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.

I have a rule in my house: if my kids ask to buy a book, I just buy it on Amazon.

Why would I ever say no to a book?

But here's what broke my brain:

Most kids in Honduras don't own a single book. Not one. They share textbooks in school with 2-3 other students.

Their first personal book? Middle school or high school. IF their family can afford it.

When Sara Brakhane  (my CTO’s wife) told me that, I couldn't stop thinking about it.

So I built a library. Cost only $20,000. Done in 2 months. Now 600+ kids have access to books for the first time.

Kids in Honduras should have the same access to books as my kids do.

I want to build another with a few of my friends. 

Want to join us? I’ll match as much or as little as you donate, up to $10k. 

Comment “books” and I’ll DM you my plan.

Jesse Pujji

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

Two Teenagers pitched 100+ VCs with no success.

The crazy part?

Today the company is worth over $40B and they have full control. 

You've used the app. This is the story you need to know.

At 19, Melanie Perkins was teaching graphic design during college.

She wanted simple software to make graphic design easier.

To start, she built it for a use case she knew well: yearbooks

She and her boyfriend, Cliff Obrecht, invested everything they had plus a loan to launch.

They launched Fusion Books in early 2007 out of her mom's house.

They kept their jobs and invested $1000s in a school expo in Sydney...

It was a TOTAL WASTE.

The product was good, but they failed at growth.

Eventually, they picked up the phone and called schools directly.

It worked!

So Cliff kept calling schools.

The company became so successful, Melanie dropped out. 

They entered a startup competition.

Fusion Books came in 2nd at the WA Inventor of the Year competition in 2008. 

But still needed capital...

Bill Tai, VC superstar had flown in to speak.

He was the first investor they'd met. They got his card, and an offer to meet in SF.

Melanie emailed Bill several times, but got no response.

Last ditch, she said she was coming into town...

He said he could meet!

Panicked, Melanie booked her flight and started working on a pitch deck...

It was 2010, and she brought a printed pitch deck. He expected one on iPhone or tablet.

Bill had been on his phone the entire meeting.

Melanie thought he was bored.

In reality, he was sending intros for her the whole time!

She was onto something, but Bill wouldn't invest without a top tech team.

A classic Catch-22.

2010, Fusion Books grew to $2MM a year with 50% margins.

Funding was still years away.

In 2011, Perkins and Obrecht met their tech co-founder in Cameron Adams, a former Google lead designer.

It took another dozen pitches and over a year before he left his team to join them.

Tech team secured, Fusion Books pitched 100+ VCs.

Everyone turned them down.

They needed a better name. They tried Canvas Chef. Everyone hated it.

A new team member recommended “Canva” - Canvas in French.

The renamed team returned to Bill.

He offered $25k to open their round.

Melanie got him up to $100k.

Canva raised $3M for its seed round in 2012.

$1.5M from investors, with a match from the Australian government to keep them from leaving.

Now it was time to take on Microsoft, Adobe, Google, and Apple.

Canva reinvented online design with its drag n drop interface as Fusion Books years ago, but it didn't make waves until the general use application years later in 2013

They reached 50k users in their first month. 1M by 2014.

Their blog amplified growth. 

Canva built an inbound engine (SEO + content) that still works.

Canva is a 2025 IPO candidate, with an expected valuation of over $42 BILLION.

Melanie and Cliff got married in Jan 2021 with a $30 engagement ring. Together, they're worth $11.5B.

(28) LinkedIn

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Talks about #startups, #bootstrapping, #growthmarketing, and #entrepreneurship

The most ignored button on LinkedIn built my $20M business. 
97% of people are scrolling past $$$ right now. 

It took me months to crack how to find qualified leads in the wild. 
And it will take you minutes to copy 👇

Every time you post, LinkedIn’s AI-powered reasoning engine scans your network: who they are, what they care about, what they stop to read. 

That decides exactly WHO is engaging with your next post. 

I played my cards right- now that person is always my next customer. 

Here’s the 3-step cheat sheet to use CONNECTION REQUESTS as your next sales funnel:

1/ Engage with your leads before you connect
Once you know your qualified leads, take the time to engage with them. 

My GA maintains a Google Sheet with 400+ qualified LinkedIn leads. The sheet updates automatically whenever leads post new content. 

I like and comment meaningfully on those posts so my name keeps showing up on their notifications. 

By the time I do outreach, they’ve seen my name, and cold outreach feels more like a warm invite. 

2/ Add a short note
This is where most marketers fail. 
Don’t overthink it. The best messages are human, and personal. 

Steal these examples: 

“Hey [Name], I’ve really enjoy your content on [topic]. I’m in your field too, would love to connect!”

“Loved your post on [pain point]. We actually work with a few teams with the same challenges, would love to stay in touch.” 

“I saw you’re connected with [mutual connection]! I know them from [topic] and would love to connect.” 

3/ Max out your weekly requests
LinkedIn caps most accounts at 100 requests per week.
It’s 100 chances to expand your active reach and bring those users into your funnel. 

I had a GrowthAssistant take this on: every day, 20 people. 
The outcome? A network that won’t stop growing. 

If you want digital marketing experts to take rote tasks like these off your plate, let’s talk. 

I’ve placed 1000+ GrowthAssistants with clients like Reddit, Shopify, Calm, and 150+ more. 

https://lnkd.in/gmHNXXSy

When I almost missed a flight, I emailed the airport director DIRECTLY about parking.

Next thing you know, she’s in my network.

Founders ask me “how I have so many contacts on Linkedin?”

I just… reach out.

Constantly.

Most of you are under-reaching out — too worried about being judged.

Let it go. Just start the conversation!

AI is amazing, but I still (happily) pay more for human-based agencies. These are the ones I trust:

Good Operator - Our outsourced finance team. Real-time P&L, cash flow forecasting, and fractional CFA let us focus on growth.

notus - LinkedIn experts. Refined my LinkedIn profile and helped me grow my reach strategically.

Ashley Graef Cote - The human editor behind our newsletters and other content. Keeps our writing sharp, value-driven, and on brand.

The Feed Media - Helped us grow our newsletter audience and create our first paid product.

Zabal Media - Recently redesigned GrowthAssistant’s website. Top-tier visuals.

Gursey | Schneider LLP - Handles our taxes. Reliable, hyper-personal, and proactive.

GrowthAssistant - Our secret weapon. Global talent powers our marketing, analytics, design for a fraction of the cost of US FTEs (and trusted by Ro, Calm, HubSpot and 200+ other brands).

I have a simple rule for all B2B founders I coach:

5 new business meetings per week. No matter what.

Recently, one CEO celebrated having five meetings!

I asked: "Are those 5 separate companies or 5 people at 1 company?"

He paused. All one company. BUT he said, its a huge deal, >$500k in ACV.

What I told him was what my first sales leader taught me…in every organization there's a lot of people who can say no, and there's very few people who can say yes.

Any ONE of those five stakeholders can kill the deal.

Is it bad? Not at all. It’s just risky to put all your eggs in one basket.

That's why the rule of 5 is meant for 5 separate NEW LOGOS. Not 5 meetings inside 1 account.

Sure, if it's a six-figure vs five-figure deal, you’ll spend more time on it. Big deals are big deals.

My advice was to have 4 other new logo meetings as well, i.e. count that client as only ONE meeting.

Bottom line: don’t let 1 complex deal become your whole pipeline, no matter how enticing.

At my first company, I made a mistake with my balance sheet:

I left way too much cash in the business.

I thought it was smart to leave a cash cushion and focus on investing in growth.

But here's what actually happened: that money sat idle, creating FEAR-based leadership instead of motivation.

The company was making millions and I was still paying myself $75k. The profits still felt like monopoly money.

Year after year, the balance sheet grew. 

Then it hit me:

In a profitable services business, you don’t actually use capital to grow the business. You’re not buying inventory or making a factory. You'll spend future P&L when you need to invest via expenses. So why let it just sit there?

With the help of a working capital line, we started doing distributions.

So, I learned this the hard way:

Take. The. Money. Out.

How would your life be different if you had half a million personally in the bank? Would you get on more planes to chase deals? Would it be easier to show your family why this work matters?

Healthy founders who enjoy the fruits of their labor lead healthier companies.

The cash sitting in your business account isn't making you safer... it's making you scared.

GrowthAssistant has closed ~$1M in business from leads that came from ChatGPT. Here's what's working right now for LLLM discovery:

One of our Growth Assistants has made SIX figures in revenue in 90 days optimizing his client's website for GEO.

We stole his playbook to implement in all my companies. 

You can use it too:

1/ Don’t copy-paste your SEO strategy

SEO specialists simply optimize for keywords, but GEO experts optimize for PROMPTS:

- This Growth Assistant uses Athena, a software that surfaces the exact prompts potential customers are asking their GPTs.
- This data is pulled into a dashboard with the niche’s exact prompts ranked by frequency.
- Questions from GPTs like “What is the best shoe for women over 50?” power the next blog content to show up on LLM search.

Make sure your team also calculates KD% - the keyword difficulty - for showing up on GPT search, so you spend where you’ll see the most return. 

2/ Build a legitimate brand

SEO relied on backlinks to rank- GEO couldn’t care less about them. 

Instead, build an entity. 

After months, this brand realized that PR powered how much they appeared on GPT search: mentions in podcasts, listicles, roundups. 

The more legitimate the outlet, the more boost in LLM search. 

Shift your search strategy to thinking like your grandpa- what are the trusted outlets that would get him to buy? Invest in those and see the difference. 

3/ Super-localize everything

GEO supercharged this brand’s localized products. 

Why? Micro-level GEO is incredibly untapped. 

While most brands are preoccupied with macro-level GEO, this brand has quietly optimized to appear on hyperlocal prompts like “Best [X] for startups in Austin” or “Top [X] in Toronto for Series A.” 

They’ve optimized for Google My Business, citations, local directories, and local listicles 

The outcome: now, when someone asks an LLM a hyper-specific, local question, this brand is the obvious answer.

Every week, a Growth Assistant pulls the top 5 prompted questions in target locations, which powers content and PR to convert local leads. 

GrowthAssistant supports brands like Reddit, Calm, Ro, and 200+ more.

We're placing GEO experts to help your brand scale for < $3.5k a month. 

Get a free consultation:
https://lnkd.in/gK8THM8P

Every B2B founder has the same issue:

They UNDER sell: don’t plug their product enough, send too few emails and are generally afraid to promote.

It’s always the same reason:

They never want to come across like a “used car salesman.”

Here's my take…

Authenticity bridges the gap.

If all you are is salesy, it's really irritating for people and feels inauthentic.

But what if you're authentic and dynamic… If you show up as a real person who also happens to own a company?

I like to flip it: If you can really help people, why would YOU NOT plug your company? It makes no sense. It feels inauthentic NOT to be plugging it.

I'm passionate about my businesses. I started them. I believe in them. I think they can help prospects with their problems.

If you're one-note salesy, people tune out. But if selling is a natural extension of who you are and what you care about?

That builds trust.

Most founders are UNDER reaching out, not over. You're too worried about being judged.

Be authentic. Be passionate. And yeah... mention what you're building.

That's not being salesy. That's being real.

I coach founders to build unicorns.

Most founders I meet believe the same lie:

“If I stop beating myself up, I'll lose my edge.”

I asked one client: 'Are you willing to accept yourself and your startup exactly as you are right now?'

“Absolutely not,' he said. 'That's insane. What would motivate me?”

So we ran an experiment. I told him to do nothing for a week. Watch Netflix. Go to Vegas. Stop the self-criticism entirely.

He was terrified he'd become lazy and lose his creative drive.

By day six, he was bored. By day seven, he had three new business ideas and couldn't wait to get back to building.

Most entrepreneurs run on what I call 'dirty fuel' - fear, lack, and the story that they're not good enough yet.

But there's another way. Clean fuel: curiosity, vision, and the simple joy of creating something meaningful.

The founder who shifts from 'I have to' to 'I get to' doesn't work less. They work differently.

More creativity. Less burnout. Better decisions. Deeper impact.

The most successful leaders I know aren't driven by what they're running from.

They're pulled forward by what they're building toward.

Your creative energy won't disappear when you stop whipping yourself. It will finally have space to breathe.

I just met a super impressive kid my team hired without even asking me.

World-class recruitment has been the No. 1 enabler behind building 3 separate 8-figure businesses. 

Here are the 4 questions we ALWAYS ask:

1. What was your SAT/college GPA?

I believe academic achievement is a proxy for being able to do hard things. 

It’s one of the earliest predictors of acumen and rigor. 

And I get excited working with people who’ve been grinding towards a goal since their teens 
(I was that kid myself!) 

2. Why did you leave your last job?

"I got a better opportunity" explains why you went to the new company.

But why you LEFT is different.

Then I peel the onion more - What about the job before the last? And before that?

To my brain, it reveals patterns...

Was it always someone else's fault? 

That shows an inability to accept mistakes, not what I want.

Or do they jump ship every 2 years for a pay raise? I want lifers, not mercenaries.

3. Have you played any sports competitively?

Working at a growing startup is one of the hardest things you'll ever do.

I want people who've won, lost, learned, and pivoted. 

Many of my best hires are athletes: they know what it takes to persevere and win.

4. Have you ever experienced burnout?

The best people have burned out before.

And they know how to deal with it.

They can tell you the story without it being someone else's fault.

And they understand their missteps and EXACTLY what they need to avoid burning out.

➡️ One way to nail hiring is to use a trusted partner.

With GrowthAssistant, we embed offshore full-time team members to help with rote marketing tasks like reporting, design, etc. 100 companies trust us - companies like ClickUp, DoorDash, and Hubspot.

Done right, it's magic.

https://lnkd.in/gP2qqMhj

A few years ago, Jesse Pujji invited me to spend two days with his leadership team in a rented house overlooking Half Moon Bay.

They’d just survived a failed acquisition – exhausted, uncertain, and trying to rebuild trust.

That night, after dinner, I asked them to try something simple:

“Let’s go around the table,” I said. 

“Each person, ask for acknowledgment, and then give one in return.”

At first, the room froze.

People stared at their plates. One person laughed nervously.

Thirty minutes passed before the first real moment of honesty. 

Jesse later told me he wanted me to stop…

…and it felt unbearable.

But then something shifted.

In round two, they stopped performing and started seeing each other.

“John, I want to acknowledge you for keeping the New York office alive.”

“Katarina, you’re a new mom and still showing up as our CFO. That’s incredible.”

Two hours later, everyone was crying.

The tension had dissolved into connection. 

They weren’t just a team anymore… they were human again.

Here’s what I’ve learned: most leaders are more afraid of joy and intimacy than of fear or anger.

We say we want appreciation, but when it comes, we dodge it because we are afraid it’ll make us soft.

But acknowledgement isn’t weakness…

It’s fuel.

Because what you appreciate, appreciates.

A hacker almost stole $25K+ from my e-com brand in one week. 

Most brands would’ve missed it and lost MORE…

My $5M ARR brand Unbloat runs thousands of dollars in daily Meta spend.

Two weeks ago, our digital marketing GrowthAssistant slacked us a message that sent me into panic mode:

“Meta spend just spiked +$2K. I paused all campaigns.”

I was convinced Meta changed the algorithm again. When I built Ampush, I saw Meta burn ad spend on a whim, time and time again.  

The truth was even worse: 

A hacker. Quietly torching our ad spend just for fun. 

And catching that hijacker didn’t just save ad budget. It protected:

- Our #1 lead channel
- Years of A/B testing data
- Invaluable customer trust (gold for our subscription brand)

My favorite part?

She spotted the activity using an hourly ad spend tracker she built on her own.

She’d spent months as part of a lean team (one US manager, one other GA) and learned one simple rule:

In performance marketing, anomaly detection = dollars.

So she created this simple, 3-step framework to catch all ad bleed (and hackers). 

1️⃣ Track ad spend hourly (by account + campaign).

2️⃣ Trigger Slack alerts for any spike >X% vs. hourly norm.

3️⃣ Shut campaigns down fast when something looks off.

#3 terrifies most marketers, frightened of letting someone else handle spend. 

That fear would’ve let the hacker burn $10-25K. 

Catching anomalies like these BEFORE they cost you has no price tag. That’s why I’m embedding GrowthAssistants into e-com teams like mine every day. 

They’re catching issues like this and saving brands like Calm, DoorDash, HubSpot and 200+ more real money — at a fraction of the cost of a US FTE.

Global experts in marketing, analytics, design, and ops.

https://lnkd.in/gBMs5edw

Here's how we stopped a problem from becoming a disaster

𝐒𝐡𝐨𝐩𝐩𝐢𝐧𝐠 𝐟𝐮𝐧𝐧𝐞𝐥𝐬 𝐚𝐫𝐞 𝐜𝐨𝐥𝐥𝐚𝐩𝐬𝐢𝐧𝐠. Have you seen ChatGPT’s new Shopping Research feature?

It’s the first real case of search-level intent and social-level relevance in the same place.

If that holds, expect the economics to shift fast: higher CTRs, higher CVRs, and far less leakage between steps.

My team talks to dozens of marketing leaders a week who are all making the same mistake. It’s so simple you’ll laugh when you hear it:

Not focusing on conversion rate optimization. 

The reason is always the same:
”We’d love to do more CRO, but we don’t have the time or resources.” 

If your marketing team is spending all their time on media plans, content, campaigns etc they’re missing a key driver.

Last week, we placed a GrowthAssistant with a global digital brand spending $50M+ on ads. 

They were running Meta campaigns at scale but all traffic was going to the exact same place.

Not thinking about the post click user experience means you waste every dollar spent on traffic.

No surprise: good leads weren’t converting because the funnel was not built out.  

In two weeks, their GA: 

- Set up a sub domain for meta traffic experimentation
- Built a new LP frame from scratch to test feedback and iterate
- Designed and executed A/B tests on the landing page and pdp

Within 8 weeks, their ads were yielding 18% more conversion THE SAME SPEND. 

Everyday, GrowthAssistant places elite global talent like this across marketing, influencer, data, design, and more. 200+ companies like DoorDash, HubSpot, Reddit, Shopify, etc. are customers.

If you’re tired of flying blind, let’s talk about building the system that never stops watching. 

Start scaling for a fraction of the cost of US FTEs:
https://lnkd.in/g6rChHX5

Bridging the Gap Between PE and Marketing | Founder Aux Insights | I provide clear, actionable plans for portcos

I get asked a lot about how I stay present as a CEO and a mom. Honestly, I’m still figuring it out. We’re all getting hit with so much every day (news, finances, the world feeling uncertain) and it’s really easy to spiral. Your mind jumps to: Are we okay? Are our kids okay? Is the company okay? What do we do about all of this?

And then sometimes something simple pulls you back.

Last Saturday a friend texted, “It’s 80°. Want to get pizza outside and let the kids play before Dave’s show?”

We went. 

The night was perfect: warm air, string lights, friends talking, kids running around.

The conversation drifted into stressful topics a few times, as it does, but then I looked around and thought: This is a good moment.

So I’ve started doing this thing (it sounds silly) where I pretend I’m clicking a disposable camera in my mind.

A big click. Almost like I’m telling myself: remember this.

Because when everything feels heavy, I want these moments to be right there for me too.

Click: laughing so hard at one of Dave’s stories that I’m crying.

Click: sitting at dinner with Mish after a long conference day, watching her light up talking about a project.

Click: my team celebrating after closing a huge deal for the first time.

Click: my son running down the stairs in the morning and giving me that huge hug.

Click: my daughter repeating back something I told her, and I can see she really heard it.

My mind moves a million miles an hour. I’m always building, planning, thinking about what’s next.

But being present, at least for me, is about catching those moments when they happen, noticing them, and saving them.

Click.

The outreach and suppprt for this has been incredible! Please donate and reach out to chispa. Maybe we can do 2-3 libraries!

Co-founder of Bootstrapped Giants | Helping digital agencies create a repeatable sales process | Built and sold a $38M/yr start-up with no funding | Host of Mixergy

I’m starting a new AI podcast series, and I’m afraid.

I’ll list all my fears publicly to get them out of my system (hopefully).

1. I’m afraid I’m too late to cover AI.

2. I’m afraid others are doing AI interviews well already. Lenny & Dan Shipper & Greg Isenberg rock at this.

3. I’m afraid of posting on a new YouTube channel, where my low subscriber count will look pathetic.

4. I’m afraid I don’t know enough about AI to even ask the right questions.

5. I’m afraid that getting attention for these interviews will require me to promote on social media and I hate social media. (It lacks depth.)

6. I’m afraid I have limiting beliefs that I’m not aware of, like that whole social media thing I just wrote above.

7. I’m afraid that building a human-based podcast today is like launching a radio show in 2020. (AI-generated podcasts will take over. Humans will be passé.)

8. I’m afraid of my new excitement for editing. It’s making me a perfectionist, which is keeping me from publishing fast enough.

9. I’m afraid that, by the time I publish anything, it’ll be dated.

10. I’m afraid that I won’t push hard enough because my life is too comfortable.

11. I’m afraid that my team assumes I’ll be great because of my experience, and I’ll let them down by sucking.

12. I’m afraid you’ll try it and think you were wrong to have ever liked my past interviews.

13. I’m afraid that years of challenging my guests too forcefully gave me a “stay away from that interviewer” reputation.

14. I’m afraid I won’t stick with it. And if I promote it, I’ll just make it that much more painful if I quit.

I started publishing last week.

I’ll share the platform I’m most afraid of showing up on because I’m also excited about how it came out:

https://lnkd.in/g27MJU6k

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