
The Step-by-Step Plan to Go From $3M to $10M+
02/10/25 • 51 min
1 Listener
In this episode, Ayman Al-Abdullah, former CEO of AppSumo, shares his framework for scaling businesses from seven to nine figures. The conversation focuses on the importance of customer retention, strategic hiring, and proper incentive structures. Ayman shares insights from his experience scaling AppSumo from $3M to $84M in revenue, emphasizing the transition from founder to CEO mindset.
Timestamps:
00:00 - Introduction and background
02:47 - Discussion of the Nine Steps framework
08:13 - Team building and executive compensation
10:35 - The Reality of Startup Valuations
14:36 - The importance of setting a strong foundation
15:59 - Focus on Retention Before Growth
22:26 - Evaluating Opportunities and Thinking Big
29:47 - Examples of Successful Founders that Ayman admires
31:35 - The Importance of Focus in Business
33:26 - Build Skyscrapers, Not Strip-malls
36:01 - The importance of being the best in the market
37:54 - Where to double down in your business
40:22 - Testing and Investing in Business Strategies
42:05 - Identifying Bottlenecks in Your Business
44:39 - Finding Your Zone of Genius
Key Points:
• The "Nine Steps to Nine Figures" framework divides business growth into three phases: startup, scale-up, and grow-up
• Focus on retention and customer loyalty before aggressive growth
• Use the "Test Then Invest" framework with 80% resources on core business and 20% on experiments
• Structure executive compensation with a 50-50 split between top-line and bottom-line metrics
1) The "Nine Steps to Nine Figures" Framework:
Breaks down into 3 phases:
• Startup (Product Market Fit)
• Scale-up (Company Creation)
• Grow-up (Legacy Protection)
Most founders get this wrong from day 1...
2) RETENTION over GROWTH
"Building a business without focusing on retention is like building a skyscraper on sand"
Every 3% increase in net revenue retention = DOUBLES company valuation
Stop chasing growth before you nail retention!
3) The 80/20 Marketing Rule:
• 80% of resources on proven channels
• 20% on experimental channels
Real example: AppSumo tested switching from credits to cash payments for referrals → Became 8-figure revenue channel
4) The Shield vs Sword Framework for Decision Making:
Rate every opportunity 1-5 on:
• Impact (Sword)
• Effort (Shield)
Only pursue 8+/10 total score opportunities
Ignore the rest - they're distractions
5) On Building Your Executive Team:
Two core functions:
• Sales (CRO)
• Delivery (COO)
Pro tip: Hire first in YOUR zone of genius
Why? You'll know what excellence looks like
6) The Triple, Triple, Double, Double Path to $100M:
Year 1: $3M → $9M
Year 2: $9M → $27M
Year 3: $27M → $54M
Year 4: $54M → $108M
This is how you hit 9-figures in 5 years
7) REVOLUTIONARY Compensation Framework:
Forget traditional equity!
Instead:
• Set total comp package
• Let employees choose cash vs equity split
• Makes equity REAL by forcing skin in the game
8) CEO Evolution:
"The founder is the hardest working person
The CEO should be the laziest"
Your job: Think 3-5 quarters ahead while your team executes
Key Takeaway:
Focus on retention first
Build processes before hiring
Think in 5-year blocks
Execute with intention
Notable Quotes:
"Product market fit is when it feels like you're wearing a meat suit in a dog park - you just have more leads than you know what to do with." - Ayman
"Every 3% increase in net revenue retention doubles a company's valuation." - Ayman
LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/
BoringAds — ads agency that will build you profitable ad campaigns http://boringads.com/
BoringMarketing — SEO agency and tools to get your organic customers http://boringmarketing.com/
Startup Empire - a membership for builders who want to build cash-flowing businesses https://www.startupempire.co
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
FIND AYMAN ON SOCIAL
Ayman’s Website: https://aymanalabdullah.com
X/Twitter: https://x.com/aymanalabdul
LinkedIn: https://www.linkedin.com/in/aalab003/
In this episode, Ayman Al-Abdullah, former CEO of AppSumo, shares his framework for scaling businesses from seven to nine figures. The conversation focuses on the importance of customer retention, strategic hiring, and proper incentive structures. Ayman shares insights from his experience scaling AppSumo from $3M to $84M in revenue, emphasizing the transition from founder to CEO mindset.
Timestamps:
00:00 - Introduction and background
02:47 - Discussion of the Nine Steps framework
08:13 - Team building and executive compensation
10:35 - The Reality of Startup Valuations
14:36 - The importance of setting a strong foundation
15:59 - Focus on Retention Before Growth
22:26 - Evaluating Opportunities and Thinking Big
29:47 - Examples of Successful Founders that Ayman admires
31:35 - The Importance of Focus in Business
33:26 - Build Skyscrapers, Not Strip-malls
36:01 - The importance of being the best in the market
37:54 - Where to double down in your business
40:22 - Testing and Investing in Business Strategies
42:05 - Identifying Bottlenecks in Your Business
44:39 - Finding Your Zone of Genius
Key Points:
• The "Nine Steps to Nine Figures" framework divides business growth into three phases: startup, scale-up, and grow-up
• Focus on retention and customer loyalty before aggressive growth
• Use the "Test Then Invest" framework with 80% resources on core business and 20% on experiments
• Structure executive compensation with a 50-50 split between top-line and bottom-line metrics
1) The "Nine Steps to Nine Figures" Framework:
Breaks down into 3 phases:
• Startup (Product Market Fit)
• Scale-up (Company Creation)
• Grow-up (Legacy Protection)
Most founders get this wrong from day 1...
2) RETENTION over GROWTH
"Building a business without focusing on retention is like building a skyscraper on sand"
Every 3% increase in net revenue retention = DOUBLES company valuation
Stop chasing growth before you nail retention!
3) The 80/20 Marketing Rule:
• 80% of resources on proven channels
• 20% on experimental channels
Real example: AppSumo tested switching from credits to cash payments for referrals → Became 8-figure revenue channel
4) The Shield vs Sword Framework for Decision Making:
Rate every opportunity 1-5 on:
• Impact (Sword)
• Effort (Shield)
Only pursue 8+/10 total score opportunities
Ignore the rest - they're distractions
5) On Building Your Executive Team:
Two core functions:
• Sales (CRO)
• Delivery (COO)
Pro tip: Hire first in YOUR zone of genius
Why? You'll know what excellence looks like
6) The Triple, Triple, Double, Double Path to $100M:
Year 1: $3M → $9M
Year 2: $9M → $27M
Year 3: $27M → $54M
Year 4: $54M → $108M
This is how you hit 9-figures in 5 years
7) REVOLUTIONARY Compensation Framework:
Forget traditional equity!
Instead:
• Set total comp package
• Let employees choose cash vs equity split
• Makes equity REAL by forcing skin in the game
8) CEO Evolution:
"The founder is the hardest working person
The CEO should be the laziest"
Your job: Think 3-5 quarters ahead while your team executes
Key Takeaway:
Focus on retention first
Build processes before hiring
Think in 5-year blocks
Execute with intention
Notable Quotes:
"Product market fit is when it feels like you're wearing a meat suit in a dog park - you just have more leads than you know what to do with." - Ayman
"Every 3% increase in net revenue retention doubles a company's valuation." - Ayman
LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/
BoringAds — ads agency that will build you profitable ad campaigns http://boringads.com/
BoringMarketing — SEO agency and tools to get your organic customers http://boringmarketing.com/
Startup Empire - a membership for builders who want to build cash-flowing businesses https://www.startupempire.co
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
FIND AYMAN ON SOCIAL
Ayman’s Website: https://aymanalabdullah.com
X/Twitter: https://x.com/aymanalabdul
LinkedIn: https://www.linkedin.com/in/aalab003/
Previous Episode

I built an AI startup in 65 minutes (using ChatGPT, Leonardo AI, Kling AI, ElevenLabs)
Greg's step-by-step guide to building a startup using AI workflows: https://www.gregisenberg.com/ai-startup
In this episode, Omar Choudhry, a serial entrepreneur, shares the exact prompting sequences he uses to combine multiple AI tools to create products people actually want to buy. Watch us build a custom avatar business live. You'll learn the exact process: from crafting the perfect prompts in ChatGPT, to generating images in Leonardo AI, to animating with Kling AI, all the way to automated fulfillment with Printful. This isn't theory - it's a complete blueprint you can copy today.
Timestamps:
00:00 - Introduction and overview
04:22 - Technical, Audience, and Cultural Shifts
10:12 - Explanation of sequential prompting
14:15 - How to create an AI Avatar using ChatGPT and Leonardo AI
26:18 - Startup Idea 1: Custom AI Greeting Cards
36:43 - Teenie Tales MVP showcase
43:10 - How to animate AI Avatar’s using Kling AI
52:50 - Startup Idea 2: Personalized AI Sticker’s
Key Points:
• Detailed walkthrough of creating AI avatars using sequential prompting across multiple AI tools
• Exploration of business opportunities in personalized greeting cards and educational materials
• Discussion of automated workflows combining ChatGPT, Leonardo AI, and Kling AI
• Integration strategies with print-on-demand services like Printful for physical products
1) The Big Shift in Business Models:
Traditional path:
• Raising VC $$$
• Years to launch
• Large teams
• Office space needed
New AI-First path:
• Build instantly
• Low cost
• Zero employees
• Remote-first
2) The Sequential Prompting Framework
Omar's genius method:
• Use ChatGPT to create prompts
• Feed prompts to specialized AI tools
• Chain outputs together
• Build user-friendly frontend
Example flow:
ChatGPT → Leonardo AI → Kling AI → 11Labs
3) Business Idea #1: AI-First Greeting Cards
The $400M Moonpig-killer:
• Upload photos → Get AI avatars
• Generate personalized scenes
• Add animation & voice
• Print physical cards
Monetization:
• $7-10 per card
• $10-15 monthly subs
• Gift upsells
4) Business Idea #2: Educational AI Stickers
Target market: Schools & Teachers
The product:
• Custom teacher avatars
• Personalized student stickers
• Achievement celebrations
• Classroom decorations
Distribution:
• Direct mail to principals
• School district partnerships
5) The Technical Stack
Tools needed:
• ChatGPT for prompts
• Leonardo AI for images
• Remove.bg for backgrounds
• Printful API for fulfillment
• Zapier/Make for automation
CAC potential: $15/customer
6) Marketing Strategy
Guerrilla tactics:
• Find faculty directories
• Create custom samples
• Direct mail campaigns
• Social media DM outreach
• Leverage virality in schools
Pro Tip: Start manual, perfect the process, then automate!
7) BONUS INSIGHT
The real opportunity isn't just in the tools - it's in the UX layer on top.
Build specific solutions for specific problems.
Create branded experiences.
Make it dead simple to use.
The tools are commodities. The experience is the moat.
Notable Quotes:
"We're building full workflows today using AI avatars. I'm going to have a ton of business ideas that you can start immediately with zero employees." - Omar
"By the end of this episode, you'll be able to assemble an AI SaaS product that can literally print you cash." - Omar
LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/
BoringAds — ads agency that will build you profitable ad campaigns http://boringads.com/
BoringMarketing — SEO agency and tools to get your organic customers http://boringmarketing.com/
Startup Empire - a membership for builders who want to build cash-flowing businesses https://www.startupempire.co
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
FIND OMAR ON SOCIAL
5 Day Sprint - Build with AI: https://www.skool.com/5-day-sprint/about
Instagram: https://www.instagram.com/omarchoudhry/
X/Twitter: https://x.com/OmarChoudhry
LinkedIn: https://www.linkedin.com/in/omarchoudhry/?originalSubdomain=uk
Next Episode

The Actual Process Behind a $10.5K/Month Directory Website
Get the exact system used to build profitable local directories: https://www.gregisenberg.com/directory
The episode features Frey Chu explaining his methodology for building profitable directory websites, using dog parks as a case study. He demonstrates how to identify opportunities through keyword research, validate ideas through social proof, and implement a basic yet effective directory structure. The discussion emphasizes that even simple directory websites can generate significant passive income through various monetization methods, while also serving as a foundation for larger business opportunities.
Timestamps:
00:00 - Intro
03:40 - Examples of Profitable Directories and their traffic
10:35 - Why Build Directories
12:23 - Finding and validating directory ideas
26:44 - Data collection and enrichment
42:21 - WordPress implementation
46:36 - Monetization strategies
Key Points:
• How to identify profitable directory website opportunities using keyword research and competition analysis
• Step-by-step process for validating directory ideas using Reddit and social listening
• Data collection and enrichment techniques for building comprehensive directories
• Simple implementation strategy using WordPress or other CMS platforms
• Monetization strategies including AdSense, affiliate marketing, and potential SaaS opportunities
1) First, find your niche:
• Use Ahrefs "near me" searches
• Look for 30-100K monthly searches
• Target keyword difficulty under 20
• Avoid seasonal/branded keywords
• Find niches with fragmented search intent
2) Validate your idea:
• Check competition on Google
• Look for basic/outdated directories
• Browse Reddit discussions
• Confirm real user pain points
• Set a "bounty" on weak competitors
3) Data Collection Strategy:
• Use Google Maps scraping tools (like Outscraper)
• Focus on exact category matches
• Collect key data points:
Name, address, phone
- Reviews & ratings
- Hours & location links
- Street view images
4) Data Enrichment
• Add unique features competitors lack
• Include amenity details (shade, benches, etc)
• Use AI tools to automate enrichment
• Focus on solving specific user problems
• Make data actually USEFUL
5) Building The Directory:
• Start with simple "static pillar pages"
• Target city-specific keywords
• Include:
Table of contents
- Location details
- Embedded maps
- Reviews
- Internal linking structure
6) Monetization Options
• Display ads (most passive)
• Affiliate partnerships
• Lead generation
• Data collection/email lists
• Potential SaaS upsell
Notable Quotes
"AdSense has been the closest thing that I've ever experienced to passive income." - Frey Chu
"People are monetizing directories wrong. They're just putting AdSense... The opportunity is actually to build software on top of these directories." - Greg Isenberg
LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/
BoringAds — ads agency that will build you profitable ad campaigns http://boringads.com/
BoringMarketing — SEO agency and tools to get your organic customers http://boringmarketing.com/
Startup Empire - a membership for builders who want to build cash-flowing businesses https://www.startupempire.co
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
FIND FREY ON SOCIAL
X/Twitter: https://x.com/freychu
Youtube: https://www.youtube.com/@FreyChu
Frey’s Newsletter: https://shipyourdirectory.kit.com
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