This past week, I commented on a viral LinkedIn post from investor Zain Jaffer. He posted about an experience with a founder who provided no updates, no replies and said there was no legal obligation to give the investor either.
As you can imagine, this story touched a nerve, and it quickly racked up likes and replies from all sides on LinkedIn.
I joined in and added a simple comment. I said to just keep the line of communications simple, send bullet points, describe the good and the bad and stay in touch. My comment sparked a reply from Riley Budd, a founder I didn’t know at the time. He pushed back, saying that most founders are just trying to stay alive.
And he’s right. Before he said that, my main message, as I’ve posted previously, was that all a founder has to do is just stay in touch with your investors and they’ll have your back. And most importantly, they’ll be there next time you fundraise.
I didn’t wake up that day planning to defend VCs. But I’ve never met an investor who appreciated being ghosted after writing a check. As I said, I’ve written about this topic before, and I’ve seen how even simple communications can improve the VC-founder relationship.
But Budd made solid points. Startup life is overwhelming, isolating and often brutal. So having time to communicate with investors can feel like a luxury. Budd followed up with a more hard-edged take: that founders sometimes see people, including investors, as just heaping on the pile of more demands in a world where appreciation is rare.
Earlier this year, I spoke with Gavin Myers of Prudence for my podcast The Venture Variety Show. In the podcast, Myers said, “The worst feeling as an investor is the sensation that I’m being sold to. I already believe in you. I just need the complete, unvarnished truth.”
Myers doesn’t expect perfection. But like many investors, he values consistent and honest updates from his portfolio founders, and he views the relationship like that of a Marriage. Myers said he’s not trying to micromanage. But “locked at the arms” with a founder means going through the good times and the rough patches together. And that all starts with communication.
Here’s a clip from our podcast, which you can watch in full on my YouTube channel and other platforms.
In September, I posted on Substack about my conversation with Tom Lazay at Companyon Ventures. He told me about a founder who sent regular updates for 18 months, even after Companyon initially passed on the deal. That stream of transparency built trust and familiarity, and when the time came again, Companyon invested in the founder.
My takeaway from talking with Lazay was that entrepreneurs don’t need to write a novel to stay in touch with investors. Keep it short. Bullet point the highlights. Summarize any challenges and any asks. Think of it as a conversation, not a presentation.
“You don’t need a manifesto, just keep investors in the loop,” Lazay said.
But there’s another side to this, one that Budd helped to surface.
Many founders are burnt out, stretched thin and living with Anxiety and self-doubt, if not worse. In fact, I’ve witnessed the Stress and the panicked messages from my time covering VCs.
Last year, I met up with an investor for lunch. And afterwards, we grabbed a couple of espressos as we walked and talked around a mall. But our talk kept getting interrupted because he was fielding emails and calls from a portfolio company, where he sits on the board. There was a concern over top exec who was leaving and how to handle it. I thought the issue seemed minor, but the founder clearly needed the reassurance and Wisdom of this VC to get through the ordeal. It’s a reminder that sometimes a founder just needs someone to talk to.
So maybe it’s not that founders don’t care. Maybe they’re just maxed out. That doesn’t make silence the right call. But it shouldn’t be a negative. It could just mean that the founder is going through a lot and truly doesn’t have the bandwidth to reach out to anyone, including those on their cap table.
Running a startup is messy. So is fundraising. But communication isn’t just a tactical tool. It’s the foundation of every good partnership in venture.
Regular, honest updates don’t just keep investors informed. They build trust, invite support and give founders a chance to get ahead of problems before they become emergencies.
Even if you’re underwater, even if the numbers are bad, even if one of your top execs is leaving and you don’t know how to process the situation, that’s when communicating matters the most.
Drop a comment with your own experience, whether you’re a founder, investor or a comms person caught in between.
And if you’re struggling with how to write that update or what to say, shoot me a note.
Illustration generated with the help of ChatGPT.
