SaaS Interviews with CEOs, Startups, Founders

20 year old wins $3m playing poker, launches SaaS. He raised $18.2m. After 7 years and dilution down to under 50% he left to launch his new bootstrapped company. Whippy helps lawyers run their operations and hit $4m ARR this month. Can he hit $10m bootstrapped?

CEO Griff Parry launched m3ter in 2020 after selling his first company Gamesparks to AWS. Today 10-100 customers pay him platform fee's and usage fee's to use his usage based billing API tool. He doesn't code but across his team of 56, more than 25 are engineers. Can they scale into their last round valuation?

Launched in 2016 selling software to Music Repair Shops, TudoDesk exited for $1m+. This is the low stress, high wealth way to build a software company. TC won't write about you, but it doesn't matter, you'll get wealthy fast!

Launched in 2016, CEO Matt Prados got rich off dividends and profits. He's bootstrapped to $20m in revenue with plans to hit $32m in 2024. Can he do it? His outbound call center strategy might get him there. 

Tarja recognizes that energy in Finland is a hot space. She's launched a marketplace connecting 100 apartment complex owners with 100 providers of energy services like solar and heat. Shes raising a $15m fund to then back these projects that go through her marketplace. Will she get the $15m SPV closed and change the course of energy efficiency before 2025?

Matt Britton sold his agency for $50m in 2010 then launched Suzy.com in 2011. The original version, Crowdtap, was a mobile app where consumers could test new enterprise products like candy bars, detergents, and other items. The firm struggled and then doubled down on Enterprises paying for user research through its software, hitting $10m Revenue in 2018. Last year the firm did $65m in revenue and burned $12m. Britton says “We’ll hit $82m revenue this year and plan to burn $9m with a track to $100m ARR by mid 2025.” Will he get there?

Despite large competitors like CloudBooking, Guesty, and other hotel management platforms, RoomChecking CEO Jonathan Weizman has carved out a $2m niche. He specifically helps hotel owners in France organize cleaning schedules by hotel cleaners as guests check out. 

He turned down $20m in 2021 for his Slack competitor, Chanty.com. Today, the company has over 24,000 paying customers and does $3m revenue, profiting $1.2m in 2023. The company is fully bootstrapped. Can he find a sales co-founder willing to hustle hard for 15% equity?

He raised $16.9m and hit $40m in revenue. Success? Wrong. He shut his unprofitable grocery delivery company down in 2021 then spent a year working with liquidators. Today, he’s moved industries to the Dev Ops space and launched his disaster recovery SaaS Bennudata.com. 

His first company grew to a few million in revenue before exiting in 2021. After a 2 year earn-out, he left to build a new company. When his Customer Health Tracking excel template went viral on linkedin, he capitalized and launched his SaaS. The post led to 6 customers paying $500/mo for his revenue operations platform, Revos.ai 

After Tiger gave the founders $7m in a 2021 secondary at a $625m valuation, they took their team to Morocco for a team retreat. Seeing a weak market, they chose to cut the team from 225 down to 150 and become profitable. Despite these cuts, they’ve doubled revenue by selling 5 key product lines to sales teams. Will they do $50m in revenue in 2024? Chilipiper.com

His 13 person sales team does 2,000 calls per month. This engine has landed him 4,100 customers who pay him to help plan their field sales reps driving routes to save gas and make more money. He’s bootstrapped the company to $6m and made a full recovery from COVID down year 2021. He’s used debt to scale to keep 100% equity. Will he get the exit he dreams of in 2024 and reap the rewards of bootstrapping and keeping equity? Badgermapping.com

300,000 homeowners cut their lawns every month with Greenpal who connects them to 35,000 lawn care companies. In 2023, the company did $30m in total lawn cuts and kept 15% of that revenue to generate $4.5m in revenue. They do this all with 0 FTE’s. Why? Bryan wanted freedom. He wanted to travel 11 months of the year while building a company he loved. VC wasn’t an option. Listen in if you’re looking to build a business and life you love with no external pressure. Yourgreenpal.com