- The Diligent Observer
- Posts
- Add Specialized Value or Get Outš¬
Add Specialized Value or Get Outš¬
The Observer's Notebook: Volume II, Entry 11 | February 6, 2025
Happy Thursday.
This week I'm thinking about how specialized angel groups are crushing it, how things being super hard to pull off can actually be a competitive advantage (especially in hardtech), and how you never create value faster than during a negotiation.
Here are three things on my mind, plus some reads I think you'll enjoy.

šBookmarks of the Week
šThree Things On My Mind
1. Add Specialized Value or Get Outš¬
Last weekās episode with Paul O'Brien featured a blistering criticism of the āpassiveā and āgeneralistā angel. This pattern highlighting the importance of āvalue-addā, which I first highlighted in my āBest of 2024ā post, has been on my mind a lot this week thanks to Paul.
Iāve heard from angel group leader after angel group leader how frustrating it is to see a member join, throw some money into a few deals they liked, and then quit after the 1st year because they got bored or couldnāt engage the way they wanted. I also see tons of groups struggling to effectively activate the expertise of their membership.
Contrast that with Medical Mondays, a collaboration put together by the TCA Venture Group with the help of Small Business Development Centers (SBDC) in Austin TX and Octane in Irvine CA. The collaboration is between angels groups, early VCs and hospitals. Every single week, a few dozen angels who are experts in various medical professions gather to hear startup pitches. Not dissimilar from the typical angel group.
But hereās where things diverged from āthe usualā: I recently got to observe this community, and let me tell you, every single person on that call could add crazy value for any startup presenting. Pediatricians. ER doctors. Hospital execs. Analysts for healthcare VCs. All in the room. This is a group you need to pitch if youāre part of the ~30% slice of the startup ecosystem focused on developing new medical technologies. That room was no more than 1 or 2 connections away from a world class expert on just about anything a founder could throw at them.
Iām becoming more and more convinced this is what great angel investing looks like. Highly specialized, sector-specific, value-additive capital allocation that is way more about the value-add than it is about the dollar-add.
The question is not just āShould I punch a $25K ticket on this one.ā More importantly, itās āShould I invest my time and network to help this one win?ā
Takeaway for community builders and network leaders: go deep, not wide. Build specialized segments to draw differentiated angel and founder talent.
2. Risky + Hard to Pull Off = Awesome Moatš”ļø
Things that are hard to pull off (i.e. launching and scaling new hardtech) represent a strong moat - my conversation this week with Doug Lee reminded me of another recent conversation with Texas A&M Innovationās Pete ONeill that touched on this same point.
Hereās a quote from Doug:
āThere's a huge execution risks around these types of technologies. So when you combine these things - capital intensive, long timelines, hard tech risk - there are some reasons why investors are afraid to be in this space!
However, if you take the other side of the coin, if you're any good at what you're doing, if this truly is where your unfair advantage lies, then those same barriers are there for other people.
So this becomes a moat.
3. āYouāll Never Create More Value Per Hour Than During a Negotiation.āš°
Most people hate negotiating.
Theyād rather āsplit the differenceā and avoid the emotional strain.
Mistake.
One of my favorite quotes from business school: āYouāll never create more value per hour than during a negotiation.ā And one of the best books Iāve read on the topic is āNever Split the Differenceā by Chris Voss. Highly recommend.
This week I am reminded how true this quote is.
A few thoughtful emails + a couple meetings + some creative attempts to make the pie bigger for everyone = thousands of dollars in value.
Iām learning.
Until Next Weekš
Thanks for reading - have a great week.
-Andrew
P.S. Your feedback helps improve this newsletter and teaches the algorithms to share it with more people. If you enjoyed this post, hit the "like" button or leave a comment with your thoughts.
How did I do this week?
About Me
I cultivate flourishing.
I'm also the CEO of PitchFact, where our mission is to cultivate flourishing specifically through efficient and collaborative early-stage diligence. I'm a proud husband, grateful father, and honest friend. My love languages include brisket, bourbon, and a handwritten note.