Over the past 5 years, my digital marketing agency, K&J Growth, has run 200 custom marketing campaigns for companies of every color and creed. 

We’ve spent tens of millions on advertising channels of all types and had 10s of ‘growth hacking’ breakout successes. Including working for TikTok during their hyper-growth period. 

Over the years, I’ve seen venture-backed companies make annoyingly stupid decisions that do nothing but burn money like their secretly anti-capitalists, as well as founders that bootstrapped their way to the glory land. 

I’ve also seen the reverse. Venture-backed companies grow wildly fast, and bootstrappers make poor decisions with their limited cash. 

Over the years, I’ve used my proximity to these businesses as a crash course on mistakes business owners make in the pursuit of the dream. 

Some of these points will contradict each other. That might be annoying, but the reason for that leads me to mistake number 1.

1. Don’t Over-generalize Generic Advice.

This comes from neglecting to recognize that your situation is always unique. Just because you heard on a podcast that you should be doing something doesn’t mean that it is the right move for your business at this particular time. 

You don’t need to raise money just because everybody else is. You don’t need to invest in SEO just because it’s a highly regarded marketing channel. You don’t need influencer marketing because that’s hot right now. Don’t get out there and sell if you don’t feel your product is ready. Don’t try to shove some Web3 adaptation down the throat of your business that shouldn’t be there. 

If you can’t do your own strategizing, you should go back to being an employee. 

2. Overbuilding.

It’s a natural part of our human nature to want to keep building. 

Do your customers love your first product? Well, why not add to it? 

Do they love the software? Put three more features on the roadmap. 

It feels like the natural next move. But it might hurt your business. When you are constantly trying to add, it won’t take long for you to have too much on your plate. 

Let’s be honest. You might have a good product. But couldn’t it be better? Should you start working on the next part of the business when you haven’t yet fixed all the kinks? Be careful when you’re focused on adding, not to forget what brought your customers to you in the first place. 

3. Overselling.

This is usually the fault of the sales-first type of founders. Lots of companies live and die by the sales strengths of the founder. The problem comes when the founder or salesperson starts selling more than there is to be sold. 

Just because you have a prospect in front of you doesn’t mean you should make a promise you can’t keep. This might look like promising features that don’t exist for enterprise clients. Or singing orders with retailers your suppliers can’t fulfill.

Like the problem of overbuilding, this is an issue of overextending yourself. It starts as a solution for a lack of revenue, but then expenses grow to compensate for the operational strain. It becomes a never-ending cycle that’s hard to get out of. 

4. Invest in Anything Other Than Education.

For example, if you’re investing in an ad campaign. You’re not investing in ads. You’re investing in data. This is just semantics, of course. The point is when you invest any part of your business, this should be seen from the lens of an experiment to get educated. 

If you take on this mental framework, you’ll start to invest differently. You’ll invest with the expectation of failure. That might seem self-defeating, but in reality, it’s the safest way to ensure success. It stops you from ever putting too many chips in one basket and forces you to back up your big decisions with data from your experiments. 

5. Market When You Should Be Selling.

Marketing is just the scalable version of 1-to-1 sales. But if you haven’t done the 1-to-1 sales, you shouldn’t do the marketing.

There is no place in your business more likely to waste money than marketing. How do you stop yourself from wasting your time and energy in marketing that is bound to fail?

You do it by selling first. By reaching out to potential customers 1 by 1 and selling to them. Asking them to buy your product. Even if it’s only a $5 product. What you want from this more than anything is to hear ‘why’ from the people who don’t buy. This will give you the tools you need to succeed in your marketing. Or better yet, it will convince you to just kill this business before investing anything else into it. 

6. Delegating “Trivial” Work Before Understanding The First Principles.

The better you understand any skill, the more efficiently (read: cheaply) you will be able to delegate that skill. 

I’ve lost count of the would-be entrepreneurs that were stopped in their tracks on the simple project of building a website. They find a developer to build it for a few thousand dollars to save themselves the headache. But then, like any project birthed out of vague expectations, it goes sideways. 

The developer isn’t a designer or copywriter and doesn’t know much about why you need a website built.

What was supposed to be an easy transaction: a few thousand dollars to save some headache, becomes an even bigger headache and at least a few more thousand dollars. 

The website is a metaphor. Each of these people could have saved themselves thousands of future expenses, not to mention the gains if they had spent 10 hours first trying to build it themselves. 

As a rule, the more detailed you are in your instructions to people you delegate to, the cheaper it will be. 

7. Leaving Time on The Table as Opposed to Money.

You’ve heard the saying, “don’t leave money on the table.” Well, sadly, a lot of people trap themselves using this archaic cardinal rule. 

The Zen Master Jedi Mode for entrepreneurs is when they have figured out where they should be spending their time, so it has the highest possible impact. 

Generally, that means, more than anyone else in the company, founders are focused on the long-term impacts of their work. More often than not, things that are productive in the short term come at the cost of the long-term objective. 

In other words, you should seek to leave money on the table, in the short term, in favor of time spent working on the long-term objectives. 

8. Act On All Customer Feedback.

The true asset of every business is its customers. Products can be copied. The relationship between you and your customers is hard to take away. 

That said, take your customer's feedback with a grain of salt. Be very careful assuming one customer's feedback extends to the rest of them. Generally speaking, your dissatisfied customers will be the loudest. If you listen to them and institute a change based on their feedback, it might come at the cost of moving away from what happy customers found perfect for them. 

Don’t penalize satisfied customers for not bothering you in favor of whiney dissatisfied ones. 

9. Innovate Where The Market Wants Familiarity.

It’s common practice in UI/UX to put common buttons in common places. For example, if you need a settings button on your software, the best practice is to make the icon a cog and put it in the bottom left corner. 

One of the reasons crypto and web 3 projects have trouble getting mass adoption is that they are foundational changes to how people interact with common problems. My mom already struggles with online banking. She knows how to log on and do basic stuff but is easily stumped. In which case, she’ll go old school and call a banker. 

Never will she be able to figure out setting up MetaMask and using that to store her wealth. 

If you want people to be able to jump right into using your groundbreaking product, you need to innovate in select few places. Everything outside those select few places should feel extremely familiar to the user experiences they already know.

10. Say Yes to Random Opportunities You Didn’t Plan For.

Once you have traction in your business, people will come at you left and right with opportunities to apply your business in ways you didn’t think of. Ignore these. 

In no circumstances should you rely on the randomness of opportunities to be successful in your business. If you find yourself in this position, you need to sit down in quiet and do more strategizing. Typically, if you are not confident in your own plan, you will allow yourself to be grabbed by shiny objects. But you don’t know where this leads. It may seem like a good idea, but you release control when you do this. 

You should always be the one with the plan. Even if you can’t let it outwardly appear that way.

11. Make Things Unnecessarily Complicated.

Complicated plans, workflows, or strategies are a manifestation of insecurities. It was either Warren Buffett or Charlie Munger who said, diversification is for people who don’t know what they are doing. People who do know what they are doing put all their eggs in one basket and then watch that basket closely. 

In other words, when anything has too many pieces it is usually because the builder is not certain which pieces are important and which ones aren’t. It’s your responsibility as a founder to catch this as it’s happening and make fewer, but better decisions. 

The simple way to make things simpler is to focus relentlessly on deleting things that aren’t necessary. 

12. Fundraise Before You’ve Bootstrapped.

A lot of founders fundraise before they even know if their business can get traction. I’m not saying that you should bootstrap thick and thin. But you should do the foundational work to ensure a market for your idea before you take other people's money. 

When you get into the fundraising world, you’re putting yourself in a position where you have 2 customers with very different incentives for supporting you. You’ll have to do a lot of additional work to satisfy both customer segments. If you are going to fundraise, you should be sure that you have a model that can keep the promise you are making to the original customer before taking on a second customer.

Sahil Lavingia went through a crisis and almost trashed his tech startup, Gumroad, because he couldn’t satisfy his investors. He had a perfectly stable business once he ditched the investors and focused on satisfying his customers. Investors can apply needs on a business that aren’t there otherwise. Be careful adding those needs in the mix.

13. Invent a Process a $150 Course can Teach You.

As a systems thinker, this one is personal. I’ve lost count of the times I’ve tried to figure out someone on my own, just to have a relatively cheap course mirror my ignorance back to me. Now, when a strategy I’m pursuing employs a certain tactic, I start by looking for a course from an expert on how to do it well. It’s saved me much headache. 

This is about using the Information Revolution to your advantage. The internet doesn’t just give you tools of incredible leverage, it allows you to access the knowledge of the entire world. Get good at finding the pieces of knowledge you need via the infinite internet and applying them to your situation. 

Don’t invent a new process until you’ve learned someone else’s version. Then, when you are very knowledgeable, you can reinvent from scratch from first principles.

14. Scale Just Because You Can.

Often, people feel urged to scale their business for different, but bad, reasons. Sometimes it's nothing more than the faint understanding that that’s what they’re supposed to do. Sometimes it's because they have figured out a profitable customer acquisition strategy. 

Don’t let the marketers on your team, or the marketer inside of you, determine when you should scale. When to scale should be decided by your inner COO or CFO. In other words, you should scale when you have a profitable customer acquisition strategy, AND the operations of your business are scalable.

That’s the missing piece most people miss. 

Final Thoughts

There you have it.  These are some of the 14 most common mistakes that I’ve seen over the years. Keep in mind, these might not be mistakes in your business. 

Remember that your business is your business. Nobody does, or should, know it better than you. Don’t make the big mistake of doing something because that’s what’s best for someone else’s business.