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

MADDY-CROSS-PODCAST-BANNER

The Unicorn Hiring Trajectory with Maddy Cross, Notion Capital

Maddy Cross, Talent Director at Notion Capital, is this week’s guest on The SaaS Revolution Show. She talks about Notion’s recent research report: The Unicorn Hiring Trajectory. This looks into the hiring trends of SaaS unicorns compared with other high-performing (but not unicorn) businesses. When Notion invests in a startup, 80% of that capital goes…

DUBLIN, Ireland - 15 October 2019: SaaStock - Day One. (Photo by Dan Taylor - ©Dan Taylor).

How Partnerships Can Help You Scale Your Enterprise Startup

This is a guest post by AWS Startups, who were one of the sponsors at SaaStock 2019. Jonno Southam, Venture Capital Business Development Manager at AWS, and Matillion CEO Matthew Scullion delivered one of the sessions. This article covers the same topic as their talks: how partnerships can help scale your startup. This article was…

DAN-MARTELL-podcast

How to retain top talent with Dan Martell

Dan Martell, five-time SaaS founder and founder of SaaS Academy, talks retaining top talent on this week’s episode of The SaaS Revolution Show. This was his keynote session from SaaStock West Coast 2019. He looks at the main reasons employees leave companies, and gives SaaS founders a strategy for keeping a pulse on your team…