I’m writing this from my apartment on December 28th and I genuinely can’t tell you what month it’s without checking. That’s 2020 in one sentence.
A year ago I was heads-down building Decloud, convinced that the biggest challenge ahead was product-market fit. Then March happened and the biggest challenge became making sure the company didn’t die. Different skill set entirely.
Decloud Made It
I’ll start with the thing I’m most proud of. Decloud survived 2020. Not just survived – grew. But I want to be honest about what that actually looked like, because the LinkedIn version of startup survival stories is always cleaner than reality.
March and April were ugly. Two potential customers froze their budgets overnight. A partnership we’d been working on for months went silent. I spent a few weeks genuinely unsure if we’d make it to summer. The thing that saved us was that our product was a cloud infrastructure tool during the exact moment when every company on earth suddenly needed better cloud infrastructure. Lucky timing dressed up as strategy.
By Q3 we had more inbound than we could handle. We hired. We shipped features faster than I was comfortable with. Some of that code is going to haunt me in 2021 and I know it. But the company is alive and growing, and if you’d told me that in April I would have hugged you.
Enterprise Work
The other big change this year: I started taking on enterprise engineering work. This wasn’t planned. A former colleague at a large financial services company called me in June, panicking about their cloud migration timeline. COVID had compressed their three-year plan into six months and their team was drowning.
I said yes mostly because I wanted to help. Then another call came. Then another.
By the end of the year I’d worked with a handful of enterprises on cloud architecture and infrastructure strategy. It taught me things I couldn’t have learned any other way.
The biggest lesson: large organizations don’t fail at technology. They fail at decision-making. I watched a team of perfectly competent engineers sit paralyzed for three weeks because nobody could get sign-off on a Kubernetes cluster configuration. The technology was the easy part. Getting six stakeholders to agree on a risk tolerance was the hard part.
I also learned that my Decloud experience translated directly. The problems startups solve with speed and scrappiness are the same problems enterprises solve with process and budget. Same problems, different constraints. Understanding both sides made me better at each.
Remote Work: What the Industry Got Wrong
I need to rant about this because the discourse around remote work in 2020 was insufferable.
Half the industry spent the year writing thought pieces about how remote work is the future and offices are dead. The other half spent it writing thought pieces about how remote work is destroying culture and we need to get back to the office immediately. Both camps were wrong in the same way: they treated remote work as a binary instead of a design problem.
Remote work is infrastructure. It’s not a perk, it’s not a philosophy, it’s a set of systems and processes that either work or don’t. I’ve been running distributed teams since Dropbyke. It works when you design for it. It fails when you take your office habits and paste them onto Zoom.
The companies that struggled in 2020 weren’t struggling because remote work doesn’t work. They were struggling because they’d never invested in written communication, async decision-making, or documentation. They replaced hallway conversations with eight hours of video calls and then blamed the format.
At Decloud we went fully remote and our velocity actually increased. Not because remote is magic. Because we were already async-first. We already documented decisions. We already wrote things down instead of saying them in meetings. COVID just removed the commute.
The companies that will thrive in 2021 aren’t the ones that go back to the office or the ones that stay remote. They’re the ones that actually design their communication systems instead of defaulting to whatever they did before.
What I Got Wrong
I try to be honest about this in these posts, so here goes.
I underestimated how much the pandemic would affect my team’s mental health, including mine. I spent Q2 optimizing for output when I should have been optimizing for sustainability. We shipped a lot but a couple of people burned out and that’s on me. I should have noticed sooner.
I also overestimated how quickly enterprises would modernize. The work showed me that compressed timelines don’t mean compressed politics. Some organizations moved their infrastructure to the cloud in weeks but took months to update their security policies to match. The gap between technical capability and organizational readiness is wider than I thought.
The SolarWinds Wake-Up Call
I can’t write a 2020 review without mentioning SolarWinds. In December we learned that a major software supply chain had been compromised for months. Government agencies, Fortune 500 companies, the works.
This is the kind of thing I’ve been warning about for years. Your security is only as good as your weakest vendor. Most organizations treat vendor risk as a compliance checkbox. SolarWinds proved it’s an operational reality. I expect this to dominate security conversations well into 2021.
What I’m Carrying Into 2021
Decloud has momentum. The work keeps growing. I have a clearer picture of how enterprises and startups can learn from each other. Specifically:
I want to build better. The code we shipped under pressure in 2020 needs attention. Technical debt is a loan and the interest is compounding.
I want to write more. This blog has been neglected. Part of it was time, part of it was that 2020 made everything feel too heavy to write about casually. But I think writing forces clarity and I need more of that.
I want to rest more. I did a bad job of this in 2020. I know the math: unsustainable output now means reduced capacity later. I know this intellectually. Doing it’s harder.
2020 was the strangest year of my career. It broke every plan I had and replaced them with better ones. I wouldn’t want to do it again. But I’m grateful for what it taught me, and I’m heading into 2021 with more conviction than I’ve had in years.
Onwards.