Are you an idiot at fundraising?

Humans undervalue what they don't grasp. Consider NASCAR. How is that a sport? ask uneducated observers. Circular traffic. Driving near a car's physical limits is different from daily driving. When driving at 200 mph, seemingly simple things like changing gas weight or asphalt temperature might be life-or-death.

Venture investors do something similar in entrepreneurship. Most entrepreneurs don't realize how complex venture finance is.

In my early startup days, I didn't comprehend venture capital's intricacy. I thought VCs were rich folks looking for the next Mark Zuckerberg. I was meant to be a sleek, enthusiastic young entrepreneur who could razzle-dazzle investors.

Finally, one of the VCs I was trying to woo set me straight. He insulted me.

How I learned that I was approaching the wrong investor

I was constructing a consumer-facing, pre-revenue marketplace firm. I looked for investors in my old university's alumni database. My city had one. After some research, I learned he was a partner at a growth-stage, energy-focused VC company with billions under management.

Billions? I thought. Surely he can write a million-dollar cheque. He'd hardly notice.

I emailed the VC about our shared alumni status, explaining that I was building a startup in the area and wanted advice. When he agreed to meet the next week, I prepared my pitch deck.

First error.

The meeting seemed like a funding request. Imagine the awkwardness.

His assistant walked me to the firm's conference room and told me her boss was running late. While waiting, I prepared my pitch. I connected my computer to the projector, queued up my PowerPoint slides, and waited for the VC.

He didn't say hello or apologize when he entered a few minutes later. What are you doing?

Hi! I said, Confused but confident. Dinin Aaron. My startup's pitch.

Who? Suspicious, he replied. Your email says otherwise. You wanted help.

I said, "Isn't that a euphemism for contacting investors?" Fundraising I figured I should pitch you.

As he sat down, he smiled and said, "Put away your computer." You need to study venture capital.

Recognizing the business aspects of venture capital

The VC taught me venture capital in an hour. Young entrepreneur me needed this lesson. I assume you need it, so I'm sharing it.

Most people view venture money from an entrepreneur's perspective, he said. They envision a world where venture capital serves entrepreneurs and startups.

As my VC indicated, VCs perceive their work differently. Venture investors don't serve entrepreneurs. Instead, they run businesses. Their product doesn't look like most products. Instead, the VCs you're proposing have recognized an undervalued market segment. By investing in undervalued companies, they hope to profit. It's their investment thesis.

Your company doesn't fit my investment thesis, the venture capitalist told me. Your pitch won't beat my investing theory. I invest in multimillion-dollar clean energy companies. Asking me to invest in you is like ordering a breakfast burrito at a fancy steakhouse. They could, but why? They don't do that.

Yeah, I’m not a fine steak yet, I laughed, feeling like a fool for pitching a growth-stage VC used to looking at energy businesses with millions in revenues on my pre-revenue, consumer startup.

He stressed that it's not necessary. There are investors targeting your company. Not me. Find investors and pitch them.

Remember this when fundraising. Your investors aren't philanthropists who want to help entrepreneurs realize their company goals. Venture capital is a sophisticated investment strategy, and VC firm managers are industry experts. They're looking for companies that meet their investment criteria. As a young entrepreneur, I didn't grasp this, which is why I struggled to raise money. In retrospect, I probably seemed like an idiot. Hopefully, you won't after reading this.

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.

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!

"GTO" (Game Theory Optimal) has been used a lot in poker recently. To clarify its meaning and application, the aim of this article is to define what it is, when to use it when playing, what strategies to apply for how to play GTO poker, for beginner and more advanced players!

Poker GTO

In poker, you can choose between two main winning strategies:

Exploitative play maximizes expected value (EV) by countering opponents' sub-optimal plays and weaker tendencies. Yes, playing this way opens you up to being exploited, but the weaker opponents you're targeting won't change their game to counteract this, allowing you to reap maximum profits over the long run.

GTO (Game-Theory Optimal): You try to play perfect poker, which forces your opponents to make mistakes (which is where almost all of your profit will be derived from). It mixes bluffs or semi-bluffs with value bets, clarifies bet sizes, and more.

GTO vs. Exploitative: Which is Better in Poker?

Before diving into GTO poker strategy, it's important to know which of these two play styles is more profitable for beginners and advanced players. The simple answer is probably both, but usually more exploitable.

Most players don't play GTO poker and can be exploited in their gameplay and strategy, allowing for more profits to be made using an exploitative approach. In fact, it’s only in some of the largest games at the highest stakes that GTO concepts are fully utilized and seen in practice, and even then, exploitative plays are still sometimes used.

Knowing, understanding, and applying GTO poker basics will create a solid foundation for your poker game. It's also important to understand GTO so you can deviate from it to maximize profits.

GTO Poker Strategy

According to Ed Miller's book "Poker's 1%," the most fundamental concept that only elite poker players understand is frequency, which could be in relation to cbets, bluffs, folds, calls, raises, etc.

GTO poker solvers (downloadable online software) give solutions for how to play optimally in any given spot and often recommend using mixed strategies based on select frequencies.

In a river situation, a solver may tell you to call 70% of the time and fold 30%. It may also suggest calling 50% of the time, folding 35% of the time, and raising 15% of the time (with a certain range of hands).

Frequencies are a fundamental and often unrecognized part of poker, but they run through these 5 GTO concepts.

1. Preflop ranges

To compensate for positional disadvantage, out-of-position players must open tighter hand ranges.

Premium starting hands aren't enough, though. Considering GTO poker ranges and principles, you want a good, balanced starting hand range from each position with at least some hands that can make a strong poker hand regardless of the flop texture (low, mid, high, disconnected, etc).

Below is a GTO preflop beginner poker chart for online 6-max play, showing which hand ranges one should open-raise with. Table positions are color-coded (see key below).

NOTE: For GTO play, it's advisable to use a mixed strategy for opening in the small blind, combining open-limps and open-raises for various hands. This cannot be illustrated with the color system used for the chart.

Choosing which hands to play is often a math problem, as discussed below.

Other preflop GTO poker charts include which hands to play after a raise, which to 3bet, etc. Solvers can help you decide which preflop hands to play (call, raise, re-raise, etc.).

2. Pot Odds

Always make +EV decisions that profit you as a poker player. Understanding pot odds (and equity) can help.

Postflop Pot Odds

Let’s say that we have JhTh on a board of 9h8h2s4c (open-ended straight-flush draw).  We have $40 left and $50 in the pot. He has you covered and goes all-in. As calling or folding are our only options, playing GTO involves calculating whether a call is +EV or –EV. (The hand was empty.)

Any remaining heart, Queen, or 7 wins the hand. This means we can improve 15 of 46 unknown cards, or 32.6% of the time.

What if our opponent has a set? The 4h or 2h could give us a flush, but it could also give the villain a boat. If we reduce outs from 15 to 14.5, our equity would be 31.5%.

We must now calculate pot odds.

(bet/(our bet+pot)) = pot odds

= $50 / ($40 + $90)

= $40 / $130

= 30.7%

To make a profitable call, we need at least 30.7% equity. This is a profitable call as we have 31.5% equity (even if villain has a set). Yes, we will lose most of the time, but we will make a small profit in the long run, making a call correct.

Pot odds aren't just for draws, either. If an opponent bets 50% pot, you get 3 to 1 odds on a call, so you must win 25% of the time to be profitable. If your current hand has more than 25% equity against your opponent's perceived range, call.

Preflop Pot Odds

Preflop, you raise to 3bb and the button 3bets to 9bb. You must decide how to act. In situations like these, we can actually use pot odds to assist our decision-making.

This pot is:

(our open+3bet size+small blind+big blind)

(3bb+9bb+0.5bb+1bb)

= 13.5

This means we must call 6bb to win a pot of 13.5bb, which requires 30.7% equity against the 3bettor's range.

Three additional factors must be considered:

Being out of position on our opponent makes it harder to realize our hand's equity, as he can use his position to put us in tough spots. To profitably continue against villain's hand range, we should add 7% to our equity.

Implied Odds / Reverse Implied Odds: The ability to win or lose significantly more post-flop (than pre-flop) based on our remaining stack.

While statistics on 3bet stats can be gained with a large enough sample size (i.e. 8% 3bet stat from button), the numbers don't tell us which 8% of hands villain could be 3betting with. Both polarized and depolarized charts below show 8% of possible hands.

7.4% of hands are depolarized.

Polarized Hand range (7.54%):

Each hand range has different contents. We don't know if he 3bets some hands and calls or folds others.

Using an exploitable strategy can help you play a hand range correctly. The next GTO concept will make things easier.

3. Minimum Defense Frequency:

This concept refers to the % of our range we must continue with (by calling or raising) to avoid being exploited by our opponents. This concept is most often used off-table and is difficult to apply in-game.

These beginner GTO concepts will help your decision-making during a hand, especially against aggressive opponents.

MDF formula:

MDF = POT SIZE/(POT SIZE+BET SIZE)

Here's a poker GTO chart of common bet sizes and minimum defense frequency.

Take the number of hand combos in your starting hand range and use the MDF to determine which hands to continue with. Choose hands with the most playability and equity against your opponent's betting range.

Say you open-raise HJ and BB calls. Qh9h6c flop. Your opponent leads you for a half-pot bet. MDF suggests keeping 67% of our range.

Using the above starting hand chart, we can determine that the HJ opens 254 combos:

We must defend 67% of these hands, or 170 combos, according to MDF. Hands we should keep include:

Flush draws

Open-Ended Straight Draws

Gut-Shot Straight Draws

Overcards

Any Pair or better

So, our flop continuing range could be:

Some highlights:

Fours and fives have little chance of improving on the turn or river.

We only continue with AX hearts (with a flush draw) without a pair or better.

We'll also include 4 AJo combos, all of which have the Ace of hearts, and AcJh, which can block a backdoor nut flush combo.

Let's assume all these hands are called and the turn is blank (2 of spades). Opponent bets full-pot. MDF says we must defend 50% of our flop continuing range, or 85 of 170 combos, to be unexploitable. This strategy includes our best flush draws, straight draws, and made hands.

Here, we keep combining:

Nut flush draws

Pair + flush draws

GS + flush draws

Second Pair, Top Kicker+

One combo of JJ that doesn’t block the flush draw or backdoor flush draw.

On the river, we can fold our missed draws and keep our best made hands. When calling with weaker hands, consider blocker effects and card removal to avoid overcalling and decide which combos to continue.

4. Poker GTO Bet Sizing

To avoid being exploited, balance your bluffs and value bets. Your betting range depends on how much you bet (in relation to the pot). This concept only applies on the river, as draws (bluffs) on the flop and turn still have equity (and are therefore total bluffs).

On the flop, you want a 2:1 bluff-to-value-bet ratio. On the flop, there won't be as many made hands as on the river, and your bluffs will usually contain equity. The turn should have a "bluffing" ratio of 1:1. Use the chart below to determine GTO river bluff frequencies (relative to your bet size):

This chart relates to your opponent's pot odds. If you bet 50% pot, your opponent gets 3:1 odds and must win 25% of the time to call. Poker GTO theory suggests including 25% bluff combinations in your betting range so you're indifferent to your opponent calling or folding.

Best river bluffs don't block hands you want your opponent to have (or not have). For example, betting with missed Ace-high flush draws is often a mistake because you block a missed flush draw you want your opponent to have when bluffing on the river (meaning that it would subsequently be less likely he would have it, if you held two of the flush draw cards). Ace-high usually has some river showdown value.

If you had a 3-flush on the river and wanted to raise, you could bluff raise with AX combos holding the bluff suit Ace. Blocking the nut flush prevents your opponent from using that combo.

5. Bet Sizes and Frequency

GTO beginner strategies aren't just bluffs and value bets. They show how often and how much to bet in certain spots. Top players have benefited greatly from poker solvers, which we'll discuss next.

GTO Poker Software

In recent years, various poker GTO solvers have been released to help beginner, intermediate, and advanced players play balanced/GTO poker in various situations.

PokerSnowie and PioSolver are popular GTO and poker study programs.

While you can't compute players' hand ranges and what hands to bet or check with in real time, studying GTO play strategies with these programs will pay off. It will improve your poker thinking and understanding.

Solvers can help you balance ranges, choose optimal bet sizes, and master cbet frequencies.

GTO Poker Tournament

Late-stage tournaments have shorter stacks than cash games. In order to follow GTO poker guidelines, Nash charts have been created, tweaked, and used for many years (and also when to call, depending on what number of big blinds you have when you find yourself shortstacked).

The charts are for heads-up push/fold. In a multi-player game, the "pusher" chart can only be used if play is folded to you in the small blind. The "caller" chart can only be used if you're in the big blind and assumes a small blind "pusher" (with a much wider range than if a player in another position was open-shoving).

Divide the pusher chart's numbers by 2 to see which hand to use from the Button. Divide the original chart numbers by 4 to find the CO's pushing range. Some of the figures will be impossible to calculate accurately for the CO or positions to the right of the blinds because the chart's highest figure is "20+" big blinds, which is also used for a wide range of hands in the push chart.

Both of the GTO charts below are ideal for heads-up play, but exploitable HU shortstack strategies can lead to more +EV decisions against certain opponents. Following the charts will make your play GTO and unexploitable.

Poker pro Max Silver created the GTO push/fold software SnapShove. (It's accessible online at www.snapshove.com or as iOS or Android apps.)

Players can access GTO shove range examples in the full version. (You can customize the number of big blinds you have, your position, the size of the ante, and many other options.)

In Conclusion

Due to the constantly changing poker landscape, players are always improving their skills. Exploitable strategies often yield higher profit margins than GTO-based approaches, but knowing GTO beginner and advanced concepts can give you an edge for a few reasons.

It creates a solid gameplay base.

Having a baseline makes it easier to exploit certain villains.

You can avoid leveling wars with your opponents by making sound poker decisions based on GTO strategy.

It doesn't require assuming opponents' play styles.

Not results-oriented.

This is just the beginning of GTO and poker theory. Consider investing in the GTO poker solver software listed above to improve your game.

What works and what’s just more toxic positivity

Just keep at it; you’ll get it.

I closed the Zoom call and immediately dropped my head. Open tabs included material on inspiration, burnout, and recovery.

I searched everywhere for ways to avoid burnout.

It wasn't that I needed to keep going, change my routine, employ 8D audio playlists, or come up with fresh ideas. I had several ideas and a schedule. I knew what to do.

I wasn't interested. I kept reading, changing my self-care and mental health routines, and writing even though it was tiring.

Since burnout became a psychiatric illness in 2019, thousands have shared their experiences. It's spreading rapidly among writers.

What is the actual key to recovering from burnout?

Every A-list burnout story emphasizes prevention. Other lists provide repackaged self-care tips. More discuss mental health.

It's like the mid-2000s, when pink quotes about bubble baths saturated social media.

The self-care mania cost us all. Self-care is crucial, but utilizing it to address everything didn't work then or now.

How can you recover from burnout?

Time

Are extended breaks actually good for you? Most people need a break every 62 days or so to avoid burnout.

Real-life burnout victims all took breaks. Perhaps not a long hiatus, but breaks nonetheless.

Burnout is slow and gradual. It takes little bits of your motivation and passion at a time. Sometimes it’s so slow that you barely notice or blame it on other things like stress and poor sleep.

Burnout doesn't come overnight; neither will recovery.

I don’t care what anyone else says the cure for burnout is. It has to be time because time is what gave us all burnout in the first place.