Bootstrapped Web

Bootstrapped Web

bootstrappedweb.com
For entrepreneurs who are bootstrapping startups and building a business online


Marketing Loose Ends & Funding Gaps
Nov 28 • 41 min
Jordan and Brian are back behind the mic before Thanksgiving. Jordan talks about how great it feels to be unnecessary (at work) and various B-to-B and B-to-C marketing techniques. Brian talks about kits, his “new trialers”, and Processkit updates. They…
Post-Launch & Code Freezes
Nov 7 • 31 min
Today we’re live and in a rush since Jordan has to take his kids to lunch on their off-day! We talk about post-Halloween shenanigans, Brian’s 37th birthday (at least, he’s not 40), the stats and news from Process Kit’s launch, capturing the creative…
Product Brain vs Marketing Brain
Oct 31 • 41 min
Brian and (a sick) Jordan are back talking about upcoming Halloween festivities, what they missed out on by missing MicroConf (in Croatia), their thoughts on SEO, product vs. marketing, new podcasting ideas, and the new ProcessKit website. “The…
So Much for That Plan
Oct 17 • 48 min
Jordan and Brian are back with updates (even if they’re not so great). Brain updates us on the developments (or lack thereof) with his developer and how communication issues have played a part in the lack of progress. He also talks about how to move…
Continuous Adjustments
Oct 3 • 40 min
Jordan and Brian are back in the studio. Today the main focus is on the continuous adjustments needed in the software industry. They also quickly cover the trend of SaaS companies doing conferences and community-based marketing. Jordan talks about how…
Never Enough MRR
Sep 19 • 47 min
Jordan and Brian are back to a regular podcasting schedule. Brian spent the weekend at a retreat/mastermind group at Martha’s Vineyard. Meanwhile, Jordan was at the Striped Conference. After a quick update, Jordan and Brian talk about the latest episode…
Rabbit Holes Within Rabbit Holes
Sep 12 • 45 min
It’s September, which means we’re talking about the changing of the seasons: kids are back in school, we’re gearing up for Black Friday, updating websites, and checking our numbers. Brian talks about his email marketing, hiring developers, and changing…
Move It up and Accelerate the Plan
Aug 22 • 45 min
Jordan is back! We talk about what we’ve been up to: family trips to Cape Cod, productivity and the stress before vacations, Michigan in the summer, and buying houses, Brian’s assistant. After catching up, we jump right into updates, price changes,…
What Is a “Launch”, Really? w/ Ben Orenstein
Aug 15 • 38 min
With Jordan out of the studio, today our guest is Ben Orenstein. He is the host of the Art of Product podcast as well as Co-founder of the online tool, Tuple, which was built for remote pair programming on Macs (screenshare with audio). We talk about what…
Starvation or Indigestion?
Jul 25 • 44 min
Two weeks in a row, and still plenty of topics and updates to discuss! Jordan wants to talk about how startups fail when they take on more opportunities than they can handle. If he decides to pursue any of the big opportunities that popped up recently,…
Navigating First Customers / Making a Big Price Change
Jul 18 • 57 min
We are back from a lengthy hiatus and we have plenty to discuss for today’s episode! Brian updates our listeners about ProcessKit and what he is learning from the process. Jordan wants to discuss the price increases coming to Carthook. He also dives into…
Inviting First Customers / App Stores
Jun 6 • 46 min
Hey, we’re back and we’ve got some lessons and updates to share with you! Both of us have plans to travel over the next few weeks. Jordan will be visiting his Slovenia team and Brian will be attending WP Elevation. Carthook and ProcessKit are both at a…
Inviting First Users & Profitable Team Growth
May 9 • 42 min
We ask ourselves a lot of questions during this episode. Jordan is looking at Carthook and seeing exciting changes but now he has to consider what comes next. Brian is still getting ProcessKit ready for users and has to ask himself who should the first…
The “Strings” Attached to VC
May 2 • 41 min
We have had some major decisions to make lately. Brian is working on ProcessKit and his self-imposed deadline is just around the corner. Now, he has to decide if he wants to launch a semi-ready product to his users. We discuss when is the appropriate time…
Selling to Teams & Hiring an Assistant
Apr 11 • 53 min
Hey! We are back from MicroConf and we’ve got some great takeaways from the experience. We discuss the speakers and the talks and how the experience changes for us year to year. We also have some updates for you. Brian is still working on ProcessKit and…
When Customer Support Does & Doesn’t Pay
Mar 28 • 39 min
MicroConf is coming and we’re psyched! We take a glimpse at the schedule for this year’s event and we talk about what we’re looking forward too. Brian has an update on his pricing issue with ProcessKit and the conclusion he came too. Jordan is happy to…
Pricing Per User or…?
Mar 21 • 57 min
MicroConf is just around the corner and we are ready for it! We share our excitement about the conference and encourage you the listeners to say hi if you plan to attend this year. Brian has an update about ProcessKit and he actually has a launch date! He…
Hiring (or not?)
Mar 7 • 42 min
We cover a subject that affects all bootstrappers today. Should you hire or not? This topic comes up because we both are looking to hire some new team members. Jordan has seven job openings and Brian is looking for a new writer for Audience Ops. We…
Who Is Selling the Product?
Feb 21 • 47 min
MicroConf is right around the corner! We are excited and really looking forward to this year’s event. Brian is jumping back into ProcessKit but he’s struggling to get back into the groove. We discuss why that happens and how we try to keep momentum during…
Sales to Onboarding Process / Profitable Side Projects
Feb 14 • 38 min
This week, Jordan has been very focused on sales. He and his company are considering hiring their first salespeople. Jordan shares he believes that they’ve gotten complacent and are starting to look at things in the wrong way – in aggregate instead of in…
Churn and Onboarding. Onboarding and Churn.
Feb 7 • 56 min
Today we talk about something that affects all businesses, churn. No matter how successful your business is, everyone deals with customer churn. Jordan has decided to tackle Carthook’s churn problem head-on. He shares with Brian how he and his team have…
Speaking Our Minds in 2019 / How Not to Increase Prices
Jan 17 • 50 min
Welcome to 2019! This is our first episode of the year and we have a lot to say! Brian is planning a lot of travel these few months. That means that some of his projects are on the back burner. He gives an update on both ProcessKit and Sunrise KPI and…
More Questions Than Answers in 2019
Dec 27, 2018 • 47 min
We are shying away from discussing goals or resolutions for the businesses this year. Instead, we reflect on how the bootstrapped world and business models have changed. A lot of approaches and marketing techniques have gone by the wayside in the last two…
Team Equity / A New App / The Next App
Dec 20, 2018 • 38 min
The holidays are here! The office parties are going on and Christmas music is everywhere! Today Jordan is celebrating the growth of Carthook by offering his employees stock options. He discusses the stickiness of the decision and the excitement and…
Surviving & Thriving Through Black Friday / Building an App in a Week
Dec 6, 2018 • 39 min
With the year winding down we are feeling reflective during this episode of Bootstrapped Web. Jordan compares the state of Carthook from last year versus this year. A lot can change in a year! Brian is in a transition period right now and is currently…