Learn the System
From AI confusion to marketing precision in four simple steps
Ever wonder how top growth hackers build campaigns so quickly?
Our Substack teaches you the exact four-step method that we developed and refined through years of GTM engineering. While others struggle with each AI update, we keep improving these techniques and share them in a clear system that anyone can use.
What You'll Get
- Weekly live videos showing how to build real campaigns from scratch
- Clear lessons on using AI for better marketing
- Access to our collection of tested AI prompts
Community Benefits
- Weekly Q&A time with marketing experts
- Useful data about what works in different markets
- Join forward-thinking marketers who use AI to enhance ideas, not replace them
Whether you're a tech expert or marketing leader, our GTM engineer and growth hacker disciples use these strategies right away and see better campaign results. Join the group that's changing what's possible with AI-powered marketing.
Stuff From our Substack
The Mass Market Arbitrage Playbook: When Painting the Mona Lisa Is Actually the Wrong Move
TL;DR: Doug and Jordan confess that their entire pain-based segmentation methodology crashes spectacularly for horizontal SaaS companies because the math doesn't work, revealed through Eric Nowoslawski's opposite approach that starts with 100,000+ contacts instead of 1,000, uses intent signals like LinkedIn engagement rather than existential pain, and rapidly tests 15-20 offer/message combinations to find the 2-3 winners hitting 2-3% reply rates before scaling aggressively—what Eric calls "printing the Mona Lisa" instead of painting it. The methodology reverse-engineers customer databases to find statistically similar prospects, kills losing combinations immediately (<1% reply rate gets axed), and operates month-to-month because Eric would rather let you go than get harassed daily about leads. The uncomfortable truth: sometimes you need to stop painting individual prospects and start printing at scale, not because one approach is better but because your market reality demands it.
July 16th, 2025
We’re going to start with something that might hurt: your ICP is probably bullshit.
Not because you did it wrong. Not because you didn't follow the framework correctly. But because the entire premise of organizing go-to-market around a "perfect customer profile" is a relic from a time when data was scarce and personalization was impossible.
Most ICPs probably look something like this: "Mid-market SaaS companies with 100-500 employees, $10-50M revenue, North American headquarters, using Salesforce and HubSpot, led by a VP of Sales aged 35-50."
Here's what that profile actually tells us: nothing about whether they need the solution. Nothing about their urgency to buy. Nothing about the specific pain that keeps their leadership awake at night.
Most companies have created a demographic description masquerading as a strategic framework.
June 26th, 2025
This Is The Way: The SDR Manager's Guide to Cannonball GTM
Why Smart SDR Managers Are Abandoning Spray-and-Pray for Pain-Based Segmentation (And How to Make the Switch Without Getting Fired)
TL;DR: Your SDR just came to you asking to try "this Cannonball thing" instead of following the playbook. Before you say no, consider this: the number of quality conversations per SDR has plummeted 55% since 2014, 36% of companies downsized their SDR teams in 2025, and cold email response rates have dropped 27% in just the last year. The traditional model isn't just broken, it's mathematically unsustainable. Here's why letting your SDR innovators try Cannonball GTM might be the smartest risk you take this quarter.
August 23rd, 2025
The Three-Vector Framework: A Dead Simple Rubric for Picking Winners and Losers
Doug thought he had great instincts for picking winners until Kellen Casebeer showed him he'd been unconsciously running a three-vector system: clients either win without you (Group A), fail despite you (Group B), or crush it with the right partner but crash without one (Group C)—and that's where the money lives. He turned this into a dead-simple rubric: map every opportunity across Value Prop Strength, Competitive Landscape, and Market Dynamics, then attack anything with two strong vectors because Tesla proved you can dominate with A+A despite a tiny market (C), while Zoom rode B+C with massive market size (A). Translation: stop swimming upstream like a programmed salmon and start picking fights you can actually win.
Cannonball GTM Livestream Season 4
See marketing mayhem on most Fridays at 9am PST on LinkedIn
Season Four kicks off October 10th with our Founder Series—where we're throwing a gaggle of baby vertical SaaS brands into the deep end while teaching their founders how to Cannonball live, under absolutely no duress (we promise). Plus killer hands-on episodes where Jordan (and friends) build MCP Servers from scratch and shows you how to construct your own Permissionless Value Proposition agent that doesn't suck. Because watching founders sweat through pain-based segmentation in real-time beats hypothetical case studies every single time.
Season Four Lineup
November 21st | 9:00 am PDT
Dynamic Sales Territory Build
Did you think we were the only ones using AI to break down complex business environments?! Kevin Davis, CEO of BoogieBoard and Doug, the pain-segmentation Ninja and best looking person on the show ever, and, the only person we'll let write his own copy will be mapping out an entire SAM live, while paddling across the Atlantic Ocean on the backs of Golden Dolphins.
Founder Series Cannonball
December 5th | 9:00 am PDT
Some dumb dumb founder is going to get on the show and try and follow what the hell we're doing for 60 minutes and be grateful.
Data Layer Build for Agents
December 12th | 9:00 am PDT
What, we can't data-geek out for 60 minutes? It's for the agents, we swear, it's not for fun. The agents will use this data, we swear. Pinky promise.
Explore Our Livestream Archives
Three seasons of marketing chaos that left a trail of inadvertent brilliance you can binge-watch like that show you pretend not to love.
From diagnosing campaigns for Overjet.ai and developing permissionless value props for Arborgold, to Battle of the Brands showdowns (Doug totally cheated), Clay Day wizardry, and AI-powered systems discovering 1,800 personalized value props in one hour, we've proven systematic pain-based segmentation works across every industry we could cover in more than 30 episodes (so, you know, vertical SaaS). Consider it your master class in "what to do" and sometimes "what definitely not to do."
Season Four Archive
Looking for Season 4 Archives? All archives, including Season 4 can now be found on our Substack for monthly and annual subscribers!
Season Three Archive
Cannonball GTM for (but not with) WingWork
Season 3 | Episode 1 - July 11th, 2025
We went back to our roots to kick off Season Three with an OG Cannonball, this time with a single prompt that took us from Focus to Narrate with a few clicks.
Building a Research Agent for WingWork
Season 3 | Episode 2 - July 18th, 2025
Watch the instant classic - yes, it's up there with Texada and the 'Blue Doug' episode. Watch us as we delivered an agent-ready data framework for the aircraft maintenance industry with the typical chaotic flare you know and love.
The Headless PVP: A Permissionless Value Prop In Search of a HC Brand
Season 3 | Episode 3 - July 25th, 2025
We were at our inverting best as we tackled our first Headless PVP using the Mimilabs.AI healthcare database.
Season 3 | Episode 4 - August 1st, 2025
Watch to get a masterclass in why most companies are applying the wrong go-to-market methodology to their market segment.
Cannonball GTM Data Layer Build for (but not with!) Bolo.AI
Season 3 | Episode 5 - August 8th, 2025
By the end of the livestream, Jordan had accidentally built something that looked less like traditional AI usage and more like conducting an orchestra, with Claude Code as the lead violinist, GPT agents handling percussion, and regular Claude keeping everyone in time.
The Headless PVP: A Permissionless Value Prop for Transportation and Logistics
Season 3 | Episode 6 - August 15th, 2025
We created a data architecture and pathway for a teddy bear Jordan will forever treasure for the multi-modal transportation and logistics sector (aka, we developed a headless PVP and sorta bit off more than we could chew).
The Mega Prompt Generator: How We Turned 60 Minutes of GTM Research Into a Single Automated Workflow
Season 3 | Episode 7 - August 22nd, 2025
Transform any brand website into qualified leads in 60 minutes using our systematic research-to-outreach methodology that compressed months of GTM trial-and-error into a single automated workflow.
The Free TAM Hack: How We Built RevHQ's Entire Market Analysis Using OpenStreetMap + AI
Season 3 | Episode 8 - August 29th, 2025
'It builds the AI data framework layer or it gets the hose again'….join us for more random movie quotes to see how you to can build a data layer that allows you to PVP like a master, this time for Revv.
How We Turned Lenders from Enforcers to Advisors Using Nothing But Public Data
Season 3 | Episode 9 - September 5th, 2025
We dissected Trustpoint.AI live on Friday and accidentally recreated their entire value proposition using only publicly available data. Along the way, we discovered that construction projects failing inspections twice have an 80% correlation with budget overruns appearing 45 days later.
OG Cannonball for Rematter: When AI Meets Scrap Metal
Season 3 | Episode 10 - September 12th, 2025
We went from soup to nuts with Rematter.com, a SaaS platform that helps scrap recycling operations actually run their businesses. And we did it the hard way: no pre-loaded context, no safety nets. Just pure methodology and Jordan's terrifying ability to make AI do exactly what he wants.
Season Two Archive
Brand Blitz: Finding Pain-Based Segments for 4 Vertical SaaS Brands from Legal Services
Season 2 | Episode 1 - April 4th, 2025
Watch our livestream where we battle AI to identify high-converting pain segments for legal tech companies—proving that even when tech fails (hello, StreamYard issues), the methodology prevails.
Battle of the Brands: Narrative Showdown for 2 vertical SaaS Brands from Legal Services
Season 2 | Episode 2 - April 11th, 2025
Doug and Jordan went toe-to-toe on the Battle of the Brands to see who could deliver the best PVP for DISCO and Evisort. The result? A tie (though Doug cheated, a lot).
Clay Day: Strategic Deployment
Season 2 | Episode 3 - April 18th, 2025
After summarizing the Focus, Investigate, and Narrate steps of our methodology, we dedicated an entire hour to Clay.com deployment strategies for two vertical SaaS brands. Note: paid annual subscribes only.
Vertical Voyage: SaaS Discovery Hour
Season 2 | Episode 4 - April 25th, 2025
We took viewers through the complete methodology for two vertical SaaS brands except without the FIND bit….intrigued? We're unveiled the simple, two step Cannonball 2.0, don't miss it!
Mapping a Pain-Based Category in One Hour
Season 2 | Episode 5 - May 9th, 2025
Watch as we map the EHR and Practice Management Category.
Clay Day: Strategic Deployment with Jeremy Ross
Season 2 | Episode 6 - May 16th, 2025
Watch as Jeremy and Jordan explore self-improving AI and an example of wave 1 MCP servers.
AI Agents in the Enterprise with David Boscovic
Season 2 | Episode 7 - May 23rd, 2025
Watch how Flatfile turned the Cannonball GTM methodology into a $50-per-vertical AI system that discovers existential pain points across hundreds of markets simultaneously, proving that systematic pain-based segmentation isn't just theory anymore.
OG Cannonball with Numeo.AI
Season 2 | Episode 8 - May 30th, 2025
We mapped the transportation and logistics technology sector and performed an end-to-end Cannonball for Numeo.ai, an AI-powered dispatch automation platform that handles broker calls, negotiates freight rates, and secures loads for trucking carriers and dispatchers.
The Clinical Trial Approach to Message-Market Fit with Kellen Casebeer
Season 2 | Episode 9 - June 6th, 2025
We explored Kellen's Market → Segment → Persona → Angle methodology for horizontal SaaS, proving that systematic message-to-market fit testing can create the same precision for broad markets that our pain-based approach delivers for vertical plays.
Shovels MCP Server: Programmatic Pain Point Discovery
Season 2 | Episode 10 - June 13th, 2025
Jordan deployed the Shovels database via MCP server in Clay to demonstrate programmatic PVP (pain-based value propositions) for 1,800 construction industry prospects from the International Builders Show—proving that systematic pain discovery can scale beyond manual research to deliver personalized insights for every company in your target market.
Shovels MCP Clay Campaigns with Kellen Casebeer
Season 2 | Episode 11 - June 20th, 2025
Watch as we demonstrate how to operationalize AI-generated value propositions using a complete end-to-end automated campaign for Shovels, targeting leads from the International Builders Show.
Demo and Q&A of the Latest Features from Clay.com
Season 2 | Episode 12 - June 27th, 2025
Check out the OG GTM Engineer and Head of Education @ Clay, Yash Tekriwal, demo four fresh AI features that can transform how GTM engineers build campaigns: native AI chat for troubleshooting tables, document upload for personalized outbound, Claygent Navigator for form automation, and AI image generation.
Season One Archive
Check out this masterclass in defining ICP and discovering pain-based segments.
