After investing $25m+ into 150 companies over the past 10 years, I’ve come to believe that sending consistent written updates is the single biggest leading indicator of future success
Sending regular written updates can transform how teams, founders, and investors stay aligned. They’re a habit that builds accountability, trust, and momentum over time. When communication is consistent, people stay connected to progress instead of guessing what’s going on. The best operators don’t wait for someone to ask — they proactively share where things stand.
Why it works
- Written updates force clarity and reflection on what really matters.
- They show reliability and build confidence with investors or managers.
- Frequent updates reduce surprises and help catch issues early.
- Consistent communication strengthens relationships and keeps people engaged.
Companies putting it into practice
Buffer shares monthly transparency reports to keep stakeholders in the loop about growth and challenges.
Basecamp teams post regular written check-ins instead of endless meetings to maintain alignment.
Stripe founders known for disciplined investor updates helped set a standard for clear, consistent communication.
Analyzed by Swipebot
Text Statistics & Scores
An elementary to middle school score is best since it’s simple to understand.
Grade Elementary
6
Total Words
1
Total Sentences
6.0
Words / sentence
91
Flesch Score