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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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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