Bootstrapped Web

Bootstrapped Web

Business EN ↓ 172 episodes

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.

Author

Bootstrapped Web

Category

Business

Podcast website

bootstrappedweb.com

Latest episode

May 30, 2026

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Episodes

Staring Reality In The Face 27.10.2023

On today's episode: A few words on world events Brian's runway and strategic planning for 2024 Jordan's reallocating of resources and investment Brian's firing himself from sales Jordan's hiring for sales 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: ...

Product Growth Levers 15.09.2023

On today's episode: When does shipping product lead to growth? Muddy Metrics Sports, exercise, health, eating, and drinking habits Connect with Brian and Jordan: Brian's company,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Jordan's company, Rally Jordan on Twitter:  @jordangal Jordan on Threads:  @jordangal

Getting Outside Help 08.09.2023

On today's episode: How we work with coaches & consultants to guide strategy & implementation UX hangover on shipped features Selling software "once" 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

Context Switching 25.08.2023

On today's episode: How we onboard and activate after a sales call Strategic pricing and show vs. don't show How to think about hiring a sales person Context switching between product work and marketing work as a solo founder.   Connect with Brian and Jordan: Brian's company,  Clarityflow   Brian on Twitter:  @casjam Brian on Threads:  @brian.casel Jordan's company, Rally Jordan on Twitter:  @jord...

Learning to do business (over and over) 11.08.2023

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

An appropriate level of mud slinging 21.07.2023

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

Launching mobile apps, sales cadence, and summer work-life. 07.07.2023

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!

Sales Breakthroughs & In-Person Growth Strategy 09.06.2023

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  

High status vs. low status customers 02.06.2023

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  

Founder Shadowing 19.05.2023

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  

Starting Up Sooner vs. Later 12.05.2023

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     

Knowing what we know now... 05.05.2023

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   

Hangovers & Chaos 28.04.2023

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 )

Raising Funding (& Pricing) 21.04.2023

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 )

Artificial Intelligent Business 29.03.2023

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 )

Websites & Taxes 22.03.2023

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  

ZipMessage has a new name... 14.03.2023

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 )

Putting in the hours 08.03.2023

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 )

All the Things 23.02.2023

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, thank...

Projections… What Are They Good For? 06.02.2023

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 . 

Communicating What's Next 31.01.2023

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...

Product in Market (Is How We Learn) 24.01.2023

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...

Building in public… More. 18.01.2023

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 . 

Another Year 03.01.2023

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 Plugin Tweet This Talking Points:  Viruses, holiday cards, and coming back from vacation 2022 for ZipMessage and Rally...

Hey ChatGPT, what should we talk about? 13.12.2022

We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here . “What can this do? How does this change our product? Does this change things si...

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