Two follow-ups, then only news: the investor update template for prospective investors that Barry Silbert handed me

Sunny Ray · May 28, 2026 · 5 min read

Two or three follow-ups is the limit for a deck. After that, only news earns you another email.

A founder brought me the classic problem on May 27. Investors had asked for his deck. He sent it. Then silence. He'd done one or two gentle follow-ups and stopped, because he didn't want to be the founder who nags. He wanted to know what to do next.

My answer: stop asking and start updating.

The deck went out, then silence

Silence after a deck is the most common state in fundraising, and it almost never means no. It means not now, not yet, or not enough. The investor read it, didn't see a reason to move this week, and moved on to the fifty other things in their inbox.

The mistake is to keep asking the same question. “Did you get a chance to look at the deck?” has one answer by the third time, and it's the delete key. Every repeat of the ask without new information spends a little of the goodwill the first reply earned.

Two or three follow-ups, then stop asking

For an investor who asked for the deck, I'd send two or three basic follow-ups. That's courtesy. Some people genuinely missed it.

Beyond that, you need a new reason to write. A new contract. A product milestone. A hire. A number that moved. New information resets the conversation, because now you're not asking for attention, you're giving them something that might change their view.

This founder was already doing something close: one or two nudges, then stopping. The fix wasn't more nudges. It was switching modes.

The update format, section by section

I pulled up the update format I've used for years on the call. In my words: “the update format that I use for all of my existing investors.” And where it came from: “this was given to me by Barry silbert who's like one of the like most prominent investors in bitcoin crypto.” I used it for Unocoin's investor update in November 2021.

The sections:

• Health check. One line on how the company is doing overall. Honest.
• Key metrics. The handful of numbers that matter for your stage, with the change since last time.
• Good news and bad news. Both. The bad news section is what makes investors trust the good news section.
• Budget update. Where the money is going and how long it lasts.
• Sales and marketing. Deals, pipeline, launches.
• How investors can help. Specific asks: an intro, a hire, a customer.

That last section is the quiet engine. Investors like being useful, and an investor who made an intro has a stake in how the story turns out.

Trimming it for prospective investors

The same format works for prospects, with one change: take out the sensitive financial detail. A prospect doesn't need your exact cash position or burn. Existing investors are owed that. People who haven't invested aren't.

What stays is progress. For this founder, the content to lead with was contracts, technical developments and any measurable progress. Those are exactly the things that make an investor who passed on the deck take another look. The update becomes a running record that the company is doing what the deck said it would.

The “how you can help” section works especially well with prospects. Asking a prospective investor for an intro or advice is a way to start a relationship that isn't a funding ask.

Cadence: regular, with real news

Monthly is the baseline, and on the call we talked about going weekly or every two weeks during an active push. What matters more than the exact rhythm is that it's regular and that every update has something real in it. Don't invent a milestone to fill a slot. A short update with one honest win beats a long one stuffed with filler.

The worry founders have is that they'll annoy people. Here's what I told him: “rarely will investors be like never call me never write me a never because they don't lose anything by they lose a lot if they make a mistake.”

That asymmetry is the whole game. Reading your update costs an investor thirty seconds. Missing the company that later takes off costs them much more. So they stay on the list. And six months of steady updates is the best evidence a founder can give that they execute.

One more rule from that call: report real progress, not forced timelines. Don't write “we expect to close the round in three weeks” to manufacture urgency. Investors have read that line a thousand times. Write what happened. If the news is strong, the urgency takes care of itself.

Health check: steady, on plan. Key metrics: [two or three numbers, with change]. Good news: [the contract or milestone]. Bad news: [the honest miss]. Sales and marketing: [what shipped, what's in pipeline]. How you can help: [one specific intro].

That's a prospect update. Six lines, sent on a schedule.

Other ways to stay in front of investors

Updates aren't the only tool. I suggested a podcast or interview format to this founder, where investors come on as guests and the relationship builds through the conversation. He felt it was off-brand for his company, which is a fair call. Know your audience.

The alternatives we landed on were good ones: private investor chats around his category, and an industry report built with AI help from his own insights, shared in a short version with an offer of the full one. Same principle as the update. Give investors something worth reading, and the asks get easier.

If your deck is out there and the replies have stopped, write the update this week. If you'd rather have investors coming to you as guests on a show, that's how we keep investors warm.

Frequently asked questions