Founders don’t get derailed by BAD advice…

(most are too clever for that)

They get derailed by good advice used incorrectly… or at least misunderstood.

I see this all the time in my weekly AF office hours.

A founder shows up and says something like, “So-and-so told me I should do this,” or “I read on Twitter that X, Y, and Z is the best way to approach this.” On the surface, what they’re repeating usually sounds reasonable. Smart, even.

What’s painful is that in most cases the advice isn’t wrong.

What’s missing are the subtleties around when it applies, why it works, and WHAT NEEDS TO BE TRUE (so important) in their situation for it to actually help.

So in this essay, I want to break down three common bits of fundraising advice that founders misunderstand consistently. I’ll do more of these in the future, but let’s start here.

1. “Cold emailing VCs works”

This line gets thrown around a lot.

You’ll hear founders casually mention, “Oh, one of our investors came in from a cold email,” as if that’s replicable for everyone. What’s almost never discussed is what that email actually said or what kind of momentum and credibility that founder had when they sent it.

When cold email works, it usually falls into one of two buckets.

Bucket one: there’s already heavy gravity around you.

The email sounds like:

“I’m a second-time founder who sold my last company for $100M+, now I’m building X…”

or

“We’ve just signed five enterprise customers on six-figure contracts, churn is low, here’s what’s happening and why it’s interesting right now…”

If you have that level of signal, the cold email isn’t doing some magical job. The signal is doing the work. The email is just the delivery vehicle.

In that situation, yes, cold email “works,” but it’s working because you’re already in rare air. Investors are wired to pay attention when they see certain phrases, numbers, or logos. The story travels almost no matter how you send it.

Bucket two: you have a very specific, sharp insight in a niche a VC already cares about.

This is a “threading the needle” version of cold outreach. You’re working on a narrow problem in a narrow space, and your email contains an insight that would catch the attention of someone who has been quietly obsessing over that exact corner of the world.

Here, cold email can work, but this is where it’s so important to realize… it’s a volume play. You’re throwing up a lot of shots in the dark in the hopes of hitting that one person who sees your note and thinks, “Finally, someone is working on this.”

⭐️SUPER IMPORTANT ADVICE FOR THIS TO WORK⭐️ → Ok so i’ve acknowledged that this cold email strategy could work for an average founder.  BUT for that to even have a chance, the email has to be short enough and clear enough that if they skim it in two seconds, the insight lands. No long backstory. No walls of text. Just enough to make a curious person stop and think.

So yes, cold email is real. It’s not a myth.

But most founders are not in bucket one, and most are not operating like bucket two either. They’re somewhere in the middle, with some promise, some traction, but nothing so obvious that a stranger will fight to reply after reading a cold note in between partner meetings.

That’s why my advice is usually this:

Cold email should always be part of your fundraise… it just shouldn’t be the majority of your outreach. The energy you pour into scraping every email address you can find and blasting generic messages is almost always better spent lining up warm introductions, tightening your story, and creating more signal that makes any outreach more effective.

2. “Show a big TAM”

This feels like one of the Ten Commandments of fundraising.  Something you just assume is necessary because everyone talks about it like it’s etched in some uneditable stone tablet.

Founders have been led to believe that a “real” deck must include a big TAM slide, and often the full TAM/SAM/SOM treatment. For clarity, that’s:

• TAM: Total Addressable Market
• SAM: Serviceable Available Market
• SOM: Serviceable Obtainable Market

Here’s a slightly controversial take… I think this slide should be removed from all early stage venture slides.  Crazy, I know but here’s why…

I believe the TAM obsession is basically a leftover from the predecessors to what we know as early stage venture investing today.

If you look at earlier eras of investing in private companies, people were raising money for large, established companies. Businesses with years of financial history, mature sales motions, and clear markets. In those situations, it made a ton of sense to ask, “If this keeps going the way it’s going, how big can this get?” The TAM slide was a way of extending a line that already existed.

Then, slowly, investors started moving towards investing in earlier stage competition.

Less competition, more upside, more chances to get in before everyone else. The market created seed rounds. Then pre-seed rounds (a round that literally didn’t exist ten years ago btw).

But as timing of investors moved earlier, the elements used in fundraising decks didn’t evolve. The TAM slide survived the migration. What started as a tool for already-working businesses got dragged all the way to idea-stage companies with almost no data behind them.

That’s how you end up with a pre-seed deck that says, “$100B is spent on X… if we get just one percent of that, we’re a unicorn.” It’s not that the number is false. It’s that the story from today to that number is completely hand-wavy.

At the earliest stages, investors aren’t actually comforted by a giant number pulled from a consulting report. They want to understand:

• What specific problem are you solving right now?
• For whom?
• Why do they care enough to buy or use it?
• And if this keeps working, can it logically expand into something big?

That last part is where “market size” still matters. There has to be a big opportunity out there somewhere. But the way you express that doesn’t have to be a traditional TAM/SAM/SOM slide. In fact…it shouldn’t be. In most decks I see, that slide is either miscalculated, overly aggressive, or just a distraction from the real story.

A more useful approach looks like:

• Here is the narrow market we’re attacking first, with some believable math on why that’s attractive on its own.
• Here’s how success in that initial wedge opens doors to adjacent use cases, geographies, or buyer personas.
• When you mentally roll those out, you can see how this gets very big without me needing to throw a random “$87B market” number at you.

Investors do want to feel like your vector points toward a large opportunity. They just don’t need you to cosplay as a late-stage company with a private-equity style deck when you’re still in the “we’re talking to early users and shipping product every week” phase.

So yes, communicate that you’re pointed at something big.

No, you don’t have to (and shouldn’t) include a TAM slide to do it.

3. “Share your vision”

“Share your vision” sounds like harmless, feel-good advice.

The problem is in practice, this advice often leads founders straight into bad storytelling.

What many hear is, “You need a big, sweeping narrative about how your company changes everything,” even if they don’t actually feel that way and don’t have any evidence to back it up yet. So they start inventing a future that doesn’t match their true ambition or the current version of reality.

The result is a pitch that sounds overcooked and fragile.

Easy to poke holes in. Easy to dismiss.

I think it helps to ground what “vision” really is. A real vision is not just a big future headline. It’s a mix of:

• a meaningful opportunity that exists out in front of you
• some personal pull toward that problem or space
• the sense that you’ll keep pulling on threads even when it’s hard
• early signals that people want what you’re already doing

Vision is about direction and commitment, not just scale.

There’s a big difference between:

“We’re going to be a $10B company and own this whole market.”

and

“I’m obsessed with this problem. The initial product we’re shipping already has a long list of customer needs we haven’t even touched yet. I can see a path where doing a great job here unlocks more and more surface area to build on.”

The first one is loud.

The second one is believable.

Where founders really get into trouble is when they’re told “VCs need to see a big vision” and, deep down, they don’t actually want to build that kind of company. They want a healthy, meaningful business, not a rocketship. There’s nothing wrong with that… it just doesn’t line up with what most venture investors are optimizing for.

So they bolt on a fake “big vision” to satisfy what they think they’re supposed to say. Investors can feel that mismatch. The story sounds off because it is off.

If your genuine vision is to build something smaller and more contained, that’s useful information. It might be telling you that venture capital isn’t the right fit, and that’s better to recognize early rather than late.

So yes, share your vision. But let it be grounded in who you are, what you’ve learned so far, and what you’re actually committed to doing… not just the biggest number you think sounds impressive.

Let’s recap …

These three ideas…

• cold emailing VCs works
• investors need to see a big TAM
• you have to “share your vision”

…are not bad advice in themselves. They’ve all been true, in context, for certain founders at certain moments.

The problem is when they get repeated as rules to follow without any understanding of why they exist or when they really help.

If you want to get better at fundraising, don’t just collect more advice.

Evolve your understanding via advice you hear.

Ask where a piece of advice came from. Ask what stage it applied to, what kind of founder it was meant for, and what needed to be true for it to work. Then look honestly at your own situation and decide if you’re actually in that bucket.

I’ll keep breaking down more of these in future essays. There are a lot.  Holler if there are any that you want me to tackle next!

Be chased,
Jason