About a year ago, my co-founder and I left the company that we had founded and run for 10 years. Recently, one of the fellow founders in our Slack community asked this question.

After everything that happened, how did you manage to regain the trust of investors? How did you rebuild the trust of investors?

We Never Really Lost It

This is a very interesting question, and I wanted to actually answer this question from the very top, which is how do you build trust in investors?

First of all, we never really lost the trust of the good investors. Those who were watching this all from the sidelines or from the inside and knew exactly what happened still loved us.

After I was replaced as CEO and we eventually left, the investors who truly understood the situation continued to believe in us. The difference between smart money and dumb money becomes clear in moments like these. Smart investors evaluate founders, not just outcomes.

The Call That Same Evening

In fact, when I left, I felt responsible enough to personally notify some of the investors that I had resigned, so I sent a message to a number of them, and one of them called me that very same evening and basically told me, look, I don't know what you're going to do next, but I'm positive you're going to build again, and when you do, I want to be your first check-in.

And that was very, very heartwarming. And sure enough, he was our first angel check in the round.

How Trust Is Built From Day One

So what did we do to, first of all, build this trust from day one? The trust starts at the very first meeting you have with the investor, even before they invest.

The trust is what leads them to believe that they should be investing in you. But then after they invest, it doesn't end there. You cannot ignore them after they've invested.

When you're pitching to angel investors, you're not just selling your company. You're beginning a relationship that will last years. The way you communicate in those early meetings sets expectations for how you'll communicate throughout the journey.

Strategy #1: Never Miss an Update

What I've done is a combination of things. In the very early stages, I would send out a monthly update to all the angel investors and anybody who invested in the company. And then as we grew, I made that a quarterly update, but I never missed a single update ever.

Good news or bad news, they always knew they're going to hear from me every quarter.

Strategy #2: Keep It Raw (But Not Too Raw)

Two, I kept it fairly raw in these updates. If something was not going well, they would actually know that it's not going well.

But at the same time, I want to be careful about this. We can over-correct on the negatives because as founders, those negative situations actually affect us more, and we tend to downplay the positive sometimes. And I think this happens much more with women.

So you should be careful for that. You should watch out. You definitely want to communicate the good news very, very loudly. At the same time, you don't want to keep them in the dark about anything bad.

Strategy #3: Regular Calls with Key Investors

Three, I would actually have short calls with some of the key investors every now and then. Not so often, but every couple of months or so, spend 30 minutes with them, sit down, have a conversation, find out how they're doing, and share how you're doing.

Strategy #4: Never Ignore Questions

Lastly, whenever an investor reached out to me with any questions, I never, ever ignored them, no matter how small they were.

After I left, when people realized they stopped getting the updates, some of them actually reached out to me and said, hey, I haven't gotten an update on Rizzle for a while. And I was like, well, I'm no longer the CEO.

Turns out the new guy hasn't sent a single update to some of the investors.

The Simple Answer

So the answer is very short. Keep in touch with your investors. They'd appreciate it.

This consistency matters even more when things go wrong. When we lost a $300M acquisition deal and had to pivot, our investors stayed with us because they'd received honest updates throughout. They knew the challenges we faced and trusted our judgment.

At FinalLayer, we continue this practice. Every investor receives regular updates, good or bad. That consistency built trust in our previous company, maintained it through crisis, and carried over to our new venture.

Trust isn't rebuilt. It's maintained through consistent, honest communication over years. When you build it properly from day one, it survives even the worst outcomes.