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.

This report from Mark Gurman has stuck with me:

In the News and Stocks apps, the display ads are no different than what you might get on an ad-supported website. In the App Store, the ads are for actual apps, which are probably more useful for Apple users than mortgage rates. Some people may resent Apple putting ads in the News and Stocks apps. After all, the iPhone is supposed to be a premium device. Let’s say you shelled out $1,000 or more to buy one, do you want to feel like Apple is squeezing more money out of you just to use its standard features? Now, a portion of ad revenue from the News app’s Today tab goes to publishers, but it’s not clear how much. Apple also lets publishers advertise within their stories and keep the vast majority of that money. Surprisingly, Today ads also appear if you subscribe to News+ for $10 per month (though it’s a smaller number).

I use Apple News often. It's a good general news catch-up tool, like Twitter without the BS. Customized notifications are helpful. Fast and lovely. Except for advertisements. I have Apple One, which includes News+, and while I understand why the magazines still have brand ads, it's ridiculous to me that Apple enables web publishers to introduce awful ads into this experience. Apple's junky commercials are ridiculous.

We know publishers want and probably requested this. Let's keep Apple News ad-free for the much smaller percentage of paid users, and here's your portion. (Same with Stocks, which is more sillier.)

Paid app placement in the App Store is a wonderful approach for developers to find new users (though far too many of those ads are trying to trick users, in my opinion).

Apple is also planning to increase ads in its Maps app. This sounds like Google Maps, and I don't like it. I never find these relevant, and they clutter up the user experience. Apple Maps now has a UI advantage (though not a data/search one, which matters more).

Apple is nickel-and-diming its customers. We spend thousands for their products and premium services like Apple One. We all know why: income must rise, and new firms are needed to scale. This will eventually backfire.

900K impressions, 8K clicks, and $$$ orders…

I recently started dropshipping. Now that I own my business and can charge it as a business expense, it feels less like money wasted if it doesn't work. I also made t-shirts to sell. I intended to open a t-shirt store and had many designs on a hard drive. I read that Tiktok advertising had a high conversion rate and low cost because they were new. According to many, the advertising' cost/efficiency ratio would plummet and become as bad as Google or Facebook Ads. Now felt like the moment to try Tiktok marketing and dropshipping. I work in marketing for a SaaS firm and have seen how poorly ads perform. I wanted to try it alone.

I set up $250 and ran advertising for a week. Before that, I made my own products, store, and marketing. In this post, I'll show you my process and results.

Setting up the store

Dropshipping is a sort of retail business in which the manufacturer ships the product directly to the client through an online platform maintained by a seller. The seller takes orders but has no stock. The manufacturer handles all orders. This no-stock concept increases profitability and flexibility.

In my situation, I used previous t-shirt designs to make my own product. I didn't want to handle order fulfillment logistics, so I looked for a way to print my designs on demand, ship them, and handle order tracking/returns automatically. So I found Printful.

I needed to connect my backend and supplier to a storefront so visitors could buy. 99% of dropshippers use Shopify, but I didn't want to master the difficult application. I wanted a one-day project. I'd previously worked with Big Cartel, so I chose them.

Big Cartel doesn't collect commissions on sales, simply a monthly flat price ($9.99 to $19.99 depending on your plan).

After opening a Big Cartel account, I uploaded 21 designs and product shots, then synced each product with Printful.

Developing the ads

I mocked up my designs on cool people photographs from placeit.net, a great tool for creating product visuals when you don't have a studio, camera gear, or models to wear your t-shirts.

I opened an account on the website and had advertising visuals within 2 hours.

Because my designs are simple (black design on white t-shirt), I chose happy, stylish people on plain-colored backdrops. After that, I had to develop an animated slideshow.

Because I'm a graphic designer, I chose to use Adobe Premiere to create animated Tiktok advertising.

Premiere is a fancy video editing application used for more than advertisements. Premiere is used to edit movies, not social media marketing. I wanted this experiment to be quick, so I got 3 social media ad templates from motionarray.com and threw my visuals in. All the transitions and animations were pre-made in the files, so it only took a few hours to compile. The result:

I downloaded 3 different soundtracks for the videos to determine which would convert best.

After that, I opened a Tiktok business account, uploaded my films, and inserted ad info. They went live within one hour.

The (poor) outcomes

As a European company, I couldn't deliver ads in the US. All of my advertisements' material (title, description, and call to action) was in English, hence they continued getting rejected in Europe for countries that didn't speak English. There are a lot of them:

I lost a lot of quality traffic, but I felt that if the images were engaging, people would check out the store and buy my t-shirts. I was wrong.

• 51,071 impressions on Day 1. 0 orders after 411 clicks

• 114,053 impressions on Day 2. 1.004 clicks and no orders

• Day 3: 987 clicks, 103,685 impressions, and 0 orders

• 101,437 impressions on Day 4. 0 orders after 963 clicks

• 115,053 impressions on Day 5. 1,050 clicks and no purchases

• 125,799 impressions on day 6. 1,184 clicks, no purchases

• 115,547 impressions on Day 7. 1,050 clicks and no purchases

• 121,456 impressions on day 8. 1,083 clicks, no purchases

• 47,586 impressions on Day 9. 419 Clicks. No orders

My overall conversion rate for video advertisements was 0.9%. TikTok's paid ad formats all result in strong engagement rates (ads average 3% to 12% CTR to site), therefore a 1 to 2% CTR should have been doable.

My one-week experiment yielded 8,151 ad clicks but no sales. Even if 0.1% of those clicks converted, I should have made 8 sales. Even companies with horrible web marketing would get one download or trial sign-up for every 8,151 clicks. I knew that because my advertising were in English, I had no impressions in the main EU markets (France, Spain, Italy, Germany), and that this impacted my conversion potential. I still couldn't believe my numbers.

I dug into the statistics and found that Tiktok's stats didn't match my store traffic data.

Looking more closely at the numbers

My ads were approved on April 26 but didn't appear until April 27. My store dashboard showed 440 visitors but 1,004 clicks on Tiktok. This happens often while tracking campaign results since different platforms handle comparable user activities (click, view) differently. In online marketing, residual data won't always match across tools.

My data gap was too large. Even if half of the 1,004 persons who clicked closed their browser or left before the store site loaded, I would have gained 502 visitors. The significant difference between Tiktok clicks and Big Cartel store visits made me suspicious. It happened all week:

• Day 1: 440 store visits and 1004 ad clicks

• Day 2: 482 store visits, 987 ad clicks

• 3rd day: 963 hits on ads, 452 store visits

• 443 store visits and 1,050 ad clicks on day 4.

• Day 5: 459 store visits and 1,184 ad clicks

• Day 6: 430 store visits and 1,050 ad clicks

• Day 7: 409 store visits and 1,031 ad clicks

• Day 8: 166 store visits and 418 ad clicks

The disparity wasn't related to residual data or data processing. The disparity between visits and clicks looked regular, but I couldn't explain it.

After the campaign concluded, I discovered all my creative assets (the videos) had a 0% CTR and a $0 expenditure in a separate dashboard. Whether it's a dashboard reporting issue or a budget allocation bug, online marketers shouldn't see this.

Tiktok can present any stats they want on their dashboard, just like any other platform that runs advertisements to promote content to its users. I can't verify that 895,687 individuals saw and clicked on my ad. I invested $200 for what appears to be around 900K impressions, which is an excellent ROI. No one bought a t-shirt, even an unattractive one, out of 900K people?

Would I do it again?

Nope. Whether I didn't make sales because Tiktok inflated the dashboard numbers or because I'm horrible at producing advertising and items that sell, I’ll stick to writing content and making videos. If setting up a business and ads in a few days was all it took to make money online, everyone would do it.

Video advertisements and dropshipping aren't dead. As long as the internet exists, people will click ads and buy stuff. Converting ads and selling stuff takes a lot of work, and I want to focus on other things.

I had always wanted to try dropshipping and I’m happy I did, I just won’t stick to it because that’s not something I’m interested in getting better at.

If I want to sell t-shirts again, I'll avoid Tiktok advertisements and find another route.

Many developers do it, but I don't approve.

Aren't many programmers part-time? Many work full-time but also freelance. If the job agreement allows it, I see no problem.

Tech businesses' policies vary. I have a friend in Google, Germany. According to his contract, he couldn't do an outside job. Google owns any code he writes while employed.

I was shocked. Later, I found that different Google regions have different policies.

A corporation can normally establish any agreement before hiring you. They're negotiable. When there's no agreement, state law may apply. In court, law isn't so simple.

I won't delve into legal details. Instead, let’s talk about the incident.

How he was discovered

In one month, he missed two deadlines. His boss was frustrated because the assignment wasn't difficult to miss twice. When a team can't finish work on time, they all earn bad grades.

He annoyed the whole team. One team member (anonymous) told the project manager he worked on side projects during office hours. He may have missed deadlines because of this.

The project manager was furious. He needed evidence. The manager caught him within a week. The manager told higher-ups immediately.

The company wanted to set an example

Management could terminate him and settle the problem. But the company wanted to set an example for those developers who breached the regulation.

Because dismissal isn't enough. Every organization invests heavily in developer hiring. If developers depart or are fired after a few months, the company suffers.

The developer spent 10 months there. The employer sacked him and demanded ten months' pay. Or they'd sue him.

It was illegal and unethical. The youngster paid the fine and left the company quietly to protect his career.

Right or wrong?

Is the developer's behavior acceptable? Let's discuss developer malpractice.

During office hours, may developers work on other projects? If they're bored during office hours, they might not. Check the employment contract or state law.

If there's no employment clause, check country/state law. Because you can't justify breaking the law. Always. Most employers own their employees' work hours unless it's a contractual position.

If the company agrees, it's fine.

I also oppose companies that force developers to work overtime without pay.

Most states and countries have laws that help companies and workers. Law supports employers in this case. If any of the following are true, the company/employer owns the IP under California law.

• using the business's resources

• any equipment, including a laptop used for business.

• company's mobile device.

• offices of the company.

• business time as well. This is crucial. Because this occurred in the instance of my junior.

Company resources are dangerous. Because your company may own the product's IP.  If you have seen the TV show Silicon Valley, you have seen a similar situation there, right?

Conclusion

Simple rule. I avoid big side projects. I work on my laptop on weekends for side projects. I'm safe. But I also know that my company might not be happy with that.

As an employee, I suppose I can. I can make side money. I won't promote it, but I'll respect their time, resources, and task. I also sometimes work extra time to finish my company’s deadlines.

People are slowly recognizing entrepreneurship's downside.

Growing up, entrepreneurship wasn't common. High school class of 2012 had no entrepreneurs.

Businesses were different.

They had staff and a lengthy history of achievement.

I never wanted a business. It felt unattainable. My friends didn't care.

Weird.

People desired degrees to attain good jobs at big companies.

When graduated high school:

• 9 out of 10 people attend college

• Earn minimum wage (7%) working in a restaurant or retail establishment

• Or join the military (3%)

Later, entrepreneurship became a thing.

2014-ish

I was in the military and most of my high school friends were in college, so I didn't hear anything.

Entrepreneurship soared in 2015, according to Google Trends.

Then more individuals were interested. Entrepreneurship went from unusual to cool.

In 2015, it was easier than ever to build a website, run Facebook advertisements, and achieve organic social media reach.

There were several online business tools.

You didn't need to spend years or money figuring it out. Most entry barriers were gone.

Everyone wanted a side gig to escape the 95.

Small company applications have increased during the previous 10 years.

2011-2014 trend continues.

2015 adds 150,000 applications. 2016 adds 200,000. Plus 300,000 in 2017.

The graph makes it look little, but that's a considerable annual spike with no indications of stopping.

By 2021, new business apps had doubled.

Entrepreneurship will return to its early 2010s level.

I think we'll go backward in 5 years.

Entrepreneurship is half as popular as it was in 2015.

In the late 2020s and 30s, entrepreneurship will again be obscure.

Entrepreneurship's decade-long splendor is fading. People will cease escaping 9-5 and launch fewer companies.

That’s not a bad thing.

I think people have a rose-colored vision of entrepreneurship. It's fashionable. People feel that they're missing out if they're not entrepreneurial.

Reality is showing up.

People say on social media, "I knew starting a business would be hard, but not this hard."

More negative posts on entrepreneurship:

Luke adds:

Is being an entrepreneur ‘healthy’? I don’t really think so. Many like Gary V, are not role models for a well-balanced life. Despite what feel-good LinkedIn tells you the odds are against you as an entrepreneur. You have to work your face off. It’s a tough but rewarding lifestyle. So maybe let’s stop glorifying it because it takes a lot of (bleepin) work to survive a pandemic, mental health battles, and a competitive market.

Entrepreneurship is no longer a pipe dream.

It’s hard.

I went full-time in March 2020. I was done by April 2021. I had a good-paying job with perks.

When that fell through (on my start date), I had to continue my entrepreneurial path. I needed money by May 1 to pay rent.

Entrepreneurship isn't as great as many think.

Entrepreneurship is a serious business.

If you have a 9-5, the grass isn't greener here. Most people aren't telling the whole story when they post on social media or quote successful entrepreneurs.

People prefer to communicate their victories than their defeats.

Is this a bad thing?

I don’t think so.

Over the previous decade, entrepreneurship went from impossible to the finest thing ever.

It peaked in 2020-21 and is returning to reality.

Startups aren't for everyone.

If you like your job, don't quit.

Entrepreneurship won't amaze people if you quit your job.

It's irrelevant.

You're doomed.

And you'll probably make less money.

If you hate your job, quit. Change jobs and bosses. Changing jobs could net you a greater pay or better perks.

When you go solo, your paycheck and perks vanish. Did I mention you'll fail, sleep less, and stress more?

Nobody will stop you from pursuing entrepreneurship. You'll face several challenges.

Possibly.

Entrepreneurship may be romanticized for years.

Based on what I see from entrepreneurs on social media and trends, entrepreneurship is challenging and few will succeed.