Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

One-hour ebook sales, affiliate relationships, and more.

If you follow me, you may know I started a new ebook in August 2022.

Despite publishing on this platform, my website, and Quora, I'm not a writer.

My writing speed is slow, 2,000 words a day, and I struggle to communicate cohesively.

In April 2022, I wrote a successful guide on How to Write Google-Friendly Blog Posts.

I had no email list or social media presence. I've made $1,600+ selling ebooks.

Evidence:

My first digital offering isn't a book.

It's an actionable guide with my tried-and-true process for writing Google-friendly content.

I'm not bragging.

Established authors like Tim Denning make more from my ebook sales with one newsletter.

This experience taught me writing isn't a privilege.

Writing a book and making money online doesn't require expertise.

Many don't consult experts. They want someone approachable.

Two years passed before I realized my own limits.

I have a brain, two hands, and Internet to spread my message.

I wrote and published a second ebook after the first's success.

On Gumroad, I released my second digital product.

Here's my complete Gumroad evaluation.

Gumroad is a marketplace for content providers to develop and sell sales pages.

Gumroad handles payments and client requests. It's helpful when someone sends a bogus payment receipt requesting an ebook (actual story!).

You'll forget administrative concerns after your first ebook sale.

After my first ebook sale, I did this: I made additional cash!

After every sale, I tell myself, "I built a new semi-passive revenue source."

This thinking shift helps me become less busy while increasing my income and quality of life.

Besides helping others, folks sell evergreen digital things to earn passive money.

It's in my second ebook.

I explain how I built and sold 50+ copies of my SEO writing ebook without being an influencer.

I show how anyone can sell ebooks on Gumroad and automate their sales process.

This is my ebook.

After publicizing the ebook release, I sold three copies within an hour.

Wow, or meh?

I don’t know.

The answer is different for everyone.

These three sales came from a small email list of 40 motivated fans waiting for my ebook release.

I had bigger plans.

I'll market my ebook on Medium, my website, Quora, and email.

I'm testing affiliate partnerships this time.

One of my ebook buyers is now promoting it for 40% commission.

Become my affiliate if you think your readers would like my ebook.

My ebook is a few days old, but I'm interested to see where it goes.

My SEO writing book started without an email list, affiliates, or 4,000 website visitors. I've made four figures.

I'm slowly expanding my communication avenues to have more impact.

Even a small project can open doors you never knew existed.

So began my writing career.

In summary

If you dare, every concept can become a profitable trip.

Before, I couldn't conceive of creating an ebook.

How to Sell eBooks on Gumroad is my second digital product.

Marketing and writing taught me that anything can be sold online.

I've worked in a People role at seven early-stage firms for over 15 years (I enjoy chasing a dream!). Few of the seven achieved profitability, including unicorn status or acquisition.

Did early-stage startups share anything? Was there a difference between winners and losers? YES.

I support founders and entrepreneurs building financially sustainable enterprises with a compelling cause. This isn't something everyone would do. A company's success demands more than guts. Founders drive startup success.

Six Qualities of Successful Startups

Successful startup founders either innately grasped the correlation between strong team engagement and a well-executed business model, or they knew how to ask and listen to others (executive coaches, other company leaders, the team itself) to learn about it.

Successful startups:

1. Co-founders agreed and got along personally.

Multi-founder startups are common. When co-founders agree on strategic decisions and are buddies, there's less friction and politics at work.

As a co-founder, ask your team if you're aligned. They'll explain.

I've seen C-level leaders harbor personal resentments over disagreements. A co-departure founder's caused volatile leadership and work disruptions that the team struggled to manage during and after.

2. Team stayed.

Successful startups have low turnover. Nobody is leaving. There may be a termination for performance, but other team members will have observed the issues and agreed with the decision.

You don't want organizational turnover of 30%+, with leaders citing performance issues but the team not believing them. This breeds suspicion.

Something is wrong if many employees leave voluntarily or involuntarily. You may hear about lack of empowerment, support, or toxic leadership in exit interviews and from the existing team. Intellectual capital loss and resource instability harm success.

3. Team momentum.

A successful startup's team is excited about its progress. Consistently achieving goals and having trackable performance metrics. Some describe this period of productivity as magical, with great talents joining the team and the right people in the right places. Increasing momentum.

I've also seen short-sighted decisions where only some departments, like sales and engineering, had goals. Lack of a unified goals system created silos and miscommunication. Some employees felt apathetic because they didn't know how they contributed to team goals.

4. Employees advanced in their careers.

Even if you haven't created career pathing or professional development programs, early-stage employees will grow and move into next-level roles. If you hire more experienced talent and leaders, expect them to mentor existing team members. Growing companies need good performers.

New talent shouldn't replace and discard existing talent. This creates animosity and makes existing employees feel unappreciated for their early contributions to the company.

5. The company lived its values.

Culture and identity are built on lived values. A company's values affect hiring, performance management, rewards, and other processes. Identify, practice, and believe in company values. Starting with team values instead of management or consultants helps achieve this. When a company's words and actions match, it builds trust.

When company values are beautifully displayed on a wall but few employees understand them, the opposite is true. If an employee can't name the company values, they're useless.

6. Communication was clear.

When necessary information is shared with the team, they feel included, trusted, and like owners. Transparency means employees have the needed information to do their jobs. Disclosure builds trust. The founders answer employees' questions honestly.

Information accessibility decreases office politics. Without transparency, even basic information is guarded and many decisions are made in secret. I've seen founders who don't share financial, board meeting, or compensation and equity information. The founders' lack of trust in the team wasn't surprising, so it was reciprocated.

The Choices

Finally. All six of the above traits (leadership alignment, minimal turnover, momentum, professional advancement, values, and transparency) were high in the profitable startups I've worked at, including unicorn status or acquisition.

I've seen these as the most common and constant signals of startup success or failure.

These characteristics are the product of founders' choices. These decisions lead to increased team engagement and business execution.

Here's something to consider for startup employees and want-to-bes. 90% of startups fail, despite the allure of building something new and gaining ownership. With the emotional and time investment in startup formation, look for startups with these traits to reduce your risk.

Both you and the startup will thrive in these workplaces.

Let's see this once-dominant IT corporation crumble.

What's the capital of Kazakhstan? If you don't know the answer, you can probably find it by Googling. Google Search returned results for Nur-Sultan in 0.66 seconds.

Google is the best search engine I've ever used. Did you know another search engine ruled the Internet? I'm sure you guessed Yahoo!

Google's friendly UI and wide selection of services make it my top choice. Let's explore Yahoo's decline.

Yahoo!

YAHOO stands for Yet Another Hierarchically Organized Oracle. Jerry Yang and David Filo established Yahoo.

Yahoo is primarily a search engine and email provider. It offers News and an advertising platform. It was a popular website in 1995 that let people search the Internet directly. Yahoo began offering free email in 1997 by acquiring RocketMail.

According to a study, Yahoo used Google Search Engine technology until 2000 and then developed its own in 2004.

Yahoo! rejected buying Google for $1 billion

Larry Page and Sergey Brin, Google's founders, approached Yahoo in 1998 to sell Google for $1 billion so they could focus on their studies. Yahoo denied the offer, thinking it was overvalued at the time.

Yahoo realized its error and offered Google $3 billion in 2002, but Google demanded $5 billion since it was more valuable. Yahoo thought $5 billion was overpriced for the existing market.

In 2022, Google is worth $1.56 Trillion.

What happened to Yahoo!

Yahoo refused to buy Google, and Google's valuation rose, making a purchase unfeasible.

Yahoo started losing users when Google launched Gmail. Google's UI was far cleaner than Yahoo's.

Yahoo offered $1 billion to buy Facebook in July 2006, but Zuckerberg and the board sought $1.1 billion. Yahoo rejected, and Facebook's valuation rose, making it difficult to buy.

Yahoo was losing users daily while Google and Facebook gained many. Google and Facebook's popularity soared. Yahoo lost value daily.

Microsoft offered $45 billion to buy Yahoo in February 2008, but Yahoo declined. Microsoft increased its bid to $47 billion after Yahoo said it was too low, but Yahoo rejected it. Then Microsoft rejected Yahoo’s 10% bid increase in May 2008.

In 2015, Verizon bought Yahoo for $4.5 billion, and Apollo Global Management bought 90% of Yahoo's shares for $5 billion in May 2021. Verizon kept 10%.

Yahoo's opportunity to acquire Google and Facebook could have been a turning moment. It declined Microsoft's $45 billion deal in 2008 and was sold to Verizon for $4.5 billion in 2015. Poor decisions and lack of vision caused its downfall. Yahoo's aim wasn't obvious and it didn't stick to a single domain.

Hence, a corporation needs a clear vision and a leader who can see its future.

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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.