What Works for Startups Like Yours?

Dr. Sheri Walling, a psychologist and entrepreneur, launched her book 'Touching Two Worlds: A Guide for Finding Hope in the Landscape of Loss' which explores grief through personal essays, tactical practices, and psychological analysis. The book shares her experience losing her father to cancer and brother to suicide six months apart, while simultaneously experiencing career success and family flourishing. She executed a multi-month launch strategy starting with endorsement outreach in November, a circus-themed launch event in May, and an ongoing podcast tour with systematic outreach to contacts and media platforms.

Lenny's Podcast is a top 10 technology podcast that launched six months before this episode with 50 episodes published, 2+ million downloads, and 40,000-50,000 subscribers across Apple Podcasts and Spotify globally. The podcast interviews world-class product leaders and growth experts on building and growing successful products, using Notion to coordinate operations and guest management.

Tracy Osborn self-published Hello Web Design, a book teaching design fundamentals to non-designers, after launching it successfully on Kickstarter (raising $22,000). She later partnered with No Starch Press to republish it as a hardcover, shifting from self-publishing to a traditional publisher to offload marketing while maintaining her evergreen content. The book focuses on 80/20 design principles like typography, color, spacing, and layout that enable developers and founders to design interfaces themselves.

Josh Comeau built CSS for JavaScript Developers, an interactive online course combining videos, articles, widgets, and mini-games to help JS developers master CSS. He validated the idea with a one-week pre-order campaign targeting $50k in sales and instead generated $550k in revenue from nearly 5,000 sales. His success came from building in public on Twitter, maintaining a high-quality blog that attracts 60-90k monthly visitors, and leveraging an email list of 20k subscribers.

First customers: Email to waitlist during pre-order week

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

FinMasters is a finance education blog founded by Ionut Neagu in November 2020 to provide unbiased financial information. After spending $477,924 on building and growing the site (initial $50k plus $40k on content promotion and ongoing costs), the site has grown to $6,000 MRR through SEO, content marketing, and strategic website acquisitions. Ionut continues to invest heavily in growth, aiming for revenue to eventually cover content and team costs.

Pete McLeod launched NoCS Degree in July 2019 after quitting a minimum wage job to become an indie hacker. The blog interviews successful developers without computer science degrees, generating $70 in first-week revenue and 48,000 page views through a viral Hacker News launch. Within months, Pete scaled to ~$2,000/month MRR primarily through newsletter sponsorships from coding bootcamps and SaaS companies, applying high-ticket B2B sales tactics rather than pursuing low-value subscriptions.

First customers: Newsletter sponsorship ads - Pete messaged people in communities like Indie Hackers and Telegram pitching his blog audience to coding product companies.

Blockworks Group, founded in 2017 by Jason Yanowitz, is a media and education company focused on blockchain, cryptocurrency, and their intersection with macroeconomic markets. The company produces events, educational content, and podcasts analyzing how monetary stimulus, inflation, and currency debasement are driving institutional and retail adoption of alternative assets like Bitcoin. Yanowitz's thesis centers on Bitcoin as an inflation hedge and alternative to government-controlled fiat currency, particularly as central banks increase monetary stimulus.

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