About
Builder. Co-founder and CEO of Substack. Previously Co-founder and CTO of Kik.
Articles by Chris
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What about technical venture?
What about technical venture?
Or, how I learned to stop worrying and love Hack Week I was recently talking to a friend who’s an engineering lead at…
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Chris Best shared thisWelcome to Substack, Rishi Garg!Chris Best shared thisWhew - what a ride. Last week Underdog announced its acquisition by IG Group. Last spring I joined Underdog CEO Jeremy Levine as a first-time CFO and we began a big task: rewriting a $500M business from daily fantasy to prediction markets rails. It’s often felt like Everything Everywhere All At Once - but we did it. In one year we acquired a DCM/DCO, got clear on a few priorities, rebuilt all our business processes, data, and metrics to get focused and efficient, hired a leadership bench and restructured the team, and swung Ebitda from -12% in 2025 to +24% Ebitda in 1H 2026, culminating in the sale to IG. I’m still in awe of this team’s dedication and hard work to stand up an exchange in record time, with unwavering humor, focus and generosity. Next up is joining forces with IG Group, a partner with the resources and customer obsession to help Underdog achieve bigger things. I’m so grateful to Jeremy for his trust in me, and to the amazing Underdog team. I’ll always bleed Underdog yellow, and knowing we had the team in place and the support of IG leadership to tackle the next phase enabled me to pursue my own next chapter… ================================================= …Which is that I'm excited to share that I've joined Substack as CFO. I've admired Substack and CEO Chris Best for years. When my friend Mood Rowghani put us together, he knew the company’s mission would fit perfectly with my own. Substack brings together two things that really matter to me – democratizing entrepreneurship, and making important voices heard. These were two of the core promises of the Internet, which I’ve tried to help deliver in my time at Twitter and Square. To that end, Chris, Jairaj Sethi and the team are building something I deeply believe in: a platform that helps creators build independent livelihoods by creating thoughtful work people genuinely want to spend time with. In the process, they're also raising the quality of what we consume online. I’ve often had the experience of reading a Substack post, being deeply moved by it, and thinking, "There's no way I would have encountered this—and been changed by it—without Substack." I believe a world where Substack gets this right is an unequivocally better world, for creators and readers everywhere. I also love the particular challenge, chaos, team-building and joy of the growth stage. So I’m very grateful for the chance to join the Substack team in their next phase. Speaking of: we’re hiring! If building a new economic engine for culture sounds like your kind of mission, we'd love to hear from you. I'm especially looking for exceptional leaders in finance and operations who want to make an outsized impact alongside an extraordinary team: Head of Biz Ops: https://lnkd.in/gcv6hCsp Head of Strategic Finance (FP&A): https://lnkd.in/g4mJVrWs
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Chris Best shared thisThe hidden harm of AI writing | A clip from my Substack post, Mike Solana: "the slop within". Watch it here: https://lnkd.in/gqBJ-jta
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Chris Best shared thisWhen AI Writing Actually Helps | A clip from my Substack post, Mike Solana: "the slop within". Watch it here: https://lnkd.in/gqBJ-jta
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Chris Best shared thisHow Do We Preserve Human Thought? | A clip from my Substack post, Matt Taibbi: writing is "a personal religion". Watch it here: https://lnkd.in/gBxPjQAv
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Chris Best shared thisWhen AI Makes Arguments Unfair | A clip from my Substack post, Matt Taibbi: writing is "a personal religion". Watch it here: https://lnkd.in/gBxPjQAv
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Chris Best shared thisCreators Fear AI Backlash | A clip from my Substack post, Taylor Lorenz: "I'm a Pangram fan". Watch it here: https://lnkd.in/gGSPVvHm
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Chris Best shared thisWhy creators will gain from AI | A clip from my Substack post, Taylor Lorenz: "I'm a Pangram fan". Watch it here: https://lnkd.in/gGSPVvHm
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Chris Best reposted thisChris Best reposted thisToday, Substack is launching an AI detection feature, via an integration with Pangram. Going forward, you’ll be able to scan posts, replies, and comments on the Substack app to see an estimate of how much of it was written by a human, or with AI assistance. We care about this at Substack because it gets to the core of our mission to build an economic engine for culture. When content made by no one takes over parts of the internet that are supposed to be human, it pollutes the commons and makes it hard to discover and hear human voices. We’re also introducing tools for creators, including the ability to run Pangram on your drafts prior to publication, and to add a “How I make this” statement where you explain your process and set expectations for readers. Human perspective is the essential ingredient of culture, and this will be true no matter how powerful AI becomes. To learn more about AI detection on Substack and why we built it, read this blog post by CEO and cofounder Chris Best: https://lnkd.in/gM_5e9Dq
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Chris Best reposted thisChris Best reposted thisSubstack has one of the highest concentrations of skilled human writers on the internet, and we think that's something special. Starting now, users can request a Pangram check on any Substack post over 100 words directly on the platform.
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Thanks!
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Chris Best liked thisChris Best liked thisWhew - what a ride. Last week Underdog announced its acquisition by IG Group. Last spring I joined Underdog CEO Jeremy Levine as a first-time CFO and we began a big task: rewriting a $500M business from daily fantasy to prediction markets rails. It’s often felt like Everything Everywhere All At Once - but we did it. In one year we acquired a DCM/DCO, got clear on a few priorities, rebuilt all our business processes, data, and metrics to get focused and efficient, hired a leadership bench and restructured the team, and swung Ebitda from -12% in 2025 to +24% Ebitda in 1H 2026, culminating in the sale to IG. I’m still in awe of this team’s dedication and hard work to stand up an exchange in record time, with unwavering humor, focus and generosity. Next up is joining forces with IG Group, a partner with the resources and customer obsession to help Underdog achieve bigger things. I’m so grateful to Jeremy for his trust in me, and to the amazing Underdog team. I’ll always bleed Underdog yellow, and knowing we had the team in place and the support of IG leadership to tackle the next phase enabled me to pursue my own next chapter… ================================================= …Which is that I'm excited to share that I've joined Substack as CFO. I've admired Substack and CEO Chris Best for years. When my friend Mood Rowghani put us together, he knew the company’s mission would fit perfectly with my own. Substack brings together two things that really matter to me – democratizing entrepreneurship, and making important voices heard. These were two of the core promises of the Internet, which I’ve tried to help deliver in my time at Twitter and Square. To that end, Chris, Jairaj Sethi and the team are building something I deeply believe in: a platform that helps creators build independent livelihoods by creating thoughtful work people genuinely want to spend time with. In the process, they're also raising the quality of what we consume online. I’ve often had the experience of reading a Substack post, being deeply moved by it, and thinking, "There's no way I would have encountered this—and been changed by it—without Substack." I believe a world where Substack gets this right is an unequivocally better world, for creators and readers everywhere. I also love the particular challenge, chaos, team-building and joy of the growth stage. So I’m very grateful for the chance to join the Substack team in their next phase. Speaking of: we’re hiring! If building a new economic engine for culture sounds like your kind of mission, we'd love to hear from you. I'm especially looking for exceptional leaders in finance and operations who want to make an outsized impact alongside an extraordinary team: Head of Biz Ops: https://lnkd.in/gcv6hCsp Head of Strategic Finance (FP&A): https://lnkd.in/g4mJVrWs
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Chris Best liked thisChris Best liked thisToday, Substack is launching an AI detection feature, via an integration with Pangram. Going forward, you’ll be able to scan posts, replies, and comments on the Substack app to see an estimate of how much of it was written by a human, or with AI assistance. We care about this at Substack because it gets to the core of our mission to build an economic engine for culture. When content made by no one takes over parts of the internet that are supposed to be human, it pollutes the commons and makes it hard to discover and hear human voices. We’re also introducing tools for creators, including the ability to run Pangram on your drafts prior to publication, and to add a “How I make this” statement where you explain your process and set expectations for readers. Human perspective is the essential ingredient of culture, and this will be true no matter how powerful AI becomes. To learn more about AI detection on Substack and why we built it, read this blog post by CEO and cofounder Chris Best: https://lnkd.in/gM_5e9Dq
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