How to Alienate Your Investors (Without Even Realising It)

Most founders think the hard part is over once the round closes. But your relationship with investors is just getting started — and how you manage that relationship can mean the difference between having a great champion in your corner… or falling off the RADAR when you need them the most.

Here are six ways founders accidentally push investors away — and what to do instead.

1. Going Quiet Between Rounds

One of the most common — and costly — mistakes founders make is disappearing after the deal is done. The money’s in the bank, and now it’s time to focus, right?

Wrong.

Going dark makes investors nervous. We start wondering:

Are things going badly? Are they hiding something? Should we be worried?

You don’t need to send weekly essays, but you do need to show up. A short monthly or quarterly update is enough to maintain confidence and keep the relationship alive.

Do this instead:
Set a simple cadence. Once a month, share a quick update that includes:

• Key highlights and lowlights

• KPIs (revenue, runway, burn, user growth)

• Team changes or new hires

• What you’re focused on next

• Any asks, intros, or support you need

Investors want to help — but we can’t if we don’t know what’s going on.

2. Sending “Vibe Check” Updates

Some founders try to gloss over issues with vague optimism. “We’re really excited about what’s coming,” or “Big things ahead!”

That might work on LinkedIn. It doesn’t work in investor updates.

When updates feel like PR instead of progress, it erodes trust. It makes you look out of your depth — or worse, deliberately evasive.

Do this instead:
Be real. Share what’s working, what isn’t, and where you’re stuck. Transparency isn’t weakness — it’s how you build long-term credibility. Good investors will respect your honesty and roll up their sleeves to help.

3. Only Communicating When You Need Money

Nothing says “transactional” like going quiet for six months and then suddenly dropping into inboxes with:
“Hey! We’re raising again. Here’s the deck. Any chance you’re in?”

Even if we wanted to back you, we’re missing the context. How’s the business doing? What’s changed since the last round?

Do this instead:
Give your investors a heads-up 6–9 months before your next raise. Share your early thinking, goals, and what kind of round you’re planning. Make it a conversation, not a cold pitch. Warm relationships raise faster.

4. Leaving It Too Late to Raise

If you’re starting your raise with 4-5 months of runway left, you’ve already lost leverage. Investors can smell the desperation. That’s when you get worse terms — or no terms at all.

Even great companies fall into this trap by assuming they can “just extend the runway” or “raise quickly if needed.”

Do this instead:
Start preparing for your raise 6–9 months before you need the money. That gives you time to test your story, build momentum, and course-correct if things don’t land right away. Better yet, it gives your existing investors time to engage, support, and open doors.

5. Not Involving Your Existing Investors

Too many founders treat their existing backers like check-writers, not collaborators. But these are the people who already said yes. They want to help.

If you don’t bring them into the loop early, they can’t offer feedback, introduce you to the right people, or help shape a round that gets momentum.

Do this instead:
Share early drafts of your pitch deck. Ask for feedback on your raise strategy. Let them know when you’re planning to go out to market — not after you’ve already started. A little involvement goes a long way.

6. Pretending Everything’s Fine When It’s Not

Some founders think they need to keep a stiff upper lip at all times. But if you’re missing targets, struggling with retention, or dealing with internal issues — and your investors only find out after things hit the fan — that’s a fast way to lose trust.

Do this instead:
Be honest early. A simple line like:
“We’re seeing higher churn than expected and testing a few fixes — happy to talk through if helpful.”
…is more than enough.

Most investors understand that growth isn’t linear. What we want to see is that you understand the problem and are taking action.

Final Thought

Good investor relationships aren’t built on flawless metrics or pitch decks. They’re built on trust, transparency, and consistent communication.

You don’t need to impress us. You just need to keep us in the loop.