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.

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

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)

On Perplexity - Timeline and Hypotheses

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 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

GenAI Litigation to Watch

Millette vs. Nvidia - https://www.404media.co/nvidia-sued-for-scraping-youtube-after-404-media-investigation/

UMG vs. Suno/Udio - https://www.theverge.com/2024/6/24/24184710/riaa-ai-lawsuit-suno-udio-copyright-umg-sony-warner

NyTimes vs. OpenAI - https://harvardlawreview.org/blog/2024/04/nyt-v-openai-the-timess-about-face/

Bartz vs. Anthropic - https://www.reuters.com/technology/artificial-intelligence/authors-sue-anthropic-copyright-infringement-over-ai-training-2024-08-20/

Dow Jones & New York Post vs. Perplexity - https://www.theverge.com/2024/10/21/24275924/news-corp-wall-street-journal-perplexity-lawsuit-copyright-infringement

You Get What You Click For

Algorithmic feeds are a mirror. 

For a remarkable number of folks, this reflection remains surprising, uncomfortable and frustrating.

Take Y Combinator partner David Lieb for just one case-in-point example. He recently shared his frustration with X/Twitter's algorithmic "ForYou" feed:

It’s largely clickbait videos and maga-Elon garbage.

The uncomfortable truth for David - and the rest of us - remains that algorithms across X/Twitter, Facebook, Threads, Reddit, TikTok, etc. don't pull content out of thin air. They respond to our behaviors, showing us more of what we engage with. 

The fact that David "For You" feed is populated with "fistfights and car crashes" (as mentioned in another tweet) suggests he has a habit of engaging with such content. If he truly found that content repulsive, he'd only use his "Following" feed.

Rather than get frustrated with the algorithms, you can bypass them with a click. However, that requires effort and awareness—two things often in short supply on these platforms.

In short, you get what you click for.

3 Good Recent Reads (Apple Vision, Choice Screens, AI)

9 Takeaways from the Vision Pro After 6 Months 

Matthew Ball

If one assigns 25% of this budget (5,000 of 20,000 patents) to the Vision Pro, the product has a price tag of $33 billion

‘Choice Screen’ Fever Dream: Enforcers' New Favorite Remedy Won’t Blunt Google’s Search Monopoly 

Megan Gray

...the EU Android choice screen has not changed Google’s market share.

Investing in the Age of Generative AI 

Kevin Zhang

SearchGPT's Example Results are Worse than Google

Only July 25th, 2024 OpenAI announced the SearchGPT prototype, and the twitter-sphere / threads-sphere reacted with "Search/Google is dead!"

I'm not so sure about that for a number of reasons, but OpenAI's own post demonstrates two

• "Designed to give you an answer" is big promise that may be hard to uphold
• Google is actually very good at producing useful results today

Read on 👇