[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 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)