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- Welcome to the Gildre December 2025 Newsletter - How to Communicate Like a High-Trust Founder
Welcome to the Gildre December 2025 Newsletter - How to Communicate Like a High-Trust Founder
December’s theme at Gildre: Company KPI’s & Growth Plans!
As our final topic of the year, we’re closing, as always, with strategies to gain an edge with investors and secure not only funding, but also a strong track record of meaningful business relationships, since, in the end, it’s often the same circles of people you’ll be dealing with.
Dive into the content and see how you can continue to scale .

How to Write Company Updates
Your update serves three primary audiences and purposes:
For Existing Investors: To build trust and confidence. Showing you can plan, execute, and communicate transparently, even when things are tough. They need to know the runway and be prepared for the next raise.
For Prospective Investors (The "Drip Campaign"): To build a track record before you raise. VCs invest in lines, not dots; consistent updates show you consistently execute on your stated goals.
For Yourself (The Founder): To force, reflection and discipline. It pulls you out of the day-to-day weeds to assess the business at a high level on a consistent cadence.
If you skip an update when things are tough, it sends a HUGE negative signal. Consistent communication is more important than consistent perfection.
2. A Template for Insight
Adopt a consistent format so investors can easily scan and compare data month-over-month. Keep it short and concise, investors read dozens of these. Aim for a monthly cadence in the early stages.
A. The TL;DR (The Crux of the Update)
Start with 2-3 bullet points summarizing the most important takeaways of the month (one win, one challenge, one key metric movement). This respects the investor's time.
B. Financial Health & Key Metrics (The Facts)
This section must be consistent. Use a clean table or bulleted list. Always include context/change.
$\text{Cash in Bank}$: The hard number.
$\text{Monthly Burn Rate}$: How much cash you spend monthly.
$\text{Months of Runway (ZCD)}$: Your Zero Cash Date. Crucial.
Focus on execution and things that explore how you can scale-risk the business.
Customer/Traction Wins: New significant customer, partnership signed, high-value feedback.
Product Milestones: Major feature shipped, successful Beta exit, key infrastructure improvement.
Team: Key hires onboarded (especially critical roles like a Head of Sales/Tech).
D. Lowlights & Challenges (The Reality Check)
Transparency builds trust. Don't just list problems; add context and your plan to fix them.
The Challenge: Be specific. Example: "Customer trials dropped 15% MoM."
The Context/Learning: Why did it happen? Example: "We believe this is due to a new competitor campaign and a slight dip in our onboarding conversion."
The Action Plan (Next Month's Focus): What are you doing about it? Example: "Bringing in an SEO specialist next week to boost top-of-funnel traffic and A/B testing the first 3 steps of our onboarding flow."
E. Focus for the Next Month (Setting Expectations)
This shows you are planning and prioritizing. Only list the top 1-3 critical initiatives.
Example: "Finalize GTM strategy for Q3," "Ship V2 of the core analytics dashboard," "Interview final two candidates for Head of Engineering."
F. The Ask (Making It Actionable for Them)
This is where you leverage your investor network. Be specific and one-to-one in your request.
Hiring: "We are desperate for a Senior Backend Engineer with experience in $\text{X}$ database. Can anyone introduce us to a relevant candidate?"
Customer Intros: "We are targeting medium-sized logistics firms. Does anyone have a direct connection to a VP of Operations at a company like [Target Company Example]?"
Advisory: "We are solidifying our pricing model. We'd love an hour of time with someone who has scaled B2B SaaS pricing from $5k to $50k ACV."
3. Realistic Advice: Mindset & Tactics
Don't Overcomplicate Decisions: Use the One-Way vs. Two-Way Door framework. If a decision (like a website tagline change) is easily reversible, make it fast and move on. If it's a one-way door (like changing your core product name), dedicate time for judicious thought.
Focus on Core Strengths (KISS Principle): In the early days, don't try to solve every problem. Focus on your core value proposition for a small, clearly defined audience, then expand.
Your Role Evolves: You start as Chief Building Officer (product focus). You transition to Chief Decision Officer (team/strategy focus). Acknowledge this shift.
Hire Intentionally: Take more time than you think to select the right people. A bad early hire is toxic; a great early hire is a force multiplier. Know when to part ways quickly if it's not the right fit.

If there’s a company that really lives everything described in that “how to write company updates” framework, it’s Buffer. They’ve basically built their entire culture around being radically transparent. Not just when things go great, especially when things get messy.
They’re the kind of team that actually publishes their numbers, their salaries, their roadmap, even the tough moments most founders want to hide. When Buffer hits a challenging month, they don’t skip the update like many startups do. They talk about what happened, why it happened, and what they plan to do next. And because they’ve been doing this for years, their community and investors can literally track their progress month by month.
What’s cool is that this habit wasn’t just about investors. Their CEO, Joel Gascoigne, has said multiple times that writing these updates forces him to zoom out, reflect, and actually think like a leader instead of staying stuck in daily tasks. It’s exactly the founder mindset shift your content talks about: moving from “chief builder” to “chief decision maker.”
Their updates nail what you were saying: a quick overview, then straight to the metrics (cash, revenue, burn). They're super clear about what worked, what flopped, and what's next. This steady, simple, and honest rhythm builds serious trust, not because everything is perfect, but because they keep it genuinely real.
Buffer is a fantastic example because they show that transparency isn't just a strategy, it's a consistent habit. This habit helps assure investors that things are getting done, encourages the team to think critically, and keeps the founder down-to-earth. That's the vital energy we really need to keep alive.
This Diana’s talk connects awesome company updates to how we actually build products (from "Discover" to "Deliver"). It's all about making product development a never-ending cycle of learning and getting better. Launching fast with MVPs and betas, then looking at usage data, keeps us on track with what customers actually need. With AI speeding up prototypes, "Deliver" is less about one massive launch and more about consistent progress. The habits that give you killer product processes, quick MVPs, fast iterations, and avoiding tech debt, are the same ones that lead to great investor updates: keeping it clear, showing momentum, staying focused, and being honest. You can check out the video for more on these concepts.
We’ve recently partnered with Stephanie Rieben and the Diadem Capital team to provide insights and access to world-class fundraising practices along with investor intros.
She’s hosting an 8-week VC Master Class for early stage founders which offers a live bootcamp to build your fundable story, VC-grade deck, and real investor pipeline.
You can book some time with her for a conversation or visit their bootcamp site at: https://app.diademcapital.com/bootcamp

Most costly mistake founders make is prioritizing speed and volume over quality and fit in their first ten hires. The stories of companies like Groupon (operational maturity) confirm that the initial team defines the company's DNA and its ability to scale sustainably.
If you’re interested in learning more about the Gildre Community you can schedule a conversation with Managing Partner, Taiga Gamell here.
Hope you have an amazing holiday season and use the time to reset and get ready for an even better 2026,
Eliana
