Interestingly the prep in data rooms are mostly terrible.. we're in the process of building a few for founders ie like a product for subscribers. Roll in 2026
Great list. Bypassing market validation is, IMHO, by far the biggest mistake. Building products and services for a problem that doesn't exist is a killer.
Thanks Chris, this is such great advice, and it seems crazy to me that people would not be doing most of these things as the bare minimum. Thank you for the playbook at the end as well, a very helpful checklist! 🙏
Due diligence often feels like a background check, but what it really tests is whether you’ve built a company that can withstand outside scrutiny...or just one that looks good in a deck.
Most people are building something for a problem that no one cares enough about - plain and simple. It's worse when the founders cares about the idea 100x more than the person they're trying to sell it to. The trick is just reverse that statement - find something someone cares about 100x more than anything else. Something they're banging the table to get fixed
Great breakdown on preparedness over polish. The cap table point is especially underrated since i've seen multiple deals stall just because founders didn't secure propr IP assignments from early contractors. Its wild how something so fixable at the start becomes an existential risk later. Would add that getting audit-ready documentation before starting outreach saves way more time than most founders realise.
Preparation is the quiet advantage most founders skip.
Interestingly the prep in data rooms are mostly terrible.. we're in the process of building a few for founders ie like a product for subscribers. Roll in 2026
Great list. Bypassing market validation is, IMHO, by far the biggest mistake. Building products and services for a problem that doesn't exist is a killer.
Hallelujah! Ain't that the truth - mind blowing 🤯
Thanks Chris, this is such great advice, and it seems crazy to me that people would not be doing most of these things as the bare minimum. Thank you for the playbook at the end as well, a very helpful checklist! 🙏
My pleasure. The challenge for founders is there is so much to do that's totally uncertain combined with fierce constraints - time, money, resources
Due diligence often feels like a background check, but what it really tests is whether you’ve built a company that can withstand outside scrutiny...or just one that looks good in a deck.
Which one would you say is the most common?
Most people are building something for a problem that no one cares enough about - plain and simple. It's worse when the founders cares about the idea 100x more than the person they're trying to sell it to. The trick is just reverse that statement - find something someone cares about 100x more than anything else. Something they're banging the table to get fixed
They say the numbers don't lie but I think there's a lot of feel involved in these transactions too.
Feel, hope, greed, anxiety, fear, anticipation etc etc
I've seen too many founders pitch the hockey stick without being able to defend the first inflection point. Sending your article to my CEO.
So so true. Simple milestones. Critical path. Operate in sprints.
Founders who prepare for due diligence before they need it raise faster, negotiate better, and stay in control.
"no surprises" - one trick is to get a friendly to devils advocate and war game everything before you go out at all - "Forewarned or is forearmed"
Great breakdown on preparedness over polish. The cap table point is especially underrated since i've seen multiple deals stall just because founders didn't secure propr IP assignments from early contractors. Its wild how something so fixable at the start becomes an existential risk later. Would add that getting audit-ready documentation before starting outreach saves way more time than most founders realise.
Wise words! Thanks for sharing ✅