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 ;)

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

Ray Dalio's super-effective roadmap 

Ray Dalio's $22 billion net worth ranks him 36th globally. From 1975 to 2011, he built the world's most successful hedge fund, never losing more than 4% from 1991 to 2020. (and only doing so during 3 calendar years). 

Dalio describes a 5-step process in his best-selling book Principles. It's the playbook he's used to build his hedge fund, beat the markets, and face personal challenges. 

This 5-step system is so valuable and well-explained that I didn't edit or change anything; I only added my own insights in the parts I found most relevant and/or relatable as a young entrepreneur. The system's overview: 

1. Have clear goals 

2. Identify and don’t tolerate problems 

3. Diagnose problems to get at their root causes 

4. Design plans that will get you around those problems 

5. Do what is necessary to push through the plans to get results 

If you follow these 5 steps in a virtuous loop, you'll almost always see results. Repeat the process for each goal you have. 

1. Have clear goals 

a) Prioritize: You can have almost anything, but not everything. 

I started and never launched dozens of projects for 10 years because I was scattered. I opened a t-shirt store, traded algorithms, sold art on Instagram, painted skateboards, and tinkered with electronics. I decided to try blogging for 6 months to see where it took me. Still going after 3 years. 

b) Don’t confuse goals with desires. 

A goal inspires you to act. Unreasonable desires prevent you from achieving your goals. 

c) Reconcile your goals and desires to decide what you want. 

d) Don't confuse success with its trappings. 

e) Never dismiss a goal as unattainable. 

Always one path is best. Your perception of what's possible depends on what you know now. I never thought I'd make money writing online so quickly, and now I see a whole new horizon of business opportunities I didn't know about before. 

f) Expectations create abilities. 

Don't limit your abilities. More you strive, the more you'll achieve. 

g) Flexibility and self-accountability can almost guarantee success. 

Flexible people accept what reality or others teach them. Self-accountability is the ability to recognize your mistakes and be more creative, flexible, and determined. 

h) Handling setbacks well is as important as moving forward. 

Learn when to minimize losses and when to let go and move on. 

2. Don't ignore problems 

a) See painful problems as improvement opportunities. 

Every problem, painful situation, and challenge is an opportunity. Read The Art of Happiness for more. 

b) Don't avoid problems because of harsh realities. 

Recognizing your weaknesses isn't the same as giving in. It's the first step in overcoming them. 

c) Specify your issues. 

There is no "one-size-fits-all" solution. 

d) Don’t mistake a cause of a problem with the real problem. 

"I can't sleep" is a cause, not a problem. "I'm underperforming" could be a problem. 

e) Separate big from small problems. 

You have limited time and energy, so focus on the biggest problems. 

f) Don't ignore a problem. 

Identifying a problem and tolerating it is like not identifying it. 

3. Identify problems' root causes 

a) Decide "what to do" after assessing "what is." 

"A good diagnosis takes 15 to 60 minutes, depending on its accuracy and complexity. [...] Like principles, root causes recur in different situations. 

b) Separate proximate and root causes. 

"You can only solve problems by removing their root causes, and to do that, you must distinguish symptoms from disease." 

c) Knowing someone's (or your own) personality can help you predict their behavior. 

4. Design plans that will get you around the problems 

a) Retrace your steps. 

Analyze your past to determine your future. 

b) Consider your problem a machine's output. 

Consider how to improve your machine. It's a game then. 

c) There are many ways to reach your goals. 

Find a solution. 

d) Visualize who will do what in your plan like a movie script. 

Consider your movie's actors and script's turning points, then act accordingly. The game continues. 

e) Document your plan so others can judge your progress. 

Accountability boosts success. 

f) Know that a good plan doesn't take much time. 

The execution is usually the hardest part, but most people either don't have a plan or keep changing it. Don't drive while building the car. Build it first, because it'll be bumpy. 

5. Do what is necessary to push through the plans to get results 

a) Great planners without execution fail. 

Life is won with more than just planning. Similarly, practice without talent beats talent without practice. 

b) Work ethic is undervalued. 

Hyper-productivity is praised in corporate America, even if it leads nowhere. To get things done, use checklists, fewer emails, and more desk time. 

c) Set clear metrics to ensure plan adherence. 

I've written about the OKR strategy for organizations with multiple people here. If you're on your own, I recommend the Wheel of Life approach. Both systems start with goals and tasks to achieve them. Then start executing on a realistic timeline. 

If you find solutions, weaknesses don't matter. 

Everyone's weak. You, me, Gates, Dalio, even Musk. Nobody will be great at all 5 steps of the system because no one can think in all the ways required. Some are good at analyzing and diagnosing but bad at executing. Some are good planners but poor communicators. Others lack self-discipline. 

Stay humble and ask for help when needed. Nobody has ever succeeded 100% on their own, without anyone else's help. That's the paradox of individual success: teamwork is the only way to get there. 

Most people won't have the skills to execute even the best plan. You can get missing skills in two ways: 

1. Self-taught (time-consuming) 

2. Others' (requires humility) light

On knowing what to do with your life 

“Some people have good mental maps and know what to do on their own. Maybe they learned them or were blessed with common sense. They have more answers than others. Others are more humble and open-minded. […] Open-mindedness and mental maps are most powerful.” — Ray Dalio 

I've always known what I wanted to do, so I'm lucky. I'm almost 30 and have always had trouble executing. Good thing I never stopped experimenting, but I never committed to anything long-term. I jumped between projects. I decided 3 years ago to stick to one project for at least 6 months and haven't looked back. 

Maybe you're good at staying focused and executing, but you don't know what to do. Maybe you have none of these because you haven't found your purpose. Always try new projects and talk to as many people as possible. It will give you inspiration and ideas and set you up for success. 

There is almost always a way to achieve a crazy goal or idea. 

Enjoy the journey, whichever path you take.

Crypto and blockchain have rebranded as web3. They probably thought it sounded better and didn't want the baggage of scam ICOs, STOs, and skirted securities laws.

It was like Facebook becoming Meta. Crypto's biggest players wanted to change public (and regulator) perception away from pump-and-dump schemes.

After the 2018 ICO gold rush, it's understandable. Every project that raised millions (or billions) never shipped a meaningful product.

Like many crazes, charlatans took the money and ran.

Despite its grifter past, web3 is THE hot topic today as more founders, venture firms, and larger institutions look to build the future decentralized internet.

Supposedly.

How often have you heard: This will change the world, fix the internet, and give people power?

Why are most of web3's biggest proponents (and beneficiaries) the same rich, powerful players who built and invested in the modern internet? It's like they want to remake and own the internet.

Something seems off about that.

Why are insiders getting preferential presale terms before the public, allowing early investors and proponents to flip dirt cheap tokens and advisors shares almost immediately after the public sale?

It's a good gig with guaranteed markups, no risk or progress.

If it sounds like insider trading, it is, at least practically. This is clear when people talk about blockchain/web3 launches and tokens.

Fast money, quick flips, and guaranteed markups/returns are common.

Incentives-wise, it's hard to blame them. Who can blame someone for following the rules to win? Is it their fault or regulators' for not leveling the playing field?

It's similar to oil companies polluting for profit, Instagram depressing you into buying a new dress, or pharma pushing an unnecessary pill.

All of that is fair game, at least until we change the playbook, because people (and corporations) change for pain or love. Who doesn't love money?

belief based on money gain

Sinclair:

“It is difficult to get a man to understand something when his salary depends upon his not understanding it.”

Bitcoin, blockchain, and web3 analogies?

Most blockchain and web3 proponents are true believers, not cynical capitalists. They believe blockchain's inherent transparency and permissionless trust allow humanity to evolve beyond our reptilian ways and build a better decentralized and democratic world.

They highlight issues with the modern internet and monopoly players like Google, Facebook, and Apple. Decentralization fixes everything

If we could give power back to the people and get governments/corporations/individuals out of the way, we'd fix everything.

Blockchain solves supply chain and child labor issues in China.

To meet Paris climate goals, reduce emissions. Create a carbon token.

Fixing online hatred and polarization Web3 Twitter and Facebook replacement.

Web3 must just be the answer for everything… your “perfect” silver bullet.

Nothing fits everyone. Blockchain has pros and cons like everything else.

Blockchain's viral, ponzi-like nature has an MLM (mid level marketing) feel. If you bought Taylor Swift's NFT, your investment is tied to her popularity.

Probably makes you promote Swift more. Play music loudly.

Here's another example:

Imagine if Jehovah’s Witnesses (or evangelical preachers…) got paid for every single person they converted to their cause.

It becomes a self-fulfilling prophecy as their faith and wealth grow.

Which breeds extremism? Ultra-Orthodox Jews are an example. maximalists

Bitcoin and blockchain are causes, religions. It's a money-making movement and ideal.

We're good at convincing ourselves of things we want to believe, hence filter bubbles.

I ignore anything that doesn't fit my worldview and seek out like-minded people, which algorithms amplify.

Then what?

Is web3 merely a new scam?

No, never!

Blockchain has many crucial uses.

Sending money home/abroad without bank fees;

Like fleeing a war-torn country and converting savings to Bitcoin;

Like preventing Twitter from silencing dissidents.

Permissionless, trustless databases could benefit society and humanity. There are, however, many limitations.

Lost password?

What if you're cheated?

What if Trump/Putin/your favorite dictator incites a coup d'état?

What-ifs abound. Decentralization's openness brings good and bad.

No gatekeepers or firefighters to rescue you.

ISIS's fundraising is also frictionless.

Community-owned apps with bad interfaces and service.

Trade-offs rule.

So what compromises does web3 make?

What are your trade-offs? Decentralization has many strengths and flaws. Like Bitcoin's wasteful proof-of-work or Ethereum's political/wealth-based proof-of-stake.

To ensure the survival and veracity of the network/blockchain and to safeguard its nodes, extreme measures have been designed/put in place to prevent hostile takeovers aimed at altering the blockchain, i.e., adding money to your own wallet (account), etc.

These protective measures require significant resources and pose challenges. Reduced speed and throughput, high gas fees (cost to submit/write a transaction to the blockchain), and delayed development times, not to mention forked blockchain chains oops, web3 projects.

Protecting dissidents or rogue regimes makes sense. You need safety, privacy, and calm.

First-world life?

What if you assumed EVERYONE you saw was out to rob/attack you? You'd never travel, trust anyone, accomplish much, or live fully. The economy would collapse.

It's like an ant colony where half the ants do nothing but wait to be attacked.

Waste of time and money.

11% of the US budget goes to the military. Imagine what we could do with the $766B+ we spend on what-ifs annually.

Is so much hypothetical security needed?

Blockchain and web3 are similar.

Does your app need permissionless decentralization? Does your scooter-sharing company really need a proof-of-stake system and 1000s of nodes to avoid Russian hackers? Why?

Worst-case scenario? It's not life or death, unless you overstate the what-ifs. Web3 proponents find improbable scenarios to justify decentralization and tokenization.

Do I need a token to prove ownership of my painting? Unless I'm a master thief, I probably bought it.

despite losing the receipt.

I do, however, love Web 3.

Enough Web3 bashing for now. Understand? Decentralization isn't perfect, but it has huge potential when applied to the right problems.

I see many of the right problems as disrupting big tech's ruthless monopolies. I wrote several years ago about how tokenized blockchains could be used to break big tech's stranglehold on platforms, marketplaces, and social media.

Tokenomics schemes can be used for good and are powerful. Here’s how.

Before the ICO boom, I made a series of predictions about blockchain/crypto's future. It's still true.

Here's where I was then and where I see web3 going:

My 11 Big & Bold Predictions for Blockchain

In the near future, people may wear crypto cash rings or bracelets.

1. While some governments repress cryptocurrency, others will start to embrace it.

2. Blockchain will fundamentally alter voting and governance, resulting in a more open election process.

3. Money freedom will lead to a more geographically open world where people will be more able to leave when there is unrest.

4. Blockchain will make record keeping significantly easier, eliminating the need for a significant portion of government workers whose sole responsibility is paperwork.

5. Overrated are smart contracts.

6. Tokens will replace company stocks.

7. Blockchain increases real estate's liquidity, value, and volatility.

8. Healthcare may be most affected.

9. Crypto could end privacy and lead to Minority Report.

10. New companies with network effects will displace incumbents.

11. Soon, people will wear rings or bracelets with crypto cash.

Some have already happened, while others are still possible.

Time will tell if they happen.

And finally:

What will web3 be?

Who will be in charge?

Closing remarks

Hope you enjoyed this web3 dive. There's much more to say, but that's for another day.

We're writing history as we go.

Tech regulation, mergers, Bitcoin surge How will history remember us?

What about web3 and blockchain?

Is this a revolution or a tulip craze?

Remember, actions speak louder than words (share them in the comments).

Your turn.

Homeownership isn't the only life pattern.

Want to irritate people?

My party trick is to say I used to own a house but no longer do.

I no longer wish to own a home, not because I lost it or because I'm moving.

It was a long-term plan. It was more deliberate than buying a home. Many people are committed for this reason.

Poppycock.

Anyone who told me that owning a house (or striving to do so) is a must is wrong.

Because, URGH.

One pattern for life is to own a home, but there are millions of others.

You can afford to buy a home? Go, buddy.

You think you need 1,000 square feet (or more)? You think it's non-negotiable in life?

Nope.

It's insane that society forces everyone to own real estate, regardless of income, wants, requirements, or situation. As if this trade brings happiness, stability, and contentment.

Take it from someone who thought this for years: drywall isn't happy. Living your way brings contentment.

That's in real estate. It may also be renting a small apartment in a city that makes your soul sing, but you can't afford the downpayment or mortgage payments.

Living or traveling abroad is difficult when your life savings are connected to something that eats your money the moment you sign.

#vanlife, which seems like torment to me, makes some people feel alive.

I've seen co-living, vacation rental after holiday rental, living with family, and more work.

Insisting that home ownership is the only path in life is foolish and reduces alternative options.

How little we question homeownership is a disgrace.

No one challenges a homebuyer's motives. We congratulate them, then that's it.

When you offload one, you must answer every question, even if you have a loose screw.

• Why do you want to sell?

• Do you have any concerns about leaving the market?

• Why would you want to renounce what everyone strives for?

• Why would you want to abandon a beautiful place like that?

• Why would you mismanage your cash in such a way?

• But surely it's only temporary? RIGHT??

Incorrect questions. Buying a property requires several inquiries.

• The typical American has $4500 saved up. When something goes wrong with the house (not if, it’s never if), can you actually afford the repairs?

• Are you certain that you can examine a home in less than 15 minutes before committing to buying it outright and promising to pay more than twice the asking price on a 30-year 7% mortgage?

• Are you certain you're ready to leave behind friends, family, and the services you depend on in order to acquire something?

• Have you thought about the connotation that moving to a suburb, which more than half of Americans do, means you will be dependent on a car for the rest of your life?

Plus:

Are you sure you want to prioritize home ownership over debt, employment, travel, raising kids, and daily routines?

Homeownership entails that. This ex-homeowner says it will rule your life from the time you put the key in the door.

This isn't questioned. We don't question enough. The holy home-ownership grail was set long ago, and we don't challenge it.

Many people question after signing the deeds. 70% of homeowners had at least one regret about buying a property, including the expense.

Exactly. Tragic.

Homes are different from houses

We've been fooled into thinking home ownership will make us happy.

Some may agree. No one.

Bricks and brick hindered me from living the version of my life that made me most comfortable, happy, and steady.

I'm spending the next month in a modest apartment in southern Spain. Even though it's late November, today will be 68 degrees. My spouse and I will soon meet his visiting parents. We'll visit a Sherry store. We'll eat, nap, walk, and drink Sherry. Writing. Jerez means flamenco.

That's my home. This is such a privilege. Living a fulfilling life brings me the contentment that buying a home never did.

I'm happy and comfortable knowing I can make almost all of my days good. Rejecting home ownership is partly to blame.

I'm broke like most folks. I had to choose between home ownership and comfort. I said, I didn't find them together.

Feeling at home trumps owning brick-and-mortar every day.

The following is the reality of what it's like to turn the American Dream around.

Leaving the housing market.

Sometimes I wish I owned a home.

I miss having my own yard and bed. My kitchen, cookbooks, and pizza oven are missed.

But I rarely do.

Someone else's life plan pushed home ownership on me. I'm grateful I figured it out at 35. Many take much longer, and some never understand homeownership stinks (for them).

It's confusing. People will think you're dumb or suicidal.

If you read what I write, you'll know. You'll realize that all you've done is choose to live intentionally. Find a home beyond four walls and a picket fence.

Miss? As I said, they're not home. If it were, a pizza oven, a good mattress, and a well-stocked kitchen would bring happiness.

No.

If you can afford a house and desire one, more power to you.

There are other ways to discover home. Find calm and happiness. For fun.

For it, look deeper than your home's foundation.