Positioning, pricing, decision-making, and figuring out what to focus on when everything feels urgent.
We wanted a merchant live in two weeks. Their team wasn’t ready, so we built around them. They launched. It broke. Now we maintain that feature forever. Every shortcut we took to close faster became work we owned forever. The fix is patience.
I’ve been at zero. Put my own money in to cover payroll. So I know the mistake most founders make when they get there: they keep operating like nothing changed. When you’re broke, there’s only one question: does this put money in the bank this week?
Two weeks ago, I shared our 2026 plan. Six Canadian cities. Clear targets. The next day, an enterprise customer asked us to open seven American cities. Our CEO is in Denver right now. The goal doesn’t change. The path just got a lot more interesting.
Team members. Investors. Advisors. The Board. Everyone suggests ways to squeeze more from existing customers. Subscriptions. Surcharges. Box size fees. Every idea makes sense on a spreadsheet. We keep saying no. The discipline isn’t saying no once. It’s saying no every quarter when someone new brings the same idea with different math.
We spent $20K a month on marketing. Got 700 downloads. Ten deliveries. Seven customers. My cofounder wanted to kill it. I wanted data. Here’s how we structured the uncertainty instead of pretending we knew the answer.
When you’re trying to double revenue, every initiative looks promising. You can chase 50 different opportunities and convince yourself they all make sense. You’ll waste months testing marginal improvements while your core business stays mediocre
There are two business types: one you control and one that controls you. A co-founder who survived the pandemic and thrived by managing conservative cashflow and growing from profit shares insights. Unlike many overly reliant on investments, he prioritized sustainable, self-sufficient growth, illustrating the essence of true business control.
How often do you say “yes” to customer requests?
“We need you to remove your product right away. It is hurting our business.”
It is every startup team’s hope — that they are building something that puts them in front of someone else that wants to buy their company.
Some of us have a hard time making decisions. Period. We like to analyze options until we’ve backed ourselves into a corner and all of them have expired.
This is a quick reminder of the simple principles that govern startup business life.
It nearly broke us.
We tried dynamic pricing. It made perfect sense on paper. Here’s why we killed it.
Why customers decide to buy from your company is not a mystery anymore.
The ultimate test of a founder is to take the red pill.
