The Diligence Vitamin 💊

Happy Thursday.

This week I'm considering when due diligence is a vitamin vs painkiller (it depends), reflecting on three key lessons from hitting 30 podcast episodes, and realizing how fun it is to connect former guests with each other.

Here are three things on my mind this week, plus some reads I think you'll enjoy.

🔖Bookmarks of the Week

1. PSA: New bill that would expand QSBS provisions hits the House floor soon. Angels - read up. 📜 | Congressman David Kustoff @Tennessee’s Eighth District (link)

2. What if the IPO drought is the “new normal”? 🤔 | Charles Hudson @ (link)

3. Another great chart on the impact of “small angel checks” from Peter Walker because all his charts are fantastic. 🔥 | Peter Walker @Carta (link)

🔍Three Things On My Mind

1. Is Due Diligence a Vitamin or Painkiller? 💊

Yup.

Every purchase decision, whether it’s buying a cell phone, purchasing a home, or investing in a startup, involves due diligence. For some, “my buddy likes it” is enough. For others, thorough, detailed analysis is 100% mandatory.

This equally applies in the realm of startup investing.

Here’s a hard-earned lesson after writing 200+ diligence reports for angel investors over the last few years: every investor has a threshold where they’ve got “enough” information to decide whether they’re in or out. 

All information collected prior to reaching that threshold? Need. Gotta have it. Give me the painkiller. Information above that threshold? Want. Nice to have. Sure, I’ll take the vitamin, but I’ll probably be fine if I don’t have it.

Here’s the tricky part - every investor’s “threshold” is different.

The answer to “How much is enough?” depends on your personality, portfolio size, check size, expertise in that business area, and so many other factors. An angel investor could fall anywhere on the spectrum from “More Gut” to “More Analytical,” but in general angels tend to require dramatically less diligence information than the typical VC, PE firm, bank, etc.

2. Three Lessons from 30 Episodes of the Diligent Observer Podcast 🎙️

I spoke at length with a friend this week who has published over 100 podcast episodes for his show. In recognition of releasing our 30th episode this week (the 3rd installment of our Deep Dive series on nuclear energy) with Ryan Marcum, I reflected on a few quick lessons from my podcasting journey so far.

1. More Niche is More Fun. I’m finding that general topics like “How to be a good angel investor” are far less interesting to me now than topics like “How to make smarter decisions when evaluating nuclear energy supply chain startups.” This hyper-specificity tends to draw out more nuanced and interesting insights. Having a topic that is broad (such as “helping angels make better bets”) but with unlimited niche applications (such as “helping angels make better bets in X”) has been hugely beneficial.

2. How to Honor your Guest: Prepare Well. There are two avenues that I’ve found to be most important: prepare the guest, and prepare myself.

   1. The Guest: Every guest is different - some prefer to have lots of guidance on the front end, others prefer to “just show up.” But by catering to the “plan ahead” type and delivering multiple rounds of check-ins, explainer documents, and examples of “what to expect,” guests of all personalities tend to feel comfortable and confident when it comes time for the recording.

   2. The Host: If I don’t spend at least half an hour preparing for the interview, there is a noticeable impact to conversation quality. 60m+ is better. I’ve also grown to rely on some AI workflows to help me quickly analyze a guest’s background and prepare a few question topics, but the more thoughtful preparation I can do, the better.

3. Build a System. I now 100% understand why most podcasts never release more than 10 episodes (apparently having 30 puts me in the top 1% of podcasters, yay!). It’s a stupid amount of work, and the treadmill never stops (especially with a weekly cadence). Editing, producing, and distributing an episode every single week is so much more involved than most people think. Building a reliable system and a team to drive consistent execution is so much more important than I ever thought it would be.

3. Introducing Two Former Podcast Guests is Fun 🤝

A fascinating thing happened this week: I got to introduce two Diligent Observer guests to one other.

In that moment, I also realized that somewhere along the way I’ve started mentally attaching “Episode X” to every person who comes on the show.

So the story in my head was “Episode X, meet Episode Y.”

Kinda fun.

⚛️A Note on Nuclear

I've spent the last few months deep diving into the early-stage nuclear energy investing landscape. After analyzing piles of Pitchbook data, interviewing industry experts, and reading way too much, I’ve pulled out the essential information to build the guide I wish existed when I started researching this space.

The Nuclear Energy Investing Playbook drops in March 2025. It includes analysis of 80+ startups, proprietary market research, and a framework to help angels navigate this complex but opportunity-rich sector.

Interested? Pre-order now for $79 (regular price $99). Want it for free? Subscribe and refer one friend to the newsletter (be sure to click the button to get a referral link) by March 15, 2025.

Until Next Week👋

Thanks for reading - have a great week.

-Andrew

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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.