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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

Painful news about one of my companies

In the last few weeks, we made the tough decision to pivot Unbloat, our e-commerce brand, from a growth focus to “profit max.” That has meant parting ways with all our agency partners, pulling most of the team off (luckily we placed them with other GX companies), and most brutally: looking back at the last two years and realizing we were wrong. Today’s email started as a card in Notion. After I wrote the email, the card was assigned to my editor. When he finished, he assigned it to my...

2 days ago • 5 min read

A few days ago, I took a day trip to Charlotte. I spent 25+ hours prepping for my time there. On the day of the trip, I woke up at 5 am, flew at 7 am, and was home by 11 pm. It was a long day. I made it longer when I unintentionally woke my 4-month-old when I got home. I had a long, tiring day. Why did I do it? Feeling guilty about not responding to emails faster? I got you. Superhuman is how my team flies through email. Readers of my newsletter try it free, here. Simple: Friendship. Ric...

9 days ago • 5 min read

In early 2012, I was sitting with a VC. My first business, Ampush, had done $2M in revenue in 2010 and then $19M in revenue in 2011 while generating >$4M in EBITDA. At 27 years old, I was already living my dream - running a fast-growing, profitable company with customers, a unique learning culture, and long-term ambitions. Being bootstrapped used to mean “No health insurance.” Rippling changed the game. Rippling can help your team with health insurance, payroll, and more. Rippling is the HR...

16 days ago • 3 min read

A Bootstrapped B2B business hasn't really started until it has its first customer. Until then, the business is just an idea or a product. That first paying customer is everything. A few weeks ago, I introduced you to MMM, Meetings are the only Metric that Matters. "Ok Jesse," I hear you thinking. "I am getting a few meetings. How do I RUN the perfect meeting, one that’s bound to lead to that special moment: my first paying customer."Here’s how I do it: How do my companies handle...

23 days ago • 5 min read

I'm disorganized. I run a mile a minute. I'm terrible at documentation. But I understand the importance of having an organized company. That's why I work closely with our COO, Shonak “Nak” Patel. I'm turning this email over to him so he can show you how our companies run on Notion (a Bootstrapped Giants partner). If you're not using Notion and want to follow along, you can get 6-months, plus unlimited AI for free. Apply here to get the free package ($6,000 in savings). When asked for a...

26 days ago • 4 min read

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...

30 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...

about 1 month 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...

about 1 month 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...

about 1 month 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...

about 1 month ago • 3 min read
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