How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.

Know why it's important.

The entrepreneur I was meeting with said, "I should be doing crypto, or maybe AI? Aren't those the hot spots? I should look there for a startup idea.”

I shook my head. Yes, they're exciting, but that doesn't mean they're best for you and your business.

“There are different types of entrepreneurs?” he asked.

I said "obviously." Two types, actually. Knowing what type of entrepreneur you are helps you build the right startup.

The two types of businesspeople

The best way for me to describe the two types of entrepreneurs is to start by telling you exactly the kinds of entrepreneurial opportunities I never get excited about: future opportunities.

In the early 1990s, my older brother showed me the World Wide Web and urged me to use it. Unimpressed, I returned to my Super Nintendo.

My roommate tried to get me to join Facebook as a senior in college. I remember thinking, This is dumb. Who'll use it?

In 2011, my best friend tried to convince me to buy bitcoin and I laughed.

Heck, a couple of years ago I had to buy a new car, and I never even considered buying something that didn’t require fossilized dinosaur bones.

I'm no visionary. I don't anticipate the future. I focus on the present.

This tendency makes me a problem-solving entrepreneur. I identify entrepreneurial opportunities by spotting flaws and/or inefficiencies in the world and devising solutions.

There are other ways to find business opportunities. Visionary entrepreneurs also exist. I don't mean visionary in the hyperbolic sense that implies world-changing impact. I mean visionary as an entrepreneur who identifies future technological shifts that will change how people work and live and create new markets.

Problem-solving and visionary entrepreneurs are equally good. But the two approaches to building companies are very different. Knowing the type of entrepreneur you are will help you build a startup that fits your worldview.

What is the distinction?

Let's use some simple hypotheticals to compare problem-solving and visionary entrepreneurship.

Imagine a city office building without nearby restaurants. Those office workers love to eat. Sometimes they'd rather eat out than pack a lunch. As an entrepreneur, you can solve the lack of nearby restaurants. You'd open a restaurant near that office, say a pizza parlor, and get customers because you solved the lack of nearby restaurants. Problem-solving entrepreneurship.

Imagine a new office building in a developing area with no residents or workers. In this scenario, a large office building is coming. The workers will need to eat then. As a visionary entrepreneur, you're excited about the new market and decide to open a pizzeria near the construction to meet demand.

Both possibilities involve the same product. You opened a pizzeria. How you launched that pizza restaurant and what will affect its success are different.

Why is the distinction important?

Let's say you opened a pizzeria near an office. You'll probably get customers. Because people are nearby and demand isn't being met, someone from a nearby building will stop in within the first few days of your pizzeria's grand opening. This makes solving the problem relatively risk-free. You'll get customers unless you're a fool.

The market you're targeting existed before you entered it, so you're not guaranteed success. This means people in that market solved the lack of nearby restaurants. Those office workers are used to bringing their own lunches. Why should your restaurant change their habits? Even when they eat out, they're used to traveling far. They've likely developed pizza preferences.

To be successful with your problem-solving startup, you must convince consumers to change their behavior, which is difficult.

Unlike opening a pizza restaurant near a construction site. Once the building opens, workers won't have many preferences or standardized food-getting practices. Your pizza restaurant can become the incumbent quickly. You'll be the first restaurant in the area, so you'll gain a devoted following that makes your food a routine.

Great, right? It's easier than changing people's behavior. The benefit comes with a risk. Opening a pizza restaurant near a construction site increases future risk. What if builders run out of money? No one moves in? What if the building's occupants are the National Association of Pizza Haters? Then you've opened a pizza restaurant next to pizza haters.

Which kind of businessperson are you?

This isn't to say one type of entrepreneur is better than another. Each type of entrepreneurship requires different skills.

As my simple examples show, a problem-solving entrepreneur must operate in markets with established behaviors and habits. To be successful, you must be able to teach a market a new way of doing things.

Conversely, the challenge of being a visionary entrepreneur is that you have to be good at predicting the future and getting in front of that future before other people.

Both are difficult in different ways. So, smart entrepreneurs don't just chase opportunities. Smart entrepreneurs pursue opportunities that match their skill sets.

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.

Every week I meet many people interested in VC. Many of them ask me what it's like to be a junior analyst in VC or what I've learned so far.

Looking back, I've learned many things as a junior VC, having gone through an almost-euphoric peak bull market, failed tech IPOs of 2019 including WeWorks' catastrophic fall, and the beginnings of a bearish market.

1. Network, network, network!

VCs spend 80% of their time networking. Junior VCs source deals or manage portfolios. You spend your time bringing startups to your fund or helping existing portfolio companies grow. Knowing stakeholders (corporations, star talent, investors) in your particular areas of investment helps you develop your portfolio.

Networking was one of my strengths. When I first started in the industry, I'd go to startup events and meet 50 people a month. Over time, I realized these relationships were shallow and I was only getting business cards. So I stopped seeing networking as a transaction. VC is a long-term game, so you should work with people you like. Now I know who I click with and can build deeper relationships with them. My network is smaller but more valuable than before.

2. The Most Important Metric Is Founder

People often ask how we pick investments. Why some companies can raise money and others can't is a mystery. The founder is the most important metric for VCs. When a company is young, the product, environment, and team all change, but the founder remains constant. VCs bet on the founder, not the company.

How do we decide which founders are best after 2-3 calls? When looking at a founder's profile, ask why this person can solve this problem. The founders' track record will tell. If the founder is a serial entrepreneur, you know he/she possesses the entrepreneur DNA and will likely succeed again. If it's his/her first startup, focus on industry knowledge to deliver the best solution.

3. A company's fate can be determined by macrotrends.

Macro trends are crucial. A company can have the perfect product, founder, and team, but if it's solving the wrong problem, it won't succeed. I've also seen average companies ride the wave to success. When you're on the right side of a trend, there's so much demand that more companies can get a piece of the pie.

In COVID-19, macro trends made or broke a company. Ed-tech and health-tech companies gained unicorn status and raised funding at inflated valuations due to sudden demand. With the easing of pandemic restrictions and the start of a bear market, many of these companies' valuations are in question.

4. Look for methods to ACTUALLY add value.

You only need to go on VC twitter (read: @vcstartterkit and @vcbrags) for 5 minutes or look at fin-meme accounts on Instagram to see how much VCs claim to add value but how little they actually do. VC is a long-term game, though. Long-term, founders won't work with you if you don't add value.

How can we add value when we're young and have no network? Leaning on my strengths helped me. Instead of viewing my age and limited experience as a disadvantage, I realized that I brought a unique perspective to the table.

As a VC, you invest in companies that will be big in 5-7 years, and millennials and Gen Z will have the most purchasing power. Because you can relate to that market, you can offer insights that most Partners at 40 can't. I added value by helping with hiring because I had direct access to university talent pools and by finding university students for product beta testing.

5. Develop your personal brand.

Generalists or specialists run most funds. This means that funds either invest across industries or have a specific mandate. Most funds are becoming specialists, I've noticed. Top-tier founders don't lack capital, so funds must find other ways to attract them. Why would a founder work with a generalist fund when a specialist can offer better industry connections and partnership opportunities?

Same for fund members. Founders want quality investors. Become a thought leader in your industry to meet founders. Create content and share your thoughts on industry-related social media. When I first started building my brand, I found it helpful to interview industry veterans to create better content than I could on my own. Over time, my content attracted quality founders so I didn't have to look for them.

These are my biggest VC lessons. This list isn't exhaustive, but it's my industry survival guide.

“Perfectionism is the enemy of the idea muscle. " — James Altucher

Writer's block is a typical explanation for low output. Success requires productivity.

In four years of writing, I've never had writer's block. And you shouldn't care.

You'll never run out of content ideas if you follow a few tactics. No, I'm not overpromising.

Take Note of Ideas

Brains are strange machines. Blank when it's time to write. Idiot. Nothing. We get the best article ideas when we're away from our workstation.

• In the shower

• Driving

• In our dreams

• Walking

• During dull chats

• Meditating

• In the gym

No accident. The best ideas come in the shower, in nature, or while exercising.

(Your workstation is the worst place for creativity.)

The brain has time and space to link 'dots' of information during rest. It's eureka! New idea.

If you're serious about writing, capture thoughts as they come.

Immediately write down a new thought. Capture it. Don't miss it. Your future self will thank you.

As a writer, entrepreneur, or creative, letting ideas slide is bad.

I recommend using Evernote, Notion, or your device's basic note-taking tool to capture article ideas.

It doesn't matter whatever app you use as long as you collect article ideas.

When you practice 'idea-capturing' enough, you'll have an unending list of article ideas when writer's block hits.

High-Quality Content

More books, films, Medium pieces, and Youtube videos I consume, the more I'm inspired to write.

What you eat shapes who you are.

Celebrity gossip and fear-mongering news won't help your writing. It won't help you write regularly.

Instead, read expert-written books. Watch documentaries to improve your worldview. Follow amazing people online.

Develop your 'idea muscle' Daily creativity takes practice. The more you exercise your 'idea muscles,' the easier it is to generate article ideas.

I've trained my 'concept muscle' using James Altucher's exercise.

Write 10 ideas daily.

Write ten book ideas every day if you're an author. Write down 10 business ideas per day if you're an entrepreneur. Write down 10 investing ideas per day.

Write 10 article ideas per day. You become a content machine.

It doesn't state you need ten amazing ideas. You don't need 10 ideas. Ten ideas, regardless of quality.

Like at the gym, reps are what matter. With each article idea, you gain creativity. Writer's block is no match for this workout.

Quit Perfectionism

Perfectionism is bad for writers. You'll have bad articles. You'll have bad ideas. OK. It's creative.

Writing success requires prolificacy. You can't have 'perfect' articles.

“Perfectionism is the enemy of the idea muscle. Perfectionism is your brain trying to protect you from harm.” — James Altucher

Vincent van Gogh painted 900 pieces. The Starry Night is the most famous.

Thomas Edison invented 1093 things, but not all were as important as the lightbulb or the first movie camera.

Mozart composed nearly 600 compositions, but only Serenade No13 became popular.

Always do your best. Perfectionism shouldn't stop you from working. Write! Publicize. Make. Even if imperfect.

Write Your Story

Living an interesting life gives you plenty to write about. If you travel a lot, share your stories or lessons learned.

Describe your business's successes and shortcomings.

Share your experiences with difficulties or addictions.

More experiences equal more writing material.

If you stay indoors, perusing social media, you won't be inspired to write.

Have fun. Travel. Strive. Build a business. Be bold. Live a life worth writing about, and you won't run out of material.