Bootstrapped Web
99 episodes - English - Latest episode: over 1 year ago - ★★★★★ - 55 ratingsBrian 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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Episodes
Tools & People
September 29, 2022 10:00 - 47 minutes - 43.9 MBWhat 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 … Continue reading Tools & People
What We’d Build (If Not This)
September 22, 2022 09:58 - 56 minutes - 52 MBBrian 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 … Continue reading What We’d Build (If Not This)
Work-Life (Hour-by-Hour), Explained
September 08, 2022 06:18 - 44 minutes - 41.1 MBWhat 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 … Continue reading Work-Life (Hour-by-Hour), Explained
Research, Roadmaps, People, and Product
September 01, 2022 08:20 - 49 minutes - 45.8 MBHow 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 … Continue reading Research, Roadmaps, People, and Product
Company as a Product
August 11, 2022 09:36 - 37 minutes - 34.4 MBHow 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 … Continue reading Company as a Product
Product vs. Pipeline
July 14, 2022 09:39 - 43 minutes - 40.5 MBWhat 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 … Continue reading Product vs. Pipeline
Talking to Customers
June 09, 2022 10:00 - 43 minutes - 40.4 MBHow 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 … Continue reading Talking to Customers
Marketing in 2022
April 28, 2022 10:15 - 42 minutes - 39.2 MBBrian 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 … Continue reading Marketing in 2022
CartHook Acquired!
April 07, 2022 10:00 - 51 minutes - 48.4 MBWhat 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 … Continue reading CartHook Acquired!
Traction… Then what?
March 17, 2022 10:00 - 38 minutes - 35.7 MBHow 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 … Continue reading Traction… Then what?
Everything Must Go
February 24, 2022 11:00 - 38 minutes - 35.5 MBWe 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, … Continue reading Everything Must Go
Tokenizing
February 10, 2022 11:00 - 37 minutes - 34.8 MBHow 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 … Continue reading Tokenizing
So Meta
January 27, 2022 11:00 - 34 minutes - 32.1 MBBrian 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 … Continue reading So Meta
Wheels Are Turning
January 20, 2022 11:00 - 40 minutes - 37.9 MBBrian 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 … Continue reading Wheels Are Turning
2021/2022 New Year reflections
January 11, 2022 07:30 - 38 minutes - 58.3 MBBrian’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 … Continue reading 2021/2022 New Year reflections
ZipMessage on Product Hunt Today + Year-end reflections
January 11, 2022 07:30 - 38 minutes - 58.3 MBBrian’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 … Continue reading ZipMessage on Product Hunt Today + Year-end reflections
Define Traction
December 16, 2021 11:00 - 35 minutes - 33.3 MBWhat 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 … Continue reading Define Traction
The Chaos
December 09, 2021 11:00 - 42 minutes - 39.8 MBDoes 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 … Continue reading The Chaos
Chicken or Egg Development
November 11, 2021 11:00 - 30 minutes - 28.8 MBWhen 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 … Continue reading Chicken or Egg Development
How to Fund a Startup
October 28, 2021 10:00 - 48 minutes - 45.1 MBJordan 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 … Continue reading How to Fund a Startup
Go to Market vs. Marketing
October 14, 2021 10:00 - 38 minutes - 35.6 MBWhat 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 … Continue reading Go to Market vs. Marketing
Should We Rename the Podcast?
September 30, 2021 10:00 - 41 minutes - 38.8 MBBootstrapped 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 … Continue reading Should We Rename the Podcast?
Audience Ops Changes Hands
September 23, 2021 10:00 - 56 minutes - 52.6 MBSome 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 … Continue reading Audience Ops Changes Hands
Marketing ideas
August 19, 2021 10:00 - 38 minutes - 35.3 MBIntroduction: 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, … Continue reading Marketing ideas
Back and Running
August 05, 2021 10:00 - 38 minutes - 36.1 MBAfter 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, … Continue reading Back and Running
Metrics & Hiring Funnels
June 24, 2021 10:00 - 44 minutes - 41.5 MBBrian 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 … Continue reading Metrics & Hiring Funnels
Hiring Media Creators
June 17, 2021 10:00 - 33 minutes - 31.6 MBBrian 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 … Continue reading Hiring Media Creators
Raising The Bar
June 03, 2021 10:00 - 39 minutes - 37 MBBrian 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 … Continue reading Raising The Bar
Rally On
May 20, 2021 10:00 - 58 minutes - 54.5 MBIt’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 … Continue reading Rally On
Bugs vs. Customers
May 06, 2021 10:00 - 34 minutes - 32.4 MBBrian 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 … Continue reading Bugs vs. Customers
Staying positive
April 29, 2021 10:00 - 46 minutes - 43.4 MBBrian 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 … Continue reading Staying positive
Never Fast Enough
April 15, 2021 10:00 - 42 minutes - 39.3 MBBrian 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, … Continue reading Never Fast Enough
Know Thyself
April 01, 2021 10:00 - 42 minutes - 40.2 MBWill this be the week that Jordan finally gets to talk about crypto? In this episode of Bootstrapped Web, Brian and Jordan give us some updates on their businesses. Is Brian running late with ZipMessage? What has been going on behind the scenes of Jordan’s secret project? They also talk indepth about discipline and productivity. … Continue reading Know Thyself
How is it different?
March 25, 2021 10:00 - 49 minutes - 47.1 MBThis is two weeks in a row for Brian and Jordan. In today’s episode they’re talking about new toys and tools, Twitter drama, and business talk, specifically Jordan’s newest team member and Brian’s newest product. April 5th is going to be a big week for both Brian and Jordan when it comes to business news. … Continue reading How is it different?
Bootstrapped to VC
March 18, 2021 10:00 - 47 minutes - 44.6 MBOfficially a year after the pandemic started, Brian and Jordan do a bit of reminiscing and chatting about vaccine news before diving into updates about work. Not to mention, Jordan gets his first real haircut of the year. On the business front, things are moving (slow and steady) for Brian. ProcessKit has accumulated a decent … Continue reading Bootstrapped to VC
Launching from no man’s land
March 04, 2021 11:00 - 42 minutes - 40 MBToday, Brian and Jordan are talking about what it’s like in no man’s land and their struggles with imposter’s syndrome. Brian shares more details about his newest venture. Jordan talks about his need for structure. They do a deep dive into the launch process and various launch strategies as well as updates on their various … Continue reading Launching from no man’s land
Who is the customer for this SaaS?
February 18, 2021 11:00 - 53 minutes - 50.1 MBBrian and Jordan are back after a short break. Today’s topics involve new developments with Brian, Twitter conversations, and market research for new and current projects. Brian gives us a sneak peak into a new project. Jordan brings his opinions on Twitter and how companies are using their social media profiles for marketing. They briefly … Continue reading Who is the customer for this SaaS?
New year, new directions
January 28, 2021 11:00 - 43 minutes - 40.9 MBBrian and Jordan are back after a bit of a hiatus. Today they’re trying a different format change as each takes center stage for half of the show so they can better update everyone on their progress since the new year started. And what a new year it’s been so far: finishing off some old … Continue reading New year, new directions
Let’s Be Less Wrong in 2021
December 24, 2020 11:00 - 35 minutes - 34 MBBrian 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 … Continue reading Let’s Be Less Wrong in 2021
All the Things
December 10, 2020 11:00 - 48 minutes - 46.2 MBVote 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 All the Things
Satisfying Customers
November 12, 2020 11:00 - 36 minutes - 34.9 MBOn 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 … Continue reading Satisfying Customers
Calm Before the Storm
November 05, 2020 11:00 - 48 minutes - 45.5 MBJordan 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. … Continue reading Calm Before the Storm
Good morning
October 15, 2020 10:00 - 51 minutes - 48.6 MBToday 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. Here are today’s conversation points: The Carthook deadline How the new ProcessKit developer stepped up Testing features, … Continue reading Good morning
Talkin shop with Ian Landsman
October 08, 2020 09:10 - 1 hour - 62.3 MBOn 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 … Continue reading Talkin shop with Ian Landsman
Company Design
October 01, 2020 09:34 - 48 minutes - 46.2 MBWe’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. Here are today’s conversation points: ProcessKit fields … Continue reading Company Design
Should You Audience?
September 17, 2020 09:00 - 52 minutes - 49.7 MBBrian 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. Here are today’s conversation points: The tail end of the hiring process Using the Silo strategy … Continue reading Should You Audience?
The Next Chapter in the Product
September 10, 2020 10:00 - 45 minutes - 43.6 MBIt’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 The Next Chapter in the Product
Chicken or Egg or Fundraise
August 20, 2020 09:00 - 41 minutes - 39.5 MBWe’re back with “Boo-strapped Web”. We’re behind the mic talking about stress, marketing, executing decisions, and guilt over new hire experiences. Lastly, we’re going over the latest news in startup financing, which could blow everything out of the water: rolling funds. Here are today’s conversation points: New Hire Experiences New employee Slack introductions PoweredBySearch’s great … Continue reading Chicken or Egg or Fundraise
Hello Competitors
August 06, 2020 10:00 - 38 minutes - 36.3 MBToday we’re talking about camping ratios, COVID and Black Friday, the eCommerce boom due to COVID, emotions versus moods, Twitter, and competitors. We go over some bold and unique marketing strategies with ProcessKit, how we’ve won Jordan over in the “Working-from-home” battle, and about hiring contractors and coaches. Here are today’s conversation points: COVID trends … Continue reading Hello Competitors
What does VC really mean? And marketing.
July 23, 2020 10:00 - 51 minutes - 48.4 MBWe’re back after a two-week break. More specifically, a camping and Niagra Falls break. Today we go over two kinds of VC: vacations and venture capital. Not to mention, we go over ProcessKit’s newest marketing news, Ali Mese’s article on Medium, and our thoughts on positioning. Here are today’s conversation points: How do you know … Continue reading What does VC really mean? And marketing.