It's hard to strike gold twice

Not because founders get worse, but because building a novel business that truly works is very hard.

• Naval Ravikant - Airchat
• David Sacks - Glue AI
• Adam Neuman - Flowcarbon 
• Marissa mayer - Sunshine 
• Ev Williams - Mozi
• Kevin Rose and Alexis Ohanian - Digg relaunch
• Kevin Systrom - Artifact 

Not a dunk.

Just an observation, a pattern worth noticing, and a reminder that yea, it's hard even if you've succeeded in the past.

On Perplexity - Timeline and Hypotheses [Updated]

I continue to update the timeline as news comes out. The last update was made as of April 23, 2025. I'm not editing other content.

Check out my tracker spreadsheet here: Perplexity Table

~~~

Perplexity baffles me! 

It’s a fast-growing startup that has built a great product and is stirring competitive reactions from the likes of Google and OpenAI.

At the same time, it's sustainable competitive advantage is unclear, and it's saddled with growth expectations attached to a $3B valuation (maybe $9B). 

To help wrap my had around Perplexity, I created a running 2 year timeline to understand where they've been and help me think through where they might be going.

Read on for a fully sourced timeline of Perplexity's rise, covering:

• Fundraising
• Product Launches
• MAUs
• Revenue 
• Legal action
• and more

Cheap, Non-Technical and "Building": How to Start Vibe Coding

Last weekend I started vibe coding with Lovable and it was a blast!

Picture this:

• I'm at my computer prompting away, having fun learning how to use the Gemini API, GitHub, and Supabase
• Woo hoo! I'm just chit chatting with the AI agent, we're building (I think?)
• Then reality hits: 94/100 messages gone

I had a decision: should I pay to upgrade to Lovable's $50/month plan to get 250 messages? Hard pass.

I'm non-technical and cheap 💁‍♂️ I'd burn through that tier creating a mediocre MVP and face a $200 bill.

What’s a scrappy, low-budget "builder" to do?

TLDR;

• Assemble your AI "team" using free/cheap tools
• Use ChatGPT/Claude + a notes app to map the path
• FAFO across free tiers - pay only when you get it
• Embrace the deep pain of debugging  

My Perspective on the Chief of Staff Role

Check it out on a much prettier version on this Notion page

⚡️ A great Chief of Staff (Cos) is a high-EQ, operationally excellent, and strategic leader who helps move the entire organization forward every day. 

Read more below.

No, GenAI isn't Killing SaaS

I thought the internet moved past the "SaaS is dead" takes months ago. Apparently not! 

"SaaS is dead" generates engagement and points to real shifts happening in tech, but at this point it's stale and it's always been wrong.

Here’s why the arguments for “SaaS is dead” don’t hold up:

• The argument is so broad as to be (almost) useless
• The argument is internally inconsistent 
• Sufficiently valuable software is very complex
• Comparative Advantage Still Matters
• GenAI ➡️ More Software ➡️ More SaaS, Not Less
• SaaS Companies Are Riding the Wave
• Performant AI Agents Are Neither Simple nor Isolated

Think "SaaS + AI" not "SaaS vs. AI."

Excellent questions for coaching team members

Questions via: The Leaders Cheat Code by Rachel Pacheco

I categorized them based on how I'd user them.

How I'm Using GenAI Today @ Work

Debugging with Jam.dev -- super great tool for capturing and communicating bugs, has some AI features built in with more on the way.

Content generation -- I created a Claude Project and uploaded examples of content + our content guidelines. Now, when I need something created, I just prompt it, get the ~80% done rough draft, and edit it quickly for accuracy + tone.

Strategy thought partner -- I created a Custom GPT and gave it instructions describing the startup I work for and sometimes use it as a thought partner on how it'd approach problems.

Research - I'm playing with Gemini Advanced to do initial research using the Deep Research feature. 

Meeting AI -- I have Granola downloaded, but I find it basically useless. I like paying attention in meetings and taking notes.

Exploring

• Guru / Dustt -- I'm exploring implementing one of this GenAI integrated tools to make work information more easily accessible
• Delphi -- we're testing this out as a way to get a GenAI chatbot grounded in custom data before we invest in using OpenAI API's or the like.
• Spur -- looking at this to help with QA, have not implemented yet

6 Years of Remote Work: Lessons Learned

I started working “remotely” at Mighty in 2018, though it wasn’t exactly by design. 

At the time, Mighty was a small startup tucked into the corner of a two-floor office shared with a larger company.

I make the most impact when I'm able to do deep, focused work, so to get some uninterrupted time, I’d grab my laptop, monitor, mouse, and headphones and march to a quiet, under-construction corner of the building. 

It wasn’t glamorous, but it worked! In hindsight, it was my first taste of “remote” work.

Fast forward six years, and I’ve since worked in both hybrid and fully remote roles. 

What I’ve learned along the way is that the principles for excelling at remote work are strikingly similar to what makes someone effective in an in-person setting. 

It’s all about clarity, communication, and intentionality.

Read on for the habits and principles that have helped me excel while working remotely 👇

On Jam.dev - Strategic Analysis

 

Jam.dev builds a browser extension that helps teams resolve bugs faster. It's cool, effective, and incredibly user-friendly!

I got a bit obsessed about understanding the business and here we are -  a strategic analysis of Jam.dev for fun. Read on for my take on:

• Adoption
• Product Overview
• Growth/Pricing
• Strengths
• Challenges
• Strategic path forward

As always, I’m certain to be missing loads of information and context, and would love to hear why I'm wrong. May this be useful to someone, in some fashion, no matter how small 🫡

Legal AI Is a Crowded Market

These are companies that just happened to flow through my inbox in the last 24 hours, no proactive searching 

• robinai.com 
• finchlegal.com 
• spellbook.legal 
• draftwise.com
• https://www.supio.com/
• https://www.paxton.ai/

And then there are the bigger players, like 

• ironcladapp.com 
• harvey.ai 
• evenuplaw.com

I haven't used these products, but I have a hard time thinking the value they produce is differentiated. 

Seems like a race to the bottom and war of CAC, which favors established players who can distribute Gen AI features through existing implementations (i.e. ironclad, steno, clio, and so on)