Jason Calacanis

Today’s guest is Jason Calacanis, a serial entrepreneur, angel investor, and author of Angel, a book about making investments and spotting trends. We talk about what the future holds for jobs, parenting, and education.

Jason’s 2 Cents

Kids value time the most. Love is spelled T-I-M-E in my mind. Leave your device off. Go on a hike. It’s not the number of hours, it’s how present you are. Kids are going to follow your lead. My daughter and I hike for two hours and then get lunch. I also do meditation with my daughter, which has been great for her focus issues.


The reason I wanted to have you on is because as an Angel investor you spot future trends
Anyone who is listening who is a father knows that this is the most important job title we have.

Let’s talk about the book.
* The book was my way of sharing how i went from rags to riches. But in this case from riches to mega riches.
* I had been a successful entrepreneur
* I’ve made mistakes, too, and what i have learned at the age of 42 is that people tend not to remember the mistakes, and tend to rally around your successes.
* Things right now have been a bit nasty in dialogue. I think podcasts are in renaissance right now partially because people want to have meaningful conversations.
* I’ve been ahead of the curve quite a few times, and being ahead puts you ahead of the crowd. In terms of Angel investing there are maybe a dozen people more successful than me, but none of them have chosen to write a book.
* I’ve hit six unicorns, which is what got me the opportunity to write this book for Harpercollins.
* When I was growing up I had no idea how wealth was created, and this is my way of sharing that.

How do the founders that read this book carry those principles into their company to see what’s coming?

  • It’s super easy for someone who is a founder to identify who angel investors are today.
  • Finding them isn’t the problem, the problem is understanding them and what they want.
  • Founders tend to bend the truth to impress investors. 2 or 3% of the companies i do due diligence on i find are lying about the state of their business.
  • If you’re an angel investor, the opportunity is investing in potential. The expectation is that things won’t be perfect.
  • As gen Xers, we were trained that wealth is created by a good job, frugality, and owning a home, paying it off, and investing in more homes.
  • My parents paid $45,000 for their brownstone in Brooklyn on blue collar jobs. Combined income was about 1x the cost of the home. If they put 10% towards the home they’d be done in ten years.
  • Now that brownstone is worth about 1 million. Blue collar combined income around $100,000. It would end up being 10x blue collar income. That way to make money is gone.
  • 30 million jobs in retail and driving are going to evaporate. So cashiers fight for a living wage, and then those companies replace cashiers with kiosks.
  • So now people won’t have to sit in a tollbooth, drive a truck, or make you a coffee–work hard jobs. So what are they going to do?
  • Our kids are going to live in a world that flips three times. Internet, AI, Biology, etc.
  • How do we prepare our kids for that?

What has to change to adapt to that future?

  • I believe the education system will not serve them well–reading, writing, arithmetic, socializing are all essential of course. I don’t think the school systems served us well. I see a lot of middle aged contemporaries of mine are being aged out in Silicon valley.
  • I have taken it upon myself to teach my 7 year old and 16 month old twins about business.
  • My daughter, I took her to my incubator and told her that she could either go to college or start a business.
  • If she wants to be an artist she’s privileged enough to have a dad who can underwrite that–I didn’t have that. My options were firefighter, cop, bartender, etc. I ended up in computers and this is where I am.
  • Right now my daughter is going to start an ice cream business with her $300 in savings. We’ve been doing market research, she’s going to learn cost of goods and unit economics, marketing, customer support. We’re going to go to a pop up store or farmers market. I don’t think anything she’s learning in school would allow for that kind of focus.

What are the trends in the schools that you’re seeing to help with these changes?

  • I see a lot of people focused on exactly the wrong thing, which is status and competition.
    People are obsessed with kids getting into colleges, ap classes, math achievement, etc.
  • They’re obsessed with their kids being in the schools of billion dollar founders’ kids.
  • Lots of keeping up with the joneses
  • There is a high suicide rate in Palo Alto because of high competition. For one of the most affluent places in the country to lead in suicide rates for children should make the parents reassess.
  • In my mind it’s the parents’ fault. Collectively/culturally.
  • I tell parents who are freaking out about where their kids will go to school, i tell them about my background. I went to public schools and did poorly in high school. I have more success than most of the people i meet from Harvard. Ivy league is not all that. The people who are happy have a sense of mastery, and a sense of joy that they get to participate in something purposeful that matters to them. We don’t need to live a Kardashian lifestyle. The Kardashians are not a happy family–that’s not what we need to be like. It’s a mixed message of what success is.
  • I want my daughters to feel like they can accomplish anything and not be distracted by all the crap.
  • We follow a reggio style education system. If the kids are interested in orcas, teach math or reading by using examples of orcas. It makes them excited about going deep.
  • So I sit down as a mentor with some of my employees and ask them what success looks like for them. I don’t think enough people have thought about what success looks like for them.

How did you and your wife arrive at this? There’s a trend of lack of focus, people aren’t slowing down and asking themselves the important questions.

  • If you look at ADD and ADHD and aspergers. This inbound existence…it’s having an impact on people’s brains.
  • The idea of dying a violent death has gone down significantly, the idea of living in abject poverty has gone down, so much so that the things that will kill us are self inflicted and highly avoidable–like suicide. In the developing world where there are fewer regulations, more of these accidental deaths happen like commercial plane crashes. In Germany a suicidal pilot runs a plane into a mountain. It’s not because of the actual act of flying. It’s a long way of saying that our kids are going to live in a world where starving to death won’t be the cause of death, overeating will be the cause of death.
  • I was talking to an educational psychologist about our daughter who doesn’t like to sit still in the classroom, and she mentioned medication. How will she function as an adult in the world otherwise. We thought that was crazy, that a kid who runs around at age 7 years old is broken and needs to be medicated to sit down at school for 6 hours.
  • Workplaces are trending against this sit still for 8 hours thing. People are working in bust style fashions with intermittent physical activity.
  • We should rethink the classroom if the kids have this much energy. We need to accommodate the kids and their needs.

I am with you, that the schools aren’t changing. Who is tackling this?

  • I think the teacher to student ratio needs to be no more than 10 to 1. I would love if we would raise the tax rate on the country’s top earners, and then quadruple the number of teachers there are, and double the number of hours in school.
  • School should be available 7 days a week, 7am to 7pm. If you need to work on a saturday, drop your kids off on a saturday where they’ll do project based learning.
  • It would not cost that much for us to have schools available like this. Anyone who says it would cost too much just doesn’t understand the numbers.
  • The tax breaks we offer are criminal. I benefit from them, and they’re terrible. If you went to the top million earning americans and told them we were going to charge 4% more on your taxes, and we’ll have 7 days a week schooling available for kids, you would have 99% say yes, and 1% say “i earned mine!”

I would agree that our investments are so lopsided, what other things should change about the schools?

  • I think if you look at youtube, Lynda, conacadamy, treehouse, etc. corsera, edex, we’re living in a society where you can afford to acquire any skill online.
  • If we have all the information line to learn these skills, then why aren’t people doing it? I’ve heard that people don’t have enough time, that they don’t have it available, or they don’t have the precursor education. There is always time, and $25 a month is not a lot. It’s not an insurmountable hurdle. And often it’s free.
    People ask me all the time what they should be learning, and i say look at linkedin and see what people are looking for.
  • People used to be proud of working hard and acquiring skills. Everyone wants the kim kardashian private jet, but they’re not willing to put the work in.
  • When I was growing up this information wasn’t available for free, you had to go to college for it. Knowledge is so cheap and available, yet people don’t want to read books or learn skills.
  • So we’re at this crazy moment in time where one group of people are capitulating and feel helpless, and the other feels empowered.

Why do you think that is? What role do the parents have in that?

  • I’ve heard role models is one piece, so if you don’t see someone who looks like you in a role, then you might not even consider something as a possibility. Race, gender, etc.
  • I also think we live in a victim society where people feel that the world is against them. We’ve made it easier for the rich to get richer, and harder for poor and middle class people to move up. We’ve rigged the system at the same time that low income jobs will disappear at a high velocity. It’s very scary.
  • But there are solutions, but people don’t want to hear the solutions to society’s problems. There’s a burn it down mentality.

It feels a bit hopeless

  • It feels bad because we always expect things to get better, and for a lot of people it’s not getting better.
  • We are addicted to our social media, which feeds us terrible news and great news all at once…using an algorithm that is designed to mess with our emotions on a rage, sadness, and joy cycle. People who design these algorithms need to take a look in the mirror and think about what they’re doing. Fake news plays a role in this, too, which has serious consequences.

What’s one piece of advice that you would give to a new dad?

  • Kids value time the most. Love is spelled T-I-M-E in my mind. Leave your device off. Go on a hike. It’s not the number of hours, it’s how present you are. Kids are going to follow your lead. My daughter and I hike for two hours and then get lunch. I also do meditation with my daughter, which has been great for her focus issues.



Schools and Organizations


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Challenge Everything with Alfie Kohn

World Renowned author, speaker and thought leader Alfie Kohn is on the podcast. Author of such thought provoking (dare I say controversial) books as….

If you thought that telling your children “good job!” was a good thing, or if you ever offered reward to your kids… then you’ll enjoy this episode. Be ready to challenge you ideas about parenting and how you parent.

Alfie’s website
Alfie on Twitter

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11 Kids, Growth, and Revenue with Author/Entrepreneur Aaron Ross

aaron ross

Aaron Ross is a hustler, although he might not like me to use such a loaded term to describe him. He is a father of 11 children, he is an author, he is a business man and speaker. He HAS to hustle to do all this. He gives a very honest commentary on what it takes to manage all of this simultaneously. It is not easy but it is worth it. Listen up, guys like Aaron don’t come along everyday.

Where to find Aaron online
His business – Predictable Revenue
His book From Impossible to Inevitible
His Instagram (for all his familia shenanigans)

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“Everything is out of wack” with Hiten Shah

hiten shah

Hiten Shah joins the podcast. He needs no introduction for those in the startup space. He has built the following companies and is a father of two young children. He has started three SaaS companies, Crazy Egg and KISSmetrics and Quick Sprout. One is venture capital backed & the others are self-funded. Find Hiten at the links below….

Hiten on Twitter
Hiten’s startup podcast with Steli Efti

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Running Lean with Ash Maurya


What does Lean have to do with family? Today the thought leader on lean, Ash Maurya, talks about just that. One of my favorite quotes during the interview….

You can’t negotiate for time with a crying baby. I needed to be a lot more efficient with my time. Now I carve out my day systematically.


What do you tell people you do?

I tend to give people a high level answer, and if people ask a question I’ll go in deeper. I say I’m an author, then say I write business books, and on and on.

I’ve recently read your books and bought into the principles, could you talk about writing the book?
  • Before I was an author I called myself an entrepreneur. This was never in the plan.
  • This started by being frustrated with my own processes. We prematurely fall in love with our solution rather than the problem.
  • I didn’t start by writing a book, I started with a blog. It was good timing to start joining the Lean conversation.
  • So I used to be more of a tech founder, and now what I’m doing is I work with entrepreneurs, I speak, I write books, and build software for entrepreneurs.
How have you helped evangelize this and seen the light bulb go on?
  • I began this to get clarity for myself, but began to realize people were making these mindshift mistakes.
  • As I began my research I discovered that there were people all over the world running into the same types of problems.
  • So in my new company I make sure to fall in love with the customer problem. We’re not in the book business or consulting business or software business. We’re trying to build a better entrepreneur.
Where’s the overlap with how you’ve approached parenting?
  • People ask how I balance kids and startups. I dedicated the first book, Running Lean, to my kids because I learned from them the true value of time.
  • You can’t negotiate for time with a crying baby. I needed to be a lot more efficient with my time. Now I carve out my day systematically.
  • I like to spend time early in the day getting an accomplishment done so that I can feel good the rest of the day and live a more productive life.
Would you say now that you’re out of the infant stage, how has that affected your parenting?
  • I’ve grown up with Indian parents, they tend to be heavy on the education side and STEM. Very rigorous. But with the new world you can go online and pick any skill and get good at it.
  • I learned this about myself. Most of my skills have been self taught. School teaches us how to learn.
  • We put our kids in a Montessori school. It’s kids essentially educating themselves. There’s a guide who helps them make sure they get exposure to everything.
  • We try to do that at home too. We don’t plan things for them, they’re able to come up with things for themselves to do.
  • We try to create that space.
How early did they start Montessori?
  • When they were three and two and a half.
With leaving slack time, there’s a direct overlap between how we work, is that what drove you to montessori?
  • In my early years in Nigeria I was going to a Montessori-esk school.
  • Maria Montessori developed this by studying how kids work. Kids being a smaller version of the adult mind, and with different stages of development.
  • Kids do projects and reports together at a younger age when they’re developing social skills.
  • Soft skills are very important as you get older.
  • In this education system we find out that there’s not just one right answer, which is what we know as entrepreneurs too.
  • As long as we teach them how to learn, when they ask us questions we try to make it more socratic.
  • When I work with startups I tell them my work is more behavioral psychology.
What do you hope for for the future?
  • There’s another great book. Strengthsfinder. This unique value proposition applies to individuals, too. So my tend likes math more, and my daughter prefers reading. It’s guiding them and helping them amplify their strengths (while still having enough skill in the other areas).
What’s your two cents you’d give to a new father?

It’s taking it one day at a time. There’s nothing you can do to prepare. It’s life changing in a positive way. The first few months aren’t as interesting, it’s a lot of work, and then once they start to interact with you those are very exciting times. Every age is a great age.
You can learn so much from kids, even about yourself.



Running Lean Book
Scaling Lean book
Ash homepage

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Feeling Like Machines Living Together?

Credit: Shutterstock

There is a point that I arrive at with my wife that I hate and it’s routine. Not the good kind of routine where you are building positive habits…

It’s the time when I feel like we are going through life helping each other simply get done what we need to get done. When we feel like we are just co-workers at a factory and putting out fires.

And oh are there fires when you got three kiddos under 5 in a house.
(But you already know that)

The thing about it is, I don’t see it coming until BOOM! It’s happening. I just realize that I feel like I have not talked with my wife at all on a deep level. I have not really talked with my kids on a deep level either. I am just being. I am just working.

And fatherhood takes serious work!

I am sure that you have been there. If you haven’t then either you’re not human or you have some super perfect marriage (which means you’re not human). When it start to happen I try to figure out how and why we got to the place that we did.

Was it that fight we had that was not really resolved?
Was it the finance discussion about some purchases I made that were not in the budget?
Was is the lack of sex we have been having?

Yes yes and yes. But that’s not the core of the issue. The core of the issue and the key that always fixes this funk. The secret “hack” if you will?
Talking to my wife is the number on thing I can do to make this not happen.

Does it correct itself overnight? No
Does it make our marriage perfect? No
Does it make the kids behave like angels? No

What is does is repair the relationship. We are not machines and we need more than text messages back and forth. We need more than to-do lists that we are working together to check off. We need someone that really knows us and supports us.

My biggest weakness is not sharing enough with my spouse and the biggest area that I fail to share openly with her is with my work life. When I am contemplating a decision or had a bad day or can’t get something out of my head, I internalize it. I don’t share it. Why? Well the list is pretty long but a few reasons that come to mind are…

  • She won’t understand.
  • She doesn’t care.
  • I have to take too long to setup the context of the issue.
  • I don’t want to “bring my work home”.
  • I don’t want to think about it myself.

These are stupid excuses. What I need to do is share with her. My work /is/ my life. Is it my entire life? No. But to refrain from sharing it with her is to hold back on what I am going through what I am excited about, what I am worried about. It’s the personal side, the relationship. The thing is, she craves it! She wants to hear about everything, all the things that are going through my head.

Yes, it is hard. It takes practice and intentionality. But, it’s worth it.
Best of all it’s free! Try it today!

I’ve found the most success when I come home from work. Quick 3 step guide.
1. Turn off phone. Like fully off.
2. Sit on couch with my wife. Ignore kids unless someone is on fire.
3. Talk.

Not much more to that other than to make it a habit. I fail, we all fail, but getting back on the horse is the only way to a chance at success.

If you found this useful let me know in the comments, or share it with someone that would find it valuable. We’re all in this together.

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Reuben Gamez of BidSketch

Ruben Gamez is the founder of online proposal software BidSketch. We explore his work habits since starting his own business and “the resistance” which is a concept introduced by Steve Pressfield in his book The War of Art.


Ruben’s 2 Cents…

Parenthood is like practice and every opportunity with your children is an opportunity to practice and get better


Resources mentioned


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Meaningfulness with Ben Toalson, Father of 6

Ben Toalson joins the podcast. If he sounds like a legit podcaster, it is because he is…he is on the Seanwes podcast as well as a podcast on parenting that he does with his wife.

A designer by trade he shares the journey that took him to full time design freelancing and tons of nuggets along the way.

ben toalson family

Ben’s 2 Cents…

The piece a lot of men are still neglecting are themselves and the other areas of their life suffer because of it.


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The Tinder for Parents, Soam Lall of Kinnecting

Soam Lall, the founder of Kinnecting  the app that can be summed up as the Tinder for parents, here is the story….

When a father was left to fend for himself with his 15 mo. old daughter for nearly a week, he realized he was at a loss. He didn’t have a network of parents, let alone parents with kids of similar age near him. Random encounters at a playground. A passing nod on a stroll. There were parents everywhere, but they were not accessible.

There had to be a way to help parents meet each other. If popular dating apps were using algorithms for matching singles,  why couldn’t parents use the same logic for being matched with other parents for playdates, advice and recommendations? Take a parent’s location, their mutual friends, interests, children’s age and gender….

Less than a year later, Kinnecting was born.

soam lall

show notes

Soam’s Medium post about founding Kinnecting


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