Here is the ugly stuff, read this if you have a founder in your life or are trying to become one. Your call.

#1 You'll try to talk yourself to sleep, but it won't always work.

As founders, we're all driven. Good and bad, you're restless. Success requires resistance and discipline. Your startup will be on your mind 24/7, and not everyone will have the patience to listen to your worries, ideas, and coffee runs. You become more self-sufficient than ever before.

#2 No one will understand what you're going through unless they've been a founder.

Some of my closest friends don't understand the work that goes into starting a business, and we can't blame them.

#3 You'll feel alienated.

Your problems aren't common; calling your bestie won't help. You must search hard for the right resources. It alienates you from conversations you no longer relate to. (No 4th of July, no long weekends!)

#4 Since you're your "own boss," people assume you have lots of free time.

Do you agree? I was on a webinar with lots of new entrepreneurs, and one woman said, "I started my own business so I could have more time for myself." This may be true for some lucky people, and you can be flexible with your schedule. If you want your business to succeed, you'll probably be its slave for a while.

#5 No time for illness or family emergencies.

Both last month. Oh, no! Physically and emotionally withdrawing at the worst times will give you perspective. I learned this the hard way because I was too stubborn to postpone an important interview. I thought if I rested all day and only took one call, I'd be fine. Nope. I had a fever and my mind wasn't as sharp, so my performance and audience interaction suffered. Nope. Better to delay than miss out.

Oh, and setting a "OoO" makes you cringe.

#6 Good luck with your mental health, perfectionists.

When building a startup, it's difficult to accept that there won't be enough time to do everything. You can't make them all, not perfectly. You must learn to accept things that are done but not perfect.

#7 As a founder, you'll make mistakes, but you'll want to make them quickly so you can learn.

Hard lessons are learned quicker. You'll need to pivot and try new things often; some won't work, and it's best to discover them sooner rather than later.

#8 Pyramid schemes abound.

I didn't realize how bad it was until I started a company. You must spy and constantly research. As a founder, you'll receive many emails from people claiming to "support" you. Be wary and keep your eyes open. When it's too good to be true. Some "companies" will try to get you to pay for "competitions" to "pitch at events." Don't do it.

#9 Keep your competitor research to a minimum.

Actually, competition is good. It means there's a market for those solutions. However, this can be mentally exhausting too. Learn about their geography and updates, but that's it.

#10 You'll feel guilty taking vacation.

I don't know what to say, but I no longer enjoy watching TV, and that's okay. Pay attention to things that enrich you, bring you joy, and have fun. It boosts creativity.

Being a startup founder may be one of the hardest professional challenges you face, but it's also a great learning experience. Your passion will take you places you never imagined and open doors to opportunities you wouldn't have otherwise. You'll meet amazing people. No regrets, no complaints. It's a roller coaster, but the good days are great.

Miss anything? Comment below

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

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.

New social media producers' biggest error

The Treadmill of Social Media Content

New creators focus on the wrong platforms.

They post to Instagram, Twitter, TikTok, etc.

They create daily material, but it's never enough for social media algorithms.

Creators recognize they're on a content creation treadmill.

They have to keep publishing content daily just to stay on the algorithm’s good side and avoid losing the audience they’ve built on the platform.

This is exhausting and unsustainable, causing creator burnout.

They focus on short-lived platforms, which is an issue.

Comparing low- and high-return social media platforms

Social media networks are great for reaching new audiences.

Their algorithm is meant to viralize material.

Social media can use you for their aims if you're not careful.

To master social media, focus on the right platforms.

To do this, we must differentiate low-ROI and high-ROI platforms:

Low ROI platforms are ones where content has a short lifespan. High ROI platforms are ones where content has a longer lifespan.

A tweet may be shown for 12 days. If you write an article or blog post, it could get visitors for 23 years.

ROI is drastically different.

New creators have limited time and high learning curves.

Nothing is possible.

First create content for high-return platforms.

ROI for social media platforms

Here are high-return platforms:

1. Your Blog - A single blog article can rank and attract a ton of targeted traffic for a very long time thanks to the power of SEO.

2. YouTube - YouTube has a reputation for showing search results or sidebar recommendations for videos uploaded 23 years ago. A superb video you make may receive views for a number of years.

3. Medium - A platform dedicated to excellent writing is called Medium. When you write an article about a subject that never goes out of style, you're building a digital asset that can drive visitors indefinitely.

These high ROI platforms let you generate content once and get visitors for years.

This contrasts with low ROI platforms:

1. Twitter

2. Instagram

3. TikTok

4. LinkedIn

5. Facebook

The posts you publish on these networks have a 23-day lifetime. Instagram Reels and TikToks are exceptions since viral content can last months.

If you want to make content creation sustainable and enjoyable, you must focus the majority of your efforts on creating high ROI content first. You can then use the magic of repurposing content to publish content to the lower ROI platforms to increase your reach and exposure.

How To Use Your Content Again

So, you’ve decided to focus on the high ROI platforms.

Great!

You've published an article or a YouTube video.

You worked hard on it.

Now you have fresh stuff.

What now?

If you are not repurposing each piece of content for multiple platforms, you are throwing away your time and efforts.

You've created fantastic material, so why not distribute it across platforms?

Repurposing Content Step-by-Step

For me, it's writing a blog article, but you might start with a video or podcast.

The premise is the same regardless of the medium.

Start by creating content for a high ROI platform (YouTube, Blog Post, Medium). Then, repurpose, edit, and repost it to the lower ROI platforms.

Here's how to repurpose pillar material for other platforms:

1. Post the article on your blog.

2. Put your piece on Medium (use the canonical link to point to your blog as the source for SEO)

3. Create a video and upload it to YouTube using the talking points from the article.

4. Rewrite the piece a little, then post it to LinkedIn.

5. Change the article's format to a Thread and share it on Twitter.

6. Find a few quick quotes throughout the article, then use them in tweets or Instagram quote posts.

7. Create a carousel for Instagram and LinkedIn using screenshots from the Twitter Thread.

8. Go through your film and select a few valuable 30-second segments. Share them on LinkedIn, Facebook, Twitter, TikTok, YouTube Shorts, and Instagram Reels.

9. Your video's audio can be taken out and uploaded as a podcast episode.

If you (or your team) achieve all this, you'll have 20-30 pieces of social media content.

If you're just starting, I wouldn't advocate doing all of this at once.

Instead, focus on a few platforms with this method.

You can outsource this as your company expands. (If you'd want to learn more about content repurposing, contact me.)

You may focus on relevant work while someone else grows your social media on autopilot.

You develop high-ROI pillar content, and it's automatically chopped up and posted on social media.

This lets you use social media algorithms without getting sucked in.

Thanks for reading!