Most fundraising advice focuses on tactics.

How to build a deck.
How to email investors.
How to negotiate a term sheet.

But if you listen carefully to how experienced investors think, the pattern is different.

They’re not reacting to tactics. They’re reacting to signals.

Andrew Ackerman has seen this play out across hundreds of startups. And the consistent takeaway is simple:

The outcome of your fundraise is largely determined before you start it.

1. Your Pitch Is Just a Compression of Your Business

A lot of founders treat the pitch deck like a marketing asset.

Something you refine, polish, and iterate on until it “sounds right.”

According to Andrew, that’s not how investors see it.

They see it as a compressed version of your company. Every slide is a claim. And every claim needs to hold up.

Andrew puts it in a way that’s hard to ignore: “Your startup is like a chain. If any one link is weak, the chain fails.”

This changes how you approach the deck entirely.

You don’t start by asking:
What story do I want to tell?

You start by asking:
What would make this company undeniable?

That leads to better questions:

• Is this problem actually painful and frequent?
• Is the market big enough without mental gymnastics?
• Does this model make sense at scale?
• Are we the right people to do this?

If those answers are weak, no amount of storytelling fixes it.

The best decks feel simple because the underlying business is clear.

2. Most Founders Overcomplicate the Wrong Things

When founders try to “sound like startups,” they often make things worse.

Market sizing is the clearest example.

Instead of clarity, you get layered frameworks, inflated numbers, and vague logic. Andrew’s take is blunt: “If you give me three numbers, I know at least two of them are wrong.”

The irony is that investors are not looking for sophistication here. They’re looking for sanity.

Can you explain your market in a way that makes immediate sense?

• Who is the buyer?
• What do they pay?
• How many of them exist?

That’s enough to start a real dialog.

The same applies to other parts of the deck.

Founders try to impress with complexity when what actually builds confidence is clarity.

If someone has to work hard to understand your business, they usually won’t.

3. The “Ask” Is Where Strategic Thinking Shows Up

One of the fastest ways to tell how well a founder understands fundraising is to look at their ask.

Most founders can answer how much they’re raising.

Far fewer can answer what that capital actually achieves.

Andrew breaks it down into a simple structure:

• What are you raising?
• What milestone does it get you to?
• How long will it take?

That second question is where things fall apart.

If your round doesn’t clearly move the company to a meaningful next stage, you’re creating problems for your future self. Andrew’s analogy is sharp:

“No one wants to put half a tank of gas in a rocket ship.”

You either reach orbit or you don’t.

This is where better founders stand out.

They don’t just think about raising capital. They think about sequencing:

• What does this round unlock?
• What does that unlock next?
• Who would fund that next step?

When that logic is clear, the ask becomes much more compelling.

4. Fundraising Is a Distribution Problem

A strong pitch doesn’t matter if it never reaches the right investors.

This is where a lot of founders underestimate the process.

They build a solid deck, create a list of investors, and start sending emails. When responses are low, they assume the pitch is the problem.

Often, it isn’t.

It’s how they’re getting in front of people.

Andrew is very direct about this. Warm introductions don’t just help, “they prioritize your startup over everything else.”

That prioritization is everything.

Investors are not sitting around waiting for new deals. They are overloaded with inbound deals, and filtering constantly (often using AI now). A warm intro boosts you above the considerable noise. 

Cold outreach, especially at scale, tends to fail for a simple reason.

It asks the investor to do all the work:

• Understand your company
• Decide if it’s relevant
• Figure out if it’s worth their time

Good founders don’t outsource that thinking.

They do the work upfront:

• Identify investors who are actually a fit
• Understand what those investors care about
• Find credible paths to reach them

It’s slower. But it works.

5. Targeting the Right Investors Is a Skill

Another subtle mistake founders make is treating investors as a generic group.

Andrew suggests a simple test. You should be able to say:

This investor backed companies A, B, and C. Our company fits that pattern.

If you can’t make that connection, you’re guessing.

And when you guess, two things happen:

• You waste time talking to the wrong people
• You signal to investors that you haven’t done your homework

Strong founders approach this more like sales.

They narrow the list. They qualify leads. They tailor outreach.

Doing just these 3 changes the final outcome significantly. 

6. Closing a Round Is Where Things Get Real

Getting investor interest is one phase. Closing is another entirely.

This is where many founders get caught off guard.

The moment you receive a term sheet, everything speeds up.

Now you’re managing:

• Timelines
• Competing interest
• Communication across multiple parties

Andrew points out that this window is critical. It’s your opportunity to bring other investors off the fence and improve your position.

At the same time, it requires discipline.

You need to:

• Move quickly without rushing decisions
• Create urgency (and maybe some FOMO) without losing control
• Keep the process organized as complexity increases

And most importantly, remember this:

A signed term sheet is not the finish line.

The round is only real when the money is in the bank.

Final Thought

What stands out across all of this is not a specific tactic.

It’s how experienced founders think about the process.

They don’t treat fundraising as a separate activity layered on top of the business.

They design the business in a way that makes fundraising make sense.

That shows up in:

• Clear assumptions
• Right sequencing
• Outreach driven by warm intros

The difference compounds quickly.

And over time, it’s usually what separates a difficult raise from a smooth one.

This article is based on an episode of the How I Raised It podcast, a behind-the-scenes look at how startup founders and fund managers raise money.