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.

Prudence is advised. Be debt-free. Be frugal. Spend less.

This advice sounds nice, but it rarely works.

Most people never learn these two money rules. Both approaches will impact how you see personal finance.

It may safeguard you from inflation or the inability to preserve money.

Let’s dive in.

#1: Making long-term debt your ally

High-interest debt hurts consumers. Many credit cards carry 25% yearly interest (or more), so always pay on time. Otherwise, you’re losing money.

Some low-interest debt is good. Especially when buying an appreciating asset with borrowed money.

Inflation helps you.

If you borrow $800,000 at 3% interest and invest it at 7%, you'll make $32,000 (4%).

As money loses value, fixed payments get cheaper. Your assets' value and cash flow rise.

The never-in-debt crowd doesn't know this. They lose money paying off mortgages and low-interest loans early when they could have bought assets instead.

#2: How To Buy Or Build Assets To Make Inflation Irrelevant

Dozens of studies demonstrate actual wage growth is static; $2.50 in 1964 was equivalent to $22.65 now.

These reports never give solutions unless they're selling gold.

But there is one.

Assets beat inflation.

$100 invested into the S&P 500 would have an inflation-adjusted return of 17,739.30%.

Likewise, you can build assets from nothing.  Doing is easy and quick. The returns can boost your income by 10% or more.

The people who obsess over inflation inadvertently make the problem worse for themselves.  They wait for The Big Crash to buy assets. Or they moan about debt clocks and spending bills instead of seeking a solution.

Conclusion

Being ultra-prudent is like playing golf with a putter to avoid hitting the ball into the water. Sure, you might not slice a drive into the pond. But, you aren’t going to play well either. Or have very much fun.

Money has rules.

Avoiding debt or investment risks will limit your rewards. Long-term, being too cautious hurts your finances.

Disclaimer: This article is for entertainment purposes only. It is not financial advice, always do your own research.

I started smoking in 2002 at IIT BHU. Most of us thought it was enjoyable at first. I didn't realize the cost later.

In 2005, during my final semester, I lost my father. Suddenly, I felt more accountable for my mother and myself.

I quit before starting my first job in Bangalore. I didn't see any smoking friends in my hometown for 2 months before moving to Bangalore.

For the next 5-6 years, I had no regimen and smoked only when drinking.

Due to personal concerns, I started smoking again after my 2011 marriage. Now smoking was a constant guilty pleasure.

I smoked 3-4 cigarettes a day, but never in front of my family or on weekends. I used to excuse this with pride! First office ritual: smoking. Even with guilt, I couldn't stop this time because of personal concerns.

After 8-9 years, in mid 2019, a personal development program solved all my problems. I felt complete in myself. After this, I just needed one cigarette each day.

The hardest thing was leaving this final cigarette behind, even though I didn't want it.

James Clear's Atomic Habits was published last year. I'd only read 2-3 non-tech books before reading this one in August 2021. I knew everything but couldn't use it.

In April 2022, I realized the compounding effect of a bad habit thanks to my subconscious mind. 1 cigarette per day (excluding weekends) equals 240 = 24 packs per year, which is a lot. No matter how much I did, it felt negative.

Then I applied the 2nd principle of this book, identifying the trigger. I tried to identify all the major triggers of smoking. I found social drinking is one of them & If I am able to control it during that time, I can easily control it in other situations as well. Going further whenever I drank, I was pre-determined to ignore the craving at any cost. Believe me, it was very hard initially but gradually this craving started fading away even with drinks.

I've been smoke-free for 3 months. Now I know a bad habit's effects. After realizing the power of habits, I'm developing other good habits which I ignored all my life.

Choose.

DNA makes us distinct.

We act alike. Most people follow the same road, ignoring differences. We remain quiet about our uniqueness for fear of exclusion (family, social background, religion). We live a more or less imposed life.

Off the beaten path, we stand out from the others. We obey without realizing we're sewing a shroud. We're told to do as everyone else and spend 40 years dreaming of a golden retirement and regretting not living.

“One of the greatest regrets in life is being what others would want you to be, rather than being yourself.” - Shannon L. Alder

Others dare. Again, few are creative; most follow the example of those who establish a business for the sake of entrepreneurship. To live.

They pick a potential market and model their MVP on an existing solution. Most mimic others, alter a few things, appear to be original, and end up with bland products, adding to an already crowded market.

SaaS, PaaS, etc. followed suit. It's reduced pricing, profitability, and product lifespan.

As competitors become more aggressive, their profitability diminishes, making life horrible for them and their employees. They fail to innovate, cut costs, and close their company.

Few of them look happy and fulfilled.

How did they do it?

The answer is unsettlingly simple.

They are themselves.

• They start their company, propelled at first by a passion or maybe a calling.

• Then, at their own pace, they create it with the intention of resolving a dilemma.

• They assess what others are doing and consider how they might improve it.

• In contrast to them, they respond to it in their own way by adding a unique personal touch. Therefore, it is obvious.

Originals, like their DNA, can't be copied. Or if they are, they're poorly printed. Originals are unmatched. Artist-like. True collectors only buy Picasso paintings by the master, not forgeries, no matter how good.

Imaginative people are constantly ahead. Copycats fall behind unless they innovate. They watch their competition continuously. Their solution or product isn't sexy. They hope to cash in on their copied product by flooding the market.

They're mostly pirates. They're short-sighted, unlike creators.

Creators see further ahead and have no rivals. They use copiers to confirm a necessity. To maintain their individuality, creators avoid copying others. They find copying boring. It's boring. They oppose plagiarism.

It's thrilling and inspiring.

It will also make them more able to withstand their opponents' tension. Not to mention roadblocks. For creators, impediments are games.

Others fear it. They race against the clock and fear threats that could interrupt their momentum since they lack inventiveness and their product has a short life cycle.

Creators have time on their side. They're dedicated. Clearly. Passionate booksellers will have their own bookstore. Their passion shows in their book choices. Only the ones they love.

The copier wants to display as many as possible, including mediocre authors, and will cut costs. All this to dominate the market. They're digging their own grave.

The bookseller is just one example. I could give you tons of them.

Closing remarks

Entrepreneurs might follow others or be themselves. They risk exhaustion trying to predict what their followers will do.

It's true.

Life offers choices.

Being oneself or doing as others do, with the possibility of regretting not expressing our uniqueness and not having lived.

“Be yourself; everyone else is already taken”. Oscar Wilde

The choice is yours.

I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!

Reflections on the closed company Hola! Dating app

I'll discuss my fuckups as an entrepreneur and CEO. All of them refer to the dating app Hola!, which I co-founded and starred in.

Spring 2021 was when we started. Two techies and two non-techies created a dating app. Pokemon Go and Tinder were combined.

Online dating is a business, and it takes two weeks from a like to a date. We questioned online dating app users if they met anyone offline last year.

75% replied yes, 50% sometimes, 25% usually.

Offline dating is popular, yet people have concerns.

• Men are reluctant to make mistakes in front of others.

• Women are curious about the background of everyone who approaches them.

We designed unique mechanics that let people date after a match. No endless chitchat. Women would be safe while men felt like cowboys.

I wish to emphasize three faults that lead to founders' estrangement.

This detachment ultimately led to us shutting down the company.

The wrong technology stack

Situation

Instead of generating a faster MVP and designing an app in a universal stack for iOS and Android, I argued we should pilot the app separately for iOS and Android. Technical founders' expertise made this possible.

Self-reflection

Mistaken strategy. We lost time and resources developing two apps at once. We chose iOS since it's more profitable. Apple took us out after the release, citing Guideline 4.3 Spam. After 4 months, we had nothing. We had a long way to go to get the app on Android and the Store.

I suggested creating a uniform platform for the company's growth. This makes parallel product development easier. The strategist's lack of experience and knowledge made it a piece of crap.

What would I have changed if I could?

We should have designed an Android universal stack. I expected Apple to have issues with a dating app.

Our approach should have been to launch something and subsequently improve it, but prejudice won.

The lesson

Discuss the IT stack with your CTO. It saves time and money. Choose the easiest MVP method.

2. A tardy search for investments

Situation

Though the universe and other founders encouraged me to locate investors first, I started pitching when we almost had an app.

When angels arrived, it was time to close. The app was banned, war broke out, I left the country, and the other co-founders stayed. We had no savings.

Self-reflection

I loved interviewing users. I'm proud of having done 1,000 interviews. I wanted to understand people's pain points and improve the product.

Interview results no longer affected the product. I was terrified to start pitching. I filled out accelerator applications and redid my presentation. You must go through that so you won't be terrified later.

What would I have changed if I could?

Get an external or internal mentor to help me with my first pitch as soon as possible. I'd be supported if criticized. He'd cheer with me if there was enthusiasm.

In 99% of cases, I'm comfortable jumping into the unknown, but there are exceptions. The mentor's encouragement would have prompted me to act sooner.

The lesson

Begin fundraising immediately. Months may pass. Show investors your pre-MVP project. Draw inferences from feedback.

3. Role ambiguity

Situation

My technical co-founders were also part-time lead developers, which produced communication issues. As co-founders, we communicated well and recognized the problems. Stakes, vesting, target markets, and approach were agreed upon.

We were behind schedule. Technical debt and strategic gap grew.

Bi-daily and weekly reviews didn't help. Each time, there were explanations. Inside, I was freaking out.

Self-reflection

I am a fairly easy person to talk to. I always try to stick to agreements; otherwise, my head gets stuffed with unnecessary information, interpretations, and emotions.

Sit down -> talk -> decide -> do -> evaluate the results. Repeat it.

If I don't get detailed comments, I start ruining everyone's mood. If there's a systematic violation of agreements without a good justification, I won't join the project or I'll end the collaboration.

What would I have done otherwise?

This is where it’s scariest to draw conclusions. Probably the most logical thing would have been not to start the project as we started it. But that was already a completely different project. So I would not have done anything differently and would have failed again.

But I drew conclusions for the future.

The lesson

First-time founders should find an adviser or team coach for a strategic session. It helps split the roles and responsibilities.