What I Learned Crafting Messaging for 15 Startups

One morning in 2013, my wife suggested I quit my job and start the business I was always talking about — helping entrepreneurs tell their stories.

“It’ll never work,” I said. “Founders don’t budget a line item for storytelling.”

That same day, an investor friend of mine — who knew about my past life as a magazine journalist — emailed to ask if I could help one of his startups better tell their story — on their home page, to investors, to customers, and to potential new hires. Except that’s not how he put it.

“We need strategic messaging and positioning guidance,” he wrote.

Two years later, I make my living “crafting strategic messaging and positioning” for early-stage companies. Recently, I delivered strategic messaging assets to my 15th client company, so this seemed like a good moment to reflect and share a few lessons learned.

If you’re thinking about high-level company and product messages — that is, stories — I hope you’ll find these five points useful.

#1: Conversations about messaging are really conversations about strategy.

Great messaging makes an audience envision two possible futures: one positive (achieved through purchasing, signing up, or otherwise engaging), the other negative (the result of not buying, or choosing a competitor). So you have to make clear choices about who your audience is, what the future you’re promising them looks like, and how you’ll credibly make it come true. As Andreessen Horowitz’s Ben Horowitz says, “The company story is the company strategy.”

#2: The hardest thing about messaging is leaving things out.

You know those people who, on a first date, attempt to win you over by listing every one of their selling points? That’s how some companies approach messaging. Of course, great editors will tell you that compelling stories are the result of figuring out what’s important and cutting the rest. One of my clients had been touting its charitable donations above all else, but even the founders admitted that few customers cared primarily about that. A big part of my job is helping leaders come to terms with de-prioritizing parts of their story — sometimes parts that they love — in service of becoming more effective.

#3: Strategic messaging matters for recruiting.

From the beginning, I’ve described the future that I offer to my own clients as “telling more effective stories to customers, investors, and potential new hires.” I’ve always believed in the “new hires” part, but recently a well-funded Series B company with A-list investors engaged me solely to build strategic messaging for its engineering team. As the CEO told me, “The only way we achieve our mission is if we hire the best engineers, so that means communicating more about our team than just a few pics of them playing ping pong.” I love that, and I predict more companies will invest in strategic messaging that’s specifically geared to improve recruiting.

#4: Differentiation can become a distraction.

Yes, differentiation is crucial. However, prospects have to understand what you do before they’re ready to learn how you do it differently. One of my clients, not wanting to seem like all the other companies that do X, didn’t even mention X on its home page. Prospects would literally call the sales team and say, “I thought you guys did X, but guess I was wrong. Can you refer me to companies that do X?”

#5: Storytelling is hard, but more teams are seeing the value.

I started my career as a programmer, and if you hired me today as your Rails guy, you could do worse. I used to think messaging was easier than coding, but after doing it so many times, I now believe the opposite. When your code’s not working, there’s usually a pretty clear path to finding out why. When your story’s not working, it’s a less-structured journey. Still, it’s reassuring to see that more and more companies are seeing value in finding a line item for it, even if it goes by other names.

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About Andy Raskin:
I help leadership teams craft strategic messaging and positioning — for fundraising, sales, marketing, and recruiting. My clients include companies backed by Andreessen Horowitz, KPCB, First Round Capital and other top-tier investors. I also lead storytelling workshops for teams. More at
http://andyraskin.com.