Baby Weights for Business

"You don't want to walk into the gym on day one and try and deadlift 300 pounds. So when someone comes to me and they're a first time entrepreneur and they say, 'I'm going to make the next great AI company,' I think that is the equivalent." - Andrew Wilkinson

What It Is

This framework uses a gym analogy to help first-time entrepreneurs choose appropriately sized business challenges. Just as you wouldn't attempt a 300-pound deadlift on day one at the gym, you shouldn't attempt a complex, highly competitive, regulated business as your first venture.

The key insight is that early entrepreneurial wins create a powerful narrative: "I'm good at business, I can do this, keep going." That narrative sustains you through later, harder challenges. Without it, most people give up after their first failure.

How It Works

Why simple businesses first:

1. Immediate feedback - You quickly learn if you can do this
2. Narrative building - Success creates the belief that you can succeed
3. Skill development - You learn business fundamentals with lower stakes
4. Capital preservation - Less money at risk while learning
5. Confidence for bigger bets - Past wins fund emotional resilience for future losses

The Progression:

• Level 1: Service businesses (web design, consulting, coaching)
• Level 2: Simple product businesses with clear demand
• Level 3: Businesses requiring capital, teams, or complex operations
• Level 4: Highly competitive, regulated, or technology-intensive businesses

Warning signs you're lifting too heavy:

• First-time founder attempting to "build the next great AI company"
• Starting a bank or highly regulated business without industry experience
• Competing directly with venture-backed incumbents while bootstrapping
• Building something that requires 50+ people before generating revenue

How to Apply It

1. Assess your experience level - How many businesses have you started? How many succeeded?

2. Rate business difficulty factors:

   • Competition intensity
   • Capital requirements
   • Regulatory complexity
   • Team size needed
   • Time to first revenue
   • Number of failure points

3. Match difficulty to experience:

   • First business: Minimize all difficulty factors
   • Second/third business: Add one or two complexity factors
   • Experienced: Take on harder challenges with capital and skills from prior wins

4. Choose for early wins - The first business should almost certainly work if you execute. Examples:

   • Consulting/services in your expertise area
   • Software solving a narrow, clear problem
   • Local service business with proven demand

5. Build the muscle - Use early wins to develop skills, capital, network, and confidence for bigger plays

When to Use It

• When choosing your first business idea
• When mentoring first-time founders
• When evaluating if an opportunity matches your current capabilities
• When tempted by a glamorous but complex opportunity

Examples from Andrew Wilkinson

Good first business (simple, immediate feedback):

• Web design agency (Metalab): "All I had to do was know how to build websites and be able to talk to potential customers... I got immediate positive feedback"

Too complex for first-time (multiple failure points):

• Pizzeria: "If the baker doesn't wake up at three in the morning and start prepping dough, the entire thing is effed"
• Bar: "We realized that we didn't know anything about business compared to someone who runs a pizzeria"
• Flow (Asana competitor): Lost $10M competing with venture-backed companies while bootstrapping

Source

• Guest: Andrew Wilkinson
• Episode: "I've run 75+ businesses. Here's why you're probably chasing the wrong idea."
• Key Discussion: (00:07:30) - Gym analogy and first business advice
• YouTube: Watch on YouTube

Related Frameworks

• Fish Where the Fish Are - Find markets with less competition
• Explore and Exploit - Balance experimentation with doubling down