25 episodes

Bootstrapped Web is for entrepreneurs bootstrapping their startups, who believe that the best way to get to where we're going is to learn by doing. Conversations, case studies, and interviews with entrepreneurs who are building profitable businesses online. Let's do this.

Bootstrapped Web Bootstrapped Web

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Bootstrapped Web is for entrepreneurs bootstrapping their startups, who believe that the best way to get to where we're going is to learn by doing. Conversations, case studies, and interviews with entrepreneurs who are building profitable businesses online. Let's do this.

    Culture & Onboarding

    Culture & Onboarding

    Brian and Jordan are back for the third week in a row. We talk about their plans for the next couple of weeks (Slovania and BigSnowTinyConf). We also go through a few current and upcoming updates. We pose a few questions including, when you have a new product, do you take longer and make base features, or differentiate first? How do you feel about working remotely or working in a coworking space with other people? Do you hire an individual freelancer or go to an agency?


    “These things come up constantly and the challenge as an entrepreneur is just dealing with it and getting used to dealing with it and just saying, ‘Oh, just another hurdle, whatever. I’ll just go through this one also.” – Jordan Powered By the Tweet This PluginTweet This







    Here are today’s conversation points:



    Dealing with hurdles as an entrepreneurThe great things about micro confs and small conferencesJordan’s team shifting and upcoming changesBrian’s timing with shutting off self-sign-upBrian’s new demosBrian’s new developer and small updates Jordan’s weekly demos: where are your shortfalls?Remote versus office workThe resiliency of hard workers and keeping a balance at workJordan’s buckets for Carthook






    “Just to have (a developer) in my back pocket for when I need a little bit of extra help. I feel like an agency can be a little more reliable.” – Brian, on looking at individual freelancers or looking at an agency.Powered By the Tweet This PluginTweet This







    Resources



    BigSnowTinyConf, website



    SunriseKPI



    Audience Ops Case Studies 



    ProcessKit 



    Carthook  



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

    • 59 min
    Positioning and Profitability

    Positioning and Profitability

    We’re back! We’re excited about some winter weather activities and all of our 2020 ideas. We talk about brainstorming, questions, nomenclature, tiny conferences, and profitability.






    “There’s always an optimal path and you’re never on it.” – JordanPowered By the Tweet This PluginTweet This







    Here are today’s conversation points:



    Looking back one last time on 2019Jordan is shifting from a direct-response mindset to a brand awareness mindsetBrian’s contemplative train ride and mini-retreatThe importance of tags, naming, and positioningJordan’s visual representation of profitabilityBringing in new team membersBrian poses some great questions for Big Snow Tiny Conf 2020, in Vermont


    “ProcessKit is for documenting your processes and powering your pipelines.” – BrianPowered By the Tweet This PluginTweet This







    Resources



    From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue by Aaron Ross, Amazon



    SunriseKPI



    Audience Ops Case Studies 



    ProcessKit 



    Carthook  



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

    • 53 min
    Back At It

    Back At It

    Today we’re talking about getting back to work after the holiday “festivities”, the inability to unplug, slowing down in December, the themes that ran through 2019, and what our themes for 2020 will be.






    “It’s just easy to be in this good, positive, optimistic mood when things are growing and 2019 wasn’t like that.” – Jordan Powered By the Tweet This PluginTweet This







    Here are today’s conversation points:



    What to do when you can’t unplug your brainSlumps around the holidays2019 was a rebuilding year for Jordan and 2020 seems to have a theme of marketingBrian was marinating in anticipation for 2020How Jordan was able to noodle while he and his team were on a breakWhere Brian is going to put his focus in 2020Jordan’s newest product lead, JessicaWhat Brian is going to ponder over during his one-man retreat






    “This early in a product lifecycle of a product, the marketing is the product.” – BrianPowered By the Tweet This PluginTweet This







    Resources



    SunriseKPI 



    Audience Ops Case Studies 



    ProcessKit  



    Carthook  



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

    • 57 min
    Marketing Plans for 2020

    Marketing Plans for 2020

    Brian and Jordan are back! We talk about holiday plans, the work-from-home life and coworking spaces, seeing and working with other human beings, spending all of our money at Starbucks, and the latest in marketing techniques. We talk about our past marketing mistakes and what went well, as well as what we plan on doing in the future.






    “As owners, we feel very powered. When we feel pain, we just want to solve it. We want it to stop. We don’t want to feel pain anymore.” – Jordan Powered By the Tweet This PluginTweet This







    Here are today’s conversation points:



    Sunrise and Audience Ops statsBrian’s Explainer Video SeriesCase studies content: testimonials, and interviewsAudience Ops team changes/shiftingWhat to do to help a team member complete a transition from one job to anotherBlack Friday stats for CarthookProcess Kit statsCarthook marketingSEO and content focus for 2020Process Templates for Process Kit






    “Sometimes it’s like you’re roaming around in a fog, trying to figure out which direction you should be going.” – Brian (on trying to find the right price points and marketing tactics)Powered By the Tweet This PluginTweet This







    Resources



    SunriseKPI 



    Audience Ops Case Studies 



    Making an Explainer Video Series 



    ProcessKit  



    Carthook  



    Out of Beta podcast  



    Rework Podcast with DHH and Dave Teare  



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

    • 50 min
    Marketing Loose Ends & Funding Gaps

    Marketing Loose Ends & Funding Gaps

    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 also talk about one of DHH’s Tweet-rants and what they’re grateful for.






    “For things like this, one off-the-shelf software doesn’t solve the whole problem, you always need some element of custom implementation.” – Brian Powered By the Tweet This PluginTweet This







    Here are today’s conversation points:



    ProcessKit’s kits (process templates)Marketing techniquesBrian’s “new trial” experiencesBrian’s to-do listDHH’s rant on profit and fundingBrian’s metrics dashboardMore work with SunriseKPI






    “What I have seen is that the best ones don’t market their product; they market the result.” – JordanPowered By the Tweet This PluginTweet This







    Resources Mentioned:



    ProcessKit



    Carthook



    DHH’s Tweet



    Sunrise KPI



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

    • 41 min
    Post-Launch & Code Freezes

    Post-Launch & Code Freezes

    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 process, and Jordan’s code freeze. 



    We also talk about how to capture the creative process at its peak and how we can analyze that data to gain information for the future.


    “I’m becoming more and more convinced that is the content people want. That authentic content from the company itself.” – Jordan Powered By the Tweet This PluginTweet This







    Here are today’s conversation points:



    ProcessKit LaunchThe difference in feedback from post-launch and early-adoptersLastPass vs. 1PasswordNew ProcessKit websiteCapturing the creative processThe switch from open trials to application demosBrian’s webinar and his to-do listWhen to listen to resistanceCode freezes


    “Real authentic–especially story-based–marketing is really really useful.” – Brian Powered By the Tweet This PluginTweet This







    Resources Mentioned:



    ProductHunt



    LastPass



    1Password



    New ProcessKit website



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

    • 31 min

Customer Reviews

Allnicknamesaretaken1234(?;:( ,

Varied and informative

Great range of topics that help give founders inspiration for new strategies.

Twisted Angle Knits ,

Personal Development and a Fantastic Case Study...

I listen to a lot of podcasts for business this one is my favourite. I went back to the beginning and started from episode 1. The development of Brian and Jordan is a fantastic case study in itself, and I can't help but cross my fingers for your guys everytime you launch something or try something new.

So many action steps and great tips to do in your own business, without the fluff all the others podcasts add in. Love the way you guys ask the direct, no nonsense questions and get down to the core info.

Keep up the great work guys.

Peter Roy Barlow ,

A massive wealth of practical knowledge

Too often start-up founders sit alone trying to get their boot-strap their businesses off the ground without having an insight into how other founders are solving the (sometimes universal) problems startups face. This podcast is an antidote to that isolation! Using their real-world experiences, Jordan and Brian walk you how they tackle the key challenges which start-ups face. I listen to many podcasts and this is by far the most valuable for me.

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