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August 26, 2024 • 1hr 10min
Bootstrapping a +$1B Business + Selling To The Ultra Rich | Jesse Pujji
My First Million
In this episode, Sam Parr and Shaan Puri interview Jesse Pujji, co-founder of Ampush and Gateway X. Jesse shares insights from his entrepreneurial journey, including how he bootstrapped Ampush into a major digital marketing agency, his experiences working with companies like Red Ventures, and his current focus on building a portfolio of profitable businesses through Gateway X. The conversation covers a wide range of business topics, from identifying lucrative markets to executing roll-up strategies.
Bootstrapping a +$1B Business + Selling To The Ultra Rich | Jesse Pujji
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Key Takeaways
- Find the starving crowd first - It's easier to succeed in business if you identify a hungry market with urgent needs before developing a product or service
- Sell to the ultra-wealthy - Businesses that cater to hedge funds, private equity firms, and other wealthy clients can charge premium prices and scale quickly
- Leverage unique insights and unfair advantages - The most successful businesses combine deep domain expertise with some unfair advantage or insider knowledge
- Private equity roll-ups can create massive value - Buying and consolidating smaller companies in a fragmented industry can lead to multiple expansion and huge returns
- Focus on what energizes you long-term - True success comes from building a business and life around the work that you find most fulfilling, not just chasing money
Introduction
In this episode, Sam Parr and Shaan Puri interview Jesse Pujji, co-founder of Ampush and Gateway X. Jesse shares insights from his entrepreneurial journey, including how he bootstrapped Ampush into a major digital marketing agency, his experiences working with companies like Red Ventures, and his current focus on building a portfolio of profitable businesses through Gateway X. The conversation covers a wide range of business topics, from identifying lucrative markets to executing roll-up strategies.
Topics Discussed
Bootstrapping Ampush Using GLG (3:05)
Jesse shares the fascinating origin story of how he bootstrapped Ampush, his digital marketing agency:
- While working at Goldman Sachs, Jesse and his co-founder used the firm's GLG (expert network) subscription to research digital marketing trends
- After leaving Goldman, they signed up as GLG experts themselves, charging $500/hour for calls
- A hedge fund client asked if they had a research report, so they quickly put together a 50-page report on the lead gen industry and sold it for $5,000
- They ended up selling 30 copies of the report, raising $150,000 in "angel funding" to bootstrap Ampush
"So I always joked that was Ampush's angel round. We raised $150,000 selling research reports to hedge fund people." - Jesse Pujji
Digital Marketing Masterclass in 3 Minutes (14:00)
Jesse provides a rapid-fire overview of key digital marketing concepts:
- Top-down analysis - Use industry benchmarks to assess performance
- Bottom-up analysis - Evaluate account structure, event match quality, creative testing cadence
- Creative testing is one of the easiest levers to improve performance
- Event match quality is critical - many companies have poor data quality which hampers performance
"The easiest thing - someone says my performance is bad, I'll go, how many creatives do you test a week? A week? What are you talking about? Oh, we do two a month. Well, yeah, of course your performance is going to be horrible, right?" - Jesse Pujji
How to Sell to the Ultra Rich (20:30)
Jesse discusses strategies for selling high-priced services to wealthy clients like hedge funds and private equity firms:
- They are not price sensitive if you can demonstrate clear ROI
- Leverage unique data or insights they can't get elsewhere
- Understand their psychology - they often want certainty and risk mitigation
- Build relationships and prove your value over time
"Because of the numbers they're dealing in, they can just pay anything, right? Just like the $200,000 to diligence the project for a half a billion dollar deal. It's nothing for them." - Jesse Pujji
Red Ventures' Playbook (27:38)
Jesse provides an inside look at Red Ventures, a highly successful digital marketing and technology company:
- Started in 2000, struggled for first 5 years before finding success with Google AdWords
- Built a $75 million EBITDA business selling DirecTV subscriptions online
- Expanded to other high LTV verticals like credit cards, wireless plans, etc.
- In recent years, pivoted to acquiring content/SEO assets like Bankrate, CNET, Healthline
- Unique culture blending "Wall Street trading desk, southern politeness, and hard-nosed direct response marketing"
"They basically took their [digital marketing] playbook, and now the services part of their business is a tiny part of their business and the SEO content part is a massive part of their business. But the same culture, the same playbook." - Jesse Pujji
The Four Big Levers (32:40)
Jesse outlines the four key levers Red Ventures uses to dramatically improve the businesses they acquire:
- Traffic acquisition - Optimize paid and organic channels
- On-site optimization - Improve conversion rates and monetization
- Pricing optimization - Maximize revenue per customer
- Cost reduction - Streamline operations and reduce headcount
"They're very good at truly challenging the bloat in an organization and being like, how many people do we actually need?" - Jesse Pujji
Calling Zuck's Cell (41:00)
Jesse shares a hilarious story from his college days:
- In 2005, Jesse and friends were building a "high school Facebook" competitor
- They tried to buy HSFacebook.com but the owner said Zuckerberg wanted to buy it
- Jesse called the phone number provided, pretending to be a co-owner
- Zuckerberg spent 30 minutes outlining Facebook's entire expansion strategy
- Jesse's high school Facebook plan failed when Facebook expanded to high schools
"He spends 30 minutes and to his credit, he outlines the entire strategy that Facebook has executed. He goes, first we're gonna go to high schools, then we're gonna go to workplaces, then we're gonna go into pods..." - Jesse Pujji
Noah Kagan's $100M Mistake at Facebook (46:30)
The hosts discuss Noah Kagan's infamous firing from Facebook:
- Noah was employee #30 at Facebook
- At a party, he drunkenly leaked product plans to a TechCrunch reporter
- Zuckerberg fired him 3 months before his first stock vest
- Those unvested shares would be worth ~$100 million today
"Noah told me, he goes, had I just made it that three months, those shares today would be worth about $100 million." - Sam Parr
What's the Thing You Can't Not Do? (58:45)
Jesse shares a powerful framework for finding your purpose:
- Ask yourself: "What's the one thing you can't not do?"
- What naturally comes into the room with you?
- For Jesse, it's helping others reach their full potential
- He now structures his to-do list and businesses around this purpose
"We try to make purpose this far out thing we have to go get. And it's actually the thing already inside of us that we just need to tap into and live more fully." - Jesse Pujji
Nelly Performs at Jesse's Birthday Party (1:01:00)
Jesse tells an amazing story about getting Nelly to perform at his 40th birthday:
- Initially quoted $300k-$500k through normal channels
- Jesse networked his way to Nelly's team and offered free e-commerce consulting
- Built a relationship over time and eventually asked for the favor
- Arranged private jets to make the tight schedule work
- Nelly ended up doing a full 45-minute set
"It was scary because he wasn't under any contract with me. So he could have come out, said, hey, happy birthday, Jesse. E.I. And he could have left. He ends up doing a 45 minute set." - Jesse Pujji
Conclusion
This wide-ranging conversation with Jesse Pujji offers a wealth of insights for entrepreneurs and business leaders. Key themes include the importance of identifying lucrative markets, leveraging unique insights, and focusing on work that is intrinsically motivating. Jesse's stories - from bootstrapping Ampush to getting Nelly to perform at his birthday - demonstrate the power of creative problem-solving and relationship building. His current focus on building a portfolio of profitable businesses through Gateway X showcases an intriguing model for experienced entrepreneurs looking to have impact at scale while maintaining autonomy and work-life balance.