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.

This resulted to obimy's new audience.

Hi! obimy's official account. Here, we'll teach app developers and marketers. In 2022, our downloads increased dramatically, so we'll share what we learned.

obimy is what we call a ‘senseger’. It's a new method to communicate digitally. Instead of text, obimy users connect through senses and moods. Feeling playful? Flirt with your partner, pat a pal, or dump water on a classmate. Each feeling is an interactive animation with vibration. It's a wordless app. App Store and Google Play have obimy.

We had 20,000 users in 2022. Two to five thousand of them opened the app monthly. Our DAU metric was 500.

We have 6 million users after 6 months. 500,000 individuals use obimy daily. obimy was the top lifestyle app this week in the U.S.

And TikTok helped.

TikTok fuels obimys' growth. It's why our app exploded. How and what did we learn? Our Head of Marketing, Anastasia Avramenko, knows.

our actions prior to TikTok

We wanted to achieve product-market fit through organic expansion. Quora, Reddit, Facebook Groups, Facebook Ads, Google Ads, Apple Search Ads, and social media activity were tested. Nothing worked. Our CPI was sometimes $4, so unit economics didn't work.

We studied our markets and made audience hypotheses. We promoted our goods and studied our audience through social media quizzes. Our target demographic was Americans in long-distance relationships. I designed quizzes like Test the Strength of Your Relationship to better understand the user base. After each quiz, we encouraged users to download the app to enhance their connection and bridge the distance.

We got 1,000 responses for $50. This helped us comprehend the audience's grief and coping strategies (aka our rivals). I based action items on answers given. If you can't embrace a loved one, use obimy.

We also tried Facebook and Google ads. From the start, we knew it wouldn't work.

We were desperate to discover a free way to get more users.

Our journey to TikTok

TikTok is a great venue for emerging creators. It also helped reach people. Before obimy, my TikTok videos garnered 12 million views without sponsored promotion.

We had to act. TikTok was required.

I wasn't a TikTok user before obimy. Initially, I uploaded promotional content. Call-to-actions appear strange next to dancing challenges and my money don't jiggle jiggle. I learned TikTok. Watch TikTok for an hour was on my to-do list. What a dream job!

Our most popular movies presented the app alongside text outlining what it does. We started promoting them in Europe and the U.S. and got a 16% CTR and $1 CPI, an improvement over our previous efforts.

Somehow, we were expanding. So we came up with new hypotheses, calls to action, and content.

Four months passed, yet we saw no organic growth.

Russia attacked Ukraine.

Our app aimed to be helpful. For now, we're focusing on our Ukrainian audience. I posted sloppy TikToks illustrating how obimy can help during shelling or air raids.

In two hours, Kostia sent me our visitor count. Our servers crashed.

Initially, we had several thousand daily users. Over 200,000 users joined obimy in a week. They posted obimy videos on TikTok, drawing additional users. We've also resumed U.S. video promotion.

We gained 2,000,000 new members with less than $100 in ads, primarily in the U.S. and U.K.

TikTok helped.

The figures

We were confident we'd chosen the ideal tool for organic growth.

• Over 45 million people have viewed our own videos plus a ton of user-generated content with the hashtag #obimy.

• About 375 thousand people have liked all of our individual videos.

• The number of downloads and the virality of videos are directly correlated.

Where are we now?

TikTok fuels our organic growth. We post 56 videos every week and pay to promote viral content.

We use UGC and influencers. We worked with Universal Music Italy on Eurovision. They offered to promote us through their million-follower TikTok influencers. We thought their followers would improve our audience, but it didn't matter. Integration didn't help us. Users that share obimy videos with their followers can reach several million views, which affects our download rate.

After the dust settled, we determined our key audience was 13-18-year-olds. They want to express themselves, but it's sometimes difficult. We're searching for methods to better engage with our users. We opened a Discord server to discuss anime and video games and gather app and content feedback.

TikTok helps us test product updates and hypotheses. Example: I once thought we might raise MAU by prompting users to add strangers as friends. Instead of asking our team to construct it, I made a TikTok urging users to share invite URLs. Users share links under every video we upload, embracing people worldwide.

Key lessons

Don't direct-sell. TikTok isn't for Instagram, Facebook, or YouTube promo videos. Conventional advertisements don't fit. Most users will swipe up and watch humorous doggos.

More product videos are better. Finally. So what?

Encourage interaction. Tagging friends in comments or making videos with the app promotes it more than any marketing spend.

Be odd and risqué. A user mistakenly sent a French kiss to their mom in one of our most popular videos.

TikTok helps test hypotheses and build your user base. It also helps develop apps. In our upcoming blog, we'll guide you through obimy's design revisions based on TikTok. Follow us on Twitter, Instagram, and TikTok.

If I could tell my younger self a few rules, they would boost my career.

1. Treat design like medicine; don't get attached.

If it doesn't help, you won't be angry, but you'll try to improve it. Designers blame others if they don't like the design, but the rule is the same: we solve users' problems. You're not your design, and neither are they. Be humble with your work because your assumptions will often be wrong and users will behave differently.

2. Consider your design flawed.

Disagree with yourself, then defend your ideas. Most designers forget to dig deeper into a pattern, screen, button, or copywriting. If someone asked, "Have you considered alternatives? How does this design stack up? Here's a functional UX checklist to help you make design decisions.

3. Codeable solutions.

If your design requires more developer time, consider whether it's worth spending more money to code something with a small UX impact. Overthinking problems and designing abstract patterns is easy. Sometimes you see something on dribbble or bechance and try to recreate it, but it's not worth it. Here's my article on it.

4. Communication changes careers

Designers often talk with users, clients, companies, developers, and other designers. How you talk and present yourself can land you a job. Like driving or swimming, practice it. Success requires being outgoing and friendly. If I hadn't said "hello" to a few people, I wouldn't be where I am now.

5. Ignorance of the law is not an excuse.

Copyright, taxation How often have you used an icon without checking its license? If you use someone else's work in your project, the owner can cause you a lot of problems — paying a lot of money isn't worth it. Spend a few hours reading about copyrights, client agreements, and taxes.

6. Always test your design

If nobody has seen or used my design, it's not finished. Ask friends about prototypes. Testing reveals how wrong your assumptions were. Steve Krug, one of the authorities on this topic will tell you more about how to do testing.

7. Run workshops

A UX designer's job involves talking to people and figuring out what they need, which is difficult because they usually don't know. Organizing teamwork sessions is a powerful skill, but you must also be a good listener. Your job is to help a quiet, introverted developer express his solution and control the group. AJ Smart has more on workshops here.

Ray Dalio's super-effective roadmap 

Ray Dalio's $22 billion net worth ranks him 36th globally. From 1975 to 2011, he built the world's most successful hedge fund, never losing more than 4% from 1991 to 2020. (and only doing so during 3 calendar years). 

Dalio describes a 5-step process in his best-selling book Principles. It's the playbook he's used to build his hedge fund, beat the markets, and face personal challenges. 

This 5-step system is so valuable and well-explained that I didn't edit or change anything; I only added my own insights in the parts I found most relevant and/or relatable as a young entrepreneur. The system's overview: 

1. Have clear goals 

2. Identify and don’t tolerate problems 

3. Diagnose problems to get at their root causes 

4. Design plans that will get you around those problems 

5. Do what is necessary to push through the plans to get results 

If you follow these 5 steps in a virtuous loop, you'll almost always see results. Repeat the process for each goal you have. 

1. Have clear goals 

a) Prioritize: You can have almost anything, but not everything. 

I started and never launched dozens of projects for 10 years because I was scattered. I opened a t-shirt store, traded algorithms, sold art on Instagram, painted skateboards, and tinkered with electronics. I decided to try blogging for 6 months to see where it took me. Still going after 3 years. 

b) Don’t confuse goals with desires. 

A goal inspires you to act. Unreasonable desires prevent you from achieving your goals. 

c) Reconcile your goals and desires to decide what you want. 

d) Don't confuse success with its trappings. 

e) Never dismiss a goal as unattainable. 

Always one path is best. Your perception of what's possible depends on what you know now. I never thought I'd make money writing online so quickly, and now I see a whole new horizon of business opportunities I didn't know about before. 

f) Expectations create abilities. 

Don't limit your abilities. More you strive, the more you'll achieve. 

g) Flexibility and self-accountability can almost guarantee success. 

Flexible people accept what reality or others teach them. Self-accountability is the ability to recognize your mistakes and be more creative, flexible, and determined. 

h) Handling setbacks well is as important as moving forward. 

Learn when to minimize losses and when to let go and move on. 

2. Don't ignore problems 

a) See painful problems as improvement opportunities. 

Every problem, painful situation, and challenge is an opportunity. Read The Art of Happiness for more. 

b) Don't avoid problems because of harsh realities. 

Recognizing your weaknesses isn't the same as giving in. It's the first step in overcoming them. 

c) Specify your issues. 

There is no "one-size-fits-all" solution. 

d) Don’t mistake a cause of a problem with the real problem. 

"I can't sleep" is a cause, not a problem. "I'm underperforming" could be a problem. 

e) Separate big from small problems. 

You have limited time and energy, so focus on the biggest problems. 

f) Don't ignore a problem. 

Identifying a problem and tolerating it is like not identifying it. 

3. Identify problems' root causes 

a) Decide "what to do" after assessing "what is." 

"A good diagnosis takes 15 to 60 minutes, depending on its accuracy and complexity. [...] Like principles, root causes recur in different situations. 

b) Separate proximate and root causes. 

"You can only solve problems by removing their root causes, and to do that, you must distinguish symptoms from disease." 

c) Knowing someone's (or your own) personality can help you predict their behavior. 

4. Design plans that will get you around the problems 

a) Retrace your steps. 

Analyze your past to determine your future. 

b) Consider your problem a machine's output. 

Consider how to improve your machine. It's a game then. 

c) There are many ways to reach your goals. 

Find a solution. 

d) Visualize who will do what in your plan like a movie script. 

Consider your movie's actors and script's turning points, then act accordingly. The game continues. 

e) Document your plan so others can judge your progress. 

Accountability boosts success. 

f) Know that a good plan doesn't take much time. 

The execution is usually the hardest part, but most people either don't have a plan or keep changing it. Don't drive while building the car. Build it first, because it'll be bumpy. 

5. Do what is necessary to push through the plans to get results 

a) Great planners without execution fail. 

Life is won with more than just planning. Similarly, practice without talent beats talent without practice. 

b) Work ethic is undervalued. 

Hyper-productivity is praised in corporate America, even if it leads nowhere. To get things done, use checklists, fewer emails, and more desk time. 

c) Set clear metrics to ensure plan adherence. 

I've written about the OKR strategy for organizations with multiple people here. If you're on your own, I recommend the Wheel of Life approach. Both systems start with goals and tasks to achieve them. Then start executing on a realistic timeline. 

If you find solutions, weaknesses don't matter. 

Everyone's weak. You, me, Gates, Dalio, even Musk. Nobody will be great at all 5 steps of the system because no one can think in all the ways required. Some are good at analyzing and diagnosing but bad at executing. Some are good planners but poor communicators. Others lack self-discipline. 

Stay humble and ask for help when needed. Nobody has ever succeeded 100% on their own, without anyone else's help. That's the paradox of individual success: teamwork is the only way to get there. 

Most people won't have the skills to execute even the best plan. You can get missing skills in two ways: 

1. Self-taught (time-consuming) 

2. Others' (requires humility) light

On knowing what to do with your life 

“Some people have good mental maps and know what to do on their own. Maybe they learned them or were blessed with common sense. They have more answers than others. Others are more humble and open-minded. […] Open-mindedness and mental maps are most powerful.” — Ray Dalio 

I've always known what I wanted to do, so I'm lucky. I'm almost 30 and have always had trouble executing. Good thing I never stopped experimenting, but I never committed to anything long-term. I jumped between projects. I decided 3 years ago to stick to one project for at least 6 months and haven't looked back. 

Maybe you're good at staying focused and executing, but you don't know what to do. Maybe you have none of these because you haven't found your purpose. Always try new projects and talk to as many people as possible. It will give you inspiration and ideas and set you up for success. 

There is almost always a way to achieve a crazy goal or idea. 

Enjoy the journey, whichever path you take.

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.