Bootstrapped Web | For Entrepreneurs Bootstrapping Web Startups | Interviews & Business Case Studies  show

Bootstrapped Web | For Entrepreneurs Bootstrapping Web Startups | Interviews & Business Case Studies

Summary: 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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Podcasts:

 ZipMessage has a new name... | File Type: audio/mpeg | Duration: 00:53:55

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.

 Putting in the hours | File Type: audio/mpeg | Duration: 0:00:00

Jordan and Brian both feel overworked this week. Putting in more hours than usual, and more importantly, strategizing on which priorities get those hours.

 All the Things | File Type: audio/mpeg | Duration: 00:44:22

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. 

 Projections… What Are They Good For? | File Type: audio/mpeg | Duration: 00:49:18

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. 

 Projections… What Are They Good For? | File Type: audio/mpeg | Duration: 00:49:18

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 | File Type: audio/mpeg | Duration: 00:47:40

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, … Continue reading Communicating What’s Next

 Communicating What's Next | File Type: audio/mpeg | Duration: 00:47:40

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. 

 Product in Market (Is How We Learn) | File Type: audio/mpeg | Duration: 00:53:38

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. | File Type: audio/mpeg | Duration: 00:54:59

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 | File Type: audio/mpeg | Duration: 00:46:39

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. 

 Hey ChatGPT, what should we talk about? | File Type: audio/mpeg | Duration: 00:56:05

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 significantly enough that we should come off our roadmap?” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The future of AI and creators Q4 spreadsheets and budgeting Updates in Rally and ZipMessage SEO content Marketing and sales Product-led content “If we’re not working on those growth graphs, I don’t feel comfortable. But, at the same time, I need to work more on the product” – 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. 

 Twitter Takes (and Some Business Talk) | File Type: audio/mpeg | Duration: 00:53:07

Our obligatory take on Twitter in the Elon era.  Also: SEO, board meetings, and growth targets.  What are your thoughts on Twitter in the time of Elon? How do you run your board meetings? When it comes to growth targets, where do you focus your energy?  If you have any questions, comments, or topic ideas … Continue reading Twitter Takes (and Some Business Talk)

 Twitter Takes (and Some Business Talk) | File Type: audio/mpeg | Duration: 00:53:07

Our obligatory take on Twitter in the Elon era.  Also: SEO, board meetings, and growth targets.  What are your thoughts on Twitter in the time of Elon? How do you run your board meetings? When it comes to growth targets, where do you focus your energy?  If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “The more Twitter is in everyone’s everyday lives, the more leverage Twitter and Elon have to start taking marketshare in these parts of life.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: The conclusion of Jordan’s moving sagaThe new era of TwitterVerificationTwitter as a productBuilding in publicTeam retreats and all-hands meetingsZipMessage updatesSEO: quantity, speed, and AI toolsBoard meetings and keeping recordsGrowth Targets “I would love to build a culture where anyone in the company can say, ‘I think we’re focusing on this thing when we shouldn’t’ or ‘I think we’re missing this entirely.’” – Jordan Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitt

 Q4 Energy | File Type: audio/mpeg | Duration: 00:50:35

Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are underway in Q4. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. Here are today’s conversation points: NoSnowTinyConf Recap Residual issues that arise after … Continue reading Q4 Energy

 Q4 Energy | File Type: audio/mpeg | Duration: 00:50:35

Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are underway in Q4. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “The single, most important element was… record your demos.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: NoSnowTinyConf RecapResidual issues that arise after raising fundsRally updatesLaunch of Coach Club and Coach Club DigestTreating marketing as a productTeam updates, accountability, and weekly stand-ups “[I love] approaching marketing like its a product in itself.” – Brian Powered By the Tweet This PluginTweet This Resources: Coach Club 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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