In this episode, Osman walks us through exactly how to identify your ideal customers at the perfect moment, then demonstrates his framework live with two early-stage founders - showing you can't just wing GTM engineering, but when done right, the results compound.

Osman Sheikhnureldin is the Head of GTM Engineering at Clay, the company that invented GTM Engineering. He's helped hundreds of startups transform how they use data and technology to remove growth constraints. Joining him are Nilo Rahmani, Co-founder and CEO of Thoras AI (AI-driven cloud reliability and cost optimization), and Panos Papageorgiou, Co-founder of Keragon (HIPAA-compliant automation platform for healthcare).

In Today's Episode We Discuss:
01:51 - GTM engineering defined: Solving growth constraints with technology, not headcount
02:57 - Why your target list matters more than your message will ever matter
04:45 - Ditch static ICPs: The jobs-to-be-done framework that actually works
06:53 - The "magic wand" question every founder must answer before building workflows
08:49 - The account scoring workflow no human should ever do manually again
13:46 - How Clay built an ML model to predict contract value from enrichment data
19:18 - Vanta's genius GTM hack using AI screenshots to analyze brand consistency
21:30 - European food startup's signal stack: First US hire + ad spend + new landing pages
23:06 - Early-stage messaging must be hyper-specific—big company tactics won't work for you
26:54 - Founders who lived the pain have an unfair advantage in outbound messaging
28:59 - Counterintuitive truth: AI SDRs have failed—human taste matters more than ever
31:48 - Why hybrid LLM + human skeleton emails crush pure AI-generated copy
34:42 - Voice AI skepticism: Great for extraction, not ready for cold calls
37:18 - Three brutal truths: GTM engineering takes months, hard work, and real creativity
38:20 - "Earn the right to message someone"—the philosophy behind effective outbound
39:24 - Live teardown: Keragon's healthcare GTM using EHR migration as the trigger signal
47:08 - Finding EHR signals through PR announcements, patient portals, and RSS feeds
55:38 - Live teardown: Thoras AI's challenge—spotting cost-cutting triggers that signal growth
01:00:58 - Why "cutting costs" often means a company is scaling, not struggling
01:07:32 - Novel signal: Second product launch as the perfect moment to reach infrastructure teams
01:13:06 - The biggest misconception: GTM engineering goes far beyond cold outbound

I talked to the person who invented the role of GTM Engineer at Clay.

Yash Tekriwal, Clay's first GTM engineer - back when the $3B company was still figuring out what that even meant.

What started as one person drowning in too many jobs (RevOps + Sales + BDR + data analyst) has since become a new category that's now reshaping how startups think about go-to-market.

You’ll learn:

• Why RevOps is "maintenance" but GTM engineering is a growth lever
• The skills that define a great GTM engineer today (hint: it involves vibe coding)
• What "treating go-to-market like a product" actually looks like in practice
• Two org models for GTM engineering teams - and which to start with
• "Automate the manual, but don't automate the important"

In Today's Episode We Discuss:
01:23 - The origin story of GTM engineering at Clay and why the term is polarizing
05:02 - GTM engineer vs RevOps: maintenance function versus growth lever
07:31 - Treating go-to-market like a product team, not an individual sport
10:42 - Three experiments every GTM team should run on inbound and outbound
15:24 - The essential GTM tech stack: CRM, enrichment, sequencing, and what actually matters
19:08 - Tools founders should consider when getting started—and the automation trap to avoid
22:12 - Zero to $1M: be thrifty on tools and process information manually
25:38 - What to look for in your first GTM engineering hire (hint: it's not technical skills)
28:43 - Signals that you need to hire a GTM engineer for outbound vs inbound motions
31:45 - Scaling past $10M: specialize fast and the hyperscaler dilemma
36:01 - Two org models for GTM engineering: centralized hit team vs embedded engineers
40:22 - The ideal GTM engineer profile: tinkerers, not traditional engineers
43:33 - Why engineers are not the ideal candidates for GTM engineering roles
45:19 - Can salespeople become great GTM engineers? The sales hacker archetype
47:26 - Resources to learn GTM engineering: Clay University, substacks, YouTube channels, and agencies
51:00 - Top three things founders must know about GTM engineering at any stage
52:16 - The most creative GTM engineering builds: satellite imagery, hospital capacity, and custom memes
56:24 - Personal lessons from scaling at Clay: ego death, pivoting, and balancing maintenance with big bets
59:42 - The one thing Yash would change: stop oscillating and let problems become obvious

Should you build narrow (vertical) or go broad (horizontal) in AI? This episode unpacks why one PhD researcher abandoned his working vertical product to chase a much riskier horizontal bet - and why VCs leaning heavily into vertical AI might be missing something.

Abhishek Das is the co-founder and co-CEO of Yutori, which has raised over $15 million from Radical Ventures, Felicis, and prominent angels including Ali Gil, Sarah Guo, Scott Belsky, and Guillermo Rauch. Previously a research scientist at Meta's FAIR lab, Abhishek holds a PhD from Georgia Tech where he pioneered work on AI agents that can see, talk, and act starting in 2016.

In Today's Episode We Discuss:
00:53 - Why how we interact with the web hasn't changed in three decades and what will break that
02:27 - The coming shift from manual browsing to AI assistants performing tasks in the background
05:57 - What "agents" actually meant in ML research before the term became overloaded
06:14 - Why 90% accuracy per step creates catastrophic failure rates over multi-step workflows
08:46 - The behavior pattern humans nail intuitively that machines struggle with: backtracking from errors
10:11 - The DoorDash experiment: building an end-to-end food ordering agent that never shipped
12:58 - Why training on sinle websites leads to memorization instead of generalization
13:03 - The dopamine problem: some tasks users don't want automated
15:08 - Why capability-scoped beats website-scoped: the pivot to read-only horizontal agents
18:05 - Three criteria that drove the horizontal decision: research, user value, and data strategy
24:18 - Scouts API launch: why different channels have different risk appetites for web agents
26:30 - Flying close to the sun: how Yutori competes with hyperscalers on horizontal AI
30:32 - What VCs should actually test for in horizontal AI teams beyond founder horsepower
32:10 - Why three-month roadmaps are the only reasonable planning horizon in AI today
33:05 - The dogfooding ritual: every team member rotates through user feedback weekly
34:50 - Why research and product can't be siloed and how ideas flow both directions
36:03 - The uncomfortable truth: end users don't care about your research breakthroughs
37:32 - The Nintendo Switch 2 problem: aggregating individual feedback into systemic fixes
39:35 - Reframing web agents as "buyer's agents" that filter the internet on your behalf
40:59 - The simulation bet: training agents on cloned websites for high-stakes irreversible actions
43:05 - Why initial team skepticism about Scouts' value proposition was completely wrong
45:01 - How scout reports contextualize results with reasoning and ingest feedback over time
47:52 - The core insight test: where does your instinct lie across research, market, and domain?
49:36 - The hiring trap: why preemptively hiring sales leadership to impress VCs backfires
51:18 - The 12-year-old advice that still guides him: "Be a sponge when entering a new space"
53:05 - Non-negotiables: walking the dog with podcasts and personally reading every user email
54:49 - What founders actually need from VCs: direct and timely feedback, not just capital

Sumeru Chatterjee reveals the exact 10-week playbook he's used to generate millions of impressions at four unicorns, including why most B2B launches fail and how to weaponize your investor network for maximum impact. You'll discover why emotion beats logic in B2B marketing and why treating existing features as "new launches" is the growth hack nobody talks about.

Sumeru Chatterjee is Head of Growth at CoWorker AI, the first AI agent for complex work. Previously an early employee at four unicorns and founder of LaunchMob agency, Sumeru orchestrated CoWorker's launch that generated over 1 million impressions in a single day with 75 investors coordinated like a military operation.

In Today's Episode We Discuss:
03:45 - Mine 20 customer calls for launch gold using AI
07:29 - Stop hiring humans: Why fear sells better than features
10:23 - The 200 dream customers exercise founders skip
14:50 - Find 50 influencers who already own your audience
18:05 - Three distribution channels max or you'll fail everywhere
20:40 - Everyone claims differentiation but nobody actually commits
29:48 - The $20 book that made Hormozi $60 million
35:36 - Competitive positioning vs contextual positioning changes everything
38:28 - 46 creative concepts: From white papers to doormats
44:16 - Product Hunt is dead for B2B launches
54:05 - Coworker's investor spreadsheet that drove 1M impressions
01:08:44 - Launch every two weeks or become irrelevant
01:11:03 - OpenAI launches Slack integration like it's revolutionary
01:14:37 - Your 10 employees are connected to 500,000 people
01:15:37 - Different is better than better always wins
01:18:04 - Master one funnel before attempting anything else

In this episode, Pablo Palafox reveals exactly how to implement Palantir's FDE motion at a startup - including when to use it, who to hire, and the costly mistakes to avoid. Learn why embedding engineers directly with customers beats traditional sales approaches for complex AI products.

Pablo Palafox is the co-founder and CEO of Happy Robot, the AI-native operating system for supply chain and logistics. Prior to Happy Robot, Pablo completed his PhD in computer science and deep learning. Happy Robot has raised over $60M from investors including a16z, YC, and Base10, and serves enterprise customers like DHL.

In Today's Episode We Discuss:
02:01 - When the CEO realizes they're actually the company's first FDE
05:13 - Why embedding with customers beats having a sales pitch
09:01 - Stop trying to copy Palantir - build your own FDE playbook
13:25 - The critical difference between FDEs and deployment strategists
17:19 - How Discord servers led to billion-dollar freight broker clients
21:33 - FDEs must become industry insiders, not just tech experts
25:46 - When NOT to use the forward deployed engineer model
30:55 - The FDE hiring secret: Look for "nerds who can sell"
36:35 - Why FDEs need 1-2% equity vs 0.1-0.5% for regular engineers
41:49 - An FDE's day: 80% building, 20% with customers onsite
47:00 - The $30K to $3M expansion playbook for FDE accounts
52:10 - Building FDE "pods" for vertical specialization
56:27 - Why waiting to verticalize FDEs was their biggest mistake
59:19 - The 10X deployment accelerator most startups forget
62:00 - Why FDEs will soon build entire vertical products autonomously
64:58 - When to transition from "things that don't scale" to scale
67:11 - The one place every vertical AI founder must go immediately

Most founders think raising $100M means spending aggressively. Adit Abraham raised $108M and spent only $1M - while landing Fortune 10 contracts very early on and having experienced zero enterprise churn to date.

In this episode, he reveals the counterintuitive focus strategies that helped Reducto turn documents into data better than anyone else, including why they fired a $5K contract, limited engineers to one priority per week, and spent months recruiting a single PhD instead of scaling the team quickly.

Adit Abraham is the co-founder and CEO of Reducto, an AI company that transforms documents into structured data for language models. He previously worked at Google and attempted other startups before Reducto, where he learned the hard lessons about focus that now drive his company's success. Reducto has raised over $100M from A16Z, Benchmark, First Round Capital, and Y Combinator.

In Today's Episode We Discuss:
02:04 - Pivoting from a viral product before Y Combinator even began
05:48 - How free computer vision consulting revealed real product-market fit
07:29 - The exact moment founders know they've found product-market fit
08:03 - Why going one layer deep on ideas is the most dangerous founder trap
11:10 - Choosing two PDF features over 35 file types competitors supported
14:54 - Turning down construction document contracts worth millions in revenue
17:10 - Past startup failures that became the blueprint for saying no successfully
22:25 - Cutting engineer to-do lists from 10 items to 1 weekly priority
27:45 - The doctor-patient framework that makes rejecting customers feel collaborative
31:35 - Maintaining velocity while scaling from 4 to 20 high-agency employees
36:08 - Prioritization without spreadsheets: qualitative judgment over point systems
38:50 - Spending $1 million after raising $108 million from top-tier VCs
40:52 - Why their first research hire is one of 10 best in world for document AI
46:35 - The fitness trainer analogy every founder misunderstands about company building
49:14 - When "stay lean" advice becomes the wrong strategy for your stage
50:16 - Why full-time commitment creates space for different experiments than side projects
52:04 - The VC conversation that made sharing bad news feel safe instead of scary

PLG gets you in. Enterprise funds the future. They need vastly different products - how do you prioritize?

If you try to please both motions at once, you starve both.

How to balance PLG with enterprise is what I discuss with Feross Aboukhadijeh, the CEO and co-founder of Socket ($65M raised from a16z, Abstract, Dylan Field, Aaron Levie, and other).

Socket, a developer-first security platform protecting code from vulnerable and malicious dependencies. Before Socket, Feross was an open source maintainer and developer who built widely-used libraries.

In Today's Episode We Discuss:

01:43 - How developer background dictated Socket's PLG-first strategy over enterprise

04:50 - Building a GitHub app in 48 hours to avoid launching with zero user capture

07:56 - The counterintuitive rule: launch with intentionally missing enterprise features

10:53 - Why Socket deliberately ignored vulnerabilities despite every competitor offering it

11:20 - The dirty secret of startup pricing pages most founders won't admit

15:37 - How Socket mistakenly modeled pricing after GitHub's public/private repository strategy

16:08 - Why cryptocurrency companies exposed a fatal flaw in Socket's pricing model

18:19 - Going straight to enterprise sales to defend against fast-following competitors

19:37 - Why product quality loses to inferior products with superior go-to-market

21:36 - Socket's first enterprise deal was $500 and they kept doubling until pushback

24:27 - When PLG and enterprise roadmaps become zero-sum resource battles

26:27 - The strategic mistake of abandoning PLG motion after enterprise traction

28:54 - How developer awareness creates unfair advantages in security tool evaluations

29:23 - Enterprise handholding versus self-serve product design create opposing company muscles

33:01 - Figma's playbook: how connecting free-to-enterprise destroys customer acquisition costs

36:12 - The biggest regret: not building the PLG funnel before enterprise distraction hit

40:57 - Getting SOC 2 on day one would have parallelized six months of enterprise delays

41:00 - The monstrosity trap: second-time founders who hire VPs before product-market fit

40:13 - Why the popular advice to limit cap table size is fundamentally wrong

41:05 - Why Feross regrets turning away a $10K angel investment over ego

43:24 - The technical founder's fatal mistake: choosing to code over customer conversations

45:04 - Why selling before building feels wrong but saves months of wasted development

45:13 - The Mom Test: the book that teaches founders how to extract honest customer feedback

Today, we discuss how to build the right culture before the wrong one costs you millions.

Every founder thinks about culture, but almost none do it right.

Abhi Sharma, a second-time founder / now the founder and CEO of Relyance AI, learned this the hard way after reaching several million in ARR.

Things were breaking and he couldn’t pinpoint exactly why.

Now he shares the exact framework he uses to build culture that actually scales - from defining your company's "invariant" to implementing tactical excellence across every department.

Abhi Sharma is the co-founder and CEO of Relyance AI, a company building super intelligence for data security. To date, Relyance has raised over $60 million from top-tier investors including Menlo Ventures, Unusual Ventures, and Microsoft's M12 Venture Fund.

In Today's Episode We Discuss:
00:01:41 - Why culture always feels like an afterthought until systems break and you can't explain why
00:03:35 - The exponential dissipation problem: how founder control over culture disappears faster than you think
00:05:09 - Three catastrophic ways poor culture manifested at Relyance: hiring mistakes, product strategy disconnects, and enablement failures
00:09:59 - Why shouting culture values from the rooftops fails: the unreasonable hospitality pivot that actually worked
00:12:14 - The $X million ARR wake-up call: when Abhi realized he was getting hires wrong and had to define operating principles
00:15:25 - From weekend reflection to company DNA: the exact process of distilling culture down to actionable principles
00:17:11 - The one piece most founders iterate on after writing culture docs (and why examples matter more than principles)
00:20:21 - Your company's invariant: why every startup is ultimately about one core idea that never changes
00:23:56 - Stripe's GDP example: how the best companies anchor to fundamental human behaviors, not features
00:25:14 - The Hedgehog Concept decoded: three components that create your competitive moat (straight from Jim Collins)
00:28:06 - Data journeys as superpower: why Relyance's unique differentiator became their core product feature
00:30:08 - Economic driver vs. pricing: why most founders confuse the two and how it kills scalability
00:32:54 - Dominance friction: how misalignment between business model and customer value creates disruption vulnerability
00:33:28 - Costco's profit-per-square-foot model: the counterintuitive pricing strategy that drives more volume
00:37:30 - Why it took three years to figure out Relyance's economic driver (and why that's perfectly okay)
00:38:50 - Culture is actions, not words: why cultural values without operating blueprints are worthless
00:40:57 - The trust operating principle: Stockdale Paradox, job vs. responsibility, and good news fast vs. bad news faster
00:45:20 - How job versus responsibility transforms employees into owners (and why most companies fail at this)
00:47:23 - Why "you don't get credit for 80% to the moon" is the ultimate accountability framework
00:49:16 - Making escalation a good word: rewiring team psychology around bad news and urgency
00:51:41 - The belief system cherry on top: three statements that tie everything together and fit on a sticker
00:55:19 - Tactical excellence: why Control-C, Control-V matters more than inspiration (and how to operationalize culture daily)
00:58:20 - The monthly new hire ritual Abhi still does himself: why culture onboarding can never be delegated
00:59:49 - Founder mode vs. micromanagement: Brian Chesky was right, but where's the line?
01:01:22 - The X vs. X+Y million ARR question: why every growth gap traces back to cultural problems
01:03:26 - Popular bad advice: why "hire executives and step away" is wrong and when founder instinct trumps expertise
01:05:06 - The brutal honesty test: if you're not all-in, don't start a company (and why vanity startups fail 100% of the time)
01:06:16 - Reflection time as competitive advantage: how America's polymaths and founding fathers made progress through going inward
01:06:48 - The first five deals rule: why Abhi banned VC introductions for Relyance's initial customers (and why it was magical advice)
01:09:36 - Product-market fit vs. AI hype: are you hacking your way to ARR or truly iterating toward customer pain?

Why listen: Jacob Beckerman reveals why the cost of code approaching zero means every software company needs to rethink everything - from margins to moats to hiring. He's open-sourcing his entire codebase, hiring poets alongside engineers, and building for a world where brand matters more than features.

Jacob Beckerman is the founder and CEO of Macro, an AI workspace startup that has raised over $32 million from Andreessen Horowitz and Box Group. He previously conducted AI research at Penn and worked at Bridgewater Associates.

In Today's Episode We Discuss:
00:00 - Why everything you learned about building software companies is now obsolete
01:47 - The three radical changes coming as software development costs hit zero
05:47 - Why 93% gross margins are dead and cursor operates at 20%
08:28 - The new rulebook: ambition, openness, and brand over features
11:06 - Why being "principled" and narrow will kill your startup
13:11 - From seven-figure PDF reader to replacing Slack, Notion, and Linear simultaneously
17:19 - Open-sourcing your entire codebase as competitive advantage
20:50 - Why you're selling integrations and intelligence, not software
22:26 - Hiring poets and MFAs instead of MIT engineers
27:50 - Software brands becoming like fashion: Salesforce as Kirkland
30:34 - Traditional moats are dead—what actually matters now
32:32 - "Would you rather wrap a database or superintelligence?"
35:00 - Infinite demand for intelligence vs finite meeting summaries
40:00 - Why zombie unicorns have their heads in the sand about AGI
42:26 - Battle scars matter more than startup advice
47:22 - "Get the hell out of the way and let me go on my journey"

In this episode, Paul Russo, a sales leader at Pump unpacks a sales-hiring system built for aggressive, early-stage growth. You’ll hear how to source elite junior talent, pressure-test them with mock cold calls, and ramp them into technical AEs who still outbound hard. He also shares promotion gates, call quotas, and the culture required to chase incredibly ambitious goals.

Our guest Paul Russo is employee #1 and a sales leader at Pump.co, the company that helps startups save up to 60% on cloud costs - for free.

In Today’s Episode We Discuss:

05:09 - The “weird” target formula forcing 20% month-over-month revenue growth.

07:48 - Do individual-sport athletes outperform team players in enterprise sales?

09:10 - Outbound-first: hire technical AEs over “been-there enterprise” veterans.

11:22 - Why we prefer scientists over business majors for AWS selling.

11:43 - Recruit “future founders” and frame the role as founder school.

13:24 - Scale with hungry rookies led by seasoned pod leaders.

15:24 - YC Bookface + Top-20 schools: an elite sales-athlete pipeline.

20:02 - Cold-call candidates with traction—sell the unicorn vision first.

23:10 - COO screen routes talent; extroverts go sales, introverts to ops.

26:01 - Mock cold calls, no context: test grit, tone, coachability fast.

29:09 - Demand real conflict stories—“I never fight” is a red flag.

29:52 - Assess disciplined routines: 4:30am calls require athlete-like habits.

31:10 - Explain FinOps simply: reserved instances are leases, not compute.

35:39 - Cultural bar: 12–16-hour days, aiming for a 2028 IPO.

37:48 - Onboarding: Pump University, daily mocks, Nooks-powered 750-call days.

40:36 - Two-month ramp; PIPs are coaching tools, not pre-firing.

43:04 - Promotion ladders with hard gates; AEs still dial 250/day.

47:08 - Friendly pod rivalry + “rebuttal ball” spreads best practices.

53:41 - First sales hire playbook: top-school hunter, athlete, founder-aspiring—equity-heavy.

That’s why Paul Veugen challenges the conventional wisdom that marketing should wait until product-market fit, arguing that building your growth engine from day one is the only way to achieve predictable, scalable growth.

Paul Veugen is a serial entrepreneur and investor currently building Detail, a video creation platform that enables everyone to share their story faster. He previously founded and led Human to an acquisition by Mapbox, and Usabilla which sold to SurveyMonkey for $100 million in 2019. He also led product and go-to-market at Color, which has raised close to $500 million from top-tier investors.

In Today's Episode We Discuss:
02:01 - Why "don't invest in marketing until product-market fit" is terrible advice for founders
03:37 - How marketing experiments are actually customer discovery in disguise
07:26 - Why cold outbound is dead and founders need to build momentum before reaching out
13:27 - The brutal math: You need 20% month-over-month growth to hit $1M ARR in 12 months
19:05 - How to brute force your way to finding winning marketing channels
26:05 - Why marketing channels take 90+ days to show results (and most founders give up too soon)
34:13 - Overcoming the fear of looking stupid in public when building in public
40:58 - How positioning drives product decisions, not the other way around
47:44 - Why AI features are attention grabbers, not value drivers
49:18 - The messy middle: Why channels feel broken before they explode
55:05 - How being an investor makes you a better founder (and vice versa)
57:58 - The problem with MVPs and why testing individual ingredients is useless
01:02:23 - Why building a startup is an endless expedition, not a sprint

This episode tackles the uncomfortable line between being humane and looking out for employees while also being a high-performing organization - and what a real culture reset looks like when you’ve let it slip.

Our guest is Cat Noone who went through such a major reset herself with the company she co-founded, Stark - which is trusted by over 50,000+ companies and >$10M raised from Uncork and us at focal.

In Today's Episode We Discuss:
01:46 - How being hell-bent on mission while avoiding "bro culture" backfired
03:54 - The early warning signs that performance was drifting at Stark
04:14 - Why I stopped doing reference checks and paid the price
08:38 - How the lowest performer sets your company's bar, not the best
09:17 - When busy work replaces real productivity in remote teams
12:32 - You can't have shitty input AND shitty output - pick one
15:01 - Why founder insecurity about being "employee friendly" kills companies
18:28 - The brutal emotional cost of firing people you've worked with from day one
25:00 - How to communicate layoffs to survivors and rebuild momentum
29:39 - Why urgency beats speed for maintaining quality standards
33:38 - Demo Thursdays as quality control checkpoints, not show and tell
37:06 - The four-day work week experiment and why Fridays aren't free
40:01 - Why most startup principles are worthless wallpaper
44:12 - If you're going to cut deep, cut deeper - don't play it safe
45:58 - Move fast and break things is an excuse to ship shit
48:34 - Get an executive coach before you think you need one

This episode dives in on how to decouple a north‑star company vision from a scrappy, testable product pitch that customers can adopt today. You’ll learn how to use positioning as your lever - choose sharper category language, cut scope to true table stakes, and listen for unsolicited buy signals- to move from zero traction to real pull. 

On top, you’ll learn what the slowest, costliest way to validate an idea is; how to identify table stakes; and the signals that tell you when to broaden your ICP. 

In Today’s Episode We Discuss:

• 01:35 - From “Stripe for Support” to reality: what we missed
• 03:48 - API‑first exposes every seam; validation speed plummets
• 07:59 - The worst enterprise pitch: “engineers, please write more code”
• 11:23 - Name your category—or wear Zendesk/Intercom’s handcuffs
• 16:06 - Set true table stakes; timebox the MVP ruthlessly
• 21:02 - Buy‑now signals: users volunteer payment without a hard sell
• 23:49 - Ethical pre‑selling: describe the future, then sprint to it
• 25:12 - Turn case studies into copy—speak customers’ exact language
• 27:38 - Vertical → use case → market: DevTools → Technical Support → B2B
• 30:54 - Outrun feature spreadsheets with a customer collaboration thesis
• 40:41 - What collaboration means: Slack escalations, issue trackers, shared context
• 47:15 - Map features to FRT, CSAT, retention—not “shiny UI” claims
• 50:34 - Homepage discipline: kill vanity metrics and shortcut bragging
• 52:21 - 70/30 rule: discovery + founder conviction against higher‑order shifts

This episode is a tactical masterclass on early-stage B2B sales. You’ll learn how to nail the first meeting, architect modular demos, multi‑thread like a pro, and turn proposals into “Champion Empowerment” decks that actually close. We also cover ROI modeling, executive sponsorship, outbound strategy, and the exact behaviors that separate A‑players from everyone else.

Our guest is Greg Costigan leads the sales team at Performica and has built and led GTM organizations at Box, Zuora, Zenefits, LearnUp, Hone, and MindGym. He’s closed complex enterprise deals, championed award‑winning programs (e.g., Pinterest’s Brandon Hall–recognized L&D initiative), and specializes in taking startups from founder‑led sales to scalable processes.

In Today’s Episode We Discuss:
01:33 - Sales process is a science—ditch gut feel for repeatable rigor.
04:51 - Stop skipping steps—credibility beats the ‘one‑call close’ myth.
07:01 - First meeting playbook: GGGA, pre-read, ruthless prep.
10:57 - Lead with a hypothesis—change the buyer’s frame (Challenger).
13:32 - First-call exceptionalism: come in hot and create momentum.
14:51 - Yes, demo on call one—and land a clean close.
19:44 - Multi-thread fast: champion texting, exec sponsors, rule of threes.
22:19 - Demo excellence: send agenda early, close BANT/MEDDICC gaps.
23:59 - Modular demos: tailor admin, user, integrations to stakeholders.
27:51 - End every demo with a scoping or proposal—never ambiguity.
34:14 - Turn proposals into a Champion Empowerment deck that sells itself.
36:54 - No exec sponsor? You’re at risk—fix it before forecasting.
38:20 - Build a simple ROI model—finance will ask, be ready.
54:49 - Outbound isn’t dead—SDRs matter more than ever.

When should a startup go from SMB to enterprise - and when should you not?

I break this down with a former revenue leader at Box, SurveyMonkey, Asana, etc - Matt Harmon (ex‑Box, Asana, SurveyMonkey). We discuss the real signals for enterprise readiness, why security/compliance readiness matters, and why “we’ll build it if you buy it” kills confidence. We also compare playbooks for existing vs. new categories, the land→expand reality, and how to balance self‑serve revenue with enterprise ambitions.

In Today's Episode We Discuss:
1:42 Why the “go upmarket” conversation starts early
4:53 Company readiness: security, compliance, SEs, forecasting shifts
10:57 Signals it’s curiosity-only vs. a real enterprise opportunity
16:45 “Is it someone’s KPI?” and the need for true pain/need
18:36 Existing category = one path to buy (ripping/replacing)
22:52 New category upmarket: shared services & proving uniqueness
28:28 Land→expand and product-led reality
33:08 Don’t force a model—map the customer journey first
37:57 Positioning and intellectual honesty at ~$1M ARR
40:00 Category creation vs. innovating in an existing one
45:07 Why not to fear SMB/self-serve revenue
47:15 Don’t over-index on “sell to pain” for new categories
50:15 Founder advice: embrace ambiguity and EQ
52:25 What great VCs do: back leaders who can hire leaders

This episode is a masterclass in founder decision-making: choosing (and parting with) co-founders, bootstrapping to real revenue, then raising at scale - without losing the plot. Expect frank takes on titles, burn, investor selection, and the moral weight of taking other people’s money.

Duncan Weatherston is the co-founder and CEO of Smile Digital Health, a leading healthcare data platform company. He and his team bootstrapped to ~$10M ARR before raising a $20M Series A, and are now well past $50M in ARR.

01:40 - Why start with co-founders vs going solo in healthcare SaaS
06:27 - How to vet co-founders: proof of execution over chemistry
06:58 - The #1 mistake: trusting claims without validating capability
09:39 - Early-stage stars rarely scale—how roles must evolve
12:25 - Title inflation trap: why early VP labels backfire later
12:47 - Be mercenary with misfits: fairness to the team > feelings
16:56 - Create IC ladders: don’t “promote” top engineers into management
18:27 - Founder vesting: avoid dead equity with 5–6 year schedules
19:46 - Why they bootstrapped first: expertise, low burn, paying customers
22:40 - Would he raise earlier today? Services-led product tradeoffs
25:47 - The $20M decision: buyouts, tailwinds, and scaling delivery
34:04 - Taking VC creates a moral obligation—here’s what that means
36:56 - 2021 mistake: “spend aggressively” and adapting too slowly
45:59 - The do-over: fix org design, roles, and accountability sooner
46:25 - Popular advice he rejects: don’t contort your playbook to fads
48:41 - PMF obsession: identify your repeatable sales unit before scaling
51:03 - Best investor advice: hire actual A-players, not just roles

Basile Senesi is the Chief Revenue Officer at Arc, the financial operating system for growth companies. He's built multiple YC companies including Phonebox (raised $500M+), is a prolific angel investor, and owns Chateau Pavo winery in Sonoma.

In Today's Episode We Discuss:
02:17 - How Arc originated $100M in loans then killed the product
07:25 - The warning signs that made them abandon massive revenue growth
10:49 - Why unit economics matter more than investor expectations
14:16 - How to convince investors to kill your fastest-growing product
16:38 - Pivoting from lending to cash management during market chaos
19:05 - Why do the hard thing first in fintech
22:14 - Everything is a funnel: validating ideas without building
27:34 - Building operating models before you have revenue
34:50 - Why startups need pessimistic salespeople
37:00 - How to know when you're building the wrong business
40:14 - Not all revenue is created equal in venture
43:11 - Hire for the long haul, not the next milestone
46:54 - Tactics equal strategy in early-stage startups
50:49 - Learning what not to do is your competitive advantage

This episode goes through the exact playbook the former BCG consultant and private equity investor used to de-risk his leap into entrepreneurship - including his 3-point checklist that allowed him to say no to Apollo. Don shares hard-won lessons about finding product-market fit, recruiting world-class talent, and why it took 190 rejections to get to his first 10 customers.

Don Muir is the co-founder and CEO of Arc, a zero-asset commercial bank powered by AI that offers intelligent capital management and private credit to ambitious businesses. To date, Arc has raised over $180M in debt and equity.

In Today's Episode We Discuss:
01:30 - Why I chose debt over equity and existing markets over new ones
04:10 - The bottoms-up approach to finding your unique right to win
08:44 - From crowdfunding communities to non-dilutive capital: 4 pivots to product-market fit
11:42 - Execution over innovation: Why first-time founders shouldn't reinvent the wheel
14:14 - The 3-point checklist before rejecting Apollo's offer
16:26 - Getting 10 CEO signatures with just a Stanford email address
21:49 - 190 rejections, then 10 straight wins: The LOI breakthrough moment
23:29 - Finding fast-moving waters: When to pivot vs. persevere
25:28 - The Stanford.edu email hack that opened CEO doors
32:25 - Why technical co-founder pedigree is overrated (but VCs disagree)
38:07 - How one $100k check turned hundreds of "no's" into "yes's"
42:32 - The sleepless nights that forced the Apollo phone call
45:59 - When your biggest rejection becomes your largest partner
49:41 - Why the "safe path" is actually the riskiest choice
52:55 - The venture capital myth: Why most startups don't need VC money

Anis Bennaceur is the co-founder and CEO of Attention, a startup building AI agents that revolutionize sales conversations. A second-time founder, Attention has raised close to $20 million from Eniac, 645 Ventures, Liquid2 Ventures, and Alvin.

In Today's Episode We Discuss:
01:25 - The Triangle of Talent: Why 80% of your employees are useless
04:26 - Level 5 superstars can't be trained - they're born that way
05:43 - Your first hires must think like founders or you'll fail
10:25 - Why Anis only hires people obsessed with Paul Graham essays
15:58 - The $100K hiring mistake that saved Attention's culture
18:35 - Two sales candidates talked each other out of joining - here's why
21:40 - Always hire salespeople in pairs to create internal competition
25:34 - The midnight email test that reveals true A-players
27:56 - One interview question that exposes scrappy hackers instantly
31:23 - Using ChatGPT to detect hiring red flags you missed
35:02 - Three biggest life failures: The therapist interview technique
41:42 - Why Brian Chesky's anti-selling method filters out mercenaries
54:54 - The Saturday night Slack test that predicted employee turnover
56:52 - How political extremism kills startup culture
58:25 - "If you had the contract, why wouldn't you sign?"
1:05:15 - Rejecting candidates who negotiate reveals commitment issues
1:12:13 - Stop listening to customers - they'll build you a faster horse

If you’re thinking about hiring your first sellers - or wondering why the ones you hired are struggling to hit their numbers - this one is for you!

In this week’s focal podcast, I unpack in detail how to build a repeatable sales playbook that actually works with Russ Thau who drops the sales productivity formula he used to scale multiple companies past $50M in revenue, including taking Box, Intercom, Envoy, SuccessFactor, Airtable, and Launch Darkly.

In Today's Episode We Discuss:
02:09 - Why time is the one thing you can't fabricate in sales
03:43 - How many calls can someone realistically take per day?
03:53 - The control experiment: Why founders should do calls first
06:22 - First calls vs. follow-ups: How to benchmark properly
07:46 - Why reps need 30 minutes prep time per call
09:39 - The critical 5-minute buffer between calls
09:49 - How call complexity changes everything (Intercom vs. SuccessFactors)
11:55 - Why follow-ups must happen within hours, not days
12:07 - The context switch problem with outbound prospecting
14:24 - How long founders need to keep selling alongside reps
14:56 - Why hire two AEs at once, not just one
17:22 - The 90-day signal that reveals rep quality
19:04 - When to hire your first sales leader (3-4 AEs)
21:26 - The biggest mistake: Forgetting reps are human beings
22:31 - Why 10% conversion rate is your absolute minimum
24:46 - The velocity math: 100 calls to close 10 deals
26:02 - How conversion rates reveal your true ideal customer
28:20 - The $10-30K deal size "no man's land"
33:00 - Why companies set $36K minimum deal sizes (the math revealed)
37:19 - How to escape no man's land and sell bigger deals
43:07 - Enterprise vs. velocity rep skills: What's the difference?
45:04 - Understanding "the real deal" and your sales methodology
48:55 - Why sales productivity is simpler than you think

If you keep doing what you were doing to get to $1M ARR, you won’t get to $3M ARR. What got you to $3M won’t get you to $10M, what got you to $10M won’t get you to $20M, and so on. The hard truth about rocket ship startup growth is that you have to reinvent yourself at every major revenue milestone you reach. But unfortunately, most founders can't do it. They cling to what worked, scale what's broken, and wonder why growth stalls.

In this episode, I sit down with Russ Thau, a former founder and seasoned revenue leader specializing in scaling companies from $1M to $50M in revenue, to discuss what you have to do when on the Sales side to reach $50M+ in revenue as fast as possible.

Russ has has scaled revenue from single digit millions to $150M+ and two IPOs at companies such as Intercom, Box,  and Envoy, and he's also advised companies like Airtable and LaunchDarkly since they were sub-$1M in revenue.

In Today's Episode We Discuss:
02:02 - Why being a good salesperson is actually bad for getting to $1M revenue
04:31 - The counterintuitive shift from "do everything" to "go extremely narrow" at $1M
07:34 - How to identify role model customers that create herd momentum
11:16 - The dangerous TAM trap: why you DON'T need a billion-dollar market early on
16:48 - When to stop narrowing and start widening your ICP at $3M+
20:33 - The "premature scaling" mistake that kills momentum at $3M
27:54 - Why the bowling pin strategy beats boiling the ocean from $3M to $10M
32:01 - When "good chaos" signals it's time to implement real processes
38:22 - The 5 critical metrics every revenue leader needs at $10M
44:08 - How Box bet the entire company on enterprise at $20M (and won)
50:52 - The 3 types of startup employees - and why nobody spans all three
54:08 - Where to find entrepreneurial salespeople (hint: failed startups)
1:01:08 - When to start "sprinkling in" process-oriented people vs entrepreneurs
1:04:59 - The founder-to-sales-leader handoff: optimal timing and structure
1:11:30 - Why agility beats everything else in startup revenue growth

Get insights into the counterintuitive playbook that defies conventional wisdom about when startups should pursue partnerships with Natasha Ratanshi-Stein, Founder and CEO Surfboard, who nailed partnerships as their main GTM channel almost from Day 1 and eventually generated 55% of revenue through partners.

Surfboard is a workforce management platform for customer service teams. After raising a $5 million seed round in 2022, they successfully exited to Dialpad in 2024 - a company they started engaging with as a partner first.

In Today's Episode We Discuss:
01:17 - Why partnerships before customers isn't crazy
02:20 - Which partners actually move the needle for early startups?
04:55 - How to convince big partners when you have zero revenue
08:20 - The exact story framework that opens partnership doors
10:17 - From informal to 20% revenue share: partnership evolution
13:37 - Critical enablement mistakes that kill partnerships
19:38 - Running partnership meetings that actually drive revenue
21:41 - Do your partners even watch your enablement videos?
22:39 - The Series B to pre-IPO partnership sweet spot
27:17 - Early signals a partnership will fail
29:31 - Negotiating partnership agreements: what founders miss
33:53 - Why paying marketplace listing fees is usually worthless
37:38 - When partnerships generated 55% of total revenue
39:40 - The hidden partnership integration tax nobody discusses
40:30 - Launching 20 partnerships, 5 worked
43:29 - The dangerous 20% rule for partnership dependency
45:21 - When Zendesk bought our competitor: partnership nightmare
52:18 - The one hiring mistake every founder makes

A lot is written about the $0 to $1M ARR journey. A lot less about the $1M to $10M journey - even though that’s where lots of promising companies die. Most of what it takes to get to $10M ARR follows established patterns. Yet, too many startups try to reinvent the wheel and die as a consequence.

In this episode, Guillaume Jacquet walks us through the steps you have to take as a founder as you move from founder-led sales to a predictable revenue engine. Learn why 80% of scaling from $1M to $10M is science, not magic, and discover the counterintuitive hiring sequence that most founders get wrong.

Guillaume Jacquet is Co-founder and CEO of Vasco, the revenue architecture platform for VC-backed startups to maximize go-to-market efficiency. He's built and scaled multiple B2B companies through the critical $1M-$10M journey and codified the repeatable systems that work.

In Today's Episode We Discuss:
00:00 - Why building $100M starts with forgetting about $100M
01:17 - The founder magic trap that kills growth at $1M ARR
03:13 - How to surgically narrow your ICP when everyone says go broader
05:49 - Why your best customers move from purchase to value fastest
10:16 - The impossible metrics problem when salespeople do everything
13:18 - Mapping the real B2B customer journey most founders ignore
15:05 - Why customer success must be your first hire (not sales)
17:48 - The counterintuitive order for removing yourself from revenue
20:01 - When predictable pipeline generation solves everything
22:24 - Why full-stack sales reps destroy accountability and growth
24:31 - How your ICP dictates your entire go-to-market motion
32:31 - The exact close rate benchmarks that signal go-to-market fit
37:26 - When to split implementation from retention for velocity
39:17 - Why expansion specialists unlock 140% net revenue retention
42:16 - The two paths from $10M to $50M (and why most choose wrong)
44:48 - The 18-month hiring mistake that killed his first company

Learn why most startups do customer discovery so poorly, why they fail at design partnerships and how Pocus CEO Alexa Grabell cracked the code by embracing skeptics over enthusiasts. Learn the counterintuitive approach that led to building a category-defining product in the crowded sales tech space.

Alexa Grabell is co-founder and CEO of Pocus, a revenue acceleration platform that helps go-to-market teams at companies like Asana, Canva, and Amiiro save 10+ hours weekly by turning data into pipeline. She's raised over $23M from First Round Capital, Coatue, Pear, and angels including Scott Belsky and Lenny Rachitsky.

In Today's Episode We Discuss:
01:46 - How to structure discovery calls to validate hypotheses in 2-3 week sprints
03:12 - The art of sending hundreds of LinkedIn messages to get 10 meetings per week
06:27 - Why leading with curiosity beats leading the witness in customer interviews
08:33 - How pretending to be a competitor's sales rep validates product ideas
10:52 - Converting skeptical prospects into your best design partners
13:49 - The #1 mistake that kills the transition from design partner to paying customer
15:09 - Why charging $6K when you should charge $30K destroys early retention
18:44 - How a founder learns enterprise sales by failing at every step
22:26 - Why early churn from wrong-fit customers is a feature, not a bug
24:14 - Using design partnerships again after raising Series A for AI products
28:05 - The power of building with skeptics who think AI can't solve their problems
33:12 - How to navigate pricing conversations when you don't know your price
35:02 - Why design partnerships require 70% of founder time to succeed
37:27 - Building a 4,000-person Slack community through valuable AMAs
41:20 - The contrarian approach to hiring marketing as your first GTM hire
42:20 - Why the best startup advice is to ignore all startup advice

Han Wang, Co-Founder and CEO of Mintlify, knows pivoting better than pretty much anyone. Mintlify pivoted 8 times during their first 14 months before finding Product-Market-Fit and eventually raising > $20M from a16z, Bain Capital Ventures, and YC.

While those 14 months felt like “chewing on glass”, Han learned a lot of valuable lessons he shared with me during our conversation, including why to bet on a space you care about, not a specific idea, if, when, and how to pivot, and why speed is your only advantage

In Today's Episode We Discuss:
00:00 - You really don't know what the market wants
01:24 - Why build for an idea space, not a specific idea
03:28 - Waking up and realizing you don't care about your customers
06:32 - The 8 pivots that led to Mintlify
10:24 - Figstack: 5,000 users on day one, then complete failure
13:55 - Pivoting 3 days before the YC interview
17:26 - Retention is everything - virality means nothing
26:45 - Building Mintlify over a weekend out of desperation
31:33 - When you're embarrassed to use your own product
34:07 - Ship fast or die - the real MVP mindset
36:51 - How to know when to pivot vs persist
40:00 - 14 months of chewing glass before success
45:36 - How to recognize product-market fit in one week
49:05 - Launching without an edit button and still closing sales
53:04 - Why falling in love with ideas kills startups
55:07 - Throw 100 darts fast vs calculating 2 perfect throws

Our guest, Santiago Suárez Ordóñez reveals how he went from zero sales experience to closing over 100 customers by treating revenue—not compliments—as the only signal that matters. This episode breaks down the exact playbook for transitioning from "advice calls" to actual sales.

Santiago Suárez Ordóñez is the CEO and co-founder of Momentum, an AI platform that transforms customer conversations into valuable go-to-market data (raised over $18M from Basis Set, First Mark, and others). Previously, he co-founded Blameless (raised $50M+) and was the first engineering hire at Sauce Labs (raised $150M+).

In Today's Episode We Discuss:
01:59 - Why Engineers Make Terrible Salespeople (Until They Don't)
04:40 - From 70+ Rejections to Finding The First Few Customers
07:25 - Stop Being the Smartest Person in the Room
09:40 - Why Your Friends Are Lying to You About Your Startup Idea
14:36 - It Takes 100 Meetings to Land 3 Design Partners
16:16 - Embracing Rejection: The Founder's Identity Crisis
19:11 - The Mom Test: How to Get Brutal Honest Feedback
22:44 - When Your Biggest Customer Is Your Worst Signal
26:13 - Money Is King: The Only Validation Metric That Matters
28:45 - From "Can I Get Your Advice?" to "Give Me Your Money"
37:12 - The Fellow Portfolio Company Email Hack That Opens Doors
41:12 - Never Demo First: The 30-Minute Sales Call Framework
44:58 - Why You Need SDRs Before Product-Market Fit
47:50 - Building a Sales Machine While Still Figuring Out What to Sell
54:54 - Shadow Your Customer for Free Instead of Building in Isolation
57:22 - Why Zero to $1M Is a Vanity Metric for Startups

In Today's Episode We Discuss:

01:30 - Why experimentation culture, not strategy, is the real growth secret at billion-dollar startups

03:32 - How running 100+ quarterly experiments creates massive competitive advantage—even with 70% failure rate

04:48 - Why your multi-week engineering sprints are killing growth—scope experiments to hours, not weeks

06:28 - Traditional growth channels beat moonshot virality—forget going viral, here's what actually works

09:00 - Why all your growth knowledge becomes useless when starting from zero revenue

12:28 - The exact customer threshold when traditional growth strategies finally start working

14:14 - Most companies kill experiments too early—why "this doesn't work" is your biggest growth obstacle

16:57 - What HubSpot's early growth tactics reveal about the counterintuitive power of partnerships

24:51 - The mathematical formula for prioritizing growth experiments nobody talks about

31:14 - Why most growth teams waste 90% of their time on the wrong activities

34:52 - How acting on website signals within 15 minutes can dramatically increase conversion rates

41:01 - Why growth hires—not engineers—will be the most crucial startup hires in coming years

42:28 - The costly mistake Austin would fix if restarting Unify: investing in growth 6 months earlier

45:16 - The surprising truth about what makes social media posts go viral for founders

48:19 - Why hiring growth talent from consulting and banking beats traditional marketing backgrounds

51:06 - The dangerous myth that you should perfect your product before selling it