Side Project Startups

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.

Sam Parr launched HustleCon in June 2024, a paid tech and entrepreneurship conference, with just a 200-person email list and a domain name. Within 7 weeks, he grew the email list to 2,500 people and generated $60,000 in revenue with ~$50,000 profit by using content marketing (blog posts and infographics about speakers posted to Hacker News), tiered pricing with urgency tactics (fake countdown timers), and strategic speaker recruitment through cold emails. Subsequent events scaled to $500,000+ in revenue with 50%+ margins by leveraging sponsorships, volunteer labor, non-union venues, and vendor partnerships.

The Hustle/The Move is a podcast created by entrepreneurs Sam Parr and Sean Cannell featuring unfiltered conversations about startups, business ideas, and market trends. With around 15 million downloads per year and aspiring to reach 100,000 daily listeners per episode, the show has built a loyal audience of engaged listeners who are inspired to start their own ventures based on ideas discussed on the podcast. The hosts leverage their existing networks and company exits (Sean sold to Twitch) to attract high-profile guests and have recently launched a venture fund to invest in companies featured or discussed on the show.

My First Million is a podcast hosted by Sean Puri and Sam Parr, two serial entrepreneurs who discuss startup ideas and business opportunities. The show grew from entertainment content to becoming influential in the startup ecosystem, eventually being acquired by HubSpot. The hosts leverage their platform to build social capital, invest in startups through rolling funds and syndicates, and convert audience trust into financial opportunities.

Close is a CRM tool helping small and medium-sized businesses close more deals and communicate better, founded by Steli Efti. The company has grown to 45 people across 14 countries and is profitable, though exact revenue figures are not disclosed in this interview. Steli emphasizes building a sustainable company focused on serving entrepreneurial customers rather than chasing enterprise deals, prioritizing long-term relationships and maintaining a workplace culture that fosters both professional growth and personal fulfillment.

Black Hops Brewing is a craft brewery in Australia founded by Dan Norris that has achieved over $10M annual revenue through a content-driven, community-focused marketing approach. Rather than traditional beer industry marketing (which typically spends 11% of revenue on ads), Black Hops applies startup-style brand building through transparency, storytelling, and community engagement—including podcasts, blogs, home brew competitions, equity crowdfunding, and financial transparency.

Lockpick Entertainment was a small Swedish game studio that created Dreamlords, a hybrid MMO RTS game that achieved thousands of players and millions in revenue after launching in 2006. However, the company failed after 6 years due to a combination of scope creep, lack of product-market fit, and an inability to sustain development velocity post-launch. The founder's key lesson was that overshooting scope and expanding features instead of iterating on core mechanics proved fatal.

*openmargin was a social e-reader app that allowed users to discuss books in small communities, launched in 2011 after 2.5 years of development. Despite raising €130,000 in subsidies, the startup failed to gain traction due to being too early in the market, Amazon's DRM monopoly, slow shipping practices, and team management issues. The experience taught founder Marc Köhlbrugge valuable lessons about the importance of shipping fast and testing ideas quickly rather than over-philosophizing.

Readership was a visual analytics tool that analyzed Twitter accounts to identify content patterns and interests. Despite solid product-market research and launch efforts through Product Hunt and PR outreach, it failed because it provided no real-world value—it was cool to look at but didn't solve any actual marketing problem. The founder received hundreds of free sample report requests but zero paid conversions, teaching him a hard lesson about listening to customer feedback over personal product attachment.

Swipes was a productivity task management app that achieved significant early success with 500,000+ users and multiple awards, including first place at the Evernote Platform Award. However, after 6 years of operation, the founders failed to achieve sustainable product-market fit or a viable business model, ultimately shutting down in June 2019 due to founder burnout and resource exhaustion.

Jolt is a SaaS product started as a side hustle by a serial founder who previously sold their first small SaaS company. The founder is currently a full-time software engineer at CopyAI while developing Jolt.

LegalNomads.com is a travel and lifestyle blog authored by Jodi Ettenberg that generates full-time income through writing and content creation. Jodi has established herself as a recognized voice in the travel writing community, including delivering a closing address at the TBEX conference on making a living as a full-time writer.

SemiProCycling is a content-focused project by Damien Ruse that combines entertainment and informative cycling content to generate location-independent income. The project demonstrates how finding a unique voice in a niche marketplace can lead to sustainable revenue streams.

Nomadic Notes is an affiliate marketing business run by James Clark, a digital nomad operating as a solopreneur with no employees. The business generates revenue to support continuous travel through affiliate marketing channels.