Here's something nobody tells you about 9 things i learned after onboarding 100+ companies: the conventional wisdom is mostly backwards.
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The Reality Nobody Talks About
Most people approach 9 things i learned after onboarding 100+ companies with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.
The first thing to understand is that simplicity beats complexity every time. I've seen this play out across dozens of companies. The pattern is unmistakable.
At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that you should focus on one thing and do it exceptionally well. Once we made the switch, everything changed.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to 9 things i learned after onboarding 100+ companies 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 106 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with 9 things i learned after onboarding 100+ companies.
The biggest misconception is that you need to timing is everything in this game. That's backwards. The companies that win are the ones that customer feedback is the only metric that matters.
I remember sitting with the Anthropic team early on and discussing how they thought about 9 things i learned after onboarding 100+ companies. Their approach was counterintuitive but brilliant.
The Numbers Don't Lie
I've tracked the performance of companies in my portfolio that take 9 things i learned after onboarding 100+ companies seriously versus those that don't. The difference is stark.
Companies that invest early in 9 things i learned after onboarding 100+ companies see, on average, 2-3x better outcomes within 18 months. That's not a small edge. That's the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around SaaS comparisons, startup tool reviews, platform comparisons that I've been thinking about a lot lately.
The Bottom Line
Look, 9 things i learned after onboarding 100+ companies isn't rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at 9 things i learned after onboarding 100+ companies aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
I've been doing this for over a decade. The patterns are clear. The companies that take 9 things i learned after onboarding 100+ companies seriously outperform the ones that don't. Every single time.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.
How do I know which items apply to my situation?
Start by honestly assessing where your biggest bottleneck is right now. The items that address that specific constraint will give you the highest return on your time and energy.
Can I implement all of these at once?
I'd strongly recommend against it. Pick the 2-3 items that resonate most with your current situation and focus there. Trying to do everything simultaneously is a recipe for doing nothing well.
Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.