Skip this if you don't want to discover why your lively, no-brainer pitch isn't making $10k a month.

You don't want to be repulsive as an entrepreneur or anyone else. Making friends, influencing people, and converting strangers into customers will be difficult if your words evoke disgust, distrust, or disrespect. You may be one of many entrepreneurs who do this obliviously and involuntarily.

I've had to master selling my skills to recruiters (to land 6-figure jobs on Wall Street), selling companies to buyers in M&A transactions, and selling my own companies' products to strangers-turned-customers. I probably committed every cardinal sin of sales repulsion before realizing it was me or my poor salesmanship strategy.

If you're launching a new business, frustrated by low conversion rates, or just curious if you're repelling customers, read on to identify (and avoid) the 6 fatal errors that can kill any sales pitch.

1. The first indication

So many people fumble before they even speak because they assume their role is to convince the buyer. In other words, they expect to pressure, arm-twist, and combat objections until they convert the buyer. Actuality, the approach stinks of disgust, and emotionally-aware buyers would feel "gross" immediately.

Instead of trying to persuade a customer to buy, ask questions that will lead them to do so on their own. When a customer discovers your product or service on their own, they need less outside persuasion. Why not position your offer in a way that leads customers to sell themselves on it?

2. A flawless performance

Are you memorizing a sales script, tweaking video testimonials, and expunging historical blemishes before hitting "publish" on your new campaign? If so, you may be hurting your conversion rate.

Perfection may be a step too far and cause prospects to mistrust your sincerity. Become a great conversationalist to boost your sales. Seriously. Being charismatic is hard without being genuine and showing a little vulnerability.

People like vulnerability, even if it dents your perfect facade. Show the customer's stuttering testimonial. Open up about your or your company's past mistakes (and how you've since improved). Make your sales pitch a two-way conversation. Let the customer talk about themselves to build rapport. Real people sell, not canned scripts and movie-trailer testimonials.

If marketing or sales calls feel like a performance, you may be doing something wrong or leaving money on the table.

3. Your greatest phobia

Three minutes into prospect talks, I'd start sweating. I was talking 100 miles per hour, covering as many bases as possible to avoid the ones I feared. I knew my then-offering was inadequate and my firm had fears I hadn't addressed. So I word-vomited facts, features, and everything else to avoid the customer's concerns.

Do my prospects know I'm insecure? Maybe not, but it added an unnecessary and unhelpful layer of paranoia that kept me stressed, rushed, and on edge instead of connecting with the prospect. Skirting around a company, product, or service's flaws or objections is a poor, temporary, lazy (and cowardly) decision.

How can you project confidence and trust if you're afraid? Before you make another sales call, face your shortcomings, weak points, and objections. Your company won't be everyone's cup of tea, but you should have answers to every question or objection. You should be your business's top spokesperson and defender.

4. The unintentional apologies

Have you ever begged for a sale? I'm going to say no, however you may be unknowingly emitting sorry, inferior, insecure energy.

Young founders, first-time entrepreneurs, and those with severe imposter syndrome may elevate their target customer. This is common when trying to get first customers for obvious reasons.

• Since you're truly new at this, you naturally lack experience.

• You don't have the self-confidence boost of thousands or hundreds of closed deals or satisfied client results to remind you that your good or service is worthwhile.

• Getting those initial few clients seems like the most difficult task, as if doing so will decide the fate of your company as a whole (it probably won't, and you shouldn't actually place that much emphasis on any one transaction).

Customers can smell fear, insecurity, and anxiety just like they can smell B.S. If you believe your product or service improves clients' lives, selling it should feel like a benevolent act of service, not a sleazy money-grab. If you're a sincere entrepreneur, prospects will believe your proposition; if you're apprehensive, they'll notice.

Approach every sale as if you're fine with or without it. This has improved my salesmanship, marketing skills, and mental health. When you put pressure on yourself to close a sale or convince a difficult prospect "or else" (your company will fail, your rent will be late, your electricity will be cut), you emit desperation and lower the quality of your pitch. There's no point.

5. The endless promises

We've all read a million times how to answer or disprove prospects' arguments and add extra incentives to speed or secure the close. Some objections shouldn't be refuted. What if I told you not to offer certain incentives, bonuses, and promises? What if I told you to walk away from some prospects, even if it means losing your sales goal?

If you market to enough people, make enough sales calls, or grow enough companies, you'll encounter prospects who can't be satisfied. These prospects have endless questions, concerns, and requests for more, more, more that you'll never satisfy. These people are a distraction, a resource drain, and a test of your ability to cut losses before they erode your sanity and profit margin.

To appease or convert these insatiably needy, greedy Nellies into customers, you may agree with or acquiesce to every request and demand — even if you can't follow through. Once you overpromise and answer every hole they poke, their trust in you may wane quickly.

Telling a prospect what you can't do takes courage and integrity. If you're honest, upfront, and willing to admit when a product or service isn't right for the customer, you'll gain respect and positive customer experiences. Sometimes honesty is the most refreshing pitch and the deal-closer.

6. No matter what

Have you ever said, "I'll do anything to close this sale"? If so, you've probably already been disqualified. If a prospective customer haggles over a price, requests a discount, or continues to wear you down after you've made three concessions too many, you have a metal hook in your mouth, not them, and it may not end well. Why?

If you're so willing to cut a deal that you cut prices, comp services, extend payment plans, waive fees, etc., you betray your own confidence that your product or service was worth the stated price. They wonder if anyone is paying those prices, if you've ever had a customer (who wasn't a blood relative), and if you're legitimate or worth your rates.

Once a prospect senses that you'll do whatever it takes to get them to buy, their suspicions rise and they wonder why.

• Why are you cutting pricing if something is wrong with you or your service?

• Why are you so desperate for their sale?

• Why aren't more customers waiting in line to pay your pricing, and if they aren't, what on earth are they doing there?

That's what a prospect thinks when you reveal your lack of conviction, desperation, and willingness to give up control. Some prospects will exploit it to drain you dry, while others will be too frightened to buy from you even if you paid them.

Walking down a two-way street. Be casual.

If we track each act of repulsion to an uneasiness, fear, misperception, or impulse, it's evident that these sales and marketing disasters were forced communications. Stiff, imbalanced, divisive, combative, bravado-filled, and desperate. They were unnatural and accepted a power struggle between two sparring, suspicious, unequal warriors, rather than a harmonious oneness of two natural, but opposite parties shaking hands.

Sales should be natural, harmonious. Sales should feel good for both parties, not like one party is having their arm twisted.

You may be doing sales wrong if it feels repulsive, icky, or degrading. If you're thinking cringe-worthy thoughts about yourself, your product, service, or sales pitch, imagine what you're projecting to prospects. Don't make it unpleasant, repulsive, or cringeworthy.

Traditional sales organizations used the concept of a sales “funnel” to describe the process through which potential customers move, ending up with sales at the end. Winners today have abandoned that way of thinking in favor of building flywheels — business models in which every element reinforces every other.

Ah, the marketing funnel…

Prospective clients go through a predictable set of experiences, students learn in business school marketing classes. It looks like this:

Understanding the funnel helps evaluate sales success indicators. Gail Goodwin, former CEO of small business direct mail provider Constant Contact, said managing the pipeline was key to escaping the sluggish SaaS ramp of death.

Like the funnel concept. To predict how well your business will do, measure how many potential clients are aware of it (awareness) and how many take the next step. If 1,000 people heard about your offering and 10% showed interest, you'd have 100 at that point. If 50% of these people made buyer-like noises, you'd know how many were, etc. It helped model buying trends.

TV, magazine, and radio advertising are pricey for B2C enterprises. Traditional B2B marketing involved armies of sales reps, which was expensive and a barrier to entry.

Cracks in the funnel model

Digital has exposed the funnel's limitations. Hubspot was born at a time when buyers and sellers had huge knowledge asymmetries, according to co-founder Brian Halligan. Those selling a product could use the buyer's lack of information to become a trusted partner.

As the world went digital, getting information and comparing offerings became faster, easier, and cheaper. Buyers didn't need a seller to move through a funnel. Interactions replaced transactions, and the relationship didn't end with a sale.

Instead, buyers and sellers interacted in a constant flow. In many modern models, the sale is midway through the process (particularly true with subscription and software-as-a-service models). Example:

You're creating a winding journey with many touch points, not a funnel (and lots of opportunities for customers to get lost).

From winding journey to flywheel

Beyond this revised view of an interactive customer journey, a company can create what Jim Collins famously called a flywheel. Imagine rolling a heavy disc on its axis. The first few times you roll it, you put in a lot of effort for a small response. The same effort yields faster turns as it gains speed. Over time, the flywheel gains momentum and turns without your help.

Modern digital organizations have created flywheel business models, in which any additional force multiplies throughout the business. The flywheel becomes a force multiplier, according to Collins.

Amazon is a famous flywheel example. Collins explained the concept to Amazon CEO Jeff Bezos at a corporate retreat in 2001. In The Everything Store, Brad Stone describes in his book The Everything Store how he immediately understood Amazon's levers.

The result (drawn on a napkin):

Low prices and a large selection of products attracted customers, while a focus on customer service kept them coming back, increasing traffic. Third-party sellers then increased selection. Low-cost structure supports low-price commitment. It's brilliant! Every wheel turn creates acceleration.

Where from here?

Flywheel over sales funnel! Consider these business terms.

Start now.

When it comes to building my business, I’m passionate about a lot of things. I love creating user experiences that simplify branding essentials. I love creating new typefaces and color combinations to inspire logo designers. I love fixing problems to improve my product.

Business marketing isn't my thing.

This is shared by many. Many solopreneurs, like me, struggle to advertise their business and drive themselves to work on it.

Without a lot of promotion, no company will succeed. Marketing is 80% of developing a firm, and when you're starting out, it's even more. Some believe that you shouldn't build anything until you've begun marketing your idea and found enough buyers.

Marketing your business without marketing experience is difficult. There are various outlets and techniques to learn. Instead of figuring out where to start, it's easier to return to your area of expertise, whether that's writing, designing product features, or improving your site's back end. Right?

First, realize that your role as a founder is to market your firm. Being a founder focused on product, I rarely work on it.

Secondly, use these basic methods that have helped me dedicate adequate time and focus to marketing. They're all simple to apply, and they've increased my business's visibility and success.

1. Establish buckets for every task.

You've probably heard to schedule tasks you don't like. As simple as it sounds, blocking a substantial piece of my workday for marketing duties like LinkedIn or Twitter outreach, AppSumo customer support, or SEO has forced me to spend time on them.

Giving me lots of room to focus on product development has helped even more. Sure, this means scheduling time to work on product enhancements after my four-hour marketing sprint.

It also involves making space to store product inspiration and ideas throughout the day so I don't get distracted. This is like the advice to keep a notebook beside your bed to write down your insomniac ideas. I keep fonts, color palettes, and product ideas in folders on my desktop. Knowing these concepts won't be lost lets me focus on marketing in the moment. When I have limited time to work on something, I don't have to conduct the research I've been collecting, so I can get more done faster.

2. Look for various accountability systems

Accountability is essential for self-discipline. To keep focused on my marketing tasks, I've needed various streams of accountability, big and little.

Accountability groups are great for bigger things. SaaS Camp, a sales outreach coaching program, is mine. We discuss marketing duties and results every week. This motivates me to do enough each week to be proud of my accomplishments. Yet hearing what works (or doesn't) for others gives me benchmarks for my own marketing outcomes and plenty of fresh techniques to attempt.

… say, I want to DM 50 people on Twitter about my product — I get that many Q-tips and place them in one pen holder on my desk.

The best accountability group can't watch you 24/7. I use a friend's simple method that shouldn't work (but it does). When I have a lot of marketing chores, like DMing 50 Twitter users about my product, That many Q-tips go in my desk pen holder. After each task, I relocate one Q-tip to an empty pen holder. When you have a lot of minor jobs to perform, it helps to see your progress. You might use toothpicks, M&Ms, or anything else you have a lot of.

3. Continue to monitor your feedback loops

Knowing which marketing methods work best requires monitoring results. As an entrepreneur with little go-to-market expertise, every tactic I pursue is an experiment. I need to know how each trial is doing to maximize my time.

I placed Google and Facebook advertisements on hold since they took too much time and money to obtain Return. LinkedIn outreach has been invaluable to me. I feel that talking to potential consumers one-on-one is the fastest method to grasp their problem areas, figure out my messaging, and find product market fit.

Data proximity offers another benefit. Seeing positive results makes it simpler to maintain doing a work you don't like. Why every fitness program tracks progress.

Marketing's goal is to increase customers and revenues, therefore I've found it helpful to track those metrics and celebrate monthly advances. I provide these updates for extra accountability.

Finding faster feedback loops is also motivating. Marketing brings more clients and feedback, in my opinion. Product-focused founders love that feedback. Positive reviews make me proud that my product is benefitting others, while negative ones provide me with suggestions for product changes that can improve my business.

The best advice I can give a lone creator who's afraid of marketing is to just start. Start early to learn by doing and reduce marketing stress. Start early to develop habits and successes that will keep you going. The sooner you start, the sooner you'll have enough consumers to return to your favorite work.

I apologize if this sounds basic, but throughout my career, I've always been clear that a company's activities are shaped by its founder(s)' morality.

I consider Palantir, owned by PayPal founder Peter Thiel, evil. He got $5 billion tax-free by hacking a statute to help middle-class savings. That may appear clever, but I think it demonstrates a shocking lack of solidarity with society. As a result of this and other things he has said and done, I early on dismissed Peter Thiel as someone who could contribute anything positive to society, and events soon proved me right: we are talking about someone who clearly considers himself above everyone else and who does not hesitate to set up a company, Palantir, to exploit the data of the little people and sell it to the highest bidder, whoever that is and whatever the consequences.

The German courts have confirmed my warnings concerning Palantir. The problem is that politicians love its surveillance tools because they think knowing more about their constituents gives them power. These are ideal for dictatorships who want to snoop on their populace. Hence, Silicon Valley's triumphalist dialectic has seduced many governments at many levels and collected massive volumes of data to hold forever.

Dangerous company. There are many more. My analysis of the moral principles that disclose company management changed my opinion of Facebook, now Meta, and anyone with a modicum of interest might deduce when that happened, a discovery that leaves you dumbfounded. TikTok was easy because its lack of morality was revealed early when I saw the videos it encouraged minors to post and the repercussions of sharing them through its content recommendation algorithm. When you see something like this, nothing can convince you that the firm can change its morals and become good. Nothing. You know the company is awful and will fail. Speak it, announce it, and change it. It's like a fingerprint—unchangeable.

Some of you who read me frequently make its Facebook today jokes when I write about these firms, and that's fine: they're my moral standards, those of an elderly professor with thirty-five years of experience studying corporations and discussing their cases in class, but you don't have to share them. Since I'm writing this and don't have to submit to any editorial review, that's what it is: when you continuously read a person, you have to assume that they have moral standards and that sometimes you'll agree with them and sometimes you won't. Morality accepts hierarchies, nuances, and even obsessions. I know not everyone shares my opinions, but at least I can voice them. One day, one of those firms may sue me (as record companies did some years ago).

Palantir is incredibly harmful. Limit its operations. Like Meta and TikTok, its business strategy is shaped by its founders' immorality. Such a procedure can never be beneficial.

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.