Yesware: Coping with the everyday struggles on the way to $20M+ ARR2 min read

Matthew Bellows the Struggle.001

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, buy sildenafil 50 mg 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 our 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]

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

Speaker Announcements-5

Hidden Gems: The Rising Star Speakers of SaaStock19

We’re at a distinct turning point in the year. There’s a slight chill in the morning air, the shops are stocking up on knitwear, and Instagram is overflowing with #pumpkinspice everything. For some, this means the onset of Fall. For anyone working in the SaaS space, it can mean only one thing; SaaStock19 is just…

how to grow a prize kabbage-2

How To Grow A Prize Kabbage: Culture, Change and Capital with Kathryn Petralia

Although impeccably polite, you get the impression that Kathryn Petralia might be a little tired of the focus placed on her unconventional path to success at the helm of FinTech giant, Kabbage. The company, which provides AI-powered access to capital, directly to SMBs, has ranked on the Inc. 5000 list as one of America’s fasting-growing…

Jason VandeBoom.001

Break all the rulebooks: How ActiveCampaign reached $70M in ARR

On this week’s episode of the SaaS Revolution Show, we speak with Jason VandeBoom, Founder and CEO of ActiveCampaign about all the unusual things he has done to reach $70M in ARR and counting. A builder and maker of things from an early age, young Jason thought that the best way to cater for that…