Tools & People

Bootstrapped Web
Tools & People
/

What tools do you use for sales and support? Which tools work best for project management? How do you know who to hire first if you’re a bootstrapped company?

Brian and Jordan asked for your questions and Twitter delivered. Today, they are answering Twitter’s questions about what tools they use, and who to hire, and when.  

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

Here are today’s conversation Points: 

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

What We’d Build (If Not This)

Bootstrapped Web
What We'd Build (If Not This)
/

Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet? 

How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or industry right now, what business would you start? Brian and Jordan are answering some of your questions and topics submitted through Twitter. 

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

Here are today’s conversation Points: 

  • Operations versus growth 
    • In SaaS versus as a freelancer
    • What you need to do in order to not interrupt the forward momentum
    • Invite-only feature launch with ZipMessage
    • Does funding really help extend your roadmap?
    • The Catch-22 of growth and operations
  • New and different niches and industries
    • Time away for research
    • AI-driven tech
    • Media businesses in the modern web
      • YouTube, TikTok, OnlyFans, etc.
      • Different use cases for almost anything
    • Separating passion from a career?
  • The formatting of new podcasts
  • Types of tweets and content on Twitter

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Work-Life (Hour-by-Hour), Explained

Bootstrapped Web
Work-Life (Hour-by-Hour), Explained
/

What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at work? What are routines and habits that work for your schedule and team?

Today, Brian and Jordan are talking about their daily routines and how they plan their days around work, their personal life, exercise, and with team members that are scattered all around the globe. They share different time-saving tricks, apps that help hold them accountable to staying healthy, and their opinions on morning productivity and pulling all-nighters.

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

Here are today’s conversation Points: 

  • Rocks, pebbles, and boulders (and hair and sand)
  • Daily routines and how to optimize your day
    • Personal life
    • Professional life
  • Morning productivity versus night owl hours
  • The ultimate productivity app: a notepad and a pen
  • Productivity hours when your team members live in different time zones
  • Separating professional and personal life

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Research, Roadmaps, People, and Product

Bootstrapped Web
Research, Roadmaps, People, and Product
/

How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and professional goals?

After a short but busy couple of weeks, Brian and Jordan are back to talk about updates in their businesses and their lives. Jordan is starting to settle into Chicago and has come up with some interesting revelations. Meanwhile, Brian has also come up with some interesting revelations after listening to and analyzing customer feedback. This has all resulted in a surprising new waypoint on their roadmap.

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

Talking Points: 

  • Jordan’s big move to Chicago
  • Happiness in comparison to other people and the struggles of finding your own path
  • The next iteration of ZipMessage
    • Coaching 
    • Building more features and adapting what we have
  • Hiring, resignations, building up teams and the organization
  • NoCode consultants and solutions businesses

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Company as a Product

Bootstrapped Web
Company as a Product
/

How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features?

There have been plenty of changes with Brian and Jordan since the last episode: moving and changing environments, changing energies, and changing up routines. Today, Brian and Jordan are talking about what they do to stay productive, how their teams are forming and evolving, and what sales in 2022 looks like.

What else should we talk about? What are you hearing (or not hearing from us) that you’d like to know about? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

Talking Points: 

  • Productivity during tumultuous/chaotic personal lives
  • Treating your company like a product
  • Updates with ZipMessage
    • Creating a culture for a team
    • Replacing SEO 
    • Asynchronous updates 
    • Building our own community
    • Announcing features
  • Rally updates
    • Building company culture when you feel too absent
    • SaaS sales in 2022
    • Building teams and laying out playbooks

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Product vs. Pipeline

Bootstrapped Web
Product vs. Pipeline
/

What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product, features, and roadmaps? What do you do when one of your features falls flat?

It’s the middle of the summer edition of Bootstrapped Web. Brian and Jordan are back behind the mic after surviving family vacations, COVID, and cancelled flights. Today, Brian dives deep into repositioning and how ZipMessage has refocused in the past couple weeks. Meanwhile, Jordan talks about the biggest mistake he has made with Rally so far.

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

Talking Points: 

  • ZipMessage and Rally updates
  • The changes in the venture funding and the bootstrapped entrepreneur world
  • Repositioning and refocusing at ZipMessage
    • Different pipelines: influencers, coaches, consultants, etc.
    • Building CRMs (Airtable, Pipedrive)
  • Learning from mistakes
    • Being led by product
  • How Jordan built a stronger working relationship with his team
    • Learning from an existential crisis
  • The truth behind SaaS companies

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Talking to Customers

Bootstrapped Web
Talking to Customers
/

How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products?

It has been a while but Brian and Jordan are back, and they’ve brought updates with Rally and ZipMessage. Jordan talks about his fundraising efforts. Brian talks about his customer research project and what he has learned through that process. 

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

Talking Points:

  • Trends in the industry and the economy
  • Can you avoid consistent churn numbers in new products?
  • Jordan’s fundraising efforts
    • Investor behaviors
    • Are people driven by FOMO
    • The various stages in the funnel
  • Brian’s research project 
    • The lessons that Brian learned
    • What motivates customers and what makes them think?
  • Shifting product features based on the market
    • Learning from other competitors and their customers

Resources:

Brian’s Twitter thread documenting his customer research project

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Marketing in 2022

Bootstrapped Web
Marketing in 2022
/

Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and then do a deep dive on what content marketing will look like in 2022. Recently Aaron Francis (Tuple’s first marketer) talked about their $200,000 loan from Stripe and how he plans on publicly talking about how they will be spending that money. Brian and Jordan give their take on Aaron’s content marketing technique.

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

Talking Points:

  • The timeline for Jordan’s big move
    • What’s it like to sell and buy a house in this market
  • ZipMessage updates
    • Changes on the website
    • Surveys after signing up
    • Coining “ZM”
    • Perfect uses for ZipMessage
    • Hiring strategists for SEO research
  • Traction with Rally
    • Conversations with investors
    • The importance of honesty and “when” to be honest
    • Looking for marketers
  • Tuple’s marketing campaign 

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

CartHook Acquired!

Bootstrapped Web
CartHook Acquired!
/

What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur?

After a brief hiatus, Brian and Jordan are back with some big news: Carthook was officially acquired! Jordan shares what details he can about the acquisition as well as the process and journey of the company.

They also talk about the upcoming MicroConf and what conferences can do for you. After all, they’re not just about networking, there are a lot of things gained when meeting with colleagues, competitors …and podcast listeners.

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

Talking Points:

  • Carthook officially acquired
    • Shutting down and selling the supported Shopify app
    • A mixture of emotions after a crazy journey
  • Unwinding after the stress of a trip
  • What conferences can do to your mindset
    • The energizing effect of conferences
    • Meeting podcast listeners
  • How it feels to be an anonymous company in a space with huge companies
  • Competitors on Twitter: To Mute or Not To Mute
  • How many people do you need for a startup?
  • Access the gratitude

Resources:

Brian on Twitter

Jordan on Twitter

ZipMessage

Rally

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

Traction… Then what?

Bootstrapped Web
Traction... Then what?
/

How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that tell you if you are on the right path? 

As Brian comes back from a vacation and conference (and before Jordan leaves for his own), we’re catching up on the latest updates on ZipMessage and Rally. We’re also talking about how to best judge our own traction, and how to decide which feature to work on first.

Here are today’s conversation points:

  • Staying unplugged during a vacation
  • Recognizing milestones and gauging progress 
  • Updates on ZipMessage and Rally
    • Dealing with big competitors head-on
    • Future plans
  • Being a SaaS business owner and a SaaS customer
  • Integration partnerships: the approaches, the benefits, and the selection process
  • Deciding how to move forward: short term decisions versus long term/strategic decisions

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

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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