SaaS Startups

Divi is a clean haircare and scalp care brand launched by Jordan Austin, an Instagram influencer with 2-2.5M followers across platforms, in October 2021. The product originated from Jordan's personal struggle with stress-induced hair loss and evolved from DIY scalp serum recipes she shared with her audience. In just over one year, Divi generated approximately $40M in revenue, driven almost entirely by organic word-of-mouth and user-generated before-and-after content rather than Jordan's direct audience.

PetEx is a highly technical specialist software company for oil and gas operations based in Aberdeen, Scotland. Started in 1990 as a consulting firm, they pivoted to software and generated £78 million (~$100 million USD) in revenue last year with £58 million (~$67 million USD) in profit, paying out £41 million (~$60 million USD) in dividends. With only 420 customers paying ~$300,000/year per license, they achieve exceptional profitability through enterprise-focused, high-value relationships.

Vungal was a mobile app advertising network founded by Jack Smith that pioneered cost-per-install (CPI) pricing instead of traditional CPM models. The company launched 12-18 months after the iPhone App Store opened, capturing perfect timing in a high-growth market. It sold for hundreds of millions in revenue with 60% margins for the company, making it one of the most profitable ad tech businesses.

Vongol was a mobile video ad network founded by Jack Smith that revolutionized app monetization by charging based on app installs rather than video impressions. Starting with mockup-driven cold outreach that generated ~$1M in developer commitments, the company scaled to ~$1M in daily revenue within seven years and sold for approximately $800M. The company's competitive advantage included proprietary iPhone screen recording capabilities and direct relationships with app developers.

Threads is Meta's text-based social network launched in July 2023, reaching 100 million users in its first week by leveraging Instagram's existing user base. The platform positioned itself as a kinder, more moderated alternative to Twitter, with Meta's 20 years of experience managing abuse and spam. Early traction shows potential to disrupt Twitter despite questions about long-term retention and whether it can sustain growth beyond early adopters.

After.com is a cremation-as-a-service platform founded by Mormons based in Provo, Utah. The company handles the full logistics of cremation—from lead capture to tracking—similar to Domino's Pizza Tracker, allowing customers to pre-plan or arrange services after death. The business was built on recognizing a major demographic trend: cremation in the US rose from 10% to over 50-70% of end-of-life choices in the past 20 years, a 'one chart business' opportunity.

Laird Superfood began as Laird Hamilton's home-made superfood recipe that evolved into a commercial product launched online with minimal capital investment of $20-30k. The company achieved rapid early traction through Hamilton's existing following and engaged community, reaching approximately $100-150k in revenue within the first year. The brand went public at a $400 million market cap when doing roughly $40 million in annual revenue, though stock performance has declined recently.

Syed Balkhi bootstrapped WP Beginner, a WordPress education blog, into a billion-dollar portfolio company by age 32. Starting from nothing (his father was a gas station clerk), he built WP Beginner to 2-5M monthly visitors and $100M+ annual revenue, then systematically acquired 30+ complementary WordPress products (OptinMonster, Divi, MonsterInsights, etc.), applying real estate philosophy principles like 'making money on the buy' and 'heads I win, tails I don't lose much' to identify mismanaged gems and unlock hidden revenue streams.

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.

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.

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.

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.

Shaan Puri, founder of the education platform Teachable (sold for $250M when he was 31), is now building Carry, a tax optimization platform centered on solo 401k accounts and wealth-building strategies. The company helps entrepreneurs and business owners leverage tax code advantages like QSBS (Qualified Small Business Stock), solo 401k contributions, and real estate depreciation to reduce their tax liability.

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.

Jenny AI is an AI-powered writing assistant for college students, founded by David Park. Started at $2K MRR in 2021, it grew to $300K MRR ($3.6M ARR) through strategic community building in Facebook groups and viral marketing on TikTok. The company was offered $3M but rejected it, now valued at $10-15M.

Syed Balkhi bootstrapped a billion-dollar portfolio empire centered on WordPress and related SaaS products without raising external capital. His strategy leverages what Andrew Wilkinson calls 'barnacle on the whale'—becoming deeply embedded in growing ecosystems like WordPress, QuickBooks, and Xero. His portfolio now generates over $100M in annual revenue and includes investments in companies like Seahawk Media (productized WordPress development services) and positions in open-source projects.

37signals is a 25-year-old self-funded software company built on the principle of profitability, high margins, and independence. Founded by Jason Fried and David Heinemeier Hansson, the company generates tens of millions in annual profits and maintains over 100,000 paying customers across multiple products including Basecamp, HEY, and their new ONCE line of one-time-purchase software. They've achieved this without external investment (except for shares sold to Jeff Bezos in 2006), aggressive marketing, or traditional goal-setting—instead operating with a focus on craftsmanship, low costs, and thoughtful product philosophy.

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.

Umax is a viral mobile app that uses AI to rate users' physical attractiveness and provide personalized grooming and fitness advice to help them improve their appearance. Founded by an entrepreneur who observed the lookmaxxing trend on Reddit, the app has achieved 3.5 million downloads with 5,000 new signups per day and is generating $6M ARR through a $3.99/week subscription model, capitalizing on the growing cultural shift of men investing in personal aesthetics.

GeoGuessr is a game where players guess random locations based on Google Street View imagery. Launched in 2013 by a Swedish software engineer as a side project, it grew slowly until the pandemic hit in 2020, when a paywall was introduced after Google increased API costs 14x. Revenue exploded from $467k in 2019 to $21M in 2023 with $11M EBITDA, driven by viral TikTok and YouTube creators, and now has 50M registered users and 50 employees.