How to audit your brand for hidden debt.

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Founders rarely build the brand they imagine. The market reshapes it.

Customers respond in ways you didn’t plan. Some bets hit, others die. That gap between what you thought you created and what actually exists is where hidden brand debt piles up.

Take Peloton. They imagined themselves as a premium lifestyle and community brand; the “Apple of fitness”. That was the story on paper. But what the market actually built was a connected exercise equipment company tied too tightly to a pandemic boom. When the gap widened, the liabilities showed: overproduction, confused positioning, and a story they couldn’t sustain once people left their homes. Their hidden brand debt caught up fast.

The way forward is an audit.

Start by mapping two lists:

1. What you think you’ve built: the story you tell investors, the vision deck, the “positioning slide.”

2. What you’ve actually built: the way customers describe you, what they buy from you, the reputation you can’t shake.

Now compare the two. Every mismatch is either an asset (a new advantage you didn’t plan for) or a liability (a drag you keep ignoring). The faster you name them, the faster you can stop burning spend on the wrong things and invest in the right ones.

Reflections to work through:

Where is your imagined brand out of sync with your actual one?

Which surprises from the market point to real leverage?

What “vision” are you forcing that the market keeps rejecting?

Would your audit show real equity, or just busywork spend? Let’s talk.

Busywork stalls founders. Delegation buys back focus.

→ Wing gives you the team to do it.

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The assistant that scales with you

Great leaders don’t run out of ideas. They run out of hours.

Wing gives you a dedicated assistant who plugs into your workflows – calendar, inbox, research, outreach, and ops – so execution never stalls. Wing can:

• Onboard in days, not months

• Run the day-to-day so you don’t have to

• Adapt as your business grows

With Wing, you buy back time without adding headcount. More focus for strategy, more follow-through on priorities, and a lot fewer “forgot to send” moments.

Work smarter with Wing

Ian Adams, Founder the little red sofa

Before founding the little red sofa, I led strategy and creative for brands like Jeep, HSBC, and Unilever at top global agencies and in-house teams across 8 countries. Now I work with founders to turn brand clarity into sustainable growth.