Rob Woodbridge
Founder. Operator. Writing a book about what founders actually lose.
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Every Merchant We Rushed to Launch, We Launched Twice
We wanted a merchant live in two weeks. Their team wasn't ready, so we built around them. They launched. It broke. Now …
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You're Broke. Stop Acting Like You're Not.
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: …
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We Finished Our 2026 Plan Two Weeks Ago. It's Already Wrong. Here's Why That's Fine.
Two weeks ago, I shared our 2026 plan. Six Canadian cities. Clear targets. The next day, an enterprise customer asked us …
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Don't nickel and dime
Team members. Investors. Advisors. The Board. Everyone suggests ways to squeeze more from existing customers. …
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How Long to Stay Confused at Scale
We spent $20K a month on marketing. Got 700 downloads. Ten deliveries. Seven customers. My cofounder wanted to kill it. …
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Set the pace
A customer wanted us in six cities. So we opened six cities. Here's what a year of bleeding taught us about the …
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Fast Software: Build What You Need, When You Need It
Building custom software for your exact needs is now faster and cheaper than subscribing to platforms built for …
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10X Forces You to Stop Bullshitting Yourself
When you're trying to double revenue, every initiative looks promising. You can chase 50 different opportunities and …
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AI is just another layer, not the destination
AI isn't a destination but a service layer that will fade into the background of how business works.
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With AI it's the question, not the answer
With AI and operations, your answer will only be as good as your own experience.