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Get Paid with Manny Medina
Manny Medina, Arnon Shimoni
37 episodes
5 days ago

Welcome to the world of AI agents – where digital workers are reshaping everything from monetization strategies to GTM plays.


https://podcast.paid.ai

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All content for Get Paid with Manny Medina is the property of Manny Medina, Arnon Shimoni and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Welcome to the world of AI agents – where digital workers are reshaping everything from monetization strategies to GTM plays.


https://podcast.paid.ai

Show more...
Business
Technology
Episodes (20/37)
Get Paid with Manny Medina
S2E26: The $2.7B Agent Tax Crisis | Paid x Commenda Study
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 tax in 22 states or just 4 and how this “hidden arbitrage” could cost U.S. governments $2.7 billion a year starting 2025. This is bigger than it seems. We talk about the rise of the agent builder economy, the policy lag that mirrors e-commerce’s 25-year journey to standardization, and why outcome-based pricing and Private Letter Rulings might be your best defense. Whether you’re building, funding, or regulating AI, this episode offers a front-row seat to the fiscal rewiring of the digital economy and the blueprint for staying ahead of it.
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5 days ago
43 minutes 56 seconds

Get Paid with Manny Medina
S2E25: We had 90 days to ship or shut down | Eric Simons (Bolt)
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 product called Bolt. They shipped it with a single tweet on October 3rd, 2024. What happened next defied everything Eric learned in 15 years of building startups. Bolt added $60,000 of ARR on day one. Then $80,000 on day two. By week one, they hit $1 million. By month two, they went from $4 million to $20 million ARR, and the growth never stopped. The twist? Their customers weren't developers. Product managers at companies discovered they could ship in 60 seconds what used to take six business days through JIRA tickets. Eric breaks down the false demand trap that nearly killed the company, why distribution beats product when competitors have 5X your revenue, how a random tweet turned into a million dollar hackathon, and what it really takes to stay in the game when the odds say fold.
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1 week ago
54 minutes 8 seconds

Get Paid with Manny Medina
S2E24: NetSuite is where ERPs go to die. We're building the escape hatch | Jonathan Sanders (Light)
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-month implementations into one-day onboardings by letting finance teams configure systems with plain English policies instead of paying consultants to write scripts nobody understands. In this conversation, Jonathan reveals how working with OpenAI months before ChatGPT launched shaped Light's entire product philosophy around "student assistants" that work 24/7, why they deliberately avoided the traditional channel partner model that made legacy ERPs successful, and the brutal truth implementation consultants told him about why their incentives are completely misaligned with customers. He also explains why they almost went full outcome-based pricing but didn't, the new skill emerging in finance teams (hint: it's writing, not coding), and why the ERP category is so meaningless that it needs to die. If you've ever suffered through a NetSuite migration, this episode will feel like therapy.
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2 weeks ago
46 minutes 50 seconds

Get Paid with Manny Medina
S2E23: Building Paid: $31M Raised on Confidence, Not Fear (Manny Medina, Raj Dosanjh)
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 closed the round with a 60% working demo, and why Raj moved from India to London despite living like a king. Manny and Raj get honest about the cultural foundation we’ve built between seed and Series A, the arguing that nearly tore cofounders apart, and why they're done optimizing for the next round. They discuss forward deployment tactics borrowed from Palantir, why engineers don't need product managers, and the difference between playing for market share versus wallet share. Cofounder Manoj crashes the recording to share why he left retirement after two days of not being able to stop thinking about Paid's mission. This is the story of building with conviction, abundance mindset, and the belief that winning is the only metric that matters.
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3 weeks ago
1 hour 1 minute 27 seconds

Get Paid with Manny Medina
S2E22: "You're Not Buying Software, You're Hiring a $1K Employee" (Amjad Masad, Replit)
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 they're actually hiring a $1,000/year employee, and how Replit's own HR person built their org chart software in 3 days because vendors wanted tens of thousands for something that didn't fit. We dive deep into the future Amjad sees: fewer billionaires, way more millionaires building hyper-specific micro-SaaS for niches only they understand. He shares real stories of a VC CFO building software for other VC CFOs, freelancers doing Upwork arbitrage with Agent 3, and why Salesforce closing Slack's API is the exact wrong move. Plus, Amjad gets brutally honest about VCs leaking his numbers twice, why the management fee structure attracts short-term thinkers, and how Replit does seasonal intensity (12/12/7 during launches, sustainable hours the rest of the year) instead of the 996 grind. This is the playbook for surviving and thriving as traditional SaaS dies and the agent era begins.
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1 month ago
46 minutes 56 seconds

Get Paid with Manny Medina
S2E21: The $200K legal bills that made me automate law firms (Nick Holhzherr, GitLaw)
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 economics of law firms—where partners charge $2000/hour while paying juniors $100/hour to fill out standardized forms—and explains why this model is about to collapse entirely. The conversation takes a fascinating turn as Nick and Manny explore the broader implications of AI displacing entire professions. From the thousands of qualified junior lawyers who can't find work right now (but politicians don't see it yet), to the mind-bending tax revenue crisis coming when AI agents replace human workers, this episode reveals the systemic changes already happening beneath the surface. Nick also pulls back the curtain on his Apprentice experience, sharing the psychological manipulation tactics used by reality TV producers, and offers his "barbell strategy" for legal spending: automate the basics, hire only the absolute best commercial lawyers for complex deals.
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1 month ago
59 minutes 44 seconds

Get Paid with Manny Medina
S2E20: Price Before Product: The AI Monetization Playbook (Madhavan Ramanujam, 49Palms)
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 products in the hands of many people? Can you make it stick? And will they pay for the value?" His message is clear: the two-year coding head start you're banking on is worthless. In the AI era, your competitive advantage isn't technology - it's how you price and distribute it. The $50K to $500K Pricing Revelation Madhavan shares a story that captures everything wrong with AI pricing today. A founder came to him charging $50K for an AI agent that was creating tens of millions in value. The founder thought it was "reasonable" and helped close deals faster. "Put an option on the table. A $50,000 plus 10% of the outcomes that I generate or a $500,000 fixed fee." This simple choice changed everything. The conversation shifted from price to value measurement. Customers chose the $500K option and negotiated down to $400K - a 10X increase with the same sales velocity. "Which investor does not want that, right? That you could actually 10X your price and have the same sales velocity. Why wouldn't you do that?" Why most AI companies are pricing wrong The failing pattern Madhavan sees repeatedly: Companies tie pricing to costs rather than value. Founders add 20% margin to token costs and call it pricing. As costs fall, so does revenue, even though customer value remains constant. > "You just tied yourself to like a destiny that your pricing is going to keep coming down." The labor budget opportunity. AI agents tap into labor budgets that are 10X larger than IT budgets, yet founders still price like SaaS: > "200k to hire a salesperson and you charge $5,000 for a seat for a year. I mean like that doesn't make sense, right?" Underestimating AI's value capture potential. Traditional SaaS captures 10% of value created. AI with high autonomy and clear attribution can capture 25-50%: > "There is increased autonomy and there is increased attribution. And you can justify that." The Human + AI Pricing Formula Madhavan's framework for pricing AI that replaces human labor challenges conventional thinking: > "If your AI can operate as the best salesperson, and is available 24/7, why wouldn't you think about it that way?" His argument: It takes six months to hire someone, six months to train them. By the time they're productive, you've invested two years of salary. Your AI is productive on day one and works 24/7. Price accordingly - at or above human cost, not at 10% of it. The Partnership Imperative For established SaaS companies trying to add AI, Madhavan sees most getting stuck in seat-based pricing with no path to value attribution. His advice for companies like Slack: > "I think it has to be first principles thinking, can I build some agents that actually sit on top of Slack and can do some meaningful work that I can monetize on it separately." The key is finding the equivalent of Intercom's Fin.ai model - an agent that solves end-to-end workflows with clear value attribution. Pricing in the Age of AI Madhavan's framework for AI monetization starts before building: > "Price before product. Period." His approach:Have willingness-to-pay conversations before writing codeBuild only what people value enough to pay forChoose the right pricing archetype based on product characteristicsMove from cost-plus to value-based pricing as quickly as possibleLeadership Lessons from the Pricing Frontier Madhavan is juggling three major initiatives: running his fund (49 Palms), deploying capital, and launching his new book "Scaling Innovation." His thesis ties them together: > "Monetization is the key to winning in AI." His investment philosophy focuses on durable monetization rather than growth at all costs: > "You need to have a clear conviction that you can actually, at the end of the day, build a profitable growth business." Companies Mentioned49 Palms VenturesDelphiSierraIntercom (Fin.ai)ServiceNowSlackWorkdaySuperhumanGmailDocuSignZapierYC (Y Combinator)First Round CapitalNFXStanford See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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1 month ago
58 minutes 55 seconds

Get Paid with Manny Medina
S2E19: “VCs wanted us to build an LLM. We said no” | John Sabino (LivePerson)
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 doing that. I'm going to try this first." His response was to refocus on LivePerson's core strength - 30 years of orchestration expertise - while pioneering what became an industry standard: Bring Your Own LLM (BYOLLM). "Everybody thought I was nuts when we started with that. And now that is the industry buzzword. I'll be blunt. I think we started that." Why 95% (or maybe 60%?) of AI Pilots Fail The MIT study showing 95% of AI pilot failures validates what John has been saying all along, although we're not sure it's actually 95%. Maybe 60%.... "A use case is not a process. A use case is not a full customer journey. A use case is not a solution. That is what many people miss." The failing pattern:AI companies grab isolated use casesThey wow boardrooms with resolution ratesThey ignore orchestration, multi-channel needs, and escalation pathsCustomers get frustrated when complex issues can't be resolved The Human + AI Formula John's framework for CEOs navigating AI transformation focuses on strategic augmentation rather than wholesale replacement: "Don't fire all your humans. Those are the people that should handle complex cases where the package went to the wrong location, where the payment was wrong." The opportunity lies in creating premium tiers of service. High-net-worth banking customers and serious gamers will pay for white-glove human support. Meanwhile, automate the "high caloric, low value tasks" that make up 45% or more of inquiries. The Partnership Imperative Drawing from his GE Digital experience, John believes survival in the AI era requires acknowledging what you can't build: "Partnerships matter. Unless you're one of the big three, you're just not going to have the resources to build everything for everybody." LivePerson's partnership strategy today includes multiple LLM providers - through a BYOLLM approach. For John, this was validated when DeepSeek emerged "out of left field" and could immediately integrate with LivePerson's platform. Pricing in the Age of AI John's approach to monetizing new AI capabilities rejects the "fail fast and free" mentality: "I don't believe in doing a pilot for nothing because if it's free, it doesn't have value or a basis to establish value." His framework:Start with 3-4 early access customersCharge professional services fees initiallyUnderstand value creation through real usageThen determine pricing model (seats, volume, or outcomes)The goal is outcome-based pricing, but you need data first: "In order to price any metric or unit that you're going to use to establish value, you need to know the outcome that you're driving." Leadership lessons from crisis John's military background (Ranger School, Airborne) shaped his crisis leadership philosophy: "You want people in your organization that have the grit, that know how to take the objective with less. If they fail, they dust themselves off and say 'next one, let's go.'" His framework for CEO decision-making:Always consider shareholder valueAnswer to your customersTake care of employeesMake financially responsible decisionsNever shy away from tough choicesThe Gartner Magic Quadrant Journey Responding to investor criticism about not being in key reports, LivePerson made a concerted effort to improve their position. The achievement wasn't just about targeting the report: "It needs to be your technology speaking for you. It needs to be your customers speaking for you. And that's what that Gartner report represents." Companies mentionedLivePersonAmazon ConnectAvayaGoogle RCSWhatsAppDeepSeekIntercomDecagonMicrosoftSalesforceProcter & Gamble (P&G)VMwareGE Digital See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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1 month ago
50 minutes 32 seconds

Get Paid with Manny Medina
S2E18: ChatGPT is going to sell you therapy | Ethan Ding (TextQL)
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 bursting with 50% of initiatives already dead, but nobody wants to admit their AI strategy failed. OpenAI's aggressive pricing on GPT-5 reveals their endgame: becoming a billion-user ad platform where ChatGPT recommends therapists, books appointments, and charges your credit card. Ethan's contrarian playbook? Don't innovate on UI (every attempt has been "a horrible idea"), just copy ChatGPT's interface and put all innovation into branding and distribution. Meanwhile, everyone fights over $10B exits and Ethan is going after AWS with a "flip coins at 51% odds" strategy because only trillion-dollar markets matter. The punchline: data science is an infinite arms race where Blackstone analyzes weekly, Cerberus counters daily, then someone goes hourly - creating exponential demand that rewards volume over margins.
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2 months ago
41 minutes 46 seconds

Get Paid with Manny Medina
S2E17: SaaS Revenue Bloodbath Is Coming | Rob Litterst (PricingSaaS)
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 agent growth to the emergence of "ergonomic pricing" models that blend licenses with outcomes, this conversation unpacks the most pressing challenge facing every SaaS company today. The discussion ventures into unexpected territory, exploring how companies are using AI to access software through Claude rather than traditional interfaces, the rise of "vibe marketing" in a stagnant marketing landscape, and Rob's provocative prediction of a "revenue bloodbath" in SaaS as teams shrink and AI-native companies capture market share. Rob shares candid insights from his new venture helping companies navigate this transition, including the surprising revelation that even traditional "mom and pop" SaaS companies are now asking about agent pricing - signaling that this transformation is hitting mainstream faster than anyone expected.
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2 months ago
38 minutes 58 seconds

Get Paid with Manny Medina
S2E16: AI is better than Love Island | Ashu Garg and Jaya Gupta (Foundation Capital)
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 with their first customer and the soap opera unfolding at Cursor - where the company collecting 100% of your infrastructure costs is simultaneously building your competitor. As Manny puts it, "This is better than Love Island." The conversation gets spicier as Ashu admits he won't even take meetings with companies that have revenue ("I want big ideas, not messy revenues") and predicts that neither OpenAI nor Anthropic will be the ultimate winners despite their massive valuations. Jaya reveals how young founders are outpacing third-time unicorn builders because in AI, everyone's learning curve started at the same time - experience just became a liability. They close with a radical vision: forget building another feature company. The future belongs to companies deploying 500 AI agents to replace what used to require 500 different SaaS tools. For founders navigating this chaos, their advice is brutal but simple: think bigger, move faster, and remember that most of what worked in SaaS won't work in AI.
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2 months ago
42 minutes 4 seconds

Get Paid with Manny Medina
S2E15: Will Bots Buy From Bots at $10K? | Maruthi Medisetty (Blue AI)
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 handle 5x their current quota. From eliminating 50-hour workweeks for enablement teams to challenging the entire learning management system stack, Maruthi breaks down why capturing just 10% of delivered value is the sweet spot for AI pricing. He shares candid insights on attribution challenges, the psychology of B2B purchasing decisions, and why companies still pay McKinsey millions just to have someone to blame. This episode cuts through the AI hype to reveal what actually works when augmenting human sales teams.
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2 months ago
42 minutes 57 seconds

Get Paid with Manny Medina
S2E14: Infinite markets: We don't optimize for COGS | Christopher O’Donnell (Day.ai)
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 costs, and shares his contrarian take on why transparency trumps features every time. From navigating the technical nightmare of Gmail APIs to philosophical insights about the universe conspiring in our favor, Christopher offers a rare glimpse into what it really takes to compete in the infinite CRM market. Whether you're building AI products, rethinking your data strategy, or just trying to survive the entrepreneurial journey, this conversation delivers actionable insights wrapped in refreshingly honest storytelling about the realities of deep tech entrepreneurship.
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3 months ago
40 minutes 12 seconds

Get Paid with Manny Medina
S2E13: The Death of Traditional Startup Scaling | Amos Bar-Joseph (Swan)
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 no longer need massive capital to scale. The secret isn't replacing humans with AI - it's reimagining how humans and AI collaborate. Amos breaks down his three-function business model: revenue creators, product creators, and agent creators. Each person manages armies of AI agents designed not to automate processes, but to amplify human potential. The result is a fundamental shift from scaling with headcount to scaling with intelligence, creating unfair advantages that traditional enterprises can't replicate without rebuilding from scratch.
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3 months ago
47 minutes 59 seconds

Get Paid with Manny Medina
S2E12: Getting Customers to Pay Before You Code | Pukar Hamal (SecurityPal AI)
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 that changes your company's trajectory. The champagne is ready. Then boom - instead of DocuSign, you get 200 pages of security questionnaires: "We were like ready to pop champagne bottles. And so, you know, we got hit with this, what is this? It's like hieroglyphics, you know, like, do I have barbed wire around my data center?" Pukar's insight was if startups can't afford armies of lawyers to fill out paperwork, only big companies with resources will win enterprise deals: "My like fundamental realization was if companies have to fill out a bunch of paperwork before they close a deal and they don't have the resources to do that, then all the big companies are gonna win, because they do have the resources." Service-as-Software: The $2M Validation Hack Instead of building software first, Pukar started with pure service. A prospect asked if he could just fill out their security questionnaire: "And I hadn't even incorporated the company. And the person was like, send me an invoice. I'm like, what is an invoice? I went on like Stripe Atlas and incorporated the company. So I had a company that wanted an invoice before I even incorporated it." While working a consulting day job, he'd stay up all night filling out compliance forms: "So at night I'd fill out these questionnaires and I had a customer send me a question. I'll be like, I need this back tomorrow morning, East coast time. Stay up all night. I fill it out. I send it at 3 a.m. They got the deal done." The magic was in the positioning - customers didn't want software, they wanted outcomes: "Yeah, so in the beginning, we didn't even have software. I was building this off of Google Sheets and Airtable dashboards. People would be like, when are we going to get a login? I was like, why do you need to log in? You have a form that needs to be filled out, and you want it filled out." This approach generated nearly $2 million before any real software: "We were well over a million, almost a two million before we even like built any software." Complexity-Based Pricing Beats Per-Seat Models SecurityPal charges based on complexity rather than user seats - questionnaire difficulty, product lines, regions, and SLA requirements: "I fundamentally anchored our pricing based on complexity. It's like how complex is your problem as it relates to security reviews and security questionnaires?" Want same-day turnaround? That costs more: "So I would say like the vectors for pricing for us are quantity of work. And then the SLA, right? So do you want it done same day? Or are you okay with like three, five days?" His pricing philosophy is refreshingly practical: "Biggest piece of advice from pricing standpoint that I can give anybody is like your pricing is going to change, forget about perfecting it today." AI Agents Won't Replace Premium Service While the industry rushes toward AI automation, Pukar sees the premium market wanting hyper-personalized service: "My friends that have it told me, you call them, you get a real person and like they're hell bent on figuring out how to help you solve your problem. And like that premium experience, it's like hard to really like get that through like AI agents." The Bootstrap Mentality That Scales Pukar's advice cuts through Silicon Valley hype: "If you really believe in something, you're really passionate about it, and you want a certain version of the world to be created, and you will literally eat ramen and work out of the corner of your apartment, you don't need to raise capital. You just need one customer to believe in you." The key insight: "You don't need to deliver for that customer, the perfect version of the product, you just need to deliver value. And you need to get that customer to say that you've delivered them value. You got to get paid." His brutal reality check: "But by the way, if you're not getting paid, it doesn't exist. It's just basically feel good conversations that are happening." Companies Mentioned: SecurityPalTalentBinTeamableDriftAirtableFigmaVantaCraft VenturesStripe Atlas See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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3 months ago
34 minutes 34 seconds

Get Paid with Manny Medina
S2E11: AI Agents Will Eat Everything | Jack Altman (Alt Capital)
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 would be fun," admits he's "lower disciplined," and explains his people-first investment philosophy: "I'm not waiting for the pitch, I'm waiting for people." Jack also tackles the big AI questions everyone's asking. He predicts agents will be everywhere but argues the space won't be winner-take-all, using a brilliant payroll industry analogy to explain why multiple AI companies can thrive simultaneously. Plus his brutally honest take on market sizing ("we all suck at trying to guess how big a market's gonna actually be") and why he's deliberately keeping his fund small while others chase billions. Whether you're building a startup or just curious about Silicon Valley family dynamics, this episode delivers insights you won't hear anywhere else.
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3 months ago
45 minutes 23 seconds

Get Paid with Manny Medina
S2E10: Why AI Won't Kill Salesforce | Aaron Levie (Box)
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 the real value lies in agentic workflows running in the background. The conversation tackles the hottest debates in SaaS: Is the seat-based pricing model dead? Will AI agents replace traditional software platforms? Levie's contrarian take - that agents will enhance rather than replace existing systems - challenges the prevailing wisdom about AI disruption. The discussion gets spicy when Levie warns that tech leaders using AI as a scapegoat for layoffs could trigger regulatory backlash from politicians like Bernie Sanders, potentially stifling innovation. He advocates for companies to focus on output expansion rather than cost-cutting, sharing real examples from Box where AI implementation led to hiring more engineers, not fewer. The episode explores complex architectural decisions around AI pricing models, the future of systems of record, and why deterministic data should never be owned by non-deterministic AI systems. Levie's bold prediction that legacy giants like Salesforce and Oracle will coexist with AI rather than be disrupted makes for compelling listening, especially when he admits he might be "laughably wrong" in 10 years.
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3 months ago
48 minutes 39 seconds

Get Paid with Manny Medina
S2E9: The BPO Boss: Humans Are Going Premium | Bryce Maddock (TaskUs)
We sit with Bryce Maddock, CEO of TaskUs, a $1B+ revenue BPO managing 60,000 employees across 13 countries. In this brutally honest conversation, Maddock exposes the gap between AI automation claims and reality, revealing how companies publicly boast "80% automation" while privately maintaining the same headcount. He shares TaskUs's controversial strategy of intentionally losing money—cutting prices from $2 to $1 per contact—to accelerate AI deployment and transition from hourly billing to outcome-based pricing. Maddock doesn't sugarcoat the future: "I don't know that all 60,000 are going to make it through the journey. Anyone who says differently isn't being truthful." He explains how AI is creating unexpected challenges, like angry customers escalating to humans after AI failures, and reveals the board-level pressure driving rushed AI decisions based on misleading headlines. From his bold prediction that he'll either "look like a genius or complete fool" to his insights on how humans become "premium features," this episode delivers unprecedented transparency about leading through the AI revolution.
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4 months ago
45 minutes 41 seconds

Get Paid with Manny Medina
S2E8: "You almost have to erase everything you learned in the 2010s" | Kellan Carter (FUSE)
FUSE VC General Partner Kellan Carter reveals why the 2010s SaaS playbook is dead and outcome-based pricing is the future. From a 24-year-old building AI for 911 dispatching to the secret board-level panic over revenue quality, Kellan shares unfiltered insights on what's actually working in AI investments. Topics include voice AI competition, BPO disruption, professional services transformation, and why founder quality now matters more than growth metrics. Recorded at the Paid studio.
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4 months ago
44 minutes 14 seconds

Get Paid with Manny Medina
S2E7: Will AI Agents Kill Customer Service Jobs? | Alexander Matthey (Parloa)
In this episode, Alexander Matthey, CTO and co-founder of Parloa, shares his vision for how AI agents will transform customer service. Drawing from his experience at Adyen and previous startups, Matthey explains why he believes people will actually want to talk to customer service in the future. He discusses how AI agents will enable 24/7 support without language barriers or wait times, while human agents will shift to handling more complex, specialized cases that require nuanced problem-solving. Matthey also addresses critical industry questions about implementation challenges, enterprise adoption, and the fate of Business Process Outsourcers (BPOs). He reveals why building modular AI systems from day one is essential for enterprise success, how engineering productivity will change with AI coding tools, and why the industry needs to shift from time-based to value-based pricing models. The conversation covers practical insights on US market expansion, the balance between hype and reality in AI deployment, and why execution remains the key differentiator in a fast-moving market where everyone claims to have the same capabilities.
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4 months ago
35 minutes 10 seconds

Get Paid with Manny Medina

Welcome to the world of AI agents – where digital workers are reshaping everything from monetization strategies to GTM plays.


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