
Bootstrapped Web
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.
Latest episodes

Mar 29, 2023 • 53min
Artificial Intelligent Business
Random thoughts on what's happening in AI and startups. Jordan and co move to self-signups. Brian and co work on marketing projects.
Jordan's business, Rally
Brian's business, Clarityflow (formerly ZipMessage)

Mar 22, 2023 • 46min
Websites & Taxes
Both Jordan and Brian are in the thick of redesigning their SaaS websites. Plus some tax talk.
Jordan's business, Rally
Brian's business, Clarityflow (formerly ZipMessage)
Learn about Section 174 tax issue for software businesses and join in the effort to repeal at ssballiance.org

Mar 14, 2023 • 54min
ZipMessage has a new name...
Brian shares the news rebranding ZipMessage to a new name and the transition roadmap ahead... And the new name is...Jordan and team step away to a conference while go-to-market heats up.Oh yeah, and recorded on the day the Silicon Valley Bank saga unfolded in realtime... So that was a (and scary) discussion.
Jordan's business, Rally
Brian's business, Clarityflow (formerly ZipMessage)

Mar 8, 2023 • 30min
Putting in the hours
Jordan and Brian both feel overworked this week. Putting in more hours than usual, and more importantly, strategizing on which priorities get those hours.
Jordan's business, Rally
Brian's business, Clarityflow (formerly ZipMessage)

Feb 23, 2023 • 44min
All the Things
Another week in the chaos that is startup land for Brian and Jordan. Topics include:
Starting and finishing our day
Managing focus through daily distractions
Delegating strategy and teeing up for results
And other rants… You know the drill
Hit us on Twitter @casjam @jordangal with feedback on what we should talk about next week!
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.

Feb 6, 2023 • 49min
Projections… What Are They Good For?
The episode streak continues! Brian’s product design process, Jordan’s annual budget meeting (and takeaways), outbound vs. inbound marketing, and an interesting discussion around the usefulness of projections.
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.

Jan 31, 2023 • 48min
Communicating What's Next
This week, Brian and Jordan yap about:
– Strategic partnerships
– Pricing on transactions
– Communicating company direction (internally)
– Developer-focused content
– …Creatine pills?
We’re running out of ideas! Hit us up on Twitter (@casjam, @jordangal) and tell us what we should talk about.
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.

Jan 24, 2023 • 54min
Product in Market (Is How We Learn)
Back for our weekly founder therapy session, err… podcast episode
Here’s what’s up this week:
– Brian (finally) ships sub-threads in ZipMessage
– Jordan’s hiring an SDR
– Learning from strategic decisions that went wrong
– Product insights with vs without a product in market
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.

Jan 18, 2023 • 55min
Building in public… More.
We kick off 2023 with a grab bag of topics:
– Jordan’s building in public more
– Brian’s building solo with contractors
– Headless ecom becoming “a thing”
– ChatGPT is firmly in Brian’s coding workflow
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.

Jan 3, 2023 • 47min
Another Year
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on…
Thanks for listening and for sticking with us another year on Bootstrapped Web.
“Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This PluginTweet This
Talking Points:
Viruses, holiday cards, and coming back from vacation
2022 for ZipMessage and Rally
Lack of product-market fit
Tim Ferriss’ Fear Setting
The Ten-Year Business
Staying “based” and staying true to your vision
Themes and goals for 2023
Building features specifically for specific markets
“The first year [for Zipmessage] was a dream and the second year was more bumpy and challenging.” – Brian Powered By the Tweet This PluginTweet This
Resources:
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
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