Over the past few months, I’ve met with numerous founders preparing to raise capital in the first half of 2025. A recurring theme has surfaced: communication gaps with their existing investors.

This trend isn’t surprising. Our industry lacks standardized communication practices between investors and founders. And given the choice, most founders would rather focus on customers, product development, and team building—the real work. However, maintaining candid investor communication is crucial—especially if you haven’t raised in a while. Neglecting it can lead to prolonged fundraising timelines, unexpected shifts in round dynamics, and challenges in securing capital when needed most.

If this resonates with you, here are a few thoughts I’ve shared in recent conversations that might be helpful.

1. Ship the Update

Founders often hesitate to send updates when progress feels slow or setbacks arise. But investors prefer transparency over silence. Regular updates, even without major milestones, showcase your leadership—resilience, adaptability, and commitment to growth.

Even if you don’t have significant product or revenue progress, share what you’re learning, experiments you’re running, and how you’re adapting. Prioritize authenticity over perfection. Your investors backed you, and regular communication fosters confidence, regardless of short-term results.

2. Make the Update Useful — Give Homework

Too many investor updates don’t include a request for support. These updates serve investors and their finance teams, but they should also be valuable to you. Make them mutually beneficial.

Reflect on where you need help—introductions to new investors, potential board members, a key GTM hire, a connection to a CIO, etc. If you don’t ask, it won’t happen. If an investor isn’t responsive or their feedback isn’t helpful, that’s another issue to explore. But you won’t know unless you make the request.

3. Ask the Awkward Questions Early

Many founders assume their existing investors will participate in the next round, but that’s not always the case. Partners transition, fund strategies shift, and priorities change—especially in the current market. Decisions to reinvest can be impacted by many factors. A few I’ve seen recently include partner departures, fund performance, and policies around pro-rata and ownership thresholds.

Rather than waiting until a formal fundraising process, ask the uncomfortable questions early. Push for clear answers. Doing so will save you time and energy and help you understand how to engage and leverage your investors moving forward. Ideally, investors should be engaged throughout your journey, but a direct conversation about reinvestment can surface important insights and actionable feedback early.

Final Thoughts

These suggestions are simply reflections from recent conversations. Building a great business is always the priority, and strong investor relationships can amplify your success.

If you haven’t been sending updates, now is a great time to start and build the habit. Put your investors to work, and ask the tough questions now. Regular, candid communication can pave the way for smoother fundraising and stronger partnerships over the long run.