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.

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.

During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

Full article is available here

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Calmness is a vital life skill.

It aids communication. It boosts creativity and performance.

I've studied calm people's habits for years. Commonalities:

Have mastered the art of self-humor.

Protectors take their job seriously, draining the room's energy.

They are fixated on positive pursuits like making cool things, building a strong physique, and having fun with others rather than on depressing influences like the news and gossip.

Every day, spend at least 20 minutes moving, whether it's walking, yoga, or lifting weights.

Discover ways to take pleasure in life's challenges.

Since perspective is malleable, they change their view.

Set your own needs first.

Stressed people neglect themselves and wonder why they struggle.

Prioritize self-care.

Don't ruin your life to please others.

Make something.

Calm people create more than react.

They love creating beautiful things—paintings, children, relationships, and projects.

Don’t hold their breath.

If you're stressed or angry, you may be surprised how much time you spend holding your breath and tightening your belly.

Release, breathe, and relax to find calm.

Stopped rushing.

Rushing is disadvantageous.

Calm people handle life better.

Are aware of their own dietary requirements.

They avoid junk food and eat foods that keep them healthy, happy, and calm.

Don’t take anything personally.

Stressed people control everything.

Self-conscious.

Calm people put others and their work first.

Keep their surroundings neat.

Maintaining an uplifting and clutter-free environment daily calms the mind.

Minimise negative people.

Calm people are ruthless with their boundaries and avoid negative and drama-prone people.

Homeownership isn't the only life pattern.

Want to irritate people?

My party trick is to say I used to own a house but no longer do.

I no longer wish to own a home, not because I lost it or because I'm moving.

It was a long-term plan. It was more deliberate than buying a home. Many people are committed for this reason.

Poppycock.

Anyone who told me that owning a house (or striving to do so) is a must is wrong.

Because, URGH.

One pattern for life is to own a home, but there are millions of others.

You can afford to buy a home? Go, buddy.

You think you need 1,000 square feet (or more)? You think it's non-negotiable in life?

Nope.

It's insane that society forces everyone to own real estate, regardless of income, wants, requirements, or situation. As if this trade brings happiness, stability, and contentment.

Take it from someone who thought this for years: drywall isn't happy. Living your way brings contentment.

That's in real estate. It may also be renting a small apartment in a city that makes your soul sing, but you can't afford the downpayment or mortgage payments.

Living or traveling abroad is difficult when your life savings are connected to something that eats your money the moment you sign.

#vanlife, which seems like torment to me, makes some people feel alive.

I've seen co-living, vacation rental after holiday rental, living with family, and more work.

Insisting that home ownership is the only path in life is foolish and reduces alternative options.

How little we question homeownership is a disgrace.

No one challenges a homebuyer's motives. We congratulate them, then that's it.

When you offload one, you must answer every question, even if you have a loose screw.

• Why do you want to sell?

• Do you have any concerns about leaving the market?

• Why would you want to renounce what everyone strives for?

• Why would you want to abandon a beautiful place like that?

• Why would you mismanage your cash in such a way?

• But surely it's only temporary? RIGHT??

Incorrect questions. Buying a property requires several inquiries.

• The typical American has $4500 saved up. When something goes wrong with the house (not if, it’s never if), can you actually afford the repairs?

• Are you certain that you can examine a home in less than 15 minutes before committing to buying it outright and promising to pay more than twice the asking price on a 30-year 7% mortgage?

• Are you certain you're ready to leave behind friends, family, and the services you depend on in order to acquire something?

• Have you thought about the connotation that moving to a suburb, which more than half of Americans do, means you will be dependent on a car for the rest of your life?

Plus:

Are you sure you want to prioritize home ownership over debt, employment, travel, raising kids, and daily routines?

Homeownership entails that. This ex-homeowner says it will rule your life from the time you put the key in the door.

This isn't questioned. We don't question enough. The holy home-ownership grail was set long ago, and we don't challenge it.

Many people question after signing the deeds. 70% of homeowners had at least one regret about buying a property, including the expense.

Exactly. Tragic.

Homes are different from houses

We've been fooled into thinking home ownership will make us happy.

Some may agree. No one.

Bricks and brick hindered me from living the version of my life that made me most comfortable, happy, and steady.

I'm spending the next month in a modest apartment in southern Spain. Even though it's late November, today will be 68 degrees. My spouse and I will soon meet his visiting parents. We'll visit a Sherry store. We'll eat, nap, walk, and drink Sherry. Writing. Jerez means flamenco.

That's my home. This is such a privilege. Living a fulfilling life brings me the contentment that buying a home never did.

I'm happy and comfortable knowing I can make almost all of my days good. Rejecting home ownership is partly to blame.

I'm broke like most folks. I had to choose between home ownership and comfort. I said, I didn't find them together.

Feeling at home trumps owning brick-and-mortar every day.

The following is the reality of what it's like to turn the American Dream around.

Leaving the housing market.

Sometimes I wish I owned a home.

I miss having my own yard and bed. My kitchen, cookbooks, and pizza oven are missed.

But I rarely do.

Someone else's life plan pushed home ownership on me. I'm grateful I figured it out at 35. Many take much longer, and some never understand homeownership stinks (for them).

It's confusing. People will think you're dumb or suicidal.

If you read what I write, you'll know. You'll realize that all you've done is choose to live intentionally. Find a home beyond four walls and a picket fence.

Miss? As I said, they're not home. If it were, a pizza oven, a good mattress, and a well-stocked kitchen would bring happiness.

No.

If you can afford a house and desire one, more power to you.

There are other ways to discover home. Find calm and happiness. For fun.

For it, look deeper than your home's foundation.