Dharmesh Shah co-founded HubSpot. WordPlay reached $90,000 per month in revenue without utilizing any of his wealth.

His method:

Take Advantage Of An Established Trend

Remember Wordle? Dharmesh was instantly hooked. As was the tech world.

HubSpot's co-founder noted inefficiencies in a recent My First Million episode. He wanted to play daily. Dharmesh, a tinkerer and software engineer, decided to design a word game.

He's a billionaire. How could he?

1. Wordle had limitations in his opinion;

2. Dharmesh is fundamentally a developer. He desired to start something new and increase his programming knowledge;

3. This project may serve as an excellent illustration for his son, who had begun learning about software development.

Better It Up

Building a new Wordle wasn't successful.

WordPlay lets you play with friends and family. You could challenge them and compare the results. It is a built-in growth tool.

WordPlay features:

• the capacity to follow sophisticated statistics after creating an account;

• continuous feedback on your performance;

• Outstanding domain name (wordplay.com).

Project Development

WordPlay has 9.5 million visitors and 45 million games played since February.

HubSpot co-founder credits tremendous growth to flywheel marketing, pushing the game through his own following.

Choosing an exploding specialty and making sharing easy also helped.

Shah enabled Google Ads on the website to test earning potential. Monthly revenue was $90,000.

That's just Google Ads. If monetization was the goal, a specialized ad network like Ezoic could double or triple the amount.

Wordle was a great buy for The New York Times at $1 million.

Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.

Inspired by someone I never met

Inspiration is good and bad.

Paul Jarvis inspires me. He's a web person and writer who created his own category by being himself.

Paul said no thank you when everyone else was developing, building, and assuming greater responsibilities. This isn't success. He rewrote the rules. Working for himself, expanding at his own speed, and doing what he loves were his definitions of success.

Play with a problem that you have

The biggest problem can be not recognizing a problem.

Acceptance without question is deception. When you don't push limits, you forget how. You start thinking everything must be as it is.

For example: working. Paul worked a 9-5 agency work with little autonomy. He questioned whether the 9-5 was a way to live, not the way.

Another option existed. So he chipped away at how to live in this new environment.

Don't simply jump

Internet writers tell people considering quitting 9-5 to just quit. To throw in the towel. To do what you like.

The advice is harmful, despite the good intentions. People think quitting is hard. Like courage is the issue. Like handing your boss a resignation letter.

Nope. The tough part comes after. It’s easy to jump. Landing is difficult.

The landing

Paul didn't quit. Intelligent individuals don't. Smart folks focus on landing. They imagine life after 9-5.

Paul had been a web developer for a long time, had solid clients, and was respected. Hence if he pushed the limits and discovered another route, he had the potential to execute.

Working on the side

Society loves polarization. It’s left or right. Either way. Or chaos. It's 9-5 or entrepreneurship.

But like Paul, you can stretch polarization's limits. In-between exists.

You can work a 9-5 and side jobs (as I do). A mix of your favorites. The 9-5's stability and creativity. Fire and routine.

Remember you can't have everything but anything. You can create and work part-time.

My hybrid lifestyle

Not selling books doesn't destroy my world. My globe keeps spinning if my new business fails or if people don't like my Tweets. Unhappy algorithm? Cool. I'm not bothered (okay maybe a little).

The mix gives me the best of both worlds. To create, hone my skill, and grasp big-business basics. I like routine, but I also appreciate spending 4 hours on Saturdays writing.

Some days I adore leaving work at 5 pm and disconnecting. Other days, I adore having a place to write if inspiration strikes during a run or a discussion.

I’m a part-time creator

I’m a part-time creator. No, I'm not trying to quit. I don't work 5 pm - 2 am on the side. No, I'm not at $10,000 MRR.

I work part-time but enjoy my 9-5. My 9-5 has goodies. My side job as well.

It combines both to meet my lifestyle. I'm satisfied.

Join the Part-time Creators Club for free here. I’ll send you tips to enhance your creative game.

What does Ukraine's murderous craziness mean?

Vladimir Putin expressed his patience to Israeli Prime Minister Naftali Bennet. Thousands, even hundreds of thousands of young and middle-aged males in his country have no meaning to him.

During a meeting in March with Prime Minister Naftali Bennett of Israel, Mr. Putin admitted that the Ukrainians were tougher “than I was told,” according to two people familiar with the exchange. “This will probably be much more difficult than we thought. But the war is on their territory, not ours. We are a big country and we have patience (The Inside Story of a Catastrophe).”

Putin should explain to Russian mothers how patient he is with his invasion of Ukraine.

Putin is rich. Even while sanctions have certainly limited Putin's access to his fortune, he has access to everything in Russia. Unlimited wealth.

The Russian leader's infrastructure was designed with his whims in mind. Vladimir Putin is one of the wealthiest and most catered-to people alive. He's also all-powerful, as his lack of opposition shows. His incredible wealth and power have isolated him from average people so much that he doesn't mind turning lives upside down to prove a point.

For many, losing a Russian spouse or son is painful. Whether the soldier was a big breadwinner or unemployed, the loss of a male figure leaves many families bewildered and anxious. Putin, Russia's revered president, seems unfazed.

People who know Mr. Putin say he is ready to sacrifice untold lives and treasure for as long as it takes, and in a rare face-to-face meeting with the Americans last month the Russians wanted to deliver a stark message to President Biden: No matter how many Russian soldiers are killed or wounded on the battlefield, Russia will not give up (The Inside Story of a Catastrophe).

Imagine a country's leader publicly admitting a mistake he's made. Imagine getting Putin's undivided attention.

So, I underestimated Ukrainians. I can't allow them make me appear terrible, so I'll utilize as many drunken dopes as possible to cover up my error. They'll die fulfilled and heroic.

Russia's human resources are limited, but its willingness to cause suffering is not. How many Russian families must die before the curse is broken? If mass protests started tomorrow, Russia's authorities couldn't stop them.

When Moscovites faced down tanks in August 1991, the Gorbachev coup ended in three days. Even though few city residents showed up, everything collapsed. This wicked disaster won't require many Russians.

One NATO member is warning allies that Mr. Putin is ready to accept the deaths or injuries of as many as 300,000 Russian troops — roughly three times his estimated losses so far.

If 100,000 Russians have died in Ukraine and Putin doesn't mind another 200,000 dying, why don't these 200,000 ghosts stand up and save themselves? Putin plays the role of concerned and benevolent leader effectively, but things aren't going well for Russia.

What would 300,000 or more missing men signify for Russia's future? How many kids will have broken homes? How many families won't form, and what will the economy do?

Putin reportedly cared about his legacy. His place in Russian history Putin's invasion of Ukraine settled his legacy. He has single-handedly weakened and despaired Russia since the 1980s.

Putin will be viewed by sensible people as one of Russia's worst adversaries, but Russians will think he was fantastic despite Ukraine.

The more setbacks Mr. Putin endures on the battlefield, the more fears grow over how far he is willing to go. He has killed tens of thousands in Ukraine, leveled cities, and targeted civilians for maximum pain — obliterating hospitals, schools, and apartment buildings while cutting off power and water to millions before winter. Each time Ukrainian forces score a major blow against Russia, the bombing of their country intensifies. And Mr. Putin has repeatedly reminded the world that he can use anything at his disposal, including nuclear arms, to pursue his notion of victory.

How much death and damage will there be in Ukraine if Putin sends 200,000 more Russians to the front? It's scary, sad, and sick.

Monster.

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.