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  1. AI Native Loops

    Engineers solved this problem twenty years ago.

  2. There’s a photo of Michael Jordan from 1994, sitting in a White Sox dugout in full uniform, looking like he isn’t quite sure he belongs there.

  3. Plagiarism

    Every generation of cheap content invents its own watermark.

  4. Two Loops

    I spent the last few days building using some of the latest AI tools and models.

  5. Double Down on Humans

    Was catching up with a founder of an early stage software company last week over coffee.

  6. Anthropic Whales

    The insights, analysis, and data presented in this article are for informational and educational purposes only and do not constitute financial, investment, legal, or tax advice.

  7. Builders or Growers

    There is an iconic scene in Moneyball where Billy Beane sits at a drab boardroom table, completely surrounded by old-school baseball scouts.

  8. The New Exec Team

    There is a scene in Jaws where the shark finally shows itself, and Brody famously says, “You’re gonna need a bigger boat.”

  9. The Legacy SaaS Premium

    Over the last six months, I’ve spoken to more than a dozen executives at mature, established software companies.

  10. The Last Castle

    I have spent the last twenty years of my life in the SaaS trenches.

  11. Bottlenecks

    Software used to be hard.

  12. Bronze Medals

    We were halfway to San Antonio yesterday when I realized I had not looked at a single Yelp review or scrolled through a TripAdvisor list.

  13. The End of Management

    I have managed hundreds of people over my career.

  14. Chasing Approval

    It is a survival mechanism.

  15. Most leaders are still stuck in a linear mindset.

  16. Most leaders confuse activity with progress.

  17. I have spent fifteen years in the trenches of high growth SaaS.

  18. Reflections on 2025

    It is good to be back sharing my thoughts more.

  19. Private equity likes to call itself the rational antidote to sentimental founders, bloated corporate structures, and quarterly-obsessed public markets.

  20. Early Stage Startup DNA

    I’ve thought a lot lately about my past time in startups earlier in my career.

  21. Power Dynamics

    I was once in a meeting a Superpages.com early on in my career.

  22. The End of Entry Level

    The first startup I ever invested in ran out of money not because the product was bad, but because the founders thought scale meant hiring.

  23. Headless CRMs

    I’ve been in SaaS for over two decades.

  24. I’ve had some intense conversations lately—friends who run VC firms, founders building on the frontier of AI, and business owners seeing the shift in real-time.

  25. The Mirage Age

    In the swiftly evolving landscape of artificial intelligence (AI), we find ourselves living in what I call “The Mirage Age.”

  26. Toxic Assets

    In 2008, the world witnessed a financial crisis of unprecedented scale, largely precipitated by the collapse of the housing market.

  27. The Great Reset

    I was having lunch with a friend last week who leads HR at a Fortune 500 company.

  28. The Covid pandemic forced the majority of the global workforce to abandon their traditional office space.

  29. The last few years has been one of the most challenging events of our time.

  30. The Illusion of Output

    We are in the midst of the one of the most fascinating shifts in modern labor.

  31. “My goal is to be the CEO one day.”

  32. Kevin Maye

    100 days on the job.

  33. Why I Quit LinkedIn

    After 10 years of the hustle and grind, you can say I had “made it.”

  34. Stewart, I’ve been your #1 fan since day one.

  35. The year 2020 will forever be remembered as a year of change in business.

  36. Law School and Learning

    There was a time when law school was my future.

  37. Big Auto vs. Tesla

    9 years.

  38. Slack’s S-1 Filing

    Slack released their S-1 today, and as usual with SaaS companies I took time to read through it.

  39. I live in the future.

  40. Just an interesting note from my project Facebook fan page this morning.

  41. What is the Zero Moment of Truth?

  42. Often I hear website owners paranoid about what people post on their site.

  43. There are tons of absolutely broke dreamers out there, and hopefully I’ve moved in the right direction over the years.

  44. I used to advertise on facebook quite regularly.

  45. Some would call SMS marketing the most effective marketing channel ever invented.

  46. I remember going to work with my dad growing up.

  47. Experian Hitwise released a recent study touting that 1 Facebook fan = 20 extra visits to your website.

  48. Today I was able to attend the Hoth‘s webinar about SEO link building.

  49. If there was an SEO anonymous support group I’d introduce myself like this.

  50. I’m fascinated with algorithms and equations.