[1] The Bootstrapper’s Mindset — How Bootstrappers Learn by Doing

In this first episode — the pilot episode, if you will — I get into what I believe to the core of the bootstrapper’s mentality, and that is that we learn by doing.  I dive into what I think that means and how that’s the central idea behind this new site and podcast.

It’s a shorter episode than what future episodes will be.  I’m still tweaking and tinkering with audio levels and whatnot…

Mentioned in this episode:

  • Pingback: Introducing the Bootstrapped Web Podcast()

  • JervisWhitley

    Love seeing how other bootstrappers roll up their sleeves and get their hands dirty. We do it not only to save money, but to really understand our businesses from the nuts and bolts upward.

    I’d also like to hear more about your use of the Pomodoro (Tomato) techniques. You say that sometimes you let your work creep into 45 minutes. And for you this is when you are in the zone. Would strict adherence to the technique give you an even higher boost than entering the zone? Can you experiment with that, and maybe I will too and report back. My initial thoughts are that entering the zone beats out Tomato timing, so roll with it when it happens.

    Your big question: What is one thing you learned when bootstrapping? I respect that you got down to the DNS level and learnt all that. It will help you out in the long run as the owner of a hosting business for sure.

    For me, I learned all about hiring and the applicable laws for salary, superannuation (retirement benefits) and things like that. It’s not an easy process, and can be very dry. But you want to put the effort in to make sure your getting it 100% correct. The last thing you want is to screw over someone you work with.

    • Thanks Jervis –

      Well, I did try and adhere to the “rules” of the pomodor technique for a couple of days. But I couldn’t stick to them. The 25 minute thing just doesn’t work for me. Nearly every task I do requires at least 45 minutes of focused “in the zone” time to really make progress. So basically, I’m no longer using the timer, but I am using the general concepts — specifically: Zero distractions while working (no more twitter, no email, no IMs), and when I’ve reached a milestone (finished building a feature, finished writing an article, whatever), I take a 5-10 minute break to check Twitter and read some blogs.

      I think the pomodoro technique’s 25 minute system works for people who have very structured work schedule, like a 9-5 office job. But my work sessions are spread out in random places throughout my week, which makes it tough.

      Ya, I can imagine things get complicated when bringing on a full-time salary employee. Perfect example of really having to learn all the ins and outs in order to actually get to that level.

  • Discovered you from Dan Andrews’ Q&A post and am really psyched to see a podcast focusing on entrepreneurial ACTION (as opposed to theory)!

    As for what I’ve learned while bootstrapping… well, everything. Never paid for a training course, just learned a ton about website creation, e-mail marketing, conversion optimization, info product creation, online advertising, etc. by just “picking it up” over the past 5-6 years in both my day job and my side hustle.

    Also, I’ve learned that you can sell a product before it exists… and that the resulting hustle to create and deliver the product to people who have already paid is a dynamite productivity technique. It’s the only thing I’ve tried that has actually worked.

    Looking forward to future episodes 🙂

    • Hey Shayna – thanks for checking out Bootstrapped Web! Lots of good episodes to come…

      Like you, I learned web design by doing it. First as an ameteur, building sites for my bands in college. Then I really learned by doing when I got my first job at a web design agency. My first day, they told me to build a complex navigation system (which I had never done before) and told me “figure it out”. I did, and that approach stayed with me to this day.

      Pre-selling is definitely very effective. Nathan Barry is a great example of someone doing this successfully, with his launch of ConvertKit.

      Thanks for tuning in!