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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.

Featured Post

My Weekly Schedule

A newsletter reader said, "I'm struggling to keep up with one business. How do you find the time to run multiple companies, while being a present father and keeping up with your health?" My short answer: I have an incredibly routinized schedule. But you subscribe for depth, so let's take a deep dive into my week in hopes that it serves as inspiration or gives you ideas for how you can spend your time. Before we go there: WHY even have a weekly schedule? I started doing this in 2015 after my...

5 days ago • 4 min read

Thank you for FINALLY doing it, Jesse.”​One of my top performers stopped by my desk with a relieved look on her face.​“What do you mean FINALLY?” I responded​“Well, Bob has been a toxic employee for almost 2 years and we all knew it. We figured you had your reasons for keeping him on and trusted you but it's hard not to feel a little lighter with him gone.” I felt relieved but also… embarrassed. Because I kept trying to accommodate Bob – despite his incompatibility with the role, our culture,...

12 days ago • 5 min read

Last week, I told you how working with a coach enabled me to grow my business, find my true purpose, and even make me a better husband. Of course, the follow up question on every founder’s mind was: How do I get RESULTS by working with a coach? This email answers that question. But before I start, there are two prerequisite questions: How do you find and select a coach? What do coaches do? How do you find and select a coach? Let’s start there. The best way to find a coach is to ask around...

19 days ago • 5 min read

I Quit.” After 7 years of running hard every day to build my dream company, I couldn’t believe those words were coming out of my mouth. It was 2017 and I was staring at my best friend and co-founder, Nick Shah. I had been out for a month on my second paternity leave and this was supposed to be a meeting for me to “ramp back up.” The problem: We had charged hard on Ampush for 5 years from 2010-2015. My wife never saw me. The business was always on my mind. It was a roller coaster of ups and...

26 days ago • 8 min read

At 22, I landed my dream job. Business Analyst at McKinsey & Company. I was told there is no better place to start your career out of college and I was stoked. Within 6 months, I got staffed on a HUGE project. The largest (at the time) private equity deal in HISTORY: KKR was buying Bell Canada for $45 BILLION. I got my assignment and was hopping on a flight to Toronto, immediately. There were 12 total team members and we had 6 weeks to diligence this business for a sophisticated and...

about 1 month ago • 7 min read

About 6 months into starting Gateway X, I got the call every entrepreneur dreams of… David Rabie, the Founder/CEO of Tovala (smart oven/food subscription biz) was an Ampush client, friend, and let me invest in his company. Jesse, my first engineer… a DREAM first engineer is starting to look around after 5 years. We are 400+ people and he’s not having fun anymore.” I felt my body tingle. After a few meetings, I hired Adam Brakhane (now Gateway X’s CTO). Within months of him joining, we...

about 1 month ago • 5 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...

about 2 months ago • 6 min read

Ok, Story Time!!​The year is 2017. I'm on the phone with Ric Elias, Billionaire Founder of Red Ventures who had recently invested in my company Ampush. We were having a shitty year. Me: I'm debating what's the right move… should we retain smaller clients or sunset them to go for bigger fish, how should I think about this? Did you ever face something similar?​ Ric: I think that's the wrong question, Jesse.​ Me: Well, what question should I ask?​ Ric: What do YOU want next year?​ Me: How does...

about 2 months ago • 2 min read

In the spirit of annual planning, today I'm going to share my favorite "secret" framework for stepping back and looking at your business and getting it to grow the way you want. I learned this framework from two amazing coaches: Bryan Franklin and Dave Kashen. It goes a little something like this: Every business in its "natural, aligned" state grows EFFORTLESSLY. So assuming your business is not growing effortlessly, it's due to some form of MISALIGNMENT. Misalignment of WHAT, Jesse?" I...

2 months ago • 4 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...

2 months ago • 10 min read
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