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 ;)

The comeback tour continues…

First, he founded a $47 billion co-working company (sorry, a “tech company”).

He established WeLive to disrupt apartment life.

Then he created WeGrow, a school that tossed aside the usual curriculum to feed children's souls and release their potential.

He raised the world’s consciousness.

Then he blew it all up (without raising the world’s consciousness). (He bought a wave pool.)

Adam Neumann's WeWork business burned investors' money. The founder sailed off with unimaginable riches, leaving long-time employees with worthless stocks and the company bleeding money. His track record, which includes a failing baby clothing company, should have stopped investors cold.

Once the dust settled, folks went on. We forgot about the Neumanns! We forgot about the private jets, company retreats, many houses, and WeWork's crippling. In that moment, the prodigal son of entrepreneurship returned, choosing the blockchain as his industry. His homecoming tour began with Flowcarbon, which sold Goddess Nature Tokens to lessen companies' carbon footprints.

Did it work?

Of course not.

Despite receiving $70 million from Andreessen Horowitz's a16z, the project has been halted just two months after its announcement.

This triumph should lower his grade.

Neumann seems to have moved on and has another revolutionary idea for the future of living. Flow (not Flowcarbon) aims to help people live in flow and will launch in 2023. It's the classic Neumann pitch: lofty goals, yogababble, and charisma to attract investors.

It's a winning formula for one investment fund. a16z has backed the project with its largest single check, $350 million. It has a splash page and 3,000 rental units, but is valued at over $1 billion. The blog post praised Neumann for reimagining the office and leading a paradigm-shifting global company.

Flow's mission is to solve the nation's housing crisis. How? Idk. It involves offering community-centric services in apartment properties to the same remote workforce he once wooed with free beer and a pingpong table. Revolutionary! It seems the goal is to apply WeWork's goals of transforming physical spaces and building community to apartments to solve many of today's housing problems.

The elevator pitch probably sounded great.

At least a16z knows it's a near-impossible task, calling it a seismic shift. Marc Andreessen opposes affordable housing in his wealthy Silicon Valley town. As details of the project emerge, more investors will likely throw ethics and morals out the window to go with the flow, throwing money at a man known for burning through it while building toxic companies, hoping he can bank another fantasy valuation before it all crashes.

Insanity is repeating the same action and expecting a different result. Everyone on the Neumann hype train needs to sober up.

Like WeWork, this venture Won’tWork.

Like before, it'll cause a shitstorm.

Are you one of these Zoom dogs?

The Person Who Is Apparently Always on Mute

Waffles thinks he can overpower the mute button by shouting loudly.

The person who believed their camera to be off

Barkley's used to remote work, but he hasn't mastered the "Stop Video" button. Everyone is affected.

Who is driving for some reason, exactly?

Why is Pumpkin always late? Who knows? Shouldn't she be driving? If you could hear her over the freeway, she'd answer these questions.

The Person With the Amazing Bookcase

Cicero likes to use SAT-words like "leverage" and "robust" in Zoom sessions, presumably from all the books he wants you to see behind him.

The Individual Who Is Unnecessarily Dressed

We hope Bandit is going somewhere beautiful after this meeting, or else he neglected the quarterly earnings report and is overcompensating to distract us.

The person who works through lunch in between zoom calls

Barksworth has back-to-back meetings all day, so you can watch her eat while she talks.

The Person Who Is A Little Too Comfy

Hercules thinks Zoom meetings happen between sleeps. He'd appreciate everyone speaking more quietly.

The Person Who Answered the Phone Outside

Frisbee has a gorgeous backyard and lives in a place with great weather year-round, and she wants you to think about that during the daily team huddle.

Who Wants You to Pay Attention to Their Pet

Snickers hasn't listened to you in 20 minutes unless you tell her how cute her kitten is.

One who is, for some reason, positioned incorrectly on the screen

Nelson's meetings consist primarily of attempting to figure out how he positioned his laptop so absurdly.

The person who says too many goodbyes

Zeus waves farewell like it's your first day of school while everyone else searches for the "Leave Meeting" button. It's nice.

He who has a poor internet connection

Ziggy's connectivity problems continue... She gives a long speech as everyone waits awkwardly to inform her they missed it.

The Clearly Multitasking Person

Tinkerbell can play fetch during the monthly staff meeting if she works from home, but that's not a good idea.

The Person Using Zoom as a Makeup and Hair Mirror

If Gail and Bob knew Zoom had a "hide self view" option, they'd be distraught.

The person who feels at ease with simply leaving

Rusty bails when a Zoom conference is over. Rusty's concept is decent.

"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.