I’m not an adrenaline junky. I don’t bungee jump, skydive, or seek out extreme sports for the thrill. But there’s one rush I absolutely live for: that heart-pounding moment when you realize you’ve committed to something you have absolutely no idea how to deliver. Welcome to entrepreneurship.
When I started my business, I had a dangerous combination of ambition and ignorance. I was the guy nodding knowingly in client meetings while frantically Googling terms under the table. My right-hand person, Lina, became a master at real-time research, sliding me lifesaving information through our chat window while I bought time with strategic, “That’s a great question …” stalls.
To be crystal clear: I’m not advocating dishonesty. What I am advocating is refusing to be intimidated by what you don’t know. Because here’s the truth: it can all be learned. And never in human history has that been more possible than right now.
The Art of the Entrepreneurial Leap
One of my favorite aspects of business ownership is being forced to figure things out on the fly. When you’re an employee, you can defer tough problems to someone else. When you’re the owner, the buck stops with you. That pressure? It’s where magic happens.
My friend Suzanne Taylor-King puts it perfectly: “We don’t have to know everything, we just have to be one step ahead of our clients.”
That’s it. One step. Not a PhD in the subject. Not years of experience. Just one step ahead.
But here’s where it gets interesting. And where AI changes everything.
When Avatars Write Checks Your Business Can’t Cash
Let me tell you about the time one of our AI avatars nearly gave me a heart attack. We had set up automated social media posting for one of our client accounts. The avatar was doing great: engaging content, consistent messaging, building audience. Then one day, I got a notification that made my blood run cold.
The avatar had posted about a proprietary process that … didn’t exist. Not only had it posted about this fictional process, but it had described it in detail and invited people to learn more about it. My phone started buzzing with inquiries almost immediately.
My first instinct? Panic. My second? Delete the post and pretend it never happened. But then something clicked. This wasn’t a crisis — it was an opportunity to build the plane while falling.
Turning Overpromise into Overdeliver
Instead of running from the problem, I leaned into it. I had inadvertently promised something that didn’t exist, but that didn’t mean it couldn’t exist.
Here’s what I did:
- Acknowledged the situation internally (and put better controls in place — lesson learned)
- Leveraged AI to rapidly develop the promised process using existing frameworks and proven methodologies
- Created comprehensive documentation and training materials in a fraction of the time it would have taken manually
- Delivered something even better than what was originally promised
The result? What started as an embarrassing mistake became one of our most popular offerings. Those initial inquirers became some of our best clients.
The Diamond Formation Process
Diamonds are formed under pressure. So are our best ideas. Nothing adds pressure quite like promising a solution that doesn’t exist yet. (Again, I’m not advocating for making commitments you can’t keep, but I am advocating for being committed to delivering on any commitment made.)
When your back is against the wall, creativity kicks into overdrive. When there’s no choice but to figure it out, you find ways that didn’t exist before. And with AI as your co-pilot? You’re in a better position to deliver than ever before in human history.
How AI Enables (and Sometimes Encourages) Our Worst Instincts
Here’s the thing about AI — it can facilitate some of our worst entrepreneurial instincts. It makes it easier to:
- Overpromise because generating content feels effortless
- Overcommit because automation makes everything seem scalable
- Overcomplicate because AI can produce infinite variations
But it also bails us out when we write checks our capabilities can’t immediately cash. AI helps us:
- Research rapidly to fill knowledge gaps
- Develop solutions quickly using proven frameworks
- Scale delivery to match ambitious promises
- Learn and iterate faster than ever before
The New Rules of Entrepreneurial Risk-Taking
In this AI-enabled world, the rules of business risk have changed:
- Old Rule: Don’t commit until you’re 100% sure you can deliver
- New Rule: Commit with confidence that you can figure out delivery
- Old Rule: Know everything before you start
- New Rule: Stay one step ahead and learn aggressively
- Old Rule: Build everything before you sell anything
- New Rule: Build the plane while you’re flying it
Your Entrepreneurial Leap Checklist
Ready to embrace the jump-first mentality? Here’s how to do it intelligently:
Before the Leap:
- Ensure you have strong problem-solving capabilities
- Build a reliable research and learning system
- Establish clear communication with your team
- Set up AI tools that can help rapid development
During the Fall:
- Stay calm and solution-focused
- Leverage every available resource (especially AI)
- Communicate transparently with stakeholders
- Document everything for future reference
After Landing:
- Analyze what worked and what didn’t
- Improve your systems and controls
- Share lessons learned with your team
- Prepare for the next leap
The Courage to Not Know Everything
The biggest barrier to entrepreneurial success isn’t lack of knowledge — it’s the fear of not knowing everything. But here’s what I’ve learned: The willingness to jump before you’re ready is often what separates successful entrepreneurs from everyone else.
You don’t need to know everything. You just need to know you can figure it out. And with AI in your toolkit, figuring it out has never been more achievable.
