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.

I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.

Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.

Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.

As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.

YC startups by status after 12 years:

Half the startups have failed, over one-third have exited, and the rest are still operating.

In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.

Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.

I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.

Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.

YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)

The world's most prestigious vintage vehicle show included amazing autos and record-breaking sums.

This 1932 Duesenberg J Figoni Sports Torpedo earned Best of Show in 2022.

David Paul Morris (DPM)/Bloomberg

2022 Pebble Beach Concours d'Elegance winner was a pre-war roadster.

Lee Anderson's 1932 Duesenberg J Figoni Sports Torpedo won Best of Show at Pebble Beach Golf Links near Carmel, Calif., on Sunday. First American win since 2013.

Sandra Button, chairperson of the annual concours, said the car, whose chassis and body had been separated for years, "marries American force with European style." "Its resurrection story is passionate."

Pebble Beach Concours d'Elegance Auction

Since 1950, the Pebble Beach Concours d'Elegance has welcomed the world's most costly collectable vehicles for a week of parties, auctions, rallies, and high-roller meetings. The cold, dreary weather highlighted the automobiles' stunning lines and hues.

DPM/Bloomberg

A visitor photographs a 1948 Ferrari 166 MM Touring Barchetta. This is one of 25 Ferraris manufactured in the years after World War II. First shown at the 1948 Turin Salon. Others finished Mille Miglia and Le Mans, which set the tone for Ferrari racing for years.

DPM/Bloomberg

This year's frontrunners were ultra-rare pre-war and post-war automobiles with long and difficult titles, such a 1937 Talbot-Lago T150C-SS Figoni & Falaschi Teardrop Coupe and a 1951 Talbot-Lago T26 Grand Sport Stabilimenti Farina Cabriolet.

The hefty, enormous coaches inspire visions of golden pasts when mysterious saloons swept over the road with otherworldly style, speed, and grace. Only the richest and most powerful people, like Indian maharaja and Hollywood stars, owned such vehicles.

Antonio Chopitea, a Peruvian sugar tycoon, ordered a new Duesenberg in Paris. Hemmings says the two-tone blue beauty was moved to the US and dismantled in the 1960s. Body and chassis were sold separately and rejoined decades later in a three-year, prize-winning restoration.

The concours is the highlight of Monterey Car Week, a five-day Super Bowl for car enthusiasts. Early events included Porsche and Ferrari displays, antique automobile races, and new-vehicle debuts. Many auto executives call Monterey Car Week the "new auto show."

Many visitors were drawn to the record-breaking auctions.

A 1969 Porsche 908/02 auctioned for $4.185 million. Flat-eight air-cooled engine, 90.6-inch wheelbase, 1,320-pound weight. Vic Elford, Richard Attwood, Rudi Lins, Gérard Larrousse, Kurt Ahrens Jr., Masten Gregory, and Pedro Rodriguez drove it, according to Gooding.

DPM/Bloomberg

The 1931 Bentley Eight Liter Sports Tourer doesn't meet its reserve. Gooding & Co., the official auction house of the concours, made more than $105 million and had an 82% sell-through rate. This powerful open-top tourer is one of W.O. Bentley's 100 automobiles. Only 80 remain.

DPM/Bloomberg

The final auction on Aug. 21 brought in $456.1 million, breaking the previous high of $394.48 million established in 2015 in Monterey. “The week put an exclamation point on what has been an exceptional year for the collector automobile market,” Hagerty analyst John Wiley said.

Many cars that go unsold at public auction are sold privately in the days after. After-sales pushed the week's haul to $469 million on Aug. 22, up 18.9% from 2015's record.

In today's currencies, 2015's record sales amount to $490 million, Wiley noted. The dollar is degrading faster than old autos.

Still, 113 million-dollar automobiles sold. The average car sale price was $583,211, up from $446,042 last year, while multimillion-dollar hammer prices made up around 75% of total sales.

Industry insiders and market gurus expected that stock market volatility, the crisis in Ukraine, and the dollar-euro exchange rate wouldn't influence the world's biggest spenders.

Classic.com's CEO said there's no hint of a recession in an e-mail. Big sales and crowds.

Ticket-holders wore huge hats, flowery skirts, and other Kentucky Derby-esque attire. Coffee, beverages, and food are extra.

DPM/Bloomberg

Mercedes-Benz 300 SL Gullwing, 1955. Mercedes produced the two-seat gullwing coupe from 1954–1957 and the roadster from 1957–1963. It was once West Germany's fastest and most powerful automobile. You'd be hard-pressed to locate one for less $1 million.

DPM/Bloomberg

1955 Ferrari 410 Sport sold for $22 million at RM Sotheby's. It sold a 1937 Mercedes-Benz 540K Sindelfingen Roadster for $9.9 million and a 1924 Hispano-Suiza H6C Transformable Torpedo for $9.245 million. The family-run mansion sold $221.7 million with a 90% sell-through rate, up from $147 million in 2021. This year, RM Sotheby's cars averaged $1.3 million.

Not everyone saw such great benefits.

Gooding & Co., the official auction house of the concours, made more than $105 million and had an 82% sell-through rate. 1937 Bugatti Type 57SC Atalante, 1990 Ferrari F40, and 1994 Bugatti EB110 Super Sport were top sellers.

The 1969 Autobianchi A112 Bertone. This idea two-seater became a Hot Wheels toy but was never produced. It has a four-speed manual drive and an inline-four mid-engine arrangement like the Lamborghini Miura.

DPM/Bloomberg

1956 Porsche 356 A Speedster at Gooding & Co. The Porsche 356 is a lightweight, rear-engine, rear-wheel drive vehicle that lacks driving power but is loved for its rounded, Beetle-like hardtop coupé and open-top versions.

DPM/Bloomberg

Mecum sold $50.8 million with a 64% sell-through rate, down from $53.8 million and 77% in 2021. Its top lot, a 1958 Ferrari 250 GT 'Tour de France' Alloy Coupe, sold for $2.86 million, but its average price was $174,016.

Bonhams had $27.8 million in sales with an 88% sell-through rate. The same sell-through generated $35.9 million in 2021.

Gooding & Co. and RM Sotheby's posted all 10 top sales, leaving Bonhams, Mecum, and Hagerty-owned Broad Arrow fighting for leftovers. Six of the top 10 sellers were Ferraris, which remain the gold standard for collectable automobiles. Their prices have grown over decades.

Classic.com's Calle claimed RM Sotheby's "stole the show," but "BroadArrow will be a force to reckon with."

Although pre-war cars were hot, '80s and '90s cars showed the most appreciation and attention. Generational transition and new buyer profile."

2022 Pebble Beach Concours d'Elegance judges inspect 1953 Siata 208. The rounded coupe was introduced at the 1952 Turin Auto Show in Italy and is one of 18 ever produced. It sports a 120hp Fiat engine, five-speed manual transmission, and alloy drum brakes. Owners liked their style, but not their reliability.

DPM/Bloomberg

The Czinger 21 CV Max at Pebble Beach. Monterey Car Week concentrates on historic and classic automobiles, but modern versions like this Czinger hypercar also showed.

DPM/Bloomberg

The 1932 Duesenberg J Figoni Sports Torpedo won Best in Show in 2022. Lee and Penny Anderson of Naples, Fla., own the once-separate-chassis-from-body automobile.

DPM/Bloomberg

The Habit of Learning implies constantly learning something new. One daily habit will make you successful. Learning will help you succeed.

Most successful people continually learn. Success requires this behavior. Daily learning.

Success loves books. Books offer expert advice. Everything is online today. Most books are online, so you can skip the library. You must download it and study for 15-30 minutes daily. This habit changes your thinking.

Typical Successful People

• Warren Buffett reads 500 pages of corporate reports and five newspapers for five to six hours each day.

• Each year, Bill Gates reads 50 books.

• Every two weeks, Mark Zuckerberg reads at least one book.

• According to his brother, Elon Musk studied two books a day as a child and taught himself engineering and rocket design.

Learning & Making Money Online

No worries if you can't afford books. Everything is online. YouTube, free online courses, etc.

How can you create this behavior in yourself?

1) Consider what you want to know

Before learning, know what's most important. So, move together.

Set a goal and schedule learning.

After deciding what you want to study, create a goal and plan learning time.

3) GATHER RESOURCES

Get the most out of your learning resources. Online or offline.

I read 53 novels last year and hope to do so again.

Books are best if you love learning. You get a range of perspectives, unlike podcasts and YouTube channels where you get the same ones.

Book quality varies. I've read useless books. Most books teach me something.

These 9 novels have changed my outlook in recent years. They've made me rethink what I believed or introduced me to a fresh perspective that changed my worldview.

You can order these books yourself. Or, read my summaries to learn what I've synthesized.

Enjoy!

Fooled By Randomness

Nassim Taleb worked as a Wall Street analyst. He used options trading to bet on unlikely events like stock market crashes.

Using financial models, investors predict stock prices. The models assume constant, predictable company growth.

These models base their assumptions on historical data, so they assume the future will be like the past.

Fooled By Randomness argues that the future won't be like the past. We often see impossible market crashes like 2008's housing market collapse. The world changes too quickly to use historical data: by the time we understand how it works, it's changed.

Most people don't live to see history unfold. We think our childhood world will last forever. That goes double for stable societies like the U.S., which hasn't seen major turbulence in anyone's lifetime.

Fooled By Randomness taught me to expect the unexpected. The world is deceptive and rarely works as we expect. You can't always trust your past successes or what you've learned.

Antifragile

More Taleb. Some things, like the restaurant industry and the human body, improve under conditions of volatility and turbulence.

We didn't have a word for this counterintuitive concept until Taleb wrote Antifragile. The human body (which responds to some stressors, like exercise, by getting stronger) and the restaurant industry both benefit long-term from disorder (when economic turbulence happens, bad restaurants go out of business, improving the industry as a whole).

Many human systems are designed to minimize short-term variance because humans don't understand it. By eliminating short-term variation, we increase the likelihood of a major disaster.

Once, we put out every forest fire we found. Then, dead wood piled up in forests, causing catastrophic fires.

We don't like price changes, so politicians prop up markets with stimulus packages and printing money. This leads to a bigger crash later. Two years ago, we printed a ton of money for stimulus checks, and now we have double-digit inflation.

Antifragile taught me how important Plan B is. A system with one or two major weaknesses will fail. Make large systems redundant, foolproof, and change-responsive.

Reality is broken

We dread work. Work is tedious. Right?

Wrong. Work gives many people purpose. People are happiest when working. (That's why some are workaholics.)

Factory work saps your soul, office work is boring, and working for a large company you don't believe in and that operates unethically isn't satisfying.

Jane McGonigal says in Reality Is Broken that meaningful work makes us happy. People love games because they simulate good work. McGonigal says work should be more fun.

Some think they'd be happy on a private island sipping cocktails all day. That's not true. Without anything to do, most people would be bored. Unemployed people are miserable. Many retirees die within 2 years, much more than expected.

Instead of complaining, find meaningful work. If you don't like your job, it's because you're in the wrong environment. Find the right setting.

The Lean Startup

Before the airplane was invented, Harvard scientists researched flying machines. Who knew two North Carolina weirdos would beat them?

The Wright Brothers' plane design was key. Harvard researchers were mostly theoretical, designing an airplane on paper and trying to make it fly in theory. They'd build it, test it, and it wouldn't fly.

The Wright Brothers were different. They'd build a cheap plane, test it, and it'd crash. Then they'd learn from their mistakes, build another plane, and it'd crash.

They repeated this until they fixed all the problems and one of their planes stayed aloft.

Mistakes are considered bad. On the African savannah, one mistake meant death. Even today, if you make a costly mistake at work, you'll be fired as a scapegoat. Most people avoid failing.

In reality, making mistakes is the best way to learn.

Eric Reis offers an unintuitive recipe in The Lean Startup: come up with a hypothesis, test it, and fail. Then, try again with a new hypothesis. Keep trying, learning from each failure.

This is a great startup strategy. Startups are new businesses. Startups face uncertainty. Run lots of low-cost experiments to fail, learn, and succeed.

Don't fear failing. Low-cost failure is good because you learn more from it than you lose. As long as your worst-case scenario is acceptable, risk-taking is good.

The Sovereign Individual

Today, nation-states rule the world. The UN recognizes 195 countries, and they claim almost all land outside of Antarctica.

We agree. For the past 2,000 years, much of the world's territory was ungoverned.

Why today? Because technology has created incentives for nation-states for most of the past 500 years. The logic of violence favors nation-states, according to James Dale Davidson, author of the Sovereign Individual. Governments have a lot to gain by conquering as much territory as possible, so they do.

Not always. During the Dark Ages, Europe was fragmented and had few central governments. Partly because of armor. With armor, a sword, and a horse, you couldn't be stopped. Large states were hard to form because they rely on the threat of violence.

When gunpowder became popular in Europe, violence changed. In a world with guns, assembling large armies and conquest are cheaper.

James Dale Davidson says the internet will make nation-states obsolete. Most of the world's wealth will be online and in people's heads, making capital mobile.

Nation-states rely on predatory taxation of the rich to fund large militaries and welfare programs.

When capital is mobile, people can live anywhere in the world, Davidson says, making predatory taxation impossible. They're not bound by their job, land, or factory location. Wherever they're treated best.

Davidson says that over the next century, nation-states will collapse because they won't have enough money to operate as they do now. He imagines a world of small city-states, like Italy before 1900. (or Singapore today).

We've already seen some movement toward a more Sovereign Individual-like world. The pandemic proved large-scale remote work is possible, freeing workers from their location. Many cities and countries offer remote workers incentives to relocate.

Many Western businesspeople live in tax havens, and more people are renouncing their US citizenship due to high taxes. Increasing globalization has led to poor economic conditions and resentment among average people in the West, which is why politicians like Trump and Sanders rose to popularity with angry rhetoric, even though Obama rose to popularity with a more hopeful message.

The Sovereign Individual convinced me that the future will be different than Nassim Taleb's. Large countries like the U.S. will likely lose influence in the coming decades, while Portugal, Singapore, and Turkey will rise. If the trend toward less freedom continues, people may flee the West en masse.

So a traditional life of college, a big firm job, hard work, and corporate advancement may not be wise. Young people should learn as much as possible and develop flexible skills to adapt to the future.

Sapiens

Sapiens is a history of humanity, from proto-humans in Ethiopia to our internet society today, with some future speculation.

Sapiens views humans (and Homo sapiens) as a unique species on Earth. We were animals 100,000 years ago. We're slowly becoming gods, able to affect the climate, travel to every corner of the Earth (and the Moon), build weapons that can kill us all, and wipe out thousands of species.

Sapiens examines what makes Homo sapiens unique. Humans can believe in myths like religion, money, and human-made entities like countries and LLCs.

These myths facilitate large-scale cooperation. Ants from the same colony can cooperate. Any two humans can trade, though. Even if they're not genetically related, large groups can bond over religion and nationality.

Combine that with intelligence, and you have a species capable of amazing feats.

Sapiens may make your head explode because it looks at the world without presupposing values, unlike most books. It questions things that aren't usually questioned and says provocative things.

It also shows how human history works. It may help you understand and predict the world. Maybe.

The 4-hour Workweek

Things can be done better.

Tradition, laziness, bad bosses, or incentive structures cause complacency. If you're willing to make changes and not settle for the status quo, you can do whatever you do better and achieve more in less time.

The Four-Hour Work Week advocates this. Tim Ferriss explains how he made more sales in 2 hours than his 8-hour-a-day colleagues.

By firing 2 of his most annoying customers and empowering his customer service reps to make more decisions, he was able to leave his business and travel to Europe.

Ferriss shows how to escape your 9-to-5, outsource your life, develop a business that feeds you with little time, and go on mini-retirement adventures abroad.

Don't accept the status quo. Instead, level up. Find a way to improve your results. And try new things.

Why Nations Fail

Nogales, Arizona and Mexico were once one town. The US/Mexico border was arbitrarily drawn.

Both towns have similar cultures and populations. Nogales, Arizona is well-developed and has a high standard of living. Nogales, Mexico is underdeveloped and has a low standard of living. Whoa!

Why Nations Fail explains how government-created institutions affect country development. Strong property rights, capitalism, and non-corrupt governments promote development. Countries without capitalism, strong property rights, or corrupt governments don't develop.

Successful countries must also embrace creative destruction. They must offer ordinary citizens a way to improve their lot by creating value for others, not reducing them to slaves, serfs, or peasants. Authors say that ordinary people could get rich on trading expeditions in 11th-century Venice.

East and West Germany and North and South Korea have different economies because their citizens are motivated differently. It explains why Chile, China, and Singapore grow so quickly after becoming market economies.

People have spent a lot of money on third-world poverty. According to Why Nations Fail, education and infrastructure aren't the answer. Developing nations must adopt free-market economic policies.

Elon Musk

Elon Musk is the world's richest man, but that’s not a good way to describe him. Elon Musk is the world's richest man, which is like calling Steve Jobs a turtleneck-wearer or Benjamin Franklin a printer.

Elon Musk does cool sci-fi stuff to help humanity avoid existential threats.

Oil will run out. We've delayed this by developing better extraction methods. We only have so much nonrenewable oil.

Our society is doomed if it depends on oil. Elon Musk invested heavily in Tesla and SolarCity to speed the shift to renewable energy.

Musk worries about AI: we'll build machines smarter than us. We won't be able to stop these machines if something goes wrong, just like cows can't fight humans. Neuralink: we need to be smarter to compete with AI when the time comes.

If Earth becomes uninhabitable, we need a backup plan. Asteroid or nuclear war could strike Earth at any moment. We may not have much time to react if it happens in a few days. We must build a new civilization while times are good and resources are plentiful.

Short-term problems dominate our politics, but long-term issues are more important. Long-term problems can cause mass casualties and homelessness. Musk demonstrates how to think long-term.

The main reason people are impressed by Elon Musk, and why Ashlee Vances' biography influenced me so much, is that he does impossible things.

Electric cars were once considered unprofitable, but Tesla has made them mainstream. SpaceX is the world's largest private space company.

People lack imagination and dismiss ununderstood ideas as impossible. Humanity is about pushing limits. Don't worry if your dreams seem impossible. Try it.

Thanks for reading.