What Investors Don’t Tell You About Fundraising: 5 Takeaways from Ugly Talk

At our recent Ugly Talk event, we invited investors to talk candidly about what founders don’t usually hear out loud during the fundraising process.

Not the polished advice.
Not the generic “keep going” encouragement.
The actual dynamics behind investor conversations, investor silence, and investor decision-making.

A few themes came up repeatedly — and they’re worth paying attention to because they can help founders interpret investor behavior more accurately and navigate fundraising more effectively.

1. “You’re not a fit for our thesis” is often not the real reason

One of the most common rejections founders hear is:

“You’re not a fit for our thesis.”

Sometimes that’s true. But often, it’s also the easiest way for an investor to say no.

The actual reason may be something else entirely:

• the investor doesn’t believe the market is large enough
• they’re not convinced by the founder-market fit
• they don’t think the opportunity is being presented clearly
• they’re not seeing enough traction or proof points
• they’re unsure whether the founder can navigate the pivots and challenges ahead

In other words, “not a fit for our thesis” can sometimes be a catch-all response rather than the real reason behind the pass.

Why? Because many investors don’t want to upset founders, get pulled into a long explanation, or deliver feedback they worry will be taken personally.

That’s why one of the best things a founder can do after a pass is ask for feedback and ask the investor to elaborate.

You won’t always get a fully transparent answer. But sometimes you will. And when you do, the insight behind the “no” can be incredibly useful. It may reveal a weakness in your story, your positioning, your traction, or your overall fundraising readiness.

The panel’s advice was clear: if you want a more honest answer, ask for one.

2. Ghosting is usually not personal — but responsiveness matters on both sides

We also talked about one of the most frustrating parts of fundraising: investor ghosting.

From a founder’s perspective, silence can feel personal. You send a follow-up, then another one, and hear nothing. It’s easy to assume the investor is intentionally ignoring you.

What the investors on the panel said was more nuanced.

Ghosting is usually not the goal. Sometimes they’re simply overwhelmed:

• they’re juggling portfolio companies
• they’re in active deals
• they’re receiving a huge volume of emails and LinkedIn messages
• something genuinely falls through the cracks

Their advice to founders was straightforward: if you’re in an active conversation and an investor goes quiet, don’t take it personally — follow up.

A thoughtful follow-up is not a problem. In many cases, it’s necessary.

At the same time, the panel made an equally important point from the other side of the table: founders can lose momentum by being slow to respond too.

Venture is a fast-moving business. If an investor asks for financials, diligence materials, customer references, or other information, they want to see that you have your materials ready and can provide them quickly.

That means having your ducks in a row:

• a clean deck
• a data room
• financials
• traction data
• clear answers to likely diligence questions

If an investor is leaning in and the founder is slow, disorganized, or unable to produce basic materials, that can absolutely kill a deal.

So yes, don’t over-interpret investor silence. But also make sure you’re not creating friction when the ball is in your court.

3. Investors are looking at the founder as much as the company

Another major theme from the conversation was that early-stage investing is not just about the business. It’s also very much about the founder.

Investors want to understand the connection between the founder and the company:

• Why this problem?
• Why this founder?
• Why now?
• What gives this person the credibility, knowledge, or obsession to solve it?

They also want to understand how a founder handles difficulty.

The panelists shared that they pay attention to whether a founder can point to moments where the company had to overcome challenges — because those moments reveal a lot. They show execution. They show flexibility. They show humility. They show whether a founder can adapt when something doesn’t go according to plan.

And those qualities matter.

The green flags investors mentioned included:

• knowledge of the customer and market
• resilience
• flexibility
• humility
• passion for the problem
• the ability to keep moving through setbacks

In other words, investors are not looking for a founder whose path has been perfectly smooth. They’re looking for a founder who has faced friction and kept building.

4. Complaining kills confidence

One of the more direct investor comments at the event was about what turns them off in a fundraising conversation.

They don’t want to hear founders complain.

That includes complaining about:

• how hard fundraising is
• how long the process takes
• how frustrating investors are
• another investor who passed
• how unfair the market or ecosystem feels

To be clear: fundraising is hard. It’s time-consuming, emotionally draining, and often opaque.

But investors are paying attention to how you handle that difficulty.

When a founder slips into complaint mode, it can raise questions about how they’ll respond to the much bigger challenges that come with building a company. Investors are looking for founders who can handle adversity, stay constructive, and keep moving.

When something is hard, your instinct is to solve the problem — not spiral around it.

5. If your numbers don’t hold up in diligence, trust breaks fast

Another important point the investors raised: don’t make claims you can’t back up.

That includes overstating your sales pipeline, inflating traction, or making loose statements about customer demand that won’t hold up once diligence begins.

Investors understand that early-stage companies are messy. What they don’t like is when the story changes under diligence.

If you say the pipeline is strong, be ready to show it.
If you say traction is accelerating, the numbers should support it.
If you imply customer demand is stronger than it really is, that will come out.

And when it does, it doesn’t just weaken the business case. It damages confidence in the founder.

Investors can tolerate risk. They can tolerate early-stage uncertainty. What they struggle to tolerate is a founder who makes statements they can’t back up.

Final thoughts

Fundraising can feel confusing partly because so much of it is indirect.

A “no” may not contain the real reason.
Silence may not be personal.
And the qualities that create investor conviction are often more human and qualitative than founders expect.

That’s exactly why we hosted Ugly Talk.

Founders don’t need more polished fundraising clichés. They need a more honest picture of how investors actually think, what they pay attention to, and what can quietly derail a deal.

The more clearly founders understand those dynamics, the better they can prepare — not just to pitch, but to build the kind of company investors can actually believe in.

Victoria Yampolsky is a serial entrepreneur, strategic CFO, startup advisor, and expert in financial modeling and valuation. She’s a passionate advocate for female founders and fair access to capital for all. 

As the President and Founder of The Startup Station, a strategic CFO advisory firm and financial education platform for startups and small businesses, she has collaborated with over 150 founders across 15 industries, assisting them in raising more than $50M in venture capital funding.

Victoria has taught finance to over 20,000 entrepreneurs worldwide through The Startup Station’s courses on accounting, financial modeling, valuation, and startup finance, as well as through The Startup Station’s meetups, 15+ accelerators, and the Bank of America Institute of Women’s Entrepreneurship at Cornell. With veteran investor Jeanne M. Sullivan, she is now running the Fundraising Bootcamp for revenue-generating/MVP market-ready startups.

In 2023, Victoria represented New York State on the NSBA Leadership Council, advocating for fair access to capital for women. She is currently working to pass NY State Bill A09786 to promote diversity in venture capital.

Before venturing into entrepreneurship, Victoria spent nearly a decade on Wall Street in Deutsche Bank Research and IT Consulting at CapGemini. 

Victoria holds a Bachelor’s degree, cum laude, in Computer Science with a minor in Mathematics from Cornell University, and an MBA, with honors, from Columbia Business School.