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.

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Sales Breakthroughs & In-Person Growth Strategy

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 Jo...

9 Juni 20231h

High status vs. low status customers

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 think...

2 Juni 202359min

Founder Shadowing

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, C...

19 Maj 202350min

Starting Up Sooner vs. Later

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-mark...

12 Maj 202355min

Knowing what we know now...

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 ZipMessa...

5 Maj 202355min

Hangovers & Chaos

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  ...

28 Apr 202350min

Raising Funding (& Pricing)

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 w...

21 Apr 202354min

Artificial Intelligent Business

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 Z...

29 Mars 202352min

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