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.

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.

People-first update.

Every Google upgrade causes website owners to panic.

Some have just recovered from previous algorithm tweaks and resumed content development.

If you follow Google's Webmaster rules, you shouldn't fear its adjustments.

Everyone has a view of them. Miscommunication and confusion result.

Now, for some (hopefully) exciting news.

Google tweeted on August 18, 2022 about a fresh content update.

This change is another Google effort to remove low-quality, repetitive, and AI-generated content.

The algorithm generates and analyzes search results, not humans.

Google spends a lot to teach its algorithm what searchers want. Intent isn't always clear.

Google's content update aims to:

“… ensure people see more original, helpful content written by people, for people, in search results.”

Isn't it a noble goal?

However, what does it mean for content creators and website owners?

How can you ensure you’re creating content that will be successful after the updates roll out?

Let's first define people-first content.

What does "people-first-content" mean?

If asked, I'd say information written to answer queries and solve problems.

Like others, I read it from the term.

Content creators and marketers disagree. They need more information to follow recommendations.

Google gives explicit instructions for creating people-first content.

According to Google, if you answer yes to the following questions, you have a people-first attitude.

1. Do you have customers who might find your content useful if they contacted you directly?

2. Does your content show the breadth of your knowledge?

3. Do you have a niche or a focus for your website?

4. After reading your content, will readers learn something new to aid them in achieving their goals?

5. Are readers happy after reading your content?

6. Have you been adhering to Google's fundamental updates and product reviews?

As an SEO writer, I'm not scared.

I’ve been following these rules consciously while creating content for my website. That’s why it’s been steadily growing despite me publishing just one or two stories a month.

If you avoid AI-generated text and redundant, shallow material, your website won't suffer.

If you use unscrupulous methods to boost your website's traffic, including link buying or keyword stuffing, stop. Google is getting smarter and will find and punish your site eventually.

For those who say, “SEO is no longer working,” I dedicated the whole paragraph below.

This does not imply that SEO is obsolete.

Google:

“People-first content creators focus on creating satisfying content, while also utilizing SEO best practices to bring searchers additional value.”

The official helpful content update page lists two people-first content components:

• meeting user needs

• best practices for SEO

Always read official guidelines, not unsolicited suggestions.

SEO will work till search engines die.

How to use the update

Google said the changes will arrive in August 2022.

They pledged to post updates on Google's search ranking updates page.

Google also tweets this info. If you haven't followed it already, I recommend it.

Ranking adjustments could take two weeks and will affect English searches internationally initially.

Google affirmed plans to extend to other languages.

If you own a website, monitor your rankings and traffic to see if it's affected.

Building A Second Brain helps us remember connections, ideas, inspirations, and insights. Using contemporary technologies and networks increases our intelligence.

This approach makes and preserves concepts. It's a straightforward, practical way to construct a second brain—a remote, centralized digital store for your knowledge and its sources.

How to build ‘The Second Brain’

Have you forgotten any brilliant ideas? What insights have you ignored?

We're pressured to read, listen, and watch informative content. Where did the data go? What happened?

Our brains can store few thoughts at once. Our brains aren't idea banks.

Building a Second Brain helps us remember thoughts, connections, and insights. Using digital technologies and networks expands our minds.

Ten Rules for Creating a Second Brain

1. Creative Stealing

Instead of starting from scratch, integrate other people's ideas with your own.

This way, you won't waste hours starting from scratch and can focus on achieving your goals.

Users of Notion can utilize and customize each other's templates.

2. The Habit of Capture

We must record every idea, concept, or piece of information that catches our attention since our minds are fragile.

When reading a book, listening to a podcast, or engaging in any other topic-related activity, save and use anything that resonates with you.

3. Recycle Your Ideas

Reusing our own ideas across projects might be advantageous since it helps us tie new information to what we already know and avoids us from starting a project with no ideas.

4. Projects Outside of Category

Instead of saving an idea in a folder, group it with documents for a project or activity.

If you want to be more productive, gather suggestions.

5. Burns Slowly

Even if you could finish a job, work, or activity if you focused on it, you shouldn't.

You'll get tired and can't advance many projects. It's easier to divide your routine into daily tasks.

Few hours of daily study is more productive and healthier than entire nights.

6. Begin with a surplus

Instead of starting with a blank sheet when tackling a new subject, utilise previous articles and research.

You may have read or saved related material.

7. Intermediate Packets

A bunch of essay facts.

You can utilize it as a document's section or paragraph for different tasks.

Memorize useful information so you can use it later.

8. You only know what you make

We can see, hear, and read about anything.

What matters is what we do with the information, whether that's summarizing it or writing about it.

9. Make it simpler for yourself in the future.

Create documents or files that your future self can easily understand. Use your own words, mind maps, or explanations.

10. Keep your thoughts flowing.

If you don't employ the knowledge in your second brain, it's useless.

Few people exercise despite knowing its benefits.

Conclusion:

• You may continually move your activities and goals closer to completion by organizing and applying your information in a way that is results-focused.

• Profit from the information economy's explosive growth by turning your specialized knowledge into cash.

• Make up original patterns and linkages between topics.

• You may reduce stress and information overload by appropriately curating and managing your personal information stream.

• Learn how to apply your significant experience and specific knowledge to a new job, business, or profession.

• Without having to adhere to tight, time-consuming constraints, accumulate a body of relevant knowledge and concepts over time.

• Take advantage of all the learning materials that are at your disposal, including podcasts, online courses, webinars, books, and articles.

https://tomconnor.me/wp-content/uploads/2021/08/10x-Engineer-Mental-Models.pdf

I keep returning to the same mental models and tricks after writing and reading about a wide range of topics.

Top 12 mental models

12.

Survival bias - We perceive the surviving population as remarkable, yet they may have gotten there through sheer grit.

Survivorship bias affects us in many situations. Our retirement fund; the unicorn business; the winning team. We often study and imitate the last one standing. This can lead to genuine insights and performance improvements, but it can also lead us astray because the leader may just be lucky.

11.

The Helsinki Bus Theory - How to persevere Buss up!

Always display new work, and always be compared to others. Why? Easy. Keep riding. Stay on the fucking bus.

10.

Until it sticks… Turning up every day… — Artists teach engineers plenty. Quality work over a career comes from showing up every day and starting.

9.

WRAP decision making process (Heath Brothers)

Decision-making WRAP Model:

W — Widen your Options

R — Reality test your assumptions

A — Attain Distance

P — Prepare to be wrong or Right

8.

Systems for knowledge worker excellence - Todd Henry and Cal Newport write about techniques knowledge workers can employ to build a creative rhythm and do better work.

Todd Henry's FRESH framework:

1. Focus: Keep the start in mind as you wrap up.

2. Relationships: close a loop that's open.

3. Pruning is an energy.

4. Set aside time to be inspired by stimuli.

5. Hours: Spend time thinking.

7.

Black Box Thinking…..

BBT is learning from mistakes. Science has transformed the world because it constantly updates its theories in light of failures. Complexity guarantees failure. Do we learn or self-justify?

6.

The OODA Loop - Competitive advantage

O: Observe: collect the data. Figure out exactly where you are, what’s happening.

O: Orient: analyze/synthesize the data to form an accurate picture.

D: Decide: select an action from possible options

A: Action: execute the action, and return to step (1)

Boyd's approach indicates that speed and agility are about information processing, not physical reactions. They form feedback loops. More OODA loops improve speed.

5.

Know your Domain 

Leaders who try to impose order in a complex situation fail; those who set the stage, step back, and allow patterns to develop win.

https://vimeo.com/640941172?embedded=true&source=vimeo_logo&owner=11999906

4.

The Three Critical Gaps

• Information Gap - The discrepancy between what we know and what we would like to know

• Gap in Alignment - What individuals actually do as opposed to what we wish them to do

• Effects Gap - the discrepancy between our expectations and the results of our actions

3.

Theory of Constraints — The Goal  - To maximize system production, maximize bottleneck throughput.

• Goldratt creates a five-step procedure:

1. Determine the restriction

2. Improve the restriction.

3. Everything else should be based on the limitation.

4. Increase the restriction

5. Go back to step 1 Avoid letting inertia become a limitation.

Any non-constraint improvement is an illusion.

2.

Serendipity and the Adjacent Possible - Why do several amazing ideas emerge at once? How can you foster serendipity in your work?

You need specialized abilities to reach to the edge of possibilities, where you can pursue exciting tasks that will change the world. Few people do it since it takes a lot of hard work. You'll stand out if you do.

Most people simply lack the comfort with discomfort required to tackle really hard things. At some point, in other words, there’s no way getting around the necessity to clear your calendar, shut down your phone, and spend several hard days trying to make sense of the damn proof.

1.

Boundaries of failure - Rasmussen's accident model.

Rasmussen modeled this. It has economic, workload, and performance boundaries.

The economic boundary is a company's profit zone. If the lights are on, you're within the economic boundaries, but there's pressure to cut costs and do more.

Performance limit reflects system capacity. Taking shortcuts is a human desire to minimize work. This is often necessary to survive because there's always more labor.

Both push operating points toward acceptable performance. Personal or process safety, or equipment performance.

If you exceed acceptable performance, you'll push back, typically forcefully.