Why do investors say maybe instead of a clear no?
Short answer
A maybe is the easiest answer for a busy investor to give. A no needs a decision, and a yes needs work. A maybe needs neither. In my experience it often means the investor does not yet trust you enough to commit, or does not have time to check. The fix is usually more clarity and more trust, not more pressure.
A maybe is the cheapest answer an investor can give. A no takes a decision and sometimes an awkward conversation. A yes takes real work and real money. A maybe takes nothing, and it keeps the door open in case something changes.
Busy people protect their time
I have studied influence and persuasion since 2004. One thing I keep coming back to is that everyone is busier every year. More messages, more pings, more people asking for something. Because of that, nobody has time to investigate every decision in full detail.
Here I explain why busy people lean on shortcuts when they decide, which is the root of many maybes.
Summary and key takeaways from this video
So busy investors use shortcuts. They look at who else trusts you, what others say about you and whether your message is easy to understand. If the shortcuts do not give them a clear signal, they do not say no. They put you in the pile for later. That pile is where maybes live.
A maybe often means trust is not there yet
Many founders and fund managers think the deal is what moves an investor. I do not think that is the main driver. I have seen the same deal land very differently depending on how it is presented and who presents it.
"Most investors would rather invest with someone who promises less but whom they trust 100%, and it's really transparent and well structured."
In this talk I show how one sentence of track record and a personal connection can change how an investor hears the same deal.
In that talk I gave an example. If you can say you have done this 22 times before and 142 other investors have trusted you with it, they might be 10 times more likely to do the deal. That is a hypothetical to show the point, not a promise of results. Pressure does the opposite. If you tell someone they must come in by next Friday, you may get nobody. Overpromising can have a similar effect and can make you look inexperienced.
How I would respond to a maybe
I would not chase a maybe harder. I would try to turn it into information. A few ideas:
- Ask what would make this an easy yes for them, and listen to the answer.
- Make your pitch shorter and clearer, with one line on your track record.
- Offer a simple next step, such as a short call or one document, instead of a big commitment.
- Set a calm follow-up date and keep to it.
- Accept a real no when it comes. It frees you to talk to the next investor.
Also keep your communication accurate and measured. Many sponsors talk to a securities attorney about how to describe an offering to investors.
What I have said on this at our events
One thing that helps turn a maybe into a clear answer is making your advantage easy to see. When investors are very clear on what makes you different, they are more likely to take a meeting and more likely to back you. I also watch for words that confuse people. If a third of your investors do not understand a term, I might keep it in the deck but leave it out of the one-liner and the name of the firm.
"If investors are very clear on your crystal clear advantage, they're more likely to take a meeting, they're more likely to invest with you, people are more likely to back you and work with you."
"If your investor doesn't understand it, or it confuses them, or a third of your investors get confused by the use of the term, then maybe use the term in your deck but maybe not in your one-liner, maybe not for the title of your firm."
Facts and figures
- I have studied influence and persuasion since 2004, including psychology coursework through the Harvard Extension School.
- I explain that busy people use shortcuts such as thousands of reviews at 4.5 out of 5 instead of investigating every decision.
- My example of 22 prior deals and 142 investors who trusted the sponsor shows how a single sentence can make an investor perhaps 10 times more likely to act.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: How to Ethically Persuade Investors and Close More Deals Using Proven Psychology, Inside the Mind of a Family Office: 100+ Strategies from 18 Years & 300 Investor Events. 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 offering communications, investor messaging rules and track record claims. Do not use AI to write your own legal agreements.
Where to start
- List the last five investors who said maybe and note what they still did not know about you.
- Write one clear sentence on your track record and your deal.
- Replace deadline pressure with a simple, low-commitment next step.
- Ask each maybe what would make a decision easy.
- Many sponsors talk to a securities attorney when they change how they describe an offer.
People also ask
Is a maybe from an investor ever a yes?
Sometimes, but not often on its own. A maybe with a clear reason and a next step is more promising than a maybe with silence.
Should I pressure an investor who says maybe?
I would not. In my view, pressure such as a hard deadline can push investors away, because trust comes before urgency.
How do I get a clearer answer?
Make your message simple, show a real track record and ask what they would need to see. A clear ask makes a clear answer easier to give.
Related questions
- What should I check before accepting money from a private investor?Before accepting money from a private investor, I check whether the investor understands the opportunity, whether expectations fit the proposed relationship, and whether the business is ready for scrutiny.
- How do I find high-net-worth investors for my business?Start by identifying the high-net-worth investors who are most likely to understand your business and have a reason to pay attention to it.
- What is a high-net-worth investor?A high-net-worth investor is an individual with substantial financial resources who may consider investing private capital.
- How do private investors invest in startups?Private investors invest in startups when the opportunity fits their interests, experience, and goals, and they understand the people and business behind it.
Work through it with the ready to raise checklist. See all investor psychology and trust resources.