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.

Failures inspire young developers

Jason citron created many products.

These products flopped.

Microsoft offered $10 billion for one of these products.

He rejected the offer since he was so confident in his success.

Let’s find out how he built a product that is currently valued at $15 billion.

Early in his youth, Jason began learning to code.

Jason's father taught him programming and IT.

His father wanted to help him earn money when he needed it.

Jason created video games and websites in high school.

Jason realized early on that his IT and programming skills could make him money.

Jason's parents misjudged his aptitude for programming.

Jason frequented online programming communities.

He looked for web developers. He created websites for those people.

His parents suspected Jason sold drugs online. When he said he used programming to make money, they were shocked.

They helped him set up a PayPal account.

Florida higher education to study video game creation

Jason never attended an expensive university.

He studied game design in Florida.

“Higher Education is an interesting part of society… When I work with people, the school they went to never comes up… only thing that matters is what can you do…At the end of the day, the beauty of silicon valley is that if you have a great idea and you can bring it to the life, you can convince a total stranger to give you money and join your project… This notion that you have to go to a great school didn’t end up being a thing for me.”

Jason's life was altered by Steve Jobs' keynote address.

After graduating, Jason joined an incubator.

Jason created a video-dating site first.

Bad idea.

Nobody wanted to use it when it was released, so they shut it down.

He made a multiplayer game.

It was released on Bebo. 10,000 people played it.

When Steve Jobs unveiled the Apple app store, he stopped playing.

The introduction of the app store resembled that of a new gaming console.

Jason's life altered after Steve Jobs' 2008 address.

“Whenever a new video game console is launched, that’s the opportunity for a new video game studio to get started, it’s because there aren’t too many games available…When a new PlayStation comes out, since it’s a new system, there’s only a handful of titles available… If you can be a launch title you can get a lot of distribution.”

Apple's app store provided a chance to start a video game company.

They released an app after 5 months of work.

Aurora Feint is the game.

Jason believed 1000 players in a week would be wonderful. A thousand players joined in the first hour.

Over time, Aurora Feints' game didn't gain traction. They don't make enough money to keep playing.

They could only make enough for one month.

Instead of buying video games, buy technology

Jason saw that they established a leaderboard, chat rooms, and multiplayer capabilities and believed other developers would want to use these.

They opted to sell the prior game's technology.

OpenFeint.

Assisting other game developers

They had no money in the bank to create everything needed to make the technology user-friendly.

Jason and Daniel designed a website saying:

“If you’re making a video game and want to have a drop in multiplayer support, you can use our system”

TechCrunch covered their website launch, and they gained a few hundred mailing list subscribers.

They raised seed funding with the mailing list.

Nearly all iPhone game developers started adopting the Open Feint logo.

“It was pretty wild… It was really like a whole social platform for people to play with their friends.”

What kind of a business model was it?

OpenFeint originally planned to make the software free for all games. As the game gained popularity, they demanded payment.

They later concluded it wasn't a good business concept.

It became free eventually.

Acquired for $104 million

Open Feint's users and employees grew tremendously.

GREE bought OpenFeint for $104 million in April 2011.

GREE initially committed to helping Jason and his team build a fantastic company.

Three or four months after the acquisition, Jason recognized they had a different vision.

He quit.

Jason's Original Vision for the iPad

Jason focused on distribution in 2012 to help businesses stand out.

The iPad market and user base were growing tremendously.

Jason said the iPad may replace mobile gadgets.

iPad gamers behaved differently than mobile gamers.

People sat longer and experienced more using an iPad.

“The idea I had was what if we built a gaming business that was more like traditional video games but played on tablets as opposed to some kind of mobile game that I’ve been doing before.”

Unexpected insight after researching the video game industry

Jason learned from studying the gaming industry that long-standing companies had advantages beyond a single release.

Previously, long-standing video game firms had their own distribution system. This distribution strategy could buffer time between successful titles.

Sony, Microsoft, and Valve all have gaming consoles and online stores.

So he built a distribution system.

He created a group chat app for gamers.

He envisioned a team-based multiplayer game with text and voice interaction.

His objective was to develop a communication network, release more games, and start a game distribution business.

Remaking the video game League of Legends

Jason and his crew reimagined a League of Legends game mode for 12-inch glass.

They adapted the game for tablets.

League of Legends was PC-only.

So they rebuilt it.

They overhauled the game and included native mobile experiences to stand out.

Hammer and Chisel was the company's name.

18 people worked on the game.

The game was funded. The game took 2.5 years to make.

Was the game a success?

July 2014 marked the game's release. The team's hopes were dashed.

Critics initially praised the game.

Initial installation was widespread.

The game failed.

As time passed, the team realized iPad gaming wouldn't increase much and mobile would win.

Jason was given a fresh idea by Stan Vishnevskiy.

Stan Vishnevskiy was a corporate engineer.

He told Jason about his plan to design a communication app without a game.

This concept seeded modern strife.

“The insight that he really had was to put a couple of dots together… we’re seeing our customers communicating around our own game with all these different apps and also ourselves when we’re playing on PC… We should solve that problem directly rather than needing to build a new game…we should start making it on PC.”

So began Discord.

Online socializing with pals was the newest trend.

Jason grew up playing video games with his friends.

He never played outside.

Jason had many great moments playing video games with his closest buddy, wife, and brother.

Discord was about providing a location for you and your group to speak and hang out.

Like a private cafe, bedroom, or living room.

Discord was developed for you and your friends on computers and phones.

You can quickly call your buddies during a game to conduct a conference call. Put the call on speaker and talk while playing.

Discord wanted to give every player a unique experience. Because coordinating across apps was a headache.

The entire team started concentrating on Discord.

Jason decided Hammer and Chisel would focus on their chat app.

Jason didn't want to make a video game.

How Discord attracted the appropriate attention

During the first five months, the entire team worked on the game and got feedback from friends.

This ensures product improvement. As a result, some teammates' buddies started utilizing Discord.

The team knew it would become something, but the result was buggy. App occasionally crashed.

Jason persuaded a gamer friend to write on Reddit about the software.

New people would find Discord. Why not?

Reddit users discovered Discord and 50 started using it frequently.

Discord was launched.

Rejecting the $10 billion acquisition proposal

Discord has increased in recent years.

It sends billions of messages.

Discord's users aren't tracked. They're privacy-focused.

Purchase offer

Covid boosted Discord's user base.

Weekly, billions of messages were transmitted.

Microsoft offered $10 billion for Discord in 2021.

Jason sold Open Feint for $104m in 2011.

This time, he believed in the product so much that he rejected Microsoft's offer.

“I was talking to some people in the team about which way we could go… The good thing was that most of the team wanted to continue building.”

Last time, Discord was valued at $15 billion.

Discord raised money on March 12, 2022.

The $15 billion corporation raised $500 million in 2021.

Writing for readers:

14 years of daily writing.

I post practically everything on social media. I authored hundreds of articles, thousands of tweets, and numerous volumes to almost no one.

Tens of thousands of readers regularly praise me.

I despised writing. I'm stuck now.

I've learned what readers like and what doesn't.

Here are some essential guidelines for writing with impact:

Readers won't understand your work if you can't.

Though obvious, this slipped me up. Share your truths.

Stories engage human brains.

Showing the journey of a person from worm to butterfly inspires the human spirit.

Overthinking hinders powerful writing.

The best ideas come from inner understanding in between thoughts.

Avoid writing to find it. Write.

Writing a masterpiece isn't motivating.

Write for five minutes to simplify. Step-by-step, entertaining, easy steps.

Good writing requires a willingness to make mistakes.

So write loads of garbage that you can edit into a good piece.

Courageous writing.

A courageous story will move readers. Personal experience is best.

Go where few dare.

Templates, outlines, and boundaries help.

Limitations enhance writing.

Excellent writing is straightforward and readable, removing all the unnecessary fat.

Use five words instead of nine.

Use ordinary words instead of uncommon ones.

Readers desire relatability.

Too much perfection will turn it off.

Write to solve an issue if you can't think of anything to write.

Instead, read to inspire. Best authors read.

Every tweet, thread, and novel must have a central idea.

What's its point?

This can make writing confusing.

️ Don't direct your reader.

Readers quit reading. Demonstrate, describe, and relate.

Even if no one responds, have fun. If you hate writing it, the reader will too.

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.

Wishing for Lasting Companies, Not Penny Stocks or Goodwill Write-Downs

Get me a NASCAR-style company-logoed cremation urn (notice to the executor of my will, theres gonna be a lot of weird requests). I believe in working on projects that would be on your tombstone. As the Homebrew logo is tattooed on my shoulder, expanding the portfolio to my posthumous commemoration is easy. But this isn't an IRR victory lap; it's a hope that the firms we worked for would last beyond my lifetime.

Venture investors too often take credit or distance themselves from startups based on circumstances. Successful companies tell stories of crucial introductions, strategy conversations, and other value. Defeats Even whether our term involves Board service or systematic ethical violations, I'm just a little investment, so there's not much I can do. Since I'm guilty, I'm tossing stones from within the glass home (although we try to own our decisions through the lifecycle).

Post-exit company trajectories are usually unconfounded. Off the cap table, no longer a shareholder (or a diminishing one as you sell off/distribute), eventually leaving the Board. You can cheer for the squad or forget about it, but you've freed the corporation and it's back to portfolio work.

As I look at the downward track of most SPACs and other tarnished IPOs from the last few years, I wonder how I would feel if those were my legacy. Is my job done? Yes. When investing in a business, the odds are against it surviving, let alone thriving and being able to find sunlight. SPAC sponsors, institutional buyers, retail investments. Free trade in an open market is their right. Risking and losing capital is the system working! But

We were lead or co-lead investors in our first three funds, but as additional VCs joined the company, we were pushed down the cap table. Voting your shares rarely matters; supporting the firm when they need it does. Being valuable, consistent, and helping the company improve builds trust with the founders.

I hope every startup we sponsor becomes a successful public company before, during, and after we benefit. My perspective of American capitalism. Well, a stock ticker has a lot of garbage, and I support all types of regulation simplification (in addition to being a person investor in the Long-Term Stock Exchange). Yet being owned by a large group of investors and making actual gains for them is great. Likewise does seeing someone you met when they were just starting out become a public company CEO without losing their voice, leadership, or beliefs.

I'm just thinking about what we can do from the start to realize value from our investments and build companies with bright futures. Maybe seed venture financing shouldn't impact those outcomes, but I'm not comfortable giving up that obligation.

Prioritize big-ticket purchases

I've made several spending blunders. I get sick thinking about how much money I spent.

My financial mental model was poor back then.

Stoicism and mindfulness keep me from attaching to those feelings. It still hurts.

Until four or five years ago, I bought a new winter jacket every year.

Ten years ago, I spent twice as much. Now that I have a fantastic, warm winter parka, I don't even consider acquiring another one. No more spending. I'm not looking for jackets either.

Saving time and money by spending well is my thinking paradigm.

The philosophy is expressed in most languages. Cheap is expensive in the Netherlands. This applies beyond shopping.

In this essay, I will offer three examples of how this mental paradigm transformed my financial life.

Publishing books

In 2015, I presented and positioned my first book poorly.

I called the book Huge Life Success and made a funny Canva cover in 30 minutes. This:

That looks nothing like my present books. No logo or style. The book felt amateurish.

The book started bothering me a few weeks after publication. The advice was good, but it didn't appear professional. I studied the book business extensively.

I created a style for all my designs. Branding. Win Your Inner Wars was reissued a year later.

Title, cover, and description changed. Rearranging the chapters improved readability.

Seven years later, the book sells hundreds of copies a month. That taught me a lot.

Rushing to finish a project is enticing. Send it and move forward.

Avoid rushing everything. Relax. Develop your projects. Perform well. Perform the job well.

My first novel was underfunded and underworked. A bad book arrived. I then invested time and money in writing the greatest book I could.

That book still sells.

Traveling

I hate travel. Airports, flights, trains, and lines irritate me.

But, I enjoy traveling to beautiful areas.

I do it strangely. I make up travel rules. I never go to airports in summer. I hate being near airports on holidays. Unworthy.

No vacation packages for me. Those airline packages with a flight, shuttle, and hotel. I've had enough.

I try to avoid crowds and popular spots. July Paris? Nuts and bolts, please. Christmas in NYC? No, please keep me sane.

I fly business class behind. I accept upgrades upon check-in. I prefer driving. I drove from the Netherlands to southern Spain.

Thankfully, no lines. What if travel costs more? Thus? I enjoy it from the start. I start traveling then.

I rarely travel since I'm so difficult. One great excursion beats several average ones.

Personal effectiveness

New apps, tools, and strategies intrigue most productivity professionals.

No.

I researched years ago. I spent years investigating productivity in university.

I bought books, courses, applications, and tools. It was expensive and time-consuming.

Im finished. Productivity no longer costs me time or money. OK. I worked on it once and now follow my strategy.

I avoid new programs and systems. My stuff works. Why change winners?

Spending wisely saves time and money.

Spending wisely means spending once. Many people ignore productivity. It's understudied. No classes.

Some assume reading a few articles or a book is enough. Productivity is personal. You need a personal system.

Time invested is one-time. You can trust your system for life once you find it.

Concentrate on the expensive choices.

Life's short. Saving money quickly is enticing.

Spend less on groceries today. True. That won't fix your finances.

Adopt a lifestyle that makes you affluent over time. Consider major choices.

Are they causing long-term poverty? Are you richer?

Leasing cars comes to mind. The automobile costs a fortune today. The premium could accomplish a million nice things.

Focusing on important decisions makes life easier. Consider your future. You want to improve next year.