Fun Friday: Questions for Conversations with Friends

Stealing a bit from Fred Wilson, today is going to be Fun Friday.

Here’s some good questions to have more interesting conversations with friends (and to get to know them better!)

  1. You have to go on a road-trip from Maine to San Diego CA. You have to bring 3 people. Who are they?
  2. Which nicknames have you been called?
  3. What about yourself are you really self-conscious about?
  4. If you had someone following you around all the time what would you have them do?
  5. What is your favorite body part about yourself?
  6. If you had kids would you want them to be smart or good looking?
  7. What’s the favorite thing you’ve bought this year?
  8. What would be the most surprising scientific discovery imaginable?
  9. If you were to do a city wide poll, what would you want to learn?
  10. What’s the worst job you’ve ever had?
  11. We look back now at slavery and are appalled and shocked. What will people look back at us 50 years from now and be shocked and appalled by?
  12. What is something you’ve never told anyone, not because it’s a secret but because you’ve just never told anyone?
  13. What are you curious about?
  14. What’s one bad habit you’re trying to get rid of?
  15. If you can instantly become, what would you want to be an expert in?
  16. If you could be guaranteed one thing in life (besides money), what would it be?
  17. What’s something you believe that almost everyone else disagrees with you about?
  18. If you could live life over again, would you sleep with more people or less? Why?
  19. If you were to die tomorrow, what little thing would you regret not doing?
  20. What normal superpower would you have?
  21. If you could send a message to the entire world, what would you say in 30 seconds?
  22. If you could ask one person one question and they had to answer truthfully, who and what would you ask?
  23. If you had to teach a class on one thing, what would you teach?
  24. If you could change one thing about your life instantly, what would it be?
  25. What feeling do you most wish the English language had a word for but it doesn’t? Describe the last time you felt that way.
  26. What’s the best piece of advice you’ve ever been given?
  27. When you die, what do you want to be remembered for?
  28. Someone gets a text message from you and for whatever reason they’re not sure it’s actually you. They’re worried someone stole your phone. What could they ask to make sure it’s actually you?
  29. What’s something you used to strongly believe that you now think you were fundamentally misguided about?
  30. When you think about success, who comes to mind and why?
  31. Who was your first kiss?
  32. Who did you lose your virginity to?
  33. Have you ever cheated?
  34. What are your showers like?
  35. What is something you like that most people don’t?
  36. What is something most people like that you don’t?
  37. What’s left on your bucket list?
  38. What was your first screen name?
  39. What’d your parents do well and what would you change?
  40. If you could undo 1 moment in your life?
  41. Have you ever been scammed?
  42. Start over at 18 knowing everything you know now. What would you do differently?
  43. When were your parents most disappointed in you?
  44. You can have someone full-time remind you something every day; what would you want?
  45. Which band / artist – dead or alive would play at your funeral?
  46. What 3 words would your friends describe you?
  47. What was your high school superlative?
  48. What was the first book you read that changed your mind?
  49. Brag to me about the best things going on in the past 30 days.
  50. Who’d play you in a movie?
  51. You have $5,000 to spend on someone you love, what would you do with the money?
  52. What book belongs on everyone’s bookshelf?
  53. If there was a sandwich named after you what would be on it?
  54. Last time you lost your temper?
  55. If you could travel back in time to one place or one incident what would it be..and Why?
  56. What’s your best scar or birthmark story?
  57. If you had to delete all but 3 apps from your smartphone, which ones would you keep?
  58. What are you most excited about right now?
  59. What is 1 thing that I don’t know about you?
  60. My pet peeve is…
  61. Have you been to therapy–why? If no, why not?
  62. What are 3 adjectives to describe each of your parents
  63. Buried or cremated?
  64. What would be your best day ever?
  65. What day would you want to repeat forever?
  66. What’s a compliment someone gave you still think about?

(Originally put together by Justin Mares and Noah Kagan, with updates from me).

Finance is a Strange Industry: A Follow Up

A friend posted this article from Morgan Housel at The Motley Fool describing some bizarre things in the investment industry:

I can’t think of another industry:

…in which there is so much ignorance around costs… 

…in which results matter so little…

…that is so important to everyone yet so few care about.

My friend adds:

And yet another friend was recently complaining about a relative whose finances he’d looked over: it turned out the relative was in a high-fee fund that had underperformed for the last 10 years (i.e. its entire existence).

That’s an epic “trip at the finish line” mistake: you spend all your time/money/effort getting educating an education and working so you can make money… and then you screw up and lose a % point or more every year for your entire life. Oh and of course it’s all compounding.

Massive missed wealth since you picked the fund that charged a point more in fees because you didn’t know any better.

This is really weird. 

There’s a few things going on here that, taken together, don’t make a ton of sense:

Point 1: This is one of the most important decisions someone will make in their life: how am I going to invest all the money I’ve made over my entire life from my own blood, sweat, and tears?

Point 2: There’s a lot of people making money selling investments that aren’t fraudulent or illegal but are very costly, to say nothing of the investment’s actual performance.

Point 3: There is a METRIC TON of free advice online about finances and how to invest. The 80/20 rule fits perfectly here IMO and the only financial advice you really need can fit on a 3×5 card:


So there’s plenty of free information, this is a top-10 life importance decision, and yet people screw it up all the time to the collective tune of billions of dollars every year.

What the heck is going on?

Some hypotheses:

  1. People think this is more complicated than it actually is so they’re afraid of it and avoid it altogether.
  2. People are so in the dark that they don’t realize how far into the “you-don’t-know-what-you-don’t-know” zone they are. I could see this being possible since a lot of K-12 public school systems don’t cover personal finance (mine didn’t).
  3. Online information actually is slowly fixing this problem, as evidenced by the recent massive moves into ETFs and passive investment funds. (But so many other confounding variables here, we’d need to see data on fees, etc. etc.)
  4. People just don’t care enough. They have other things to worry about on a short-term basis, and “what’s my retirement fund ROI net of fees” isn’t exactly top of mind.
  5. People are irresponsible and can make decisions that are not in their own best self interest (This goes down the rabbit hole fast, but IMO I think you run into trouble real fast when you assume you know what’s in others’ self interest better than they do.)
  6. Talking about personal finances is taboo in the US so maybe information doesn’t travel well here. For example, if you make a poor investment decision you probably don’t go tell your friends/family “avoid this high-fee fund that I had my life savings in for 7 years”.

Of course it’s probably a combination of all of these and a bunch of other things I didn’t think of.2

As in most things I’m not sure what the big picture answer is here.3

But at a local level the answer is much simpler: read what’s on that damn notecard and be like my friend, make sure your friends and family are following it.

  1. And this isn’t like, a behavior thing that’s hard to change. It’s not like we’re telling people to eat out less. This is a knowledge issue, not action.

  2. You’ll notice that I didn’t mention anything about the investment companies (or the brokers) themselves. I think the best “fixes” to most problems are bottom up: empower the individual and they will know what is best for themselves. By saying the problem is “out there” (i.e. with the companies) we push responsibility of the problem onto entities over which we have no control. Better to focus on what we can actually do, which is to better educate ourselves.

  3.  Adding basic finance training to high school would be nice, but then again a ton of the educational system needs to be redone… it feels like pointing out that Comcast has bad customer service: 1. No kidding, and 2. the real problem goes much deeper.

If you want to be successful…

I don’t remember where I heard it first but this is a favorite quote of mine:

If you want to be successful, start a company. If you want to be more successful, start a country. If you want to be the most successful, start a religion.

And indeed the lifespan of our institutions does tend to run that way: the winning religions last longer than the winning countries which last longer than the winning companies.1

And were they alive today, who would have more social capital?

Jesus > George Washington > Steve Jobs

You see this in current life, too:

Tech CEOs go to meet President-elect Trump, not the other way around


Religion’s power has waned over the last few decades, especially in Europe, but make no mistake: most active believers would give up their country’s citizenship before giving up their faith.

In a way this makes sense: religion’s job-to-be-done is much bigger than a country’s. A country cannot tell you what happens after death, just as a company can’t put the local thief in prison.


  1. There are exceptions to everything of course, but broadly that seems to be how it plays out.

Patriotism as the Messenger for Science

Neil deGrasse Tyson just appeared in a video that is a must watch. Take the 4 minutes and watch it:

He comes out swinging immediately:

“How did America rise up from a backwoods country to be one of the greatest nations the world has ever known?”

(Meanwhile the video shows pictures of George Washington, American flags, the Model T, and Neil Armstrong walking on the moon.)

“We pioneered industries. And all of this required the greatest innovations in science and technology in the world. And so science is a fundamental part of the country that we are.”

What he’s trying to do is show patriotic conservatives how that pro-America feeling1 goes right along with science:

“Guys, look at everything America has done with science. Science makes America great!”

This is a good technique because you cannot change people’s minds on big issues with mere data. When you tell someone that their view is wrong you are attacking their identity. The issue is much bigger than just the single thing being discussed.

(There’s even something called the “Backfire Effect”, where a person will end up believing their current POV more after hearing disconfirming evidence.2)

So when you’re trying to persuade someone you need to do more than show them data. You have to give them an out! You gotta show how the narrative they’ve told themselves about their life and their values can coexist with this new information.3

And that’s the message Tyson is going for with his opening:

“You want America to be great again? Look at all these things that made us great before, all accomplished with science.”

Other parts of the video are more critical of the “make America great again” crowd. But overall the video demonstrates a powerful messaging strategy that everyone who is worried about science should use:

Science is patriotic and American.

It is American to discover and test and research.  It is American to invent new products and industries.

A really cool idea IMO would be to show what discoveries and research led to what products.

E.g. what were the scientific papers that led to the iPhone?

Here’s the (I believe) original paper about multi-touch from Jeff Han at NYU’s Media Research Lab (PDF) and here’s his first public demonstration of multi touch, from a Ted talk.

There’s often going to be some “basic/fundamental research” that goes into new technology products, and seeing a concrete connection between the research and the final product would go a long way into convincing people of the value of science.

  1. Which, for the record, I also subscribe to!

  2. Read more about the Backfire Effect and how to counter it here (PDF).

  3. To be clear: we all tell ourselves narratives about our lives and values, so this technique should be used when you’re trying to persuade anyone of something significant.

Creating New Things

Making new stuff is hard because the thing you’re making sucks for most of the process.

By definition it’s incomplete and imperfect the entire time until it’s “done”.
Plowing through that gap is hard though, because the current thing you’re making sucks and you don’t always yet know how to make it good. 

Jordan Cooper (an entrepreneur and investor living in NYC) wrote a post about this process. The money quote:

It’s not easy to understand how just committing to talk about an idea with anyone who will listen is a totally reasonable first step to making that idea reality…for someone who hasn’t done it before, talking might not feel like progress, but the steps to reality are subtle and require faith.

It never occurred to me that merely talking about an idea could be considered progress. Small victories FTW. 

Damn You, Perfection: Part 2

I just read this post from a friend and filmmaker about perfection.

The only time you’re going to do something perfectly from the beginning is when the task is mechanical and clearly outlined by someone who has done this exact thing before.

It hit way too close to home.

I didn’t realize until recently (my wife started constantly pointing it out) that I tend not to do or finish things when I don’t think they will be done perfectly.

There’s a particular project I’m currently trying to ship ASAP that requires a lot of important details and things I really, really want to make sure I get right. I’m worried that coming up short might disappoint customers, and I’m worried about not knowing some of these details and being embarrassed in front of my customers.

(Hell, I’m afraid to even mention what this vague project is because I don’t want anyone to know about it until it’s successful. Heaven forbid I appear imperfect to others…)

But my wife keeps telling me “it’s fine, just do it. It will work!” I can hear her voice in my head as I type this.

Back in school I had one of the best accounting jobs a college kid could ask for, at a local tech company. I shared a cubicle with one of the hardest working and smartest people I’ve ever known. The guy could just get shit done while simultaneously maintaining the highest levels of perfection.

His reports were beautiful, professional, and sounded like there were written by some 45 year old career executive, not a young accounting intern.

I never came close to keeping up. We worked there together for almost 2 years and my constant feeling of inferiority notched my desire for perfection up about 1000 degrees.

This has not served me well.

My friend always knew he was headed to the corporate world. The world of professionalism, polish, and appearance. As for me, I didn’t last long in corporate America because I couldn’t stand it.

But in the wild west of entrepreneurship where I stand, perfectionism will literally kill your business. It serves no purpose and is a self-imposed death sentence.

Trying to write on this blog every weekday has been a small way of fighting perfectionism. The goal is to write for myself, so it doesn’t matter how good a post  is. If other people happen to read anything that’s just a nice bonus.

Nothing here to end with other than a personal reminder to ship earlier than expected, to not underestimate one’s self, and to realize that most things start off as an embarrassment to the creator.

Steve Ballmer’s Newest Thing

Steve Ballmer just publicly announced a new thing he’s funding: a public database that shows all government spending across federal, state, and local levels.

He likens the project as the “10-K” of government.

He did an interview with the NYT about it here. A good part:

“I love this one!” he said, showing me a slide of information about government employees. “Don’t look, don’t look!” He instructed me to cover my eyes from the number at the bottom of the page.

“How many people work for government in the United States?” he asked, with the excitement of a child showing off a new toy, before displaying the answer. “Almost 24 million. Would you have guessed that?”

Just go read the whole thing, then sign up to hear more from the project website,

Abraham Lincoln

I think one of the saddest individual tragedies in American history is the assasination of Abraham Lincoln.

After all the things Lincoln had gone through: 

  • A lifetime of political failures before becoming president,
  • Only to be elected to preside over the Civil War
  • Wading through multiple generals who missed war-ending opportunities before finally finding Grant
  • Running for reelection in 1864 while still fighting the war(!), against his own former General(!!) George McClellan
  • His wife mostly losing her mind
  • Losing a son
  • And on and on…

So after all that General Lee finally surrendered on April 9, 1865.

And Lincoln was killed only 6 days later.

They’re still cleaning up the parades celebrating your pinnacle achievement and you get killed. Ugh. 

I’m not sure what there is to take from this other than sadness but I’ll give it a shot:

Having and following your own personal principles makes life Worth It regardless of final outcomes.

He could “enjoy the journey” in the sense that he could be satisfied with his decisions while making them, instead of having to hang his hat and hope on some future event.

Paid Events as User Acquisition

I’m in Boise Idaho this weekend doing Questival with a few local friends.

Questival is an event put on by an outdoor clothing company called Cotopaxi. Here’s a video explaining what it’s all about:

It’s basically a 24-hour scavenger hunt, but instead of collecting things you’re doing things. Here are a few of the todo items from our event:

  • Eat a real worm, not a gummy.
  • Go to a restaurant serving food from a country you’ve never been to, and eat a dish you’ve never heard of. Be honest, really try something new and make it count.
  • Trade a piece of clothing with a stranger that is not participating in the Questival. FOR KEEPS!

There’s also lots of todos specific to the city.

By all outward appearances Questival is a huge success. They’re doing 50 events in the US this year.

The real genius though is that Questival serves as customer acquisition for Cotopaxi.

They get paid to acquire a super engaged customer, build a strong initial relationship, and have that customer share all the cool todos from Questival on social medai.

It’s pretty dang smart, and I’m surprised I don’t see other companies trying something similar.


Capitalism to the Rescue of American Health

Free trade could be about to save the health of Americans everywhere.

I see this trend via a few data points…

Whole Foods Closing Stores for the First Time since 2008

After 6 straight quarters of sales declines Whole Foods is shutting some of its stores and decreasing its plan to grow to 1,200 stores.

Why? Not because of lack of demand, but because of too much competition.

Other retailers have noticed the demand for healthier products and are shifting shelf space to accommodate them.

Companies like Bai

Bai’s original drink was a light juice-type beverage with only 5 calories and a single gram of sugar. They now also carry lightly carbonated drinks with & without caffeine, some sweet teas, and flavored water.

All their drinks come in at under 5 calories and they taste fantastic.

Bai’s “job to be done” is great taste without sacrificing on health. A big part of their success has been using a proprietary erythritol and steve leaf extract which doesn’t affect your glycemic index.1 They started from scratch in 2009 and were acquired at the end of 2016 by Dr. Pepper Snapple for $1.7 billion.2

Menus that Focus on Calories per Consumption Unit

By “consumption unit” I mean things like individual bags of chips: products meant to be eaten in a single go. 100% anecdotally I see more of these popping up.3 I’m seeing more air and less product in the same size bags.

This also includes restaurant menus with sections like “fish under 400 calories.” 

(To be clear, I don’t mean state mandated calorie counts for all food items on a menu)

It’s Become Lower Class to Eat Fast Food

To be clear: I mean class in the sense of culture, not income or wealth. (Please, please read this for the best piece on class I’ve ever read.)

Eating healthy could very well become an aspirational good. Imagine if people valued commoditized food the same way we value commoditized shoes and sportswear.

The rise in “fast casual” dining is IMO a direct effect of this.

It’s Easier for Markets to Influence Diet than Exercise

I don’t claim to know if weight gain is a symptom of a cause of bad health…

But I do know that it’s easier to lose weight if you focus on diet over exercise. And I think that’s for the better… it’s easier to get someone to buy and eat a healthy meal than it is to get them to go outside and run in the heat for 30 minutes.

Reasons to be Pessimistic

I am hopeful, but boy are there some big caveats here.

First, free trade gives people what they want, and human beings are built to want sweet, high-caloric food. So from day 0 we’re fighting against human nature. (Of course that’s always been the case, and we haven’t always been this unhealthy…)

Second, our general state of nutritional science, aka “do we know what food is good/bad for us and why” is astonishingly bad.

Every diet, whether it’s Keto, Atkins, Whole30, high protein, Paleo, or whatever… all seem to be their own type of religion:

  • They’re operating in their own worlds with their own sets of rules
  • They all have individual success stories they can point to as “evidence” for why their food rules are The Correct Health Rules
  • Their rules are usually mutually exclusive with the other diets
  • They seem to be oblivious that other diets with mutually exclusive rules also have their own success stories so they can point to people in their health tribe as evidence that their rules are The Correct Health Rules

Add to that the fact that the Food Pyramid can apparently change quite dramatically 4 and it feels really hard to be confident about very much related to nutritional science. The best I can come up with is what I call “the physics diet”: eat less energy than you use.

This 2nd part is particularly important because of part 1: capitalism gives us what we want, so we better make freaking sure that we want the right stuff. If our nutritional science is lackluster how can we know what to buy?

All that said I’m still optimistic. Free markets are generally underestimated… if people really, truly want to be healthy and we are correctly informed, the market will go through walls to make it happen.

Picturing the same power that brings 91,000 people out of poverty every single day fighting on behalf of our health is a wonder to imagine.

  1. Whether this is even a healthy thing to focus on is a fair question and covered below.

  2. I didn’t realize the acquisition had happened until doing research for this post. I’ve been drinking Bai products for a year or so and can’t recommend them enough if you want a slightly sweet drink without being super sugary or feeling like a soda. They were my bet to be the Coca Cola of the 21 century until I read about the acquisition. I’d have trouble turning down $1.7 billion, too.

  3. “Servings” is a dumb measurement IMO because it’s totally arbitrary.

  4. Why does it feel like no one things this is a big deal other than me?