Podcast
Breakthrough AI Operators
Hosted by Roland Siebelink · EN
Breakthrough AI Operators is a podcast about how the best startup founders are reinventing how their companies work. Not AI hype. Not vendor pitches. Real operators who've rebuilt significant parts of their business around AI — and can talk honestly about what worked and what didn't.
Hosted by Roland Siebelink and Doug Miller, co-founders of Midstage Accelerator (7 unicorns built between them, 100+ leadership teams scaled), each episode features a founder who's achieved a genuine step-change breakthrough in how their company operates. These aren't productivity wins or tool adoption stories — they're companies that are structurally different because of AI.
If you're a founder at a 20–300 person company actively figuring out what AI means for your operating model and competitive position, this show gives you real stories from people in the field — not consultants theorizing from the sidelines.
11episodes
Episodes
Newest firstAll episodes
Unicorn in the Making: The Playbook for Scaling from $1M to $100M | Midstage Accelerator | Payandeh Ekrami | EP 204
6d ago00:30:46Tap to summarizeMost founders believe their team isn't aligned because the team isn't capable enough. Almost none of them have considered that the team can't align around a direction that lives entirely inside the founder's head. That distinction — between a team development problem and a founder bottleneck problem — is the one that determines whether a scaling company breaks through or breaks down. Payandeh Ekrami is a seasoned enterprise technology sales executive with senior leadership roles at Snowflake, Anaplan, and Samsung, specialising in helping high-growth companies build and scale revenue organisations. In this episode, she turns the mic around on Roland — interviewing him about the patterns he's observed across three unicorn journeys and what those patterns mean for any founder navigating the mid-stage transition today. The conversation surfaces two things that rarely appear together in the same discussion. The first is Roland's diagnostic of why founder-led companies stall — not at the market or product level, but at the operating level, when the habits that built the business start blocking the next stage of growth. The second is the more personal thread Payandeh draws out: Roland's underlying conviction that every person can find a context where they genuinely excel, and that one of the most important things any leader can do — including a founder — is help the people around them find that fit rather than forcing them into shapes that don't suit them. Roland names several specific tools and moments that illustrate how Midstage Accelerator does its work. The first workshop exercise — asking every leadership team member to write down independently what they believe they're responsible for — has made teams cry from the frustration of seeing how misaligned they actually were, with a head of engineering optimising for zero outages while the CEO expected ten monthly product launches. The practice of asking a founder CEO to sit quietly and speak last in workshop discussions reliably reveals which team members have been contributing original thinking and which have been echoing the founder back. And the question Roland poses before every engagement — do you work for yourself, or do you work for the company? — functions as a direct filter for whether the founder is building a business or building a legacy. Roland notes that the founders who reach the mid-stage with the strongest track records are often the hardest to work with at first — precisely because their instinct to be the smartest, most decisive person in the room is what got them there. The move from managing by assignment to managing by area, from controlling every detail to setting outcomes and trusting people to own their domains, is not a knowledge problem. It is a psychological one. What changes the equation, in his experience, is not convincing founders to delegate — it is lighting a bigger fire for what becomes possible when they do. Key Moments: 00:00 — Roland's opening claim: why seeing the movie three times is the core value he brings to founders 02:16 — What makes the mid-stage different from early-stage startup and from running an established company 05:50 — Why Roland calls himself an accelerator, not a coach — and what the distinction actually means 08:24 — The workshop instruction Roland gives every new founder CEO: sit down, be quiet, speak last 10:02 — What that silence reveals about who's actually thinking on the team versus who's been echoing the founder 12:52 — The alignment exercise that has made leadership teams cry: write down what you think you're responsible for 14:19 — The one question Roland asks before signing any engagement — and why the answer is a green flag or a red flag 16:00 — The Orange Communications "today and tomorrow" model: how to keep innovation alive without burning down operations 20:00 — The flywheel framework: four functions, one simple picture, and why it makes delegation feel possible 25:04 — What Roland looks for before taking on a client: ambition, coachability, and pride in the craft of leadership If you're a founder CEO navigating the transition from doing everything yourself to leading through a team, and you want a diagnostic on where the real bottlenecks are, reach out to Midstage Institute to start the conversation. mdstg.ac/drag-erase #StartupScaling #UnicornFounder #FounderCEOCoaching #MidStageStartup #BreakthroughAIOperators
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The Boring Part Is the Defensible Part | Evercam | Marco Herbst | EP 203
2w ago00:28:20Tap to summarizeWhat does it actually take to build an AI-powered construction intelligence platform — and why does it take 12 years? Most founders trying to layer AI onto physical industries discover too late that the data problem is the real problem. The model is only as good as what you fed it, and construction sites are the least controlled environments on earth. One company solved that problem by not trying to skip it. Marco Herbst is the founder and CEO of Evercam, a Reality Driven Intelligence platform that has accumulated 13,000 years of labeled construction video across 2,500+ customers including Intel, Microsoft, Meta, and Shell — built over 12 years of deliberate, unglamorous infrastructure work before the AI moment arrived. Marco's path to construction wasn't linear. He co-founded Jobs.ie in the early internet era and sold it in 2005, spent five years in Berlin by design, then returned to Ireland drawn by something specific: cameras as a communications tool, and the growing gap between what IP cameras could do and what construction sites actually needed. The early years weren't about intelligence — they were about reliability. Keeping a camera alive on a site for 18 months without maintenance, in weather, in dust, in a world where a late-detected problem adds zeros to the cost. That obsession, which looked like constraint, became the foundation for everything that followed. The second thread of the conversation is equally useful for any founder navigating the scale-up transition. Marco describes hiring three successive commercial leaders across the company's growth arc — each one suited to a different stage — and the structural decision to divide Evercam into regional P&L profit centers when telling a coherent story across eight global markets became impossible from the center. He also introduces the Evercam 100: a publicly available library of 100 construction workflows that deliver measurable ROI, hosted at workflows.evercam.io. Marco's reasoning for publishing it openly — that sharing information leads to better outcomes over the long arc — is both a genuine conviction and a strategic bet on collaboration winning over protection. Roland notes that Marco's story is the clearest example he's encountered of a founder earning the AI advantage the slow way — by doing the data work no one else was willing to do, long before AI made the data valuable. In his advisory work with SaaS companies at the $1M–$50M stage, Roland consistently sees founders who want to compete on intelligence before they've built a reliable data layer. The founders who resist that shortcut — who treat the infrastructure as the product until it actually works — tend to arrive at the AI moment with something competitors can't replicate quickly. Marco's 13,000 years of labeled construction footage is the most concrete version of that principle Roland has seen. Key Moments: 00:00 — Marco's definition of product-market-fit: the 2am call from Texas 02:05 — Why Evercam chose hardware reliability over AI — and why it was the right call 03:01 — From Berlin sabbatical to construction cameras: how Marco spotted a gap no software founder was looking at 05:22 — The moment construction clicked — and why security cameras never did 07:17 — How the mission-critical sector (Intel, Microsoft, Meta, Shell) took Evercam global 09:25 — Dividing into regional P&L profit centers to manage 8 global markets coherently 10:08 — Three commercial leaders across three growth stages: zero to one, one to ten, ten to one hundred 13:32 — How VLMs transformed what Evercam can detect — from counting vehicles to spotting unscheduled hazardous activity 16:43 — The Evercam 100: why they published 100 customer ROI workflows openly, and what it signals about their culture 19:52 — Why Marco published the workflows: a genuine conviction that collaboration wins over the long arc 21:32 — From "font police" to "management by joy": Marco's evolution as a founder and what it means in practice — If you're navigating the transition from founder-led construction sales to a scalable commercial model — or trying to understand how AI creates defensibility in physical industries — contact us to tell us about your project at https://www.evercam.com/roi-calculator. If scaling a hardware-software business across global markets is a challenge you're working through right now, Midstage works with founders at the $1M–$50M stage on exactly this kind of inflection. mdstg.ac/drag-erase #ConstructionTechnology #ConstructionIntelligence #AIConstruction #FounderLedSales #BreakthroughAIOperators
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Most Companies Are Measuring Marketing Wrong — And AI Won't Save Them | Hawke Media | Erik Huberman | EP 202
3w ago00:25:13Tap to summarizeMost founders have more marketing data than they know what to do with — and are making worse decisions because of it. The issue isn't measurement. It's that the metrics they're watching were never designed to match the sales cycle they're actually running. When you compare this week's ad spend to this week's revenue in a business where the average purchase takes a month to close, you will always misread what's working. Erik Huberman has watched this exact pattern destroy good campaigns — and has the data from 5,000+ brands to prove it. Erik is the founder and CEO of Hawke Media, a full-service outsourced marketing agency that has helped over 5,000 brands — including Red Bull, Verizon, and Crocs — generate nearly $3 billion in client revenue. He built Hawke from scratch into a 250-person bootstrapped company and spent eight years turning client data into a proprietary AI platform trained on over $700 million in media spend. The conversation opens on a problem Erik sees across every category: founders who look at ROAS on a weekly or monthly basis and draw conclusions that are structurally wrong. If a sales cycle averages 30 days, scaling ad spend from $1K to $5K daily won't show up in revenue for two months — but most founders see flat revenue, conclude the channel doesn't work, and cut the spend that was compounding. Erik's argument isn't that data is bad. It's that a correct data point, read through the wrong frame, produces confident, wrong decisions. He extends this into a broader claim about the AI hype cycle: that much of what AI is being credited with is the same problem — regurgitating inputs without understanding the context that makes data meaningful. The second thread in the episode is about what it actually takes to build something that scales. Erik's 90/10 framework — 90% of budget and effort to scalable, repeatable marketing, 10% to viral — runs counter to how most first-time founders allocate attention. He's seen viral moments generate $10 million in revenue, trigger infrastructure build-out, then vanish — leaving a company with overhead designed for a spike that's already gone. He's equally direct on the executive team side: coming out of COVID, he identified a specific type of stagnation — people who kept referencing the good old days instead of building toward what came next — and made significant changes. The quality he says is hardest to find, and most essential to keep, isn't talent. It's the specific kind of grit that lets someone miss a goal, absorb it, and keep charging. Roland observes that the measurement problem Erik describes — having access to data without knowing what it means — mirrors a pattern he sees consistently in SaaS companies at the $3M–$15M stage. Founders at this stage have typically invested in reporting infrastructure, but the cadence and frame of the reports were built around what's easy to pull, not what reflects their actual sales cycle. The result is a false confidence in the numbers that makes it harder, not easier, to allocate well. Erik's experience — and his data across 5,000 brands — suggests this isn't a scale problem. It's a framing problem that shows up at every stage. Key Moments: 00:02 — Erik's opening claim: AI is mostly regurgitating the internet — and why that's a bigger problem than most companies realize 02:13 — The ROAS fallacy: why comparing this month's spend to this month's revenue will make you cut your best campaigns 04:39 — What actually happens when you scale ad spend from $1K to $5K daily — and why the numbers look broken even when the strategy is working 06:40 — How Hawke uses AI internally: augmentation over automation, and why the "army of 20-year-old interns" framing is more accurate than the hype 12:16 — CEO alignment vs. optimization: why marching in the wrong direction together often beats optimizing in five different ones 15:42 — The 2024 executive team inflection point: what Erik changed, who he kept, and the specific behavior pattern that triggered most of the exits 18:44 — The honest pitch Erik makes to every new hire — and why he deliberately screens out people who find it unappealing 22:28 — The 90/10 marketing rule: why scalable and repeatable should get 90% of your budget, and what happens to companies that chase viral instead 23:39 — The viral sugar rush: how a $10M viral moment can cost a company $10M in infrastructure it no longer needs 25:02 — The Forbes 30 Under 30 moment that made Erik feel, for the first time, like he was competing in the thing he was built for — Hawke Media is offering listeners a free marketing audit. This is most useful for growth-stage companies that are spending on marketing but aren't confident their measurement approach is reflecting their actual sales cycle. https://hawkemedia.com If you're spending on marketing but not sure whether your reporting frame is set up to match your actual sales cycle, this is the kind of problem Midstage works through directly with founders at the $1M–$50M stage. mdstg.ac/drag-erase #MarketingMeasurement #StartupMarketing #OutsourcedCMO #MarketingAgencyScaling #BreakthroughAIOperators
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The Unlikely AI Pioneer: How heyData Out-Innovates Flashier Silicon Valley Startups | heyData | Miloš Djurdjević | EP 201
4w ago00:28:39Tap to summarizeThe most advanced AI operating model in this episode wasn't built from a strategy deck. It was built from desperation — and that turns out to be the best design constraint available. Miloš Djurdjevic is co-CEO and co-founder of heyData, a Berlin-based compliance platform that scaled to several thousand customers, closed a $16.5M Series A, and kept the team at 60 people — on purpose — while running more than 14 AI agents in marketing, near-fully automated customer support, and more agents than headcount in revenue operations. When heyData was growing fastest before its Series A, the team didn't have a choice. There weren't enough people to handle the customer volume, the compliance questions, or the marketing load. So they started automating — not because it was fashionable, but because the alternative was falling behind. Customer success built a knowledge base from years of accumulated compliance Q&A, then layered AI agents on top until response times dropped from several days to under an hour. Marketing restructured an entire role around managing and iterating on agents rather than producing output directly. Revenue ops rebuilt itself around agents first, humans second. The thread running through all of it: the team was too stretched to be afraid of AI. Every person saw it as capacity relief, not a threat. The secondary conversation in this episode is one Roland flags as increasingly important: whether BI as a function becomes obsolete in an AI-first company. Miloš's answer is direct — at heyData, they depend on it more than ever, not less. As AI takes on more of the analytical work, the job of the BI team shifts from producing reports to ensuring the data underneath those reports is structured, clean, and trustworthy. AI is only as useful as the data that feeds it, and that data hygiene work still requires dedicated human judgment. It's not a disappearing role — it's a fundamentally different one. Roland observes that the heyData story confirms something he sees consistently in his advisory work: durable AI adoption almost never starts with a mandate. It starts with a constraint. The founders who have the most sophisticated AI operations today are, disproportionately, the ones who had no other option a year or two ago. Understanding that dynamic — and what it takes to replicate the results without the underlying pressure — is the open question this episode raises. Key Moments: 00:00 — Why a compliance company became an AI operations lab before AI was fashionable 01:57 — The deliberate case for staying at 60 people after a $16.5M raise — and what every new hire actually costs 05:10 — How heyData built its first AI system in customer success: from a knowledge base of compliance Q&A to sub-hour response times 08:10 — Top-down vs. bottom-up AI adoption — and the cross-functional task force model that made both work together 10:31 — Why heyData's team never feared AI would cost them their jobs — and the specific context that made that true 14:16 — Is BI becoming obsolete in an AI-first company? Miloš's honest answer, and what the role actually becomes 17:21 — Raising a $16.5M Series A in a market that demands AI nativeness — what was harder than expected, and what wasn't 19:31 — 14 AI agents in a 6-person marketing team: how the role of "AI lead" got created and what that person actually does 22:52 — The personal backstory: growing up between Bavaria and Serbia, two doctors for parents, and what persistence looks like when it's inherited If building an AI-augmented operating model — rather than just adopting AI tools — is the challenge in front of your team right now, a Breakthrough Workshop with Midstage is the fastest way to find the right leverage point. Book at breakthrough.midstage.ac #AIOperators #ComplianceTech #AgentFirst #SaaSFounders #BreakthroughAIOperators
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The AI Breakthrough Stories Most Founders Are Not Telling | Midstage Accelerator | Doug Miller | EP 200
May 2700:29:15Tap to summarizeMost AI adoption failures at growing startups aren't technology problems. They're a founder who is moving fast, surrounded by a team that isn't — and a growing gap between the two that no new tool subscription will close. Roland Siebelink is co-founder of Midstage Accelerator, who has helped scale three unicorns across three countries — each from roughly 10 to 1,000 people in three years — before spending the last decade advising SaaS companies on the hardest years of growth between $1M and $50M. At episode 200, Roland sits down with co-founder Doug to open a new chapter for Scaling Without Breaking: a focused series on what it actually takes to achieve a breakthrough with AI in your operations. The episode starts with a distinction that shapes everything that follows — the difference between using AI and breaking through with AI. Roland's position is clear: AI is a means to an end, and the founders who treat it as the end are the ones who end up more productive and more isolated, running faster while their company catches up. The conversation moves through a telling example — a financial services company that spent years with a six-week manual loan review process, not because the knowledge wasn't there, but because nobody had been able to translate that knowledge into reliable, deterministic code. AI agents changed the equation not by replacing the loan officers but by allowing experimentation that, over time, outperformed the junior hires who had been doing the work. The secondary thread is one that Roland says he sees constantly: the founder who has adopted five or six AI tools, feels dramatically more productive, and cannot understand why their team isn't following. His observation is that the moment a founder prescribes how AI should be used — here's the tool, here's the workflow — they strip away the one thing that makes adoption stick: the team member's own discovery of how AI changes their specific job. The episode closes with Roland describing what Midstage calls the "50% startup" — not a company where AI replaces people, but one where humans and agents each do what the other can't, led by founders who understand the difference. Roland notes that one of the clearest patterns he sees in his advisory work is that the founders who get the most out of AI are rarely the most technical. They're the ones who build the conditions for the team to find the leverage themselves — and who resist the urge to be the chief AI evangelist in their own company. At the $1M–$50M stage, the bottleneck is almost never the tools. It's the change management. Key Moments: 00:00 — Why episode 200 is the right moment to reorient the podcast around AI breakthroughs 01:56 — The difference between using AI and achieving a breakthrough with AI — and why it matters for momentum 03:53 — How an AI coaching agent helped a founder stop dominating team meetings — without a single conversation about it 07:11 — Why an HVAC contractor using an AI phone agent is already outgrowing competitors who can't figure out responsiveness 09:48 — The Venn diagram between AI-native companies and AI operators — and where the real growth is happening 11:25 — The financial services loan company: how AI agents compressed a six-week manual process and what made it stick 16:33 — Why the founder who is "street lengths ahead" on AI tools is sometimes the biggest obstacle to adoption 18:28 — Roland's background: three unicorns, three countries, and what repeated exposure to scaling reveals that first-timers can't see 22:08 — Why external perspective finds the real problem faster — and why founders are often solving the wrong one 26:17 — How to book a Breakthrough Workshop with Midstage and what to expect from it --- Midstage Accelerator is offering founders a Breakthrough Workshop — a facilitated session designed to identify the real constraint in your business and produce a clear path forward. If the gap between your AI adoption and your team's is something you're navigating, this is where to start. Book at breakthrough.midstage.ac #AIOperators #FounderLedGrowth #SaaSFounders #ChangeManagement #BreakthroughAIOperators
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From PE Boardroom to Operator — What Investors Get Wrong | HCIM | Ali Evans | EP 122
May 1300:29:03Tap to summarizeMost PE investors see a 25-year-old automation business in 2026 and calculate the half-life. Ali Evans saw the one thing AI can't replicate overnight: trust earned over decades of client relationships. The conventional move would have been to exit before disruption. He acquired the company instead and stepped into the CEO chair. Ali Evans spent years at Francisco Partners and Riverside writing checks and sitting on boards before leaving the investor seat to acquire HCIM, a healthcare automation company founded in 2000. He's now CEO of the firm he owns at the fund level, navigating the rare dual role of PE investor and operating executive. The first challenge Ali walked into wasn't technical — it was linguistic. Founders and investors use the same vocabulary but optimize for completely different outcomes. Founders want to solve more customer problems. Investors want to maximize return per unit of risk. That gap destroys trust in almost every PE-backed deal, and Ali found himself on both sides of it simultaneously. The moment he became CEO, he had to stop speaking in investor math and start speaking in the language his team actually cared about: impact, autonomy, and customer outcomes. The conversation also covers why Ali doubled down on healthcare automation in the age of AI, why he thinks relationships and trust are harder to replicate than technical expertise, and the story behind Metamora — his firm's name, which comes from the hardest week of his life at a small-town football camp that taught him what it means to bond a team through crucible moments. Roland sees this founder-investor language barrier break down trust in almost every SaaS deal he advises on at the $5M–$20M stage. The misalignment isn't usually strategic — it's definitional. Both sides think they're talking about growth, but the founder means "how many more customers can we help" and the investor means "what's our IRR on this capital deployed." Ali's experience living in both seats at once confirms what Roland keeps telling both founders and their backers: you're not disagreeing on the plan. You're disagreeing on whose calculus gets to define success. Key Moments: 01:58 — Why AI can mimic expertise but can't replace 25 years of earned trust — and why that's the bet Ali made 05:33 — The Spanish vs Portuguese problem: how founders and investors use the same words but mean completely different things 08:01 — The exact moment Ali realized his team didn't care about risk-adjusted returns — and why he had to unlearn investor-speak to lead 12:45 — Why most founder-investor conflicts aren't strategic disagreements — they're fights over whose definition of success matters 16:30 — How Ali transitioned from writing checks to running the company — and the due diligence he did on himself before becoming CEO 21:10 — What agentic AI workflows are actually doing in healthcare automation — beyond the marketing buzz 25:22 — The Metamora origin story: how a brutal high school football camp became the name of Ali's firm — and what it taught him about bonding teams through hard things HCIM is offering listeners a free workflow automation readiness assessment report. If you're running a healthcare payer operation and wondering where RPA could save real operational time, reach out at https://hcim.com/contact/ If bridging the gap between founder-speak and investor-speak is something you're navigating at the $5M–$20M stage, Midstage works directly with SaaS CEOs to translate strategy into execution without losing either side. mdstg.ac/drag-erase #PrivateEquity #HealthcareAutomation #FounderInvestorDynamics #OperatorCEO #ScalingWithoutBreaking
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Why 20 People Can Beat Billion-Dollar AI Companies | Deep Infra | Nikola Borisov | EP 121
May 600:25:03Tap to summarizeOpen source AI models are now just 3-5% behind the best closed source models on benchmarks — about six months of lag time, not five years. If you're building an AI infrastructure company on the assumption that OpenAI or Anthropic will maintain a permanent lead, your moat is disappearing faster than your revenue projections assume. Most founders at the $3M–$20M stage are still over-indexed on model selection and under-indexed on inference economics. They're obsessed with training costs and model access, but the real cost explosion is coming from running models at scale. A model that trains for a year but only runs for a month is a terrible investment — and yet that's how most AI budgets are still structured. Nikola Borisov spent a decade building backend infrastructure for a chat app with 200 million monthly users before launching Deep Infra. He's CEO and co-founder of Deep Infra, an AI inference platform that owns its own GPU clusters and serves as one of the largest token suppliers on OpenRouter. The episode centers on two bets Nikola made that most infrastructure founders won't: first, that open source models would catch up to closed source models faster than anyone expected, and second, that inference — not training — would dominate AI budgets within five years. Those bets are both paying off. The gap has narrowed to 3-5%, and as Deep Infra lowers costs, customers aren't just consuming more tokens — they're jumping to better, bigger models. The conversation also surfaces a less obvious pattern: the economics of AI inference mirror the economics of CDNs more than they mirror cloud compute. Walmart and Target don't care if their images are served from the same CDN — it's just an efficient way to deliver content. Deep Infra runs the same model for multiple companies in parallel on the same GPUs, and neither company cares. It's neutral infrastructure that scales horizontally without requiring every company to build their own. Roland sees this pattern constantly in his advisory work with SaaS companies scaling from $1M to $50M: founders are modeling their AI spend around closed source API access and per-token pricing, but they're not accounting for what happens when open source closes the gap and inference costs drop 20x. The companies that move early to open source inference infrastructure will have a cost structure their competitors can't match in 18 months — and cost structure at scale is the actual competitive wedge, not model access. Key Moments: 3:01 — Why the gap between closed source and open source models has narrowed to 3-5% — and what that percentage actually measures 5:00 — The five-year-old explanation of inference: training is school, running the model is work 6:41 — Why Anthropic's compute conflict (training vs. serving customers) reveals the real economic wedge 10:39 — The CDN analogy: why Walmart and Target don't care if their requests run on the same infrastructure 16:12 — How lowering costs changes customer behavior — they jump to bigger models, not just more tokens 18:51 — Why Nikola believes inference will dominate company budgets in 5-10 years 20:29 — What a math Olympiad medalist and programming competitor learned about certainty that still drives how he builds 22:31 — Nikola's advice to younger founders: focus on what's most important today, not what's interesting --- If navigating AI infrastructure economics — balancing model access, inference costs, and long-term vendor lock-in — is something you're working through right now, the Midstage Accelerator helps SaaS founders at the $1M–$50M stage model these decisions with real unit economics and stage-specific benchmarks. mdstg.ac/drag-erase #AIInfrastructure #OpenSourceAI #InferenceEconomics #SaaSScaling #ScalingWithoutBreaking
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Built real-time private company valuations that take hours, not months — while staying profitable in an industry where competitors bleed money | Eqvista | Tom Milar | EP 120
Apr 3000:24:39Tap to summarizeEvery cap table company in Silicon Valley is burning venture capital chasing growth. Tom Milar built one that makes money instead — and he did it without ever raising a pre-seed round, despite managing $300 billion in client assets for companies including Perplexity AI. The question this episode refuses to let go of is whether the VC-fueled growth playbook has become so normalized that founders have forgotten there's another way to build. It turns out the founders closest to the problem — the ones who see thousands of cap tables and valuations up close — might have the clearest view of what's actually driving company value. Tom is the founder and CEO of Eqvista who built and sold the largest incorporation provider in Hong Kong, acquired the largest registered agent in Nevada, and then built a profitable valuation and cap table platform serving 23,000+ companies — all without a single successful fundraising round. The core of this episode is Tom's "European Hong Kong pragmatism" — a phrase that sounds like a geographic contradiction but is actually one of the most coherent operating philosophies in the episode. Where Silicon Valley rewards the pitch, Tom rewards the product. His argument is direct: the first version of everything — the code, the pricing, the privacy policy, the initial client agreements — has to come from the founder. Not because delegation is wrong, but because no hired CTO or product manager can build what they don't deeply understand. Eqvista's website was, by Tom's own description, hideous for six years. He left it that way deliberately. When he eventually changed the design, conversions didn't move. Neil Patel, who served as board president at one of Tom's acquired companies, had told him the same thing: you can kill a business by touching what's already working. The insight Tom keeps returning to is deceptively simple — build a hierarchy of problems by asking which ones are closest to revenue, and work down from there. Everything else is noise. The secondary thread is what Tom observes watching founders up close through Eqvista's platform, where he sees not just cap tables but the underlying behaviors of companies raising seed rounds, Series A, and beyond. His diagnosis of why founders move too slowly isn't about effort — it's about sequencing. The founders who fail are the ones who raise $400,000 before doing the heavy lifting themselves, who hire before they understand the product, who feed the beast with venture money before the product is strong enough to stand on its own. The real-time valuation product Tom demos in the episode crystallizes what's at stake: the two factors that drive private company valuations fastest are revenue and how well a founder can sell equity. Everything else — the design, the brand, the org chart — is downstream of those two numbers. What Roland observes repeatedly at the $1M–$50M stage is that the founders who stay profitable longest tend to have built an intuition about revenue proximity that their VC-backed peers often lack — not because they're more talented, but because they've never had the option of substituting capital for clarity. The discipline Tom describes, building a hierarchy of problems anchored to what makes money, is something most founders only develop after they've run out of runway once. The companies that arrive at Midstage having bootstrapped or stayed lean tend to have sharper product instincts and messier org charts; the ones that raised heavily tend to have the reverse. Neither is inherently better, but knowing which problem you have is the first step to fixing it. Key Moments 00:39 — Why Tom couldn't raise a pre-seed round despite having multi-billion dollar companies as clients — and why he's not sure it mattered 02:32 — "European Hong Kong pragmatism": what it actually means to build profitable companies in a culture that rewards hype over product 04:45 — Why the first code, pricing, and client agreement must come from the founder — and what gets lost when founders skip that step 08:25 — Two types of founders Tom sees up close: the ones who can raise, and the ones who can build — and why the ideal is rarer than anyone admits 10:02 — The real-time valuation demo: what a living stock price for a private company looks like, and why fund admins processing 500 companies traditionally need six people for six months to do what Eqvista does automatically 13:33 — The one filter Tom uses to cut through every meeting, every email, every decision: what makes money? 14:36 — Why Eqvista's website stayed hideous for six years — and what happened to conversions when they finally fixed it 16:29 — The founder sequencing trap: why raising $400K before doing the heavy lifting yourself is one of the fastest ways to fail 18:01 — The two factors that drive private company valuations the fastest — and what every founder building toward a raise needs to understand first --- Eqvista is offering Scaling Without Breaking listeners $100 off their plan. If you're a founder managing equity, planning a raise, or wanting a real-time valuation for your company, this is the most direct way in. Use referral code ROLAND_EQVISTA at eqvista.com. If you're navigating how to structure equity, understand your company's true value, or think clearly about what a raise would actually do to your cap table, Midstage Institute works directly with SaaS and software founders at the $1M–$50M stage to help you make those decisions with clarity before they become expensive mistakes. mdstg.ac/drag-erase #EmployeeStockOptionPlan #PrivateEquity #VentureCapital #SeedRound #ScalingWithoutBreaking
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I Left My Company. Came Back to Find a Shell. Then Rebuilt It. | Wundertax | Daniel Hanemann | EP 119
Apr 2500:24:14Tap to summarizeMost founders who return to a company they once built come back to fix operations. Daniel Hanemann came back to WunderTax to find a company with 25 people, a plateauing market, and a unicorn competitor with 100x the marketing budget — and decided the answer wasn't to compete harder. It was to stop competing on the same terms entirely. The question this episode forces is one most SaaS founders never think to ask: what if the fastest path to growth isn't acquiring more customers, but becoming invisible infrastructure for someone else's product? Daniel is the co-founder and CEO who walked away from a company he'd built to a million euros in revenue, watched investors run it into the ground, returned to rebuild it from 25 people to a leaner 15, and then made a bet on an embedded API strategy that puts WunderTax inside competitors' products rather than in front of their customers. The core of this episode is the embedded play Daniel calls "flanking technology" — and it's more honest about the difficulty than most pivot stories tend to be. WunderTax processes around 100,000 tax returns per year for German consumers directly, but that market has hit a ceiling. The awareness battle has already been won by Taxfix (300 million euros raised) and Wiso Steuer (double Taxfix's revenue). Rather than fight an eight-digit marketing budget with a six-digit one, Daniel identified that WunderTax's API-first architecture was an asset he could open up — and began approaching other companies in the tax and accounting space who needed specific niche tax forms built but didn't want to build them. The embedded pilots are in motion. The grind of getting onto another company's product roadmap, as Daniel describes it plainly, is real. But the logic is sound: if you've already built the hard thing, why compete to be visible when you can become indispensable? The second thread is how Daniel actually executed the restructuring that made the pivot possible. He went from 25 people to 15 — and describes the approach not as radical transparency but as something quieter: sharing his train of thought with anyone who asked, explaining the reasoning behind decisions that would otherwise look like mismanagement, and letting people opt out with enough clarity to make the choice their own. The one person who left voluntarily did so because the culture had changed — he missed ordering the toilet paper. That's not a punchline. It's a precise illustration of what happens when you remove the accumulated slack from a company that survived long enough to develop it. Daniel also brings something genuinely unusual to this conversation: a background in standup comedy, which he credits for one of the cleanest mental models in the episode — every bad pitch, like every bad set, is forgotten faster than you think, and there's always another audience. What Roland observes repeatedly at the $1M–$50M stage is that the strategic inflection Daniel describes — the moment a founder realizes the GTM motion that got them here won't get them there — almost always arrives later than it should. The market ceiling becomes visible in the data months before founders are willing to act on it, because the existing revenue is real and the new motion is unproven. The founders who navigate it well tend to share one characteristic: they name the plateau before their board does, and they frame the new direction as a second launch pad rather than an admission of failure. Daniel's framing — "a soft pivot with a stable launch pad" — is one of the more useful constructs Roland has heard for explaining this transition to a team without triggering the uncertainty that kills execution. Key Moments 00:44 — Why WunderTax couldn't win a bidding war against Taxfix — and the moment Daniel stopped trying 03:15 — The "flanking technology" framework: how David actually beat Goliath, and what it means for a small SaaS player against an eight-digit marketing budget 04:36 — The honest part of the embedded pivot story: why getting onto another company's product roadmap is a grind no one talks about 07:52 — "A soft pivot with a stable launch pad" — Daniel's construct for changing direction without destabilizing the business that funds the change 09:18 — The toilet paper story: what it actually looks like when a company removes accumulated slack from a team that got comfortable with it 10:54 — Why transparency during restructuring isn't about radical openness — it's about sharing your train of thought so people can leave on their own terms 15:15 — You don't sell a company. You get bought. Daniel on why M&A is more like the dating market than the stock market 17:15 — What standup comedy taught Daniel about bad pitches, rejection, and why nobody remembers your worst performance as much as you do 19:04 — Growing up trilingual in Hong Kong with German and Taiwanese parents — and why "third culture kid" stopped feeling like a label and started feeling like a superpower WunderTax is offering German listeners a discount code on their tax filing plan. If you're an individual or expat filing taxes in Germany and want to try the simplest way to do it, reach out to Daniel directly at daniel@wundertax.com to claim your code. If the plateau Daniel describes — a running business that funds the present but doesn't point toward the future — is something you're staring at right now, Midstage Institute works with SaaS and software founders at the $1M–$50M stage to identify the inflection point and build the motion that gets you to the next level. http://mdstg.ac/drag-erase #TaxFilingGermany #EmbeddedFinance #StartupPivotStrategy #FounderComeback #ScalingWithoutBreaking
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I Spent My 18th Birthday Studying Credit Cards. Now I Run a Unicorn | Kikoff | Cynthia Chen | EP 118
Apr 1600:28:15Tap to summarizeMost fintech companies build products for people who already have access. Kikoff was built by someone who didn't. The question this episode forces a founder to sit with isn't about market sizing or product-market fit — it's about whether you actually understand the cost your customer pays when your product doesn't exist. That number, by the way, is a quarter million dollars over a lifetime. Cynthia Chen, co-founder and CEO of Kikoff, arrived in the United States at 17 with two suitcases, no credit, and no co-signer — and spent the next 15 years building the expertise to fix the system she had to survive. Cynthia is the founder who served as Kikoff's sole customer service rep until the company hit Series A with 30,000 active users — and still watches customer interviews and reads app reviews today. What this conversation reveals, underneath the unicorn milestone and the Inc. 500 recognition, is the operating philosophy that made it possible. Cynthia didn't build Kikoff by abstracting away from the customer. She built it by staying closer to them than any team member had reason to expect from a CEO. She personally took calls from customers who found her phone number. She ran Hack Weeks not as a culture perk but as a deliberate product velocity engine — with team members flying in from across the country to pair with people they wouldn't otherwise work with. The result isn't just a list of product ideas; it's a cross-functional collaboration that compounds after the week ends. The AI debt negotiator that Roland opens the episode describing — an AI that calls debt collectors on your behalf — came directly out of one of those Hack Weeks. That's not a coincidence. That's a system. The second thread running through this episode is one that every founder scaling through 50 to 200 people will recognize: the talent management problem that appears only after you survive the early years. Kikoff's first hires came from Cynthia's network. They didn't join for promotion paths or career ladders — they joined to build something with her. When Kikoff began hiring outside that network, those new team members arrived with different expectations. The career ladder Cynthia describes building isn't an HR formality; it's a retention mechanism for the company's second cohort. And the rubric she gives her team for autonomous decision-making — if it's legal and reversible, run the test — is one of the cleanest delegation frameworks in any episode of this show. What Roland observes repeatedly at the $1M–$50M stage is that the founders who stay closest to the customer the longest tend to build the most defensible products — not because proximity is a virtue, but because it's a compounding information advantage. The companies that abstract too early, that hand off customer feedback to a layer of product managers before the founder has developed their own intuition about what the customer actually fears, tend to build features instead of solutions. Cynthia handled customer service alone until 30,000 users. Most founders hand it off at 300. That gap shows up in product decisions for years afterward. Key Moments 00:38 — Why Cynthia spent her 18th birthday researching credit cards instead of celebrating — and what that night actually built 02:23 — What it felt like to arrive in the US with two suitcases and no credit, told by the person who then built a company around fixing it 06:12 — Why being 10x better isn't a slogan for Kikoff — it's the only way to earn trust when incumbents already own the search results 08:51 — How Hack Weeks became Kikoff's primary product innovation engine, not a morale exercise 12:46 — The talent management problem that only appeared after Kikoff survived early-stage: what happens when your second cohort expects a career ladder your first cohort never asked for 15:34 — The two-question rubric Cynthia gives every team member for autonomous decision-making: is it legal, and can you reverse it? 16:13 — Why Cynthia served as the only customer service rep until Series A — and why she says the learnings from those calls shaped every product decision that followed 18:43 — How Kikoff navigates AI deployment in a heavily regulated space serving underserved consumers — and why "is this good for the consumer?" is their most effective compliance framework 21:57 — The honest state of VC funding for female founders: why the recent improvement in numbers is narrower than the headlines suggest Kikoff is offering Scaling Without Breaking listeners 80% off their first month of any Kikoff plan. If you or someone you know is building credit from scratch — or needs to get back on track — this is the most accessible entry point they've built. Visit getkikoff.com/swb to claim the offer. If you're navigating the gap between your founding team's culture and the expectations of the talent you need to hire next, Midstage Institute works directly with SaaS and software founders at the $1M–$50M stage to build the operating infrastructure that makes that transition without losing what made the company work in the first place. mdstg.ac/drag-erase. #SaaSFounders #FintechLeadership #ProductVelocity #FounderLedGrowth #ScalingWithoutBreaking
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