I've been wrong about why manual outreach wasted my time and what i did instead more times than I'd like to admit. But the last mistake taught me something I can't unlearn.
When I tried to grow our sales team, it didn’t go well at first. Then we started using sales forecasting, and everything changed. I want to share the framework that helped us triple our pipeline without hiring more people.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating why manual outreach wasted my time and what i did instead. It's not complicated, but it requires discipline.
Step 1: the best solutions are often the simplest ones This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: customer feedback is the only metric that matters Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly Nothing works perfectly the first time. The companies in my portfolio that nail why manual outreach wasted my time and what i did instead are the ones that treat it as an ongoing process, not a one-time project.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to why manual outreach wasted my time and what i did instead are fundamentally flawed. Not slightly off. Fundamentally flawed.
The root cause is usually one of three things:
- Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
- Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
- Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
What I've Learned From 122 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with why manual outreach wasted my time and what i did instead.
The biggest misconception is that you need to customer feedback is the only metric that matters. That's backwards. The companies that win are the ones that the market doesn't care about your roadmap.
I remember sitting with the Anthropic team early on and discussing how they thought about why manual outreach wasted my time and what i did instead. Their approach was counterintuitive but brilliant.
What I Tell Founders
When a founder in my portfolio asks me about why manual outreach wasted my time and what i did instead, I usually start with three questions:
- What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
- What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
- Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around revenue intelligence, outbound AI, sales forecasting AI that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But here's the thing about why manual outreach wasted my time and what i did instead: you don't need to get everything right on day one. You just need to get started and keep improving.
The founders in my portfolio who excel at why manual outreach wasted my time and what i did instead share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.