What Works for Startups Like Yours?

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

Pathways is a pain-therapy app founded by Sandip Sekhon after he cured his own chronic repetitive strain injury using evidence-based mind-body techniques. Starting at $5k/month MRR through freemium subscription, the app uses a natural approach to help chronic pain patients, backed by a money-back guarantee. Growth came initially through Facebook ads, with organic app subscriber growth and recently an in-depth blog strategy beginning to drive meaningful traffic.

First customers: Facebook ads on the MVP, with initial users willing to pay for premium content

Markup Hero is a bootstrapped screenshot and annotation tool founded by serial entrepreneur Jeff Solomon in 2020. The product has grown to ~10,000 paying customers generating approximately $20,000/month MRR through SEO-driven content marketing and a freemium model ($4/month for paid tier). Operating as a lean 3-person team with minimal overhead, it's positioned as a profitable lifestyle business.

SimpleLogin is an open-source email alias service that protects user privacy by allowing them to create different email identities for each website. Founded by Son NK after being inspired by Edward Snowden's documentary, the bootstrapped SaaS grew organically through content marketing and endorsements from privacy influencers to reach $3,000 MRR with approximately 1,000 subscribers.

First customers: Organic word-of-mouth and open-source community feedback

Stratascratch is a freemium SaaS platform helping aspiring data scientists and analysts prepare for technical interviews through SQL and Python practice questions. Founded by Nathan Rossidi in 2017 as a side project to improve his university students' learning experience, it took two years to reach $1,500 MRR by 2019. Nathan grew the business through content marketing and blogging while maintaining it as a 5-10 hour/week side project alongside his full-time job and adjunct teaching role.

First customers: Free access provided to university students, then freemium model adopted after realizing users needed to experience value before paying

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.

Salonist is an all-in-one salon management SaaS built by Neeraj Gupta starting in 2016 that serves 10,000+ customers across salons, spas, and wellness businesses. The product emerged from direct customer pain points discovered through his web development agency, and grew through organic search visibility, digital marketing, and word-of-mouth referrals with a freemium model.

First customers: Direct outreach to salon owners in Paragon Mall Singapore for beta testing and feedback

Stephanie Nicolich founded Success Society in August 2015 as a free community platform for women entrepreneurs, offering resources, tools, training, and mentoring from seven expert CEOs. The platform has grown to tens of thousands of active members with over 500 fully profiled members, generating revenue through a $97/month e-course offering and an $1,997 eight-week intensive bootcamp that runs quarterly with attendance doubling each iteration. She's built a team of eight and leveraged email marketing (4,000 opt-ins in a four-week period from a free lead magnet) to drive growth.