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My First MillionJesse Pujji on Bootstrapping a +$1B Business + Selling To The Ultra Rich
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CHAPTERS
- 0:00 – 3:14
Aux Insights: Marketing Diligence for Private Equity
Jesse explains how friends in private equity kept calling him with questions about digital ads, which led him to launch Aux Insights, a consulting business for PE firms. It covers marketing due diligence and post-purchase value creation, and compares it to Accordion's finance work and McKinsey's PE practice.
- •Friends at firms like Blackstone and TPG kept asking Jesse how to judge a target's Google and Facebook ads
- •A fourth friend asked him to do the work for a couple hundred thousand dollars
- •Aux serves the office of the CMO, with diligence before a deal and value creation after
- •Accordion (finance) and LEK are cited as large, high-margin PE-focused consultancies
- 3:14 – 6:03
Starving Crowds, Rich Customers and GatewayX
Shaan frames the lesson of selling to rich, rational, price-insensitive buyers rather than broke ones. Sam gives background on Ampush and GatewayX, and Jesse explains the studio's rule of needing a unique insight and an unfair advantage.
- •Shaan contrasts working backwards from rich customers with starting from cool ideas aimed at other broke people
- •PE and hedge funds are urgent and rational rather than price sensitive
- •Jesse sold Ampush, then started GatewayX, a studio and holdco with six businesses started and two shut down
- •Each studio business needs a unique insight and an unfair advantage
- 6:03 – 8:52
Why Kahani Failed and Growth Assistant Worked
Jesse describes Kahani, a plugin that made e-commerce sites look like Instagram and TikTok. People thought it was cool but it solved no real problem. A trade show comparison with Growth Assistant showed the gap between a cool idea and a real need.
- •Kahani's first product was a stories navigation bar plugin for e-commerce sites
- •Customers removed it, citing doubts about conversion and slower sites
- •At Shoptalk, the Kahani sales rep got 3 meetings and the Growth Assistant rep got 25
- •Shaan invested in Aux almost instantly from a text, but passed on Kahani
- 8:52 – 12:04
Bootstrapping Ampush with GLG Expert Calls
Jesse tells how he used GLG, the expert network, both at Goldman and later as an expert himself. That led to selling $5,000 research reports to hedge fund people and raising about $150,000 for Ampush.
- •At Goldman he used the firm's unlimited GLG access to research his future business during a 90-day wind-down
- •As an Ampush expert he charged $500 an hour for calls
- •A caller asked for research, and he sold a $5,000 report that grew to 30 sales
- •He jokes that the report sales were Ampush's angels round
- 12:04 – 14:17
Pricing Lessons and Aux's Pricing and Value Proposition
After a sponsor break, Shaan shares the CB Insights story of raising prices on a PDF. Jesse explains Aux's pricing against McKinsey, Bain and BCG, and why PE clients want marketing translated into revenue and EBITDA terms.
- •CB Insights raised prices on its PDF after advice to charge far more
- •Aux charges $50,000 a week versus $200,000 a week for McKinsey, Bain and BCG
- •Big consultancies aren't marketing practitioners, and agencies speak in jargon
- •Aux translates marketing levers into revenue and EBITDA
- •Value creation engagements run experiments, while diligence takes about four weeks
- 14:17 – 20:36
How Aux Grades a Business and Why PE Buyers Hire It
Jesse walks through what Aux assesses, such as top-down benchmarks, account structure, event match quality and creative testing volume. He shows the internal tool and explains the human motivations of PE partners, while sharing results from about 20 projects.
- •Top-down benchmarks cover click-through and conversion rates, and bottom-up checks cover account structure and match quality
- •Creative testing volume is one of the easiest levers
- •The first slides give a grade per channel and an EBITDA waterfall
- •Shaan says buyers are paying for certainty and cover
- •Aux has told buyers to stay away on about 25% of projects, including one case of SEO backlinking fraud
- 20:36 – 27:12
Selling Information to the Ultra Rich: First Rain and Hedge Fund Data
Shaan asks about other businesses that sell to ultra-rich customers. Jesse discusses Bloomberg, First Rain's costly alerts tool, and his $5 million loan from a hedge fund contact in exchange for Facebook data, and pitches a quarterly ad-spend survey data product.
- •Bloomberg is described as the richest man in New York, selling information
- •First Rain was effectively Google Alerts at around $50,000 a month
- •A hedge fund friend gave Ampush a $5 million interest-free loan for aggregate Facebook data
- •Jesse and Shaan float selling ad-spend survey data to hedge funds, possibly via a reverse auction
- •The takeaway is to add a zero to prices and pair what you know with what the rich need
- 27:12 – 32:52
Red Ventures: History and Culture
Sam asks about Red Ventures, and Jesse recounts its founding, its pivot into DirecTV lead generation, and its growth into acquiring SEO content businesses like Bankrate. He also describes its distinctive, numbers-driven culture.
- •Red Ventures built a $75 million EBITDA business selling DirecTV subscriptions online
- •It expanded to credit cards and other high-LTV purchases, then bought SEO content assets
- •It bought Bankrate, tripled its EBITDA, and later bought Healthline and CNET
- •Meetings are short, start with the bottom line, and teams are organized around KPIs
- •It has never raised primary capital
- 32:52 – 39:02
Red Ventures' Four Big Levers
Jesse lays out the four levers Red Ventures pulls after acquiring a business. They are traffic acquisition, onsite optimization, pricing to willingness to pay, and lean headcount.
- •Traffic acquisition covers paid and organic, with a focus on cost and revenue per visitor
- •Onsite optimization places offers smartly without being too salesy
- •Pricing to willingness to pay: after closing Bankrate, a leader dropped the bidding algorithm and got 20% more EBITDA
- •Headcount cuts included a draft where managers picked who stays
- 39:02 – 41:48
Roll-Ups and Multiple Arbitrage for Profitable Founders
Sam asks why every profitable founder should understand PE and roll-ups. Jesse uses the Elite SEM example to show how buying small businesses and selling the combined entity at a higher multiple creates value, and mentions AI-enabled roll-ups.
- •Elite SEM was sold to Mountain Gate Capital, which added six businesses at lower multiples
- •The combined business later sold for 15 times EBITDA
- •Multiples rise with growth, stability, margin and defensibility, which improve with scale
- •Jesse sees roll-ups as better than the venture path for bootstrapped founders
- •He mentions buying a creative agency and rebuilding it with AI
- 41:48 – 46:00
Calling Zuckerberg's Cell: The High List
Jesse tells how his college team built a high school Facebook clone called The High List. He called Zuckerberg's cell pretending to be a partner and heard Facebook's whole expansion plan.
- •In 2005 they built The High List after failing to buy hsfacebook.com for $20,000
- •The domain owner said Zuckerberg wanted to buy it and forwarded his email
- •Jesse called Zuck posing as Tom Goldberg
- •Zuck laid out the whole strategy, and Facebook crushed their plan
- 46:00 – 50:51
Early Facebook Equity Math and Noah Kagan's Mistake
The group discusses what joining Facebook early would have been worth. Sam tells how Noah Kagan was fired three months before vesting, and Shaan runs the math on a junior employee's stock and on picking winners.
- •Jesse says a friend's Facebook offer would have been worth $75 million
- •Sam says Noah Kagan was fired after talking to a reporter, three months before his first vest
- •Shaan estimates even a junior hire's stock could have grown to about $54 million
- •Shaan says picking the right company beats hard work, but few would actually hold the stock
- 50:51 – 1:01:10
Money, Fulfillment and Finding What You Can't Not Do
The conversation moves to the pay at Goldman, whether huge wealth makes people happy, and what a good life looks like. Jesse shares the coaching exercise of identifying the one thing you can't not do and how it shapes his work.
- •Jesse left Goldman after seeing what the senior path looked like
- •Lucky wealth can leave people feeling like frauds, while founders know they earned it
- •Shaan describes asking who is having the most fun, using Joe Rogan as an example
- •Jesse's coach asked, "What's the one thing you can't not do?"
- •Jesse now organizes his to-do list around helping people rather than businesses
- 1:01:10 – 1:07:13
Getting Nelly to Perform at Jesse's 40th Birthday
Jesse tells how he got Nelly to perform at his 40th birthday in St. Louis. He built a relationship with Nelly's team by helping with their e-commerce work, then paid for a private jet.
- •Nelly's quoted price started at $300,000 and could reach half a million
- •Jesse got introduced to Nelly's people through St. Louis contacts and helped with their e-commerce projects
- •Scheduling conflicts were solved by flying Nelly on a G4 round trip for $60,000
- •Nelly played a 45-minute set, and Jesse called it a top-three life moment
