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.

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.

How I went from $100-an-hour programming to $X0,000-a-week consulting.

If you don’t subscribe to Patrick McKenzie’s newsletter, you should.  It’s loaded with ideas for running your business and is especially good at helping those running software companies or consulting practices.

As someone who charges for time, it’s really hard being comfortable asking for what your worth.  Clients tend to try to negotiate a better rate and we quickly learn we have a desired target rate and a rate we are willing to settle on to satisfy the client.

Patrick’s most recent newsletter titled How I went from $100-an-hour programming to $X0,000-a-week consulting, is a really great look at pricing services and moving from an hourly consultant to selling time in blocks.  The main point that hit home most for me was how clients are more willing to pay for value, rather than time.  It sounds obvious but wasn’t for me:

I have an Internet buddy in Chicago named Thomas Ptacek. We met on Hacker News. He’s the #1 poster by karma and I’m #2. Since we apparently share the same mental disease characterized by being totally unable to resist comment boxes, I decided to invite Thomas out to coffee. My agenda, such that it was, was to gossip about HN threads.

Thomas runs a very successful webapp security consultancy, Matasano. (Brief plug: they’re hiring and if it weren’t for this business thing I’d work there in a heartbeat: some of the smartest folks I know doing very, very interesting work which actually matters. If you can program they’ll train you on the security stuff.)

Anyhow, after we got our coffee, Thomas invited me into their conference room. We talked shop for three hours: Thomas and his VP wanted to hear what I’d do to market their products and services offering. I had been writing about how I marketed Bingo Card Creator for a while, and started applying some of the lessons learned to their content creation strategy.

(The actual contents of the conversion are not 100% germane to the story, but I blogged a bit about it and Thomas posted his thoughts on HN. Long story short: programmers can do things which meaningfully affect marketing outcomes.)

At the end of the conversation, Thomas said something which, no exaggeration, changed my life.

Thomas: Some food for thought: If this hadn’t been a coffee date, but rather a consulting engagement, I’d be writing you a check right now.

Me: Three hours at $100 an hour or whatever an intermediate programmer is worth would only be $300. Why worry about that?

Thomas: I got at least $15,000 of value out of this conversation.

What an eye-opener this must have been, it would have been for me.  I think I would have had the same epiphany:

This is, far and away, the most important lesson to learn as a consultant. People who are unsavvy about business, like me in 2009 or like most freelancers today, treat themselves like commodity providers of a well-understood service that is available in quantity and differentiated purely based on price. This is stunningly not the case for programming, due to how competitive the market for talent is right now, and it is even more acutely untrue for folks who can program but instead choose to offer the much-more-lucrative service “I solve business problems — occasionally a computer is involved.”

Thinking this way and selling yourself as such makes so much sense.  Why didn’t I think of it?  I think most consultants, contractors and freelancers are so trained by their peers and clients to think they are just a commodity that we don’t know to think differently until it’s explained so well.

The newsletter goes on to explain all the benefits of billing weekly; all reasons make sense.  Time to make some changes.

So, go now and read the newsletter.  Great stuff.

Bootstrapping Your Ideas

bootstrap As an individual entrepreneur it is sometimes hard to get things done with our limited time in a day and limited financial resources.  I find it helpful to have a large base of contacts which I know well and can reach out to when I need a hand, but timing may not always be right.

Derek Sivers had a great post recently titled "How to hire a programmer to make your ideas happen".  Derek discusses some great points when looking to bring your idea to fruition and suggests using services such as oDesk, elancer, guru.com and vworker:

Go to the following sites to open an account at each: elance.com, guru.com, odesk.com, vworker.com

Post this short project at each site. Use their escrow service. Location of provider doesn’t matter – they can work from anywhere. Don’t pay for a highlighted listing. Pay by the hour. Set the bidding time limit to 7 days. Most bids will come in the first 3 days.

You’ll get many offers, but if they don’t have your magic phrase at the top (“I AM REAL” or whatever), delete them. This is very hard to do, since you’ll feel thrilled that so many people are offering to help, saying things like, “We have looked at your project and would be glad to complete it immediately,” but trust me and delete those. If they didn’t read something marked as VERY IMPORTANT already, you don’t want to work with them.

Also important: Only go for providers who have great reviews from many past customers. This shows they are used to working this way through this site. Decline bids from providers without many great reviews.

Don’t aim for the lowest bid. Use these sites to find someone that seems great and capable, even if they are twice as much as the lowest bid, they might work 10 times faster and better.

Each of these sites has its quirks, so sorry I can’t recommend specifics for everyone. But be considerate and nice, once they’ve mentioned your VERY IMPORTANT phrase to prove they really read your requirements. That’s cold enough. Once they’ve passed that test, be very responsive and friendly.

I have worked with a couple of these sites and have had the best experiences with oDesk, of course your mileage may vary.  Taking slow, careful steps when working with these resources can lead big jumps toward your goals.

Personal Experience

I am not a proponent of companies laying off local developers and outsourcing work to save money, I despise the idea.  If you have profitable business and can afford the full-time efforts a local developer, do it.  Sometimes when bootstrapping your business and keeping the bills paid, outsourcing what you can may help get a kickstart to idea.

I try to find people on oDesk who are individual freelance developers setting out on their own or supplementing the income they already have.  It is not always easy working with developers from these sites, but I have found a few rules I try to stick to which has helped:

  • Reasonable Time zone – this is one of the biggest that has bitten me in the past.  When working with developers on these sites fine a time zone you are comfortable within.  I have hired developers both in India and other locations 12+ hours difference in time zone from myself and it does not work very well.  It seems when I needed to talk with them they were sleeping and we only conversed over email, making things hard.  It often took days to discuss an issue.  I require developers to be willing to either work in my time zone or overlap some number of hours from mine to theirs. 
  • Reliable Commitment – some of the developers you will find often are supplementing their income with some side work.  It is hard to work a 40 hour a week job and commit to any substantial side work.  If the developer has a full-time job make sure to ask what they can actually commit with regards to hours.  I have personally experienced developers committing to 20 hrs a week but barely making 10, which at that point they make themselves scarce and the project suffers even more.  So, ask for the commitment and reiterate the need for a realistic commitment and monitor closely.
  • Code Quality Monitor – it’s hard to get a real idea of the quality of code coming from an offshore resource.  I monitor all commits to GitHub and make sure code is up to par, for now..I can always refactor later but the goal is to get the job done.

It has taken me a while to be better able to choose a good developer through oDesk.  It certainly can be done but takes some trial and error to see what best works for you.

The Long Term

Hiring local developers is my long-term goal for my business but until I can afford the commitment to hire full-time, I will use freelancers I can afford.  I have hired before and had to lay them off, it is not a fun thing to do. 

Brining on these inexpensive contractors can allow you to try out an implementation of an idea long before you hire and gets it to market that much faster and so much cheaper.  It is very hard to go wrong indeed.

Using these type of outsourced resources are applicable to both those full-time freelancers trying to get an idea developed but the idea of doing it on the side just never works.  This also works for someone with a full-time job trying to do the same thing, get something going on the side during those “extra” hours that never seem to appear.