Twenty-five years of expensive lessons.
None of these came from a course. Each one cost me money, time or sleep in a business I actually owned — Boardsox, the raw food business, the wetsuit brands. I write them down because the founders I work with are usually about to make the same call.
Nobody was coming to save the business
Two years in I was still waiting for the thing that would make it work — the viral post, the stockist, the agency who’d finally crack the ads. None of it arrived. The business turned the quarter I stopped waiting and started making one decision a week that I could measure.
What it cost me: Cost me two years of standing still.
Cheap traffic is the most expensive thing you can buy
It looks like growth on the dashboard and eats your margin in the warehouse. I’ve run months where sales were up 40% and the bank account went backwards. Now the first question is always what the customer is worth over a year, not what the click costs today.
What it cost me: Cost me a summer of profitless revenue.
Range is a cost, not a competitive advantage
I convinced myself variety was a reason to buy from us. It was really a reason for customers to freeze and for me to hold stock nobody wanted. We cut the Boardsox range and revenue per visitor went up. Every client catalogue I look at now, I look at first.
What it cost me: Cost me a full year of margin.
You already own your next quarter of revenue
Everyone wants to talk about acquisition. The customers who bought from you last year are cheaper, warmer and more profitable, and most brands do almost nothing with them. Email is the least glamorous and highest return work in ecommerce.
What it cost me: The mistake I fixed fastest, and regret least.
If you can’t explain it on a Monday, it won’t scale
Every system that survived in my businesses was one I could describe to a new team member in ten minutes. The clever ones — the spreadsheets only I understood, the process living in my head — all died the moment I got busy.
What it cost me: Cost me three good hires who left frustrated.
Price is a decision, not a discovery
I underpriced for years because I was scared of hearing no. When I finally raised prices the customers who left were the ones costing me the most to serve. Nobody has ever told me they left because a product was too good.
What it cost me: Cost me more than every other mistake combined.
Your website is a salesperson, not a brochure
For years I judged mine on how it looked. It should be judged on what it answers. The single biggest jump Boardsox ever had came from putting sizing information above the beautiful photography — which felt like a downgrade and sold considerably better.
What it cost me: Cost me every visitor who left with a question.
Cash and profit are different things, and cash wins
I have been profitable and nearly unable to pay a supplier in the same month. Containers, terms and stock cycles will kill a growing business faster than a bad quarter. Learn to read cash before you learn to read attribution.
What it cost me: Cost me two sleepless Christmases.
Advice from people who haven’t done it is entertainment
The most expensive tactics I ever bought came from people who’d never carried the stock, worn the refund or made the payroll. Ask anyone advising you what they’ve personally built and what it cost them. If they can’t answer, you’re paying for theory.
What it cost me: Cost me around $60,000 in courses and retainers.
The best hire is the job you no longer need done
My instinct was always to hire for the mess. Fixing the process first usually meant the role changed shape or disappeared. Systems before people — the businesses I see struggling most are the ones that hired their way around a broken process.
What it cost me: Cost me a year of the wrong salaries.
Experience is only useful if it transfers.
I can’t give you back the two years I spent waiting for something to happen. What I can do is tell you what it looked like from the inside, so you recognise it faster than I did.
If one of these is describing your business right now, that’s the conversation worth having. Bring it to a call.
-
Written from the P&L
Every lesson here has a number attached to it in a business I owned. That’s the only kind of advice worth paying for.
-
Not a framework
There’s no acronym and no five-step system. Businesses aren’t that tidy and neither is the learning.
-
Still being added to
I’m still running three brands, so the list keeps growing. That’s the point of working with an operator instead of a coach.
-
Yours to use
Take any of it. If it saves you one of the mistakes on this page, it’s done its job.
Clients I've grown.
