Bootstrapped Giants

Raising Kind Winners

Published 4 months ago • 10 min read

This is a more personal email than usual. If you only want business, get My Annual Planning Guide here.

I was blessed this week with my 3rd child: Mila Kaur Pujji. We have an 8 year old, 6 year old and now a newborn. You might be wondering why I'm telling you about kids when you subscribed to a business newsletter. It's because I don’t subscribe to “family first” or “family second” or “business second.” At any given moment, I am an entrepreneur, dad, husband and all of those things. I think compartmentalizing those is inauthentic and ineffective. And I’ve found the more I embrace my “whole-ness,” the better I show up in ALL places.

To set the table: Parenting has been the most positive surprise of my life. I have a much younger brother so had a taste of the joy of "raising" a kid growing up. I was looking forward to kids. But even then, it blew me away as something so energizing, so grounding, and so gratifying. The older two have been a blast. And the night Mila was born, she was crying while I was wiping meconium (weird black newborn poop) in a dark room. In my mind, all I could do was look forward to all the milestones I knew were coming.

Parenting is a joy because I handled the basics: sleep, alignment with spouse, and childcare. I went hard on each of those, and it paid off with quality time with my kids and meaningful time to work.

When it comes to raising kids, there's no right answer, only endless questions. First, what is the goal? Is it to raise SUCCESSFUL kids? Or is it to raise HAPPY kids? Or is it to raise GREAT PEOPLE? Should you "helicopter" or "tiger" or "gentle" parent?! So many choices. What do you do?

I spent time as a management consultant. Have constantly figured out resourceful answers as an entrepreneur. And I am someone obsessed with intentional inner work. So I have spent A TON of time thinking about and experimenting with these questions.

Here's what I think:

Know thyself. One of my favorite paradigms in parenting is "conscious" parenting. The core premise is: your kids are here to raise you as much as you are here to raise them. That doesn't mean they are in charge btw, it just means you can learn a lot about yourself from how your kids impact you. What bothers you? What beliefs do you have? Why? Reflecting on what pisses me off, where I nudge my kids, where I disagree with my spouse is a source of immense learning for me in my own growth journey.

Example: when my kids are loud, it bothers my wife like crazy. To me, it feels like ENERGY, I love it. But when my kids try to quit/are lazy, ooo it bothers me; my wife sort of shrugs and says they have a lot on their plate. Knowing ourselves and our areas of growth help us “check ourselves” as parents.

The better you know yourself, the more TRUE you can be to yourself. I like to say “there’s no right way to entrepreneur, you have to do what’s right for you.” Parenting is exactly the same. You can only parent in a way that's true to you. If you want your kids to be a huge success, then parent them that way. If you want empathy to be a priority, focus on that. THERE IS NO RIGHT WAY TO PARENT, only your way.

So what are some of MY WAYS?

First off, I think "successful" vs "happy" is a total false dichotomy. I think tiger and gentle are false dichotomies also. I want my kids to be happy AND successful AND self-aware AND good people AND growth mindset type people. The interesting questions are where is the overlap in all these places? And how do you support your kids in finding those overlaps?

Notice I said "support your kids." This is a core belief of mine: I am not responsible for my kids' happiness, success and I do not "control" the outcome here. They are responsible for their lives (even at a young age), they are responsible for their feelings, their choices, etc. I, of course, view myself as a critical support system available to them. To take it further, I view myself as a "steward" for these incredible souls. The Universe/God gave me these individuals for ~18 years and this amazing job to help guide them towards THEIR purpose/genius. Not to force them into a direction I believe or saddle them with my baggage. They don’t need to be entrepreneurs or growth marketers, I want them to find their x-factor: what gives them energy and where they excel! So a lot of my job is to help them identify their genius and double down on it while getting out of the way. I want them to be motivated by helping people and being their best selves, not by fear or extrinsic goals (which I think is more typical.)

My core belief is that you can raise BOTH successful AND happy kids. I think you take the best of "both" systems and combine them. You can be both "demanding" and "loving," … you can have high expectations AND a ton of fun. You can emphasize hard work and empathy. None are at odds with each other, but they do take a lot of intention. I think "great" looks like kids who have their own strong sense of self/confidence, doing what they want at a high level AND strongly connected with me/their family.

"Ok Jesse, enough philosophizing. How do you actually show up around your kids?"

Here are some specific things I do:


I am HUGE on saying NO and setting clear agreements with our kids. I read once that "no boundaries" actually increase anxiety in kids because humans are hardwired to find a boundary to feel safe. Once you say NO or take something away, your child may cry. But once you both survive it, everyone is better off.

People are shocked at my house around mealtime: my kids for years have sat down (mostly) without getting up, fed themselves and not complained about food. I created this when they were <5 and <3:

It sits on our wall and my kids can tell you each agreement by heart.

As they've gotten older, we emphasize responsibilities (like chores, Kumon, music practice) aligned to privileges (screen time, fun outings, etc)

Loving Empathy

One of the most powerful things I've learned from my coach is you can hold space for someone, show them tons of empathy WHILE maintaining a boundary.

My boundaries lead me to say "no dessert," and my empathy comes through when I add: "oof, you lost your dessert because you were inappropriate at the dinner table. That stinks, I'm so sorry. I can see why you're upset, I'd be upset too."

You can empathize while being firm. It takes learning, practice and most importantly you have to be in an open/untriggered state (more on that later). But once you get it, it's a massive unlock.

Work Ethic/Being Great

I emphasize both working hard/practice and the value of being great/excellent. My son is a borderline genius and he has the challenges a lot of genius kids have: most things come easy to him so when something doesn't come easy, he loses it!

In either case, practice is the answer. For math/piano (both of which he's a 'natural'), practice will get him to an elite level. For sports or video games (which aren't as natural), practice will get him to be great.

Work ethic is a value I want them to build early and often.

Related to this, I tell them they can truly be anything they want, (but not everything).. and the key, of course, is hard work/practice. Excellence/Success to me stems from WORK ETHIC more than anything.


I make a lot of effort to connect with my kids.

The stereotypical dad is the one who "loves you but never told you and who struggled with emotions/connection." I strive to be the opposite of that.

I make it a point to say hello and goodbye to them whenever I leave the house. I do bedtime 4 nights a week and still sneak in to kiss them goodnight after they’ve fallen asleep on the nights I'm not there. When I travel, I try to FaceTime or send them quick videos so we feel connected. I'm far from perfect but I try to leave my phone in another room when I'm around them. I randomly tell them I accept and am proud of them for being who they are. I think words and affirmations matter (this isn't something I grew up with). I do believe in affirming effort/acceptance vs achievements/abilities, which is a core tenet of building a growth mindset (google it!).


I regularly ask my kids for quick reflections. After tennis practice, I say "what's one thing you did well and one you can do better?" If they get into an argument, I ask something similar. At dinner, we reflect on things that made them happy or sad, fun or annoyed. My goal here is two fold:

  1. Make reflection a regular part of their internal systems, and
  2. "De-charge" any given situation…i.e. to neutralize a bias of "I’m bad at tennis, I’m good at math." The reality is neither of those are true, some things went well and some can be improved. I want that to be their perpetual motion.

One related point here is we try to emphasize mistakes with our kids a lot (both historical and current) and not only 'make room" for them but emphasize them as CRITICAL for learning/success. I think it’s important to LET them make mistakes and then help them LEARN/reflect on them. That can range from putting their shoes on the wrong foot to choosing not to follow instructions. I believe most people don't learn much being told something but rather by experience/mistakes. I want to create this environment for them.

The funniest one I recently shared with them is when I was 12 years old, I lit a pack of bottle rockets in my pocket IN THE MALL. I was flicking a lighter in the SAME pocket as the bottle rockets (which I was hiding from my dad). I got 2nd/3rd degree burns on BOTH hands and had to walk around middle school with a “thumbs up” gauze for 2 weeks.

Mistakes like those shaped me and I want my kids to hear them!


This has been a big one for me on my personal journey. 3 years after I decided not to sell Ampush in 2015, I had tons of regrets and couldn’t forgive myself for not doing the deal I was offered. Acceptance is something I try to emphasize with my kids. Often we are taught to resist/not accept what IS and what is happening around us. This can be external but I think it’s toughest internally (e.g. when you disappoint yourself). I think it can be even worse when parents criticize their kids (usually because they were criticized and believe it will help their kids be better).

What I've come to see in myself and hope to pass on to my kids… nothing has to be wrong/broken for me to WANT better and to improve. Another phrase my wife and I use with the kids and each other: "let’s not make them WRONG for that." Kid spills a drink everywhere? Acknowledge it happened, work to clean it up and then see if there's anything to learn. Fight breaks out? Observe what is happening and bring voice, avoid judgment.

I think this combined with generally orienting towards positivity can be very powerful. I heard once that your parent’s voice becomes your inner voice and that really stuck with me.


I'm a BIG fan of the book The Big Leap by Gay Hendricks which talks about "The Upper Limit Problem" (here’s a thread I wrote on it). TL;DR is that your parents/upbringing sets your level of "happiness" like a thermostat when you're a kid. The best example is that data shows most lotto winners end up similar/less happy 5-10 years after winning and often with the SAME amount of $ they had prior to winning! Once an adult, it can be tough to break through that upper limit set by your parents. When things get good, you subconsciously bring yourself down.

I believe this to be true and IF it is… then that means I’M SETTING MY KIDS UPPER LIMITS.

Well shit, I want that thermostat set AS HIGH AS POSSIBLE. I want them to BELIEVE life is here for you. It can be super enjoyable, fun, exciting, rewarding and everything in between.

I play video games with my son. I take my daughter on fancy dates with flowers and a yummy dessert that's all hers. We travel the world. My son loves the phrase: "everything in moderation including moderation." I obviously believe in hard work but I'm not a fan of "you must suffer to succeed." We do April fools big time, weekly movie nights, we laugh and kid and teach them curse words. Because I want them to know and expect that LIFE IS FUN.

So that's my list. If you read this and found it valuable, please let me know or share it with someone! It was super helpful for me to write it.

Last but not least: this email is aspirational. I do everything I said above and I think I show up to my expectations 7/10 times, but I’m always improving. My most important learning in parenting (and entrepreneurship for that matter) is to KNOW myself and where I am in any given moment. Am I open, curious, looking to learn, in a state of "love" or am I closed, threatened and in a state of "fear?” The latter happens all the time to me because I'm human. I try to cut the guilt, ACCEPT myself for what happened and then I do the most important thing:

I apologize and take responsibility. It sounds like this:

"Hey buddy, when we went to tennis I'm sorry I raised my voice and said some mean things. I was feeling nervous and frustrated because of my own issues with being late. There isn't something wrong with you. Here's some things I can do differently next time."

And more than anything else I wrote above, I think this will have the most impact on my kids.


Bonus: If you’re interested in learning more, check out this pdf on Conscious Parenting by The Conscious Leadership Group, and also make sure to check out this NYTimes article on Raising Successful Children. They’re both great reads.

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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