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 podcast@saastock.com


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 you tickets: https://saastock-europe.com/tickets/


SaaStock USA 2025: April 2026 | Austin, Texas
Join the waitlist: 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)