Bootstrapped Web

Bootstrapped Web

bootstrappedweb.com
For entrepreneurs who are bootstrapping startups and building a business online
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…
Launching a New Product in a Month / VIP Customer Sales
Nov 22, 2018 • 49 min
We are gearing up for the holiday season here at Bootstrapped Web. Jordan has a serious talk about self-care and knowing when to step back. Brian gives an update on ProcessKit and announces a new product. Automation Guides is launching later this month.…
Ben Orenstein Joins us to Talk Bootstrapping
Nov 8, 2018 • 52 min
Ben Orenstein, is the co-host of The Art of Product podcast, a show where Brian recently appeared. Ben also tells us about his most recent project, Tuple, a tool for remote pair programming. We discuss where the idea for Tuple came from and the team who…
Building in Public / Case Study Marketing / TinySeed
Nov 1, 2018 • 45 min
We have some exciting updates to share and we give our reaction to Rob Walling and Einar Vollset’s big announcement of the TinySeed Fund. Jordan and his team are preparing to move offices in Slovenia. He also sings the praises of case studies. Carthook…
Bootstrapping Reality / Technical cofounders / New Management
Oct 11, 2018 • 53 min
Today’s episode is a straightforward update episode for us. Brian is moving forward with ProcessKit and reflects on his goals for the project. Jordan celebrates the awesome team he has built over at Carthook and shares what it is like to step back and see…
ProcessKit Early Access / Celebrating Growth / CTO Questions
Sep 13, 2018 • 57 min
We are back to tell you about some exciting news and developments. Jordan is enjoying a high mark in Carthook’s business and he found a building so he can move his Portland team. He also discusses the marketing strategies and changes that are making…
Learning Rails vs. Laravel / Branding / Education Marketing
Jul 12, 2018 • 40 min
Summer is in full swing and we are back from our individual vacations. We discuss our businesses and our personal roadmaps for Carthook and Audience Ops. We vent about developing frustrations and we do an armchair quarterbacking session for ConvertKit’s…
Winning Time Back / (Not) Moving Offices / Learning to Code
Jun 7, 2018 • 52 min
It is summertime! We have some great travel plans in the works, but before we pack our bags we want to celebrate the small victories we have seen in our businesses. Audience Ops podcasting is really starting to take off. Brian rehashes the road he took to…
Conference Hopping / Hiring Mistakes / Busting Growth Plateaus
May 24, 2018 • 41 min
It has been three weeks of constant travel for us. We have been jetting around to tons of industry conferences. It has been a hectic and educational time for both of us. We share some of our takeaways from the conferences and really debate the value of a…
Value of a Coach / Hiring Spree / Launching in Public
Apr 26, 2018 • 51 min
On today’s episode, we discuss the real value of a business coach. Jordan has announced that he would like to try his hand at it and Brian shares his own experience with it. We compare the pros and cons of being a coach for other founders and we explore…
What If We Ran Your Business (For the Fun of It)?
Apr 19, 2018 • 48 min
Things are getting back to normal in our respective business worlds. Brian has launched his podcasting service and Jordan is back to business as usual after a visit from Ben and Rok. Today we kick off our “armchair quarterbacking” sessions, and we are…
The Carthook Team Talks Product Development Process
Apr 12, 2018 • 53 min
We welcome Team Carthook to the podcast today! Jordan has brought two of his senior team members to discuss the evolution and future evolution of Carthook’s service. Ben Fisher is the co-founder of Carthook and head of product. Rok Knez is Carthook’s lead…
Launching a Podcasting Service / Learning to Code / Partner Webinars
Apr 5, 2018 • 55 min
MicroConf is right around the corner and Jordan is gearing up for his talk for the event. He bounces some topic ideas off Brian and reveals how his topic choices are reflecting what is happening in Carthook. The version 2 upgrade is finally working…
Charging For Attention / Elusive Product-Market-Fit
Mar 15, 2018 • 28 min
It has been a crazy couple of weeks for both of us. We took a break last week, but we are back and we’ve got some great topics! Jordan spent all of last week fixing a product issue. It was hard, it was frustrating, and it showed him just how great his…
Conference Strategy, Webinar Funnels, & Lead Developers
Mar 1, 2018 • 59 min
We are back to discuss the exciting and frustrating things going on with our businesses. Jordan has a lot on his plate including launching 15-20 new features and a few industry conferences; he will be attending the Traffic and Conversion Summit in San…