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.

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.

Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.

Round size

Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.

Valuation

There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.

Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.

I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.

ARR

Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.

Capitalization Rate

2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:

The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR

What next?

No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

Genius or lucky?

From the title, you might think I'm selling advertising for a financial influencer, a dubious trading site, or a training organization to attract clients. I'm suspicious. Better safe than sorry.

But not here.

Jake Freeman, 20, made $110 million in a month, according to the Financial Times. At 18, he ran for president. He made his name in markets, not politics. Two years later, he's Wall Street's prince. Interview requests flood the prodigy.

Jake Freeman bought 5 million Bed Bath & Beyond Group shares for $5.5 in July 2022 and sold them for $27 a month later. He thought the stock might double. Since speculation died down, he sold well. The stock fell 40.5% to 11 dollars on Friday, 19 August 2022. On August 22, 2022, it fell 16% to $9.

Smallholders have been buying the stock for weeks and will lose heavily if it falls further. Bed Bath & Beyond is the second most popular stock after Foot Locker, ahead of GameStop and Apple.

Jake Freeman earned $110 million thanks to a significant stock market flurry.

Online broker customers aren't the only ones with jitters. By June 2022, Ken Griffin's Citadel and Stephen Mandel's Lone Pine Capital held nearly a third of the company's capital. Did big managers sell before the stock plummeted?

Recent stock movements (derivatives) and rumors could prompt a SEC investigation.

Jake Freeman wrote to the board of directors after his investment to call for a turnaround, given the company's persistent problems and short sellers. The bathroom and kitchen products distribution group's stock soared in July 2022 due to renewed buying by private speculators, who made it one of their meme stocks with AMC and GameStop.

Second-quarter 2022 results and financial health worsened. He didn't celebrate his miraculous operation in a nightclub. He told a British newspaper, "I'm shocked." His parents dined in New York. He returned to Los Angeles to study math and economics.

Jake Freeman founded Freeman Capital Management with his savings and $25 million from family, friends, and acquaintances. They are the ones who are entitled to the $110 million he raised in one month. Will his investors pocket and withdraw all or part of their profits or will they trust the young prodigy for new stunts on Wall Street?

His operation should attract new clients. Well-known hedge funds may hire him.

Jake Freeman didn't listen to gurus or former traders. At 17, he interned at a quantitative finance and derivatives hedge fund, Volaris. At 13, he began investing with his pharmaceutical executive uncle. All countries have increased their Google searches for the young trader in the last week.

Naturally, his success has inspired resentment.

His success stirs jealousy, and he's attacked on social media. On Reddit, people who lost money on Bed Bath & Beyond, Jake Freeman's fortune, are mourning.

Several conspiracy theories circulate about him, including that he doesn't exist or is working for a Taiwanese amusement park.

If all 20 million American students had the same trading skills, they would have generated $1.46 trillion. Jake Freeman is unique. Apprentice traders' careers are often short, disillusioning, and tragic.

Two years ago, 20-year-old Robinhood client Alexander Kearns committed suicide after losing $750,000 trading options. Great traders start young. Michael Platt of BlueCrest invested in British stocks at age 12 under his grandmother's supervision and made a £30,000 fortune. Paul Tudor Jones started trading before he turned 18 with his uncle. Warren Buffett, at age 10, was discussing investments with Goldman Sachs' head. Oracle of Omaha tells all.

Technical books aren't like novels. We need a new approach to technical texts. I've spent years looking for a decent reading method. I tried numerous ways before finding one that worked. This post explains how I read technical books efficiently.

What Do I Mean When I Say Effective?

Effectiveness depends on the book. Effective implies I know where to find answers after reading a reference book. Effective implies I learned the book's knowledge after reading it.

I use reference books as tools in my toolkit. I won't carry all my tools; I'll merely need them. Non-reference books teach me techniques. I never have to make an effort to use them since I always have them.

Reference books I like:

• Design Patterns: Elements of Reusable Object-Oriented Software

• Refactoring: Improving the Design of Existing Code 
  You can also check My Top Takeaways from Refactoring here.

• Practical Object-Oriented Design in Ruby: An Agile Primer

Non-reference books I like:

• The Pragmatic Programmer: your journey to mastery

• Clean Code: A Handbook of Agile Software Craftsmans

The Approach

Technical books might be overwhelming to read in one sitting. Especially when you have no idea what is coming next as you read. When you don't know how deep the rabbit hole goes, you feel lost as you read. This is my years-long method for overcoming this difficulty.

Whether you follow the step-by-step guide or not, remember these:

• Understand the terminology. Make sure you get the meaning of any terms you come across more than once. The likelihood that a term will be significant increases as you encounter it more frequently.

• Know when to stop. I've always believed that in order to truly comprehend something, I must delve as deeply as possible into it. That, however, is not usually very effective. There are moments when you have to draw the line and start putting theory into practice (if applicable).

• Look over your notes. When reading technical books or documents, taking notes is a crucial habit to develop. Additionally, you must regularly examine your notes if you want to get the most out of them. This will assist you in internalizing the lessons you acquired from the book. And you'll see that the urge to review reduces with time.

Let's talk about how I read a technical book step by step.

0. Read the Foreword/Preface

These sections are crucial in technical books. They answer Who should read it, What each chapter discusses, and sometimes How to Read? This is helpful before reading the book. Who could know the ideal way to read the book better than the author, right?

1. Scanning

I scan the chapter. Fast scanning is needed.

• I review the headings.

• I scan the pictures quickly.

• I assess the chapter's length to determine whether I might divide it into more manageable sections.

2. Skimming

Skimming is faster than reading but slower than scanning.

• I focus more on the captions and subtitles for the photographs.

• I read each paragraph's opening and closing sentences.

• I examined the code samples.

• I attempt to grasp each section's basic points without getting bogged down in the specifics.

• Throughout the entire reading period, I make an effort to make mental notes of what may require additional attention and what may not. Because I don't want to spend time taking physical notes, kindly notice that I am using the term "mental" here. It is much simpler to recall. You may think that this is more significant than typing or writing “Pay attention to X.”

• I move on quickly. This is something I considered crucial because, when trying to skim, it is simple to start reading the entire thing.

3. Complete reading

Previous steps pay off.

• I finished reading the chapter.

• I concentrate on the passages that I mentally underlined when skimming.

• I put the book away and make my own notes. It is typically more difficult than it seems for me. But it's important to speak in your own words. You must choose the right words to adequately summarize what you have read. How do those words make you feel? Additionally, you must be able to summarize your notes while you are taking them. Sometimes as I'm writing my notes, I realize I have no words to convey what I'm thinking or, even worse, I start to doubt what I'm writing down. This is a good indication that I haven't internalized that idea thoroughly enough.

• I jot my inquiries down. Normally, I read on while compiling my questions in the hopes that I will learn the answers as I read. I'll explore those issues more if I wasn't able to find the answers to my inquiries while reading the book.

Bonus!

Best part: If you take lovely notes like I do, you can publish them as a blog post with a few tweaks.

Conclusion

This is my learning journey. I wanted to show you. This post may help someone with a similar learning style. You can alter the principles above for any technical material.