The forward deployed engineer model took Happy Robot from zero to millions in revenue in under 2 years.
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
Why saying "no" is the secret to growing faster as a startup founder
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
Every bottom-up PLG company faces this tension:
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
Most startup founders discover they have a culture problem when things are already breaking
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?
The software industry's 30-year business model is becoming obsolete - this founder is betting his company on what comes next.
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"
Pump.co is one of the fastest growing YC companies. They got there partially by building an incredible sales team, stacked with talent that was overlooked by many.
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.
Most founders wait too long to invest in marketing—and by the time they realize their mistake, they've already lost the race.
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
If you don’t enforce the bar, you lower it.
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
Stop pitching the end state. Sell the smallest step that proves you can provide value.
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:
You have to be so much better than the incumbent if you want to have even the slightest change.
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.
Moving upmarket, the right way
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
Bootstrapping to $10M ARR was easier than raising the first $20M.
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
When every YC batchmate wanted their product and investors threw money at them, Arc made the unthinkable decision - abandon the business. Learn the framework for identifying false product-market fit that saved Arc from the fate of their now-struggling competitors.
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
Don Muir turned down his dream job at Apollo to build the AI-powered bank Arc.
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
In this episode, we dive deep into startup sales hiring with Anis Bennaceur, a masterful talent scout who's cracked the code on building exceptional early-stage teams. You'll discover why most founders hire wrong, how to spot founder-DNA in candidates, and the brutal interview techniques that filter out B-players before they contaminate your culture.
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
Most founders get sales rep productivity wrong - and it kills their growth.
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
What got you here won't get you there - the brutal truth about scaling from $1M to $50M in revenue.
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
How to nail partnerships from Day 1
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
Most startups die between $1M-$10M ARR because they try to reinvent the wheel.
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
From cold LinkedIn DMs to nailing customer discovery and design partnerships to eventually raising $23M from Tier 1 venture firms.
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