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.

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.

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.

https://tomconnor.me/wp-content/uploads/2021/08/10x-Engineer-Mental-Models.pdf

I keep returning to the same mental models and tricks after writing and reading about a wide range of topics.

Top 12 mental models

12.

Survival bias - We perceive the surviving population as remarkable, yet they may have gotten there through sheer grit.

Survivorship bias affects us in many situations. Our retirement fund; the unicorn business; the winning team. We often study and imitate the last one standing. This can lead to genuine insights and performance improvements, but it can also lead us astray because the leader may just be lucky.

11.

The Helsinki Bus Theory - How to persevere Buss up!

Always display new work, and always be compared to others. Why? Easy. Keep riding. Stay on the fucking bus.

10.

Until it sticks… Turning up every day… — Artists teach engineers plenty. Quality work over a career comes from showing up every day and starting.

9.

WRAP decision making process (Heath Brothers)

Decision-making WRAP Model:

W — Widen your Options

R — Reality test your assumptions

A — Attain Distance

P — Prepare to be wrong or Right

8.

Systems for knowledge worker excellence - Todd Henry and Cal Newport write about techniques knowledge workers can employ to build a creative rhythm and do better work.

Todd Henry's FRESH framework:

1. Focus: Keep the start in mind as you wrap up.

2. Relationships: close a loop that's open.

3. Pruning is an energy.

4. Set aside time to be inspired by stimuli.

5. Hours: Spend time thinking.

7.

Black Box Thinking…..

BBT is learning from mistakes. Science has transformed the world because it constantly updates its theories in light of failures. Complexity guarantees failure. Do we learn or self-justify?

6.

The OODA Loop - Competitive advantage

O: Observe: collect the data. Figure out exactly where you are, what’s happening.

O: Orient: analyze/synthesize the data to form an accurate picture.

D: Decide: select an action from possible options

A: Action: execute the action, and return to step (1)

Boyd's approach indicates that speed and agility are about information processing, not physical reactions. They form feedback loops. More OODA loops improve speed.

5.

Know your Domain 

Leaders who try to impose order in a complex situation fail; those who set the stage, step back, and allow patterns to develop win.

https://vimeo.com/640941172?embedded=true&source=vimeo_logo&owner=11999906

4.

The Three Critical Gaps

• Information Gap - The discrepancy between what we know and what we would like to know

• Gap in Alignment - What individuals actually do as opposed to what we wish them to do

• Effects Gap - the discrepancy between our expectations and the results of our actions

3.

Theory of Constraints — The Goal  - To maximize system production, maximize bottleneck throughput.

• Goldratt creates a five-step procedure:

1. Determine the restriction

2. Improve the restriction.

3. Everything else should be based on the limitation.

4. Increase the restriction

5. Go back to step 1 Avoid letting inertia become a limitation.

Any non-constraint improvement is an illusion.

2.

Serendipity and the Adjacent Possible - Why do several amazing ideas emerge at once? How can you foster serendipity in your work?

You need specialized abilities to reach to the edge of possibilities, where you can pursue exciting tasks that will change the world. Few people do it since it takes a lot of hard work. You'll stand out if you do.

Most people simply lack the comfort with discomfort required to tackle really hard things. At some point, in other words, there’s no way getting around the necessity to clear your calendar, shut down your phone, and spend several hard days trying to make sense of the damn proof.

1.

Boundaries of failure - Rasmussen's accident model.

Rasmussen modeled this. It has economic, workload, and performance boundaries.

The economic boundary is a company's profit zone. If the lights are on, you're within the economic boundaries, but there's pressure to cut costs and do more.

Performance limit reflects system capacity. Taking shortcuts is a human desire to minimize work. This is often necessary to survive because there's always more labor.

Both push operating points toward acceptable performance. Personal or process safety, or equipment performance.

If you exceed acceptable performance, you'll push back, typically forcefully.

Great News about the new Google Business Intelligence Solution

Google has renamed Data Studio to Looker Studio and Looker Studio Pro.

Now, Google releases Looker Studio Pro. Similar to the move from Data Studio to Looker Studio, Looker Studio Pro is basically what Looker was previously, but both solutions will merge. Google says the Pro edition will acquire new enterprise management features, team collaboration capabilities, and SLAs.

In addition to Google's announcements and sales methods, additional features include:

Looker Studio assets can now have organizational ownership. Customers can link Looker Studio to a Google Cloud project and migrate existing assets once. This provides:

• Your users' created Looker Studio assets are all kept in a Google Cloud project.

• When the users who own assets leave your organization, the assets won't be removed.

• Using IAM, you may provide each Looker Studio asset in your company project-level permissions.

• Other Cloud services can access Looker Studio assets that are owned by a Google Cloud project.

Looker Studio Pro clients may now manage report and data source access at scale using team workspaces.

Google announcing these features for the pro version is fascinating. Both products will likely converge, but Google may only release many features in the premium version in the future. Microsoft with Power BI and its free and premium variants already achieves this.

Sources and Further Readings

Google, Release Notes (2022)

Google, Looker (2022)

I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!