Get Paid with Manny Medina

Dan Griggs has seen multiple platform shifts up close. From taking Sitecore through a private equity transformation to leading finance at Intercom, he’s spent his career navigating what happens when business models break and how to rebuild them.

Maria Colacurcio built Smartsheet into a Pacific Northwest giant. Now, as CEO of Syndio, she's betting the company on a pivot from SaaS to agentic AI. And she's not looking back. In this episode, Maria walks Manny through the launch of Syndi, an AI pay expert that transforms how companies make compensation decisions. Instead of annual pay equity audits that send CFOs scrambling for remediation bud...

This episode of Get Paid is a little different. Instead of bringing on a guest, Manny sits down with the engineering team at Paid to talk about what it’s actually like to build an AI agent company in year one. No slides, no polished narratives. Just the people building the product and deciding what actually ships. The team talks through what they’re working on day to day: how Paid handles billing...

Ariel Harmoko went from three-time national racing champion to Formula 3 driver to Cambridge's youngest ML researcher, all before turning 18. On this episode of Get Paid, he tells Manny how he built Artifact AI, an accounting automation platform that's taking on a $600B industry with a two-person team and a radically different approach to vertical AI. Ariel breaks down exactly how he landed his fi...

With over $100 million in recurring revenue, data productivity company Matillion was a thriving, established enterprise. Yet CEO Matthew Scullion spotted a fundamental threat on the horizon. In this episode of the GetPaid podcast, Matthew tells host Manny Medina why he pivoted Matillion’s focus, preemptively, before the rising tide of AI disrupted both their data engineer user base, and the produc...

In this episode of Get Paid, we speak to Dave Kellogg about the future of the software industry, with a specific focus on the shift from traditional SaaS models to AI and outcome-based pricing. Kellogg, a seasoned CEO, founder, Executive in Residence at Balderton Capital, and CFO Whisperer, with a background of leadership at Host Analytics (now Planful), MarkLogic, Salesforce.com, and Business Obj...

Manny Medina is joined by a guest who is crushing it in the world of sales technology: Nicolas Sharp, Co-founder and CEO of Attio, the AI-Native CRM. Attio's rapid growth with over 5,000 paying customers is a masterclass in strategic pivoting and catching a generational technology wave. Nicolas shares Attio's powerful growth story, which began with the difficult decision to abandon a niche CRM bui...

In a recent deep dive with Sequoia Capital partner Pat Grady, he shared surprising insights about what separates winning AI companies from the rest, and challenged conventional wisdom about AI moats, pricing models, and what investors truly value.

What happens when productivity shifts from labor to capital but tax systems don’t follow? In this episode, Paid’s Manny Medina and Arnon Shimoni sit down with Spencer Schneier and Sam Suechting from Commenda Technologies to unpack the findings from their landmark study on AI agent taxability. We reveal how the way you structure and price your AI agent can mean the difference between paying sales t...

Eric Simons spent seven years building a cloud IDE that millions loved but nobody would pay for. After investing a year into an enterprise product based on 2021 customer enthusiasm, he launched in 2023 to discover all that demand had evaporated. With the company at 18 months of runway and no path forward, Eric made the hardest call of his career: layoffs, followed by one final 90-day bet on a prod...

Jonathan Sanders watched two companies suffer through brutal ERP migrations that took 18 months, cost $200K+, and required constant consultant babysitting. At one point, a board literally told leadership not to migrate their ERP because it would be a massive waste of time with zero ROI. That's how broken the category is. So Jonathan built Light, a new type of smart finance platform that turns 18-m...

Manny and Raj sit down over a scotch to celebrate closing Paid's $21M seed round at a valuation between $100-200M, just 10 months after starting the company in an Airbnb with four people. This is the most candid conversation yet about what it actually takes to build a company at breakneck speed in the AI era. They unpack why Manny took a high valuation he's confident he can deliver on, how they cl...

Amjad Masad, CEO of Replit, just raised $250M at a $3B valuation and hit $150M ARR. But his most controversial take? The Silicon Valley model of scaling point solutions to IPO is dead. In this episode, Amjad reveals how Agent 3 works under the hood (spoiler: it's actually multiple agents arguing with each other), why their pricing model confuses consumers who think they're buying software when the...

In this episode, Manny sits down with Nick Holzherr, founder of GitLaw and former contestant on The Apprentice, to dive deep into the legal industry's impending transformation. Nick shares his journey from paying hundreds of thousands in legal fees for what he discovered were essentially template documents, to building a platform that automates 90% of legal work. He breaks down the shocking econom...

Madhavan Ramanujam stepped into the AI pricing conversation with a contrarian view: everyone is doing it wrong. As author of "Monetizing Innovation" and founding partner of 49 Palms Ventures, he's advised 250+ companies on pricing strategy. Now he's seeing founders leave millions on the table by using outdated SaaS playbooks for AI products. > "Your moat is monetization and GTM. Can you get pro...

John Sabino stepped into LivePerson as CEO facing a perfect storm: financial distress, harsh investor criticism, and a company that had "lost its way" trying to build the world's best LLM. Within weeks, major investors were telling him his strategy wouldn't work and that the company wasn't mentioned in critical industry reports. "You have to have the wherewithal and the courage to say, I'm not doi...

Ethan Ding (TextQL) tells Manny all the AI industry's dirty secrets. Companies bought 500 AI tools in 2024's spending frenzy - now procurement teams have total vendor bans and are cutting 250+ tools because nobody actually uses them. Meanwhile, 90% of people using AI tools like Harvey have no idea what ChatGPT or OpenAI even are, creating massive moats for first movers. The enterprise AI bubble is...

Join Manny and Rob Litterst, pricing expert and founder of PricingSaaS, as they dive deep into the seismic shift happening in SaaS pricing models. Rob reveals how traditional seat-based pricing is becoming obsolete as AI agents transform software delivery, with companies scrambling to figure out how to price outcomes rather than access. From Intercom's recent fundraise based entirely on their AI a...

When Silicon Valley drama gets juicier than reality TV, you know something is changing in tech. In this episode, Foundation Capital partners Ashu Garg and Jaya Gupta reveal why SaaS is dying, explaining that 9 out of 10 mid-sized SaaS companies are already seeing churn as AI-native startups eat them from below. They share wild stories from the frontlines, including a startup landing a $20M deal wi...

Blue AI Labs founder Maruthi Medisetty reveals how AI agents are transforming sales enablement by giving reps 60-75 minutes of practice time they'd never spend with managers. His provocative take: while AI can handle prospecting, no one's signing a $10,000 contract with a bot anytime soon. The real opportunity isn't replacing salespeople—it's turning your best reps into "super sellers" who can han...

Christopher O'Donnell, founder of Day.ai, joins the show to break down why building a new system of record for the AI era is both brutally hard and absolutely necessary. He reveals the preprocessing magic that makes their AI-powered CRM actually useful (spoiler: it's not just throwing database tables at an LLM), explains why the economics of AI should focus on customer value rather than minimizing...

Amos Bar-Joseph is proving that the traditional startup playbook is broken. As CEO of Swan AI, he's building what he calls an "autonomous business" - targeting $30 million in revenue with just three people by 2025. His company has been approached by over 50 VCs, not because they need funding, but because investors are starting to realize the venture capital model itself is changing when startups n...

When enterprise deals die at the finish line because of a 200-page security questionnaire, you know there's a billion-dollar problem hiding in plain sight. SecurityPal founder Pukar Hamal turned that pain into a service-as-software business that hit $2 million in revenue before building any actual software. The Pain That Creates Billion-Dollar Markets Picture this: you're about to close the deal t...

In this candid conversation, Jack Altman (Alt Capital) drops his guard and shares what it's really like being a VC - and Sam Altman's brother. From comparing investor-founder relationships to dating ("board members outlast executives") to revealing who the family IT guy was growing up, Jack brings refreshing honesty to startup investing. He breaks down why he started his podcast simply because "it...

In this episode, Aaron Levie, CEO of Box, delivers a masterclass on how AI is reshaping the enterprise software landscape. Drawing from his experience building Box through the cloud revolution, Levie provides a pragmatic take on whether we're in the "2005 or 2008 moment" of AI adoption. He argues that most companies are now past the naive ChatGPT-interface phase and have evolved to understand that...