There Is No Such Thing as "One-Size-Fits-All" Advice for Raising

It's different for everyone. Here's how to know if and when you should raise.

July 11, 2022
min read

Hello to all founders, storytellers, and leaders.

Thanks for being here for the second edition of The Storyteller’s Playbook. I hope you enjoyed last week’s and shared it with a friend or two.

This week is all about why one-size-fits-all advice is a NONSTARTER for founders, especially in a down market. The truth is, it just doesn’t work and we’re going to explore why.

Plus a breakdown of why numbers only matter when delivered correctly ( involves storytelling).

Finally, I’ve also thrown in a couple of well-aged articles by Ben Horowitz and Andy Raskin, and a Tweet thread from Paul Graham echoing last week’s letter about the big win opportunities a down market brings—for the best of the best.

I’m glad you’re here. Read on, Chief Storytelling Officer.

— Robbie

DEEP DIVE: Why I Hard Pass on "One-Size-Fits-All" Advice

I said it on LinkedIn, and I’ll say it again: One-size-fits-all advice for founders is a recipe for disaster.

This is why I have such an issue with pitch decks. The one-size-fits-all advice saying that Step 1 in the fundraising process should be to create a pitch deck and send it to investors lacks all nuance. It’s a lazy way of teaching fundraising that shows that people didn’t want to put the time, energy, and effort into learning what great storytelling and speaking looks like.

But that’s a point for a different deep dive.

Building a startup isn’t easy. It takes grit, perseverance, and resilience. And the truth is, it looks different for everyone. That’s why I don’t give everyone the same advice.

Remember: Advice is different than a process or framework. I give founders processes and frameworks but then tailor them specifically to the founders’ needs. There’s no magic formula when it comes to fundraising. You don’t want to be a cook just following a cookbook. You want to be a Michelin-starred chef creating your own menu—with three stars, at that.

When a founder asks me whether or not they should wait to fundraise until the market is better, I ask them if they have a crystal ball that tells them when that’s going to happen. Their eyes always go big. Of course they don’t know when the market will improve, because nobody does.

Too many investors keep saying, “Wait until the market improves.” But I’m still waiting for any of them to say when that will be. Maybe it’s November. Maybe it’s November 2023. Who knows? And that’s the point. Great founders continue to fundraise and great companies have always been built in tough times.

The real questions you need to be asking are:

  1. How much runway do you currently have?
  2. What reactions do you get from potential investors when you talk about your startup now?
  3. How good at fundraising are you?

Your current runway

Looking at your current runway tells you, for one thing, how great your need to fundraise is. If you have less than nine months’ worth, you probably need to fundraise right away to stay in the clear for the future.

Expect the fundraising process right now to take longer than before. Think two to six months if you already have a solid investor and founder network to build what my friend Jason Yeh calls Calendar Density.

If you have more than 15 months of runway, on the other hand, you’re probably better off improving your execution and growing your business, which will lay the groundwork for your next fundraising round and further prove to investors that you and your business are ready for their investment.

If you’re in the middle . . . you could go either way. Look at your metrics and at questions 2 and 3, which we’re covering next.

Gauging investors’ reactions

Gauging reactions in casual conversation with investors gives you a good idea of how successful you’ll be if you try to fundraise immediately. You might be saying to yourself, “Well, Robbie, how would I know this since I’m not speaking to investors right now because we aren’t fundraising?” That’s the mistake.

You should always be speaking to investors—asking for “advice,” building relationships, updating them on your progress and sharing your story with them. Especially important is your founder origin story to build those new relationships. That’s a topic you can expect in a future edition of Storyteller’s Playbook.

Your fundraising skill

Lastly, if you’re really good at fundraising, it won’t take as long as if you’re, well, not so great at it—a difference of, say, one month or six months from start to raise. This is especially true with founders I work with because they’ve already raised at least a pre-seed round and, many times, a seed round. I also work with many multi-time founders. So they know if they are okay, good, great, or elite fundraisers.

If you’re a brand new founder, expect to not be great at the start. Fundraising is a skill to build.

There are a lot of factors that go into choosing when to fundraise—especially if the market is down. You need to know yourself, your startup, and where you fall on the spectrum of fundraising before you decide when to go for it.

Any founder I work with understands the nuance involved and doesn't ask for generic advice. They know I wouldn't give it to them anyways. I’ll ask about their strengths, their story, and their vision, and with them, I build frameworks that evolve as their businesses evolve.

This leads us to the topic of storytelling.

Over the past week I've spoken with a number of VCs about what they see as glaring weaknesses from their founders. Even with great numbers and metrics that should lead to a successful next round, founders are struggling. Logically this doesn't make sense. Until you understand one thing.

Numbers can mean anything.

The way numbers become powerful is how they are framed in the story. It's why Brene Brown says "stories are data with soul." Storytelling is the delivery mechanism that allows a person to make sense of the numbers.

If you walk outside and yell out your message that you want a person a thousand miles away to hear, it will fall far short. On the other hand, if you type that message in a text message and press send, the person can receive it.

Numbers are the same. They only work if they have the right delivery mechanism.

Making the numbers make sense inside of the story unlocks their full potential. On their own, they are open to interpretation. If packaged poorly, there will be misalignment. When done right, it can move even the toughest investor to a yes.

Over the next few years, storytelling with numbers will become even more powerful. With greater scrutiny on companies and their metrics, a founder and CEO must be able to convey a compelling story that highlights the numbers. Spinning a good tale won't be enough.

Painting the future by using numbers in your storytelling...

Now that's what I call a true Chief Storytelling Officer.

And if you need help, that's why I'm writing this Storyteller's Playbook.

(One great book to check out on this topic is Nancy Duarte's DataStory.)

RESOURCES for Founders and Storytellers

Check out this Tweet thread from Paul Graham about fundraising in a down market. You just might be the next Google, and you can bet there are investors out there who don’t want to miss out.

Who goes into a room full of elite athletes sharing a pasta meal the night before the NYC Marathon and tells them that carb-loading is pseudoscience guaranteed to ruin their race? A bold storyteller. This 2019 article from Andy Raskin holds true as ever: Attacking the status quo and renaming the game is the fastest way to get people’s attention and convince them that you are the expert they need.

In this must-read Future article, Ben Horowitz highlights the difference between a “peacetime CEO” and a “wartime CEO.” Where peaceful times bring expansion, innovation, and relatively threat-free growth, times of war require CEOs to buckle down, grind it out, and play strategically to fend off competitors and other macro-environmental threats such as market shifts, supply chain disruptions, and minuscule resources at the company’s disposal. For a wartime CEO, every single move counts—it’s life or death.


This past week, multiple people suggested the book Amazon Unbound by Brad Stone to me. I’ve learned when really smart and successful people are saying the same thing to me, I should listen. So I’ll be reading through that next week, and I’m sure I’ll have thoughts.

If you ever have something you think I should read, watch, or share with the other readers, please send them my way. And if you ever have questions, don’t hesitate to ask.

I’m glad you’re here with me, and I hope you’ll continue to read along. I want The Storyteller’s Playbook to be your go-to for fundraising, storytelling, and founder guidance.

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