SaaS Bootstrapping Journey - Moving from MVP into Automation & Optimization

Documenting my journey bootstrapping a podcast smart links software service. Moving beyond lean MVP into optimizing the workflow and product with automation, onboarding, and self-serve support.

• By Scott Mathson

Years ago, I was certain that I was going to become a famous musician and recording studio owner.

And before that, a pro skateboarder.

My path and the trajectory of how I got to where I am is a bit of a winding path.

But before immersing myself deeper into marketing, web development, and a whole gamut of full-stack startup roles, I had my nose to the grindstone in audio production and music. Initially learning and playing drums and then gravitating towards learning guitar, bass, songwriting, banjo, and so on.

Mid-2000’s I was running a recording studio for area musicians, offering audio production services. During this time I learned more about podcast production and eventually started hosting a show (since archived). Audio was one of my first entrepreneurial experiences and music has always been important to me.

Rooted in arts and creativity, the path I’ve chosen to travel has delved deeper into the more technical side of things. Website design and dev led to freelancing and agency ownership, content to day-jobs and side projects, marketing and product to full-time day-jobs, engineering, design, entrepreneurship, and beyond.

I’m always creating, always making things.

In the same vein, I recently launched Plink - a podcast smart links service. Holding to my newsletter’s promise to openly document my corner of the web and share projects, I’ll be sharing more about Plink and my journey of bootstrapping this venture.

So let’s dive into what Plink actually is, why I’m creating it, and the problem it solves. As well as sharing decisions I’m making, struggles I’m overcoming, and insights into business and product optimizations.

Table of Contents:

What is this podcast smart linking product? And why create it?

Plink is a smart-links-as-a-service, software as a service (SaaS), podcast marketing product. I’m creating this to solve pain-points for podcast creators and consumers, alike. Both sides of which is obvious have been experiencing disconnect.

Being a podcaster (Makerviews) and fan of many a pod myself, I’ve experienced firsthand the time-intensive, manual task of link-collecting for listening platforms when promoting shows and episodes. On the consumer’s side, an over-prioritization of iOS Apple Podcasts makes this medium seem non-accessible to Android and other consumers, especially first-timer listeners.

Plink makes smart links that anyone, any device, can open and play. Offering a podcast marketing solution for creators and enhancing consumer’s user experiences, no matter the device, operating system, or geographical location.

Using Plink and smart linking everyone, especially first-time podcast listeners who do not yet have an app preference (or don’t know that one exists yet), will automatically direct them into pre-installed, native applications in a variety of devices. There are more features I’ve developed like Show Page podcast app links landing pages, among others. And plenty more is continually being prioritized and added onto the roadmap.

At it's core, Plink podcast smart links will detect devices and route accordingly:

  • iOS users auto-open Apple Podcasts app
  • Android users auto-open Google Podcasts app
  • desktop users land on the podcast's Show Page with other app links

Hover mouse over Show Page + scroll to see app link options.

View Crime Junkie's Show Page

How creators link to shows from a variety of platforms directly impacts consumer’s experience and the accessibility of the entire ecosystem. I’m very passionate about this and wrote more about podcast discovery and accessibility on the Plink blog.

Smart linking everyone, especially current non-listeners who do not yet have a podcast app preference, will automatically direct them into pre-installed, native applications on their mobile devices. Offer everyone better user experiences, no matter the device, operating system, or geographical location. How podcasts are discovered & shared - Plink

Outside of my day-job and life at home, I’ve been laser-focused on developing this service and solution for the better part of the past few months. From market research, customer interviews, product planning and development, private beta testing, and beyond. I publicly shipped a minimum viable product (MVP) of Plink at the start of Q2 2019, building the MVP with Eric Ries’s lean startup methodology in mind.

It’s an MVP nonetheless and in order for it to scale, it’s time to move beyond the proven-to-be-viable MVP.

Moving beyond MVP

I’ve already been moving into the next phase and incrementally improving things and squashing minor bugs. Currently, I am very confident and pleased with where the product is at. It has proven the initial hypothesis, solves a problem, saves creators time, and improves consumer’s listening experiences.

Hell, I’ve even added features like the ability to help podcasters earn more, passive money in adding their Apple Services (previously iTunes) affiliate IDs to paid, custom links. This is all very exciting to me, as Plink continues to be validated through further adoption, positive feedback and reviews, and an increasing user-base of both free and paid customers of the product.

But I’ve recognized that it’s actually time to shift the majority of my focus away from the core product. Away from ideating, developing, shipping, and marketing new (and optimizing current) features.

It’s time to transition my focus into optimizing things for the business. In order for this to scale, I need to automate manual tasks, re-work onboarding, scale self-serve support, documentation, and other core business optimizations.

Recently I was listening to The SaaS Podcast, hosted by Omer Khan an ex-Microsoft, Seattle-based SaaS coach and entrepreneur. Episode number 207 featuring guest Tyler Tringas really resonates with me. I’ve found myself re-listening to this episode and nodding along, agreeing, and seeing many parallels between his founder’s journey and my own.

This episode follows the journey of what Tyler calls his “Micro-SaaS” (very targeted niche, small team, focused product) business that he previously created and has since sold. His MVP of what became Storemapper was shipped on a lot quicker timeline than most. After a roundabout 30-hour international flight from San Francisco to Buenos Aires, his niche Shopify store locator app was shipped. And within 24 hours he had paying customers.

This entire story from idea to acquisition is quite amazing. I’ll be referencing more of Tyler’s work throughout.

Making v1. And making it work on a budget with third-party solutions

With the product idea and problems to solve front-of-mind, I ran a period of customer and market research, customer interviews, product planning, and then into initial product design and development. From there, I opened a window of time dedicated to private beta testing with a handful of folks. The feedback gained during this period was so invaluable - shoutout and thanks to UNCO podcast host Timothy Buck, Yo! podcast host Rob Hope, my brother Mark, and many others.

Undoubtedly, there is this movement of no-code happening right now. Folks like Ben Tossell of Makerpad are empowering so many makers to build MVPs, start startups, and ship them fast. Tools like Zapier, Carrd, Airtable, and so many third-party solutions make any technical barriers to entry lower than ever.

Did I go the no-code/low-code route? No.

But it’s worth noting, as Plink’s MVP does incorporate third-party solutions that made time to market much shorter. Throughout my years of making things, tools like Zapier and Gumroad have empowered me to be able iterate quicker, early on.

Without diving too deep into the most-developed part of Plink, the code and scripts - link routing functions, static pages solution, and more, know that Cloudflare Workers helped in launching the MVP. With Workers, you can write, deploy, and run server-side JavaScript “from the edge” in WebAssembly/service worker-like environment, serving everything from data centers close to the end-users. Workers and serverless environments, in general, are extremely efficient, performant, and fast.

Beyond the HTML/CSS/JS, Node.js, and Webpack codebase “from the edge” in Workers, making use of other Cloudflare solutions like their Workers key-value (KV) storage, CDN, and DNS management only made sense. I utilized other third-party solutions like DigitalOcean, GitHub, and more along-the-way.

Bootstrapping anything makes you constantly more aware of what paid subscriptions are actually needed. I keep overhead to a bare minimum, often opting to build things over buying. With an MVP though, using and buying into pre-made solutions early on can really help get the ball rolling sooner.

After I ended the private beta period, I received some press for Plink from the acclaimed podcasting industry newsletter and show, Podnews (thanks James), as well as from other industry publications - international press too: Polish podcast Radiogram and Spanish site Vía Podcast.

With the MVP now being public knowledge, I started some organic marketing pushes - here we go!

Plink v1 quickly proved to be a service that creators want and they started using right away.

Oh yeah, Plink is free, to boot.

My choice to build and launch a freemium offering, alongside paid upgrade options for custom, short links has worked in my favor. Without a doubt, the free domain links (versus custom domain links) have increased further product adoption.

The fact that I have customers that I’ve never met, folks outside of my network, alongside true champions of the service, and even affiliates is exciting. I’ve already established amazing, new relationships and partnerships with creators, consumers, and other podcast industry companies.

Plink podcast smart links example show page - the Newsworthy, Lore, and Yo podcasts

Has the MVP proven viable to spend more time on? Yes (and quite quickly)! Again, all of this really excites me.

Founding things always involves looking into the future, always staying a couple steps ahead.

Parallel to Tyler’s Storemapper story, I’ve been recognizing that I’m spending too much time on some things.

So, it’s time to polish things up and really move beyond MVP.

Shipping an MVP without user accounts, emails, and other functionality

Like Tyler shares about Storemapper’s initial MVP, Plink’s MVP lacks some standard SaaS functionality.

At its core I ensure Plink does what it says it will do on the marketing site.

Does it solve a problem and pain-point for creators? Yes. For consumers? Yes. Is it stable? Yes.

I have (quite cleverly) managed to couple things together. Yet it’s time to optimize things for scale - items like transactional emails, subscription management, and a customer-facing web application complete with signup, login, authentication, account and link management/customizations, a more robust internal API, and more need be developed.

As much as I want to only focus on product functionality and designing, developing, and shipping new features, there’s a sense of some MVP technical debt that I feel looming. And debts must always be paid.

SaaS subscription management and user signup was initially shipped with Gumroad recurring subscription drop-in solution. It’s time to move beyond this, though. Gumroad is great for information products/premium content and is a great product overall, but Plink needs an in-house (likely with Stripe) subscription management solution that’s more robust, putting control in my hands, and is more integrated/built into the product. Developing this will decrease per-order transaction fees, to boot.

A lot of this fragmentation can be attributed to my MacGyvered, third-party solutions setup. Some things should take a lot less time to accomplish and/or should be completely automated. So I’ll be focusing on developing solutions for this in moving beyond the MVP stage. Building solutions that ensure everything is more manageable and scalable going forward.

One way of looking at it: currently it’s a wood-glued, butt joint instead of a longer-lasting solution: a dovetail joint (haha - had to slip in a woodworking reference, see image for clarification).

Types of wood joints include dovetail, butt, mortise, and other joinery

Image from The Spruce Crafts (

Need for automation - Onboarding, support, and emails

In taking a broader, holistic view, it’s quite obvious I need to reduce manual tasks and automate things. Moving beyond MVP through improving onboarding, support, emails, developing a self-service webapp, and beyond.

More than anything, I strive to empower my users (and power-users), building product functionality so that they can create, update, or delete link data themselves. And I need to empower myself to spend less time on manual tasks.

Moving beyond MVP means ridding of any bottlenecks, for everyone involved.

Currently I answer requests and manage support conversations typically in scheduled batches, during specific times. Yet there needs to be less 1-on-1 and more evergreen documentation, more self-serve walk-throughs to get folks going. Though I love the 1-on-1 interactions, gaining so much from each interaction, it’s important to be honest and acknowledge that I’m spending way too much time manually doing things. And I know this can’t scale.

Custom, short link creation? Currently manual in the MVP. Any/all support? Manual. Onboarding emails? Manual.

It’s time to focus on consolidating answers that I find myself repeating, and turning those into documentation, alongside editing/re-writing copy for an onboarding flow, building out an automated onboarding email communication sequence, and generally tightening up the funnel.

Referring back to Tyler Tringas, this time citing content he wrote and shared on his website:

“Your answer to almost every question from early customers should be to just login as them do it for them. Then send them screenshots or a screencast of how you did it so they learn next time.” - Tyler Tringas, Do’s and Dont’s of Building an MVP Micro-SaaS

With Plink’s current backend architecture, I followed this principle (before even reading this from his website) and I did set myself up for success and for delighting customers early on. In ensuring that I have full control over customer’s backend setup and non-sensitive data, I can post, update, or delete values and link data for them. All of this without them having to do anything.

Need anything? Send a note to me directly via Drift chat on the marketing website.

Tyler goes on to say, “It’s becoming more common in some SaaS apps, but you cannot imagine how magic it seems to customers who email support asking “How do I do X” and you respond with, “Here’s how you do it, also I already did it for you.””.

Great advice and I’ve been doing this! But this won’t scale when having to do so for every paid customer. Tyler recognized this too and started building out automation into Storemapper.

What will scale is more automated functionalities, a self-service webapp, documentation, and a clear onboarding flow and series of onboarding emails. In providing a self-service solution, it empowers customers to make any changes they desire, very easily, intuitively, and quickly.

With Plink’s current state-of-the-product, it could be argued there isn’t even a need for an intensive onboarding flow, as there really aren’t many steps paid customers have to take before they can start using the product. And the free, non-custom/non-branded smart links are 100% ready-to-go right now, sans some premium functionalities.

So I set myself up for success with my free customers especially by writing clear copy and calls-to-action on the website, providing answers and the whats, whys, and hows. I have yet to feel any pressure of providing support to hundreds of free customers.

Yet for Plink’s paid customers there is a process after the custom, short links are (currently manually) created. And though links are ready to start working for them right away, it’s important to rid of any potential bottlenecks in the process, myself and my triaged 1-on-1 onboarding included.

Again, though I enjoy connecting with every single customer, it’s time to remove the need to individually onboard with the founder.

Moving beyond MVP means building functionality for customers to be off-to-the-races right away!

Optimize for scale now, ship new product features later

Focusing on automating things for the business now will set everything (and everyone) up for future success.

Core product features and functionality may be more exciting to build, as it’s something that everyone can then see being utilized by Plink’s users. Yet even shipping new features, especially if not planned and designed-out properly, has the potential to bring in more support requests, more bug fixes, and/or other manual work.

Slowing things down, running a calm and focused venture, while not reacting to every request is important to me.

For others bootstrapping projects and startups, it’s important to remember that even though starting development of ideas (and as entrepreneurs we’re always full of new ideas) is exciting, it’s more impactful to focus on setting our and our customer’s future selves up for continued success.

Optimize now, ship new features later.

Being a solo founder means taking on everything. Having had such a varied background of jobs, roles, projects, and clients lends to my confidence in myself in taking this on. Starting Plink has already been one hell of an adventure!

Thank you for reading this. Sharing my thoughts and writing articles like this provides just as much clarity and a reminder to myself as I hope it provides transparent insight and value to you and every reader.

If you’re interested in becoming an affiliate of Plink (35% commission on premium link subscription referrals), reach out to me personally on Twitter or subscribe to my newsletter and reply to email (this program will become automated and optimized for scale, too).

Thanks for reading and keep making things!

chevronLeft icon Previous Next chevronRight icon