He Generated $48M in 18 Months & Exited 3 Businesses (Jesse Stein Story)

TLDR: Acquiring underpriced attention at scale

Jesse Stein built three businesses by mastering what he calls "acquiring underpriced attention at scale," including an AI agent that converts leads in 13 seconds compared to the 48-hour industry average. His systematic approach to customer acquisition eliminated the trial-and-error that consumes most growth teams.

Listen to this episode to learn how Jesse's 20-year-old SEO tactics still rank #1 for major keywords, why ChatGPT places irrational emphasis on directory listings most teams ignore, and the hiring practice that has him flying across the country to meet every key candidate before making an offer.

Meet the guest: Jesse Stein, serial entrepreneur and founder of Hermetic.ai

Jesse Stein is a serial entrepreneur who scaled a media arbitrage operation to $28 million before selling to Insight Ventures, sold $48 million worth of products in 18 months through pure affiliate marketing, and built a sports memorabilia site that still ranks #1 or #2 for major keywords two decades later.

Jesse brings VP of Sales experience from scaling companies to multi-million ARR, plus deep expertise in SEO, customer acquisition, and market positioning. His current venture, Hermetic.ai, deploys AI agents for hospitality private events that engage leads within 13 seconds of form submission, compared to the industry average response time of 48 hours.

Chapters

[00:42] Born to hippie parents in San Francisco: How the summer of love shaped Jesse's entrepreneurial foundation

[11:38] The media arbitrage goldmine: How Jesse scaled to $28M by buying clicks cheap and selling conversions expensive

[16:54] SEO tactics that still work 20 years later: Link disavows, page pruning, and why ChatGPT obsesses over directories

[25:23] The flying-to-close hiring hack: Why Jesse meets every key hire in person before extending offers

[28:32] Following pioneers instead of being one: Why success leaves clues you can trace and copy

[32:03] Hermetic.ai genesis: Why hospitality private events became the perfect AI agent opportunity

[40:30] The Grand Canyon principle: How focus creates deeper competitive moats than horizontal expansion

[46:13] Co-founder chemistry: How Jesse finds technical partners through equity generosity

[47:15] YPO and pull motivation: How networking with inspiring people creates sustainable drive

Key Insights

Six years of door-to-door sales in Japan taught Jesse the rejection frameworks that powered his customer acquisition success.

Jesse spent six years knocking on doors in Tokyo selling HR services to small companies, learning to handle rejection in a foreign language while wearing a company suit. His boss once made him continue sales calls during a typhoon, forcing him to ring out his soaked suit in the bathroom between appointments. "It was very humbling, but it really taught me how to deal with rejection because there was a lot of rejection," Jesse explains.

This systematic exposure to rejection at scale taught him how to adapt messaging to unfamiliar audiences and persist without emotional friction, lessons that translate directly to modern outbound execution.

Most SaaS companies waste months pioneering unproven tactics when competitive intelligence reveals exactly what works at scale.

Success leaves clues for almost anything. Google wasn't the first search engine; it was the 23rd. Apple didn't invent the smartphone. These companies succeeded by following pioneers who had "arrows in their back" and improving on existing solutions. "Don't be a pioneer. Being a pioneer is the slow boat," Jesse notes.

Modern SaaS teams have unprecedented access to competitive intelligence through Facebook Ad Library, Archive.org, SemRush, and Ahrefs. This eliminates the need to build strategies from scratch. Jesse's media arbitrage business succeeded by finding underpriced clicks on emerging platforms and selling them to established advertisers at higher CPAs.

ChatGPT places irrational emphasis on directory listings, creating massive AI SEO opportunities most growth teams ignore.

While traditional SEO tactics still matter, Jesse discovered that ChatGPT heavily weights directory inclusion when ranking websites in AI search results. "For some reason, ChatGPT places a really high and irrational emphasis on having your site included in directories, any directory at all," Jesse explains.

This happens because directories contain structured data that AI can crawl easily. The tactical playbook involves submitting queries your ICP would ask ChatGPT, documenting who appears in results, then identifying the directories that consistently surface. As we discuss in the episode, SaaS companies with strong directory presence can outrank major authorities like Mayo Clinic in AI search results. At Understory, we see this as reminiscent of SEO in the late 90s and early 2000s where small hacks created outsized results before the window closed.

Jesse's 20-year-old domain still ranks #1 or #2 for major keywords because of systematic SEO implementation most agencies don't execute.

The competitive moat came from systematic tactics executed consistently over years. Jesse hired someone in South Africa whose sole focus was link disavows, identifying spammy websites linking to their domain and formally disavowing them to Google monthly. Monthly page pruning involved analyzing Google Analytics for low-traffic pages and 301-redirecting them to category pages, concentrating page rank into fewer, higher-authority pages.

The content operation scaled through 150 freelancers producing 25,000 articles, but the real differentiator was sophisticated technical SEO that competitors couldn't easily reverse-engineer.

Flying to meet key hires face-to-face before making offers prevents the cultural mismatches that create coordination overhead later.

Most companies hire remotely and discover cultural mismatches when coordination breaks down months later. Jesse learned from mentor Bob Davis to fly anywhere for final-round candidates and spend full days together before extending offers. "Let's agree that before I leave Austin, Texas or New York City or wherever they are, that we'll come to that agreement before I leave," Jesse explains.

When hiring Hermetic's Chief Product Officer, Jesse "started with 605 people, engaged with 59, interviewed 22." This systematic approach ensures cultural alignment before problems emerge.

Jesse tested 8,000 outbound calls across multiple industries before finding hospitality, demonstrating how proper ICP validation eliminates wasted effort.

Before building Hermetic's AI agent, Jesse's team systematically tested different industries rather than assuming their solution would work everywhere. SaaS companies were "a messy alphabet soup of vendors" where breaking through proved difficult. Home services came next, but the workflows weren't complex enough to justify an AI solution.

Through systematic outbound testing, hospitality revealed itself as the perfect fit. "We could really feel the pain" when talking to hotel and restaurant private event coordinators. This prevented Jesse from building solutions in search of problems. At Understory, we apply similar validation rigor through Clay-powered outbound before scaling campaigns, ensuring ICP fit before investing in full execution.

Outbound should be measured as an influenced pipeline, not just direct responses.

As we discuss in the episode, most companies misunderstand outbound by only tracking direct replies. At Understory, we see this constantly: 2,000 emails might generate 20 direct responses, but teams miss the prospects who visit the website after receiving outreach and convert through retargeting or other touchpoints.

The fix requires treating outbound as a hyper-targeted ad campaign rather than a siloed sales activity. Outbound hits the exact person with personalized messaging, making it more precise than most ad platforms. When paid media and outbound work together, the combined attribution reveals true campaign performance that neither channel shows alone.

Mia, Hermetic's AI agent, converts private event inquiries within 13 seconds compared to the industry average of 48 hours.

The hospitality industry loses 80 to 90% of private event business to whoever responds first, but most venues take two days to respond to website inquiries. Jesse audited 500 different forms and found this consistent pattern: "Even during business hours, if you submitted that at 3 p.m. on a Tuesday, you're gonna hear back by the afternoon on average on Thursday."

Mia engages leads within 13 seconds with personalized text messages that get responded to almost 100% of the time. Venues using Mia see 2.5x more opportunities for event coordinators to close.

The Grand Canyon principle: focus creates deeper competitive moats than horizontal expansion.

Every successful company faces pressure to expand into adjacent markets. Jesse learned this lesson after the temptation to apply Hermetic's technology across multiple industries nearly derailed his focus. "The Grand Canyon is majestic because the Colorado River is narrow. Because the Colorado River is narrow, the water has force," Jesse explains.

When you focus completely on a single ICP, "they feel like the solution fits like a glove just for them." This makes it impossible for horizontal competitors to match depth of domain expertise, feature specificity, and workflow integration.

Social engagement data converts into hyper-targeted paid media audiences that outperform traditional targeting.

As we discuss in the episode, at Understory we discovered this cross-channel opportunity when working with social signal tools like Trigify. Prospects actively engaging with relevant content across platforms can be exported directly into LinkedIn matched audiences, creating micro-ABM campaigns targeting people who've already demonstrated interest in specific topics.

These social-signal-derived audiences consistently deliver superior efficiency compared to standard LinkedIn demographic targeting because they're built on actual behavioral signals rather than static profile attributes. This approach exemplifies coordinated allbound execution where social intelligence directly informs paid media strategy.

Want more insights on customer acquisition and AI automation? Listen to the full episode on YouTube and subscribe to Understory's podcast for more conversations with SaaS growth leaders.

Looking to coordinate your paid media and outbound execution without specialist management overhead? Book a call with Understory to explore how expert allbound execution eliminates vendor coordination and lets you focus on strategic growth decisions.