The Bootstrapped Founder

Here are my personal strategies for achieving consistency in content creation, which encompass implementing accountability systems, connecting with my audience, and reaping financial and lifestyle rewards. Additionally, I explore the difficulties of maintaining motivation and the vital role of community in this process.I recount my own story, beginning with the launch of a blog and ultimately leading to the development of a self-perpetuating content creation cycle. Throughout this journey, I've expanded my income sources by securing sponsorships and authoring books. By highlighting the significance of consistency, I aim to inspire others to adopt it as a guiding principle in their own creative endeavors.My new podcast project: Arvid & Tyler Catch Up / https://catchup.fmThe blog post: https://thebootstrappedfounder.com/how-i-stay-consistent/The podcast episode: https://share.transistor.fm/s/7bd407f4The video: https://youtu.be/K3qSwVT1Sh0 You'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind me on Twitter: https://twitter.com/arvidkahl/

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 Jackson00:01:24 The world of ideas00:10:32 Understanding the context of advice.00:15:58 The importance of attribution00:20:49 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 level00:35:34 The repercussions of decisions00:40:41 Simple things are more resilient than complicated things00:45:26 Platform risk00:51:22 The problem with centralized discoverability01:00:53 The importance of open standardsMy new podcast project: Arvid & Tyler Catch Up / https://catchup.fmThe 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-O8nNQYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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.fmThe blog post: https://thebootstrappedfounder.com/the-saas-solution-workflow-fitThe podcast episode: https://share.transistor.fm/s/f9bf24a1The video: https://youtu.be/eb5cS5Z1vBkYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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 Fitzpatrick00:03:38 The challenges of building the Useful Books business00:10:01 A rare breed00:14:47 The passion discount00:21:12 What’s changed in self-publishing?00:26:43 What’s your pet peeve of the publishing industry?00:32:48 Knowledge production00:39:06 Short-term wins are not going to be around for long00:42:21 Different voices for the same content00:47:39 Prose be gone00:54:26 Staying accountable in an accountability community00:57:45 Late-stage communities01:02:26 Rob’s passion and the purpose of communitiesBrandon Sanderson's class on Indie Publishing: https://www.youtube.com/watch?v=tHdYX418PaAThe blog post: https://thebootstrappedfounder.com/rob-fitzpatrick-tinkerers-thinkers-and-teachers/The podcast episode: https://share.transistor.fm/s/fd014e11The video: https://www.youtube.com/watch?v=oqPF3a0px68You'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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/6c645953The video: https://www.youtube.com/watch?v=jNOr7BheIz8 You'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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 Hunt00:00:59 The 1 thing SaaS founders get wrong00:05:14 Why you shouldn’t build your own authentication00:09:17 Library update management00:13:42 Using third-party services00:19:08 Data breaches and security expectations00:26:39 Browser extensions00:31:53 What is the right amount of security?00:37:11 Giving your customers security options00:42:13 The Have I Been Pwned + 1Password deal00:48:18 Password managersThe 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.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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 Intro00:01:51 Goodhart's Law00:03:28 The Pitfalls of Focusing on Follower Count00:07:32 The Negative Consequences of Over-Optimizing for Follower Count 00:09:18 Prevention Methods00:12:16 How to Build a Quality Audience on Social Media The blog post: https://thebootstrappedfounder.com/dont-fall-for-the-follower-count-trapThe podcast episode: https://share.transistor.fm/s/33be4469The video: https://www.youtube.com/watch?v=P1HtIy5JyHIYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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 stories00:04:54 What’s your strategy?00:09:31 Writing long-form00:15:05 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 dark00:41:48 The importance of trust (in the crypto space.)00:47:55 Centralization has to occur for other people to benefit00:54:58 How not to leave people behind00:59:29 How do you look at platform risk from both sides?00:1:05:06 The nature of platformsThe blog post: https://thebootstrappedfounder.com/matt-wensing-publish-your-juicy-thoughts/The podcast episode: https://share.transistor.fm/s/f7deea33The video: https://www.youtube.com/watch?v=2pBYsl1UxeYYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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=PpcYTO5x3cYRob 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-monthsThe blog post: https://thebootstrappedfounder.com/stair-stepping-with-plugins-platforms-to-build-on/The podcast episode: https://share.transistor.fm/s/51643e63The video: https://www.youtube.com/watch?v=PjOHqn4PJZMYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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 podcasts00:06:01 Building on Heroku00:12:25 Building on Marketplaces00:16:59 Dealing with support requests00:21:49 Pressure to sell?00:26:27 Hammerstone00:31:24 Business Value00:35:46 Value of value 00:41:11 The risks of having just a few big customers00:46:12 Getting bootstrapper fundingThe blog post: https://thebootstrappedfounder.com/colleen-schnettler-stair-stepping-into-saas/ The podcast episode: https://share.transistor.fm/s/281dbe46The video: https://www.youtube.com/watch?v=PpcYTO5x3cY You'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind 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/735924e4The video: https://youtu.be/1R5scFwM5XwYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind me on Twitter: https://twitter.com/arvidkahl/This episode is sponsored by Drata.

Today, I’m talking to Hassan Osman— he’s the host of Writer on the Side, and himself a prolific writer. We talk about crafting books that sell (and keep selling), self-publishing on Amazon, and how to write while having a full-time job. Here’s Hassan!00:00:00 Introduction to Hassan Osman00:05:59 Slowly shifting your perspective00:10:48 Do you update your books that you have written?00:17:24 How short-sighted publishers can be00:24:29 The importance of the time component in your book00:29:12 The ROI if a diverse range of topics00:34:47 Pick topics that are intersectional, not generic00:41:43 You don’t need to write a big book to be successful00:47:03 Using a marketplace vs doing it on your own00:52:15 Investing in yourself and your public brand00:56:22 Selling on Amazon and Udemy The blog post: https://thebootstrappedfounder.com/writing-on-the-side-with-hassan-osman/The podcast episode: https://share.transistor.fm/s/b67953c3The video: https://www.youtube.com/watch?v=Tsx78OkIiEkYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind me on Twitter: https://twitter.com/arvidkahl/This interview is sponsored by Acquire.com

Arvid talks about how applied kindness builds a brand and an audience.In a hostile world, many founders isolate themselves, but this isn't sustainable. Kindness changes the world, so be honest when self-promoting and set boundaries with hostility. Kindness can be seen in every aspect of life, creating a cycle of positive change.The blog post: https://thebootstrappedfounder.com/be-the-kindest-person-in-the-room/The podcast episode: https://share.transistor.fm/s/0f9109d5The video: https://www.youtube.com/watch?v=IY3xrnn82QgYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind me on Twitter: https://twitter.com/arvidkahl/

KP talks about building in public, sharing your journey, and becoming a respected community member.Today, I’m talking to KP — the build-in-public guy. KP has been a pillar of the indie hacker community, and we talk about how to involve yourself, empower others, and eventually build a community around your personal brand and the things you care about. Here’s KP.00:00:00 KP’s founder hotline00:04:32 The struggle beneath success00:12:11 The connection between teacher and student00:16:26 Sharing what you know00:19:18 The importance of staying in the community00:23:28 Serial entrepreneurship is severely misunderstood00:29:46 An iterative approach to learning00:33:38 Removing yourself from your ask00:37:14 Sales and trust00:42:21 The fear of losing your market00:49:23 The importance of having a mindset of “I’m not the XYZ guy”00:55:12 Quality doesn't matter as much as we think- Building an Authentic Personal Brand with KP- Find your Following, my Twitter course — now including Find your Following Essentials, the 7-day Twitter crash course- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.

Negative reviews are an important part of the customer experience, as they provide valuable feedback to creators about how their product or service is being perceived. Reviews can be a source of frustration for founders, as they may not reflect the quality of the work, but rather the disconnect between the customer's expectation and the reality of the product. It is important for creators to stay mindful of how they position their products in the marketplace and ensure that their messaging aligns with the customer's experience.00:00:00 Negative Reviews00:01:11 Reality vs Expectation00:02:43 Positioning ErrorsThe blog post: https://thebootstrappedfounder.com/negative-reviews-are-good-for-you/The podcast episode: https://share.transistor.fm/s/46b3421dThe video: https://www.youtube.com/watch?v=fulkEU1JAVUYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find your Following: https://findyourfollowing.comFind me on Twitter: https://twitter.com/arvidkahl/This episode is sponsored by Drata.

Brennan shares the secrets to using emails to build relationships and increase your revenue.Today, I’m talking to Brennan Dunn, the founder of Palladio, co-founder of RightMessage, and general email expert. As a newsletter author myself, I took to this opportunity to learn as much as possible about personalizing and optimizing my email strategy. You’ll also hear what most people get wrong in email marketing. Here’s Brennan.00:00:00 Brennan Dunn00:00:48 What is up with email clients?00:05:05 Integrating with large platforms00:08:34 Maybe build a competitor?00:12:12 Emails and metadata00:16:20 Email personalization and how it works00:22:07 How do you get started with this?00:25:28 Focusing time and effort on certain platforms00:31:24 The difference between an email list and a newsletter00:36:30 The importance of segmentation00:41:06 Use segmentation to increase your list00:48:56 Customer centric marketing00:54:24 Is email the right medium to de-risk?00:59:20 Don’t over-saturate- Mastering Email Marketing with Brennan Dunn - Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.00:00:00 Laura's journey00:01:10 The parable of the monkey and the pedestal.00:02:28 A cultural problem00:03:36 Reflecting on the monkey- The Monkey and the Pedestal- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurshipIf you're interested in Descript, go and check it out here.You can also watch this episode as a video on YouTube.

Today, I’m talking to Laura Elizabeth. She co-hosts the Non-Tech Founders podcast and runs several products as a non-technical founder. We talk about outsourcing, trust, and building an audience around your business. Here’s Laura!00:00:00 Laura Elizabeth00:02:10 Running a non-technical founder podcast00:09:28 Hiring the right people00:12:14 Hiring people who can do something you can't00:17:27 Being able to do everything is both awesome and frightening 00:20:13 Experimenting with different modes of delegating00:25:45 Establishing an internal process for your business00:30:00 On Phrasing00:36:30 The importance of having a mentor00:42:04 Providing the fertile ground for luck to strike00:45:04 The hardest part is overcoming your inner demon00:52:56 Why it's good to have an expert for website personalization00:56:33 Where you can follow Laura- Building Software Products As a Non-Technical Founder With Laura Elizabeth- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.- Expanding Your Opportunity Surface- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurshipIf you're interested in Descript, go and check it out here.You can also watch this episode as a video on YouTube.

Today, I’m talking to Daniel Fayle — co-founder of Chekkit, a business he and his team have boostrapped to $2mil in ARR. We’ll touch on finding the right vertical to get started, how to do things that don’t scale, and what choices need to be made to get a business to 7 figures. 00:00:00 Daniel Fayle00:05:35 Getting started with Chekkit00:09:00 Local marketing & picking verticals00:12:05 When to hire a team?00:17:25 Integrations00:22:33 Pricing choices00:25:32 How to be inspired by competition?00:29:54 The importance of customer support00:36:31 Setting limits on free trials00:41:55 Use the tech that your customers use00:47:15 How to stay on top of your game- Door-to-door to $2M ARR with Daniel Fayle- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.