Side Project Startups

Nick DiGiovanni is a creator and entrepreneur who has built a massive following of over 15 million across YouTube and TikTok through viral food content featuring record-breaking culinary creations. Beyond his creator platform, he has launched analog business ventures including a DTC salt and seasoning company and a cookbook titled Knife Drop. His growth demonstrates the power of social media virality and content-driven audience building.

The Sorry Girls is a media company co-founded by YouTubers Kelsey MacDermaid and Becky Wright, who met as film students in 2010. Starting with DIY videos created for fun, they grew to over 2 million YouTube subscribers. The company navigates the creator economy through brand deals while maintaining their values.

Property Hub grew from The Property Podcast, co-hosted by Rob Dix for a decade, into a multi-7 figure online community and real estate business. The turning point came when hundreds of listeners showed up to their first in-person meet-up, revealing significant demand. Today the podcast reaches 400,000 downloads weekly, and Rob's strategy centers on creating abundant free content while building monetized community offerings.

Buffalo Bottle Craft is a dumpster diving business founded by Dave Sheffield that started as a college hobby. A Vice documentary about the practice gained nearly 1.5M views, creating significant media interest and validating the business model. The founder now uses content creation as both product research and growth engine, asking followers what products they'd make from found materials.

Blue Fish is a luxury concierge service founded by Steve Sims that creates bespoke, high-end experiences for corporate executives, celebrities, and professional athletes. Starting from a Hong Kong nightclub password in 1993, the company evolved into a legitimate business by securing major contracts with New York Fashion Week, the Kentucky Derby, and the Grammys. In 2016, Blue Fish generated nearly $9 million in revenue through curating exclusive, bucket-list experiences tailored to ultra-high-net-worth clientele.

Automattic was founded by Matt Mullenweg in 2005 to build services around WordPress, the open-source blogging platform he created in 2003. The company operates primarily as a subscription business with three main products: WordPress.com hosting, Jetpack services, and WooCommerce e-commerce platform. Automattic has grown to over 100 million ARR, operates fully remotely across 62 countries with 650 employees, and has strategically remained private to maintain long-term strategic flexibility.

Ilias Segalexis is a former software developer who left a €40,000/year corporate job in Greece to build a media company targeting the software development industry. His network of properties (primarily Java Code Geeks) reaches over 1.5 million people per month and generated mid-six figures in 2015 with an 85% net margin through advertising, sponsorships, and lead generation partnerships.

Carnivore Club is a subscription meat box service founded by serial entrepreneur Tim Ray in September 2013, launching via Indiegogo crowdfunding. By February 2016 (approximately 2.5 years after launch), the company was shipping over 5,500 boxes monthly and generated $1.3M in revenue in 2015, with projections of $2.2M for 2016. The company bootstrapped with $100K from Ray's previous exit and achieved profitability while maintaining 35% gross margins, primarily through podcast advertising to reach their core audience of down-to-earth, blue-collar customers.

Results Junkies is Paul Singh's community-driven newsletter and platform that evolved from a blog into a weekly newsletter written during his time as an investor. It's not currently a business, but rather a passion project bringing together a couple thousand founders and investors in Slack and through meetups to discuss building businesses. Paul built this after exiting Disruption Corp to 1776 and spending 30 days traveling to startup hubs globally to understand how communities grow.

StudyMate is a student learning platform built by Zevi Arnawitz, a non-technical PM at Meta with zero coding background, using AI-powered development tools like Cursor and Claude. The app allows students to upload study materials and generate interactive quizzes with multiple question types. Zevi developed an innovative workflow using slash commands, Claude code review, and multiple AI models working in concert to build, review, and refine features without writing code himself.

Product Hunt started in late 2013 as a side project and newsletter, growing organically within the tech community before being incorporated 4-5 months later. Ryan Hoover built it as an experiment to help founders and tech enthusiasts discover new products, initially funded by his own capital before raising seed and Series A funding. The platform became a launchpad for thousands of startups and eventually was acquired by Angel List.

MrBeast (Jimmy Donaldson) is a content creator who built a YouTube empire by obsessing over viral video creation and implementing systematic improvement principles. Starting from age 11 with zero views, he spent 8 years perfecting his craft, initially making only ~$500/month, before eventually cracking the code to viral success. His approach emphasizes the 'Rule of 100' (improve one element with every 100 videos), obsessive idea generation, building a creative team, and the belief that 'impossible is possible' through systematic problem-solving.

Zuru is a toy manufacturing and consumer goods company founded by Nick Mowbray and his brother Matt, growing from a bootstrapped operation sleeping in bushes in China to a $2B+ revenue private company. The founders used relentless cold outreach, persistence through repeated rejection, and a focus on manufacturing excellence and automation to disrupt the toy industry and expand into FMCG categories. Today Zuru runs at ~40% net profit margins and operates globally with sophisticated automated production lines.

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.

Contraigne Thinking is a newsletter and media company founded by Cody Sanchez that discusses boring businesses and small business acquisitions. The company has grown to a couple hundred thousand newsletter subscribers with approximately 5 million total subscribers across all channels and around 100 million monthly views. Cody built the company while running a family office that acquires and holds small businesses.

Ben, a producer on 'My First Million,' created 'How to Take Over the World,' a history podcast that gained traction through word-of-mouth and was discovered by Sam Harris and MrBeast. His philosophy centers on creating content that generates obsession rather than broad appeal—using strong emotions, aggressive branding (the podcast name and intro music), and bold creative decisions to build a small but passionate audience that naturally evangelizes the show.

SiteArrow is a web hosting business founded by Kevin Graham that emerged from his entrepreneurial journey and philosophical reflections on 'The Helsinki Bus Theory.' The company pursued an aggressive growth strategy, acquiring 9 different businesses in less than a year, but this led to founder burnout and prompted a strategic pivot toward sustainable growth principles.

Ryan Robinson runs RyRob.com, a blog and podcast called The Side Hustle Project focused on monetizing content and side hustles. His breakthrough came with a single blog post about how to start a blog and make money, which became his most successful content piece and demonstrates the power of well-targeted content marketing to build a sustainable income.

FatCat Apps is a productized business founded by David Hehenberger, who began his entrepreneurial journey as an SEO consultant after completing an internship at Tropical MBA in 2010. The company represents a successful transition from consulting to a productized service model, helping entrepreneurs achieve financial independence and escape traditional corporate constraints.

Growth Ninja is a performance-based Facebook ads agency founded by Vincent Nguyen in 2015. Vincent built the company after apprenticing with Empire Flippers, leveraging his experience in performance marketing. The episode focuses on Vincent's journey navigating social pressures while building his business, including hiding his college dropout status from his family.