Summary & Insights
When a New York Times editor was forced to resign for publishing a sitting senator’s op-ed in the turbulent summer of 2020, it underscored a climate of fear where unorthodox ideas were being purged from mainstream platforms. In that moment, Substack emerged not just as a tool, but as a declared bastion for free speech, offering a lifeline to writers and thinkers who were being “summarily tossed” from their institutions. This foundational commitment to independence—paired with a simple economic model—became the catalyst for reimagining how culture gets made and funded on the internet.
At its core, Substack’s mission is to create a new economic engine for culture, shifting power from algorithmic, ad-driven platforms to individual creators. Co-founder Chris Best describes the platform’s origin as an attempt to solve the “cold start problem” for writing: making it dead simple to launch a paid newsletter was the minimal viable product for a much grander vision. This vision sees the direct, paid relationship between creator and audience as a form of creative freedom, allowing writers to bypass the need to “please the algorithm” and instead take creative risks supported by their subscribers’ trust. What began as “blogging with a business model” has evolved into a multi-format network encompassing podcasts and video, all centered on that principle of direct connection.
Looking ahead, Substack envisions a future where its network grows into a primary destination for meaningful content—a place where, as Best aspires, you look back on the time spent and think, “Damn, I’m glad I did that.” This stands in contrast to what he calls the “AI goon bot” future of addictive, algorithmically-generated slop. The company is betting that as media consumption fragments, there will be a growing, sustainable demand for work that helps audiences become “more the person they want or aspire to be.” This involves building tools and a network that supports not just solo writers but also “ambitious media founders” who are re-bundling into new kinds of publishing entities, fundamentally restructuring the media landscape around creator independence.
Surprising Insights
- The platform’s staunch free-speech stance was, in part, a fortunate business alignment. Best notes that while principled, Substack’s position lined up perfectly from a business perspective during the 2020 upheaval, as many of the world’s most interesting writers sought a new home.
- The “right to exit” is a core feature, not a flaw. Substack deliberately allows writers to easily export their subscriber lists, betting that this forces the platform to provide continuous, compelling value, which in turn fosters greater loyalty than a locked-in ecosystem.
- Substack’s original vision was “derangedly ambitious” and opposed paid-only content. The initial grandiose idea was to rebuild the internet’s cultural economy, but the team quickly pivoted from a strict “paid-only” rule after their first customer demonstrated the necessity of a free tier for audience growth.
- The need for a proprietary social network (Notes) emerged from a practical business problem. Creators were dependent on other platforms like Twitter for discovery, making them vulnerable to those networks’ changing priorities. Substack realized it needed to build its own “top of funnel” with different incentives.
- Algorithms and ads aren’t inherently evil—they’re tools to be aligned with better goals. Best argues the problem isn’t algorithms or advertising themselves, but their objective functions. A Substack algorithm, in theory, could serve to help users find content they deeply value, not just maximize engagement.
Practical Takeaways
- For creators: Prioritize building a direct, owned channel to your audience (like an email list). This provides the security and creative freedom to make work that doesn’t solely cater to an algorithmic feed’s demands.
- When starting a paid subscription service, offer a free tier. Use it as a top-of-funnel to demonstrate value and build an audience before asking for payment, as this conversion path is proven and effective.
- Consider serializing long-form projects. Instead of locking yourself away to write a book, publish chapters or ideas incrementally on a platform like Substack. This builds an audience and provides feedback, and the final product can still be compiled into a traditional book later.
- View your audience’s subscription as a “tap on the shoulder.” It’s permission to share your work directly, which allows you to occasionally bypass trend-based algorithms and share passion projects or experimental ideas with your core supporters.
- As a consumer, be intentional about your media diet. Actively seek out and pay for writers and creators who make you “a better person,” recognizing that your attention is a scarce resource and investing it well has long-term personal and cultural returns.
(00:00) – The Future of Jobs
(03:15) – Job growth over the last 80 years
(05:06) – The shelf-life of jobs
(09:11) – Education trends
(12:25) – The importance of learning the foundations
(17:18) – Regional access to education
(20:19) – How companies are hiring and looking at strategic priorities
(22:58) – The economic mobility and economic stability of degrees
(25:59) – Job and training trends at Grow with Google
(28:11) – Do companies train or hire for skills?
(29:23) – The future of the traditional degree
(31:10) – The employer and educator ecosystem
(35:36) – How to approach upskilling
In a world where technology is moving at an unprecedented pace, what will the jobs of the future look like?
Kai Roemmelt, CEO of the online learning platform Udacity, and Lisa Gevelber, a key figure at Google responsible for building the Grow with Google program, unpack the seismic changes reshaping the tech and education realms.
From disrupting hiring norms to redefining how we acquire degrees and engage globally, this episode poses the question: How can you skillfully navigate the challenges and seize the opportunities awaiting in this evolving landscape?
Resources:
Find Kai on LinkedIn: https://www.linkedin.com/in/kai-roemmelt
Find Lisa on LinkedIn: https://www.linkedin.com/in/lisagevelber
Learn more about Udacity: https://www.udacity.com
Learn more about Grow with Google: https://grow.google
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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.


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