Hey, I’m Tim! ☕

When you’re a cofounder, mistakes come at you fast.

I know because when I first started, I made a list. I tried to keep a running tally of everything I’d done wrong or could’ve done better.

I gave up by month 3. The list was growing faster than I could keep up.

Looking back now, I see patterns in those missteps. Most of them fall into 5 categories.

Recognizing them early could save you from making the same ones.

One easy mistake you can prevent is overspending, with the help of Bill.com.

The 5 Fatal Flaws

The danger of a fatal flaw lies in its subtlety.

Often, it’s less of a gunshot to the head and more of a hidden cancer.

They usually stem from chasing the ‘shiny object.’ The vanity metrics. The things that make you look cool.

1. Pride Over Progress

Startups thrive on momentum. Forward motion.

But pride is seductive. You want to protect your reputation but progress demands that you risk embarrassment.

At some point, I’d built a reputation as a CEO. People knew me, I was doing guest lectures at universities, and was invited to be on panels.

That made it all the harder for me to pivot when I needed to. Admitting the need to change felt like admitting failure.

The truth is, clinging to pride did more damage.

People don’t remember your missteps; they remember whether you kept moving forward.

2. Status Over Standards

This relates to the point above.

Chasing status looks impressive from a distance but has no substance.

I stroked my own ego by beefing up my headcount. We probably had 2-3x the people we actually needed. I hired the flashy candidate over the hungry, competent one.

Our talent density decreased as a result. Team members were frustrated and morale plummeted.

The irony is that true status comes from the unsexy work of consistently upholding high standards.

3. Certainty Over Clarity

The desire for certainty paralyzes you.

I burned precious time looking for guarantees even though I knew there were none.

Why? Because I thought I was expected to have all the answers. My cofounders, my team, investors, customers — everybody had questions for me.

And it was just so hard to say “I have no idea.”

It’s so obvious in retrospect that the very places I was avoiding, the uncertain areas, were exactly where clarity was hiding.

4. Agreement Over Action

My team had low diversity of power.

When you’re friends before you become cofounders, it’s natural to highly value consensus and “getting along.” I did that a bit too much.

For the most part, it was productive because we got to stay great friends and hear everyone’s opinion equally. But sometimes, I should’ve been more dictatorial.

I think this is especially true for companies below $1M ARR.

5. Defensiveness Over Dependability

Defensiveness kills trust. Dependability, on the other hand, is born from humility.

There were times when I was sure I had a great idea, but the team wasn’t on board. As CEO, it was tempting to veto them, but that’s not what they needed from me.

They depended on me to listen, weigh their input, and make the best decision.

In the next edition, I’ll dive into the ‘4 Lacks’ that stop this from happening.

Every time you refer someone, you:

1. Look like a genius for finding Cherrytree.

2. Help fellow cofounders build their dream company.

3. Make my day.

Thanks y’all,

Tim He