Gateway X

We build and launch companies from scratch. 

Each company has a unique insight and we are building both B2C and B2B companies. 

Our purpose is to help people learn, grow and be the best versions of themselves through the journey of entrepreneurship. We value being fast, data-driven, customer centric and adaptable in our approach.

We will be a profitable, long-term organization with an extraordinary culture and several unique winning companies. 

Founded in 2021, Gateway X is proudly based in St. Louis, MO., and will embrace a hybrid office/remote work approach.

Founder & CEO

Aux Insights

Executive Chairman & Founder

GrowthAssistant

We provide trained, full time offshore employees to handle manual tasks for Growth Marketing like campaign mgmt/reporting, design, and influencer/affiliate mgmt.

Scale your business faster, smarter and more affordably.

Clients include: Hubspot, ClickUp, Calm, CommonThread, Doordash...

Kahani

Founder & Executive Chairman

Schnuck Markets, Inc.

Board Member

Redesign Health

Advisor

Blue {Seed} Capital

Ampush

Ampush was acquired in January 2023 by Tinuiti/New Mountain Capital.

Co-Founder & Board Director

CEO & Co-Founder

My Subscription Addiction

Building THE destination for customers to discover and sign up for DTC brands and subscription services that make life easier and more delightful.

We acquired this amazing internet gem in 2018 and are building it independently from Ampush.

Executive Chairman

Milo.com

Hi! I'm Jesse, a founder and investor who loves helping people grow through entrepreneurship.

Everything I know today comes from bootstrapping my first business Ampush to a mid 8-figure exit.

During my time there, we managed over $1BN of digital media spend, grew to 100+ employees, and partnered with brands such as Uber, Birch box, and Hulu.

It was quite the rollercoaster and set the foundation for what I do today:

Build ambitious bootstrapped companies at my venture studio Gateway X. Our portfolio includes:

Growth Assistant, which embeds the best offshore growth marketers into your company.

Aux Insights, which offers digital marketing due diligence and value creation services for private equity.

Unbloat, a DTC brand that offers doctor-formulated supplements designed to improve gut health.

Aside from venture building, I share my learnings on topics like sales, finance, hiring and more in my weekly newsletter "Bootstrapped Giants".

When I'm not working, I love to travel, play tennis, watch Pixar movies, and indulge in dark chocolate.

I'm based in St. Louis, MO with my wife Deepika, son Ricky, and daughters Serena and Mika.

So, if you're interested in bootstrapping, growth marketing, ecom, or leadership, follow me on LinkedIn.

8 ways I am a present father and hardcore entrepreneur:

1. Keep a very routinized schedule (MWF get home by 6 to do bedtime, play tennis T/Th at 8 pm, my team knows my schedule, etc)

2. Work Sunday afternoons.  Get planned and organized each week.

3. Delegate aggressively - I have virtually no individual contributor work

4. “Work” with my kids.  I do email/work when they do Kumon or other stuff

5. Fully unplug on Vacation - memories are made when everyone is present

6. Master the DAY TRIP - I fly to 3-5 cities a month, with zero nights away (St. Louis helps)

7. Partner well - Find great people to be CEOs and team members

8. Break the rules - every now and again, I go hard for a week and ask my family for grace, or the opposite: I travel for a week unplanned w the family and ask my team for grace.

What works for you?

Jesse Pujji

My first company Ampush scaled paid social for Uber, Dollar Shave Club, Clash of Clans, and many other top B2C companies.

One secret we learned early?  The marketing sprint.

I have an awesome Notion template for you to help you execute on priorities fast..

Comment “Sprint” and I’ll DM you!

Update: This post got over 2,000 comments. I can't DM everyone, so I'll make this template public, here:
https://lnkd.in/gtzu9WNs

You never heard of my mentor, but he:
• Built a $10B company
• Acquired 12 MEGA brands
• Gets home daily by 6pm
• Built one of the most amazing cultures I've witnessed

6 most important lessons I learned from him:

Ric Elias is one of the most successful + least-known entrepreneurs of our generation.

His company Red Ventures is the largest digital media company in the US.

He's also one of the most humble, kind-hearted people I know. And an amazing mentor.

Alright...

1⃣Lesson 1: 
You own your business, your business doesn't own you

2017, I was feeling stuck after many years of running Ampush. 

He encouraged me to use my work for personal growth + ask my team to do the same.  

He reminded me that as the CEO/founder I can change anything

2⃣Lesson 2: 
Culture is what you tolerate.

No matter how hard I look, I can't find a better definition of culture.

Allow complacency? People will stop growing.

Tolerate people not knowing their numbers? They won't know them.

And If you let people be themselves, they'll surprise you.

High bar + kindness = great culture.

3⃣Lesson 3: 
Pursue the 3 Fer

Biz leaders often debate things like profit vs growth

Ric prefers to greenlight initiatives where we somehow deliver 3 wins. e.g., it has to drive growth, profit and learning

4⃣Lesson 4: 
People are the purpose

6 months into our partnership, Ric asked "how come you never call and share your challenges?"

Me: "I'm like 2% of your business, it's not worth your time"

Ric: "but you are my friend and I'm here to support you"

That left a HUGE impact.

Side note: He has quietly funded scholarships for ~500 DACA students through his Golden Door Scholars program and built a nonprofit called Road to Hire that has trained 1700 young people to date

Part of Giving Pledge, committing to giving away >50% of his wealth. Raised $5M (half his own) to help Puerto Rico after Hurricane Maria.

He never forgets People are the purpose.
He taught me that there is more to business than just capital, profit, and growth.

5⃣Lesson 5: 
Tell me how someone is paid and I'll tell you how they'll behave

The most important behaviors are the ones people do when no one is looking.

Incentives are that invisible hand driving what people do.  

6⃣Lesson 6: 
Top down P&L targets are arbitrary, and dangerous.

"Ric, we will pursue a 25% EBITDA margin this year"

"Jesse, why not 35%? why not 15%?  

Whatever target you choose, you will take actions to land there.

Instead, focus on being great at the actions, focus on 
being intentional. 

Target the actions you'll take, accomplish, or other causal metrics instead of an end goal and you'll surpass your wildest dreams of profit margins!

Those are the 6 Lessons.
When it's all said and done, I truly believe Ric & Red Ventures will have many books written about them. 

I'm grateful to know Ric, count him as a mentor & to have learned all these amazing lessons from him.

Check the post below for a recording of my recent conversation with him.

DoorDash is INSANE 

+ Founded ~ 10 years ago 
+ With 120k in capital
+ Competing against giants like Uber and GrubHub

10 years later...

+ America's BIGGEST player in delivery 
+ $50B public market cap

My friend Andy runs growth marketing for them. 

He built the engine that scaled both sides of their marketplace. 

I'm sitting down with him in 10 days to ask how he did it. 

And how he used global talent to maximize leverage.

Come be a fly on the wall

When my remote team grew, we had a problem: how can new hires be as amazing as our top people? 
 
Our solution? Well-designed playbooks. 
 
If you have a team, steal our Notion playbook template. 
 
Comment "Notion" and I'll DM you!

I hacked Goldman Sachs.

And it helped me build and sell Ampush for mid-8 figures.

This is a wild story👇

Summer 2009, I’m on the desk at Goldman (hedge fund analyst). Using one of my fav tools.

GLG.

What’s GLG? It’s a massive (9-fig) expert network biz - AKA they say to Wall St. hedge, “we’ll get you on the phone with an expert on any topic you want”.

Using GLG I became an expert in Trucks. Auto-dealers. Hell, even farming.

Around the same time, my best friend Nick’s job offer got pulled. It was 2008...the hedge fund he was going to work at blew up. So, Nick and I started spitting biz ideas back and forth.

We had a MILLION ideas but no way to validate them. Then a light bulb went off...

I didn't want to be an excel monkey, so I went to my boss’s office and put in my 2wks.

BUT...for those 2wks I had an UNLIMITED SUBSCRIPTION to GLG.

I could learn about new trends and use it to come up with THE idea. So we talked to founders of huge agencies. Big shot CMO’s. All these industry experts. 100% FREE.

I ended up doing 65 GLG calls on Goldman's dime.

6mo later, and thanks to all our free GLG calls, we found THE IDEA:
*lead-gen for online education*

Nobody was using digital mktg at the time (pre FB ads), so there was a huge opp.

Then a buddy from a hedge fund called me.

“Hey Jesse, There’s this company called QuinStreet going public. Isn't this kind of like what you're doing with your new digital mktg co? Can you teach us about QuinStreet?"

So we told them everything we knew, and a second lightbulb went off...I immediately call GLG HQ and say...

“Hey GLG! I'm an expert in digital mktg. Will you pay me $500/hr to consult with hedge funds?” And they're like "YEAH, because we have no idea what these companies do."

Now, we're taking 5-7 GLG calls/wk @ $500/hr and literally teaching them about digital mktg, which we learned from GLG calls before.

On one of our calls, they ask: “Do you guys have any research you've put together in a pitch deck?” Of course, we didn't, but we said...

“Sure. We have a $5,000 report. It's 50 pages. It outlines all the competitive players and value chain, etc.”

He says: “Great, can you have it to me by Monday?”

So we pulled all-nighters and put it together over a weekend. We ended up selling around 24 reports driving over $120k!

I joke a dinner parties that this was Ampush's "angel round."

Not only did it fund Ampush in the early days, but it also taught us how to build to 8-figures.

Crazy story, but there are 3 lessons that I've kept.

1) Leverage your unfair advantage:
Using GLG at Goldman, I had a huge advantage. Today, I leverage my network heavily for our portcos.

2) Be resourceful
Bootstrapping forces you to come up with unique and interesting ideas, often with limited resources.

3) Be opportunistic
We turned a hedge fund call into a profitable gig, which ultimately helped us gain the knowledge and resources to start Ampush.

I usually save these stories for my free newsletter. Link below.

I’m going to die poor.

2017, I was flying high. My business was generating millions. But I was depleted.

I got a coach. He challenged ALL my assumptions. I stopped torturing myself. And guess what, I became more successful.

One of his suggestions: “Read the book, Die with Zero.”
Wow.

4 things stuck with me.

1. Dying with money = overworking
Imagine making $100/year and dying with $300k. You burned 3 years working that you could have spent living.

2. Earn Memory Dividends
I’m throwing a 40th bday blowout. People I love will be there. Those memory dividends will pour in for years.

3. Inheritance NOW
“But Jesse,” you say, “If you die with money, your kids can inherit it.” Blah. The average US inheritance is 62 years old! But come work out with me and you’ll understand that my kids might have to wait forever. Why not let them enjoy NOW, while I’m alive?!

4. Decade Bucket List
Your bucket list sucks. You write “hike Kilimanjaro” and wait for time to do it. Then you turn 70 and realize you can’t climb! Instead of 1 bucket list, make a new bucket list for each decade of your life.

Bottom Line:

We obsess about how we’ll make money, but we get lazy about how we spend it.

It’s rooted in an irrational fear of loss and running out of money, both of which are not empirical risks.

So get much more intentional and long-term about how you will spend the money you’re slaving away making.

⇒ Follow me, to check my progress.

I consistently close sales in 30-minute Zoom meetings

Steal my format:

2 Min: Small talk
↳ "Where are you today?" etc

2 Min: Magic question
↳ "What led you to take this meeting?" It's magic because they tell you why they need you.

5 Mins: Your story
↳ People love stories, esp founder stories. Tell them why your product/company/service exits.

5 Min: Show, don't tell
↳ Share your screen and do a demo.

5 Min: Their questions
↳ Their questions are a critical signal of interest.

5 Min: Your discovery
↳ You're asking about their issues, decision process, etc.

5 Min: Next steps
↳ Lock in what happens next, even book the next meeting.

A smooth talker tricked me...so I overhauled my hiring process.

My exec team needed a new CRO. We met a guy who blew us away.

He was the missing piece my team had been searching for, so we hired him.

He was a disaster from day one. Couldn't even unveil his growth plan at a company-wide meeting. I s*#t you not, with a straight face he said, "My laptop died. I lost the presentation."

3 months after hiring him, we fired him.

When we did a retro, our mistake hit us in the face.

The guy had a perfect 1-hour "talk track."

If you've hired execs, you know they can be masters of BS, with carefully cultivated talk tracks.

Our solution:

Every executive we hire goes through 3 touchpoints, including a dinner.

After a couple of touchpoints and a 2-3 hour LONG dinner, a person will show who they really are.

This guy went from writer to my Marketing Lead in 10 months.

How he did it is a model for career growth.

Now I need to find another writer like him for my newest company, Bootstrapped Giants.

Achint Singh (in the white shirt) was a student when I met him. He wanted a summer job at a place where he could learn.

Because he was constantly reading business books, I asked him to start writing for GrowthAssistant. Even though he wasn't a writer, his posts kept going viral and leading to sales.

His secret? He used a 3-part process.

1. COLLECT: He put together a collection of substantive articles that were shared heavily on social media.

2. TEMPLATIZE: He created templates based on what worked for other writers.

3. ANALYZE: He kept evaluating results and adjusting his output. (ex: news-related posts did well for him, so he created a process for jumping on news stories.)

Through it all, he kept finding ways to make his writing sing because of how beautifully it was written.

Now that he moved up, we need another writer. Our CEO and I will personally coach you.

If you or someone you know is a driven writer who wants to create content that will be shared by millions, fill out the form below, and let's talk

One of my favorite Bootstrapped Billionaires: 

- Took a high school equivalency exam at 8 years old to start working earlier - talk abt hustle

- Scaled his newspaper subscription business to $200K py out of his college dorm room 💸

- Knew he was onto something and dropped out of school at 19 yrs old - as just a freshman!

- Started assembling and selling PC upgrade kits on campus
 
- This “side hustle” was named Dell Computer Corporation

- At just 27 years old, he became the youngest CEO of a Fortune 500 company

- Still owns 51% stake, bringing his net worth north of $30B

- Established Michael and Susan Dell Foundation - focused on global health and education primarily in India and South Africa

What an inspiration - I want to be Michael Dell!

Finding Product Market Fit is for suckers.

Nothing has burned more time or money than founders searching for product market fit with VC money.

I learned this the hard way.  Instead: Spend no money.  Find a bunch of people with a big problem.  And then try to sell them something that solves it.

Stop running yourself in circles to start a business.

Founder/CEO @ Gateway X: Bootstrapping a venture studio to $1B. Previously, Founder/CEO of Ampush (exited).

Why is it crucial to focus on solving big problems in business?

How important is finding Product Market Fit for startups?

What are the key factors for success in startups?

Nvidia's earnings were a grand slam. 

It all started here, when Jensen delivered the first supercomputer to Open AI.

Here's the unlikely story of the former dishwasher behind the hottest company in the world:

Jensen was born in Tainan, Taiwan in 1967.

He moved to the US, got his Bachelor's at Oregon State and his Master's at Stanford.

After Stanford, Huang went to Wilfred Corrigan, CEO of LSI Logic, his former boss, to pitch his idea for Nvidia.

"That's the worst elevator pitch I've ever heard", Wilfred said to Huang.

But Huang was one of the best employees LSI Logic ever had.

So Corrigan called Don Valentine at Sequoia and asked him to fund Jense's venture.

"You can't run from your past. Even when I was a dishwasher, I was the best dishwasher Denny's had ever seen. They promoted me to busboy and I was the best, most efficient busboy they ever had."

In 1999, Nvidia invented the GPU.

This became the backbone of the graphic capabilities of modern computers.

In the next 4 years, they 9x'd revenue.

Then came one of Jensen's legendary pivots

Graphics were a powerful application, but he always wanted more.

In 2003, Jensen spoke to a quantum chemist who was using an early Nvidia product to express his algorithms. And he met more doctors at Mass General doing the same.

This opened their eyes to a new application

Parallel Processing on GPUs:

This was revolutionary because parallel processing makes GPUs significantly more efficient at certain types of computational workloads, which has powered deep tech ever since.

This and developer accessibility massively sped up both development and computing.

In the mid-2010s, Jensen and his partners made a massive bet on AI and deep learning.

As the application layer developed, Nvidia proved to be miles ahead of any other providers.

Amazon, Microsoft, Google, Twitter, Tencent, and hundreds of startups became reliant on Nvidia GPUs for their cloud computing and machine learning businesses.

OpenAI used thousands of their GPUs to train ChatGPT.

Big company CEOs boast about how much money they are spending on Nvidia's chips. There is a worldwide fight for allocation. 

AMD, Intel, etc are all relegated to playing for 2nd place.

So what are the lessons?

There are many. Here's my favorite:

Play the long game.

Jensen runs one of the most valuable companies in the world.

But it took 34 years of absolute focus, devotion, and many failures, before he got the recognition he deserved.

Greatness takes time.

I sold my agency for 8-figures. These are 5 revenue pillars that make acquirers excited about a business.

• Long wind-down provisions
Even if you're not locking clients into multi-year agreements, get them to agree to wind-down periods. Prevents abrupt revenue decreases.

• Long-term contracts
A no-brainer. Acquirers pay more for dependable revenue.

• Blue chip clients
We worked with Dollar Shave Club, Peloton, and other well-known brands. If we had a bunch of random affiliate agencies, our options would have been limited.

• Logo retention
Revenue retention needs to be above 100% to be considered a great buy. That only happens if you're growing your clients.

• Sales machine
I was doing sales up until the end, but the company didn't depend on that. We had strong sales leadership, systemized processes, and a clear pipeline.

Put yourself in the buyer's shoes and all this makes sense.

I'm disorganized. I run a mile a minute. I'm terrible at documentation.

But my team is organized because of how our COO set up Notion.

Watch this video. Get Notion for free in the link below.

In 1984, a student at UT Austin started a PC biz with a thousand dollars.

40 years later, they’ve done over $1 TRILLION in lifetime revenue. 

Michael Dell is worth $100B himself. 

Story of the OG Bootstrapped Giant 

Michael Dell started Dell Computer from his dorm room selling upgraded PCs with more memory and disk drives. 

By selling directly to customers of different sizes, he could lower the cost and provide much better service. 

He quickly moved on to building custom computers. Dell was off to a hot start. 

The biz outgrew his dorm, and Michael dropped out, officially launching his company. 

It was his first year’s financial statement that helped him convince his parents. 

In 1988, Dell Inc. went public, raising about $30 million in its IPO. 

The company expanded internationally, establishing offices in Europe, Asia, and Latin America.

And they expanded their offering: servers, workstations, components, and of course PCs. 

By 1990, they were doing $100,000,000 in revenue. 

They were one of the pioneers of mass customization: 

Dell adopted just-in-time manufacturing to reduce inventories and make quick production changes. 

They were also early adopters of e-comm: Dell launched its website in 1996.

By 2000, they had overtaken legends like HP and Compaq to become the biggest PC manufacturer in the US. 

And Michael’s direct sales model revolutionized the industry. Everyone eventually followed. 

He's a singular entrepreneur. Started one of the world's greatest companies in his dorm room. 

Stuff of legend

Last month, I turned my personal newsletter into a business.

It’s already doing $40k / month.

My secret?

I copied the best newsletters’ playbook:

1. I grow on X and LinkedIn

After my popular posts, I use Hypefury to auto-append a link to my newsletter.

The majority of my subscribers come from those links.

I resisted it because it seemed overdone by other writers, but it works.

If you haven’t done it, start dropping links on your best posts.

2. I have a good source of content

Nearly every successful creator says, “Publish consistently!”

But most of them are full-time creators. They have the time to create.

I have multiple businesses to lead. Most of my time is spent leading the Gateway X family of companies.

My solution? I turn what I tell my team into content for my newsletter. It’s more authentic.

If you want to publish consistently, look for what you’re already saying/doing and turn that into your content.

3. I get geeky

In one of my newsletters, I explained how I use negative working capital to grow my businesses.

Most people’s eyes would glaze at topics like that. But newsletter readers want that level of depth, as long as you explain it well and illustrate it with clear examples.

If you’re publishing an email list, get geeky.

4. I picked an ignored audience

If an entrepreneur is trying to build a VC-backed company, they have many resources. Paul Graham’s essays, TechCrunch’s funding news, etc.

But bootstrappers are largely ignored. And those who want to bootstrap AND build something BIG are completely ignored.

My newsletter is their home.

If you’re picking a topic, don’t be the millionth newsletter on AI. Look for someone uniquely underserved.

5. I asked for the sale

I’ve seen newsletters with bigger audiences than mine not make a dime because they’re scared of asking for a sale.

When I decided to turn this into a business, I posted a public request for sponsors and I sent private messages to people at companies I wanted to work with.

The best newsletters ask for the sale. Look at the bottom of your favorite newsletter. Chances are there’s a link to sponsor it.

If you want revenue, you need to ask for it.

Founders are more likely to sell to Private Equity than IPO, but they don’t know the basic math behind PE.

Let's go through the numbers.

If a PE firm buys a company, the buyout might look like this.

Target company's EBITDA: $10 mil
Price paid (10 X EBITDA): $100 mil
Payment via: $50 mil equity and $50 mil debt at 10% interest

Let's jump forward 5 years.

Scenario 1: What happens if the company has low growth?

EBITDA: $11 mil
Valuation (10 X EBITDA): $110 mil
Interest paid: $25 mil
Debt paid down (using profits): $25 mil
Internal rate of return: 11%

[IRR math: current valuation ($110M) - debt ($25M) = equity value ($85M). So value ($85M) ÷ initial equity paid ($50M) = 1.7X return or 11% IRR]

Scenario 2: What happens if the company has a solid 20% growth?

EBITDA: $20M
Valuation (12 X EBITDA): $240M
Interest paid: $25 mil
Debt paid off FULLY (using profits): $50M
Internal rate of return: 36%

[IRR math: current valuation ($240M) - debt ($0) = equity value ($240M). So value ($240M) ÷ initial equity paid ($50M) = 4.8X return or 36% IRR]

Either return is better than the S&P.

I just watched one of my salespeople make a common sales mistake. It became a teachable moment.

He was talking with a potential sponsor about Bootstrapped Giants, my newsletter.

First the good: He studied up on the sponsor. Put together a clear offer. And organized his visuals.

Here's the mistake: He made a gorgeous deck, full of screenshots.

Instead of spending time curating a collection of screenshots, he could have shared his screen and scrolled through the data and examples he wanted them to see.

Clients prefer seeing actual pages and tools, instead of a manicured of screenshots. It's more authentic.

When I pitch GrowthAssistant, my offshore marketing company, I make a point of screensharing my Slack and showing clients how I work with the assistants I hire. When they see how I use my own service, they're sold.

Next time you sell, look for opportunities to share your screen, instead of a deck.

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