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.

I placed a link on HackerNews and got 300 signups in a week. This post explains what happened.

Product Concept

The product is DbSchemaLibrary. A library of Database Schema.

I'm not sure where this idea originated from. Very fast. Build fast, fail fast, test many ideas, and one will be a hit. I tried it. Let's try it anyway, even though it'll probably fail. I finished The Lean Startup book and wanted to use it.

Database job bores me. Important! I get drowsy working on it. Someone must do it. I remember this happening once. I needed examples at the time. Something similar to Recall (my other project) that I can copy — or at least use as a reference.

Frequently googled. Many tabs open. The results were useless. I raised my hand and agreed to construct the database myself.

It resurfaced. I decided to do something.

Due Diligence

Lean Startup emphasizes validated learning. Everything the startup does should result in learning. I may build something nobody wants otherwise. That's what happened to Recall.

So, I wrote a business plan document. This happens before I code. What am I solving? What is my proposed solution? What is the leap of faith between the problem and solution? Who would be my target audience?

My note:

In my previous project, I did the opposite!

I wrote my expectations after reading the book's advice.

“Failure is a prerequisite to learning. The problem with the notion of shipping a product and then seeing what happens is that you are guaranteed to succeed — at seeing what happens.” — The Lean Startup book

These are successful metrics. If I don't reach them, I'll drop the idea and try another. I didn't understand numbers then. Below are guesses. But it’s a start!

I then wrote the project's What and Why. I'll use this everywhere. Before, I wrote a different pitch each time. I thought certain words would be better. I felt the audience might want something unusual.

Occasionally, this works. I'm unsure if it's a good idea. No stats, just my writing-time opinion. Writing every time is time-consuming and sometimes hazardous. Having a copy saved me duplication.

I can measure and learn from performance.

Last, I identified communities that might demand the product. This became an exercise in creativity.

The MVP

So now it’s time to build.

A MVP can test my assumptions. Business may learn from it. Not low-quality. We should learn from the tiniest thing.

I like the example of how Dropbox did theirs. They assumed that if the product works, people will utilize it. How can this be tested without a quality product? They made a movie demonstrating the software's functionality. Who knows how much functionality existed?

So I tested my biggest assumption. Users want schema references. How can I test if users want to reference another schema? I'd love this. Recall taught me that wanting something doesn't mean others do.

I made an email-collection landing page. Describe it briefly. Reference library. Each email sender wants a reference. They're interested in the product. Few other reasons exist.

Header and footer were skipped. No name or logo. DbSchemaLibrary is a name I thought of after the fact. 5-minute logo. I expected a flop. Recall has no users after months of labor. What could happen to a 2-day project?

I didn't compromise learning validation. How many visitors sign up? To draw a conclusion, I must track these results.

Posting Time

Now that the job is done, gauge interest. The next morning, I posted on all my channels. I didn't want to be spammy, therefore it required more time.

I made sure each channel had at least one fan of this product. I also answer people's inquiries in the channel.

My list stinks. Several channels wouldn't work. The product's target market isn't there. Posting there would waste our time. This taught me to create marketing channels depending on my persona.

Statistics! What actually happened

My favorite part! 23 channels received the link.

I stopped posting to Discord despite its high conversion rate. I eliminated some channels because they didn't fit. According to the numbers, some users like it. Most users think it's spam.

I was skeptical. And 12 people viewed it.

I didn't expect much attention on a startup subreddit. I'll likely examine Reddit further in the future. As I have enough info, I didn't post much. Time for the next validated learning

No comment. The post had few views, therefore the numbers are low.

The targeted people come next.

I'm a Toptal freelancer. There's a member-only Slack channel. Most people can't use this marketing channel, but you should! It's not as spectacular as discord's 27% conversion rate. But I think the users here are better.

I don’t really have a following anywhere so this isn’t something I can leverage.

The best yet. 10% is converted. With more data, I expect to attain a 10% conversion rate from other channels. Stable number.

This number required some work. Did you know that people use many different clients to read HN?

Unknowns

Untrackable views and signups abound. 1136 views and 135 signups are untraceable. It's 11%. I bet much of that came from Hackernews.

Overall Statistics

The 7-day signup-to-visit ratio was 17%. (Hourly data points)

First-day percentages were lower, which is noteworthy. Initially, it was little above 10%. The HN post started getting views then.

When traffic drops, the number reaches just around 20%. More individuals are interested in the connection. hn.algolia.com sent 2 visitors. This means people are searching and finding my post.

Interesting discoveries

1. HN post struggled till the US woke up.

11am UTC. After an hour, it lost popularity. It seemed over. 7 signups converted 13%. Not amazing, but I would've thought ahead.

After 4pm UTC, traffic grew again. 4pm UTC is 9am PDT. US awakened. 10am PDT saw 512 views.

2. The product was highlighted in a newsletter.

I found Revue references when gathering data. Newsletter platform. Someone posted the newsletter link. 37 views and 3 registrations.

3. HN numbers are extremely reliable

I don't have a time-lapse graph (yet). The statistics were constant all day.

• 2717 views later 272 new users, or 10.1%

• With 293 signups at 2856 views, 10.25%

• At 306 signups at 2965 views, 10.32%

Learnings

1. My initial estimations were wildly inaccurate

I wrote 30% conversion. Reading some articles, looks like 10% is a good number to aim for.

2. Paying attention to what matters rather than vain metrics

The Lean Startup discourages vanity metrics. Feel-good metrics that don't measure growth or traction. Considering the proportion instead of the total visitors made me realize there was something here.

What’s next?

There are lots of work to do. Data aggregation, display, website development, marketing, legal issues. Fun! It's satisfying to solve an issue rather than investigate its cause.

In the meantime, I’ve already written the first project update in another post. Continue reading it if you’d like to know more about the project itself! Shifting from Quantity to Quality — DbSchemaLibrary

In 8 months, I doubled my audience with them.

LinkedIn's buzz isn't over.

People dream of social proof every day. They want clients, interesting jobs, and field recognition.

LinkedIn coaches will benefit greatly. Sell learning? Probably. Can you use it?

Consistency has been key in my eight-month study of LinkedIn. However, I'll share seven of my tips. 700 to 4500 people followed me.

1. Communication, communication, communication

LinkedIn is a social network. I like to think of it as a cafe. Here, you can share your thoughts, meet friends, and discuss life and work.

Do not treat LinkedIn as if it were a board for your post-its.

More socializing improves relationships. It's about people, like any network.

Consider interactions. Three main areas:

• Respond to criticism left on your posts.

• Comment on other people's posts

• Start and maintain conversations through direct messages.

Engage people. You spend too much time on Facebook if you only read your wall. Keeping in touch and having meaningful conversations helps build your network.

Every day, start a new conversation to make new friends.

2. Stick with those you admire

Interact thoughtfully.

Choose your contacts. Build your tribe is a term. Respectful networking.

I only had past colleagues, family, and friends in my network at the start of this year. Not business-friendly. Since then, I've sought out people I admire or can learn from.

Finding a few will help you. As they connect you to their networks. Friendships can lead to clients.

Don't underestimate network power. Cafe-style. Meet people at each table. But avoid people who sell SEO, web redesign, VAs, mysterious job opportunities, etc.

3. Share eye-catching infographics

Daily infographics flood LinkedIn. Visuals are popular. Use Canva's free templates if you can't draw them.

Last week's:

It's a fun way to visualize your topic.

You can repost and comment on infographics. Involve your network. I prefer making my own because I build my brand around certain designs.

My friend posted infographics consistently for four months and grew his network to 30,000.

If you start, credit the authors. As you steal someone's work.

4. Invite some friends over.

LinkedIn alone can be lonely. Having a few friends who support your work daily will boost your growth.

I was lucky to be invited to a group of networkers. We share knowledge and advice.

Having a few regulars who can discuss your posts is helpful. It's artificial, but it works and engages others.

Consider who you'd support if they were in your shoes.

You can pay for an engagement group, but you risk supporting unrelated people with rubbish posts.

Help each other out.

5. Don't let your feed or algorithm divert you.

LinkedIn's algorithm is magical.

Which time is best? How fast do you need to comment? Which days are best?

Overemphasize algorithms. Consider the user. No need to worry about the best time.

Remember to spend time on LinkedIn actively. Not passively. That is what Facebook is for.

Surely someone would find a LinkedIn recipe. Don't beat the algorithm yet. Consider your audience.

6. The more personal, the better

Personalization isn't limited to selfies. Share your successes and failures.

The more personality you show, the better.

People relate to others, not theories or quotes. Why should they follow you? Everyone posts the same content?

Consider your friends. What's their appeal?

Because they show their work and identity. It's simple. Medium and Linkedin are your platforms. Find out what works.

You can copy others' hooks and structures. You decide how simple to make it, though.

7. Have fun with those who have various post structures.

I like writing, infographics, videos, and carousels. Because you can:

Repurpose your content!

Out of one blog post I make:

• Newsletter

• Infographics (positive and negative points of view)

• Carousel

• Personal stories

• Listicle

Create less but more variety. Since LinkedIn posts last 24 hours, you can rotate the same topics for weeks without anyone noticing.

Effective!

The final LI snippet to think about

LinkedIn is about consistency. Some say 15 minutes. If you're serious about networking, spend more time there.

The good news is that it is worth it. The bad news is that it takes time.

After 10 years of working in scale-ups, I've embraced a few concepts for scaling Tech and Product teams.

First, cross-functionalize teams. Product Managers represent the business, Product Designers the consumer, and Engineers build.

I organize teams of 5-10 individuals, following AWS's two pizza teams guidelines, with a Product Trio guiding each.

If more individuals are needed to reach a goal, I group teams under a Product Trio.

With Engineering being the biggest group, Staff/Principal Engineers often support the Trio on cross-team technical decisions.

Product Managers, Engineering Managers, or Engineers in the team may manage projects (depending on the project or aim), but the trio is collectively responsible for the team's output and outcome.

Once the Product Trio model is created, roles, duties, team ceremonies, and cooperation models must be clarified.

Keep reporting lines by discipline. Line managers are accountable for each individual's advancement, thus it's crucial that they know the work in detail.

Cross-team collaboration becomes more important after 3 teams (15-30 people). Teams can easily diverge in how they write code, run ceremonies, and build products.

Establishing groups of people that are cross-team, but grouped by discipline and skills, sharing and agreeing on working practices becomes critical.

The “Spotify Guild” model has been where I’ve taken a lot of my inspiration from.

Last, establish a taxonomy for communication channels.

In Slack, I create one channel per team and one per guild (and one for me to have discussions with the team leads).

These are just some of the basic principles I follow to organize teams.

A book I particularly like about team types and how they interact with each other is https://teamtopologies.com/.

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!