8 More Great Bootstrapping Podcasts to Jumpstart Your Day

bootstrapping podcasts

I listen to a lot of bootstrapping podcasts throughout the year, trying new ones and retiring those that stop producing new episodes or I lose interest. I wrote up a list a while ago about bootstrapping, 7 Great Bootstrapping Podcasts to Jumpstart Your Business Today, and thought it was time for an update.

8 Great Bootstrapping Podcasts

I’m not including any bootstrapping podcasts from my previous list, only ones I’ve discovered and listen to on a regular basis today. The old list still includes some favorites so you should check that list out too.

This list is not me pulling together a quick list but is curated since the last list. I have probably reduced 50 podcasts down to this final 8.  I hope you find some new gems here.


ConversionAid podcast has turned out to be one of my favorites. Hosted by Omer Khan, who is an ex-Microsoftie and runs ConversionAid to help companies “create software that sells”.

Omer interviews entrepreneurs who have taken an idea and oftentimes a unique approach to finding paying customers. The format gives listeners answers to the questions we all have trying to start and run a software or service business. Each episode seems to introduce a business and founder I never knew existed. Discovering new businesses, business models and their leaders gives new perspective to how I think about my business.

Every episode has been great and makes me look forward to the next.

Website: conversionaid.com/podcast


TropicalMBA is:

a popular podcast and blog dedicated to the growing movement of location independent entrepreneurs worldwide.

I’ve been listening to this podcast for a while and always learn something new and valuable. Each episode is focused, addressing a particular question or topic. Some episodes resonate more than others. Recent gems include:

I advise you visit the website for each episode you listen to. If you just listen in iTunes or other podcast application you’re missing out. The show notes are as valuable, if not more, than the audio itself. You’ll find tons of shows notes, links that reference other episodes with similar content and not to mention the great comments from listeners.

Website: tropicalmba.com

Bootstrapped Web

Hosted by fellow CT resident Brian Casel and left-coaster Jordan Gal, Bootstrapped Web is a podcast that chronicles the journey Brian and Jordan take bootstrapping their own businesses.

Episodes discuss aspects of their businesses, updates and business lessons learned along the way as well as interviews with fellow entrepreneurs that compliment their own journey. I appreciate the candidness in each episode. It is so easy and natural to discuss all the wins we make each day but I think more important to reflect on the failures too so that we learn from them. Their guidance is solid and battle tested..great podcast.

Website: bootstrappedweb.com

Chasing Product

Hosted by Chris Hawkins, Chasing Product is an interview style podcast with people who have taken the leap to create software products. Chris reflects on his own pursuit of a product and the challenges he faces with a seemingly simple, yet elusive task. So many software developers are in jobs they don’t like and have that idea in their head they would like to create and live off of for years to come.

These interviews profile many that have done just that; left their job and are living the dream. OK, maybe the dream isn’t exactly as they had envisioned but it is independence just the same. Great stories and Chris has a great radio voice. Enjoy!

Website: chasingproduct.com


These are generally short interviews, 30 min or less, with entrepreneurs from the companies you have probably heard of before. The questions are laser-focused and give listeners actionable items to try in their own businesses.

Each episode is has a single theme or takeaway but inevitably, you learn much more. These folks are entrepreneurs themselves and produce a lot of episodes, more than I can listen to..not sure how they do it. The win for me is the variety.

Website: rocketship.fm

Art of Value

A tough concept to grasp for so many is providing products and services to our clients in terms of value. Value is the language of business owners. As a software developer, I am learning this lesson. It’s easy to create things we think are worth building but no matter what we build, it has to have value to our customers or they won’t buy.

Art of Value is all about creating those happy customers and earning more money. Episodes are interview format and talk with people from all types of businesses but focus on one theme..value.

Transitioning from hourly to value pricing is my #1 focus in my own business today. Showing customers the value I can deliver vs. the commodity hourly resource my company has been over the years. This podcast has been key in my thinking about the why and how to make that move.

Website: artofvalue.com

Marketing Optimization

Marketing is hard. Marketing is especially hard for developers and Marketing Optimization really helps distill down the concepts. Topics are broad but include everything from SEO to UX design to conversion optimization and beyond.  Each episode is pretty deep, so at least for me it takes some focused listening.

Another nice touch is that each episode has a video so you can watch the interviews.

Website: marketingoptimization.tv

Rogue Startups

This is a new podcast with episodes starting the first of the year. Newer episodes have two hosts and they interview entrepreneurs who have specific skills (productized consulting for example) or they discuss topics important to running your business. Episodes are roughly and hour and packed with good content and happy dialog:

Never before in history has it been easier for talented individuals to escape the confines of the rat race society and go down their own path.  Our hope is to inspire and educate you on how successful startup entrepreneurs have done that.  This is no pie in the sky podcast with esoteric BS about business, Make Money Online schemes, and any other “flash in the pan” type business.  This is for people just like you and me who know there must be a better way, and want to find it.

Website: roguestartups.com

Hack the Entrepreneur

I’ve only been listening to Hack the Entrepreneur for the past couple months but look forward to all new episodes. The format for this one is interview style but takes unique approach:

Hack The Entrepreneur  is a show which reveals the fears, habits, and inner-battles behind big name entrepreneurs and those on the path to success. Hack The Entrepreneur is released three times per week on Monday,Tuesday, and Thursday mornings.

On Hack the Entrepreneur we know that everyone is unique and has to find their own path to success, but after speaking to entrepreneurs every day as part of my own successful business I became obsessed with the idea of finding the ‘replicable’ things behind leading names and people on their way up to try to find patterns.

The insight you gleam from each of these interviews is really priceless. It’s nice to learn about the angle we don’t normally hear about.

Website: hacktheentrepreneur.com

These are the bootstrapping podcasts I’ve found and stuck with since the last list. I try new ones all the time and forget about the ones that don’t resonate and add value to my own pursuits.

Suggestions are always welcome, please add those to the comments so I can give a listen. Thank you.


Dave Winer is always working on something new, something creative and innovative. While running out of something good to listen to Dave cam e up with Podcatch.com, a curated list of podcasts from friends.

New shows from my friends’ favorite feeds. That’s what I need when I’m rushing to get out of the house and don’t have time to load up my phone with good shows. I’m getting a lot more value for my podcast-listening time. And so can you!

The list is if full of a variety of podcasts so there has to be something to catch your ear.

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I have already discovered a couple new podcasts to add to my Instacast client.

Talking about Building iOS Application on The Tablet Show Episode 85

I was a guest recently on The Tablet Show with Richard Campbell and Carl Franklin, to talk about iOS development, client projects, API’s with Ruby on Rails and creating applications with interactive back ends.

I think it turned out pretty well but I really can’t stand listening to my own voice, so please give it a listen and decide for your self.


Thanks to Richard and Carl for having me on the show.

7 Great Bootstrapping Podcasts to Jumpstart Your Business Today


I love podcasts.  I listen to them in the car, walking or sometimes even when working.  I can’t get enough of the good ones and you probably can’t either.

Since attending MicroConf last week I can’t stop thinking about creating products, recurring revenue and talking about all the facets of running a product business.

I thought I would pull together my short list of the podcasts for boots trappers, entrepreneurs, startups or whatever you might call yourself, that I listen to and gain value. Some of these I have just recently discovered, while others, I have been a fan since their inception.  

If there are some podcasts that should be on this list, please feel free to point them out in the comments.

I hope you find as much value in these as I do:

Startups for the Rest of Us

Rob Walling and Mike Taber, creators of MicroConf have been producing this podcast for a long time.  Startups for the Rest of Us is exactly what it sounds like, a podcast for regular people trying to startup a business.  

The format of the show begins with Rob and Mike talking about what’s going on with their own businesses and related products.  Each show follows a theme where the duo discusses the focused topic.   


Ian Landsman of HelpSpot fame and Andrey Butov recently started Bootstrapped.fm and after listening to a few episodes I find myself looking for new episodes in iTunes.  

The format of each episode is similar to Startups for the Rest of Us, where Ian and Andrey discuss their bootstrapping adventures.  It’s nice to hear different aspects of different types of bootstrapped software businesses, Ian with his SaaS application and Andrey with mobile applications.  

Lots of topics crossover, whether doing SaaS or mobile applications but there’s always valuable lessons to learn.

Bootstrapped with Kids

Bootstrapped with Kids  is also a recent addition to my podcast collection.  Brecht Palombo is the host and who also gave a great attendee talk at MicroConf. 

The topics are dear to the hearts of boostrappers and include product ideas and other aspects of the trade.

Product People

Kyle Fox and Justin Jackson are the hosts of Product People, a podcast I only recently discovered.  It is quickly becoming one of my favorites.  

The interviews are with, you guessed it, people who are successful product builders.  The interview style is very dynamic and doesn’t follow a script as you might have heard in other interview format podcasts.  I continually find myself thinking of the questions I would ask the guests and as it happens, these guys are asking those questions.  I’m sure the people who see me walking each day and nodding my head in agreement think I’m crazy.

Some recent interviewees include:

  • Amy Hoy
  • Nathan Barry (two parts and fantastic)
  • Hiten Shah
  • Jason Fried
  • Brennan Dunn
  • Rob Walling
  • Patrick McKenzie


Mixergy is actually an old favorite I have mentioned here before.  Andrew Warner does a fantastic job of interviewing entrepreneurs from all different industries and all different stories.  

Andrew is the marathon man of podcasting with tons of episodes and counting.  Plenty of backlog to go through and enjoy.

If you prefer the episodes are online and can watch the videos of Andrew interviewing his guests.  The benefit is see the guests facial expressions, small but nice sometimes.

Kalzumeus Podcast

Patrick McKenzie is a highly respected bootstrapped entrepreneur in the software industry who speaks at a few conferences and draws a crowd.  Patrick has discussions with various entrepreneurs ranging from angel investing to sales and marketing.  The episodes are not very frequent but they are solid and very much worth the wait.  Patrick includes transcripts in the podcast page so if you would rather digest the great material at a slower pace, it’s there.

Entrepreneur on Fire

This is another relatively new discovery for me.  The format is a series of interviews with entrepreneurs who have a wide range of skills, backgrounds and business types.  Entrepreneur on Fire is a very active podcast and publishing episodes at a feverish pace (5 days a  week), not sure I can keep up.

More Great iOS Developer Podcasts

Podcast RSS

I subscribe and listen to a lot of podcasts.  I wrote about some of my favorites before, 7 Great iOS and Mac Developer Podcasts to Learn from Today, and I wanted to share some more today.


Hosted by Myke Hurley, CMD+Space is a show with interviews various independent Mac and iOS developers from the perspective of running their businesses and how they got to where they are today.

So many developers go independent all the time and could use some solid guidance.

CMD+Space is on then 70decibels network which hosts many other shows that you might find interesting.


Hosts Guy English and Rene Ritchie have been running this podcast for the past few weeks but it quickly became one to get sync’d to my iPhone for listening while driving or daily walks.

Debug is also an interview show with well-known Mac and iOS developers.  As often happens while I listen to interviews various questions come to mind that go unanswered, not the case here.  These guys seem to ask the questions I want answered.  Coincidence?  Most likely but the great questions result in solid advice.

Identical Cousins

Hosted by Michael and Brent Simmons, they discuss various topics important to Mac and iOS developers who are mainly independent but also those gainfully employed at companies large and small.

I stumbled across Identical Cousins while listening to another podcast, which is often the case.


This podcast is a bit different with a focus on the design side of mobile development for Mac, iOS and Android applications.

Iterate is hosted by Rene Ritchie and others.  Rene seems to be a repeat name here and other podcasts including MacBreak Weekly.