Back to San Francisco, and a few other things.

August 25, 2025 update: Back in SF, new blog post, looking for the Latino Dave Ramsey, and more.

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New Blog: What Are You Optimizing For?

It takes a few years to develop any real competence in a specific domain. This is particularly true in our professional lives. In our careers, we seek to acquire a particular competence because we believe that the acquisition of said competition will lead to upward mobility and more money.

The issue, however, is that we live in a dynamic world in which the inputs that lead to our desired outputs are ever-changing. Once you’ve spent a few years optimizing for a particular metric, and you have associated progress in that metric with a desired outcome, it is difficult to 1) recognize when that metric no longer generates the results you desire and 2) adjust your behaviors accordingly.

The optimal move, when these inputs and outputs dislocate, is to optimize for different inputs that now better correspond with your desired outputs, but, so often, we instead double down on our existing pursuits, despite the fact that they now yield increasingly-diminishing returns.

This idea of thinking through, “What am I optimizing for?” has crossed my mind a few times, but last Friday, I finally took some time to crystalize my thoughts on this phenomenon. Check out my latest blog below:

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What I’m Working On:

1. Back to San Francisco:
   After an aggressively-fun-filled summer in the greater New York area, I flew back to San Francisco for the fall last Sunday. One week in, my biggest takeaway from being back is that stability and routine are, unfortunately, incredibly valuable assets for one’s productivity. Anyway, I’m looking to kick it with interesting founders and other investors now that I’m back. HMU if you want to hang.

2. Our First Creator Investment:
   I’ve been spending a lot of my time this summer working on our Creator Fund. A lot of people have asked me, “What types of creators do you invest in?” The short answer is that we invest in “cult leaders” in different niches who have 1) built large, fast-growing audiences and 2) are leveraging those platforms to build larger, sustainable businesses, but I think it’s easier to understand our model through a real example vs. a high-level description. A couple of weeks ago, we went live with our $2 million investment in woodworking creator Jonathan Katz-Moses. Jonathan is the man, and he has quietly built a killer business on the back of his content engine. I recommend checking out the Forbes and TechCrunch features on our deal to learn more.

3. Messing Around with MCP:
   As part of my “AI tooling” rabbit hole, I’m curious about different/interesting MCP tools that people have built. For context, APIs have long been the “connectors” between different software platforms that allow Zoom to connect to your Google Calendar, or Typeform to automatically add the email addresses of folks who fill out a form to your newsletter. MCP (model context protocol) is like a USB-C for AI tools. It standardized the structure for connecting different data sources and software via API to AI tools like ChatGPT and Claude. For example, you can now easily connect your gmail to ChatGPT and ask it questions about folks you emailed last week. I have my Google Drive and gmail connected to Claude and ChatGPT now, and I’ve messed around with a few “fun” tools, like a Spotify connector that lets me control my Spotify with Claude, but if you’ve built / found any particularly novel MCP tools, shoot them my way.

4. New Travel Blog:
   If you’ve been following me for a while, you might remember that I wrote a regular travel blog in 2021 and 2022 detailing some of my shenanigans abroad. A couple of weeks ago, I published a new blog about my trip to Tel Aviv in May. Next travel blog probably hits when I go to a wedding in India in December; stay tuned.

5. Waymo Dating Show…?
   In a hysterical development, one of my coworkers introduced me to someone who’s launching a new “dating show” where two people are in the back of a Waymo, and if you make it to the venue, then your date is paid for. Like a blind-date Cash Cab. I have no idea if this is actually going to get filmed / produced or not, but there’s a non-zero chance I’m in the pilot episode if it comes to fruition. We’ll see.

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Ideas I’ve Been Thinking About:

1. Who has done the “acquire SMB and inject AI” thing well?
   An idea I’m seeing over, and over, and over again is that“AI is a God-tier technological shift, and you can now buy small businesses, replace their tech stack with AI-first tech, triple the margins, and print money.” This sounds great, but the problem is that there is an ever-growing delta between the speed at which AI models are improving and the speed at which “AI” can actually be implemented in new businesses. Everyone wants to “AI” their business, most people don’t actually know how to do it, beyond encouraging the adoption of LLM search tools and coding assistant-like products. I’m curious: has anyone reading this actually acquired a new business and put the “inject AI into small business” thesis into practice? How did it go? What sucked? What worked? What did “replace previous processes with AI” actually look like, once implemented? Even if you’ve just replaced your own internal tech stack with AI-first tools (no acquisition involved), I’d be curious to hear what the pain points and surprises were.

2. Latino Dave Ramsey?
   I mentioned above that we invest in “cult leaders” in different niches who have 1) built large, fast-growing audiences and 2) are leveraging those platforms to build larger, sustainable businesses. I think there’s a very real niche out there for “Latino Dave Ramsey.” Latinos are the fastest growing demographic in the US, the US Latino population has a $4 trillion GDP (which would be the fifth largest GDP in the world as a standalone country), and there’s a huge educational opportunity for a “Latino Dave Ramsey” to be the go-to personal finance voice for this population. For my LatAm folks, does this go-to voice exist? Is there someone that your parents point to as the GOAT for Spanish-speaking financial advice?

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Other Things I Enjoyed Last Week:

• Lux Capital founder Josh Wolfe is one of my favorite “thinkers” in the VC world, and Lux’s quarterly LP letters are always a treat to read.

• Kevin Kelly published a great blog post on all of the ins and outs of self-publishing vs. the traditional publishing model. Great read for any other writers out there.

• For any of my corporate finance / FP&A folks out there, Secret CFO has been publishing a series on understanding the optimal capital structure for your business. Good read if you want to nerd out on debt service coverage ratios and liquidation preferences.

- Jack

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