How Smirk Health runs GTM through an agentic AI layer | Felix W. Ortiz III

Estuary is a right-time data company building infrastructure that delivers both streaming and batch capabilities — so companies can move and transform data at whatever latency their use case demands, from millisecond-level real-time pipelines to traditional batch analytics. With a growing enterprise customer base and NRR at 150%, Estuary is expanding beyond its PLG roots to go upmarket. In a recent episode of BUILDERS, we sat down with David Yaffe, Co-Founder and CEO of Estuary, to learn how the company was built from internal tooling his previous team couldn't source externally, why they deliberately priced to leave money on the table, and how AI is collapsing the historical divide between the two buyer personas that defined the data infrastructure market for a decade.Topics Discussed:How Estuary was built from internal infrastructure David's team couldn't find anywhere elseWhy the early GTM deliberately led with a use case that undervalued the product — and why that was the right callHow Estuary hit 150% NRR without a CSM teamThe pricing decision to actively lower prices to unlock larger use casesHow AI has reshaped Estuary's ICP by removing the divide between software engineers and data engineersHow to identify tire-kickers early and stop wasting cycles on deals that won't closeGTM Lessons For B2B Founders:Lead with the most repeatable sale, not the most impressive one. Estuary's early motion focused entirely on the analytics use case — moving data from source to warehouse. David was explicit that this undersold the platform: it's a batch workflow that didn't touch Estuary's real technical differentiation in streaming. He pursued it anyway because it was legible, budgeted, and repeatable. The modern data stack wave meant buyers already had line items for it. For founders with technically deep products, the instinct to lead with full capability is usually wrong early. Find the use case that maps to an existing budget category and build volume there first.Your first buyer doesn't need to be your best buyer — design for internal spread. Estuary routinely lands with a marketing or analytics team that has zero interest in streaming or low-latency data. What converts those small deals into meaningful revenue is what happens after: that team hears about an internal use case that does require real-time data, and they become the internal evangelist. David described this as a core part of how NRR compounds. The implication: make sure your product is legible enough that a non-technical champion can describe its value to a team they've never worked with.Price to accelerate adoption, not to extract maximum value upfront. Estuary has deliberately kept prices below what the market might bear, and has lowered prices at least once specifically to stimulate larger use cases — accepting a short-term revenue hit to do it. David's reasoning: customers who feel they're getting a fair deal don't build internal replacements or evaluate alternatives. At scale, he described watching usage hit a ceiling and wanting to get ahead of the moment when a customer thinks the platform is too expensive. Founders building usage-based or expansion-driven businesses should ask whether their pricing is a growth accelerant or a growth ceiling.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Hi Auto is on a mission to automate the drive-thru for quick service restaurants using voice AI. After pivoting twice — first from automotive voice AI, then from contactless kiosks — the team found their real wedge when Burger King Europe told them that replacing the drive-thru order taker, not adding another interface to a kiosk, was the problem worth solving. In a recent episode of BUILDERS, we sat down with Roy Baharav, CEO and Co-Founder of Hi Auto, to learn how they built a true vertical AI solution from scratch, landed Checkers and Rally's as their first brand partner, and scaled to work with some of the largest QSR chains in the world.Topics Discussed:How Hi Auto pivoted twice before landing on the drive-thru as the right wedgeWhy Checkers and Rally's took the bet during COVID and what that first deployment looked likeThe real reason QSR operators delay — and why it has nothing to do with ROI mathHow Hi Auto's positioning evolved from accuracy and completion rate to ROI, stability, and franchise operabilityThe dual labor pressure facing QSR: 100-300% annual employee turnover plus rising minimum wagesWhy the primary value of drive-thru AI is consistency and upsell capture, not headcount reductionWhat makes restaurant tech one of the hardest GTM motions in B2BHow regulatory tailwinds like California's $20 minimum wage are compressing the adoption timelineGTM Lessons For B2B Founders:Let customer rejection redirect the product, not just the pitch. Hi Auto's drive-thru pivot didn't come from internal strategy — it came from Burger King Europe rejecting their contactless kiosk prototype and telling them why. The kiosk failed because it added a voice interface on top of something that already replaced labor. The drive-thru worked because it replaced an actual person. Roy's team took that signal back to their investors, told them two ideas were wrong, and pivoted the company. For founders selling into industries they don't operate in, early pilots should be structured as listening exercises, not validation exercises. The buyer's unsolicited redirect is often the product insight worth more than everything else in the meeting.The right sales frame is replacement, not augmentation. Hi Auto's kiosk prototype stalled because it layered capability onto an existing interface without eliminating any cost. The drive-thru worked because it performed a discrete, time-accountable labor function — order taking — that could be directly measured against headcount. Roy noted that even the labor story is more nuanced than straight reduction: automating order taking frees staff to expedite orders, which shortens line times and increases throughput. Founders pitching AI or automation into cost-pressured verticals need to answer one question before anything else: what specific, measurable cost or function does this replace? Augmentation is a feature conversation. Replacement is a budget conversation.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Two months before this conversation, The Biological Computing Co (TBC) was still in stealth. Three years of building, rebranding, and accumulating experimental data — all before showing the world a single thing. In this episode of BUILDERS, we sat down with Alexander Ksendzovsky, Co-Founder and CEO of TBC, to hear how a neurosurgeon-scientist turned a 20-year research obsession into a commercial AI optimization company. TBC grows living neuron cultures, connects them via electrodes, and derives software tools from the biology's computation — currently applied to video generation model optimization, with language models and world models on the roadmap. The ICP they're selling to today is not the one they envisioned at founding. The name they operate under is a deliberate category ownership move. And the stealth-to-launch decision was made entirely on one criterion: enough data to show the world, not just tell it.Topics Discussed:How TBC uses living neuron cultures and electrode arrays to derive optimization techniques for AI video generation models that silicon-based approaches can't replicate Why TBC's current ICP — video gen model companies that have exhausted standard optimization techniques — is not the customer they anticipated when they founded the company TBC's two-track marketing framework: awareness and credibility, and why sequencing them correctly matters for deep-tech GTM The stealth-to-launch decision: the specific data threshold that triggered TBC's emergence after three years, and why they would not have come out earlier How investor pitch feedback — not customer feedback — drove TBC's rebrand from academic positioning to product-forward identity Category creation in a nascent field: TBC's approach to building the ecosystem rather than fighting for definitional control How TBC structures hiring and team cadence to keep exploratory research culture from blocking commercialization GTM Lessons For B2B Founders:Time your launch to proof, not momentum. TBC spent three years in stealth before going public — not because they feared competitors, but because they needed enough experimental data to generate belief rather than just curiosity. Alex's framing: "If we had done this two years ago, we had some interesting experiments, but people would think it's just research at that point. We really needed people to see that we're building real tools, they're productized and they're ready for production now." For deep-tech founders, the stealth exit decision isn't about market timing — it's about whether your evidence base crosses the threshold from interesting to credible.Investor pitch feedback is your earliest positioning stress test. TBC's rebrand wasn't triggered by customer research — it was triggered by investors consistently not understanding what they were building. Both founders came from academic neuroscience and were unconsciously pitching in that register. Alex: "We learned very early on through pitching to investors that the way we were positioning it was way too academic. We had to beat that out of ourselves." For pre-revenue founders, if investors with context can't quickly grasp your value proposition, buyers with less context won't either. Fix the positioning before you scale the outreach.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Edmund spent years as Chief Data Officer at HCA Healthcare — 200 hospitals across America — watching a parade of vendors pitch solutions to problems that didn't exist in his environment. He saw the pattern clearly: founders who had never been inside a complex healthcare system, selling point capabilities with no understanding of how clinical workflows actually interconnect. When the AI moment arrived, he left with a PhD in AI and enough operational scar tissue to know exactly what not to build.In this episode of BUILDERS, Edmund Jackson, CEO of UnityAI, breaks down why healthcare AI keeps producing expensive failures, how UnityAI found its ICP after abandoning health systems entirely, and the specific go-to-market sequencing that lets them sell finished solutions into slow-moving enterprise accounts without dying in a co-development process.Topics Discussed:What vendors consistently get wrong pitching into complex healthcare environments — and why ignorance of operational detail is the core failureThe three structural reasons clinical scheduling is far harder than any outside analogy suggestsWhy IBM Watson, Babylon AI, and Olive AI all failed the same way — and what the pattern revealsHow UnityAI ran five simultaneous market experiments to find its ICP after health systems proved unsustainableWhy PE-backed ambulatory roll-ups became the beachhead: 70–150 sites, national scale, PE efficiency mandates, and real capitalThe hospital delamination macro trend and why it makes UnityAI's addressable market structurally larger over timeHow UnityAI enters on voice AI demand and expands into full orchestration — and why the voice is just the edgeWhy co-developing with health systems kills startups, and the right sequencing to eventually sell into themGTM Lessons For B2B Founders:Sell workflows, not capabilities — and map every prerequisite before you pitch. Edmund identified this as the single common thread running through healthcare AI's most expensive failures: IBM Watson, Babylon AI, Olive AI. "The common failure mode is selling a capability, not a workflow." A voice AI, an RPA tool, a scheduling API — none of these land in a clinical environment without being integrated end-to-end into the actual task. Edmund's framework for what that means: What task am I going to achieve? What are all the prerequisites for that task? Who's doing it? How are they doing it? How does it all interconnect? Founders selling into operationally complex environments need to answer all of those questions before they pitch — not after.VC incentives and healthcare complexity are structurally misaligned — and that's your moat. Edmund is pointed about why well-funded companies keep failing: "In Silicon Valley you want to solve this huge giant TAM issue because that's how you raise money. In healthcare you can't actually fully do that... You can make a big promise, but you can't deliver on it in reality." The companies that raised $900M–$1B and sold for parts made the same mistake: they pitched the maximum addressable outcome to get funded, then couldn't execute against the operational complexity underneath. The founder who correctly sizes what is tractable, proves it, and expands from there has a structural advantage that over-capitalized competitors cannot easily replicate.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPy

TabaPay is rewriting the payment infrastructure stack for fintechs, lenders, and money-moving businesses — delivering the low-cost, instant, round-trip payment capabilities that established acquirers wouldn't offer and the market had no clean solution for. Founded in 2017 after Rodney Robinson spent years operating inside money transmission and the MasterCard ecosystem, TabaPay was built on a thesis that has held intact for nine years: lenders and fintechs are real businesses with real margin pressure, and they deserve payment infrastructure priced accordingly. In a recent episode of BUILDERS, we sat down with Rodney Robinson, CEO and Co-Founder of TabaPay, to explore how he finds problems worth building companies around, why software is no longer a defensible moat, and how TabaPay's three-pillar architecture — software, money transmission licensing, and banking — is designed to be structurally impossible to replicate from a garage.Topics Discussed:Why deep industry immersion — not ideation — is the only reliable method for finding problems worth building companies aroundThe founding thesis behind TabaPay: combining low-cost card acquiring with instant push-pull payments to serve the round-trip needs of lenders and fintechsWhy TabaPay's original ICP from 2017 is still accurate nine years later — and what "expansion without drift" actually looks like in practiceThe "one degree of difference" rule Rodney applies to every new market or product decision — and the acquisition that almost broke a company when he violated itWhy Rodney runs a small sales force and invests in marketing and channel distribution to drive inbound — and has never wanted it any other wayHow TabaPay goes to market before the product is live — and why MasterCard threatened to sue over a marketing websiteGTM Lessons For B2B Founders:Industry immersion is the methodology — ideation is not. Rodney's first company came from driving a liquor delivery truck at 17 and spotting a real operational constraint: stores couldn't transfer liquor across state lines due to tax law, so he built software that let them aggregate within a state for volume discounts. TabaPay came from running a money transmitter, struggling to get affordable card acquiring, and then selling a push-payment company to MasterCard — only to find all his customers wanted pull. The pattern across his 40-plus year career is the same: the problem finds you when you're deep in the work. Founders who start from ideation alone tend to solve technical problems no one urgently needs solved.Build your pricing model around margin visibility from day one. Rodney's insight that shapes TabaPay's entire value proposition: when you're transmitting money, your cost is visible to the customer in a way it isn't when you're selling a TV. "There's no profit on money except what the customer sees." That structural reality means payment costs hit fintech margins transparently — which is why affordable card acquiring is existential for lenders and money transmitters, not just preferable. Founders selling into margin-sensitive, fee-transparent verticals need to factor this in from the start: your pricing model is part of your product.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Health insurance hasn't fundamentally changed since a vice president at Baylor University created it with a group of nurses in 1929. What started as a fringe benefit became a wartime recruitment tool in the 1940s, got codified into group insurance through the ERISA Act in the 1970s, and has remained structurally employer-tied ever since. The problem: that architecture assumes a workforce that no longer exists. As AI accelerates the shift toward contract, gig, and frontline work, the employer-group model is developing what Felix calls a "leakage" — and that leakage is the market.In a recent episode of BUILDERS, we sat down with Felix W. Ortiz III, Co-Founder and CEO of Smirk Health, to learn how he's building portable, personalized health insurance for the 1099 worker, the frontline employee, and the gig worker that legacy group plans were never designed to serve — and the hard GTM lessons from his fourth company build.Topics Discussed:Why the employer-tied insurance architecture breaks down in a micro-shift economy — and what the replacement looks likeHow Smirk Health used D2C as a behavioral research instrument before pivoting to embedded B2B distributionThe decision to lead with dental over medical to compress an enterprise sales cycle to four and a half monthsHow Felix runs a GTM org of a handful of people at the output level of eight to ten through an agentic AI layerThe tiered prospect sequencing strategy that turns early enterprise logos into a FOMO engineThe messaging shift — from technical positioning to ROI language — that unlocked enterprise tractionGTM Lessons For B2B Founders: Use D2C as a buyer research instrument before committing to a channel. Smirk Health's D2C launch wasn't a business model — it was a structured experiment to map persona behavior before locking in a distribution strategy. As Felix explained: "We tested pretty aggressively across that segment to understand the segmentation and then really narrowed that data in to optimize our funnel and then focus on the embedded distribution channel." The output wasn't just product validation — it was segmentation data that told them which personas existed, how they behaved differently, and which channel could scale those learnings efficiently. If your real motion is B2B embedded distribution, D2C can compress months of buyer research into weeks — but only if you're wired to extract signal and act on it, not just acquire customers.The window to pivot channel is narrower than founders think. The D2C-to-B2B transition worked at Smirk because Felix moved within a few quarters of launch. His read: "Had we waited another quarter or two, it would have started to become somewhat painful. The fact that we started literally within a few quarters of us launching the company gave us the flexibility to adjust accordingly." Most founders underestimate how fast structural inertia builds around a GTM motion — headcount, commission structures, marketing spend, and stakeholder expectations all calcify around whatever channel is generating early traction. By the time the data clearly argues for a pivot, the organizational cost of making it is already high. The signal almost always arrives before founders act on it.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Mach builds the autonomy stack for the off-highway world — the heavy equipment running agriculture, land care, mining, logistics, construction, and defense. Founded on technology roots going back to 2013, Mach integrates hardware and software directly onto existing OEM platforms, giving mid-market equipment manufacturers a fast path to autonomous operations without building it themselves. Mach's first commercial OEM deployment was with GUSS Automation, a California-based orchard sprayer company that scaled to approximately 200 machines running Mach's technology before being acquired by John Deere in 2025. In a recent episode of BUILDERS, we sat down with Colin Hurd, CEO of Mach, to learn how three companies, a decade of hard lessons, and a sharp pivot in go-to-market strategy shaped one of the most pragmatic autonomy platforms operating today.Topics Discussed:The through line connecting Colin's three companies — from physical equipment to autonomy — and why labor scarcity, not compaction or crop yield, was always the real problemHow Mach's first commercial OEM customer, GUSS Automation, scaled to roughly 200 machines before being acquired by John Deere, and what that outcome proved about the modelWhy LiDAR dropping from $80K to $3–5K fundamentally changed the commercial viability of off-highway autonomyThe failure pattern killing autonomy startups: layering EV platform development, new vehicle manufacturing, and autonomy simultaneouslyHow Mach pivoted from chasing traditional OEM timelines to a pull-through model — arriving at OEMs with a committed enterprise buyer already in handGTM Lessons For B2B Founders: Diagnose symptoms versus root causes before locking in your category: Colin's first company solved soil compaction problems before he recognized the real constraint was labor scarcity. "The initial problem I started solving was a symptom of a bigger problem, which was labor challenges. And labor challenges are probably what I will spend most of my career working to solve." The implication for founders is not philosophical — it directly determines your ICP, your competitive set, and your long-term defensibility. If you're solving a symptom, a better-funded competitor solving the root cause will eventually commoditize you. Keep pulling the thread before you build the category narrative.The fastest path to OEM revenue runs through the end customer, not the OEM: Mach spent years building relationships with traditional mid-market OEMs — companies around $1B in revenue with genuine interest in autonomy but multi-year commercialization timelines. The breakthrough came when Colin looked back through the revenue data and noticed the majority of actual closed revenue was coming from a different customer type entirely: non-traditional OEMs and enterprise fleet operators who were closest to the labor problem and moving fast. The tactical shift was then using those enterprise buyer relationships as pull-through leverage with OEMs — arriving at the manufacturer with a committed customer already attached. "We can go to the OEM and say, here's a buyer, here's the technology, and here's the customer." That reversal in sequencing — demand-first, then supply — compressed timelines significantly.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

BinSentry is bringing real-time inventory intelligence to one of the largest and most overlooked supply chains on the planet. The US animal feed industry alone processes over $200 billion in transactions annually — and globally, the number exceeds $1 trillion. Yet most feed mills still rely on humans manually peering into bins to estimate what's there, a workflow Ben Allen's grandfather would recognize from the 1950s. The core problem: feed behaves nothing like a uniform solid. It rat-holes, slants, and forms multiple peaks, making simple sensor-based measurement useless. BinSentry cracked accurate bin-level inventory measurement roughly six years ago using high-end time-of-flight cameras — and is now building the intelligence layer on top of that data across the world's largest animal protein operators. In a recent episode of BUILDERS, we sat down with Ben Allen, CEO of BinSentry, to learn how he sells into one of the most consolidated B2B markets in existence, why he walked away from selling to farmers entirely, and what it actually takes to close enterprise deals when your total US addressable customer base is 200 companies.Topics Discussed:The $1 trillion global feed mill supply chain — and why it still runs on human eyeballs and spreadsheetsWhy feed inventory measurement is a harder technical problem than it looks, and how BinSentry solved itBinSentry's deliberate decision to walk away from the farmer market entirely and go direct to enterpriseThe enterprise-startup mismatch: why selling "speed and innovation" kills deals with large buyersGTM Lessons For B2B Founders:ICP discipline is hardest when inbound arrives from outside it. BinSentry doesn't sell to farmers — not because the demand isn't there, but because Ben spent years earlier in his career trying to make the unit economics work for geographically dispersed sole proprietors and couldn't. The decision to go exclusively enterprise — Cargill, Wayne Sanderson Farms, Aviagen — was the result of that hard-won lesson, not a whiteboard exercise. The discipline challenge Ben names is specific: you get calls, real business interest, and you still have to say no. Founders who haven't done the work of understanding why a segment breaks their CAC model will always rationalize the exception. Founders who have done that work say no faster and spend more time on accounts that can actually compound.Enterprise buyers aren't buying innovation — they're managing career risk. Ben's most pointed observation is about what's actually happening on the other side of the table in an enterprise sales meeting. The executive evaluating your product isn't just asking whether it works — they're asking whether choosing you will make them look good or expose them. Large organizations move at scale, with serious money in motion, and the people inside them are accountable for vendor decisions. When a startup walks in and leads with speed, iteration, and how fast they can change things, an enterprise executive hears: instability, risk, and a vendor who might look different next quarter. The face you show enterprise has to lead with stability, expertise, and credibility — even when the internal reality is far more fluid. Ben's framing: you're not selling the environment you built. You're selling a corporate outcome.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

The cybersecurity industry has a problem it created itself. The tools exist to protect most organizations — but deploying and managing them costs seven dollars in services for every one dollar in software license. Multiply that across the eight to ten tools a company actually needs, and you've priced out the majority of the market. Zip Security was built to close that gap with AI and automation. In a recent episode of BUILDERS, we sat down with Joshua Zweig, Co-Founder and CEO of Zip Security, to discuss how he and co-founder Gabbi Merz are rethinking both the product and the go-to-market motion for a segment of the market that's been systematically underserved.Topics Discussed:How Palantir's edge-distributed operating model shaped Zip's internal culture — and where Josh deliberately diverged from itZip's hiring thesis practice: what they took from Palantir, what they changed, and why they run it for every single hireThe three-bucket framework Josh uses to segment the security market — and why company size is the wrong variableGTM Lessons For B2B Founders: Avoid the channel that compresses your price before you've proven your value. Josh made an active choice to skip MSPs despite that being the default playbook for SMB cybersecurity distribution. The reason is structural: MSPs lead with cost sensitivity — the conversation becomes "is this 80 cents a seat?" before you can establish what you're actually delivering. They also serve a bundled model (help desk, device provisioning, security) where Zip's focused security-in-a-box offering doesn't fit cleanly. The channel shapes the conversation, and the wrong channel shapes it badly from the start.Treat channel partners as the primary customer, not the path to the customer. Zip's most productive GTM motion has been building relationships with independent security consultants and vCISOs. Josh's framing was precise: "The right way for us to approach this market is really being laser focused on these folks and thinking about them as much as our customer, if not more than the end user." The structural reason this works: consultants deliver recommendations but don't implement. They hand off a security plan and point at the client. Zip closes that gap — which makes the consultant look better to their client, not just more efficient. Founders building indirect channels should ask whether they're making the partner more valuable to their customer, not just making the sale easier for themselves.Segment by operational security capacity, not company size. Josh's market framework has three buckets: zero-person IT/security teams (where the ops lead or head of engineering is also the de facto CISO), lightly staffed teams of two to five people who have the tools but can't weave them together effectively, and well-resourced teams like Palantir's. His ICP is the first two. A construction company with 800 employees can sit in the same bucket as a 50-person regulated healthcare company — what they share is the absence of the internal capacity to operationalize security. Firmographic proxies like headcount or revenue miss this entirely.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.ioThe Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

⁠Avantos AI⁠ is replacing the fragmented patchwork of CRMs, task managers, and paper-based workflows that financial services firms have relied on for decades with a single operating system for client management. Built on a knowledge graph and AI-native from the ground up, Avantos models the full complexity of financial relationships — client data, the service team, and the products clients hold — as a unified, contextual graph rather than disconnected tables. In a recent episode of BUILDERS, we sat down with ⁠Bassam Chaptini⁠, Co-Founder & CEO of Avantos AI, to hear how he and co-founder Rabih leveraged 20 years of financial services experience to identify a massive white space, validated it in stealth with a design partner before officially founding the company in September 2024, and are now expanding from wealth management into insurance, banking, and capital markets with anchor logos including Mercer Advisors, Guardian Life, Vanguard, and SEI.Topics Discussed:Why wealth management became the beachhead — and how Mercer Advisors resolved the market selection questionThe knowledge graph architecture decision: why relational tables broke down and what unlocked multi-entity data modelingWhy CRMs, task managers, and portfolio systems all fail at the same thing — and what "swivel chair" actually costsHow Avantos used Series A design partners at Guardian Life, Vanguard, and SEI to de-risk expansion into adjacent verticalsThe category naming problem: why "CRM" is a hijacked term and what it takes to position as an operating systemBranding into a conservative enterprise buyer: the deliberate calibration between tech credibility and institutional trustWhy enterprise GTM at the foundational layer doesn't require marketing — and when that changesGTM Lessons For B2B Founders: Let the buyer who shows up first tell you which market to enter. Bassam and his co-founder had wealth management, insurance, capital markets, and banking all on the table simultaneously. What broke the tie wasn't analysis — it was Mercer Advisors arriving with a clear mandate. The president of Mercer came in saying what they had in place didn't work and wanted to co-build something new. Avantos partnered with them in stealth to validate the platform before officially founding the company. When a specific buyer shows up with that level of urgency and is willing to build with you, that's a stronger signal than any market sizing exercise. The analysis can follow.Relational tables will eventually break your data model — know when to reach for a graph. When Avantos first tried to represent the three-way relationship between clients, the service team, and the products clients hold, they started with traditional relational tables. Bassam is direct about what happened: it got out of control quickly regardless of how you structure it, which is why firms revert to paper. The knowledge graph solved it because it can represent arbitrarily complex relationships between data entities without the model collapsing — and as a side effect, it turned out to be natively well-suited for AI agents, which require rich contextual data to operate effectively. For founders building in any domain with deeply interconnected entities, this is a meaningful architectural lesson about where relational models fail.// Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership.⁠ www.FrontLines.io⁠The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.⁠ www.GlobalTalent.co⁠//Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here:⁠ https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM⁠