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.

A J.Crew collaboration for fashion label Eveliina Vintage is not a paradox; it is a solution.

Eveliina Vintage's capsule collection debuted yesterday at J.Crew. This J.Crew partnership stopped me in my tracks.

Eveliina Vintage sells vintage goods. Eeva Musacchia founded the shop in Finland in the 1970s. It's recognized for its one-of-a-kind slip dresses from the 1930s and 1940s.

I wondered why a vintage brand would partner with a mass shop. Fast fashion against vintage shopping? Will Eveliina Vintages customers be turned off?

But Eveliina Vintages customers don't care about sustainability. They want Eveliina's Instagram look. Eveliina Vintage collaborated with J.Crew to give customers what they wanted: more Eveliina at a lower price.

Vintage: A Fashion Option That Is Eco-Conscious

Secondhand shopping is a trendy response to quick fashion. J.Crew releases hundreds of styles annually. Waste and environmental damage have been criticized. A pair of jeans requires 1,800 gallons of water. J.Crew's limited-time deals promote more purchases. J.Crew items are likely among those Americans wear 7 times before discarding.

Consumers and designers have emphasized sustainability in recent years. Stella McCartney and Eileen Fisher are popular eco-friendly brands. They've also flocked to ThredUp and similar sites.

Gap, Levis, and Allbirds have listened to consumer requests. They promote recycling, ethical sourcing, and secondhand shopping.

Secondhand shoppers feel good about reusing and recycling clothing that might have ended up in a landfill.

Eco-conscious fashionistas shop vintage. These shoppers enjoy the thrill of the hunt (that limited-edition Chanel bag!) and showing off a unique piece (nobody will have my look!). They also reduce their environmental impact.

Is Eveliina Vintage capitalizing on an aesthetic or is it a sustainable brand?

Eveliina Vintage emphasizes environmental responsibility. Vogue's Amanda Musacchia emphasized sustainability. Amanda, founder Eeva's daughter, is a company leader.

But Eveliina's press message doesn't address sustainability, unlike Instagram. Scarcity and fame rule.

Eveliina Vintages Instagram has see-through dresses and lace-trimmed slip dresses. Celebrities and influencers are often photographed in Eveliina's apparel, which has 53,000+ followers. Vogue appreciates Eveliina's style. Multiple publications discuss Alexa Chung's Eveliina dress.

Eveliina Vintage markets its one-of-a-kind goods. It teases future content, encouraging visitors to return. Scarcity drives demand and raises clothing prices. One dress is $1,600+, but most are $500-$1,000.

The catch: Eveliina can't monetize its expanding popularity due to exorbitant prices and limited quantity. Why?

1. Most people struggle to pay for their clothing. But Eveliina Vintage lacks those more affordable entry-level products, in contrast to other luxury labels that sell accessories or perfume.

2. Many people have trouble fitting into their clothing. The bodies of most women in the past were different from those for which vintage clothing was designed. Each Eveliina dress's specific measurements are mentioned alongside it. Be careful, you can fall in love with an ill-fitting dress.

3. No matter how many people can afford it and fit into it, there is only one item to sell. To get the item before someone else does, those people must be on the Eveliina Vintage website as soon as it becomes available.

A Way for Eveliina Vintage to Make Money (and Expand) with J.Crew Its following

Eveliina Vintages' cooperation with J.Crew makes commercial sense.

This partnership spreads Eveliina's style. Slightly better pricing The $390 outfits have multicolored slips and gauzy cotton gowns. Sizes range from 00 to 24, which is wider than vintage racks.

Eveliina Vintage customers like the combination. Excited comments flood the brand's Instagram launch post. Nobody is mocking the 50-year-old vintage brand's fast-fashion partnership.

Vintage may be a sustainable fashion trend, but that's not why Eveliina's clients love the brand. They only care about the old look.

And that is a tale as old as fashion.

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.

Startup entrepreneurs assume what risks when pitching?

Last week I signed four NDAs.

Four!

NDA stands for non-disclosure agreement. A legal document given to someone receiving confidential information. By signing, the person pledges not to share the information for a certain time. If they do, they may be in breach of contract and face legal action.

Companies use NDAs to protect trade secrets and confidential internal information from employees and contractors. Appropriate. If you manage a huge, successful firm, you don't want your employees selling their information to your competitors. To be true, business NDAs don't always prevent corporate espionage, but they usually make employees and contractors think twice before sharing.

I understand employee and contractor NDAs, but I wasn't asked to sign one. I counsel entrepreneurs, thus the NDAs I signed last week were from startups that wanted my feedback on their concepts.

I’m not a startup investor. I give startup guidance online. Despite that, four entrepreneurs thought their company ideas were so important they wanted me to sign a generically written legal form they probably acquired from a shady, spam-filled legal templates website before we could chat.

False. One company tried to get me to sign their NDA a few days after our conversation. I gently rejected, but their tenacity encouraged me. I considered sending retroactive NDAs to everyone I've ever talked to about one of my startups in case they establish a successful company based on something I said.

Two of the other three NDAs were from nearly identical companies. Good thing I didn't sign an NDA for the first one, else they may have sued me for talking to the second one as though I control the firms people pitch me.

I wasn't talking to the fourth NDA company. Instead, I received an unsolicited email from someone who wanted comments on their fundraising pitch deck but required me to sign an NDA before sending it.

That's right, before I could read a random Internet stranger's unsolicited pitch deck, I had to sign his NDA, potentially limiting my ability to discuss what was in it.

You should understand. Advisors, mentors, investors, etc. talk to hundreds of businesses each year. They cannot manage all the companies they deal with, thus they cannot risk legal trouble by talking to someone. Well, if I signed NDAs for all the startups I spoke with, half of the 300+ articles I've written on Medium over the past several years could get me sued into the next century because I've undoubtedly addressed topics in my articles that I discussed with them.

The four NDAs I received last week are part of a recent trend of entrepreneurs sending out NDAs before meetings, despite the practical and legal issues. They act like asking someone to sign away their right to talk about all they see and hear in a day is as straightforward as asking for a glass of water.

Given this inflow of NDAs, I wanted to briefly remind entrepreneurs reading this blog about the merits and cons of requesting investors (or others in the startup ecosystem) to sign your NDA.

Benefits of having investors sign your NDA include:

None. Zero. Nothing.

Disadvantages of requesting investor NDAs:

• You'll come off as an amateur who has no idea what it takes to launch a successful firm.

• Investors won't trust you with their money since you appear to be a complete amateur.

• Printing NDAs will be a waste of paper because no genuine entrepreneur will ever sign one.

I apologize for missing any cons. Please leave your remarks.

Recent investigations have shown that generative AI can boost hackers and misinformation spreaders.

Since its inception in late November 2022, OpenAI's ChatGPT has entertained and assisted many online users in writing, coding, task automation, and linguistic translation. Given this versatility, it is maybe unsurprising but nonetheless regrettable that fraudsters and mis-, dis-, and malinformation (MDM) spreaders are also considering ChatGPT and related AI models to streamline and improve their operations.

Malign actors may benefit from ChatGPT, according to a WithSecure research. ChatGPT promises to elevate unlawful operations across many attack channels. ChatGPT can automate spear phishing attacks that deceive corporate victims into reading emails from trusted parties. Malware, extortion, and illicit fund transfers can result from such access.

ChatGPT's ability to simulate a desired writing style makes spear phishing emails look more genuine, especially for international actors who don't speak English (or other languages like Spanish and French).

This technique could let Russian, North Korean, and Iranian state-backed hackers conduct more convincing social engineering and election intervention in the US. ChatGPT can also create several campaigns and various phony online personas to promote them, making such attacks successful through volume or variation. Additionally, image-generating AI algorithms and other developing techniques can help these efforts deceive potential victims.

Hackers are discussing using ChatGPT to install malware and steal data, according to a Check Point research. Though ChatGPT's scripts are well-known in the cyber security business, they can assist amateur actors with little technical understanding into the field and possibly develop their hacking and social engineering skills through repeated use.

Additionally, ChatGPT's hacking suggestions may change. As a writer recently indicated, ChatGPT's ability to blend textual and code-based writing might be a game-changer, allowing the injection of innocent content that would subsequently turn out to be a malicious script into targeted systems. These new AI-powered writing- and code-generation abilities allow for unique cyber attacks, regardless of viability.

OpenAI fears ChatGPT usage. OpenAI, Georgetown University's Center for Security and Emerging Technology, and Stanford's Internet Observatory wrote a paper on how AI language models could enhance nation state-backed influence operations. As a last resort, the authors consider polluting the internet with radioactive or misleading data to ensure that AI language models produce outputs that other language models can identify as AI-generated. However, the authors of this paper seem unaware that their "solution" might cause much worse MDM difficulties.

Literally False News

The public argument about ChatGPTs content-generation has focused on originality, bias, and academic honesty, but broader global issues are at stake. ChatGPT can influence public opinion, troll individuals, and interfere in local and national elections by creating and automating enormous amounts of social media material for specified audiences.

ChatGPT's capacity to generate textual and code output is crucial. ChatGPT can write Python scripts for social media bots and give diverse content for repeated posts. The tool's sophistication makes it irrelevant to one's language skills, especially English, when writing MDM propaganda.

I ordered ChatGPT to write a news piece in the style of big US publications declaring that Ukraine is on the verge of defeat in its fight against Russia due to corruption, desertion, and exhaustion in its army. I also gave it a fake reporter's byline and an unidentified NATO source's remark. The outcome appears convincing:

Worse, terrible performers can modify this piece to make it more credible. They can edit the general's name or add facts about current wars. Furthermore, such actors can create many versions of this report in different forms and distribute them separately, boosting its impact.

In this example, ChatGPT produced a news story regarding (fictional) greater moviegoer fatality rates:

Editing this example makes it more plausible. Dr. Jane Smith, the putative author of the medical report, might be replaced with a real-life medical person or a real victim of this supposed medical hazard.

Can deceptive texts be found? Detecting AI text is behind AI advancements. Minor AI-generated text alterations can upset these technologies.

Some OpenAI individuals have proposed covert methods to watermark AI-generated literature to prevent its abuse. AI models would create information that appears normal to humans but would follow a cryptographic formula that would warn other machines that it was AI-made. However, security experts are cautious since manually altering the content interrupts machine and human detection of AI-generated material.

How to Prepare

Cyber security and IT workers can research and use generative AI models to fight spear fishing and extortion. Governments may also launch MDM-defence projects.

In election cycles and global crises, regular people may be the most vulnerable to AI-produced deceit. Until regulation or subsequent technical advances, individuals must recognize exposure to AI-generated fraud, dating scams, other MDM activities.

A three-step verification method of new material in suspicious emails or social media posts can help identify AI content and manipulation. This three-step approach asks about the information's distribution platform (is it reliable? ), author (is the reader familiar with them? ), and plausibility given one's prior knowledge of the topic.

Consider a report by a trusted journalist that makes shocking statements in their typical manner. AI-powered fake news may be released on an unexpected platform, such as a newly created Facebook profile. However, if it links to a known media source, it is more likely to be real.

Though hard and subjective, this verification method may be the only barrier against manipulation for now.

AI language models:

How to Recognize an AI-Generated Article ChatGPT, the popular AI-powered chatbot, can and likely does generate medium.com-style articles.

AI-Generated Text Detectors Fail. Do This. Online tools claim to detect ChatGPT output. Even with superior programming, I tested some of these tools. pub

Why Original Writers Matter Despite AI Language Models Creative writers may never be threatened by AI language models.