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

ZipMessage has a new name...

Bootstrapped Web — Tue, 14 Mar 2023 22:45:13 +0000

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

Bootstrapped Web — Wed, 08 Mar 2023 17:30:09 +0000

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

Bootstrapped Web — Thu, 23 Feb 2023 13:58:30 +0000

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!

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

Projections… What Are They Good For?

Bootstrapped Web — Mon, 06 Feb 2023 22:49:47 +0000

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.

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

Communicating What's Next

Bootstrapped Web — Tue, 31 Jan 2023 22:11:53 +0000

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.

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

Product in Market (Is How We Learn)

Bootstrapped Web — Tue, 24 Jan 2023 19:24:52 +0000

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

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

Building in public… More.

Bootstrapped Web — Wed, 18 Jan 2023 00:25:34 +0000

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

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

Another Year

Bootstrapped Web — Tue, 03 Jan 2023 21:22:15 +0000

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

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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

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Resources:

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

Hey ChatGPT, what should we talk about?

Bootstrapped Web — Tue, 13 Dec 2022 20:11:56 +0000

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

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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

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Resources:

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

Twitter Takes (and Some Business Talk)

Bootstrapped Web — Wed, 09 Nov 2022 21:44:46 +0000

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

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Here are today’s conversation points:

The conclusion of Jordan’s moving saga
The new era of Twitter
- Verification
- Twitter as a product
- Building in public
Team retreats and all-hands meetings
ZipMessage updates
SEO: quantity, speed, and AI tools
Board meetings and keeping records
Growth 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

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Resources:

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

Q4 Energy

Bootstrapped Web — Mon, 17 Oct 2022 22:31:11 +0000

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

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Here are today’s conversation points:

NoSnowTinyConf Recap
Residual issues that arise after raising funds
Rally updates
Launch of Coach Club and Coach Club Digest
Treating marketing as a product
Team updates, accountability, and weekly stand-ups

“[I love] approaching marketing like its a product in itself.” – Brian

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Resources:

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

Tools & People

Bootstrapped Web — Wed, 28 Sep 2022 18:45:29 +0000

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

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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

Resources:

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

What We'd Build (If Not This)

Bootstrapped Web — Tue, 20 Sep 2022 22:05:54 +0000

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

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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

Resources:

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

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

Bootstrapped Web — Thu, 08 Sep 2022 18:27:59 +0000

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

“I have some real issues with the morning. I’m not very productive in the morning.” – Jordan

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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

“I”m very much a morning person. I like waking up relatively early but these people with the 5AM and 4AM wake-ups seem just a little bit extreme to me.” – Brian

Resources:

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

Research, Roadmaps, People, and Product

Bootstrapped Web — Wed, 31 Aug 2022 22:41:24 +0000

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

“That’s the thing that keeps me unemployable, really, is that I own my own business and what I’m building here is an asset that will result in a much bigger win down the road.” – Brian

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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

“The environment has a big impact on the conversation that I’m having in my head about ambition, money, business, and that soup.” – Jordan

Resources:

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

Company as a Product

Bootstrapped Web — Wed, 10 Aug 2022 18:46:37 +0000

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.

“The economy is going to do what it’s going to do. There’s not much we can do about that except work on the things we can control.” – Brian

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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

“The market shifted but it didn’t implode. It’s not like everything is over. Everything feels a little more serious right now.” – Jordan

Resources:

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

Product vs. Pipeline

Bootstrapped Web — Mon, 11 Jul 2022 17:54:19 +0000

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

“It went from, everyone’s growing and there’s plenty of money to fund what you want to do to, all of a sudden, the water went back out and it turns out a lot of people don’t have pants on.” – Jordan

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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

“It doesn’t make sense to focus on product unless we have a daily pipeline that is ready to present that product too.” – Brian

Resources:

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

Talking to Customers

Bootstrapped Web — Tue, 07 Jun 2022 22:26:32 +0000

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

“It went from, ‘This is going to be a piece of cake’ to… ‘That’s not what’s going on in the market.’” – Jordan

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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

“When you actually talk to [a customer], you not only learn a ton, it also helps me emotionally and mentally” – Brian

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Resources:

Brian’s Twitter thread documenting his customer research project

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

Marketing in 2022

Bootstrapped Web — Thu, 28 Apr 2022 10:22:54 +0000

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

“You can make it happen, but not really. Your customers make it happen.” – Jordan

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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
- Aaron Francis as Tuple’s first marketer
- Aaron’s tweet about their $200,000 loan from Stripe

“When a customer explains the whole value prop, it gives me so much more energy.” – Brian

Resources:

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

Traction... Then what?

Bootstrapped Web — Fri, 08 Apr 2022 14:33:57 +0000

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

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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

Resources:

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

Everything Must Go

Bootstrapped Web — Fri, 08 Apr 2022 13:39:03 +0000

We have some big news to share before we go on a (much needed) two-week hiatus.

Brian talks about his sale of Productize, in addition to nearly every other business he has owned. Jordan talks about his latest tweet thread, responding to Moiz Ali’s criticisms of Shopify. We also talk about the power of audio, networking through podcasting, and marketing.

“The relationship built through audio is so much more powerful. It’s really hard to do that with copywriting, with a website, with ads. It’s just much harder to do.” – Jordan

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Here are today’s conversation points:

Taking a break and staying away from the computer while on vacation
Moiz Ali’s tweet about Shopify’s problems
- The problems that they need to solve
Marketing and speaking your mind
The sale of the Productize brand (and everything else)
Networking through podcasting
- Connecting with people through audio
Competitors and marketing

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

“I would focus on one thing at a time, but (in my experience) it’s not the end of the world to have a few different things going and learn and hone different types of chops and skillsets and meet different people.” – Brian

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Resources:

Jordan’s response to Moiz’ Shopify Tweet

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

CartHook Acquired!

Bootstrapped Web — Wed, 06 Apr 2022 18:55:33 +0000

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

“The thing that I want out of a conference is a huge boost of confidence.” – Jordan

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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

“Since Day 1, we’ve had a fundamental difference of what ZipMessage is and that’s the intake ability.” – Brian

Resources:

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

Tokenizing

Bootstrapped Web — Tue, 22 Feb 2022 19:43:03 +0000

How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology?

Today, we’re talking about marketing, hiring developers and writers during “The Great Resignation,” and tokenizing. Token-based economics is the future of SaaS. Web3 tech isn’t just in the future, it’s happening right now.

“I would aim for zero commercial partnership: no rev share either way. Those are the best partnerships.” – Jordan

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Here are today’s conversation points:

Dealing with bad days, finding additional sources of joy
Big Snow Tiny Conf (East)
Marketing: calming down after product launch and initial promotion
- Integrations and examples of
- Writing and promotion
Fundraising and tokenizing
- Adopting web3 technology
Transitioning between developers during “The Great Resignation”

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

“I’m so excited to be a part of this podcast now. I feel like I get a front row seat and I’m slowly starting to see how Web3 actually starts to change things.” – Brian

Resources:

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

So Meta

Bootstrapped Web — Wed, 09 Feb 2022 03:49:33 +0000

Brian and Jordan are having a great time as they ride good days, give great updates, and look forward to some exciting things in the near and far future.

In today’s unscripted and random episode, Brian and Jordan give us some great news in terms of business updates. They also talk about one of the bigger customer issues when it comes to running a SaaS company. Not to mention, a deep dive into the metaverse: what does the future look like with Web3?

“What shoe will need to drop in order for Web3 solutions or applications or products or services or platforms to spill over into the wider market?” – Brian Casel

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Here are today’s conversation points:

That wonderful feeling when things are starting, building, and rolling
How to keep the momentum going
SaaS issues: the discomfort of having most of your market be anonymous to you
Foreshadowing of why we should take the metaverse seriously
- Will Web3 be corporate-owned or user-owned?
- Monetization through advertising and other types of models
TinyConf, Disney, and other events in the near future

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

“No one is going to get to zero. But you do need to remain underneath the line of ‘too frustrating.’ And that line has not been determined yet.” – Jordan Gal

Resources:

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

Wheels Are Turning

Bootstrapped Web — Tue, 18 Jan 2022 19:26:43 +0000

Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, they also give updates on Rally’s marking and sales funnels, and prioritization at ZipMessage.

Today’s episode is filled with business updates, optimism, and great outlooks for 2022. Don’t forget to check out ZipMessage on ProductHunt!

“I prioritize [the reliability of recording and playback] over shipping a brand new feature.” – Brian

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Here are today’s conversation points:

The sale of ProcessKit
Chicago, look out for Jordan
ZipMessage on Product Hunt
Is Rally ready to go to market?
- Marketing funnels and sales funnels
Prioritization at ZipMessage
ZIpMessage conversion emails

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

“What helps me is knowing what the journey looks like.” – Jordan

Resources:

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

2021/2022 New Year reflections

Bootstrapped Web — Tue, 18 Jan 2022 19:19:40 +0000

Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th

The Chaos

Bootstrapped Web — Mon, 10 Jan 2022 17:37:17 +0000

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

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

Define Traction

Bootstrapped Web — Mon, 10 Jan 2022 16:38:37 +0000

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

Resources:

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

Chicken or Egg Development

Bootstrapped Web — Wed, 08 Dec 2021 18:40:35 +0000

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

Resources:

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

Go to Market vs. Marketing

Bootstrapped Web — Tue, 09 Nov 2021 22:02:40 +0000

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

Resources:

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

How to Fund a Startup

Bootstrapped Web — Tue, 09 Nov 2021 21:38:59 +0000

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

Resources:

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

Should We Rename the Podcast?

Bootstrapped Web — Wed, 27 Oct 2021 02:12:55 +0000

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

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

Audience Ops Changes Hands

Bootstrapped Web — Thu, 23 Sep 2021 06:00:00 +0000

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 — Thu, 19 Aug 2021 06:00:00 +0000

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

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

Back and Running

Bootstrapped Web — Thu, 05 Aug 2021 06:00:00 +0000

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

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

Metrics & Hiring Funnels

Bootstrapped Web — Thu, 24 Jun 2021 06:00:00 +0000

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.

“I saw a ZipMessage pop up in my Slack the other day. I love seeing it organically used because that’s the tool that fits.” – Jordan

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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

“People get value from it and they don’t tell you they’re getting value from it. It’s just happening and you don’t see it right in front of you. You have to see the stats.” – Brian

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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

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.

Hiring Media Creators

Bootstrapped Web — Thu, 17 Jun 2021 06:00:00 +0000

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

“You want the authentic version of the media and the audience and value, and then allowing for a bridge from there, over to the product.” – Jordan

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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

“If you want an engaged community where they interact with each other, the audience has to come first.” – Brian

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Mentioned on today’s episode:

Leave us a message here

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

Raising The Bar

Bootstrapped Web — Thu, 03 Jun 2021 06:00:00 +0000

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.

“When you start to talk about a bunch of people, all in coordination, all in different time zones, all on different things, that stuff is just magic to me.” – Jordan

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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

“The way that I think about integrations generally is, it’s more about, ‘Does it solve a customer problem and customer conversion?’” – Brian

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Mentioned on today’s episode:

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

Unthinkable podcast by Jay Acunzo

Our stuff:

Leave us a message here

Rally On

Bootstrapped Web — Thu, 20 May 2021 06:00:00 +0000

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:

Leave us a message here

Rally On

Josh Pigford’s Maybe company compensation model

Sahil Lavingia on Gumroad’s team model

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

Bugs vs. Customers

Bootstrapped Web — Thu, 06 May 2021 06:00:00 +0000

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.

“I’m slowed down by the product and the bug-fixes.” – Brian

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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

“My favorite thing (the thing that I’m good at) is articulating that future vision clearly.” – Jordan

Resources:

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

Staying positive

Bootstrapped Web — Thu, 29 Apr 2021 06:00:00 +0000

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.

Never Fast Enough

Bootstrapped Web — Thu, 15 Apr 2021 06:00:00 +0000

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.

“I did want to step in and reiterate some of my larger goals and priorities to the team on Audience Ops, about what makes Audience Ops great. Kat really did that well, but I want to make sure that the team really knows, ‘This is why things work so well here. Let’s keep this going.’” – Brian

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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

“If you have an audience and you want to start a company, at this point, you can just ask for money. You can legally, publicly ask for money.” – Jordan

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Resources

Maybe.co

Josh Pigford’s Twitter

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

Let’s Be Less Wrong in 2021

Bootstrapped Web — Thu, 24 Dec 2020 06:00:00 +0000

Brian and Jordan are rounding out 2020 by looking back and looking into the future. Brian talks about taking a break for the next couple weeks, ProcessKit updates, and looking back to see what he was wrong about when thinking about 2020. Jordan talks about a couple podcasts he was a part of, fun holiday parties, and minimizing risks of wasting hours. They also go over some final thoughts about the holidays, and what they plan on doing on their vacation.

[tweetthis]“What were all the things that I was wrong about? In the last year?” - Brian [/tweetthis]

Here are today’s conversation points:

Taking a break and the importance of stepping away
- What is burnout?
- Macro versus micro expectations for ourselves
Podcasts that Jordan has been a part of lately (Greylock, Better Done Than Perfect)
Looking back on 2020
What happens in ‘21?
ProcessKit updates: onboarding flow, new home pages, etc.
Holiday parties (and possibly monthly happy hours) using GatherTown
The process for validating products

[tweetthis]“I don’t do that many hours of intense work and writing and that sort of thing, but it is the constant thinking and worrying.” - Jordan [/tweetthis]

Resources:

Greylock (Greymatter): “Mike Duboe | The Rise of Headless Commerce”

Better Done Than Perfect: Radical Onboarding Experiments with Jordan Gal

Better Done Than Perfect: Launch Lessons & Product Surveys with Rand Fishkin

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

All the Things

Bootstrapped Web — Thu, 10 Dec 2020 06:00:00 +0000

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 a surprise nomination, onboarding and conversion, marketing and tracking, and niche podcasting.

[tweetthis]“If you keep hammering on a topic that resonates with people, stuff still sits on the internet and attracts people.” - Brian [/tweetthis]

Here are today’s conversation points:

Making quality content
Friday snapshots, Spotify Wrapped Year in Review
Black Friday and Cyber Monday wrap-up
Shopify checkouts, quirks, and limitations
Nomination for bootstrapper podcasts
ProcessKit onboarding and the core of the product
How to change from conversion to paid?
Marketing
- Marketing and tracking from two different sources
- Paypal, what?!
- Focusing your marketing efforts; niching down
Goals for 2021: consistency
Podcasting in a niche versus having a wide audience

[tweetthis]“When you’re selling in an app store but you have your own website, there is a big disconnect on tracking.” - Jordan [/tweetthis]

Resources:

Microconf: SaaS Podcast Awards

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

Satisfying Customers

Bootstrapped Web — Thu, 12 Nov 2020 06:00:00 +0000

On this episode of Bootstrapped Web (dubbed the “anything but election talk” episode), Jordan and Brian go over Carthook’s exciting launch in the Shopify App Store and ProcessKit’s visual upgrade. Brian also has a couple of aces up his sleeve when it comes to high level changes as well as day-to-day uses for ProcessKit. Today the focus is all about what it means to satisfy customers: new and existing customers. How do you convert trial customers? How fast should you handle feature requests? How do you deal with the pressures put onto you by customers? How to show your constant level of progress but how do you filter customer feedback/expectations?

[tweetthis]“Anytime you’re talking about visual user updates, especially if it affects the entire app (which this did) you get nervous. People don’t like change, even if it’s better change.” - Brian [/tweetthis]

Here are today’s conversation points:

The Carthook logo is in the Shopify App Store!
- Team morale
- Departments that need Jordan’s focus
- Updates, expectations, and reviews
The limitations of being both the designer and founder of a product
ProcessKit upgrades:
- To dashboard or not to dashboard?
- Email templates with liquid tags to increase the dynamic changes for these templates
The pressure of “What’s next?” and prioritization
The current competitive climate in SaaS
- Pipe
- MainStreet
- Visualize Value

[tweetthis]“I think we’ve spoken before about how I look at the company as like, ‘Where is the fire burning...the hottest?’ At any point in time it’s not like everything’s on fire or everything requires attention. There’s usually one part of your company where there’s more going on.” - Jordan [/tweetthis]

Resources:

Jason Lemkin’s post about Dashboards

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

Calm Before the Storm

Bootstrapped Web — Thu, 05 Nov 2020 06:00:00 +0000

Jordan and Brian are back after a few weeks. It is election week; that means a lot of stress and a lot of chaos. But before that stuff hits the fan, Jordan is launching a new Carthook product inside the Shopify app store and Brian has been redesigning the ProcessKit app to fix little frustrations. They’re also talking about structure, spreadsheets, and the importance of app store reviews

[tweetthis]“As we started to add more and more features, the overall structure and experience (and I’m talking about very detailed things) hasn’t kept up and so I wanted to solve for all of these little frustrations in the app that have accumulated.” - Brian [/tweetthis]

Here are today’s conversation points:

New Carthook products inside the Shopify App Store
- Preparations and anticipating the launch
- Spreadsheets and scenarios
- The Prisoner’s Dilemma
- Dynamic pricing and price points
ProcessKit App redesign
- Progress in SaaS products
- Community-based promotions
- Marketing and funneling
Being able to separate yourself from your business
The importance of customer experience and app store reviews
Jordan’s new obsession: Cohere

[tweetthis]“It is a prisoner’s dilemma. You’re stuck, you don’t have all the information. What you do has a big impact on them, what they do has a big impact on you. But you’re not colluding.” - Jordan [/tweetthis]

Resources:

How to Price Your SaaS Product by Patrick Campbell

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

Good morning

Bootstrapped Web — Thu, 15 Oct 2020 06:00:00 +0000

Today Brian and Jordan are talking about deadlines, Black Friday, and a little bit of introspection. They go over their love/hate relationship with mornings. They also take a deep dive into hopes, dreams, dedication, and hiring true believers.

[tweetthis]“I still really believe in dedicating time to writing tests and for us that really means integration tests and feature tests.” - Brian [/tweetthis]

Here are today’s conversation points:

The Carthook deadline
How the new ProcessKit developer stepped up
Testing features, web integration expectations
Different ways of coping with stress
The importance of mornings:
- Brian’s morning routine
- Jordan’s morning routine
- Can you change whether or not you can be a morning person?
Hopes, dreams, and dedication
- “What is the worst case scenario here?”
When it is okay to forgo delegating and doing things yourself?
- Freelancing versus Full-Time Employee
- Marketing projects
- Hiring a true believer

[tweetthis]“When you make a decision, go harder at it.” - Jordan [/tweetthis]

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

Talkin shop with Ian Landsman

Bootstrapped Web — Thu, 08 Oct 2020 05:10:00 +0000

On today’s episode of Bootstrapped Web, Brian and Jordan are joined by Ian Landsman from HelpSpot. Ian has made product after product over the years, from UserScape to HelpSpot to LaravelJobs and Thermostatio. You can find him on Twitter or you can learn more about him on his website.

Brian, Jordan, and Ian are talking all about podcasts, business models, and privacy on the internet. They also go over the lessons they’ve all learned from previous products and projects they have been involved in.

[tweetthis]“How many years, how many decades, can you keep pushing project management software when that space just gets so big and so competitive?” - Brian [/tweetthis]

Here are today’s conversation points:

Ian’s potential new podcast: structure or no structure?
Hey, Clubhouse, and other email services
The hidden cost of privacy and complacency in a product
Previous products, projects, and the lessons learned
How involved Ian, after being 15 years into HelpSpot
What does feature development look like for Ian?
Optimizing websites as supplementary platforms
Business models: per user, paying per clients
Are demos worth it?
Affiliate programs and consulting hang ups for ProcessKit
- Third party hosting and consulting companies
Real-time brainstorming about onboarding consultants

[tweetthis]“Clubhouse jumped the shark from being exclusive to just being ‘annoyed that you couldn’t get in and now you’re resentful.’ And then, of course, I got an invite and a DM a minute later. [laughs]” - Jordan [/tweetthis]

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

Company Design

Bootstrapped Web — Thu, 01 Oct 2020 05:34:00 +0000

We’re in a great mood on today here atf Bootstrapped Web. We’re talking about drive-in movies, apple picking, AirBnB’s, Twitter, and business updates. This episode is a bit of a topic potpourri is as we cover new features, hiring and interview processes, big picture visions, and building communities.

[tweetthis]“Aside from the obvious goal of marketing (which is to grow traffic and leads and sales), I think the bigger goal should be to build community.” - Brian [/tweetthis]

Here are today’s conversation points:

ProcessKit fields and features
- Web developer updates
Carthook’s newest app for Shopify
- Their new full-time, in-house product designer
Switching ProcessKit marketing site to a static site to Wordpress
- Static vs Dynamic
The hiring and interviewing process
- The importance of culture fit and temperament
Looking at the big picture and company design
- “What kind of company do I want to build?”
Building an ideal community, and longevity
- Building relationships
Snap Friday and current hobbies

[tweetthis]“Our culture fit is a nice, optimistic, happy person. And that might sound really thin but it really matters. If you’re naturally optimistic and curious, it leads to happiness, even in times of stress.” - Jordan [/tweetthis]

Resources:

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

Should You Audience?

Bootstrapped Web — Thu, 17 Sep 2020 05:00:00 +0000

Brian and Jordan are back behind the (brand new) mics. They’re reminiscing about the beginning of the podcast, the fires in the west coast, and catching up on the latest news in the industry as well as their businesses.

[tweetthis]“From a design standpoint, in the first year of an app, so many things change, like, in terms of the feature set and the scope.” - Brian [/tweetthis]

Here are today’s conversation points:

The tail end of the hiring process
- Using the Silo strategy
5 years in the business of podcasting and with our products
Personnel shake-up in ProcessKit
Finance topic: the launch of Long Term Stock Exchange
Making progress in different stages of products
New feature: Dynamic roles
Competition
Audiences Building
- Getting enjoyment from personal and professional endeavors...or not
- “You are not a product.”
- The Billion Dollar Blog
- How important is audience building?

[tweetthis]“So much is determined by that initial burst of energy and that initial first year or two that sets you up on this trajectory.” - Jordan [/tweetthis]

Resources:

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

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

ZipMessage has a new name...

Putting in the hours

All the Things

Projections… What Are They Good For?

Communicating What's Next

Product in Market (Is How We Learn)

Building in public… More.

Another Year

Talking Points:

Resources:

Hey ChatGPT, what should we talk about?

Here are today’s conversation points:

Resources:

Twitter Takes (and Some Business Talk)

Here are today’s conversation points:

Resources:

Q4 Energy

Here are today’s conversation points:

Resources:

Tools & People

What We'd Build (If Not This)

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

Research, Roadmaps, People, and Product

Company as a Product

Product vs. Pipeline

Talking to Customers

Marketing in 2022￼

Traction... Then what?￼

Everything Must Go

CartHook Acquired!

Tokenizing

So Meta

Wheels Are Turning

2021/2022 New Year reflections

The Chaos

Define Traction

Chicken or Egg Development

Go to Market vs. Marketing

How to Fund a Startup

Should We Rename the Podcast?

Audience Ops Changes Hands

Marketing ideas

Back and Running

Metrics & Hiring Funnels

Hiring Media Creators

Raising The Bar

Rally On

Bugs vs. Customers

Staying positive

Never Fast Enough

Let’s Be Less Wrong in 2021

All the Things

Vote for us on the SaaS Podcast Awards!

Satisfying Customers

Calm Before the Storm

Good morning

Talkin shop with Ian Landsman

Company Design

Should You Audience?

Marketing in 2022

Traction... Then what?