I’m riding shotgun for the founder of a VC-backed company as he sells his company. The process has been fun, tons of work, and highly educational. Selling a VC-backed company is different than selling a non-VC-backed company. The cap table is more complex, and many rights related to the sale of a company are embedded in the terms of VC-led fundraising rounds. Because of this complexity, more review is needed to make sure everything is in order. Cue the lawyers.

A big takeaway is that legal fees can be a material percentage of deal size, regardless of the size of the deal. As one lawyer put it, M&A legal fees don’t scale down well unless the buyer is willing to accept potentially material risks—IP isn’t cleanly owned, liens exist, pending litigation, etc. It’s not uncommon for each side to get a $30k–$50k bill for a small deal (think more than $100k but less than $500k). Deals over $1 million can involve legal fees for each side that easily exceed $100k.

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Cumulative metrics (since 4/1/24):

• Total books read: 86
• Total blog posts published: 567

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 10/26/25 (link to the previous week’s commitments):

• Read More Than You Know, a collection of essays about multidisciplinary thinking by Michael J. Mauboussin that targets investors

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Pick my next weekend project and start working on it

Asks:

• No ask this week

Week two hundred ninety-one was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• No material struggles related to this project

What I learned:

• No material learnings related to this project

That’s what I learned and struggled with last week.

One of the founders I know is in the process of getting acquired. I’m working closely with him to help get it over the finish line. Lots of moving pieces and parties are involved, which makes it interesting. It feels like putting together a puzzle. I’ve learned a good bit so far, and I’m pretty sure I’ll learn a ton more before this is over. I’m excited for the founder and what awaits him on the other side.

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My new weekend project begins this weekend. What will it be? I don’t know. I’m still trying to decide what idea to pursue. But I’m leaning toward trying something much shorter in duration so I can get a feel for that type of project. (I want to understand the optimal duration better.) I’m considering doing a one-month project so I can compare that duration to six months. Another advantage would be that I could complete two more weekend projects before the end of the year, for a total of three. I’ll decide in the next day or two, but that’s what I’m leaning toward right now.

I’ve read two books by Michael J. Mauboussin, an investor and a professor at Columbia University. I’ve enjoyed learning and trying his frameworks, especially the expectations investing framework. Another concept he wrote about was the investment premortem, an analysis you do before you invest when you’re objective and your mind isn’t anchored (as it will be after you’ve already invested).

To create this document, you fast-forward a year or so and pretend your investment has failed. You then list all the possible ways the investment ended up in that worst-case scenario. Most people naturally focus on what could go right and their own belief that an investment will work. The goal of the premortem is to get you to consider negative alternative outcomes and ways to mitigate them.

This approach caught my eye, and I want to try it. Thinking in terms of scenarios and the probabilities of those scenarios occurring is something I’ve noticed successful entrepreneurs and investors doing. I’ve started doing more of it, but I want to improve. This premortem idea seems like a great way to force myself to crystallize my thoughts about scenarios that are the opposite of what I hope happens. And it’ll likely help me have more confidence in assigning probability weights to the bad outcomes that I don’t expect.

A friend shared Stripe and OpenAI’s new Agentic Commerce Protocol (ACP) with me. ACP is an open-source interaction model and an open standard that lets buyers, AI agents, and businesses complete purchases. Translation: ACP will enable buyers and sellers to complete purchases, using AI agents, within an “AI surface” (think apps like ChatGPT).

As I understand it, when a buyer wants to purchase within a chat app, an AI agent works with them, showing products, offering checkout, and collecting payment. The business receives order details and payment information from the AI agent and can accept or decline the transaction. The AI agent facilitates payment via the business’s payment provider and sends payment details via a secure token (I assume after the buyer accepts the transaction), which the business can use to charge the buyer. If all goes well, the buyer can check out instantly via an app like ChatGPT without ever leaving it. It’s a seamless experience.

This is interesting stuff that could really change how commerce is done. It’s brand new, and I’m curious to learn more about it and follow its development. If you want to learn more, you can read Stripe’s blog announcement here and visit the ACP website (which links its GitHub) here.

In 2024, I challenged myself to accelerate my learning by reading a book (usually a biography) a week. To date, I’ve done it for 85 consecutive weeks. I wanted to share what I was reading and also keep track for myself, which was difficult (see here), so I created a Library section on this site. I added to it all the books I’ve read since my book-a-week habit began in March 2024, and I’ve committed to adding my latest read to the Library every Sunday (see the latest here).

That left the books I’d read before 2024 unshared and untracked. I set a goal to add my old reading to the Library over time. It began with a Memorial Day Challenge to add five books (see here) and continued with by challenging myself to add two books every weekend until my backlog is gone. Last month (see here), I decided to up the pace so I can finish this project well before the holidays—and begin another one!

The backlog is finally gone. This past weekend was my twentieth and final weekend, and I added the last two books:

• Liar's Poker by Michael Lewis
• Business Adventures by John Brooks

That’s the latest and final update for this weekend project. I’m glad I took this project on. It forced me to revisit tons of books, which jogged my memory.  I hope that sharing these books will add value to others.

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Cumulative metrics (since 4/1/24):

• Total books read: 85
• Total blog posts published: 560

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 10/19/25 (link to the previous week’s commitments):

• Read Think Twice, a framework to improve decision-making in complex and uncertain environments by Michael J. Mauboussin
• Added two more books to the library on this site; these, which I read in 2017 and 2016, were about Michael Lewis’s time as a Salomon Brothers bond trader in the 1980s and 12 business case studies on how human behavior in stressful times shapes decision and outcomes

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Pick my next weekend project and start working on it

Asks:

• No ask this week

Week two hundred ninety was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• No material struggles last week

What I learned:

• I learned about Kidlin’s law last week. It states that if you write a problem down clearly, then the matter is half solved. This really stuck with me, and I’ve been thinking about it all week. I’ll share my thoughts on this in the upcoming days.

That’s what I learned and struggled with last week.