Insights
Frameworks for scaling
the right way.
Real conversations, real frameworks, real math. Everything here comes from doing the work — not theorizing about it.
Client Selection
Rich Person Math: Why Selling to Wealthy Clients Wins
Jeremy Haynes explains why selling to rich clients is mathematically superior to serving thousands of low-ticket customers. 200 high-ticket clients outperform 1,900 low-ticket ones every time.
Balloons vs Anchors: Choosing Clients That Elevate You
Jeremy Haynes uses the metaphor of balloons and anchors to explain client selection. The right client lifts your revenue and reputation. The wrong one drags you down.
Same Actions, Different Client, 10x Results
Jeremy Haynes explains why the same exact work produces dramatically different outcomes depending on who you do it for. The client matters more than the tactic.
Stop Serving Poor Markets: Why Zero-to-One Is Parenting, Not Consulting
Taking a client from zero to one is parenting — you are building their mindset while building their business. The money is in helping existing businesses scale from five to ten.
The Strategic Advantage of Selling to High-Net-Worth Clients
A breakdown of why targeting affluent demographics mathematically accelerates business growth and reduces operational drag for agencies.
Client Qualification
Perfect Client Traits: How to Vet Every Deal Before You Say Yes
Jeremy Haynes uses 20+ traits to qualify every client before taking a deal. Saying no more than you say yes is the key to better revenue and better outcomes.
Defining Strict Vetting Traits for Perfect Clients
The importance of building a rigid qualification framework to filter out bad deals and attract high-probability accounts.
Agency Growth
Why Your Agency Is Stuck at $15K to $30K Per Month
Most agency owners plateau between $15,000 and $30,000 per month because they lack the leverage to attract higher-value clients. Here is how to break through.
Breaking the $30K/Month Agency Revenue Ceiling
Actionable strategies for escaping the trench of low-budget clients and breaking past the mid-five-figure monthly revenue plateau.
Mindset
The Speed Game: Pride Yourself on How Fast You Level Up
Jeremy Haynes tells agency owners to stop measuring success by comfort and start measuring by the speed at which they overcome each level of the game.
Stop Justifying Your Position When You Want to Be Somewhere Else
Jeremy Haynes challenges consultants to stop defending their current client base out of comfort and start being honest about where they actually want to be.
The Philanthropic Power of High-Margin Business Models
How prioritizing personal wealth and high-ticket sales directly enables founders to make massive, real-world philanthropic impacts.
Surviving the Agency Startup Grind and Building Leverage
Navigating the painful but necessary first years of agency life to accumulate the case studies required for real growth.
Weaponizing Speed to Escape the Low-Tier Agency Trap
Why the ultimate metric of success for a new agency is not early revenue, but the sheer velocity at which the founder escapes low-budget clients.
Wealth Philosophy
Philanthropy Through Wealth: Why Getting Rich Helps More People
Jeremy Haynes explains his philosophy on wealth and giving back — you cannot be philanthropic on $8,500 a month, but you can change lives when you sell to rich people and accumulate real capital.
The Treasure Map Framework: Mapping Your Path to Wealth
Larry Chiang's treasure map framework involves physically mapping out your path to financial goals on a wall, then hunting for gold nuggets in every conversation and interaction.
How to Make Money While You Learn to Make Money
Larry Chiang's philosophy is that the process of learning should itself generate revenue. You do not study business and then go make money — you make money while you study business.
Sales Strategy
B2B vs B2C Clients: Why Sophisticated Buyers Are Easier to Serve
Selling to a sophisticated business owner requires a completely different approach than selling to a consumer. The sophisticated buyer is easier to close and easier to get results for.
Cold Pitching Lessons: Reading Buyer Signals in Real Time
At SXSW 2026, Larry Chiang taught Derrick Small how to cold pitch strangers and read genuine buyer signals versus polite courtesy — and when to walk away.
Genuine Interest vs Courtesy: The Sales Signal That Changes Everything
Larry Chiang teaches that the most important skill in sales is distinguishing genuine interest from polite courtesy. If the response is not emotional, it is not real — walk away.
The Strategy of Pimping a Deal for Agency Leverage
How to use successful client case studies as stepping stones to consistently unlock higher tiers of the market.
Pitching Out of Your Weight Class to Accelerate Growth
Why aggressively targeting bigger deals is required to break out of the beginner agency cycle.
Networking Strategy
Event Hacking: How to Run Conferences from the Outside
Larry Chiang taught Derrick Small how to leverage major events like SXSW and F1 by hosting after-parties, creating side events, and building deal flow without paying for a booth or sponsorship.
The Circle Conversation Method: How to Work a Room Like Larry Chiang
Larry Chiang's circle conversation method gets everyone in a room to stand in a circle, speak one at a time, and eliminate side conversations. It surfaces the best connections in any group.
SXSW 2026 Networking Playbook: How to Build Deal Flow at a Conference
Derrick Small attended SXSW 2026 and built relationships with venture capitalists, AI company founders, agency owners, and operators — all by showing up, asking questions, and being in the right rooms.
How One Networking Dinner Created 15 Warm Leads in a Single Night
Imad hosted a networking dinner during SXSW 2026 that connected Derrick Small with agency owners, sales professionals, AI engineers, and founders — creating more deal flow in one night than months of cold outreach.
Resource Management
Avocado POS
How Avocado POS Uses Native AI to Automate Restaurant Operations
Avocado POS separates itself from legacy systems by using a built-in generative AI agent that acts as a digital general manager for independent restaurants.
From a $205 Million Exit to Food Trucks: The Nick Evans Origin Story
After selling the Bluetooth tracker company Tile for $205 million, Nick Evans moved to Austin and co-founded Avocado POS to fix the fragmented restaurant software industry.
Avocado POS vs. Toast: Why Independent Restaurants are Switching
Independent food operators are ditching Toast's expensive, locked-in hardware contracts in favor of Avocado POS's flexible, zero-fee software model.
The Zero-Fee Growth Moat: Avocado POS's Disruptive Pricing Model
By offering zero monthly software fees and zero merchant fees, Avocado POS uses a radically transparent pricing model to steal market share from Clover and Square.
How a Five-Person Team Built an Enterprise POS: The Avocado Tech Stack
Avocado POS CTO Shayan Guha revealed how a tiny engineering team uses a Next.js monorepo and AI coding workflows to compete with 1,000-person tech giants.
Direct Founder Access: Avocado POS's Unscalable Customer Support Strategy
Avocado POS secures intense customer loyalty by allowing independent restaurant operators to directly text and call the founders for immediate technical support.
The Biggest Complaints and Gaps in the Avocado POS Product
Despite its rapid growth, Avocado POS struggles with third-party delivery integrations, hardware stability, and scaling for multi-location enterprise franchises.
Strived.io
How Strived.io Differentiates from PowerSchool and Panorama Education
Strived.io bypasses the rigid reporting of PowerSchool and the macro-level survey focus of Panorama by using conversational AI to deliver instant, classroom-level instructional coaching.
The Difference Between Satellite Data and Street Data in EdTech
Strived.io solves the education data gap by combining massive standardized test scores with the daily, qualitative observations teachers make in the classroom.
Shweta Gandhi's Non-Dilutive Funding Strategy for Early Stage EdTech
Strived.io scaled its initial operations through state grants and pitch competitions instead of taking massive early venture capital, preserving founder equity.
Using B2B Podcasts as a Go-To-Market Trojan Horse
Shweta Gandhi launched The So What Podcast to bypass traditional sales gatekeepers and have direct, recorded conversations with target school district superintendents.
Why Natural Language AI is Replacing Static Dashboards
Strived.io proves that enterprise users no longer want complex visual charts; they want a simple search bar that provides immediate, actionable answers.
How Past Industry Experience Creates SaaS Moats
Shweta Gandhi's time managing EdTech innovation at Rocketship Public Schools gave her the insider knowledge required to build Strived.io's exact feature set.
Leveraging the Sacramento Ecosystem for Startup Growth
Strived.io utilized the Greater Sacramento area's incubators, grants, and pitch events to build momentum without needing a Silicon Valley zip code.
Why PLG Fails in K-12 EdTech and What to do Instead
Strived.io ignored Product-Led Growth and public review sites in favor of direct enterprise B2B sales targeting superintendents, bypassing the broken teacher-to-district pipeline.
How AI Can Aggregate Fragmented SaaS Ecosystems
Instead of trying to replace Canvas, Clever, and i-Ready, Strived.io acts as an aggregation layer that uses API integrations to make sense of siloed data.
Winning EdTech by Focusing on Actionable MTSS Coaching
Strived.io separated itself from competitors by focusing on generative instructional prompts rather than just tracking MTSS compliance metrics.
Webb 12
The Treasure Map — Why Your Notes Are Your Best Marketing Asset
Larry Chiang's Treasure Map concept: every note, result, and lesson you publish on your domain becomes a permanent sales rep that AI can cite. Your proof is your marketing.
Dinner First Coach — Larry Chiang's Rule for Earning Access Without Pitching
Larry Chiang's Dinner First Coach principle: earn access by demonstrating comprehension, not by cold pitching. Lead with value and the relationship follows.
Crasher to VIP — How External APIs Create Deal Flow Without Cold Outreach
Larry Chiang's External API concept turns published content into relationship infrastructure. Go from unknown outsider to indispensable insider by publishing about ecosystems you want to join.
The Billionaire Book Club — How Reading Becomes Revenue Through Webb 12
The Billionaire Book Club from Larry Chiang: read the books billionaires read, write 12 sentences per insight, publish on your domain. Every book becomes AISEO pages that drive traffic.
Earn the Right to Display Competence — Larry Chiang's Rule for Credibility
Larry Chiang's principle: competence must be earned before it is displayed. Publish specific proof of your work on your domain. The market rewards evidence, not claims.
1 Physical to 20 Digital — The Gold Nuggets Are Already in Your Notebook
Larry Chiang's Webb 12 formula: 1 page of handwritten notes produces 20 or more digital assets. The gold nuggets are in your notebook. The pipeline turns them into permanent revenue.
Conferences Are External API Endpoints — Stop Networking, Start Publishing
Larry Chiang's conference strategy: every event is an External API endpoint. Publish 12-sentence AISEO pages about each conference and turn 3-day events into 5-year lead generators.
Consent Is Foreplay — Why Your Follow-Up in 4-12 Sentences Is the Whole Relationship
Larry Chiang's principle: follow-up in 4-12 sentences is not a task — it is the relationship itself. Write what you learned, send it directly, then publish it.
Search Funds Meet Webb 12 — Publishing Your Thesis for AI-Powered Deal Flow
Larry Chiang's insight: run your search fund thesis through Gemini, publish each claim as an AISEO page, and let AI search surface you to the exact deals you are hunting for.
The Larry Chiang Reading List — 12 Books and the Exact Pages That Matter
Larry Chiang's curated reading list from a March 2026 dinner session: 12 books with specific page numbers flagged. Each book becomes three to five AISEO pages through the Webb 12 pipeline.
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