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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.

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Featured Post

2 life-changing minutes

About 9 years ago, my wife scooped me up from the airport on a Friday night after a long week in NYC doing sales/client stuff. I said “Hi” and continued to text and email away. She asked about my trip and I gave her half answers. “It was good. Fun, learned a lot.” As we got home, I could feel her frustration growing. Finally, she exploded. I’ll spare you the details but the gist was: “I wish you would show more appreciation and gratitude! For example, say 'THANK YOU' when I pick you up from...

2 days ago • 6 min read

One of the secrets to my success is that my partners, clients, and team can count on me to respond to their emails, fast. It also removes the stress that most people carry around from having a cluttered inbox. For over a decade I taught leaders how to get to inbox zero, but few could put in the work to achieve it. Then, a few years ago, I found something that did the trick: Superhuman. Superhuman uses speed and AI to enable anyone to reach inbox zero. All the leaders of my companies use it. I...

5 days ago • 1 min read

The most common question I get: HOW are you starting and running so many businesses simultaneously?! The short answer is: I’m not. I’ve partnered with a bunch of incredible people to bring these organizations to life. The next question is: “Fine, but how does it all actually work? How do you interact and lead these people?” “Well…uhhh…where do I start?” I finally have a good answer and it's in this email. Today, I’m doing something very different. I invited my friend Andrew Warner to write...

9 days ago • 6 min read

I'm turning the Bootstrapped Giants newsletter into a business and I want to bring you along for the ride by showing both my process AND the revenue. First, let's talk about WHY Bootstrapped Giants MUST be a business. When my partners and I sold Ampush for life-changing money, we saw how powerful bootstrapping can be. Today, I continue to see how big bootstrapped companies can be, because I'm growing several of them at Gateway X. My startup studio will build a billion-dollar business that's...

11 days ago • 5 min read

Two weeks ago, I asked my newsletter readers to hit reply and tell me their problems. I got hundreds of responses. THANK YOU. Your responses mean so much to me and fuel me to keep delivering value. I'm still working my way through emailing every single one of you. But one topic that came up is “How do I grow my B2B business? How do I do sales?" I got you. Most of the businesses I founded did/do B2B sales. In fact, I’m still very involved in sales for all the GX businesses. My advice to anyone...

16 days ago • 3 min read

"Stop, Jesse. Words Matter." I stared at Ric Elias (Billionaire Founder of Red Ventures). I was confused. After an uncomfortable silence, I asked: "What do you mean?" "Well, you just told me you're reorganizing the company. You're having a small team run a dying business unit to maximize profit while you shut it down. And you said you're calling it the 'Growth' team. But there is nothing 'growth' about that team."I noticed myself getting irritated. My actual thought was: Why is this dude...

23 days ago • 6 min read

After I sold my first company, Ampush, I promised myself that whatever I did next would maximize my purpose vs maximize my bank account. After a year of working through this with my coach, my WHY became clear: To create space for others to learn/grow through the power of entrepreneurship. If you ask anyone who knows me well, or who has met me, they'll tell you I'm eager to help people learn and grow. My “dojo” of choice is the entrepreneurial journey. Because it's what I know and (like...

about 1 month ago • 1 min read

Like many people reading this, I used to CEO all wrong. What I used to do: tell people to email me things, or send me “to-dos” like reviewing a contract, writing a product spec, or preparing a sales deck and I'd get them done. And here's what my schedule was like: I'd have meetings all day to look at progress, make decisions, host interviews, and more. All the while, I'd barely be present. Since I had so many things to get done, I'd always be multi-tasking. After work, I'd head home to put my...

about 1 month ago • 5 min read

Last week, I stared at my best friend since 7th grade pre-algebra. She shifted in her seat, a little uncomfortable. I stared and said: “So, what do YOU want for your life?” Her response: “I don’t even know where to begin with that question.” That led to this email and nailing one of the most important questions facing every entrepreneur. Here is the backstory: Adriane (left) and I (right) in high school! Adriane (my BFF) and I started GrowthAssistant 3 years ago this month. It took off faster...

about 1 month ago • 5 min read

After a month of negotiating with the Muhammad Ali of negotiations (Ric Elias), we were extremely close to a deal where Red Ventures would buy ~20% of Ampush...then I made one critical request. I got on the phone with Ric and said: “Thank you for believing in us. We are going to take this deal no matter what and are excited. We DO have one request though. We 3 founders are at an age where we’d love to buy a house. In the Bay Area. It’s quite expensive. Since you’ve said you plan to buy the...

about 2 months ago • 6 min read
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