Shadow strategy for brand + business.

Face what's false. Feel what's real. Make the unspoken truth your unfair advantage and get unstuck for good.

Asa Goldstein, Principal, Roguish

Most 'brand strategy' isn't a strategy at all.

I know because I spent a decade running the playbook. It's consensus-driven, paint-by-numbers theater that feigns insight but delivers bloated decks, corny archetypes, and documents that sit in drawers.

The standard process validates rather than questions. No one reads between the lines of the research.

Your newfound 'clarity', 'alignment', and 'differentiation' aren't necessarily rooted in reality.

Nothing really changes. Tactic after tactic. Experiment after experiment.

Six months later, you're still hitting the same walls. Losing deals you know you should win. Fighting for survival rather than success.

ROGUISH asks a simple question: What if every stuck company is running from truths it dares not name?

I surface those shadows, name them, and sharpen them into the edge only you can own.


THE FIVE SHADOWS ↓

SHADOW 1

MARKET

What the market is lying to itself about.

████, an energy insight startup, showed households when energy was cleanest and cheapest in a consumer-friendly format. People said they only cared about saving money on their bills, so ████ sold savings and rebates.

The Edge: It wasn't about the savings. It was about control. Position as the provider of pure insight, not shame or restriction. Be the forecast that utilities license to buy back community trust.

SHADOW 2

PERCEPTION

How you think you're perceived vs. how you actually are.

█████, a productized laundry service, thought they sold convenience. Turns out homesick customers were buying surrogate care from their stay-at-home-mom gig workers.

The Edge: Recognize the real value. Embrace the odd-but-sweet relationship at play.

SHADOW 3

COMPETITION

The forces you're reacting to but completely misreading.

Every luxury yacht charter claimed to be "#1." Tricked ████ into thinking that spot was taken. Truth: none actually looked, felt, or operated like #1.

The Edge:
Become the institution everyone else is pretending to be—visually, verbally, and experientially.

SHADOW 4

INTERNAL

What your team knows is true but won't say out loud.

██████, a disruptive recruiting startup, had a provocative name that drove responses but screamed reckless; misrepresenting their careful, hands-on approach. Wanted to rename.

The Edge: Keep the name, recalibrate the brand. Turn grabbed attention into earned trust.

SHADOW 5

CORE

Your entire approach is built on a lie.

█████, an impact investing app, promoted financial literacy and a bright future to Gen Z... a generation of Doomers who distrust institutions and reject optimism.

The Edge: Tap their nostalgia for a future that never was and offer investing as community rebellion against the elite.

HOW I WORK

I work with founders and execs of early-to-growth-stage companies who've already tried the usual approach and mirror-back-what-you-said-but-prettier rebrands, got nowhere, and are finally ready to try something different.

THE 'PROCESS'

Direct, adaptive brand and business immersion.

My approach is tailored to expose and integrate the shadows—not confined to a predetermined checklist of workshops and surveys.

THE DELIVERABLE

A focused deliverable designed for immediate action. Usually a memo and a toolkit. Always a clear diagnosis, an implementation plan, and defined pivot options to account for the unexpected.

Can include: positioning, narrative, messaging, business models, offer architecture, creative briefs, campaign concepts, etc.

THE MODEL

My model is designed for results, not billable hours. It's a direct response to the inefficiencies and misalignments I saw running a traditional agency.

We agree upfront on a single, flat fee based on the stakes of the engagement. The key is that investment must be significant enough to ensure full organizational commitment, but calibrated to deliver exponential ROI.

The diagnostic takes 3-6 weeks, followed by 6 months of implementation oversight. No scope creep. No hidden costs.

THE PACT

We agree on a clear success metric before the engagement begins. You agree to commit fully to the plan and my guidance throughout implementation. If the metric isn't hit at 6 months, you get a 100% refund. It's a structural fix for a broken model where the client holds all the risk. All our work is strictly confidential.

I now see what I was missing all these years. Thank you.

FOUNDER, SEED-STAGE ENERGY INSIGHT STARTUP

This is an incredible experience for a business. You will not be disappointed.

CEO, PROFESSIONAL SERVICES FIRM

Asa brings a deep sense of empathy and undying curiosity that creates trust from day one.

SERIAL FOUNDER, CLEANTECH + CPG + AGTECH

Asa cuts through ambiguity with piercing questions while enriching the process with camaraderie and positivity.

CEO, CREATIVE AGENCY

Easy to work with, responsive, and offered true insight.

FOUNDER, SERIES A ALT-PROTEIN STARTUP

Asa is a branding & strategy guru. His ability to craft compelling brand stories is remarkable to experience.

CO-FOUNDER, SEED-STAGE FINTECH STARTUP

Book 5-Min Consult

Instead of proposals and hour-long pitches. We can determine if there's a fit for us to work together in a single, 5-minute call.

You tell me what's stuck. I'll let you know immediately whether I'm the right person to help.

Book 5-Min Call

FAQ

How do I know you'll be right in your diagnosis?

You don't. I don't claim to be omniscient or infallible. You know the facts of your business better than I ever will; my role is to reveal the pattern you're too close to see and offer the courage to face it.

In fact, in many cases, you already know the truth. I provide the framework to address it head-on. The goal isn't for me to be "right"—it's to provide a diagnosis that works. The guarantee is my bet that it will.

What if I disagree with your diagnosis of the shadows?

That's to be expected from time to time. This is why there's an explicit choice built into the process. After I deliver the diagnosis and plan, you have one week to decide:

1. Commit. You execute the plan for 6 months under my oversight. The full-refund guarantee stands.

2. Walk away. The engagement ends. I refund 30% of my total fee, no questions asked.

How do we set the success metric?

We agree on a hard, measurable leading indicator during our call. The logic is simple: I risk my fee, but you risk six months of runway. Since a refund cannot buy back lost time, we are both forced to set a target that is ambitious enough to matter but realistic enough to hit.

How do I know if I've broken the pact?

I don't use loopholes. If you are about to make a decision that compromises the strategy, I will warn you before you act. At that moment, you have a choice: do it your way and void the guarantee, or stick to the plan and keep your safety net.

Is this just brutal honesty for the sake of it?

No. Truth without finesse is just noise. My job is to make it usable. I disarm the room with compassion and candor so we can sharpen an uncomfortable reality into a competitive edge.

As you can see in the case studies, the truth is more often awkward than it is painful. It's difficult for insiders (or misincentivized outsiders) to name those truths without sacrificing their political stance. My job is to care more about what's real than what we wish were right.

What if my team isn't ready for this?

Readiness isn't comfort; it's courage. If your team requires total consensus to move forward, we won't be a good fit.

Do you work with [specific industry]?

I work across industries. The shadows show up everywhere—tech, finance, healthcare, CPG, professional services.

The guarantee forces me to stay sharp on a wide variety of market conditions, business model fundamentals, and what's actually solvable. I can't afford to take on projects where present or upcoming external factors will torpedo any strategy regardless of its efficacy otherwise.

If the solution is outside my expertise, I have a private network of specialists I'll refer you to.

What matters isn't the industry. It's whether you're genuinely stuck on something I can help with.

Is this only for companies who've been burned by the branding process?

No. Some call me after they've spent a fortune. Sharper ones call me before.

My work stops at the strategic foundation. I deliver the diagnosis, the toolkit, and the plan.

A great agency can then 'build the house' off the specs. Truthfully, a good freelancer—or even someone off Fiverr—executing a logo rooted in authentic positioning and clear direction is more likely to get results than an all-star team doing a $1M brand identity that rings hollow.

Execution matters, but it's secondary. My job is to make sure you're building off solid rock, not a swamp.

Do you ever operate as a fractional CMO?

Occasionally. Model is different—flat monthly fee depending on time commitment, no refunds. Pure advisement.

About ROGUISH

My industry sells feel-good narratives and consensus-driven processes that fail to challenge the beliefs holding companies back. They preach radical differentiation but all hide behind hourly billing and safe roadmaps that incentivize stalling.

ROGUISH is the antidote. It's a model built on accountability and a process that uses disciplined skepticism to reveal the core, resonant truths most branding exercises miss.

On the other side of the discomfort is the differentiation everyone's chasing but few are willing to earn.

Work in the Shadows

THE REAL MEAT

Client: Mycoprotein ingredient startup

SHADOW: Competition, Market

What they thought: Offer plant-based ingredients to establishment meat makers in alignment with modern sustainability initiatives.

What was true: Sustainability coordinators had no decision-making power and were largely performative. Factory farmers care more about costs and quality than going green.

They were pitching fermentation mycoprotein to meat makers the same way every other alt-protein company did—sustainability, ethics, environmental impact, flavor. All the things that made sustainability coordinators nod and CFOs ignore.

Reframe: don't sell sustainability. Sell better margins and better meat. Good optics was the bonus.

The fermentation process became "brewing"—like beer and cheese. Familiar, artisanal, a craft the meat industry could understand. Positioned the ingredient as making their existing product better and cheaper, not replacing it with something foreign.

Stopped trying to change minds. Started speaking the language of people who actually wrote checks.

THE OUTSIDERS

CLIENT: Regional healthcare provider

SHADOWS:
Perception, Internal, Market

What they thought:
We need to communicate our impact better.

What was true: No matter how much good they did, people still disliked and distrusted them.

Community health org in red political area. Medicare-funded. Wonderful, impactful work.

Unspoken accusations surfaced in the hard conversations: "government handouts."

Not only did they face insurance provider stigma (well-earned, in most cases) but they used 'liberal-coded' language—"equity," "access," "underserved communities"—in a place where "bootstraps" and "self-reliance" were cultural currency.

Community saw them as outsider charity enabling dependency.

The reframe: "Homegrown Healthcare"—locally run, locally funded, by and for the people who live there. Same services. Different story.

"Access to care" became "neighbors helping neighbors." Highlighted local partnerships, local staff, local board.

THE SPECIALIST MYTH

CLIENT: Mid-Size Law Firm

SHADOW:
Core, Competition

What they thought:
We need to specialize or pick a vertical to have a coherent brand.

What was true: The through-line wasn't what they did. It was who they served.

30 practice areas. Impossible to differentiate. Constantly adding new services to attract business. Almost never the top choice. Entirely referral-based.

Looked at the emotional context instead of services. Dug into their favorite and most profitable client relationships. Pattern across every practice area: people protecting something they built or were trying to build. Always dreamers.

"We protect dreams" unified everything without shrinking the service offering. Reshaped their messaging, client selection, and pricing.

Gave clients a reason to choose them over the specialist down the street.

THE COMMODITY TRAP

CLIENT: Lead generation provider

SHADOW:
Core

What they thought:
Sell superior email lead gen tactics to clients who need more prospects.

What was true: Clients don't need another vendor promising tactics. They need someone who actually knows which tactics and vendors are legit.

Lead gen service run by a team of incredible sales veterans. High judgment, high value, decades of experience. Positioned around their proprietary email system—better data, higher deliverability, more qualified leads. Competing in a space flooded with Joe Schmo providers all claiming the same thing.

Impossible to keep up. Tech shifts constantly. Regulations change. What worked last quarter gets flagged as spam this quarter. They were exhausting themselves staying ahead while clients couldn't tell the difference between them and bottom-tier list brokers.

Core shadow: they had something genuinely rare—judgment, experience, actual customer service and relationships—and they were competing like they sold commoditized tactics. Trying to out-execute on the thing that mattered least while ignoring what made them special.

The insight: stop competing on execution. Compete on judgment.

Reframe: become the trusted broker who helps clients navigate the wilderness of bad vendors and implements proper oversight. Stop charging for tactics. Give away counsel for free, then take referral cuts from the handful of partners who actually deliver.

Not "we have the best deliverability." Instead: "we know who's full of shit and who isn't, and we'll make sure you work with someone who'll actually do it right. Then we'll make sure they kill it."

Same expertise. Different monetization. Suddenly they weren't another commodity vendor—they were the only advisors clients could trust to guide them through the chaos.

THE GROWTH DELUSION

CLIENT: Marketing firm for credit unions

SHADOWS:
Market, Competition

What they thought:
We help credit unions with brand strategy and marketing. Need a better process to differentiate from larger firms

What was true: Their clients were disappearing through consolidation, and the survivors needed something else entirely.

Built their business on growth marketing, member acquisition, brand refreshes. But the credit union industry was rapidly consolidating. Small credit unions weren't looking to grow, they were merging or getting absorbed. The ones that survived the merger were bleeding culture, staff, and member loyalty.

Their real value wasn't pre-merger brand strategy. It was post-merger integration: rebranding the combined entity, merging cultures without losing what made each one matter, keeping members from jumping to big banks during the chaos.

Everyone in their industry was still selling "growth marketing" to institutions that were being erased or brand management to established players that were in flux. Reposition: solve the post-merger identity crisis no one wanted to admit was killing their clients.

THE FORCED FUN PARADOX

CLIENT: My own startup, QuestWorks

SHADOWS: Perception, Market, Competition

What I thought: We need to make remote team building less cringe by designing better experiences.

What was true: The cringe isn't the activity. It's the coercion. Mandatory fun will always feel mandatory.

Started a team-building company because I'd sat through enough coffee chats, icebreakers, and virtual pizza parties to know the industry was broken. Every experience felt performative—cringeworthy, patronizing, something employees endured rather than enjoyed. Completely incompatible with the younger workforce's social habits and expectations of modern workplace culture.
‍‍
I thought the play was to design genuinely good experiences—things people would actually want to do. Make them thoughtful, remove the awkward facilitator energy, focus on real connection.

Missed the actual problem: it wasn't the quality of the experience. It was the structure itself. Scheduled team-building asks people to perform connection on command. The best teams bond organically—through shared challenges they choose to take on together.

The reframe: stop scheduling connection. Create the conditions for it. Multiplayer gaming works because strangers opt in to shared quests. No mandatory attendance. No performative ice-breaking. Just voluntary, bite-size challenges that reward collaboration.

Built it around that. AI-facilitated gaming experiences teams can jump into when they want, not when HR schedules it. Play on their terms. Grow through actual collaboration, not simulated trust exercises.

30% boost in collaboration in 90 days. Turns out, when you stop forcing fun, people actually have it.

Still my company. Still learning if I'm right.

THE DOLPHIN

CLIENT: Regional university

SHADOWS:
Internal, Perception, Market

What they thought:
People don't understand the breadth and depth of our programs or student opportunities. If they did, they'd choose us over others.

What was true: People thought of them as a backup, not a top choice. Tough to admit.

Regional public university. Safety school. Students applied when they didn't get in anywhere else.

Small class sizes, great professors, beautiful campus. But the reputation was stubborn. Recent rebrand didn't move the needle and internal surveys showed a stigma of shame.

I pitched: own it. Turn shame into pride. Their beloved mascot was a dolphin, so make the students dolphins too. Frame it as "you're a different kind of intelligent". Brilliant, but don't test well in traditional systems. Reframe "safety school" as "school for people who don't fit the box."

Put together some creative that I'm quite proud of—CGI dolphins being the first in their family to go to school, getting hired to work at Google ("Did you hear Google hired a Dolphin?"), showing up in a school counselor's office and doing the blowhole thing.

Some stakeholders loved it. The more risk-averse tanked the score so hard it killed the proposal. Consensus won out, picked safe bet firm. 18 months later their website hasn't changed a bit. Hm.

Learning moment for me. I am not for committees.

But I would have bet my fee that it would have worked. So, that's what I do these days.