
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

Aug 11, 2023 • 57min
Learning to do business (over and over)
On today's episode:
Building in public. Why and how?
Learning sales. Process, strategy, tactics.
How we learn and implement.
A solo founder's dillemma
Connect with Brian and Jordan:
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal
Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Jul 21, 2023 • 49min
An appropriate level of mud slinging
On today's episode:
How do we think about runway and profitability?
What's an appropriate level of mud throwing?
Should founders spend time on personal brand?
Connect with Brian and Jordan:
Brian's company, Clarityflow
Brian on Threads: @brian.casel
Brian on Twitter: @casjam
Jordan's company, Rally
Jordan on Threads: @jordangal
Jordan on Twitter: @jordangal

Jul 7, 2023 • 58min
Launching mobile apps, sales cadence, and summer work-life.
On today's episode:
Brian's back from Asia (did he stop working?)
Launching the Clarityflow app on iOS and Android (check the video)
Jordan's shifting the sales process & sequence
What it takes to close larger deals
Connect with Brian and Jordan:
Jordan's company, Rally
Jordan on Twitter: @jordangal
Brian's company, Clarityflow
Brian on Twitter: @casjam
Yo! We're on Threads too!

Jun 9, 2023 • 1h 1min
Sales Breakthroughs & In-Person Growth Strategy
On today's episode:
The value of in-person relationship building
The murky side of MRR growth
Transparency with our teams
PGA & LIV, Apple Vision Pro and other sidetracks!
Connect with Brian and Jordan:
Brian's company, Clarityflow
Jordan's company, Rally
Brian on Twitter: @casjam
Jordan on Twitter: @jordangal

Jun 2, 2023 • 59min
High status vs. low status customers
What (and when) is a SaaS "feature complete"?
How do we sell and negotiate mid-market contracts?
How to please customers (and which ones are worth pleasing)?
...And other tricky questions we're thinking about this week.
Connect with Brian and Jordan:
Brian's company, Clarityflow
Jordan's company, Rally
Brian on Twitter: @casjam
Jordan on Twitter: @jordangal

May 19, 2023 • 50min
Founder Shadowing
Founder shadowing (make it a thing?)
chatGPT vs. hiring a writer
Go to market strategy
Dialing in ICP
What is marketing, really?
Follow Brian and Jordan:
Jordan's company, Rally
Brian's company, Clarityflow
Jordan on Twitter
Brian on Twitter

May 12, 2023 • 56min
Starting Up Sooner vs. Later
Brian and Jordan give their takes on the question of whether to start up your first business earlier vs. later in life.
Plus: Board meeting takeaways, MRR growth, sales demos, enterprise vs. mid-market, and BBQ smokers.
Brian's business: Clarityflow (formerly ZipMessage )
Jordan's business: Rally
Follow us on the Twitters: @jordangal & @casjam

May 5, 2023 • 55min
Knowing what we know now...
What would we have done differently if we started Rally or Clarityflow over again? We get into that and other questions from Twitter. Keep em coming!Brian's business: Clarityflow (formerly ZipMessage) Jordan's business: Rally
Follow us on the Twitters: @jordangal & @casjam

Apr 28, 2023 • 51min
Hangovers & Chaos
Brian's taming the chaos of inbound customer growth mixed with urgency to ship. Jordan's experimenting with 2 go-to-market strategies, one for enterprise, one with partners.Jordan's business, Rally
Brian's business, Clarityflow (formerly ZipMessage)

Apr 21, 2023 • 54min
Raising Funding (& Pricing)
Jordan announces Rally's Series A and we unpack the whirlwind road that it took to get there.
Brian launched a pricing increase, which coincided with a competitor's unexpected shut down.
It's been a wild few weeks while we've been off, but we're back!
Jordan's business, Rally
Brian's business, Clarityflow (formerly ZipMessage )
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