Dave Kellogg

Dave Kellogg

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Operator/advisor, former CEO/CFO, blogs on SaaS metrics, strategic planning and finance leadership

Silicon Valley Startup Interests Still Misaligned After 15 Years
SocialApr 15, 2026

Silicon Valley Startup Interests Still Misaligned After 15 Years

This post is 15 years old and still true as ever today. Interest Misalignments in Silicon Valley Startups https://t.co/DuSUTOvMRn

By Dave Kellogg
Exploring the Mythical Engineering Productivity Metric Webinar
SocialApr 14, 2026

Exploring the Mythical Engineering Productivity Metric Webinar

Please join Dan Teodosiu and me next week for a webinar that explores the search for the mythical engineering productivity metric. Bringing together a former CEO/CMO and CTO to discuss this topic only serves to make it more fun. See you there...

By Dave Kellogg
WordPress “Downgrade” Button Launches Support Chat, Not Downgrade
SocialApr 13, 2026

WordPress “Downgrade” Button Launches Support Chat, Not Downgrade

Clicking "downgrade" on Wordpress doesn't downgrade you but starts a chat with a "happiness engineer." https://t.co/FgT3H7VaaL

By Dave Kellogg
Corporate AI Mirrors Great Leap Forward’s Flawed Ambitions
SocialApr 11, 2026

Corporate AI Mirrors Great Leap Forward’s Flawed Ambitions

Superb piece that likens corporate AI adoption to The Great Leap Forward in China from 1958 to 1962. Find out what agronomic pseudoscience, bad metrics and reporting, and sparrow killing have in common with AI inside corporations. The AI Great...

By Dave Kellogg
Future Generations Will Judge Us for Warming Earth
SocialApr 10, 2026

Future Generations Will Judge Us for Warming Earth

I wonder how future generations will feel about us warming the planet to do this https://t.co/Ir5ehRW3Pv

By Dave Kellogg
From Seat Licenses to Outcome‑Driven Software Execution
SocialApr 8, 2026

From Seat Licenses to Outcome‑Driven Software Execution

Enjoyed Devin Mathews’ “ghost of software” piece — thoughtful, provocative, and directionally right. Devin’s a strong writer and keen observer, and I especially like how he bridges operator and financial perspectives. The shift from seat-based software to outcome-driven execution is...

By Dave Kellogg
OpenAI Nears $1 Trillion Mark Among Elite Titans
SocialApr 3, 2026

OpenAI Nears $1 Trillion Mark Among Elite Titans

Felt like a good day to remind ourselves that there 12 public companies with a market cap >$1T and are here are some high-level financials on them. With today's announcement, OpenAI is worth ~$0.9T. (Data from Gemini.) https://t.co/44feWVSf4X

By Dave Kellogg
Prioritize Effectiveness First, Optimize Efficiency Later
SocialMar 31, 2026

Prioritize Effectiveness First, Optimize Efficiency Later

First, be effective. Then be efficient. A lot of startup founders worry about the second before the first. If you're a well-funded startup, be effective first. We can always optimize for efficiency later. But Lord help you if you...

By Dave Kellogg
Use AI for Drafts, but Own the Final Output
SocialMar 29, 2026

Use AI for Drafts, but Own the Final Output

There’s a question I’ve been mulling for a while now, and I think it’s time to write it down: when is it okay to use generative AI in a given business context, and when does it cross a line? I’ll...

By Dave Kellogg
True Power Lies in Mastering One's Own Mind
SocialMar 28, 2026

True Power Lies in Mastering One's Own Mind

On introspection. Confucius: “He who conquers himself is the mightiest warrior.” Augustine: “Return to yourself. In the inner man dwells truth.” Descartes: “I think, therefore I am.” A9: "Nah" https://t.co/2yXmR340OH

By Dave Kellogg
VT100 Debuted 1978; VAX 11/780 Defined 80s Computing
SocialMar 27, 2026

VT100 Debuted 1978; VAX 11/780 Defined 80s Computing

The VT100 came out in 1978 but I get your point on CLIs. (VAX 11/780 was the computer for the 80s in 1978.)

By Dave Kellogg
Read This Acquisition Guide Early to Avoid Heartache
SocialMar 25, 2026

Read This Acquisition Guide Early to Avoid Heartache

This book has a few too many TLAs (three letter acronyms) but it also contains valuable street wisdom in thinking about selling your company. Read it now, years before you want to sell, and save yourself time and heartache. Magic...

By Dave Kellogg
Executive Bonuses Should Reward Revenue, Not Stock Hype
SocialMar 25, 2026

Executive Bonuses Should Reward Revenue, Not Stock Hype

I get why companies do it, but ... me no like incenting executives on stock price / market cap as opposed to operating metrics like revenue and profit. They can miss their target and multiples expand enough the bonus stil pays....

By Dave Kellogg
Treasury Declares U.S. Insolvent, Media Overlooks Crisis
SocialMar 24, 2026

Treasury Declares U.S. Insolvent, Media Overlooks Crisis

Do what you do best. The Treasury just declared the U.S. insolvent. The media missed it https://t.co/8cCbpiK9a8

By Dave Kellogg