[The Struggle] A six-year bootstrapped journey through the Plateau of Doom and back

On this month’s episode of The Struggle, we speak with Janna Bastow, Co-Founder and CEO of ProdPad, a SaaS platform for product management that helps product managers develop product strategy.

It took Janna about a week on the job as a product manager to realize that she didn’t have the tools necessary to do her job. Creating roadmaps, managing a backlog of features and writing specs was all done in Powerpoint and Excel, tools never created for such purposes. Yet for two years that is exactly what Janna used. Until one day she decided she had had enough of waiting for better tools and together with what would become her co-founder, Simon Cast, began building the tool she never had. Initially, Janna and Simon used it just for themselves but it didn’t take long until they realized that many other product managers just like them would find it useful.

In 2012 they quit their jobs and in February 2013 ProdPad was officially launched. They signed their first customer within the month, a customer that is still with them to this day.

However, it hasn’t been all breezy for ProdPad. On the contrary. In the six years since launching, Prodpad has been through the Plateau of Doom and has entertained the idea of VC funding back and forth, ultimately deciding to bootstrap and accepting the challenges that path comes with. The experience comes with many lessons, some regrets, and some mistakes. One thing that has been there from the beginning is the fundamental agreement between Janna and Simon that they were building a business, not a startup. Every decision has stemmed from that.

Like all the other guests on The Struggle, we have the utmost respect for Janna and the fact she never gave in to the struggle but instead always remained aware of why she was doing all this.

You can see Janna and many other incredible founders like her at SaaStock19 in October or if you cannot wait until then, at SaaStock East Coast this June 4-5. They too will share the struggles and the lessons they have picked up from the experience of growing and scaling their SaaS companies. Some of the speakers at SaaStock East Coast include Ragy Thomas, CEO and Co-Founder of Sprinklr, Jonathan Cherki, CEO and Co-Founder, ContentSquare and Julie Weill Persofsky, Partner at Winning By Design. As listeners to the show, you can avail of our 2-for-1 ticket deal. Grab yours now.

Listen to our previous episode with Janna.

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)