Bootstrapped Web

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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Top 10 Bootstrapped Web Episodes

Goodpods has curated a list of the 10 best Bootstrapped Web episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to Bootstrapped Web for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite Bootstrapped Web episode by adding your comments to the episode page.

Chicken or Egg Development

Bootstrapped Web

11/11/21 • 30 min

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 Powered By the Tweet This PluginTweet This

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 Powered By the Tweet This PluginTweet This

Resources:

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

The Next Chapter in the Product

Bootstrapped Web

09/10/20 • 45 min

It’s been a little while but Brian and Jordan are back behind the mics. On today’s episode, they’re talking about vacations, a long first week back, marketing, big news with Carthook, cold emails, and guest features. Here are today’s conversation points: Carthook, Shopify, and working together How Shopify works What cold emailers get wrong Conversion … Continue reading

All the Things

Bootstrapped Web

12/10/20 • 48 min

Vote for us on the SaaS Podcast Awards! Jordan and Brian are back with new podcasting gear and set-ups. Today’s topics cover a little bit of everything: from making quality content, to morale boosting Zoom meeting activities. They are also talking about Jordan’s experience working with Shopify, Brian’s 2021 goals for consistency, as well as … Continue reading

Staying positive

Bootstrapped Web

04/29/21 • 46 min

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.

“We need to complement each other more. Because everyone asks for feedback, nobody asks for compliments.” – Jordan

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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

“For founders, literally all we do is solve problems. What’s the next problem to solve? What’s the next thing that’s not working? Every single day.” – Brian

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Resources

ZipMessage

New! zipmessage.com/bootstrappedweb

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

Rally On

Bootstrapped Web

05/20/21 • 58 min

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

“I’m in the middle of that thing that happens if you post a Twitter thread just at the right time. It’s fun. You have to remember to enjoy the fun days. This is one of those fun days.” – Jordan

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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.)

“I’m already all in in terms of hours. But to really go all in, I need a team with me.” – Brian

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Resources:

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Rally On

Josh Pigford’s Maybe company compensation model

Sahil Lavingia on Gumroad’s team model

ProcessKit &...

Tools & People

Bootstrapped Web

09/29/22 • 47 min

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.

“It’s interesting the way we think of tools and how we sell tools to other companies.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation Points:

NoSnow TinyConf
Tools that we use:
- Techstack (Laravel, Angular, React, Ruby on Rails, PHP, Tailwind)
- Project Management (Github, Notion, MixPanel, Confluence, Jira)
  - Marketing Changelog
- Sales, Marketing, and Support (Pipedrive, Asana, Hubspot, Salesforce, Intercom, Customer.io, HelpSpace, HelpScout)
- Metrics and Internal Tracking (Grafana, Profitwell, ChartMogul, MixPanel, Amplitude, Google Analytics, Fathom Analytics, Plausible Analytics)
- Communication (Slack)
Hiring when you’re bootstrapped, versus when you’re funded
- Who to hire first
- Who they are hiring now

“If you can market and get your tool into their hands sometime during that first year of the company, you have such a higher likelihood of getting in. Some of these tools are so sticky.” – Brian Powered By the Tweet This PluginTweet This

Resources:

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

What We’d Build (If Not This)

Bootstrapped Web

09/22/22 • 56 min

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

“Every business that I’ve ever had, has been a reaction to the previous business.” – Brian Powered By the Tweet This PluginTweet This

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

“Having millions of dollars in the bank doesn’t help.” – Jordan Powered By the Tweet This PluginTweet This

Resources:

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

Traction… Then what?

Bootstrapped Web

03/17/22 • 38 min

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.

“All the best paying customers are usually pretty quiet. ” – Brian Powered By the Tweet This PluginTweet This

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

“I highly recommend working with a lawyer that you both trust and like, because there’s some moments out there...” – Jordan Powered By the Tweet This PluginTweet This

Resources:

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

How to Fund a Startup

Bootstrapped Web

10/28/21 • 48 min

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 Powered By the Tweet This PluginTweet This

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 Powered By the Tweet This PluginTweet This

Resources:

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

Should We Rename the Podcast?

Bootstrapped Web

09/30/21 • 41 min

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 Powered By the Tweet This PluginTweet This

Here are today’s conversation points: