Own Pain Startups

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.

Regpacks is a registration and payment processing platform for the service industry, primarily serving education, camps, courses, and afterschool programs. Founded in 2012 by Asaf Darasi and bootstrapped throughout its growth, the company reached $10.5M+ ARR with 1,500 active customers by generating revenue through three streams: SaaS subscriptions, payment processing fees, and purchase protection insurance. The introduction of intelligent payment installments drove a 30% revenue increase for adopting customers.

Martin Hadding, a Microsoft 365 architect with 20 years of experience, built SPRobot as a SaaS solution to solve the content sprawl problem he encountered repeatedly in enterprise consulting. His agency BeSolve (generating $800k revenue in 2022) invested $150,000 into the product, which is currently in beta and targeting SMBs at $150-200/month per tenant. The product is validated through a tight-knit Microsoft 365 community and will launch commercially within 3 months.

True.me is a SaaS platform that helps students find the right college fit using AI-powered matching technology, addressing the real problem in higher education—not getting in, but graduating successfully. Founded by Dave Hurwitt in February 2020, the company has signed 12 schools at $10,000-$15,000 per year, generating approximately $120,000 in ARR, with plans to reach 30-40 schools to secure institutional funding. Dave bootstrapped the company with angel capital (a couple hundred thousand), outsourced engineering to trusted developer networks, and is now positioning True.me to disrupt the $15 billion college admissions marketing industry.

Agilentz is a vertical SaaS platform serving retailers, restaurants, and grocers with data analytics and operational intelligence. Founded in 2006 as a hardware-based loss prevention company, Russ Hawkins transformed it into a pure-play SaaS business in 2013, pivoting from video verification to comprehensive data analytics. Today the company generates ~$35M ARR from ~300 enterprise customers (average ACV $125K), with 17% YoY growth, backed by Quadria Capital private equity.

Factor Technology is a bootstrapped SaaS company founded in 2017 by geophysicist Hugh Winkler and two partners that helps oil and gas operators automate well positioning using machine learning. They've acquired six customers (including one top-10 US oil company) and are operating on a day-rate pricing model ($90/day for consultancies, enterprise packages for majors). Winkler expects to break $1M in annual revenue in 2024.

Sprinto is a SaaS compliance platform co-founded by Girish (who previously exited Recruiterbox in 2018) that helps other SaaS companies move upmarket by managing security and compliance requirements. Girish shared a detailed framework for moving from SMB to enterprise markets, drawing on lessons from his previous startup's MRR growth transformation between 2015-2018, emphasizing the need for deliberate positioning, building trust through compliance certifications (SOC2, ISO 27001), and establishing enterprise sales capabilities.

Bloom Growth is a B2B SaaS growth agency founded by someone with experience at Andreessen Horowitz and roles at companies like Planet Labs and Zora. The founder presents a contrarian thesis that SDRs should be treated as brand marketers and integrated with demand-gen efforts to reduce CAC by 20-40% and increase pipeline velocity. They offer free marketing strategy workshops and operate the Pipeline Superheroes Podcast.

Carl founded Acumen.io (formerly Kimolayo) seven years ago to democratize data-driven decision-making by embedding customer-facing analytics directly into SaaS platforms. The company provides a building block component that allows SaaS founders to offer dashboards and analytics to their end customers, positioning itself as the analytics equivalent of Stripe for payments or Auth0 for authentication. Through research on 250 top G2 companies, Carl identified major gaps in how SaaS companies implement client-facing analytics and created a five-level framework for improving customer analytics experience.

Andy Gotthier, president of Fractional CFO with Mighty Startup, is a serial entrepreneur who previously co-founded and scaled BotKeeper to Series B funding before exiting. He now helps startups in the $2-5M ARR range scale faster by implementing proper finance functions across planning, reporting, and analytics, and strategic decision-making. His approach emphasizes the ROI of investing in finance as a growth enabler rather than a cost center.

Code Mantra is an intelligent document automation SaaS company with $8M ARR that pivoted from a services business to focus on extracting contextual data from complex PDFs. Founded in late 2014, the company found product-market fit in 2019 when an existing customer asked them to build a compliance solution after being sued by a federal agency. The company has achieved 200% NRR during validation phase and is now in scaling mode while remaining self-financed.

RevOps Squared is a SaaS benchmarking platform founded by Ray, an experienced executive with 30 years in subscription software and multiple exits. The company provides segmented SaaS performance metrics and benchmarks that help founders understand enterprise value drivers, replacing generic one-size-fits-all metrics with cohort-based analysis by ACV, revenue size, and business model. They recently launched an industry benchmarking program with 12 partners offering an interactive portal where companies can anonymously compare their metrics.

Salesprint is a sales engagement platform that gamifies and visualizes sales activities to help inside sales teams hit their targets. Founded in 2014 as a bootstrap company, it bootstrapped until 2018 when the founder raised money for the first time. Currently at $8M ARR, the company focuses on operational efficiency through aligned strategy, bite-sized goals, and team motivation—principles the founder shared at SaaSOpen conference.

MeSH is a corporate spend management SaaS platform that helps finance organizations automate month-end close processes and reduce manual work. Founded by Anna King, the company targets global enterprises seeking to eliminate productivity killers like data silos, manual data entry, and receipt chasing. MeSH integrates with existing ERP and CRM systems to provide real-time revenue visibility and enable finance teams to focus on strategic value-add activities.

Sales Confidence is a community and coaching platform for sales leaders and salespeople built by a former LinkedIn executive. The founder leveraged TikTok as a primary growth channel, growing from zero to 6,000 followers in 50 days and directly generating revenue ($3,000 sale) through TikTok visibility that prompted LinkedIn engagement. The founder advocates for video content and TikTok as an underutilized B2B marketing channel with lower customer acquisition costs compared to traditional platforms.

Ebster is a B2B SaaS platform that helps sales teams become data-driven by automating CRM data capture and analyzing relationship engagement to improve deal outcomes. The company helps teams identify high-performing sales practices, with customers seeing 3x win rate improvements through better engagement metrics and structured pipeline reviews. The platform integrates with Salesforce and HubSpot to provide visibility into deal dynamics and stakeholder engagement patterns.

Remote is a SaaS platform founded in 2019 by Dutch founder Jo Bendervoort and Portuguese founder Marcelo Leb that enables companies to hire and manage employees anywhere in the world by handling global payroll, benefits, compliance, taxes, stock options, and visas. The company operates as a fully distributed organization across 1,000+ employees in 70 countries and uses its own product as their first customer. Remote emphasizes a strong culture built on five core values—excellence, kindness, ownership, transparency, and ambition—operationalized through async work practices, public documentation in Notion, and intentional community building.

Expandee is a LinkedIn automation SaaS founded by Stefan that bootstrapped to $7M ARR in 2.5 years by helping businesses find and engage targeted audiences on LinkedIn. The company developed sophisticated sniper-targeting strategies including post engagement scraping, event attendee extraction, poll voter engagement, and personalized GIF animation campaigns that achieve 70% connection acceptance rates and 55% reply rates. Stefan shares the company's playbooks and strategies publicly through content and speaking engagements.

Vendor is a SaaS management platform co-founded by Ariel Diaz (previously founder of Blissfully, which merged with Vendor about a year ago). The company helps customers optimize SaaS spending and discover the right products by analyzing market data. As a 400-person, post-PMF company that has raised $200 million, Vendor competes in an increasingly crowded market and emphasizes velocity as the primary sustainable competitive advantage.

Everywhere is a fintech SaaS platform founded in 2018 by Larry Talley that enables businesses to collect payments via text messaging and phone numbers. Starting from barely $1M in revenue in 2018, the company accelerated dramatically after moving to Austin and focusing on a pay-by-mobile solution, reaching over $25M ARR by the current year. The company has built 10,000+ customers and 18,000+ users by partnering with major banks (Bank of America, Wells Fargo, KeyBank) and card networks (Visa, Discover), using a white-label model to reach thousands of merchants indirectly.