Clouded Judgement

APRIL 11, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The Bond Market - Crisis Averted? April has been WILD. 8 trading days in, and we’ve had moves of +12%, -6%, -5% and -4% in the Nasdaq. The couple days that were in the +/- 1% range felt “normal” even though historically those would be somewhat large moves for an overall index.

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Clouded Judgement

APRIL 9, 2025

Q4 earnings season for cloud businesses is now behind us. The 60 companies that I’ll discuss here (which is not an exhaustive list, but is still comprehensive) all reported quarterly earnings sometime between January 29th – April 1st. In this post, I’ll take a data-driven approach in evaluating the overall group’s performance, and highlight individual standouts along the way.

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Clouded Judgement

APRIL 4, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Economic Uncertainty The big news this week was Tariff day! It sure caused a reaction in the markets on Thursday… At the end of day Thursday, the median software NTM revenue multiple was 4.8x. Going back 10 years, we’ve only hit that level twice.

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Clouded Judgement

MARCH 28, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The New AI Risk Curve: Why AI Startups Grow Faster—and Fade Faster One thing I’ve been thinking a lot about recently (and having conversations with other investors about frequently) is the juxtaposition of: AI companies growing faster than companies from prior cycles AI companies will have more “false starts” than companies from prior cycl

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Clouded Judgement

MARCH 21, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now M&A is Back! We’ve seen a ton of M&A in the first quarter of the year. Will the floodgates open? Probably depends on whether the deals make it through regulatory approval. If they do, I expect a lot more M&A activity to follow.

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Clouded Judgement

MARCH 14, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Authentication in the Age of AI Agents I've been reflecting lately on how AI agents might evolve and how they’ll be built. Specifically, I'm interested in the distinctions between web-based and desktop-based AI agents.

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Clouded Judgement

MARCH 7, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Continued Uncertainty Last week I wrote about the period of max uncertainty we’re in - particularly the political and economic uncertainty (and how they’re related). This week, we saw an economic forecast predict Q1 GDP to shrink nearly 3%.

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Clouded Judgement

FEBRUARY 28, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Max Uncertainty We seem to be entering a “risk off” market. There are a number of factors adding to the uncertainty, but the three biggest in my opinion (that also happen to be related) are: Political: What is Trump going to do with tariffs & what are the impacts of DOGE and pulling out that much government spend in the time frame they’re di

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Cloud Government Technical Review Software Review 144

Clouded Judgement

FEBRUARY 21, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The Platform Evolution Cycle I think we’re entering a really interesting point in the AI platform shift. When I think back to other platform shifts (like the internet or cloud) I think they all followed a similar trajectory of stages: Basic infra, which led to: Basic applications, which led to: Complex infra (as we realized where the gaps were), which led t

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Clouded Judgement

FEBRUARY 14, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Software Earnings Kick Off Software earnings season is in full swing, and so far the results have been uninspiring… Q4 earnings are great because companies for the first time guide for the next full year (and then every quarter they update the full year guidance).

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Clouded Judgement

FEBRUARY 7, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now “Grouping + AI” for Triage One area I’m quite excited to see AI revolutionize is “grouping + triage” workflows. There are so many of these workflows out there today, and many of them are quite manual.

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Clouded Judgement

JANUARY 31, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The Winner of Cheap AI - The Application Layer There’s been a lot of talk recently about how 2025 is “the year AI applications take off.” I agree with this sentiment - and wanted to talk about one reason why.

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Clouded Judgement

JANUARY 28, 2025

What a last few days in AI land! DeepSeek came out with R1 and it created huge ripple effects in the tech world, maybe culminating with the DeepSeek app shooting up to #1 in the app store (is this real? The result of bot farms downloading in mass?). What is DeepSeek? DeepSeek is an AI company that focuses on distilling large, complex AI models into smaller, more efficient versions (while also adding in their own research breakthroughs).

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Clouded Judgement

JANUARY 24, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The Year of “Enterprise AI” One of the biggest challenges facing AI systems in enterprises today is the “last mile” problem: how do you make AI both reliable and accurate for specific enterprise use cases?

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Clouded Judgement

JANUARY 17, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now December Inflation There are periods of time where the market is more driven by macro factors, and other times where it’s less influenced by macro factors. Presently, it feels like the market is waiting on pins and needles for incremental macro data points.

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Clouded Judgement

JANUARY 10, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Rising Rates The 10Y is up to 4.7%. When the Fed started cutting the fed funds rate in September ‘24, the 10Y was at 3.7%. So while the Fed is cutting rates, the 10Y is rising! This might seem odd at first, but there are some pretty clear reasons why this is happening.

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Clouded Judgement

JANUARY 3, 2025

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The Rise of Domain-Specific Models in 2025 It’s prediction season! Here’s mine: 2025 is shaping up to be the year that domain-specific AI models take center stage. While 2024 celebrated the triumph of generalized models OpenAI, Anthropic, Meta and others trained on vast public datasets, this year’s breakthroughs are emerging from a different sou

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Clouded Judgement

DECEMBER 27, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now 2024 Top Performers This year the median software multiple ended at 6.1x. At the start of the year it was 6.3x. Throughout the entire year there was very little multiple expansion or contraction. This year there were 3 cloud software companies that traded up >100%!

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Clouded Judgement

DECEMBER 20, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now The Fed Bomb The markets were enjoying a nice little Santa Claus rally until this Wednesday when the Fed decided to shake things up! The Nasdaq dropped >3.5%, which I believe is the largest drop after a fed meeting going back to the onset of Covid.

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Clouded Judgement

DECEMBER 13, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Beat and No Raise? We’re just about through 2024. It’s always fun to look back at consensus estimates at the start of the year (for full year 2024 estimates) and compare to consensus estimates today for 2024.

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Clouded Judgement

NOVEMBER 29, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Software Rotation? Quick update this week - happy Thanksgiving everyone! Last week I wrote about what could be the start of a rotation into software (software was up, and big tech / mag7 was underperforming). Where are we one week later?

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Clouded Judgement

NOVEMBER 22, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Is Software Back? One reason I really like writing this blog is it gives me the opportunity to go back in time and revisit how I was thinking about the world at certain points in time. In many ways it acts as a personal journal.

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Clouded Judgement

NOVEMBER 18, 2024

Today ServiceTitan filed their initial S1 statement. A S-1 is a document companies file with the SEC in preparation for listing their shares on an exchange like the NYSE or NASDAQ. The document contains a plethora of information on the company including a general overview, up to date financials, risk factors to the business, cap table highlights and much more.

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Clouded Judgement

NOVEMBER 15, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now A Shift To Growth? I think the market and companies are starting to shift focus towards growth. Over the last 2 years there has been a big shift in how software companies value growth vs profitability. Growth was the sole focus in the ZIRP period, and as we came out of that period there was a renewed focus on profitability.

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Clouded Judgement

NOVEMBER 8, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Fed Update This week the Fed cut rates by 25 bps. The target rate now sits at 4.5% - 4.75%. Powell also gave some remarks which I summarized below: Economic Outlook : The economy remains strong, with solid GDP growth at 2.8% in Q3, resilient consumer spending, and strengthening investment.

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Clouded Judgement

NOVEMBER 1, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Rates Update The 10Y has jumped from 3.7% at the start of October to 4.3% today. A ~15% move up in a month! Robust jobs / unemployment / broader positive economic data caused investors to reassess their expectations for future Fed actions.

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Clouded Judgement

OCTOBER 25, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Misaligned Incentives In the venture capital world, there are largely 3 constituents: The GPs (investors), the LPs (pension funds, endowments, universities, family offices, sovereign wealth funds, etc who give money to GPs), and founders (portfolio companies).

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Cloud Venture Capital Investment Revenue 358

Clouded Judgement

OCTOBER 18, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Systems of Record » Systems of Intelligence There’s a long-held belief in enterprise software that building a lasting moat requires a system of record. Salesforce is the system of record for customer data, Workday for employee data, and ServiceNow for IT data, to name a few.

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Cloud AI Enterprise Forecasting 300

Clouded Judgement

OCTOBER 11, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Budget Flush Coming? Something that has been on my mind recently - will we see a larger than normal budget flush at the end of this year? First - what is a budget flush? A budget flush occurs when companies rush to spend remaining budgeted funds before the fiscal year ends, often due to a "use it or lose it" mentality.

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Clouded Judgement

OCTOBER 4, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Voice: The Next Computing Paradigm OpenAI released some pretty cool features over the last two weeks. The first was pushing advanced voice mode to everyone. The second was announcing their speech-to-speech Realtime API.

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Clouded Judgement

OCTOBER 3, 2024

Q2 earnings season for cloud businesses is now behind us. The 62 companies that I’ll discuss here (which is not an exhaustive list, but is still comprehensive) all reported quarterly earnings sometime between July 24th – September 9th. In this post, I’ll take a data-driven approach in evaluating the overall group’s performance, and highlight individual standouts along the way.

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Clouded Judgement

SEPTEMBER 27, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Foundation Models Are to AI what S3 was to the Public Cloud Many people look at 2006 as the birth of the public cloud - the year Amazon launched AWS. Microsoft launched Azure in 2010, and Google launched GCP to the public in 2011 (they launched a preview of Google App Engine in 2008, but made it publicly available in 2011).

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Clouded Judgement

SEPTEMBER 20, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Rate Cut! It finally happened! The Fed cut rates by 50bps. This represents the first rate cut since the start of the Covid pandemic, and one that has been highly anticipated. There was a little debate on if this cut would be 25bps or 50bps, but we ended up with 50bps.

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Clouded Judgement

SEPTEMBER 13, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now 2024 Estimates Q2 earnings season is now behind us. I’ll provide a more comprehensive recap later, but for now, let’s look at how the future outlook has changed after Q2 earnings. One metric I like to examine is how much companies adjust their full-year guidance.

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Clouded Judgement

SEPTEMBER 6, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Kingmaking in the Era of AI When too many kings vie for the crown, you’re left with a brutal game of thrones. Can anyone truly win in a game of thrones? And will the end justify the means? I’ve been thinking about this a lot recently.

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Clouded Judgement

AUGUST 30, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Incrementalism vs Transformative Leaps Over the last 5-10 years, software markets have become increasingly crowded. Simultaneously, venture markets have expanded dramatically, contributing to this overcrowding. In a world without venture capital (or other sources of external financing for startups), each company would have to grow solely based on the merits of th

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Clouded Judgement

AUGUST 23, 2024

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Don’t Wait Two weeks ago I wrote about the growing number of private zombies. A common question I got after that post was “what should I do if I’m in that position?” A couple thoughts below. Most importantly - don’t wait.

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