Category: Blog

Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor lacrosse injury, they both gush over Matt Medeiros, and give updates on their latest business endeavors. They talk about the progress on the search for a media creator for both Rally and ZipMessage, hiring funnels and hiring hurdles, getting feedback, and ways to get out of a funk.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. 

Here are today’s conversation points:

• Matt Medeiros and the media creator role
• The technical side of ZipMessage
• Reading stats and getting feedback
• Getting out of a funk
• Completing tasks, self-induced stress, and forgiveness
• Figuring out the right workflow and the right people
• Hiring funnels, hurdles, testimonials, and role-specific adjustments

Mentioned on today’s episode:

Matt Medeiros’ Twitter Thread on the media creator role

ChartMogul

DynamiteJobs

Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull and Amy Wallace

Rally On 

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook  

Brian’s 2 positions open for applications:

Media Creator

Technical Marketer

Leave us a message here

As always, thanks for tuning in. Head here to leave a review on iTunes. 

Brian and Jordan are back with updates about diving headfirst into team sports with an “old man lacrosse leagues,” to celebrating 10-year wedding anniversaries, job postings, and creating messages that resonate with customers. They’re covering a little bit of everything today.

Brian shares a couple of interesting job openings based on ZipMessage: a media creator and a technical marketer. Check out the job opening for media creator if you love to create content, are comfortable telling stories, and coming up with creative new ideas. He is also looking for a technical marketer who will work on distribution and optimizing channels and SaaS funnels. If you are interested in either job position, use the links below to apply.

Media Creator  

Technical Marketer

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message here

Here are today’s conversation points:

• ZipMessage Updates:
  • Growth and skepticism 
  • Job openings:
    • Media creator
    • Technical marketer
• Creating a community
• The Bloomberg Model
• Axios
• Conversations and conveying the Rally message
  • What to lead with
  • How to make your message resonate
• Shopify opinions
• Brian is hiring for 2 roles:

Media Creator  

Technical Marketer

Mentioned on today’s episode:

Axios Today

Rally On 

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook  

Leave us a message here

As always, thanks for tuning in. Head here to leave a review on iTunes. 

Brian and Jordan are back with no excuses and plenty of updates for both Rally and ZipMessage. Today’s topics are all about roadmaps, leading tech teams, and ecommerce marketing. While ecommerce has been around for a while, SaaS is evolving in the way it is marketed and sold. What are your thoughts on SaaS marketing strategies? Do you prefer leading a large tech team or would you rather keep your team small and easily manageable? What are your thoughts on the importance of communication for teams who work remotely?

If you have any questions, comments, or topic ideas for Brian or Jordan, leave a message here.

Here are today’s conversation points:

• The next step for Rally
• The many uses for ZipMessage
  • Combining live Zoom calls with asynchronous follow-ups
  • Direct Slack integrations
  • The ZipMessage roadmap
• Leading a tech team
  • Requirements for leadership
  • The importance of communication
• Different strategies for marketing

Mentioned on today’s episode:

Patrick Campbell’s tweet about building a media brand, monetizing with software

Unthinkable podcast by Jay Acunzo

Our stuff:

Rally On 

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook

Leave us a message here

It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also get into a few updates with ZipMessage. Brian talks about the possibility of building a small team and the stigma around hiring a team full of contractors. 

Are you a freelancer looking for a little work? Are you a marketing specialist? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

Here are today’s conversation points:

• Rally and RallyOn.com
  • What does Rally do for customers?
  • What does it mean to go headless?
  • Definition of “Modern brands”
  • What makes Rally different?
• Enjoying and being in the moment
• The importance of elevator pitches and headlines
• Multiple fits and building relationships
• The next step and roadmap for Rally
• ZipMessage updates
  • Doing everything yourself vs. building a small team
  • Contractors and freelancers vs. employees
  • The stigma behind hiring overseas 
• Creating your perfect company culture 
• Brian’s marketing talent wishlist:
  • Technical marketer (Google analytics, SEO, etc.) 
  • Media producer (podcasting, interviews, etc.)

Resources:

Leave us a message here

Rally On 

Josh Pigford’s Maybe company compensation model

Sahil Lavingia on Gumroad’s team model

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook  

As always, thanks for tuning in. Head here to leave a review on iTunes. 

Brian and Jordan are back behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch for a new product. How do you decide if this new project is worth it? How do you find people who are as excited about it as you are? 

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb.

Here are today’s conversation points:

• Project and business updates: marketing, development, and not moving fast enough
• Talking with partners and agencies versus potential customers
• Taking a position and what that means for a business
• How to decide whether a project or a product is worth the time?
• The Catch-22 of starting and growing a new business
• How to evaluate a “head-of-growth” expert
• Pivotal moments in ZipMessage and secret projects
• Growth hacks for ZipMessage

Resources:

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook  

As always, thanks for tuning in. Head here to leave a review on iTunes. 

Brian and Jordan are back with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typical Bootstrapped Web episode. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb.

Here are today’s conversation points:

• Updates on Jordan’s secret product
• Feeling down and (surprising) external motivators
• What founders do and the meaning of being a founder
• The importance of compliments and empathy
• Updates, changes, and uses for ZipMessage
• Framework and patterns in successful niche SaaS products
  • Three-phase process: enter, lean-in, all-in

Resources

ZipMessage

New! zipmessage.com/bootstrappedweb

Productize 

Audience Ops

ProcessKit  

Carthook

As always, thanks for tuning in. Head here to leave a review on iTunes.

Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and concerts). They also spend a little time talking about Josh Pigford’s amazing public journey, from exiting Baremetrics to starting his own company for modern financial planning & wealth management. How do you handle your professional persona? Are you an open book on your social media accounts? Are you strategic about what you post? Brian and Jordan discuss Josh’s strategic and surprisingly open discussions on Twitter and how they differ in their social media personas.

Here are today’s conversation points:

• The roller coaster of ZipMessage onboarding
• Finalizing copy and launching landing pages
• Audience Ops team changes and transitions
• The vision at Audience Ops
• Expectations, emotions, and performative reactions during Monday morning calls
• The importance of understanding the “Why”
• Josh Pigford’s exit from Baremetrics and his professional trajectory…in public
• Angel investing and asking for money

Resources

Maybe.co

Josh Pigford’s Twitter

ZipMessage

SunriseKPI

Productize

AudienceOps

ProcessKit

Carthook 

As always, thanks for tuning in. Head here to leave a review on iTunes.

Will this be the week that Jordan finally gets to talk about crypto? In this episode of Bootstrapped Web, Brian and Jordan give us some updates on their businesses. Is Brian running late with ZipMessage? What has been going on behind the scenes of Jordan’s secret project? They also talk indepth about discipline and productivity. Do working sessions help? When is it better to work alone? What tools do you use to hold yourself (and others) accountable?

Here are today’s conversation points:

• Progress with ZipMessage
• Jordan’s three different profiles of potential partners he is looking to next
• The outreach plan for Jordan’s secret project
• Brian’s mental deadlines: Is ZipMessage falling behind?
• Know Thyself: a lack of discipline around productivity
  • Working sessions vs working alone
  • Tiny little dependencies that get overwhelming
  • Creative-Technical-Designer-Founder-Entrepreneur deep work sessions
• Personal and professional goals
• Why things are happening a certain way and why things feel inevitable
  • Building toward that inevitability (but not too early)

Resources

Todoist

ZipMessage

SunriseKPI

Productize

AudienceOps

ProcessKit

Carthook 

As always, thanks for tuning in. Head here to leave a review on iTunes.

This is two weeks in a row for Brian and Jordan. In today’s episode they’re talking about new toys and tools, Twitter drama, and business talk, specifically Jordan’s newest team member and Brian’s newest product. April 5th is going to be a big week for both Brian and Jordan when it comes to business news.  They also successfully avoid having Jordan talk about crypto for another episode. How long will they be able to go without talking about it?

Here are today’s conversation points:

• Regulation crowdfunding ceilings
• SaaS and tech people and temperaments on Twitter
• Updates on ZipMessage
  • Nine simple reasons why Brian loves and is launching ZipMessage
  • It’s sharable and boastable
  • Brainstorming ideas for a viral launch
• Arrows.to’s launch strategy
• Jordan’s new chief-of-staff started, which has led to a productive week
  • Easier to do things when you’re being held accountable
  • Writing content, then handing it over to a copyeditor to tighten the drafts
  • Rearranging the sequence of rollout

Resources

ZipMessage

SunriseKPI

Productize

AudienceOps

ProcessKit

Carthook 

As always, thanks for tuning in. Head here to leave a review on iTunes.

Officially a year after the pandemic started, Brian and Jordan do a bit of reminiscing and chatting about vaccine news before diving into updates about work. Not to mention, Jordan gets his first real haircut of the year.

On the business front, things are moving (slow and steady) for Brian. ProcessKit has accumulated a decent amount of data which means that he can start making data-driven decisions for the business. While ZipMessage is still new and in the early stages of the process. Jordan talks about the change in his mindset from Carthook to his new project. Meanwhile, Brian talks about delegating tasks, what it means to “hire to collaborate,” and the things he’s doing in order to build his rhythm with ProcessKit and see progress.

Here are today’s conversation points:

• The shift in temperance about the ongoing pandemic
  • Vaccines and vacations
• Changing your mindset: going from bootstrap to VC
  • How that affects your appetite for risk
• Delegating tasks to people now and hiring to collaborate
  • Hiring freelancers
  • Finding talented people who don’t want to be full time employees
  • Stories (success and otherwise) with freelancers
• New trends with sales since Jordan started Carthook
  • What do you do with marketing, prelaunch?
• ProcessKit updates
  • In-app onboarding flow is helping self-conversion
  • Is patience the key?
  • Home page content about customer on-boarding and niches
  • Testing headlines and swapping out pages to test data and changes in customer trends
  • The possibility of launching a new version versus launching new features

Resources

ZipMessage

ProcessKit

AudienceOps

Productize

SunriseKPI

Carthook 

As always, thanks for tuning in. Head here to leave a review on iTunes.