A fascinating business conversation.

This week at Web Summit, I had mentor hour.

Mentor hour connects startups with experienced entrepreneurs.

The YC-selected founder who mentored me had grown his company to $100 million in 18 months.

I had 45 minutes to question him.

I've compiled this.

Context

Founder's name is Zack.

After working in private equity, Zack opted to acquire an MBA.

Surrounded by entrepreneurs at a prominent school, he decided to become one himself.

Unsure how to proceed, he bet on two horses.

On one side, he received an offer from folks who needed help running their startup owing to lack of time. On the other hand, he had an idea for a SaaS to start himself.

He just needed to validate it.

Validating

Since Zack's proposal helped companies, he contacted university entrepreneurs for comments.

He contacted university founders.

Once he knew he'd correctly identified the problem and that people were willing to pay to address it, he started developing.

He earned $100k in a university entrepreneurship competition.

His plan was evident by then.

The other startup's founders saw his potential and granted him $400k to launch his own SaaS.

Hiring

He started looking for a tech co-founder because he lacked IT skills.

He interviewed dozens and picked the finest.

As he didn't want to wait for his program to be ready, he contacted hundreds of potential clients and got 15 letters of intent promising they'd join up when it was available.

YC accepted him by then.

He had enough positive signals to raise.

Raising

He didn't say how many VCs he called, but he indicated 50 were interested.

He jammed meetings into two weeks to generate pressure and encourage them to invest.

Seed raise: $11 million.

Selling

His objective was to contact as many entrepreneurs as possible to promote his product.

He first contacted startups by scraping CrunchBase data.

Once he had more money, he started targeting companies with ZoomInfo.

His VC urged him not to hire salespeople until he closed 50 clients himself.

He closed 100 and hired a CRO through a headhunter.

Scaling

Three persons started the business.

1. He primarily works in sales.

2. Coding the product was done by his co-founder.

3. Another person performing operational duties.

He regretted recruiting the third co-founder, who was ineffective (could have hired an employee instead).

He wanted his company to be big, so he hired two young marketing people from a competing company.

After validating several marketing channels, he chose PR.

$100 Million and under

He developed a sales team and now employs 30 individuals.

He raised a $100 million Series A.

Additionally, he stated

• He’s been rejected a lot. Like, a lot.

• Two great books to read: Steve Jobs by Isaacson, and Why Startups Fail by Tom Eisenmann.

• The best skill to learn for non-tech founders is “telling stories”, which means sales. A founder’s main job is to convince: co-founders, employees, investors, and customers. Learn code, or learn sales.

Conclusion

I often read about these stories but hardly take them seriously.

Zack was amazing.

Three things about him stand out:

1. His vision. He possessed a certain amount of fire.

2. His vitality. The man had a lot of enthusiasm and spoke quickly and decisively. He takes no chances and pushes the envelope in all he does.

3. His Rolex.

He didn't do all this in 18 months.

Not really.

He couldn't launch his company without private equity experience.

These accounts disregard entrepreneurs' original knowledge.

Hormozi will tell you how he founded Gym Launch, but he won't tell you how he had a gym first, how he worked at uni to pay for his gym, or how he went to the gym and learnt about fitness, which gave him the idea to open his own.

Nobody knows nothing. If you scale quickly, it's probable because you gained information early.

Lincoln said, "Give me six hours to chop down a tree, and I'll spend four sharpening the axe."

Sharper axes cut trees faster.

During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

Full article is available here

Learn these subtle cues to gain influence.

Hate being ignored?

As a 24-year-old, I struggled at work. Attention-getting tips How to avoid being judged by my size, gender, and lack of wrinkles or gray hair?

I've learned seniority hacks. Influence. Within two years as a product manager, I led a team. I'm a Stanford MBA student.

These communication hacks can make you look senior and influential.

1. Slowly speak

We speak quickly because we're afraid of being interrupted.

When I doubt my ideas, I speak quickly. How can we slow down? Jamie Chapman says speaking slowly saps our energy.

Chapman suggests emphasizing certain words and pausing.

2. Interrupted? Stop the stopper

Someone interrupt your speech?

Don't wait. "May I finish?" No pause needed. Stop interrupting. I first tried this in Leadership Laboratory at Stanford. How quickly I gained influence amazed me.

Next time, try “May I finish?” If that’s not enough, try these other tips from Wendy R.S. O’Connor.

3. Context

Others don't always see what's obvious to you.

Through explanation, you help others see the big picture. If a senior knows it, you help them see where your work fits.

4. Don't ask questions in statements

“Your statement lost its effect when you ended it on a high pitch,” a group member told me. Upspeak, it’s called. I do it when I feel uncertain.

Upspeak loses influence and credibility. Unneeded. When unsure, we can say "I think." We can even ask a proper question.

Someone else's boasting is no reason to be dismissive. As leaders and colleagues, we should listen to our colleagues even if they use this speech pattern.

Give your words impact.

5. Signpost structure

Signposts improve clarity by providing structure and transitions.

Communication coach Alexander Lyon explains how to use "first," "second," and "third" He explains classic and summary transitions to help the listener switch topics.

Signs clarify. Clarity matters.

6. Eliminate email fluff

“Fine. When will the report be ready? — Jeff.”

Notice how senior leaders write short, direct emails? I often use formalities like "dear," "hope you're well," and "kind regards"

Formality is (usually) unnecessary.

7. Replace exclamation marks with periods

See how junior an exclamation-filled email looks:

Hi, all!
Hope you’re as excited as I am for tomorrow! We’re celebrating our accomplishments with cake! Join us tomorrow at 2 pm!
See you soon!

Why the exclamation points? Why not just one?

Hi, all.
Hope you’re as excited as I am for tomorrow. We’re celebrating our accomplishments with cake. Join us tomorrow at 2 pm!
See you soon.

8. Take space

"Playing high" means having an open, relaxed body, says Stanford professor and author Deborah Gruenfield.

Crossed legs or looking small? Relax. Get bigger.

The Lex Fridman podcast host has interviewed Elon Musk.

Lex is a minimalist YouTuber. His videos are sloppy. Suits are his trademark.

In a video, he shares a typical day. I've smashed my 6-month goals using its ideas.

Here's his schedule.

Morning Mantra

Not woo-woo. Lex's mantra reflects his practicality.

Four parts.

Rulebook

"I remember the game's rules," he says.

Among them:

• Sleeping 6–8 hours nightly

• 1–3 times a day, he checks social media.

• Every day, despite pain, he exercises. "I exercise uninjured body parts."

Visualize

He imagines his day. "Like Sims..."

He says three things he's grateful for and contemplates death.

"Today may be my last"

Objectives

Then he visualizes his goals. He starts big. Five-year goals.

Short-term goals follow. Lex says they're year-end goals.

Near but out of reach.

Principles

He lists his principles. Assertions. His goals.

He acknowledges his cliche beliefs. Compassion, empathy, and strength are key.

Here's my mantra routine:

Four-Hour Deep Work

Lex begins a four-hour deep work session after his mantra routine. Today's toughest.

AI is Lex's specialty. His video doesn't explain what he does.

Clearly, he works hard.

Before starting, he has water, coffee, and a bathroom break.

"During deep work sessions, I minimize breaks."

He's distraction-free. Phoneless. Silence. Nothing. Any loose ideas are typed into a Google doc for later. He wants to work.

"Just get the job done. Don’t think about it too much and feel good once it’s complete." — Lex Fridman

30-Minute Social Media & Music

After his first deep work session, Lex rewards himself.

10 minutes on social media, 20 on music. Upload content and respond to comments in 10 minutes. 20 minutes for guitar or piano.

"In the real world, I’m currently single, but in the music world, I’m in an open relationship with this beautiful guitar. Open relationship because sometimes I cheat on her with the acoustic." — Lex Fridman

Two-hour exercise

Then exercise for two hours.

Daily runs six miles. Then he chooses how far to go. Run time is an hour.

He does bodyweight exercises. Every minute for 15 minutes, do five pull-ups and ten push-ups. It's David Goggins-inspired. He aims for an hour a day.

He's hungry. Before running, he takes a salt pill for electrolytes.

He'll then take a one-minute cold shower while listening to cheesy songs. Afterward, he might eat.

Four-Hour Deep Work

Lex's second work session.

He works 8 hours a day.

Again, zero distractions.

Eating

The video's meal doesn't look appetizing, but it's healthy.

It's ground beef with vegetables. Cauliflower is his "ground-floor" veggie. "Carrots are my go-to party food."

Lex's keto diet includes 1800–2000 calories.

He drinks a "nutrient-packed" Atheltic Greens shake and takes tablets. It's:

• One daily tablet of sodium.

• Magnesium glycinate tablets stopped his keto headaches.

• Potassium — "For electrolytes"

• Fish oil: healthy joints

“So much of nutrition science is barely a science… I like to listen to my own body and do a one-person, one-subject scientific experiment to feel good.” — Lex Fridman

Four-hour shallow session

This work isn't as mentally taxing.

Lex planned to:

• Finish last session's deep work (about an hour)

• Adobe Premiere podcasting (about two hours).

• Email-check (about an hour). Three times a day max. First, check for emergencies.

If he's sick, he may watch Netflix or YouTube documentaries or visit friends.

“The possibilities of chaos are wide open, so I can do whatever the hell I want.” — Lex Fridman

Two-hour evening reading

Nonstop work.

Lex ends the day reading academic papers for an hour. "Today I'm skimming two machine learning and neuroscience papers"

This helps him "think beyond the paper."

He reads for an hour.

“When I have a lot of energy, I just chill on the bed and read… When I’m feeling tired, I jump to the desk…” — Lex Fridman

Takeaways

Lex's day-in-the-life video is inspiring.

He has positive energy and works hard every day.

Schedule:

• Mantra Routine includes rules, visualizing, goals, and principles.

• Deep Work Session #1: Four hours of focus.

• 10 minutes social media, 20 minutes guitar or piano. "Music brings me joy"

• Six-mile run, then bodyweight workout. Two hours total.

• Deep Work #2: Four hours with no distractions. Google Docs stores random thoughts.

• Lex supplements his keto diet.

• This four-hour session is "open to chaos."

• Evening reading: academic papers followed by fiction.

"I value some things in life. Work is one. The other is loving others. With those two things, life is great." — Lex Fridman

Peter Thiel studied philosophy as an undergraduate.

Peter Thiel has $7.36 billion.

Peter is a world-ranked chess player, has a legal degree, and has written profitable novels.

In 1999, he co-founded PayPal with Max Levchin, which merged with X.com.

Peter Thiel made $55 million after selling the company to eBay for $1.5 billion in 2002.

You may be wondering…

How did Peter turn $55 million into his now multi-billion dollar net worth?

One amazing investment?

Facebook.

Thiel was Facebook's first external investor. He bought 10% of the company for $500,000 in 2004.

This investment returned 159% annually, 200x in 8 years.

By 2012, Thiel sold almost all his Facebook shares, becoming a billionaire.

What was the investment thesis of Peter?

This investment appeared ridiculous. Facebook was an innovative startup.

Thiel's $500,000 contribution transformed Facebook.

Harvard students have access to Facebook's 8 features and 1 photo per profile.

How did Peter determine that this would be a wise investment, then?

Facebook is a mimetic desire machine.

Social media's popularity is odd. Why peek at strangers' images on a computer?

Peter Thiel studied under French thinker Rene Girard at Stanford.

Mimetic Desire explains social media's success.

Mimetic Desire is the idea that humans desire things simply because other people do.

If nobody wanted it, would you?

Would you desire a family, a luxury car, or expensive clothes if no one else did? Girard says no.

People we admire affect our aspirations because we're social animals. Every person has a role model.

Our nonreligious culture implies role models are increasingly other humans, not God.

The idea explains why social media influencers are so powerful.

Why would Andrew Tate or Kim Kardashian matter if people weren't mimetic?

Humanity is fundamentally motivated by social comparison.

Facebook takes advantage of this need for social comparison, and puts it on a global scale.

It aggregates photographs and updates from millions of individuals.

Facebook mobile allows 24/7 social comparison.

Thiel studied mimetic desire with Girard and realized Facebook exploits the urge for social comparison to gain money.

Social media is more significant and influential than ever, despite Facebook's decline.

Thiel and Girard show that applied philosophy (particularly in business) can be immensely profitable.