The Bootstrapped Founder

Justin Jackson has been successfully bootstrapping Transistor.fm with a small team throughout the ups and downs of a shifting economy. He even rejected massive clients to be able to keep running a calm and self-funded business. Find out just how important it is to stay independent, resilient, and nimble, and what building on open standards has to do with that.

00:00:00 Justin Jackson

00:01:24 The world of ideas

00:10:32 Understanding the context of advice.

00:15:58 The importance of attribution

00:20:49 What’s the most important metric?

00:25:29 What’s your company for?

00:29:56 Having a team that can execute at the highest level

00:35:34 The repercussions of decisions

00:40:41 Simple things are more resilient than complicated things

00:45:26 Platform risk

00:51:22 The problem with centralized discoverability

01:00:53 The importance of open standards

My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm

The blog post: https://thebootstrappedfounder.com/justin-jackson-bootstrapping-transistor-fm-on-open-standards/ 

The podcast episode: https://share.transistor.fm/s/1740724b 

The video: https://youtu.be/y0yIZ-O8nNQ

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

Sponsored by Acquire.com.

Looking to build a successful SaaS business? Don't just focus on product-market fit. In this video, learn about the Solution-Workflow Fit, a crucial element to consider for success. Discover why the medium in which your solution is implemented and the workflow of your customers matter just as much as the technical side of your solution. See real-life examples and learn how to research your target industry's existing workflows, design your solution to fit between existing tools, and adapt your solution to fit your customers' needs. Achieving solution-workflow fit is key to creating a successful SaaS business that truly helps and empowers your customers.

My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm

The blog post: https://thebootstrappedfounder.com/the-saas-solution-workflow-fit

The podcast episode: https://share.transistor.fm/s/f9bf24a1

The video: https://youtu.be/eb5cS5Z1vBk

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

Rob Fitzpatrick is a serial entrepreneur, a writer, a community leader, and a very curious human being. I talk to Rob about building an incredibly complicated business, the world of self-publishing, what AI tools can and will do for humanity, and how to build communities that can run by themselves.

00:00:00 Rob Fitzpatrick
00:03:38 The challenges of building the Useful Books business
00:10:01 A rare breed
00:14:47 The passion discount
00:21:12 What’s changed in self-publishing?
00:26:43 What’s your pet peeve of the publishing industry?
00:32:48 Knowledge production
00:39:06 Short-term wins are not going to be around for long
00:42:21 Different voices for the same content
00:47:39 Prose be gone
00:54:26 Staying accountable in an accountability community
00:57:45 Late-stage communities
01:02:26 Rob’s passion and the purpose of communities

Brandon Sanderson's class on Indie Publishing: https://www.youtube.com/watch?v=tHdYX418PaA

The blog post: https://thebootstrappedfounder.com/rob-fitzpatrick-tinkerers-thinkers-and-teachers/
The podcast episode: https://share.transistor.fm/s/fd014e11
The video: https://www.youtube.com/watch?v=oqPF3a0px68

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This interview is sponsored by Acquire.com

How to secure your product, the business, and an eventual exit, including using established frameworks, outsourcing to secure third-party vendors, and having clear and complete account separation.

The blog post: https://thebootstrappedfounder.com/securing-your-saas/

The podcast episode: https://share.transistor.fm/s/6c645953

The video: https://www.youtube.com/watch?v=jNOr7BheIz8

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

Troy Hunt (of HaveIBeenPwned fame) is a cybersecurity expert who has been around long enough to be able to give actionable and pragmatic security advice without complicating things.

In our conversation, we chat about best practices for securing your SaaS business, how to get your family to be more secure, what it means to vet your vendors, if you should build your own authentication and why passwords just won't die.

After this conversation, you will know how to adequately secure your SaaS business without having to spend thousands of dollars.

00:00:00 Troy Hunt
00:00:59 The 1 thing SaaS founders get wrong
00:05:14 Why you shouldn’t build your own authentication
00:09:17 Library update management
00:13:42 Using third-party services
00:19:08 Data breaches and security expectations
00:26:39 Browser extensions
00:31:53 What is the right amount of security?
00:37:11 Giving your customers security options
00:42:13 The Have I Been Pwned + 1Password deal
00:48:18 Password managers

The blog post: https://thebootstrappedfounder.com/securing-your-saas-with-troy-hunt/
The podcast episode: https://share.transistor.fm/s/d2244c65
The video: https://www.youtube.com/watch?v=oRM-UrS440s

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This interview is sponsored by Acquire.com

Goodhart's law is powerful and important to remember for every creator: when a measure becomes a target, people tend to optimize their behavior to meet that target, which can lead to unintended consequences. You'll see examples of this law in action, including in education and social media, and learn the negative consequences of over-optimizing for follower count. But I won't let you go without prevention methods and tips for building a quality audience on social media.

00:00:00 Intro
00:01:51 Goodhart's Law
00:03:28 The Pitfalls of Focusing on Follower Count
00:07:32 The Negative Consequences of Over-Optimizing for Follower Count
00:09:18 Prevention Methods
00:12:16 How to Build a Quality Audience on Social Media

The blog post: https://thebootstrappedfounder.com/dont-fall-for-the-follower-count-trap

The podcast episode: https://share.transistor.fm/s/33be4469

The video: https://www.youtube.com/watch?v=P1HtIy5JyHI

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This episode is sponsored by Fathom Analytics.

Today, I’m talking to Matt Wensing — the founder behind Summit and tweeter of many often controversial things. We talk about bootstrapping a financial SaaS, how to deal with integrations, and when to take funding. Here’s Matt.

00:00:00 An exchange of stories
00:04:54 What’s your strategy?
00:09:31 Writing long-form
00:15:05 Bridging the gap between invention and commercialization.
00:19:56 Creators and salespeople.
00:25:58 How a little bit of cash can change the trajectory of your business.
00:34:34 Bootstrapping is not a shot in the dark
00:41:48 The importance of trust (in the crypto space.)
00:47:55 Centralization has to occur for other people to benefit
00:54:58 How not to leave people behind
00:59:29 How do you look at platform risk from both sides?
00:1:05:06 The nature of platforms

The blog post: https://thebootstrappedfounder.com/matt-wensing-publish-your-juicy-thoughts/
The podcast episode: https://share.transistor.fm/s/f7deea33
The video: https://www.youtube.com/watch?v=2pBYsl1UxeY

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This interview is sponsored by Acquire.com

Stair-stepping into software entrepreneurship is a great way for developers to start their own businesses without taking on massive risks. Building a plugin on an established platform allows developers to leverage existing user bases and traffic to grow their business quickly, while also being aware of the risks associated with platform dependency, profit-sharing, and limited flexibility.

My interview with Collen Schnettler: https://www.youtube.com/watch?v=PpcYTO5x3cY
Rob Walling's Stair-Stepping: https://robwalling.com/2015/03/26/the-stair-step-method-of-bootstrapping/
Preetham Nath: https://www.preetamnath.com/blog/grow-shopify-micro-saas-to-25k-mrr-in-14-months

The blog post: https://thebootstrappedfounder.com/stair-stepping-with-plugins-platforms-to-build-on/

The podcast episode: https://share.transistor.fm/s/51643e63

The video: https://www.youtube.com/watch?v=PjOHqn4PJZM

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This episode is sponsored by Drata.

Today, I’m talking to Colleen Schnettler, co-founder of Hammerstone and build-in-public podcaster. We talk about getting bootstrapper-compatible funding, juggling way too many projects, and selling a business when you know it’s time to move on. Here’s Colleen.

00:00:00 A lot of podcasts
00:06:01 Building on Heroku
00:12:25 Building on Marketplaces
00:16:59 Dealing with support requests
00:21:49 Pressure to sell?
00:26:27 Hammerstone
00:31:24 Business Value
00:35:46 Value of value
00:41:11 The risks of having just a few big customers
00:46:12 Getting bootstrapper funding

The blog post: https://thebootstrappedfounder.com/colleen-schnettler-stair-stepping-into-saas/
The podcast episode: https://share.transistor.fm/s/281dbe46
The video: https://www.youtube.com/watch?v=PpcYTO5x3cY

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This interview is sponsored by Acquire.com

Arvid shares what writing can bring to the founder table.

Self-funded entrepreneurs can benefit from honing their writing skills, as it can be used to communicate ideas and thoughts clearly, attract attention, foster relationships, and build a personal brand.

The blog post: https://thebootstrappedfounder.com/writing-for-founders/
The podcast episode: https://share.transistor.fm/s/735924e4
The video: https://youtu.be/1R5scFwM5Xw

You'll find my weekly article on my blog: https://thebootstrappedfounder.com
Podcast: https://thebootstrappedfounder.com/podcast
Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/
My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/
My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This episode is sponsored by Drata.