What were the 10 failures you learned from this past year?

I had an idea:

- I would rollup apps in the e-learning space. Meaning, I would buy small apps that were profitable and combine them together, making a bigger e-learning company. By combining them I would send traffic back and forth to the different apps (each app advertising on the other apps) and increase profits and then sell the bigger company.

- I used Flippa.com to find companies for sale. An app that maybe had $60K in profits per year would be selling for about $120-150k.

- I bought two apps and then used that to demonstrate to investors that this was a viable idea and I had investor commitments up to $15 million.

- At the time I was getting the backlash from my article on NYC and, for the first time ever, I was feeling more than a big overwhelmed from it. So this was effecting my judgment.

- I bought apps that were too complicated for me technically to figure out. Even though I was a software developer for 15 years earlier in my life I had basically lost my abilities in the mobile age. I can manage developers but not do development.

- Rather than hire someone to help me, I still tried to do it myself and I failed miserably.

- I ended up wasting an enormous amount of money and time. And I told the investors that I wasn't doing it anymore so the whole thing fell through. I still have the apps (I think I still have one app, the other disappeared) and I think the idea is still a great one but I burnt out on the idea.

- Learnings:

a. don't bite off more than you can chew.

b. Don't overestimate your abilities (in this case my technical abilities and also my ability at that single moment to deal with the backlash from my articles)

c. I knew this one already but not sure why I didn't do it here: partner and/or delegate to get a big project done.

It was one of the better ideas I've had over the past few years and it was a failure.

Those fees add up quickly. My theory was that I was fine with the fees as long as I was making more with investing. But still, it's a bit stressful at times when letters come reminding you about it.

"Skip the Line" was a very successful book for me. I felt it was my most practical book about how to apply the ideas from "Choose Yourself" and also apply things I had learned since Choose Yourself about persuasion and business and deep learning, etc.

I had great stories and although I was already doing well as a writer I applied many of the techniques I learned from the great authors who had been on my podcast including Robert Greene ("The 48 Laws of Power") who is a deep researcher of historical stories to make his points, and Chuck Pahlaniuk ("Fight Club"), who is a great all around writer

I had gone back to traditional publishing for this one (Harper Collins) and worked with a great agent and a great editor.

The book has done well by many standards. A good number of 5 star reviews (more than most of my books). And I get emails ever day still by people who have read it and it helped them.

But the book did not make a bestseller list and I think it disappointed the publisher.

I'm not sure what I could have done differently on the marketing.

Looking back and comparing it with "Choose Yourself" there were several things that I did differently with "Choose Yourself".

a) I had marketing "gimmicks". That's the wrong word but not sure what else to call it. With "Choose Yourself" I had made a "bitcoin only" store, which got me on CNBC. I also did marketing deals with email lists to provide special deals for their email subscribers. I also offered a money back guarantee for the first 60 days. Less than 1% wanted their money back so that wasn't a big deal.

"Choose Yourself" has sold over 1,000,000 copies.

I could do these things because I controlled the marketing. I was the publisher. But with a traditional publisher I couldn't do those things.

b) I went on a lot more podcasts with "Choose Yourself". For some reason I was more comfortable asking people then than now. I'm not sure why. I really feel funny asking people for help now for some reason.

c) I had a good relationship with Amazon and they were able to help me a little with the marketing. Again, something I could not do with a traditional publisher.

d) I did a reddit AMA which had about 10,000 questions. I should've done that for "Skip the Line".

I think I was a bit more shy about some of these things because some of the backlashes I had gotten since 2013. I don't really know. But when, on occasion, it feels like the world hates you it has a tendency to wear one (me) down. I now realize those backlashes were blips from a small % of people but at the time it felt like the world.

So "Skip the Line" might be my best book but I don't think it did as well for these reasons. And I think that's the last time I deal with this agent and publisher. I don't think they were happy. They even recently released the paperback and nobody told me!

Preview

For awhile we lived in Key Biscayne, FL. I really liked all of the people. We were knew all our neighbors and became very social.

Robyn is definitely an extrovert and I'm an introvert. In NYC, oddly, this wasn't a big issue. It's actually hard to socialize in NYC because everyone was so busy all the time.

And also, I was doing comedy almost every night in NYC so that satisfied Robyn's extrovert tendencies and I enjoyed performing.

In Key Biscayne we met really nice people. And they were all extroverts. So everyone was going out EVERY NIGHT. I couldn't believe it. For HOURS.

And, again, I liked them a lot and wanted to be able to socialize.

But introverts run out of social steam quickly and need to regenerate by spending time alone. This is why I like activities like writing or chess. They give me a lot of satisfaction and replenish my energy.

Extroverts get energy by being with people.

Whenever Robyn and I had a party in NYC every 20 mins or so I'd just go to an empty room and sit there for awhile.

But I couldn't do this in Key Biscayne. I'd be out for hours and hours. And I was going insane. I didn't know how to talk to people and I was feeling not like myself. I wish I had been better at it.

This was a failure for me on the friendship level. I wish I had figured out how to better deal with my introversion and negotiate a little better on how much time out we spent.

Interestingly, the best times I had was when we'd go over someone's house and play card games for the afternoon. Then I was able to socialize while doing my introversion love for playing games.

This is a huge failure of mine.

I have a lot of people I like to keep in touch with. Pre-pandemic it was easier for me to do.

I'd meet people at the comedy club, I'd do more podcasts in person (podcasts are often a way I keep in touch with people: "hey, we'll catch up on my podcast"). And I would just run into people at meetings or conferences or parties or wherever.

But once the pandemic hit we were all cast to our lonely islands.

Which was fine for me. I loved that part of it.

But I'm not a good phone talker and gradually I'd lost touch with people. People would call and I'd think to myself, "I'll return the call tomorrow". But then the next day I wouldn't and then I'd start to feel guilty or ashamed and I'd delay more and before long people would get upset at me and I'd lose touch.

I hope eventually to get back in touch with people. I feel bad about it and have distanced myself from so many good friends.

Again, this is not a failure. But....

I started playing in my tournaments for the first time in 25 years exactly a year ago. My goal was to get an even higher ranking than I had before.

Everyone told me things are different now. That kids rule and that I was too old and my brain was declining.

I said, "That's impossible. MY BRAIN DOES NOT DECLINE!"

One person, International Master Elliot Winslow, told me I might be delusional.

And he might be right.

So what is different?

I've now done a lot of research on age-related cognitive decline. There's a ton of research. Even research specifically done on chess. In particular, the expert on the age-related decline in chess is International Master Fernand Gobet. Funny enough, I knew Fernand back in 1991-1994 and we often played chess together. Plus I was part of some of his initial experiments on this topic.

Here is the issue (here is what I've been learning):

There are two types of intelligence: fluid intelligence and crystallized intelligence.

Fluid intelligence is more about calculation, memory, solving math problems quickly, etc. It's raw calculation speed. These are all the skills that I excelled at all of my life at every activity and career I ever had.

My memory was spotless. My calculation was fast.

This part of intelligence starts to decline at age 50 or earlier. It declines fairly quickly.

This is why mathematicians achieve their greatest successes in their early to mid-20s. This goes for scientists, musicians, and even chess players.

Notably, Magnus Carlsen, the current world chess champion, is 31 but achieved his top ranking in his mid 20s. And in the past few weeks even he's lost games to four teenagers. This is unheard of for Magnus who once went 125 games without a loss.

Crystallized intelligence, on the other hand, is more about recognizing patterns and experiences and then making decisions based on that pattern recognition.

This intelligence keeps increasing into your 80s.

This is why the peak ages for entrepreneurs or in their 50s (this might surprise people but it's true). And for historians they might peak well into their 70s. For writers as well.

So what does this have to do with chess?

Instead of assuming my calculation ability and memory would bounce back quickly after 25 years "on the shelf" I should've focused more on actually studying games of players. This would teach me all the things I never knew about chess - the strategic ideas. i.e. "chess wisdom".

My first tournament back I had six losses and three draws. I can safely say this is my worst tournament ever.

Now I am trying to focus on getting "chess wisdom".

The result is very satisfying from a process point of view. Although I was/am a decent chess player (a nationally ranked master) I feel I now know more than I ever did before about the game. It is a more beautiful game than I could've imagined.

The key for me now is to steer the game into positions I "know" and then the tactics (calculation) become easier. But it means I have to know a lot more. Which I am beginning to do but I am not sure how long the process is.

I remember one time playing international master Greg Shahade some casual blitz games in 2013 and he made a comment that was something like, "it's weird playing you. You're the strongest player I know who seems to know nothing about chess."

At least is this doesn't work out I still have writing.

(image below is Carlsen (age 31) vs Praag (age 16) and Carlsen lost).

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NotePD is obviously not a failure. It's been an amazing success so far.

Without even really launching we have over 14,000 idea lists posted on the site now with over 100,000 individual ideas. I am constantly blown away by the creativity and the community on NotePD. Such an amazing pleasure.

And @paolo , Paulo Rosson, who is my co-founder of NotePD, has been a remarkably good manager of all the development.

We basically now have all the features we wanted (almost all), plus all the mobile apps about to be released. We have AI engines hooked up to the site, premium idea lists, all sorts of community features ,and on and on and the site grows in usage every day. It's a site that is not only fun but actually helps people in their lives in a variety of ways (which could be the topic of other lists).

BUT...one thing I have learned: people don't always want or need to do 10 ideas a day or do it EVERY DAY.

Here's an important thing about business. You learn a lot more from "negative information" than positive information.

I'll tell you one quick story about business:

A friend of mine started a company in the cybersecurity space that did something very unique. He approached one of the biggest companies in the world.

The CTO was his best friend and was the decision maker. The CTO of the company brought in his whole team.

My friend brought his team. They made the pitch. Everyone applauded at the end. The CTO said, "your product could save us $100 million a year. If you just add these new features: X, Y, and Z, then we'll buy your product."

My friend built the features. And the company never bought his product.

Much more important than "We'd love it if you built A, B, and C. We love this product." is negative information.

Find out why someone WILL NOT use your product.

There are many reasons someone might say "Yes" to you (in the above example, they were friends. Friends say "yes" to each other). Another example is someone might say "Yes" to you just to get off the phone with you. And then later say "no".

But there's always a specific reason or two why someone says "No".

We contacted people who tried NotePD for awhile and drifted away. Why did you drift away?

"It was a lot of pressure writing 10 ideas every day!" was the most common response.

This is valuable information! Nobody feels pressure to make tweets, for instance.

So we instantly changed several things.

a.) no more daily email the says, "You are about to break your streak!" We also extended the grace period on streaks if you miss a day or two.

b) we focused more on the challenges. So we put the challenges on the main feed (we weren't doing that before) and the daily email now says something like, "can you answer these questions?" with links to the challenges.

Just those two things alone upped usage considerably and people are having more fun and more collaboration.

We're also going to make it easier for people to just input a single idea and no more pressure on it being ten. And the mobile apps will make it a lot easier for people to read the site anytime.

Also might add a community feature so people can build private communities. Perhaps more collaboration tools.

This has been a valuable lesson in business and the importance of negative information.

A) get help when technically over your head.

B) don't underestimate the effect negativity can have on your other activities (e.g. I was underestimating the effect the backlash on one of my articles was having on my business life).

C) pay taxes on time!!

D) don't be afraid to ask for help

E) try to at least follow the successful ideas from previous but similar projects (e.g. the marketing ideas I used for "Choose Yourself" vs "Skip the Line"

F) crystallized vs fluid intelligence

G) understand the differences between being an introvert and an extrovert. I highly recommend my friend Susan Cain's book "Quiet".

H) respond to people quickly. And don't feel shame if you respond to people late. This is hard but more important is to respond to people you care about.

I) Learn from negative information. This is much more valuable than positive feedback. For EVERY business you can start, you don't really know what your business is about until you start hearing why people DO NOT use what you are doing. Come to think of it, this applies to writing as well.

J) And most importantly, learn from your mistakes. Do a complete autopsy on every aspect of your endeavors that don't work. Leave the ego out of this laboratory and look to criticize yourself on every aspect. This is how you learn.