I'm Proud of CloudSee Drive (Finally!)

LinkedIn co-founder Reid Hoffman famously said, "If you're not embarrassed by the first version of your product, you took too long to ship." I'm a perfectionist by nature, so this was always difficult for me to embrace in my software career. Combine perfectionism with impostor syndrome (which I've learned afflicts about 100% of people who work in software), and you have a potentially serious problem—you'll be slow to ship, which is the kiss of death in this field. 

But once I learned from the best engineers I've worked with that you have to ship, I mostly embraced Reid's idea. I actually fused that idea together with a related notion from one of my all-time favorite and most talented fellow developers: "Just because you're not paranoid, that doesn't mean someone is not out to get you." Or, paraphrase the great software developer Michael Jordan, "The great ones are always a little paranoid."

In short, stay paranoid, and that will keep quality high. And then ship constantly. 

Bringing this back to our flagship SaaS product, CloudSee Drive, the addressable market for it is orders of magnitude larger than any market we had targeted in the past. And we were dealing with immense complexity. It's an S3 management tool (Amazon's oldest cloud system, for storing...everything). Estimates are that there are multiple zettabytes of data in S3. (I'll wait while you look up how large that is; I had to look it up too.) In other words, lots of problems to solve. Hard problems. 

As we built, we then faced the inevitable pushback from potential customers—"It doesn't do X." "I need it to do Y." But we're really good at roadmapping a product, so we prioritized the good feedback, and kept building. A big, year-long push starting in late 2024 resulted in an objectively impressive feature set—enterprise-grade security (always priority 0 for us), a parallel processing engine to handle massive scale (ever try to search for something amongst 500 million files?), really elegant organizing features (best damn tag management interface you've ever seen!), the ability to "talk to your files" (a natural language search feature), yet more enterprise-grade security layered on, and even the ability to connect your favorite AI to our product (because, duh). 

All this from a small-but-mighty team (11 people total delivered all that), inside a bootstrapped company, and all done while still juggling other priorities (our attempted services-to-SaaS conversion). 

I'm really proud of what we built. And maybe it'll even sell. That's a different topic. I've read countless obituaries of even really great tech that didn't sell, for a variety of reasons. (Most recent obit I read was the documentary "General Magic," about the tech innovations that preceded the smartphone revolution; and "failed" miserably. Check it out if you haven't yet.) Bottom line (pun), building and selling are two separate-but-related things, and they don't always go together. I'm (finally!) proud of what we built. It's excellent software and systems.

I'm Sigmund. Thanks for listening.