of bed, head to the park, and run on a cold, grey Sunday morning. So, we figured if these folks have the drive to do that, they're probably more likely to follow through on starting a business or launching a project. We’ve met so many amazing people at social run clubs, and once you get to know them, you soon realise that a lot of them have cool jobs, side hustles, or big plans for exciting projects. That reinforced what we’d always thought.
So, while we're called 'Run Don't Walk,' we’re not really about running in the health and fitness sense at all. It’s more about the community and that positive mindset. There’s something special about the energy in the running scene - people are often so open, generous, and eager to share ideas. We wanted to bring that same spirit into the stories we tell and the ideas we explore.
Q. This is both a digital and print zine - why print?
It just made sense for us to create a printed zine since a lot of what we write about focuses on community and human connection. Having a physical product really encourages readers to be more 'offline.' Plus, we love the craft of working with print - it’s so much more fulfilling. We get to collaborate with a bunch of new creatives, like writers, illustrators, and photographers. Our zine is stocked in hundreds of cafes across London, and it's always a joy to randomly spot someone sipping a coffee and reading our zine instead of endlessly swiping and scrolling on their phone.
Q. We know that more diverse cultural perspectives are a goldmine of insights - why is it important to you and the team?
A. With hybrid working, changes in nightlife, and the ever-growing influence of social media, a lot of us are feeling a little more disconnected these days. That’s why it’s so important to push each other to get out there—attend events, join communities, and just meet up more often. That’s where real connections happen, the kind that lead to meaningful conversations, stronger relationships, and a deeper understanding of the culture around us.
At RDW, we love shining a light on people making that kind of impact, like James Massiah, who started Adults Entertained, a literary poetry event, Yus, who runs a chess club called Knight club and Lydia Sanders, who founded Runner Beans. It’s all about sharing their stories and supporting projects like these so they can keep going and growing.
» Check out Run Don’t Walk
» Uri Baruchin asks “It's ten past AI, do you know where your brain is?”
» Kiana Fathi on the return of third-spaces
» Adrian Jarvis on systems thinking for brand designers
» 20 charts that show how everything changed - five years on from COVID
» De-Extinction companies. Jurassic Park is around the corner?
» Witnessing the death of capitalism
» All-in (but not freelancers) - Matthew gets ranty again
» Three Future Frames - An intuitive framework for design futures
» Remodelling the internet - post-facebook communities
Wanna share your work, ideas or thinking with the community? - drop me a message, and I’ll pop it in the next issue. This is a scrapbook of our ideas, so please open up your brains.
Runway East Bloomsbury, London UK. Waiting for a meeting, machine coffee, branded mugs. I love a branded mug. Tempted to pop it in my bag. For the public record, I didn’t.
Tell us where you’re sat, who you’re working with, what you’re drinking and thinking.
Every week, we share a list of roles found and shared via the the community. Some are directly from businesses who come directly to share their briefs with us. You can get these in real-time if you’re on whatsapp, telegram and slack.
Head of Digital Engagement (1 year Maternity Cover) (Woking,UK)
https://outsideperspective.co/gigs/20250313-wwf.html
Market Insights Lead - Fixed Term Contract (London,UK)
https://outsideperspective.co/gigs/20250313-tiktok.html
Brand Strategist with deep-science healthcare exp (remote,US)
https://outsideperspective.co/gigs/20250313-pinto.html
Bilingual (EN/SP) Marketing and Communications Strategist (Remote)
https://outsideperspective.co/gigs/20250313-moira.html
Head of Strategic Consulting (FTC-15 months) (London,UK)
https://outsideperspective.co/gigs/20250313-hogarth.html
Strategy Director (FTC 6 months) (London,UK)
https://outsideperspective.co/gigs/20250313-dentsu.html
Strategy Directors w/ fashion and retail comms experience. (London,UK)
https://outsideperspective.co/gigs/20250313-creativehood.html
Strategic Communications Manager (Remote,UK)
https://outsideperspective.co/gigs/20250313-climate.html
Freelance Senior Social Strategist (Seattle, WA, USA)
https://outsideperspective.co/gigs/20250312-copacino.html
Digital / Social Strategist (USA)
https://outsideperspective.co/gigs/20250311-ab.html
That’s all for this week.
mk ✌️
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