Freemius Launches Season 2 With Rand Fishkin as First Guest

7 min readFeb 27, 2024

It’s official — we’ve launched Season 2 and we’re thrilled to share what’s in store 🥳 Season 2 builds on the lessons learned from the previous season and swings for the fences with a ‘star-powered’ guestlist of world-class business leaders and episodes that pack a punch by diving deeper into software entrepreneurship.

Speaking of star power, take a look at who’s joined us for the just-launched Episode 1. We’re excited to welcome Rand Fishkin as our first guest:

Before we get into the rest of the lineup and the topics we’re tackling in Season 2, let’s explain why we’re continuing to invest in

What Is the Purpose of the Podcast and Who Is It for? is a value-first podcast for bootstrappers, indie developers, and software product makers to kick their heels up, don their headphones, and be inspired/entertained by entrepreneurial experts with a range of skill sets.

Our mission is to stimulate meaningful conversations that deliver engaging, enlightening insights and actionable advice to help software creators launch and grow their businesses. Makers are more than just their creations, and by delving into their varied life stories, we aim to uncover unexpected connections and innovative approaches to software product creation.

Our ultimate why is to democratize knowledge and allow everyone to learn from the best in their respective fields. In this way, we’re giving back to the software community with practical insights that can be applied to any digital product business and used by any software creator.

Revealing Season 2’s Guestlist and Episode Topics

Before we reveal the full guestlist and episode topics (yes, we know we’re teasing!), here’s what Freemius founder and CEO Vova Feldman has to say about the scope of Season 2:

Season 2 of @pluginfm is coming next week 🎙️🚀

We got an amazing lineup of world-class leaders 🧑‍✈️

So proud of the team and outcome 📦

Let’s go!

- Vova Feldman 🥟 Attending #WCAsia (@vovafeldman) February 23, 2024

As Vova mentioned, Season 2 will tackle a range of topics, such as overcoming the challenges of remote-first companies, succeeding at building in public, and more. While Season 1 was essentially ‘learning as we go’, the experience allowed us to produce Season 2 more stably and leverage previous contacts to expand our reach and bring in some heavy hitters!

Without further ado, let’s reveal Season 2’s guests and the topics they’ll explore:

Educational Marketing, AI, and SEO in 2024: Rand Fishkin Unleashes the Strategies You Need!

Rand Fishkin

Known for his entrepreneurial flair and as the co-founder of Moz and SparkToro, Rand Fishkin has propelled his ventures to impressive heights, with Moz boasting a $45 million/year success story. In our launch episode, Rand shares the educational marketing, SEO, and AI strategies entrepreneurs need to master in 2024. He touches on his own experience from starting a blog to building a product to running a company, as well as how long you should invest in SEO (if you should invest in it at all).

Matt Mullenweg on the Challenges and Successes of Building a Remote-First Company

Matt Mullenweg

One of the most prominent figures in the tech world and a bonafide pioneer of remote working, co-founder of WordPress and CEO of Automattic, Matt Mullenweg, knows firsthand the challenges of building a successful remote-first company. In this episode, Matt draws from his deep experience and shares his insights/advice on how founders can navigate the pitfalls of global distribution to build a winning distributed company.

Love, Marriage & Bootstrapping: Kim & Jason Coleman on Building a Software Company With Your Spouse

Kim and Jason Coleman

As a married couple with two kids, Kim and Jason Coleman have built a successful company and several software products together. Because their software journey goes far deeper than a professional partnership, they bring a unique perspective to the world of bootstrapping. Kim and Jason share how they navigate personal and professional challenges, from compromising (or not) on hard decisions to facilitating a healthy work environment that encourages team buy-in, all while maintaining a harmonious marriage.

David vs. Goliath: Justin Ferriman on How Underdog Entrepreneurs Can Overpower Bigger Software Competitors

Justin Ferriman

Justin Ferriman grew LearnDash from a simple blog to one of the leading solutions in the LMS space through aggressive marketing and ‘guerilla’ tactics that took on bigger competitors. Justin sold LearnDash at 32% YoY growth with 76% profit margins and then moved on to elite business coaching. His savvy business instincts, constant content creation, and confident competitiveness have led to success — we’ll be unpacking the specific strategies and tactics he used to take on bigger competitors with more resources and still come out on top.

Promotion Through Education: How Courses Can Help You Grow Your Software Business

Chris Badgett

Chris Badgett is a passionate advocate for democratizing online education, and as the non-technical founder and CEO of LifterLMS, he offers a unique business perspective on the field of eLearning. In this episode, we pick his brain and delve into the transformative potential of educational marketing through course creation, specifically for software product makers.

Freemium to Premium: Amir Helzer Reveals Key Lessons from WPML’s Business Model Transformation

Amir Helzer

Amir Helzer is the founder of OnTheGoSystems, the company behind WPML, a leading multilingual plugin that’s used by over a million websites. WPML was originally a freemium plugin, but due to unfortunate (maybe even controversial?) circumstances, Amir and his team decided to only make a premium product. Amir shares the challenges and dynamics of taking a product from freemium to premium successfully in this riveting episode.

Bootstrapping In the Spotlight: Arvid Kahl on How Software Creators Can Perfect the Art of Building in Public

Arvid Kahl

Embodying value-driven entrepreneurship, Arvid Kahl has a career that spans co-founding, bootstrapping, and selling a business (FeedBack Panda) all the way to extensive writing and podcast hosting on ‘ The Bootstrapped Founder ‘. He’s a passionate believer in the power of sharing the journey with the ‘build in public’ movement. Arvid shares his insights on balancing transparency with business strategy while exploring the positive impact that building in public can have on software product makers’ lives and careers.

Optimizing Your Software Pricing Page for Results with Vova Feldman

Vova Feldman

Freemius founder and CEO Vova Feldman is a serial entrepreneur and a full-stack developer who is passionate about helping software developers make a living pursuing their passions. In 2011 and while he was doing enterprise sales, Vova learned how important it is to tailor a price to a buyer and how psychology can make a meaningful impact on the sales process. Vova unveils the most common mistakes and shares strategies that turn visitors into customers and optimizes your pricing page for results that resonate with your audience.

From SEO Maestro to Investing Magician: Joost de Valk on the Power of Raising Funds In Bootstrapping Ecosystems

Joost de Valk

Joost de Valk shaped the landscape of WordPress SEO by bootstrapping his company Yoast into a 140-person enterprise with over 12 million websites using their flagship product. In 2021, Joost and his wife Marieke van de Rakt exited Yoast and entered the world of investing with Emilia Capital. This episode explores the power of raising funds in bootstrapping ecosystems, touching on how to raise capital from funders like Joost and what you can expect to raise from an early funding round.

The Art of Scaling: Unlocking the Secrets to Business Growth with WP Engine’s Jason Cohen

Jason Cohen

WP Engine founder Jason Cohen has a wealth of knowledge when it comes to growing software businesses and organizations. In the last episode of Season 2, Jason explores the mindset required as a founder, the challenges faced, the exhilarating moments, and the struggles encountered along the way, shedding light on what it takes to navigate the complexities of scaling a business.

We Can’t Wait to Hear Your Thoughts on Season 2!

It’s been a long journey to get to this point and we are incredibly proud of what we’ve accomplished with Season 2.

If we’re honest, it was meant to have launched at the end of 2023, but as any maker worth their salt knows: plans change, you’ve got to roll with the punches, and flexibility needs to become the name of the game 😉

As it turns out, however, the delay was a gift! It has helped us produce something that stands head and shoulders above what we’ve done before. We are thrilled and excited to embark on this journey with you, and we can’t wait to hear what you think of the episodes and the season as a whole!

Reach out to us on social media and share your thoughts 🤠

Originally published on the Freemius blog on February 27, 2024.




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