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.

How did his money blind me?

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

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

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

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

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

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

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

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

Putting your faith in results over relevance

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

Ultimately, I followed the advice of the billionaire.

Obviously.

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

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

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

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

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

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

Success vs. relevance

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

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

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

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

My ego is so huge it won't fit through the door.

I don't know how I feel about it. I should be excited. Many of you have this exact dream to publish a book with a well-known book publisher and get a juicy advance.

Let me dissect how I'm thinking about it to help you.

How it happened

An email comes in. A generic "can we put a backlink on your website and get a freebie" email.

Almost deleted it.

Then I noticed the logo. It seemed shady. I found the URL. Check. I searched the employee's LinkedIn. Legit. I avoided middlemen. Check.

Mixed feelings. LinkedIn hasn't valued my writing for years. I'm just a guy in an unironed t-shirt whose content they sell advertising against.

They get big dollars. I get $0 and a few likes, plus some email subscribers.

Still, I felt adrenaline for hours.

I texted a few friends to see how they felt. I wrapped them.

Messages like "No shocker. You're entertaining online." I didn't like praises, so I blushed.

The thrill faded after hours. Who knows?

Most authors desire this chance.

"You entitled piece of crap, Denning!"

You may think so. Okay. My job is to stand on the internet and get bananas thrown at me.

I approached writing backwards. More important than a book deal was a social media audience converted to an email list.

Romantic authors think backward. They hope a fantastic book will land them a deal and an audience.

Rarely occurs. So I never pursued it. It's like permission-seeking or the lottery.

Not being a professional writer, I've never written a good book. I post online for fun and to express my opinions.

Writing is therapeutic. I overcome mental illness and rebuilt my life this way. Without blogging, I'd be dead.

I've always dreamed of staying alive and doing something I love, not getting a book contract. Writing is my passion. I'm a winner without a book deal.

Why I was given a book deal

You may assume I received a book contract because of my views or follows. Nope.

They gave me a deal because they like my writing style. I've heard this for eight years.

Several authors agree. One asked me to improve their writer's voice.

Takeaway: highlight your writer's voice.

What if they discover I'm writing incompetently?

An edited book is published. It's edited.

I need to master writing mechanics, thus this concerns me. I need help with commas and sentence construction.

I must learn verb, noun, and adjective. Seriously.

Writing a book may reveal my imposter status to a famous publisher. Imagine the email

"It happened again. He doesn't even know how to spell. He thinks 'less' is the correct word, not 'fewer.' Are you sure we should publish his book?"

Fears stink.

I'm capable of blogging. Even listicles. So what?

Writing for a major publisher feels advanced.

I only blog. I'm good at listicles. Digital media executives have criticized me for this.

• It is allegedly clickbait.

• Or it is following trends.

• Alternately, growth hacking.

Never. I learned copywriting to improve my writing.

Apple, Amazon, and Tesla utilize copywriting to woo customers. Whoever thinks otherwise is the wisest person in the room.

Old-schoolers loathe copywriters.

Their novels sell nothing.

They assume their elitist version of writing is better and that the TikTok generation will invest time in random writing with no subheadings and massive walls of text they can't read on their phones.

I'm terrified of book proposals.

My friend's book proposal suggestion was contradictory and made no sense.

They told him to compose another genre. This book got three Amazon reviews. Is that a good model?

The process disappointed him. I've heard other book proposal horror stories. Tim Ferriss' book "The 4-Hour Workweek" was criticized.

Because he has thick skin, his book came out. He wouldn't be known without that.

I hate book proposals.

An ongoing commitment

Writing a book is time-consuming.

I appreciate time most. I want to focus on my daughter for the next few years. I can't recreate her childhood because of a book.

No idea how parents balance kids' goals.

My silly face in a bookstore. Really?

Genuine thought.

I don't want my face in bookstores. I fear fame. I prefer anonymity.

I want to purchase a property in a bad Australian area, then piss off and play drums. Is bookselling worth it?

Are there even bookstores anymore?

(Except for Ryan Holiday's legendary Painted Porch Bookshop in Texas.)

What's most important about books

Many were duped.

Tweets and TikTok hopscotch vids are their future. Short-form content creates devoted audiences that buy newsletter subscriptions.

Books=depth.

Depth wins (if you can get people to buy your book). Creating a book will strengthen my reader relationships.

It's cheaper than my classes, so more people can benefit from my life lessons.

A deeper justification for writing a book

Mind wandered.

If I write this book, my daughter will follow it. "Look what you can do, love, when you ignore critics."

That's my favorite.

I'll be her best leader and teacher. If her dad can accomplish this, she can too.

My kid can read my book when I'm gone to remember her loving father.

Last paragraph made me cry.

The positive

This book thing might make me sound like Karen.

The upside is... Building in public, like I have with online writing, attracts the right people.

Proof-of-work over proposals, beautiful words, or huge aspirations. If you want a book deal, try writing online instead of the old manner.

Next steps

No idea.

I'm a rural Aussie. Writing a book in the big city is intimidating. Will I do it? Lots to think about. Right now, some level of reflection and gratitude feels most appropriate.

Sometimes when you don't feel worthy, it gives you the greatest lessons. That's how I feel about getting offered this book deal.

Perhaps you can relate.

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.

Kim Kardashian created Skky Partners. Consumer products, internet & e-commerce, consumer media, hospitality, and luxury are company targets.

Some call this another Kardashian publicity gimmick.

This maneuver is brilliance upon closer inspection. Why?

1) Kim has amassed a sizable social media fan base:

Over 320 million Instagram and 70 million Twitter users follow Kim Kardashian.

Kim Kardashian's Instagram account ranks 8th. Three Kardashians in top 10 is ridiculous.

This gives her access to consumer data. She knows what people are discussing. Investment firms need this data.

Quality, not quantity, of her followers matters. Studies suggest that her following are more engaged than Selena Gomez and Beyonce's.

Kim's followers are worth roughly $500 million to her brand, according to a research. They trust her and buy what she recommends.

2) She has a special aptitude for identifying trends.

Kim Kardashian can sense trends.

She's always ahead of fashion and beauty trends. She's always trying new things, too. She doesn't mind making mistakes when trying anything new. Her desire to experiment makes her a good business prospector.

Kim has also created a lifestyle brand that followers love. Kim is an entrepreneur, mom, and role model, not just a reality TV star or model. She's established a brand around her appearance, so people want to buy her things.

Her fragrance collection has sold over $100 million since its 2009 introduction, and her Sears apparel line did over $200 million in its first year.

SKIMS is her latest $3.2bn brand. She can establish multibillion-dollar firms with her enormous distribution platform.

Early founders would kill for Kim Kardashian's network.

Making great products is hard, but distribution is more difficult. — David Sacks, All-in-Podcast

3) She can delegate the financial choices to Jay Sammons, one of the greatest in the industry.

Jay Sammons is well-suited to develop Kim Kardashian's new private equity fund.

Sammons has 16 years of consumer investing experience at Carlyle. This will help Kardashian invest in consumer-facing enterprises.

Sammons has invested in Supreme and Beats Electronics, both of which have grown significantly. Sammons' track record and competence make him the obvious choice.

Kim Kardashian and Jay Sammons have joined forces to create a new business endeavor. The agreement will increase Kardashian's commercial empire. Sammons can leverage one of the world's most famous celebrities.

“Together we hope to leverage our complementary expertise to build the next generation consumer and media private equity firm” — Kim Kardashian

Kim Kardashian is a successful businesswoman. She developed an empire by leveraging social media to connect with fans. By developing a global lifestyle brand, she has sold things and experiences that have made her one of the world's richest celebrities.

She's a shrewd entrepreneur who knows how to maximize on herself and her image.

Imagine how much interest Kim K will bring to private equity and venture capital.

I'm curious about the company's growth.