The Unspoken side of Fatherhood, Jason Fried of Basecamp


Jason Fried the founder of Basecamp and NYT Best Selling author of Rework and Remote talks about freaking out when he became a father and why it should not be taboo.

As a well known figure and thought leader in the business and tech universes, and most importantly as a guy that always seems cool and collected, it is fun to hear his humble take on parenting. He admittedly freaked out and was nervous for the first weeks and recalls learning a side of himself that he didn’t even know (in a good way).

Jason is adamant about telling new fathers that the first weeks will “punch you in the face” and you may not connect with your new child immediately, thats OK, it’s normal. It takes some time, so don’t feel like you have to fake it. Hearing him preach this advice hit home for me, as I assume it will for most new fathers. It is important to realize that silence in these situations is detrimental. Speak up and share the things you learn, we are all in this together. 

Now for the interview with Jason…

Jason’s 2 Cents…

The first few months suck, the first few months are incredibly hard and they will knock you in your face basically. Then 4 months in your son/daughter will smile and little bit and it will change everything

Show Notes (time stamps approximate)

1:30 a good manager was the foundation of his working career

3:00 the first software product he sold was a program to organize his music collection

4:30 if you’re hiring someone then you should automatically trust them, not assume that they are going to steal from you. If you’re doubting them then you should not be hiring them.

6:00 started his business small and grew very slowly,  the momentum

6:45 growing quickly leads to cutting corners

7:00 making friends analogous to hiring, you don’t take on too many close friends

8:00 grow like a tree, don’t let your ego get the best of you

10:15 growth being fueled by ego is not a new phenomenon, instead ask yourself “why”

13:00 being there for your children early on is huge, they change so much in the early months, exciting to see his son connect words

14:30 being flexible to new parents is baked into how they work at Basecamp, working remotely and flexible with work timing

18:00 “Punished by Rewards” book was recommended to him by DHH

19:00 learning to hold himself back from being overly cautious was a interesting adjustment for him

22:00 the similarities between hiring adults not micro-managing and not being a helicopter parent

23:30 it’s fun to discover more about yourself after becoming a parent

24:00 you learn more about yourself and it is impossible to simulate being a parent. Discovering a part of yourself that you never knew at all.

25:00 a tidbit of knowledge heard when he got married was   “life begins at marriage” and the same he found to be true when he became a father

27:00 the first few months suck and will knock you on your face, and you might not even feel anything. It’s ok. Don’t freak out.

The first few months are incredibly hard and they will knock you on your face and a couple months later your child will smile at you and it will change everything. You might not feel anything. It is hard to connect. It’s ok, don’t freak out.


It’s the greatest thing in the world but it sucks for a little while, don’t freak out.

3 weeks in I didn’t know what I was doing and I was nervous.

You should absolutely do it. It is ultimately the best things ever but it sucks for a while.

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Flow with Anders from Time Block

Anders Thue Pedersen is the founder of TimeBlock a web app that focuses on getting teams into the state of Flow, which many people might call “in the zone”,  the process of breaking down work into chunks and focusing on doing one thing at a time. A powerful concept that applies at work and with your family.


Anders’ 2 Cents…

Getting in a state of “flow” or cognitive deep work is a skill that you cannot learn but is a very valuable skill that will put you in the top 1% of whatever you are doing

Resources Mentioned

  • Flow (book) Mihaly C.

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Veteran Entrepreneur Tom Rossi

Tom Rossi a serial software entrepreneur joins the podcast. His resume includes…

He shares true words of wisdom from his time in the trenches.

tom rossi

Tom’s 2 Cents…

entrepreneurs talk about their business like it is their child but really it is more like a wild stallion and it will run away with your life and it will take everything you give it

show notes 

resources mentioned


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Gratefulness and Embracing Your Weird with Pat Flynn

Pat Flynn from Smart Passive Income is on the show. Pat not only is a genius at online business, it turns out he is a pretty swell father. He was working as an architect when in 2008 he got laid off and had to figure out how to make ends meet. What started as selling a guide for passing the LEED exam for architects turned into an online empire bringing in over $150,000 per month. His story is pretty unreal but it is encouraging to hear the very practical things that he does with his children and how he admits that he is not perfect and he fails as a father but he is always looking to get better.

pat flynn 2centdad


Show notes (time stamps approximate)

6 year old boy, 3 year old daughter.

8:00 It was super hard in the beginning and he was always working, he had quite a few heated conversations with his wife over his tendency to be thinking about the business non-stop

9:00 Created boundaries for his business so that he could be mentally present with either his family or his business

9:45 Physical boundaries are important to tell himself what the space is for, an office for working. It is a continual struggle even with the boundaries.

11:00 It is impossible for him to work when the kids are around and wanting his attention so he didn’t even try and do it, he set boundaries of space or time (working when the kids are asleep)

11:15 mental switching when he gets interrupted in his work is huge so intentional work time is a necessity

15:00  very intentionally works with his son on how to deal with failure through asking him questions constantly. He want to teach  how to deal with things and figure them out on

16:00 Complaining and getting yourself down does NOTHING and he is trying to point his children toward action to solve the problem and not stay in a state of complaining

16:40 Gamify with his kids; complaint jar that his kids have to put money in if they complain but get money out if they seek a solution prior to a complaint. Him and is wife also have to play in the game.

5 minute journals

the miracle morning

19:10 Journaling is the most underutilized  things that we can all do

19:30 everyday write down 3 things you’re grateful for, 3 things you want to accomplish that day (what would make today awesome), 3 things that were great that happened that day, 1 thing you could do better

20:45 biggest lessons from his parents was that hard work pays off, serving others, patience

22:00 negative from his parent: focusing on the failure obsessively to strive for perfection all the time

23:10 “embrace your weird” is a mantra he teaches his audience as well as his son, what makes your weird makes you who you are

24:30 consistently talking wisdom into your kids is essential

26:00 His kids attend a STEM school

28:30 “Smart Money Smart Kids” by Dave Ramsey was a great parenting resource for him.

29:30 guidance and a diverse opinion is good but ultimately is comes from experience and you need to figure it out

30:00 stays up on what his kids are into, for example he started playing Minecraft because his son got into it so he could talk with him about it


Embrace your weird

Where you find your vibe you find your tribe

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4 Lessons Learned Interviewing Entrepreneur Fathers

So often we feel alone as new fathers and can not help but wonder that we are the only ones that are feeling the way we are or struggling in our new role. I sure did. I felt a range of emotions when I first became a father and one of the biggest was that I was unique in my struggle. What were other fathers doing to be intentional in their role, especially those that were starting businesses or pursuing a life of purpose?

This curiosity was the origin of the 2centdad podcast. I began interviewing fathers that are pursuing a life beyond the status quo; they are running companies, traveling the world, or building tribes. Why not hear it from the horse’s mouth! From those interviews I have come away with a few insights that I found are challenging but applicable.

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Y Combinator, Obama, and Layering on Love with Nate Kontny

Nate Kontny

Nate Kontny has been through Y Combinator twice, worked for the Obama re-election campaign in 2012 and now runs two companies, Draft which is a tool that offers version control and collaboration for writers and the CRM Highrise.

Links/concepts from the episode

1000 true fans

Brain Rules book

just talking to your infant/toddler with little care for what they are retaining

Thirty Million words book

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Triplets, DNS, and France with Anthony Eden


Anthony Eden is on the podcast today. He has been running DNSimple since 2010, which helps entrepreneurs with Domain Name Services. As a father of 15yr old triplets (and a 7yr old) he’s been forced to become efficient at managing his business and time with his family. He talks about raising a family while doing extensive travel as well as the practice of having his kids to do internships at local companies to broaden their exposure to work and careers. A native of Florida, he currently lives in France with his family.

show notes (time stamps are approximate)

3:10 motivation for starting his company was coming off a failed startup, knowing he could do a better job and build a better product

4:50 worked for Living Social while also building DNSimple, was always a remote worker in all this which allowed him to work on his schedule and spend time with his family when needed. Traveling is the biggest down-side of working remote.

8:00 having his wife work in DNSimple has been a long term thing but making it “official” has been honoring to her for the years she had put in

9:55 his kids have a pretty strong work ethic which he attributes to his wife’s upbringing in a military family being heavily scheduled. Having triplets also forced them to be more organized in order to even survive.

11:20 the super growth VC funded startup is “a story” being told but not the only story… there are businesses that are started and run all the time at a sustainable pace. Having a family is actually a great way to force you to think about building a business in a smart way that is not wasteful.

15:00 building a sustainable strong business and having a family has been going on for years, there is no reason you have to build a unicorn startup

17:00 he prioritizes traveling with his children but not to the tourist spots but to see a lot and experience different places and people

18:20 long ago cut out TV at his house

18:40 plays podcasts for his kids in the car while they drive

19:00 kids each had to do an internship at a company for a week

21:00 things he wants to impart on his kids: teaching them how to manage money. Also that they don’t need to follow anyone’s script for their life.

23:00 regret: wish he would have been in Europe when his kids were younger and maybe in the US later when they were older.

25:00 last word: be there when your kids need you, you can never get more time

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Fatherhood Advice from 5x Founder David Cancel

david cancel family

David Cancel is a 5X founder, former CPO at Hubspot and currently the CEO of Drift. Wonder how he does it while having two young children? Well it’s not balance thats for sure, he is not a believer in balance. Oh yeah, he wakes up at 5:30am, rarely travels and brings his family into his office on occasion. David brings some ultra practical advice on founding companies and being an intentional father.

You can also find David dropping knowledge on his business podcast over at SeekingWisdom

show notes (time stamps are approximate)

4yr old son

10yr old daughter

married for each of all 5 of the startups, daughter part of 3 of the startups

4:00 David doesn’t believe in balance and most people that strive for balance try to achieve it each day which is impossible because life is a constant ebb and flow. Balance is more on a macro scale.

5:40 Schedules are unpredictable and nights especially, so he focuses his energy on being present and spending time with his kids in the morning. He does not travel much because he would miss the morning. Has breakfast with them and drives them to school. He’s intentionally offline during this time.

7:00 He gets up by 5:30am

7:30 His family is super involved in many ways but he does try and shield them from the ups and downs of a startup. He has his team over for dinner and brings his family to the office.

8:50 the first thing he asks a potential hire that has a spouse what their spouse thinks of the job and the company

9:30 he would label himself as more conservative and its his wife that encourages him to “go for it” in many situations

10:20 both parents immigrated to the US and would attribute his work ethic to his upbringing amongst his parents being business owners, they give him the “ultimate perspective”

11:40 all you can do is try and do a little bit better with your kids then your parents did with you. Once you have children you realize that its 99% nature and 1% nurture and its about fostering their personality.

13:20 the most important thing they do with their kids is promoting the ideal of the individual, letting them learn from their mistakes and not step in to help them too much. Let them learn at their own pace.

14:45 biggest failure with his kids is patience, constantly wanting to step in and teach his kids in the way he learns. Attributed to his personality of a founder, he’s more prone to want to step in and take charge.

15:30 understanding personality if huge with children as well as in a team, relating to different personality types the way they want to be related to and not the way we want to

17:30 advice to the first time father – talk about the founding of the company and if its the right decision. Also try and test new things and

19:45 spend time with other startup dads and trade ideas. Be intentional!

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Marc Hemeon Gets Extremely Honest on Startups & Family


Legendary designer Marc Hemeon joins us and offers a very honest and personal look into his experience of attempting to balance startups and family. Marc has been in the startup/tech game since the 90’s including stints at YouTube, Google’s self driving car project, and most recently founding Design Inc. As a father of 3 and having a marriage of 17 years, he’s seen the ups and downs and offers some very very practical advice. It was refreshing to hear him speak so bluntly on the work that it takes to guard your family and your marriage while doing work you care about.

Last word of advice

Drink water, I think genuinely most people are just dehydrated….😂

Show notes (time stamps approximate)

3:20 working from your heart, Painting

4:50 most people just want to be a boss, not work from their heart

6:10 “working from your heart puts you in opposition to your partner”

6:40 “the only reasons people get divorced is because of sex or money”

7:50 Sometimes i wish i had pushed the brakes…

8:25 Big fans of date night

8:50 Margret stewart

10:20 Tactic: Sending a note to important people that he is working with telling them to respect his schedule and work with him as he works to make time for his family.

11:25 People quit jobs because of resentment and resentment builds up when people don’t meet your expectations. (Marisa Myer quote)

12:00 People surprised by Marc when he sets boundaries to spend time with is family as if they didn’t know that it was possible.

13:10 “people with families need different working styles, they just do” because sometimes you need to tend to things like surgery for your kids

14:00 “you gotta be ok with potentially losing your job”

15:30 being intimate with my wife on FaceTime is not the same as being intimate in real time (on traveling for work and being away from family)

16:25 there is some guy listening to this saying “Hemeon is an idiot” I got this, I got Gary Vaynerchuk style energy…good for you man, I don’t want to fight you but just take your spouse’s needs and put them in your heart.

17:30 Marc on Elon Musk and doing things that are advancing humanity. If you’re Elon Musk you gotta do the Elon Musk work. And there are not many people like that.

20:20 calculating the years left while his kids are at home in terms of summers and winters and maximizing the time they have left with the children at home.

21:27 its about quantity time with his children, talking about “whatever” and enjoying the time together

21:45 grew up in Vienna VA oldest of 7 kids. Dad’s own gas stations and mom is an artist. Both parents working hard when he was a kid left him on his own in many ways.

23:15 growing up back East without an allowance and without entitlement led him to a greater appreciation for hard work and things he has.

23:50 the reason I work hard is perhaps to fill the void of the lack of relationship I had with my father

24:15 men in general need to kill their fathers, figuratively. To figure out what it means to define yourself as an individual and severing that dependency or that need for approval.

25:00 there is the thing inside of me that wants to create something that I didn’t have when I was a kid, a closer family then I had growing up.

25:45 its not terrible to be driven by your ego for a while but its just not going to make you happy

26:30 on making good money and not being happy

27:45 for a lot of folks maybe its not a must to have a family, thats ok

28:00 happiness is earned. its not just walking off into the sunset, you gotta sacrifice for your spouse and earn it

29:10 there is no separation between work and life, there is just not. My kids can look up all the stuff that I have done, talks I have given and what I worked on. What kids of legacy do I want to leave?

30:20 to the newly married dude or the guy about to marry his daughter: do you have life insurance? what is your relationship with money? how did your parents use it? What is your plan for the money? Have you talked about the dirt? What are your values? Example, do you want kids? Are you religious? You need to have a shared value system?

32:30having a designated time to spend together and time to go on a date night.

33:00 we spent a lot of time trying to teach each other. Have since learned “Staying on our side of the street” not telling the other “how to drive”.

33:30 planning is simple but huge, blocking out time

34:30 connecting with other guys that are husbands and fathers to talk about life and things. You need a forum to get stuff out and have conversations not inside your family.

35:50 being really really open with what you need

36:20 busyness is a defense mechanism to avoid talking

36:40 figuring out what you need everyday from your spouse and ask them for it and be willing to meet your spouse’s daily needs

40:00 kids care less about the things that you give them and more about the experiences that you create with them

40:20 we prioritize each other over our kids, putting each other first

40:40 its super easy to get divorced. People say “oh we fell out of love” yeah you probably did but go on back in there an get back in love

41:20 you tend to attract people with the same size void that you have

42:00 you become the people you hang out with the most often

42:50 last closing statement ….

Last piece of advice is “drink water”. Most people are honestly just dehydrated.

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Stoicism, Screen Time, and Reward Cycles with David Heinemeier Hansson (DHH) [Podcast]


David Heinemeier Hansson (DHH) joins the podcast. For many people, DHH needs no introduction…but just in case, here is a little background on how David keeps himself busy (apart from fatherhood):

As expected, David brings his energy and passion to the conversation about parenting—a talk which is both opinionated and thought provoking. He shares many of his views, from the “screen time” of his 4-year-old, to which practices promote intrinsic motivation, and why classic reward cycles are completely bogus. Here is a list of the resources that David mentions in the episode:

The systemic risks to “finding the best for my kid”. If the “best” is an Ivy League education or high paying job then you are already lost. Happiness is not correlated to the factors of success that society often put the most weight on.

Show notes (time stamps are approximate)

Magic the gathering card game was the first thing that he sold/traded. Gave him the early understanding of sales and making deals. Spent summers as a young boy trading/selling cards.

3:27 got into selling pirated software. Ran an Elite Bulletin Board forum  (13-15 years old). Made his own money prior to “commerce”, delivered newspapers at age 10. Learned salesmanship in trading.

7:00 Everyone should work jobs they hate to give them memories and experiences.

7:57 Work for other people in the line of business you want and have a bad experience, it teaches you what NOT to do.

10:22 Empathy for those that you are managing/working with is key to learning from experiences and improving on things when you call the shots.

11:50 “If I can see all the things that are wrong here, then I can do a better job here.” DHH on management.

13:47 In the life of most entrepreneurs there is something in their formative experiences that “pisses them off”. They think, I can do this better.

15:00 My dad was wheeling and dealing and fixing electronics which taught me the way NOT to do it and what I would want to change in what I did. “My mom was an incredible pep talk coach” Source of his confidence. Love from his parents were not contingent on results.

20:37 Growing up we were poor by most respects.

23:20 How is he NOT spoiling his children? Artificial scarcity as a practice is false. Having everything does not make a happy kid or happy adult either. What is important is to instill a sense of what really matters.

25:20 Setting things up in a reward cycle is a really bad mechanic. Teaching people self reliance does not happen via carrot reward cycles that kick in when they do things they don’t want to do.

26:30 I’m not going to limit him [my son] by any means. How does it matter if he wants to

27:20 Limiting screen time is bogus. Limiting scarcity only promotes demand. Let him play with the iPad and let him find out what his natural limits is.

29:50 Study on cocaine addiction and rats and who it relates to screen time and the variety of options being a solution.

31:20 Disclaimer: “All of this is sample size of 2, my upbringing and with my son.”

32:19 Put all the activities in front of my son and let him figure out what he gravitates to and him discover his own limits.

33:45 Nature vs nurture in his son

36:00 wife and him on the same page with parenting

37:00 What has influenced your parenting style?

37:19 Alfie Cohen

Myth of the Spoiled Child (link)

Punished by Rewards book (link)

Flow book by Mihaly C. (link)

Intrinsic motivators are key. The western education system does its best to rid kids of the intrinsic motivation. You need to start early to protect your child’s psyche early on. You are against forces much stronger than yourself.

41:15 Elite institutions are not the path to success.

42:30 Kids age four interviewing for preschools is completely stupid. I want my son to run around and play at preschool and not have pressure to think about what college he is getting into.

47:00 Start of his general overview on parenting philosophy…

48:00 last words of advice.

The systemic risks to “finding the best for my kid”. If the “best” is an Ivy League education or high paying job then you are already lost. Happiness is not correlated to the factors of success that society often put the most weight on.

50:40 Studies on suicide rates among kids that are pushed to the high standards of performance by their parents.

52:00 When your direction in life is driven by fear they you have already shut off many important parts of your mind. Get rid of the fear!

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