Own Pain Startups

GitLab is a single-application DevOps platform used by over 100,000 organizations and 10,000 paying customers. The company has raised $468 million in total funding, with their latest Series E round of $268 million at a $2.75 billion post-money valuation, positioning them for an IPO or direct listing in 2020. GitLab demonstrates exceptional unit economics with 150%+ net revenue retention, 72% of ARR from enterprise customers, and plans to break $200M ARR by next year.

Rocket is a full-stack recruiting marketplace founded in late 2016 by Abhinav Agrawal that combines human recruiters with technology to help companies hire talent faster. The company charges a combination of subscription and performance-based fees (typically 20-30% of first-year salary), with customers averaging $80-100K annually and placing 100-1000+ employees per year. Growing from $600K in 2017 to $3M in 2018 to on-track $6M+ in 2019, Rocket has 100 customers, 30 team members, is cash flow positive, and is seeking a $7-10M Series A to expand to 5-10 new offices.

Workable is a SaaS recruiting platform used by 20,000 companies across 100 countries. The company has grown from 6,000 customers in May 2018 to 20,000 today, with ARR expected to reach approximately 30 million by year-end, representing 50-60% year-over-year growth. The platform helps employers find, evaluate, and manage hiring, with a focus on mid-market and SMB companies, and has facilitated nearly 1.5 million total hires.

Proleads was a B2B SaaS tool founded in 2010 that automated sales development through personalized email outreach at scale. After 8 years of operation with high churn issues, founder Anders Fredrickson acquired the Brisk.io technology in 2017 and joined the Alchemist Accelerator, eventually selling the company in February 2018 to Outbound Works for over $1.8M (more than 2x the ~$900k raised), with a mix of cash and stock.

Syncrotab is a SaaS presentation platform designed specifically for face-to-face business pitches, allowing presenters to display high-quality PDFs on clients' devices with annotation capabilities. Founded by David Talbot in 2015 with $120k in friends and family funding, the company has bootstrapped and secured a major investment bank to prepay over $200k to fund development, representing an unconventional go-to-market strategy focused entirely on landing one marquee customer before broader expansion. The team of 4 (founder plus 3-person dev team) is deliberately waiting to close this large enterprise deal before pursuing other sales, betting that success with the largest bank will unlock relationships with 20,000 wealth advisors.

Bombora is a B2B intent data platform built on a massive data cooperative with thousands of publishers (including Wall Street Journal, Forbes, Bloomberg, G2, Captera) that identifies companies actively researching products to buy. The bootstrapped company reached $30M+ in ARR in 2020 with 65% subscription revenue and ~2,000 customers, growing 35% YoY while recently expanding from enterprise (Fortune 1000) to mid-market customers at lower ACVs.

Stratified is a SaaS platform founded by Derek Wang in January 2015 that helps enterprises ingest, analyze, and visualize unstructured data using AI. After 5 years, the company has grown to 120 people globally, serves approximately 50 customers with an average contract value of $100,000-$200,000 annually, and generates approximately $6 million in ARR. The company demonstrates strong expansion economics with 120-130% net revenue retention and only 3.6% annual gross revenue churn.

Solution is an all-in-one marketing and experience automation platform built specifically for manufacturing and wholesale distribution SMBs. Founder Scott Snyder bootstrapped the platform with over $1 million of his own capital over 3 years of development, and is currently in early-adopter phase with 15 companies (10 in Singapore, 5 in Southern California) before converting them to paying customers in Q1, targeting $35-$113/month pricing.

Brex is a corporate credit card platform for startups founded by Enrique Dubugres and his co-founder after they sold Pagarme (the Stripe of Brazil) in September 2016. Launched through Y Combinator Winter 2017, Brex targets tech companies that can't access corporate credit without personal guarantees, offering higher limits, instant approval, and better product experience. The company generates revenue through interchange fees (0.5-3.5% per transaction) and has achieved 0% default rate while growing GMV 50-70% month-over-month on approximately $200M in raised capital.

Thopos is a SaaS platform for youth sports organizations to manage registrations, payments, scheduling, and member communications. Founded in 2014 by Shrinni Shidratti, the company bootstrapped for years with a $250k friends and family round, reaching 125 paying customers and ~$5.5k MRR with 10% annual churn by the time of this interview.

Fizna is a SaaS platform launched in 2015 that functions as an 'autocomplete for 3D design,' helping engineers and manufacturers avoid redesigning components from scratch by searching their internal design databases. Originally built to address IP protection in 3D models, the company pivoted to engineering when customers recognized its value for design efficiency. With 15 enterprise customers, $2M raised, and a team of 15 in Ohio, Fizna grew from zero revenue a year ago to approaching $1M ARR through direct enterprise sales.

Benevity is a B2B SaaS platform founded in 2008 that helps Fortune 1000 companies manage employee giving, volunteering, and grants programs. With 450 enterprise customers averaging $100k ACV and ~$45M ARR (50% from SaaS), the company has achieved 98% customer retention, 120%+ net revenue retention, and 47% YoY growth, primarily driven by word-of-mouth referrals and low CAC from strong service delivery.

Growth Marketing Conference evolved from Startup Socials community mixers into a major industry event over five years. Starting in 2014 with 300 attendees and $150K expenses, it grew consistently ~25% annually, reaching 1,700 expected attendees in 2019 with $1.3-1.5M in projected revenue (50% from sponsors). The event became profitable in 2015 and achieved true scale through partnerships, strategic speaker curation, and sophisticated sponsor relationship management.

Michael Ozalparti founded Inform in 2018 as a SaaS pivot from his professional services company Sabazo, which grew to $1M ARR over five years. Inform is a learning management system targeting hospitality enterprises, differentiated by bundled, high-quality video and text-based training content. The company is bootstrapped with $200k saved from Sabazo and is currently in beta with pre-revenue status.

Thousand Eyes, founded in 2010 on a $1M NSF grant, provides network intelligence and digital experience monitoring for enterprise customers. The company now has 250 employees, 500+ customers with an average contract value of $100K, and exceptional net revenue retention of 130-140%. With revenue since year one and a disciplined approach to capital deployment, they are targeting IPO readiness in 2-2.5 years.

TeamBuilder is a bootstrapped SaaS platform for strength coaches and athletic trainers to manage workout programs and athlete data digitally. Founded in 2013 by Hewitt Tomlin and his college roommate, the company has grown to 10 employees, ~1,000 customers, and $1M ARR with 90% revenue retention by focusing on content-driven inbound marketing and consultative sales demos.

Veeamly is a priority workspace SaaS that consolidates collaboration tools like Slack, Jira, and Zendesk into a single desktop app with an AI-powered prioritized feed. Founded in mid-2017 by Emno Gariani and CTO Ramzi, the company was pre-revenue at the time of this interview with ~100 free beta users showing strong engagement (4 hours/day average usage). The team had raised $200K from angels and a seed accelerator (The Refiners) and was fundraising an additional $500K to reach product-market fit and launch paid pricing in April (Q2).

MetaVisor is a health information platform founded in 2012 (launched 2013) that personalizes medical research and clinical trial information for patients based on their specific condition and treatment stage. The company operates on a dual revenue model: licensing technology to healthcare organizations and partners (like the Leukemia and Lymphoma Society), and being paid by biopharma companies to identify and engage patients for clinical trials. With 130,000 subscribers across 129 countries and a team of 7 full-time staff plus ~35 part-time contributors, MetaVisor is on track for profitability within 12 months of their upcoming $1-5M fundraise.

Customerville is a design-driven customer feedback platform founded 15 years ago by Max Israel as a solution for his own retail business. After realizing he hated traditional surveys eight years ago, he pivoted the company to blend technology, art, and behavioral science to make feedback engaging. Today, bootstrapped and profitable, Customerville serves 50-100 enterprise clients with an average contract value of $250,000/year, generating over $1M monthly revenue with 50-100% year-over-year growth.

Writer Access is a content marketplace founded by Byron White in 2010 that connects 25,000 customers with 15,000 freelance writers, editors, and content strategists. The platform pivoted from a pure marketplace transaction model (70/30 split favoring freelancers) to a SaaS subscription model in late 2017, charging $39-$349/month. By 2017, the business generated $7.2 million in total revenue across the marketplace and related conference business, with a small team of 11 operating profitably from Boston and remote locations.