Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

It’s Zuora’s, and it’s brilliant. Here’s why.

My friend Tim got a sales position at a Series-C software company that garnered $60 million from A-list investors. He's one of the best salespeople I know, yet he emailed me after starting to struggle.

Tim has a few modest clients. “Big companies ignore my pitch”. Tim said.

I love helping teams write the strategic story that drives sales, marketing, and fundraising. Tim and I had lunch at Amber India on Market Street to evaluate his deck.

After a feast, I asked Tim when prospects tune out.

He said, “several slides in”.

Intent on maximizing dining ROI, Tim went back to the buffet for seconds. When he returned, I pulled out my laptop and launched into a Powerpoint presentation.

“What’s this?” Tim asked.

“This,” I said, “is the greatest sales deck I have ever seen.”

Five Essentials of a Great Sales Narrative

I showed Tim a sales slide from IPO-bound Zuora, which sells a SaaS platform for subscription billing. Zuora supports recurring payments (e.g. enterprise software).

Ex-Zuora salesman gave me the deck, saying it helped him close his largest business. (I don't know anyone who works at Zuora.) After reading this, a few Zuora employees contacted me.)

Tim abandoned his naan in a pool of goat curry and took notes while we discussed the Zuora deck.

We remarked how well the deck led prospects through five elements:

(The ex-Zuora salesperson begged me not to release the Zuora deck publicly.) All of the images below originate from Zuora's website and SlideShare channel.)

#1. Name a Significant Change in the World

Don't start a sales presentation with mentioning your product, headquarters, investors, clients, or yourself.

Name the world shift that raises enormous stakes and urgency for your prospect.

Every Zuora sales deck begins with this slide:

Zuora coined the term subscription economy to describe a new market where purchasers prefer regular service payments over outright purchases. Zuora then shows a slide with the change's history.

Most pitch recommendation advises starting with the problem. When you claim a problem, you put prospects on the defensive. They may be unaware of or uncomfortable admitting the situation.

When you highlight a global trend, prospects open up about how it affects them, worries them, and where they see opportunity. You capture their interest. Robert McKee says:

…what attracts human attention is change. …if the temperature around you changes, if the phone rings — that gets your attention. The way in which a story begins is a starting event that creates a moment of change.

#2. Show There’ll Be Winners and Losers

Loss aversion affects all prospects. They avoid a loss by sticking with the status quo rather than risking a gain by changing.

To fight loss aversion, show how the change will create winners and losers. You must show both

1. that if the prospect can adjust to the modification you mentioned, the outcome will probably be quite favorable; and

2. That failing to do so is likely to have an unacceptable negative impact on the prospect's future

Zuora shows a mass extinction among Fortune 500 firms.

…and then showing how the “winners” have shifted from product ownership to subscription services. Those include upstarts…

…as well as rejuvenated incumbents:

To illustrate, Zuora asks:

Winners utilize Zuora's subscription service models.

#3. Tease the Promised Land

It's tempting to get into product or service details now. Resist that urge.

Prospects won't understand why product/service details are crucial if you introduce them too soon, therefore they'll tune out.

Instead, providing a teaser image of the happily-ever-after your product/service will assist the prospect reach.

Your Promised Land should be appealing and hard to achieve without support. Otherwise, why does your company exist?

Zuora shows this Promised Land slide after explaining that the subscription economy will have winners and losers.

Not your product or service, but a new future state.

(I asked my friend Tim to describe his Promised Land, and he answered, "You’ll have the most innovative platform for ____." Nope: the Promised Land isn't possessing your technology, but living with it.)

Your Promised Land helps prospects market your solution to coworkers after your sales meeting. Your coworkers will wonder what you do without you. Your prospects are more likely to provide a persuasive answer with a captivating Promised Land.

#4. Present Features as “Mystic Gifts” for Overcoming Difficulties on the Road to the Promised Land

Successful sales decks follow the same format as epic films and fairy tales. Obi Wan gives Luke a lightsaber to help him destroy the Empire. You're Gandalf, helping Frodo destroy the ring. Your prospect is Cinderella, and you're her fairy godmother.

Position your product or service's skills as mystical gifts to aid your main character (prospect) achieve the Promised Land.

Zuora's client record slide is shown above. Without context, even the most technical prospect would be bored.

Positioned in the context of shifting from an “old” to a “new world”, it's the foundation for a compelling conversation with prospects—technical and otherwise—about why traditional solutions can't reach the Promised Land.

#5. Show Proof That You Can Make the Story True.

In this sense, you're promising possibilities that if they follow you, they'll reach the Promised Land.

The journey to the Promised Land is by definition rocky, so prospects are right to be cautious. The final part of the pitch is proof that you can make the story come true.

The most convincing proof is a success story about how you assisted someone comparable to the prospect. Zuora's sales people use a deck of customer success stories, but this one gets the essence.

I particularly appreciate this one from an NCR exec (a Zuora customer), which relates more strongly to Zuora's Promised Land:

Not enough successful customers? Product demos are the next best evidence, but features should always be presented in the context of helping a prospect achieve the Promised Land.

The best sales narrative is one that is told by everyone.

Success rarely comes from a fantastic deck alone. To be effective, salespeople need an organization-wide story about change, Promised Land, and Magic Gifts.

Zuora exemplifies this. If you hear a Zuora executive, including CEO Tien Tzuo, talk, you'll likely hear about the subscription economy and its winners and losers. This is the theme of the company's marketing communications, campaigns, and vision statement.

According to the ex-Zuora salesperson, company-wide story alignment made him successful.

The Zuora marketing folks ran campaigns and branding around this shift to the subscription economy, and [CEO] Tien [Tzuo] talked it up all the time. All of that was like air cover for my in-person sales ground attack. By the time I arrived, prospects were already convinced they had to act. It was the closest thing I’ve ever experienced to sales nirvana.

The largest deal ever

Tim contacted me three weeks after our lunch to tell me that prospects at large organizations were responding well to his new deck, which we modeled on Zuora's framework. First, prospects revealed their obstacles more quickly. The new pitch engages CFOs and other top gatekeepers better, he said.

A week later, Tim emailed that he'd signed his company's biggest agreement.

Next week, we’re headed back to Amber India to celebrate.

How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.

Orion's red supergiant Betelgeuse erupted. This is astronomers' most magnificent occurrence.

Betelgeuse, a supergiant star in Orion, garnered attention in 2019 for its peculiar appearance. It continued to dim in 2020.

The star was previously thought to explode as a supernova. Studying the event has revealed what happened to Betelgeuse since it happened.

Astronomers saw that the star released a large amount of material, causing it to lose a section of its surface.

They have never seen anything like this and are unsure what caused the star to release so much material.

According to Harvard-Smithsonian Center for Astrophysics astrophysicist Andrea Dupre, astronomers' data reveals an unexplained mystery.

They say it's a new technique to examine star evolution. The James Webb telescope revealed the star's surface features.

Corona flares are stellar mass ejections. These eruptions change the Sun's outer atmosphere.

This could affect power grids and satellite communications if it hits Earth.

Betelgeuse's flare ejected four times more material than the Sun's corona flare.

Astronomers have monitored star rhythms for 50 years. They've seen its dimming and brightening cycle start, stop, and repeat.

Monitoring Betelgeuse's pulse revealed the eruption's power.

Dupre believes the star's convection cells are still amplifying the blast's effects, comparing it to an imbalanced washing machine tub.

The star's outer layer has returned to normal, Hubble data shows. The photosphere slowly rebuilds its springy surface.

Dupre noted the star's unusual behavior. For instance, it’s causing its interior to bounce.

This suggests that the mass ejections that caused the star's surface to lose mass were two separate processes.

Researchers hope to better understand star mass ejection with the James Webb Space Telescope.

I've been pondering product strategy and how to articulate it. Frameworks helped guide our thinking.

If your teams aren't working together or there's no clear path to victory, your product strategy may not be well-articulated or communicated (if you have one).

Before diving into a product strategy's details, it's important to understand its role in the bigger picture — the pieces that move your organization forward.

the overall picture

A product strategy is crucial, in my opinion. It's part of a successful product or business. It's the showpiece.

To simplify, we'll discuss four main components:

1. Vision

2. Product Management

3. Goals

4. Roadmap

Vision

Your company's mission? Your company/product in 35 years? Which headlines?

The vision defines everything your organization will do in the long term. It shows how your company impacted the world. It's your organization's rallying cry.

An ambitious but realistic vision is needed.

Without a clear vision, your product strategy may be inconsistent.

Product Management

Our main subject. Product strategy connects everything. It fulfills the vision.

In Part 2, we'll discuss product strategy.

Goals

This component can be goals, objectives, key results, targets, milestones, or whatever goal-tracking framework works best for your organization.

These product strategy metrics will help your team prioritize strategies and roadmaps.

Your company's goals should be unified. This fuels success.

Roadmap

The roadmap is your product strategy's timeline. It provides a prioritized view of your team's upcoming deliverables.

A roadmap is time-bound and includes measurable goals for your company. Your team's steps and capabilities for executing product strategy.

If your team has trouble prioritizing or defining a roadmap, your product strategy or vision is likely unclear.

Formulation of a Product Strategy

Now that we've discussed where your product strategy fits in the big picture, let's look at a framework.

A product strategy should include challenges, an approach, and actions.

Challenges

First, analyze the problems/situations you're solving. It can be customer- or company-focused.

The analysis should explain the problems and why they're important. Try to simplify the situation and identify critical aspects.

Some questions:

• What issues are we attempting to resolve?

• What obstacles—internal or otherwise—are we attempting to overcome?

• What is the opportunity, and why should we pursue it, in your opinion?

Decided Method

Second, describe your approach. This can be a set of company policies for handling the challenge. It's the overall approach to the first part's analysis.

The approach can be your company's bets, the solutions you've found, or how you'll solve the problems you've identified.

Again, these questions can help:

• What is the value that we hope to offer to our clients?

• Which market are we focusing on first?

• What makes us stand out? Our benefit over rivals?

Actions

Third, identify actions that result from your approach. Second-part actions should be these.

Coordinate these actions. You may need to add products or features to your roadmap, acquire new capabilities through partnerships, or launch new marketing campaigns. Whatever fits your challenges and strategy.

Final questions:

• What skills do we need to develop or obtain?

• What is the chosen remedy? What are the main outputs?

• What else ought to be added to our road map?

Put everything together

… and iterate!

Strategy isn't one-and-done. Changes occur. Economies change. Competitors emerge. Customer expectations change.

One unexpected event can make strategies obsolete quickly. Muscle it. Review, evaluate, and course-correct your strategies with your teams. Quarterly works. In a new or unstable industry, more often.