Coping with the everyday struggles on the way to $20M+ ARR with Matthew Bellows

On this month’s episode of the Struggle, Alex speaks with Yesware co-founder and chairman of the Board, Matthew Bellows. He interviewed him a year ago for another episode of the SaaS Revolution Show where the focus was on the part of the story that showcased Yesware’s success to date. Today they take a step back and, in the spirit of The Struggle,  chat about the myriad of struggles that Matthew has been through, that isn’t often discussed, on the way to that success.

Matthew started Yesware in 2010 together with his co-founder and CTO Cashman Andrus. The plan was to bootstrap but as demand for engineering talent increased while savings were drying up very quickly, Matthew and Cashman decided to fundraise. According to the blog posts, they had read it was meant to be easy. The reality turned out anything but.

While the experience was difficult, Matthew believes that for Yesware it was the right thing to do. It also served as an important gut check - Do we actually want to run this company and build this product? The answer was yes and eventually, they managed to raise a $1 million in 2011, which helped fuel the initial build of the communication platform for salespeople. Yesware has gone on to raise a total of $48 million. The Yes answer to that question has always remained. Matthew goes in-depth on why he never wanted to give up.

He is incredibly open and honest throughout the conversation and covers a large array of topics such as the inherent conundrum of being CEO, how he has grappled with a very strong case of Imposter Syndrome, the struggles of managing executives, how meditation has helped him immensely, why he stepped down as a CEO in August last year and he feels about it. We finish off with the one piece of advice he would give to fellow founders and CEOs.

This is the untold story of Yesware: 7 years in the making.

If you would like to share your story of struggle with us on the show, get in touch by emailing [email protected]

Listen to the original SaaS Revolution Show episode with Matthew Bellows

You can find more information about his executive coach, Jerry Colonna here

Check out the other ways SaaStock is helping SaaS founders move their business forward: 

🇮🇪 SaaStock Europe: 14-15 October 2025 | Dublin, Ireland
Book tickets: https://saastock-europe.com/tickets/

🇺🇸 SaaStock USA 2025: April 2026 | Austin, Texas
Book tickets: https://saastock-usa.com/

🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)

🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)