Author: Justin Park
Last updated: February 2, 2026
I once asked a long time investor of mine what surprised him after a dozen years of investing and partnering with over 50+ founders. His response was unexpected:
“You’d be surprised how few founders actually tell you what’s going on in their business. Very few establish a regular communication cadence—and the ones who do are generally the most successful.”
I’ve always taken investor relations seriously, and I pride myself on proactive communication. My email updates from 2022 and 2023 — seen below — eventually evolved into formal letters, but the core philosophy remained the same.
Over the last decade, I’ve learned that a great update isn't just "news"—it's a discipline. Here is my guide for mastering the cadence:
- The author should be the primary beneficiary. The act of drafting an external email forces you to anchor yourself, cut through the noise, and think critically about the current state of the business. If you aren't gaining clarity by writing it, you aren't doing it right.
- The "who" matters as much as the "what." Be intentional about your recipient list. Determine who needs to be in the loop to move the needle—and who might be a distraction.
- Every update, regardless of format, should answer these four questions. The last point is vital. Don’t be afraid to put your investors, colleagues, or mentors to work. Be specific with your "asks" and see who shows up for you.
- What have you achieved?
- What’s next?
- What are your biggest challenges?
- How can people help?
- Find a rhythm that matches your business cycle—whether that’s bi-weekly, monthly, or quarterly. The biggest pitfall is the "fading" update: starting with a bang and disappearing after three months.
2022 and 2023 Update Emails
Update Emails 2022 - 2023.pdf
Update_Emails_2022_-_2023.pdf