Episodes
245 episodes, by the week they came out · page 1 of 11
Week of 5 October 2026 11 Read the briefing
Why Risk Takers Build the Most with Doug Holladay, Author of Rethinking Success
In a study of 81 high school valedictorians followed for 14 years, students who played it safe by conforming and chasing grades and test scores rarely became standouts in their fields.
SPOTLIGHT: How CEO Sam Jacobs Is Redefining Pavilion's Identity | Sam Jacobs, Founder & CEO @ Pavilion
Removing the qualification barrier and letting anyone sign up online was the single biggest mistake Pavilion made.
How To Take Big Brand Swings (like NASCAR, Indy 500 and SXSW) with R. Ethan Braden, CMO of Texas A&M University
Braden rejects the blanket rule that a new CMO shouldn't redo the brand: it depends on whether a working platform already exists.
#615: How to Master Social Selling on LinkedIn to Book Meetings | Kade Hinkle | 30MPC Hall of Fame
Sending 30 LinkedIn connection requests a day to ICP prospects yields at least five acceptances for Kade Hinkle, selling to go-to-market leaders.
20VC: Cognition vs Factory: Vinod Khosla Creates a Storm | OpenAI Nears $70B Run Rate: Anthropic Under Threat | ElevenLabs Doubles Its Valuation to $22B & Salesforce Buys Listen Labs for $2B
OpenAI's reported Q3 growth would be a sharp re-acceleration after it slowed to roughly 18% quarter-on-quarter in Q2.
"We Will Die": Why QuotaPath Is Betting Everything on AI-Native Services ft. AJ Bruno (QuotaPath)
Product-led growth failed for commissions software because the data is sensitive and reps, CROs and RevOps are too disconnected for bottom-up adoption to travel upward.
#614: How to Use LinkedIn Sales Navigator for Lead Generation
Set an alert for net-new executives joining your own company, connect with them, then compare their network against your territory for introductions.
Is Your Business Healthy? Your Pricing May Have the Answer with John Gilbo
Gilbo makes pricing ROI credible by presenting a range and a break-even hurdle instead of leading with his biggest ROI number.
How to Get 10X More Traffic From Content You Already Have (with Ross Simmonds, Foundation Marketing)
Ross Simmonds lays out a multi-channel, repeated distribution sequence for a single good blog post.
20VC: Is Seed Investing Dead Without a $1BN Fund? | Does Ownership and Price Matter When Companies Can Be $1TRN Exits | Are AI Revenue Numbers Real and What to Watch Out For with Venky Ganesan, Menlo Ventures
Large funds, Menlo included, are somewhat indifferent to seed valuations because they treat seed checks as the price of a seat for later, larger investment.
How Vercel Is Rethinking Go-to-Market With AI | COO Jeanne Grosser
Vercel has raised sales quotas every six months, lifting capacity per rep instead of adding heads for each new increment of revenue.
Week of 28 September 2026 13 Read the briefing
Turning AI Tokens Into ROI (That You Can Measure) | CEO @ Paid, Manny Medina
Pricing agent work instead of seats removes the renewal contraction that happens when only a fraction of purchased seats are heavily used.
20VC: The Future of Datacentres: What You Need to Know | Why Everyone Gets GPU Depreciation and AI's Energy Costs Wrong | Who Really Makes Money From AI & Why Most Moats Don't Exist with Chase Lochmiller
Bitcoin miners cut about 98% of data centre cost by dropping reliability requirements, and Crusoe expected AI data centres to go through a similar redesign.
The Future of Outbound Prospecting in the AI Era
Nooks hired its first two sales reps at the same time rather than one at a time
Dave & Dasha Live from Drive: Beating Brain Rot, Burnout, and Boredom After 15 Years in B2B
Feedback works better when it points to concrete examples than when the manager rewrites the draft.
Why Deals Don't Close: Anne Gary's Framework for Discovery, Champions & Economic Buyers
Rushing discovery can leave buyers unwilling to share the metrics needed for a value case.
SPOTLIGHT: The Problem With Your CRM Nobody Talks About | Ramin Heydari, CEO & President @ XYZies
AI's pace makes 10% annual growth targets outdated and that businesses should aim for 10x growth.
#613: Master Parallel Selling Strategies to Speed Up Every Deal | Sam Mckenna | 30MPC Hall of Fame
When a champion is taking a deal to the board, find out whether they will present options, ask for permission or tell the board their decision, because each means a different path for the deal.
20VC: Instinct Raises $1B at $10B Valuation | AMD Buys Fei-Fei Li's World Labs for $8.2B | Meta Poaches MongoDB's CEO | Bessemer Raises $5.75B | Oura Pulls IPO & Nubank Eyes $8–12B Monzo Takeover
Benchmark treated its $10B Instinct investment as an early-stage bet, because the company is days old even though the price looks like growth.
Can AI Really Manage Your Entire Renewal Book? ft. Grant Clarke (Gainsight))
Gainsight Atlas charges for a managed renewal outcome rather than for software, combining AI agents and human renewal managers to run a client's renewal book.
#612: Sales Kickoff Masterclass: The Ultimate Planning Guide
Kayde Givens picks a kickoff theme from one of four situations (product changing, sales motion changing, not winning, winning) and gave a past example for each.
Is the MQL dead? (with Freya Ward, Headley Media)
The MQL's bad reputation comes mainly from how the term is framed, not from the tactic itself.
How to Raise Prices When Everything Is Getting More Expensive with Jacob Moller Korsgaard
Jacob personally favours an agreed pricing calendar with a fixed number of increase slots per year over reacting every time costs move.
20VC: $1BN ARR in 18 Months; The Untold Story of Higgsfield | Spending $4M Per Month on Models | Why Moats in AI are BS | Scaling a Content Team to 150 People with Alex Mashrabov
Higgsfield calculates annualized revenue as the last four weeks of live revenue multiplied by 13, pro-rating annual contracts and excluding multi-year deals.
Week of 21 September 2026 5 Read the briefing
If the AI Money Dries Up, Which Companies Burn?
Scaling AI companies averaged roughly 41% gross margins in 2024 and 45% in 2025, with a projected 52% in 2026; application-layer companies ran lower at 33%, 38% and a projected 45%.
Why Your Reps Leave SKOs No Better Equipped to Sell with John McMahon and John Kaplan
Build the SKO around what a rep should do differently on Monday, based on where the CRO sees reps getting stalled in deals.
Notion's Outcomes Architects on Why Today's CSMs Are Builders
Notion consolidated nine sales teams into roughly four functions, replacing solutions engineers with technical-builder solutions consultants and treating 'post-sales' as obsolete.
Why AI Gets Pricing Wrong and How to Train It to Get Pricing Right with Roberto Rivera
Escalation clauses in signed contracts, such as fuel-linked freight charges, are often forgotten, leaving margin unrecovered.
Inside the AI Startup Making Customer Support 65% Cheaper
Decagon added bar-raiser interviews at the end of its hiring process to keep the bar high while scaling, and most candidates pass them.
Week of 14 September 2026 4 Read the briefing
CRM As A Business World Model: The Future For GTM Teams? | Keith Peiris, CEO @ Lightfield
Lightfield uses its low-cost PLG plan as a lead-generation tool and upgrades customers from a $2K/year plan to a $24K/year plan once they hit product-market fit.
Why Proprietary Data Beats AI Software for 2x Pipeline Growth with Ann Davis
Telling reps which companies to pursue and which to avoid, using private-market data, is claimed to drive 2x pipeline growth in six months and 25% top-line growth in the same period.
SPOTLIGHT: What It Takes to Step into the CEO Role | Eric Anderson, CEO @ Walnut
If you want to attack enterprise, question whether you should also sell to SMB, because they need different product strategies and go-to-market approaches.
Owning Retention & Standardizing CS Across 17 Acquisitions ft. Rebecca Nerad (Advantive)
Acquired legacy software companies often have handshake deals and poorly documented contracts, so CS re-papers customers onto the acquirer's contracts.
Week of 7 September 2026 6 Read the briefing
RevOps for Hypergrowth (Fireworks AI, Perplexity, Exa & More) | CEO @ Go Nimbly, Jen Igartua
Jen Igartua's qualification bar for a RevOps engagement is roughly 20 reps plus a leader committed to building operations.
Recruiting the Right People and Selling Real Differentiation with Brad Scott, VP of Worldwide Sales at Glean
Leave space at the end of an interview for the candidate to ask questions, because weak candidates ask one or two and then say they are good.
SPOTLIGHT: Skipping the SMB Trap and Building for Big Brands | Matt Allison, CEO & Founder @ Handraise
At TrendKite, the smallest accounts churned heavily while the $30K+ tier retained best in class.
Stop Asking "Would You Renew?" Ask This Instead ft. Bob London
Introduce the big-picture part of a call by framing it as a 'step back' you take with your most successful customers; London says customers almost never refuse.
The Only Sales Role That Will Exist in 2030 w/ Christopher O'Donnell (Founder, Day AI)
Mark Roberge is encouraging companies to drop the SDR, AM and CS roles in favour of one role, without cutting the people in them.
The AI Race Has a Leaderboard | Arena CEO Anastasios Angelopoulos
API revenue at model labs may be far less sticky than the market assumes, because customers spending heavily can switch vendors when a cheaper model arrives.
Week of 31 August 2026 5 Read the briefing
Forget Growth. Your Valuation Depends On Your AI Story | Tomasz Tunguz, GP @ Theory Ventures
Investors reward a credible AI revenue story before revenue shows up, so an existing business needs to show it can sell tokens.
Strategy That Teams Actually Execute with Dr. Chuck Bamford
Build the competitor list from bump competitors and proxies, and keep it to five or six companies.
SPOTLIGHT: Surviving the Inbox Apocalypse | Evan Huck, CEO & Co-Founder @ UserEvidence
After eight quarters flat at about 150 opportunities per quarter despite rising brand investment, UserEvidence's pipeline reached 450 per quarter within two quarters.
80% of VP Roles Are Never Posted. Here's How to Find Them ft. Andy Mowat (Whispered)
Andy estimates that 75 to 80% of director-level roles are posted publicly, but only about 20% of VP roles and virtually no C-level roles are.
E74: Your Agent Isn't Broken. Its Foundation Is. | Jonathan Moss, EVP Growth & Partnerships @ Experity
Experity's GTM Intelligence Center lets anyone produce a three-year trend with insights and recommendations in under 30 minutes, without RevOps in the loop.
Week of 24 August 2026 6 Read the briefing
How To Make Your ARR 20% More Valuable To Investors | Keenan, CEO @ A Sales Growth Company
Keenan describes four sales org archetypes: heroic, random, peacock and compounding.
The VC Who Coined "AI Native Services" ft. Jake Saper (Emergence Capital)
The likelier path to an enduring breakout company is building an AI platform from scratch rather than rolling up existing services firms.
Why Great CROs Stop Managing Numbers and Start Building Systems with Sam Costello
Sales process at Harness starts with finding a champion, then doing everything else
SPOTLIGHT: AI Isn't Just Faster Translation, It's a $40B Tug-of-War for Global Attention. | Bryan Murphy, CEO @ Smartling
AI-assisted human translators went from about 2,000 words a day to 8,000 to 10,000 words a day.
E73: The AI Enabling 600 Customer-Facing Reps | Lauren Hughes, VP Revenue Effectiveness @ Justworks
Lauren Hughes cut Justworks' enablement team from 16 to 6 rather than redeploying it, and moved the saved headcount into RevOps and technical builders.
Data Centers in Orbit by 2028: Baiju Bhatt on His Plans After Robinhood
Layering a higher-value service such as compute on top of a commoditized input such as energy creates more margin to reach break-even.
Week of 17 August 2026 4 Read the briefing
The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero
AI-native companies including OpenAI, Cursor, Factory and Anthropic have hired classic enterprise CROs to build their go-to-market teams.
How to Hire Better Salespeople Than Yourself and Lead Them to Win
Likability ranks higher in hiring salespeople than most people expect, because deals depend on building champions and executive relationships.
SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor
Warming a territory before a new rep arrives cut his ramp time from about a year and a half to 90 days.
2 Months of Revenue in 8 Days: How Brex's CRO Fixes What Breaks at Scale ft. Garrett Marker (Brex)
Brex rebuilt enablement around AI role plays and call scoring, which Garrett says cut rep ramp from weeks or months to hours or days.