For Startups, the Power of “Why Now”

You’ve defined your target customer. You’ve explained why his or her life is hard without you, and why your product is going to make things better.

Yet investors remain skeptical, potential customers unsigned.

What’s going on?

One possibility, based on what I’m seeing in my strategic messaging and positioning engagements, is that you’re missing a crucial element of narrative storytelling. It’s an element that all great presenters, from Steve Jobs to Elon Musk — indeed, all great storytellers throughout history — use to inject their stories with an urgency that grabs audiences.

And while it’s hugely important, it can be difficult to execute well.

The power of “Why now” in storytelling

Whether you’re building strategic messaging or an investor pitch, you’re telling a story. And in every successful story, something happens that prods the hero into action. A sandstorm forces him to survive alone on Mars (The Martian), her best friend taps her to be maid of honor (Bridesmaids), or her sister buries the entire kingdom under a sheet of ice (Frozen).

Yet, like potential customers searching for excuses not to sign your contract, heroes are sometimes reluctant. For example, when we first meet Luke Skywalker in Star Wars, he’s whining about how much he craves adventure. So when Obi Wan proposes a mission to rescue Princess Leah on the planet Alderaan, we expect Luke to jump at the chance. Instead, he demurs:

LUKE: Alderaan? Hmm, I’m not going to Alderaan. I’ve got to get home. It’s late…
OBI WAN: I need your help, Luke. She needs your help. I’m getting too old for this kind of thing.
LUKE: Listen, I can’t get involved. I’ve got work to do. It’s not like I like the Empire — I hate it. But there’s nothing I can do about it right now. It’s also such a long way from here.

Cultural historian and storytelling theorist Joseph Campbell famously dubbed this pattern “Refusal of the Call,” and George Lucas (who openly credits Campbell’s influence) exploited it to perfection. When Luke does finally “buy” —accompanying Obi Wan to Alderaan —it’s only after the Empire destroys Luke’s home, kills his aunt and uncle, and leaves him with nothing. In other words, the audience knows not only why Luke wants to act, but why he has to act now.

The 3 kinds of startup why-nows

For better or worse, most of us won’t be targeting such desperate customers. Still, the degree to which you can explain what has changed in the world so that your customer not only wants the future you’re promising but actually needs it now, the more credible your strategic story will be — to investors, potential hires, and customers themselves.

Of course, your first impulse will be to answer “Why now?” with some version of “Because our product is really great.” That’s sub-optimal for many reasons that I hope are obvious, not least of which is that it doesn’t speak at all to customer needs.

In general, I classify effective “why-nows” into three categories: demand, qualification, and supply.

1) Demand why-nows

Demand why-nows are recent shifts in the customer’s external world that increase the need for what you’re offering. For example, changing attitudes about work among millenials might increase demand for new kinds of HR training programs.

Demand why-nows are ideal for investor pitches and strategic messaging because they explain how recent trends create a larger total addressable market (TAM). Demand-side why-nows can include:

  • Changes in societal norms, preferences, or behaviors, including new uses of technology
  • Shifts in population demographics
  • Shifts in your customer’s industry dynamics (especially ones that reduce profitability of the status quo)
  • Changes in your customer’s competitive landscape (including recent, widespread disappointment with competitor products)
  • Regulatory changes that spur demand for your offering

2) Qualification why-nows

Qualification why-nows are personal or organizational changes internal to your customer that make buying more likely. For example, if you’re selling to businesses, companies may only need your services once they reach a threshold number of employees. In my own work, CEOs tend to engage me when the stakes around telling a great story get higher, like when they’re going out for funding or are about to scale their team.

Qualification why-nows can be combined with demand why-nows to establish market size. For example, if you sell a service that people need when they retire (qualification why-now), you could point to the impending increase in over-65 population (demand why-now) to make a credible case for a growing opportunity.

Also, as the name implies, qualification why-nows are great for identifying high-value prospects. That’s because they describe changes to personal (if you’re B2C) or organizational (B2B) attributes— such as age, size, geographic distribution, strategy, etc. — that you can flag through data analysis.

3) Supply why-nows

Supply why-nows are recent developments that make your solution possible, more affordable, or more profitable. A great example is the range of products that have been made possible (and/or cheap) by cloud infrastructure. Other supply why-nows include:

  • Newly available technologies or data
  • Changes in the economics of supply, production or distribution
  • Regulatory changes that make it possible to deliver your offering
  • Changes in your competitive landscape

Supply why-nows are most powerful when combined with demand why-nows. For example, if advertisers are under pressure to more profitably acquire customers (demand why-now), then newly available big data analysis tools (supply why-now) make the case for a new breed of programmatic ad buying services.

Where to look for your why-nows

In my work with leadership teams, I’ve found the following to be fertile ground for why-now harvesting:

Customers and prospects

If you have customers, by all means ask them why they were in the market for your product or service in the first place. If you don’t, talk to prospects who have indicated interest and ask them the same question. Write down exactly what they tell you, and look for common threads.

Sales teams

Salespeople usually have a great sense about why a customer converts from a whining Luke prospect into a committed Jedi buyer. Sometimes they understand the motivations behind that conversion even better than customers do.

Product teams

If you’re big enough to have a product team, they may know of new technologies or data (supply why-nows) that make your offering possible or more affordable. Like salespeople, they may also have a great sense of what’s happening in your customer’s world to make buying more urgent (demand why-nows).


Scanning your customer database for attributes that buyers have in common can yield surprisingly valuable qualification why-nows. (I once found that Klout score was a decent predictor of purchase.) Likewise, industry and trend data is a great place to uncover powerful why-nows.

“Why now” inspiration: 3 master storytellers doing it well

Still not sure about your why-now? Check out these examples of master storytellers making effective use of why-nows:

Elon Musk pitching the Tesla Powerwall:

If we do nothing, [CO2 concentration in the atmosphere is] headed to levels that we don’t even see in the fossil record.

Steve Jobs pitching the first iMac:

We are targeting this to the #1 use consumers tell us they’re looking for, which is to get on the Internet — simply and fast.

Dr. Martin Luther King, Jr. pitching racial equality (the “I Have a Dream” speech):

We have also come to this hallowed spot to remind America of the fierce urgency of Now.

Thanks to Asana’s Vivek Sri, who inspired this piece by approaching me after my recent General Assembly workshop and asking how best to answer “Why now?” If you have a question about strategic messaging, investor pitching, or business storytelling, email me ( and I’ll answer it in a future post.

About Andy Raskin:
I help entrepreneurs tell better strategic stories — for fundraising, marketing, recruiting and sales — and my clients include leadership teams funded by Andreessen Horowitz, True Ventures, First Round Capital, and other top venture investors. I also lead workshops on strategic storytelling and content strategy. To learn more or get in touch, visit Or follow me on Twitter: @araskin