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.

This is for young entrepreneurs, especially in tech.

People give useless success advice on TikTok and Reddit. Early risers, bookworms, etc. Entrepreneurship courses. Work hard and hustle.

False. These aren't successful traits.

I mean, organization is good. As someone who founded several businesses and now works at a VC firm, I find these tips to be clichés.

Based on founding four successful businesses and working with other successful firms, here's my best actionable advice:

1. Choose a sector or a niche and become an expert in it.

This is more generic than my next tip, but it's a must-do that's often overlooked. Become an expert in the industry or niche you want to enter. Discover everything.

Buy (future) competitors' products. Understand consumers' pain points. Market-test. Target keyword combos. Learn technical details.

The most successful businesses I've worked with were all formed by 9-5 employees. They knew the industry's pain points. They started a business targeting these pain points.

2. Choose a niche or industry crossroads to target.

How do you choose an industry or niche? What if your industry is too competitive?

List your skills and hobbies. Randomness is fine. Find an intersection between two interests or skills.

Say you build websites well. You like cars.

Web design is a *very* competitive industry. Cars and web design?

Instead of web design, target car dealers and mechanics. Build a few fake demo auto mechanic websites, then cold call shops with poor websites. Verticalize.

I've noticed a pattern:

• Person works in a particular industry for a corporation.

• Person gains expertise in the relevant industry.

• Person quits their job and launches a small business to address a problem that their former employer was unwilling to address.

I originally posted this on Reddit and it seemed to have taken off so I decided to share it with you all.

Focus on the product. When someone buys from you, you convince them the product's value exceeds the price. It's not fair and favors the buyer.

Creating a superior product or service will win. Narrowing this helps you outcompete others.

You may be their only (lucky) option.

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

Many of us have struggled for years to master a second language (in my case, English). Because (at least in my situation) we've always used an input-based system or method.

I'll explain in detail, but briefly: We can understand some conversations or sentences (since we've trained), but we can't give sophisticated answers or speak fluently (because we have NOT trained at all).

What exactly is input-based learning?

Reading, listening, writing, and speaking are key language abilities (if you look closely at that list, it seems that people tend to order them in this way: inadvertently giving more priority to the first ones than to the last ones).

These talents fall under two learning styles:

• Reading and listening are input-based activities (sometimes referred to as receptive skills or passive learning).

• Writing and speaking are output-based tasks (also known as the productive skills and/or active learning).

What's the best learning style? To learn a language, we must master four interconnected skills. The difficulty is how much time and effort we give each.

According to Shion Kabasawa's books The Power of Input: How to Maximize Learning and The Power of Output: How to Change Learning to Outcome (available only in Japanese), we spend 7:3 more time on Input Based skills than Output Based skills when we should be doing the opposite, leaning more towards Output (Input: Output->3:7).

I can't tell you how he got those numbers, but I think he's not far off because, for example, think of how many people say they're learning a second language and are satisfied bragging about it by only watching TV, series, or movies in VO (and/or reading a book or whatever) their Input is: 7:0 output!

You can't be good at a sport by watching TikTok videos about it; you must play.

“being pushed to produce language puts learners in a better position to notice the ‘gaps’ in their language knowledge”, encouraging them to ‘upgrade’ their existing interlanguage system. And, as they are pushed to produce language in real time and thereby forced to automate low-level operations by incorporating them into higher-level routines, it may also contribute to the development of fluency. — Scott Thornbury (P is for Push)

How may I practice output-based learning more?

I know that listening or reading is easy and convenient because we can do it on our own in a wide range of situations, even during another activity (although, as you know, it's not ideal), writing can be tedious/boring (it's funny that we almost always excuse ourselves in the lack of ideas), and speaking requires an interlocutor. But we must leave our comfort zone and modify our thinking to go from 3:7 to 7:3. (or at least balance it better to something closer). Gradually.

“You don’t have to do a lot every day, but you have to do something. Something. Every day.” — Callie Oettinger (Do this every day)

We can practice speaking like boxers shadow box.

Speaking out loud strengthens the mind-mouth link (otherwise, you will still speak fluently in your mind but you will choke when speaking out loud). This doesn't mean we should talk to ourselves on the way to work, while strolling, or on public transportation. We should try to do it without disturbing others, such as explaining what we've heard, read, or seen (the list is endless: you can TALK about what happened yesterday, your bedtime book, stories you heard at the office, that new kitten video you saw on Instagram, an experience you had, some new fact, that new boring episode you watched on Netflix, what you ate, what you're going to do next, your upcoming vacation, what’s trending, the news of the day)

Who will correct my grammar, vocabulary, or pronunciation with an imagined friend? We can't have everything, but tools and services can help [1].

Lack of bravery

Fear of speaking a language different than one's mother tongue in front of native speakers is global. It's easier said than done, because strangers, not your friends, will always make fun of your accent or faults. Accept it and try again. Karma will prevail.

Perfectionism is a trap. Stop self-sabotaging. Communication is key (and for that you have to practice the Output too ).

“Don’t forget to have fun and enjoy the process.” — Ruri Ohama

[1] Grammarly, Deepl, Google Translate, etc.