What Works for Startups Like Yours?

All the Hacks is a top-tier business podcast launched by Chris Hutchins, a former PM and founder who left Wealthfront to pursue content creation full-time. The podcast explores financial optimization, travel hacks, and life improvement through interviews with interesting people. In 18 months, it reached top 5-10 in business podcast rankings through authentic content, guest curation, and consistent weekly releases.

First customers: Kevin Rose's podcast announcement and organic audience from existing newsletter

Gergé Oros is a former Uber engineering manager who left his $320-330k compensation package to build The Pragmatic Engineer, a paid newsletter on Substack about software engineering. In under a year, the newsletter grew to 189,000 subscribers (with 80,000 added in the last 90 days) and now generates more revenue than his former Uber salary, with subscribers paying for in-depth weekly content.

CJ built Mostly Metrics, a newsletter for CFOs launched in December 2020, starting from zero subscribers by obsessively engaging on Twitter around relevant keywords and partnering with B2B companies like Ramp and Brex. The newsletter grew to 35,000 subscribers (7,000 of whom are actual CFOs) in 1.5 years with a 46% open rate and 5-7% click-through rate, attracting sponsorships of $5-10k per post and up to $100k for bundled deals. He also launched a podcast called Run the Numbers with Turpentine Network while maintaining his full-time role as CFO at Parts Tech, planning to transition fully to media within three years.

First customers: Twitter outreach and partnerships with B2B companies (Ramp, DataRails) willing to partner for free initially to build audience

Reroute Lifestyle is a lifestyle and travel blog founded by Krista Aoki that helps goal-getters achieve financial freedom through remote work and online income streams. Starting in 2017 with zero investment, Krista grew the blog to 11,000 monthly page views and $1,500 MRR in 6 months through Pinterest marketing and content-driven storytelling. The business generates revenue through affiliate marketing, product sales, and services.

First customers: Amazon Affiliates commission earned within days of starting the blog

Starter Story is a content platform that interviews and profiles founders running businesses generating $10K-$100K+ monthly revenue. Founded by Pat as a side project in 2016, it grew to include a blog with case studies, YouTube channel, community, and products by requiring founders to publicly share their revenue numbers. HubSpot acquired the company, with the deal expected to close around the time of this interview.

Founders is a solo-hosted biography podcast launched in 2016 by David Senra that has grown to over 100,000 unique listeners per episode in 7 years. The podcast breaks down biographies of successful entrepreneurs, artists, and historical figures to extract patterns and lessons. Growth has been driven primarily by word-of-mouth recommendations from influential figures like Patrick Bet-David and Rob Moore.

Chat with Traders is a weekly podcast launched by 25-year-old Aaron Feifield in January 2015 that interviews successful traders to help others learn trading. Starting from zero monetization but focused on audience growth, the podcast reached over 620,000 cumulative downloads in its first year with nearly 5,800 email subscribers, primarily driven by consistent weekly episodes and active Twitter engagement.

The Slow Hustle is a long-form interview podcast launched in January 2015 by Peter Awad, who juggles podcasting alongside three other businesses (Import Auto Performance, Mission Meats food brand, and a previous failed startup). The show generates approximately 8,000-10,000 downloads per month with around 2,000 downloads per episode, and recently landed on the iTunes Podcasts homepage through authentic relationships rather than gaming the system. Peter has secured two sponsors (Iowa Startup Accelerator and a law firm) charging $3,000 per 16-episode package, generating roughly $187 per episode, covering costs while maintaining the show as a labor of love.

First customers: Personal relationships and networking (Iowa Startup Accelerator through mentoring connections)

Nathan Chan launched Founder Magazine in 2015 as a digital publication featuring interviews with successful entrepreneurs. Through aggressive Instagram growth strategies (posting 5-10 times daily with a virtual assistant), he built the account from zero to 700K followers in 16 months, generating 150,000+ email subscribers. Revenue comes from multiple streams including magazine subscriptions, digital courses (Instagram course and Founders Club membership with 400 paying members), and a weekly podcast with 70,000 monthly downloads.

Stacking Benjamins is a financial entertainment podcast launched in March 2012 by Joe Saul-Sehy that grew to 152,000 monthly downloads by featuring accessible, magazine-style money content with personality. The show generates approximately $5,500 monthly from two main sponsors (Magnify Money and SoFi) at an 18 CPM rate, operates with minimal production costs (~$480/month), and is expanding into online courses to monetize the audience attention.

First customers: word-of-mouth from listeners telling friends about quality podcast content