Six Mistakes to Avoid When Taking Money

Founders often sabotage their success by making these six common mistakes

By Chris Kernaghan 4 min read
Six Mistakes to Avoid When Taking Money
Photo by Redd Francisco / Unsplash

Let's be honest. Raising a seed round is a bizarre exercise.

It feels like speed dating, except you're trying to convince a stranger to give you money so you can spend it all very quickly. It's an unnatural process. Nobody teaches this in school. You're trying to sell a dream based on a spreadsheet that's probably wrong.

Because the process is so weird, founders make the same six mistakes over and over again. If you can simply avoid these common pitfalls, you immediately stand a better chance of convincing someone to hand over their cash and join your chaotic journey.

Here are the six most common ways founders sabotage their own success when raising initial capital.


1. Setting the Wrong Valuation

The first mistake most people make is focusing too much energy on a number that doesn't matter yet. You've built a brilliant product and you want the world to recognise its value. Great. But obsessing over a precise valuation too early just slows you down.

Some founders set their valuation too high because they're afraid of dilution. They look at a massive company and demand a similar number. The only thing they achieve is scaring away intelligent investors who understand your actual burn rate.

Conversely, setting a valuation too low is also an error. It attracts what are often called "tourists" or unhelpful investors who simply want a cheap deal. These people are looking for a lottery ticket and won't help you actually build the business.

Your goal at the seed stage is to find a reasonable valuation that attracts the right people. Focus on finding Pre-money fit before you worry about being a unicorn. It's truly a secondary concern.

2. Ignoring the Vesting Cliff

This mistake is common and has cost founders everything. It involves how your equity, or ownership stake, matures over time. You should always have a Vesting Cliff built into every equity agreement, including your own as a founder.

The standard setup is a four year vesting period with a one year cliff. If you grant shares to a cofounder or a key early employee and they leave before the one year mark, they get nothing. That sounds harsh, but it's necessary.

Imagine you bring on a brilliant designer who quits after ten months to go hike the Himalayas. If you didn't have a Vesting Cliff in place, they would legally walk away with a chunk of your company for what amounted to part time work. This happens constantly.

You and your investors need to be protected from a disappearing cofounder who still owns a piece of the company. It's awkward to talk about, but you've got to sign that agreement.

3. Not Understanding the Instrument

A surprisingly large number of founders raise money without fully grasping what a SAFE Note actually is. They know it's not debt and that it's better than a convertible note, but they can't explain why to a potential investor.

The main reason the SAFE Note was invented by Y Combinator was simplicity. It's an agreement that promises the investor future shares at a discount. Because it isn't a loan, you don't have to worry about maturity dates or paying back interest. It makes the conversation fast.

If you're raising on a Convertible Note, you must understand the difference. Convertible notes are debt. They accrue interest and they have a due date. If your company hasn't raised a new round by that date, the investor can demand their money back or convert it into shares at a less favorable valuation.

When you walk into that first investor meeting, you've got to be able to explain exactly why you chose a SAFE Note and how it benefits everyone involved.

4. Confusing ARR and MRR

Most seed stage investors are looking for subscription revenue. They want to see consistent, repeatable money coming in. This is why knowing the difference between ARR and MRR is vital.

MRR is your monthly predictable revenue. It's the metric of choice for smaller consumer apps or businesses focused on month to month flexibility.

ARR is your annual recurring revenue. It's usually preferred by enterprise software companies with long term contracts.

The mistake is claiming ARR when all your customers are paying monthly. For example, if you say you've got 1.2 million in ARR but your customers are paying month to month and half of them churn out by month six, that number is meaningless.

Investors will immediately check your churn rate against your stated ARR. Your numbers must line up. If your growth plus your profit margin doesn't meet the Rule of 40, you need to have a very good explanation for why.

5. Getting Paralyzed by Reporting

You close the funding round and immediately hit the next mistake. You become so overwhelmed by financial reporting that you stop reporting effectively. You confuse action with progress.

The two numbers investors actually care about are:

  1. Runway how many months until you run out of money.
  2. Burn Rate how much cash you're losing each month.

Your investors don't need a twenty-page spreadsheet every week. They need a simple, consistent update that clearly shows the Burn Rate is decreasing (or remaining stable) while your revenue grows.

If you're always late on your updates or can't give a straight answer on how many months of Runway you have left, you're showing your investors that you're a financial liability, not a leader. Keep it simple. Update consistently.

6. Prematurely Optimizing the Wrong Thing

The final and most common mistake is believing that raising money means you've achieved success. You start focusing on hiring executives, getting a fancy office, and writing press releases. You forget the most important thing.

The goal of a seed round is to buy you time to find Product-Market Fit (PMF).

PMF is the one true goal. It means you've built something people desperately need and are willing to pay for. Until you hit that point, nothing else matters. A bad company that has achieved PMF is infinitely more valuable than a brilliant idea that hasn't.

Don't use your seed money to hire a huge sales team. Use it to build a minimum viable product and talk to your first ten customers until they tell you they'd be devastated if your product disappeared tomorrow. If 40 percent of your core users say they'd be "very disappointed" to lose your product, you've found PMF.

Raise your round, be disciplined, and avoid these six mistakes. Now go build that thing.