Bootstrapped Giants

2023: The Best Year of my Life

Published 3 months ago • 6 min read

2023 was the year when more than a decade of hard work and personal growth finally paid off. It was absolutely the best year of my life. I can't wait to tell you about it and share my top 3 learnings. My hope is that it inspires you to work hard for what you want in life.

But before I do, I want to share a "cheat code." My long time coach and friend, Dave Kashen, is offering his flagship 3-month course for founders called The Inner Game of Entrepreneurship starting on 1/30 and a new 4-week course for managers called The Inner Game of Leadership starting on 2/9. I'm not getting paid to promote these. Dave is the closest thing to a life/business cheat code I've experienced so I want to share it with you all. Mention me or Bootstrapped Giants in your application and he'll give you 20% off.

Now, let's talk about 2023. If there was one "theme" here, it would be 2023 as a "harvest" year for the 5+ years preceding it. So while this year was incredible, it's important to remind everyone (including myself) of the work that went into it.

Here are the 2023 highlights:


My marriage to Deepika went to the next level as I learned to connect with my heart instead of my head. In the past, if she said, "it would be nice if you do the dishes," my typical response was, “let's make a work plan to divide and conquer." She’d do it, but sort of roll her eyes. Now, I randomly do the dishes when I sense she’s had a long day. It’s barely once a week but 10x more meaningful than a “work plan.” Also, I focus on listening and reflecting back to her what I hear. I almost entirely dropped defensiveness and I'm cherishing her in big and small ways. I realized my entire life starts with her.


Mila was born. She was a long time in the making. Her name means Miracle and that she is. Ricky (8) and Serena (6) are absolutely incredible kids and I'm having a blast with them. I'm doing my best to show up as a steward of their souls i.e. to meet them where they are and help them be who they are meant to be (vs what I think they should be). I learned how to Ski for the first time and both my older kids love it - I'm hoping it becomes a tradition I do with them forever. If you’re a new subscriber, here’s my take on parenting.

Rest & Renewal

I traveled to Turkey, France, Portugal, Jackson Hole, Miami, California, NY, and multiple other places for memorable trips. I believe rest and renewal is critical for the Marathon.


I lost over 20 lbs and cut my body fat in half. A few things changed for me:

  1. I embraced HABITS over Goals. I’ve lost weight FAST before with P90X and fad diets. This time I focused on systems and the weight dropped much slower but it didn’t take willpower. It felt easier and I think I’ll sustain.
  2. I also used LOTS of help: I got a nutritionist from MyBodyTutor on Sam Parr's recc. She helps me plan, be accountable and more conscious. I've done a high protein, low carb diet and have done the Prolon Fast a few times. I play tennis 3x a week. I lift with a trainer 2x a week for an hour (they are intense) and I walk >1 hour 2-3 days a week.


My spirituality has gone to another level. I meditate/pray 30-60 minutes a day. I feel more connected to Source than ever before. I've become more curious about my faith and spirituality in general. I've enjoyed reading "The True Name" by Soho. I find that the more I connect, meditate, etc… I’m more trusting and accepting of all things in the world. This has reduced stress, made me a better decision maker and a more effective coach/leader.

Ampush Sale

We started the year SELLING AMPUSH, the company I started with my college roommates / closest friends. In the 13 years we ran it, we experienced every twist and turn you can imagine. We divested 1 company, acquired 2, invested in several, and we re-invented the entire business at least twice. This had so many emotions. The best part was the 500+ emails I received from former employees/clients about how Ampush impacted their career. It made the human impact so real to me. We entrepreneurs work hard, but I can tell you that the payoff is worth it.

Gateway X (GX)

Gateway X, my venture studio for bootstrapping businesses went to the next level:

  • We shut Kahani down and I decided (along with Adam - GX CTO, and Nak - GX COO) to go all in on the venture studio. I'm writing a detailed thread on this next week, it’s an interesting story.
  • GrowthAssistant, high quality global marketing talent biz, crossed 8 figures in revenue!
  • UnCo, my first DTC brand, crossed $3M in revenue and is cash flow positive
  • Aux Insights, a tech-enabled Marketing Consultancy for PE firms, launched and is already profitable with an amazing team
  • Bootstrapped Giants, the best community of ambitious entrepreneurs who want to grow off their profits, launched and is getting 9M+ impressions a month

Challenges & Learnings

It was an amazing year filled with some awesome moments, plenty of challenges and opportunities for growth.

Here are my biggest 3 challenges and 3 biggest learnings from the year:


1) Managing my time with GX - while I think I made strides here, this continues to be a challenge.

At one point this year, we had 3 new ventures going and realized it was just too much. There were weeks where I’d be double booked for interviews for Aux and pitching Kahani at the same time. The list was just too long for me to do great work. I committed to only one "new" venture per year.

Making sure the GX CEOs feel fully supported is my top priority but I can get pulled in multiple directions at one time. I continue to work on this but don't have any genius answers. Hit reply if you have good tricks and I’ll share them out! Here's my current schedule if you're curious:

2) How to be "coach" vs "boss" - I have a unique relationship with everyone at GX, especially the CEOs.

I want them to be as standalone as possible while also absorbing cultural values I find critical. I am their partner, not their boss. But sometimes we both show up like I am a manager vs a coach. A coach holds space and asks questions, a manager tries to assess and figure out next steps. Coach is my preferred relationship: listening actively, asking questions, challenging them but letting them make decisions and drive.

3) Staying present - whether it's being on my phone too much or not fully being there during a tv show, kids game, or in a meeting.

I'm always working on staying present. At GX, we often start meetings with quick breathing or presencing exercises. I do this at dinner with my wife and in other situations. I even removed my phone from my bedroom and try to leave it whenever possible.


1) If you trust yourself, everyone else will trust you.

After raising $3.5M+ and committing to be the CEO of Kahani - the ecomm saas tool I started - my insides didn't feel right. I wasn't excited to be running a startup day to day anymore. I felt more purpose in the venture studio and supporting others as CEO/Founder.

But the pressure of commitments I had made to investors, employees, and customers was insane. With a lot of support and courage, I decided to shut it down and return the money. I trusted what I was feeling and was candid with everyone around me. It led to better relationships everywhere and an unlock of my energy.

2) Intellect is limited.

This was a new and big one for me. Intuition and Love have always felt like squishy unreal concepts to me. Reason and Logic was the way. But whether it was the example above, or when I reflect on starting GrowthAssistants or partnering with people like Kasey Grelle… intuition has served me way more than Intellect. Both are important to be sure but I have benefitted from building this new sense.

3) Great things take time/consistency.

Like I said to start…my health, Ampush, my marriage, kids…

I'm 39 going on 40. It took 10, arguably 20 years to position myself this way (since I was a 15 year old studying hard for the PSAT). So if I leave you with one thing, it's this: be long term patient and urgent daily. I'm grateful and lucky for what has happened in my life: my parents, teachers, friends, mentors who helped me get here combined with a lot of time and hard work.

That's all I've got, have a great 2024 everyone!!!

What happened to you in 2023? Tell me your learnings and goals for '24! I read every email.


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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