Market Gap Startups

Co-Fertility is a marketplace that bundles egg freezing with egg donation to solve the affordability problem in fertility services. By offering free egg freezing to women who agree to donate half their eggs, and charging $13,700 to recipients seeking eggs, the company creates a two-sided marketplace addressing a growing market (20,000 US women froze eggs in the prior year) with a controversial but strategic business model designed to generate earned media.

Pornhub was built by three Canadian college friends (Manos, Yusuf, Keaser) who leveraged YouTube's video hosting innovation to create a centralized adult content platform in 2007. The site grew from directory links to pirated content to becoming one of the top 6 most-trafficked websites in the US (2 billion visits/month) through exceptional SEO execution and organic growth, eventually reaching $100M+ in revenue before being sold multiple times to various owners including Fabian Tillman ($140M in 2010), and later to private equity.

Follow Up Boss is a vertical SaaS CRM built specifically for real estate agents to manage leads from platforms like Zillow and Redfin. Founded by Dan (from Australia, based in Wyoming) 12 years before exit, the company took 4 years to reach $100k MRR with just 11 employees, bootstrapped entirely through Facebook group engagement and word-of-mouth. The company sold for $500 million ($400M cash upfront + $100M earn-out), demonstrating the power of patient, niche-focused founder persistence and organic growth.

Sam Ratner dropped out of University of Missouri at 18 to build a mobile-first sports betting platform, recognizing that legalization would transform the U.S. gaming market. He built the company from credit cards and savings from a high school snow removal business, secured partnerships with the NBA and MLB as an authorized gaming operator, and sold the platform to Fubo TV for $40 million at age 23—before it even launched. Since then, he's explored numerous unconventional investments including purchasing a decommissioned riverboat casino and deeply analyzing a vending machine business.

Resi Club is a content-first platform focused on residential real estate coverage and data, co-founded by Anthony Pompliano and real estate expert Lance Lampard (former Fortune real estate editor). Launched just two months before this interview, the platform achieved profitability within the first month on a $100k initial investment and is positioned as the dominant voice in residential real estate commentary.

Moises Ali bootstrapped Native Deodorant from a kitchen table to a $100M exit to Procter & Gamble. He built the initial website in 3 days using WordPress and Woo Commerce, deliberately avoiding expensive design agencies. The brand grew through word-of-mouth and built a post-purchase upsell mechanism that generated $700k monthly in travel-size sales.

Blockworks is a crypto-native media and information company founded in December 2017 by Jason and co-founder Mike. Starting from cold LinkedIn outreach (300 messages/day), they bootstrapped to $25M+ revenue by building a media platform with podcasts, newsletters, conferences, and eventually a subscription research platform (Blockworks Research). The company scaled profitably from day one, with major conferences like Permissionless generating over $10M in revenue.

Brett Adcock founded Figure AI to build humanoid robots for commercial labor after selling his recruiting marketplace Vettery for $110 million and taking Archer Aviation (electric VTOL aircraft) public at a $1.5B valuation. He went all-in on Figure, nearly bankrupting himself personally while the company reached a $7M/month burn rate, ultimately betting that the humanoid robotics market could become one of the world's largest industries worth more than autonomous vehicles.

Spazless is a proposed nonprofit Reddit alternative that would operate similarly to Reddit but as a nonprofit that funnels revenue back to communities and moderators. The idea emerged during a major Reddit protest in 2023 when 93% of subreddits went dark to protest API pricing changes that would kill third-party apps like Apollo. The domain was registered as a conceptual project to capitalize on user discontent.

Sulamon Ali founded Tiny Co in 2009 to create mobile games for the newly launched iPhone App Store. Their first game, Tap Resort, generated $500-600K in revenue in its first month through a partnership with mobile ad network Tapjoy. After raising $18M from Andreessen Horowitz (with Mark Andreessen joining the board), they scaled to $20M revenue in year one and $40M in year two, but hit a wall when Japanese mobile gaming competitors drove customer acquisition costs from $1 to $9, destroying their unit economics and leading to significant monthly losses.

Cherry is a browser extension that helps accommodation businesses get direct bookings by showing customers better deals when they search on travel sites like Expedia and Booking.com. In four months, they onboarded nearly 1,000 partner properties across Australia, New Zealand, and Canada, with plans to launch in the US with 20,000 properties by November. They charge hotels a performance fee of $10/month plus $0.79 per click, significantly cheaper than the 30% commissions charged by major OTAs.

Zach Schachkeed built a mobile app version of the viral Wordle game over a weekend and achieved 30,000 organic downloads in just days, reaching the top of the App Store. However, his public celebration of this success on Twitter—despite previously tweeting against app clones—led to significant backlash from the tech community and ultimately resulted in Apple pulling all Wordle-branded apps from the store.

Storage Squad is a storage business built by Nick Huber that combines technical knowledge with a traditional, less competitive market. Huber champions what he calls "Sweaty Startups" - labor-intensive business models that he believes offer unique advantages and opportunities for entrepreneurs.

Hari Mari is a premium flip flop manufacturer co-founded by Jeremy Stewart and his wife Leila after podcast listeners reached out inspired by discussion about declining flip flop quality. The company manufactures and sells flip flops globally and has grown to have products distributed in major retail stores. Jeremy's background as a political consultant contributed to the company's growth strategy.

China Ecom Boost is an agency founded by Matt Kowalak that helps manufacturers, product companies, and celebrities navigate and market themselves in the Chinese market. The company leverages deep expertise in Chinese supply chains and evolving commerce dynamics to facilitate business expansion. Matt has undergone a major re-evaluation of his business model to focus on the vast opportunities he sees in China.

Legendary LeadGen, founded by Dana Lindahl, is a lead generation company that specializes in helping marketing agencies connect with their ideal prospects. The company operates in the competitive lead generation space where cold email outreach is positioned as a dominant method for acquiring new customers alongside word-of-mouth marketing.

GFNY is a cycling event company founded by Uli Fluhme that brought the Italian Gran Fondo model to New York City, becoming the first of its kind in America. The company has successfully expanded into a global brand by licensing and franchising the event concept to other markets.

HireMyMom is a well-established agency founded by Lesley Pyle that specializes in placing stay-at-home parents as remote workers for companies worldwide. The company addresses entrepreneurs' hiring challenges by tapping into a talent pool of stay-at-home parents who tend to make reliable team members, as demonstrated through case studies like Louise Gray (former Sony executive) and testimonials from founders like Kiri Masters of Bobsled Marketing.

Sarah Kornblet attended a Tropical MBA seminar in 2012 with 44 other listeners and subsequently became a successful attorney specializing in legal services for online entrepreneurs. The episode explores her journey since the seminar and emphasizes how business ideas develop and mature over time.

DenberTech was a cryptocurrency payment processing platform founded by 20-year-old Dennis Ramírez Bernal in January 2022, born from the viral success of a Bitcoin-enabled Christmas cake campaign. Despite initial strong interest and leads from the campaign, the startup failed to achieve product-market fit because the market's enthusiasm for crypto payments was driven by hype rather than a genuine business problem. The company never achieved revenue and was shut down after spending approximately $5,000 primarily on customer acquisition through paid ads, with the founder learning a critical lesson about solving real problems rather than chasing trends.