Category: Blog

2021/2022 New Year reflections

Bootstrapped Web
2021/2022 New Year reflections
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Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th 🚀 Your comments and feedback on Product Hunt would go a long way today 🙂

To kick off the new year, Brian and Jordan share their 2021 reflections and 2022 goals (or whatever you want to call these ramblings). From moving across the country to managing our mental state to marketing and product growth, it’s all happening in 2022. Let’s do this.

Thanks so much for listening all these years! Here’s to another great year of Bootstrapped Web ahead.

Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Define Traction

Bootstrapped Web
Define Traction
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What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer milestone.

Today’s episode is all about the different ways you can build traction but also the different ways you can define traction.

“If you can work directly with your audience to monetize the people who are crazy about you, you can make more money in a different model, and everyone is the most happy.” – Jordan
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Here are today’s conversation points:

  • Marketing site changes at Rally
    • Getting credit for speed and momentum
    • NFT Projects for marketing
  • ZipMessage website updates
    • Personalization for customers 
    • Creating a WordPress plugin
    • Premium enrollment/Private or public conversations
  • Phases of Product/market Fit
    • What does traction feel like?
    • Are customers willing to adapt for your product?

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

“We did things a certain way and, if they didn’t like that, either they didn’t become a customer or they adapted. And we had plenty of customers who adapted.” – Brian
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Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

The Chaos

Bootstrapped Web
The Chaos
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Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do you reach a niche market? Jordan and Brian talk about these questions and more on this episode of Bootstrapped Web. 

Jordan talks about his hangups and why his need for idea exploration is causing difficulties with his leadership team. Meanwhile, Brian is continuing to navigate the challenges of starting a new business with a niche target market. Is podcasting the answer? They also go over some interesting tools for searching for the perfect podcast, marketing to specific groups, as well as their excitement for Andrew Chen’s newest book, “The Cold Start Problem.”

“I’m very much a middle sibling when it comes to management at the leadership level. It’s very collaborative.” – Jordan
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Here are today’s conversation points:

  • A new ZipMessage website
  • Hiring generalists or specialists
  • Challenging leadership team conversations
  • Marketing and and outreach for the podcasting community
    • Influencer outreach
    • SEO plays and search demands
  • Andrew Chen’s newest book release

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

“I’m getting these things dialed in. It’s difficult but I think it’s finally starting to come together.” – Brian
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Resources:

SparkToro

Podseeker

“The Cold Start Problem: How to Start and Scale Network Effects” by Andrew Chen

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

Chicken or Egg Development

Bootstrapped Web
Chicken or Egg Development
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When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities?

Brian and Jordan talk all about the newest updates with ZipMessage and Rally. From experimenting with free plans, website redesigns, and preparing themselves for an influx of activity, there is a lot going on behind the scenes. Exciting things are happening but with excitement come daunting tasks, important decisions, and possible mistakes.

“What we’re about to do is, we’re about to scramble people’s priorities in a challenging way.” – Jordan
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Here are today’s conversation points:

  • New activity with ZipMessage
  • Onboarding first merchants with Rally
    • Remembering the excitement and joy that comes from sales demos
  • Experimenting with a free plan on ZipMessage
    • The differences between the free and paid plan
  • Rally’s all-hands to mentally prepare for a different challenge: new priorities
  • ZipMessage’s website redesign
  • The daunting task of revamping landing pages

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

“Nothing like having real customers to really drive what’s really important.” – Brian
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Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally

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

How to Fund a Startup

Bootstrapped Web
How to Fund a Startup
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Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which funding path should you take? What does it mean for a fund to lead a round? 

Meanwhile, Brian gives updates on ZipMessage including marketing projects (comparison/competitor pages), hiring designers for website redesigns, and falling behind on content.

“What we did was, we only worked with seed funds, because I wanted everyone to be focused on success at the seed stage.” – Jordan
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Here are today’s conversation points:

  • Rally funding announcements
  • Planning for funding and growth for Rally
  • Strategic funding approaches and plans
  • Comparison/competitor pages
  • Website redesigns
  • SEO content opportunities for ZipMessage
  • How to get the right response and the right person for the job

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

“In this early stage, there is an element of creativity and strategy. I have to bring that knowledge to the project. I can’t just hand that off to someone else.” – Brian
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Resources:

Brian on Twitter

Jordan on Twitter 

ZipMessage

Rally Website

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

Go to Market vs. Marketing

Bootstrapped Web
Go to Market vs. Marketing
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What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, content strategists, and updates on where they are with their Rally and ZipMessage.

Jordan talks about Rally’s methodical blog posts, which will be released slowly over the next few months. Brian shares some of the new features on ZipMessage and his plans for ‘going to market.’ They also talk about how uncomfortable and rewarding the process can be. ‘Going to market’ is humbling and requires authenticity after all.

“There’s a lot going on inside the company and inside the product. And ‘go to market’ is one element of that but you can’t just focus on that because there’s a lot of other things going on that we have to get right.” – Jordan
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Here are today’s conversation points:

  • The difference between going to market and marketing
  • What is involved when you go to market
  • Marketing techniques and content creators
  • Different versions of networking

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

“It’s this idea (especially in the first year) where you’ve got to be doing activities that are introducing the product to more and more new people.” – Brian
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Resources:

Brian on Twitter

Jordan on Twitter 

Rally

ZipMessage

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

Should We Rename the Podcast?

Bootstrapped Web
Should We Rename the Podcast?
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Bootstrapped Web is no longer bootstrapped, on either side!

Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses, and the importance of developing a unique view of the market.

Brian takes funding from Calm Fund (formerly Earnest Capital), which has been a month in the making. He talks about the different decisions and considerations to be made when exiting Audience Ops and taking funding for ZipMessage.

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

“I love this [angel funding] ecosystem and how it’s been evolving.” – Brian
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Here are today’s conversation points:

  • Jordan’s “coming out” strategy for Rally
  • Brian takes funding from Calm Fund (formerly Earnest Capital)
“I have been sitting on so many secrets, it’s not healthy. It’s not healthy to be quiet and fearful. It’s not my natural state.” – Jordan
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Resources

Rally Blog

“Your Startup is a Movement” by David Sacks

Calm Fund 

Brian on Twitter

Jordan on Twitter 

ZipMessage

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

Audience Ops Changes Hands

Bootstrapped Web
Audience Ops Changes Hands
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Some news!  Brian has sold his business, Audience Ops, to JD Graffam!  And what better way to announce this transition than to bring JD on the show!  

Jordan leads the way as Brian and JD talk through how this deal came together, the process from each of their perspectives, and the successful close and transition that’s now underway.

If you’re thinking about pursuing an exit from your business or thinking about acquiring one, we hope you’ll find some of our real-world experience from this deal helpful.

You can read Brian’s blog post that dives deeper into the deal and thought processes that led up to the exit.

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

Mentioned on today’s episode:

Audience Ops

JD Graffam on Twitter

JD’s article, Fourteen Things That Will Keep Me from Buying Your App

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

Marketing ideas

Bootstrapped Web
Marketing ideas
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Introduction:

Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendous heatwave. Today’s topics range from admin and accounting tasks they would rather avoid, their very professional podcasting process, Rally’s current markers and goals, and Brian’s exciting marketing ideas. 

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

“Something didn’t sit right. It wasn’t ambitious enough. We need to challenge ourselves more.” – Jordan
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Here are today’s conversation points:

  • Forming a new corporation with ZipMessage
    • The need for full-service accounting/admin
  • Our “professional” podcasting process
    • Listening back on episodes to help sharpen your gut
  • Rally’s current markers
    • Do we have what we need to raise money?
    • Working backwards from and mapping out the goal and markers
    • How to project numbers at this stage
    • Creating a safe space to make mistakes, changing your mind, and getting appropriate push-back
  •  Marketing ideas and promotion
    • The Shipped Podcast (using ZipMessage)
    • Testing audiences and different marketing platforms
    • Podcast sponsorships: targeting small podcasts
    • YouTube advertising
    • Alternative free trial program
“Let’s not think of the worst case scenario but the realistic scenario.” – Brian
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Mentioned on today’s episode:

Office Engine

Gusto

Leave us a message here

Rally On 

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook  

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

Back and Running

Bootstrapped Web
Back and Running
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After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “common, everyday tools” to people outside of the SaaS community.

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

“Growth as headcount as an acceptable growth metric. And the reason for that is if you’re not shooting for
profitability and you’re shooting for milestones.” – Jordan
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Here are today’s conversation points:

  • The relationship between founder and VC
    • Headcount versus profitability as growth
    • Hiring a recruiter
  • ZipMessage goals
    • Prioritizing requests
    • Setting up new features
    • Opening it up to the public
    • The Shipped podcast
    • Brian’s new technical marketer
  • Introduction of technology to others
    • Niche tools
    • Summit, whiteboards that do math. The easiest way to create, test, and present your logic.
  • Taming the chaos
“If profitability isn’t the goal on this path (which makes sense), what are the metrics that you’re looking at for the next 12 months or 18 months?” – Brian
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Mentioned on today’s episode:

Leave us a message here

Rally On 

ZipMessage

SunriseKPI 

Productize 

Audience Ops

ProcessKit  

Carthook  

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