Closing deals

What should I do when an investor goes silent?

Short answer

Change the channel before you send another email. Silence often means the message was never seen, not that the answer is no. I would try a text, a short call or a quick video, send it during business hours, and then close the loop politely. If you still hear nothing, stop chasing and move on.

Start by asking whether the investor ever saw your message. If all your follow-ups were emails, the odds are not in your favor. I have looked at the numbers on this many times.

"Most people open 8% or less of their emails. Some people only open 2% of their emails."

Richard C. Wilson | Family Office Club Workshop- AI, Thought Leadership & Capital Raising Strategies

Try a different door

Text messages get opened far more often. I said at our workshop that most people open around 90% of texts sent to them. That number has probably dropped because of spam, but even at 50% it beats email. At Family Office Club we use a text line today and we are looking at moving to Twilio, which does more and connects to other systems better.

Phone calls work too, as long as you keep them short. We just started paying for PhoneBurner. It lets you leave a scripted one-line voicemail with one click and move straight to the next call. That can take a person from 20 or 30 calls a day to 100. Live chat on your website is another door, because many people will answer a chat before they answer an email.

This clip walks through the text, phone and live chat tools we use to reach people who do not reply to email.

Richard C. Wilson | Family Office Club Workshop- AI, Thought Leadership & Capital Raising Strategies

Make your next message easy to receive

A personal video can break the pattern. We use Loom for client updates and tutorials. You record your screen, they see who you are, and you can show them exactly what you mean. It also lets them watch on their own time, even at a faster speed.

Timing matters as well. I try to send things during business hours, and I schedule messages for Monday rather than ping someone on a weekend. With a new contact I am extra careful, especially across time zones. A message that lands at 3:00 a.m. does not help you.

Here I talk about scheduling messages for business hours and using Loom for personal updates.

Social Media, Advertising, $1M mistakes | Top Insights & Strategies | Capital Raising Workshop

Summary and key takeaways from this video

Close the loop, then let it go

After two or three tries on different channels, send one clear last note. Say what you were offering, say you will not keep following up, and say the door stays open. That respects their time and gives them an easy way to reply. Then move your energy to investors who are responding.

If you can meet in person, do it. My friend John shows up to his real estate closings whenever he physically can, and everyone at the table knows he is a real buyer. He did what he said he would do and followed through to the finish line. Showing up can get you noticed in a way another email often does not.

One more point. Many sponsors talk to a securities attorney about how to word follow-ups that describe an offering.

From the Family Office Club stage

One way to make silence easier on both sides is to attach a clear default to your message. I once heard the idea put this way: show me your deals an hour before they go out to your big list, and if I don't reply, it just goes out. The investor knows exactly what happens if they say nothing, so a missed reply is no longer a mystery. Use the same thinking in your own follow-ups. Say what you will do next and when, keep the ask small, and let their silence mean something definite instead of leaving you guessing.

"3% on each side of the trade. Maybe if you do the whole deal yourself, you make 5%. How about you show me your deals an hour before it goes out to your big list? If I don't reply, it just goes out."

From a Family Office Club event talk

From the source

  • Richard said most people open around 90% of text messages, while many open 8% or less of their emails and some only 2%.
  • Richard said PhoneBurner can help a team member get through about 100 calls a day instead of 20 to 30 by leaving a one-click scripted voicemail.
  • Family Office Club uses Loom screen recordings for tutorials and client updates, such as showing a client how to get into a data room.
Sources

From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Richard C. Wilson | Family Office Club Workshop- AI, Thought Leadership & Capital Raising Strategies, Social Media, Advertising, $1M mistakes | Top Insights & Strategies | Capital Raising Workshop. Quotes come from the video captions, lightly edited for readability. Figures are the speakers' own estimates and experience.

General education only. Not legal, tax or investment advice.

Talk to a securities attorney to explore options around investor communications wording, offering descriptions and outreach compliance practices. Do not use AI to write your own legal agreements.

Next moves

  1. Check how many of your follow-ups were email only.
  2. Send a short text and try a brief phone call.
  3. Record a short video that answers their likely question.
  4. Send messages during business hours in their time zone.
  5. Send one closing note, then move on.

More questions on this

How many times should I follow up with a silent investor?

I do not have a magic number. Try a few times across different channels, then send a clear last note and stop. Many sponsors talk to a securities attorney about how to word messages that describe an offering.

Is texting an investor appropriate?

It depends on how well you know them. With someone new, I am extra conscious about it and keep it short and respectful. Ask whether texting is okay.

Can a video help when an investor stops replying?

Yes. A short screen recording lets them see who you are and understand your point fast. We use Loom for this with clients.

Work through it with the family office fit check. See all closing deals resources.