Essays

How to Avoid the Most Dangerous Mistakes Made by Non-Technical Entrepreneurs

By August 25, 2021No Comments

First, let me get one thing out of the way — as an entrepreneur, you’ll always have problems to solve. It’s what you signed up for. It’s literally the nature of the job. Some examples:

  • Lack of funds
  • Not knowing what to build
  • Not getting interest from customers
  • Fighting off competition
  • Not being able to hire great people
  • Having more demand than you can handle (congrats)
  • …and more

And this is actually good! Solving these problems moves you forward. It’s progress. As long as you stay in business and keep attacking one problem after another, you’ll succeed. Moreover, how you solve them is what makes your unique journey as a founder — even though everyone will give you advice, it’s your personal story. Nobody else can write it for you.

Now, in my opinion there’s also a category of what I consider BAD problems:

  • Being screwed by an investor
  • A team that doesn’t respect your abilities
  • Being betrayed by your partner
  • Getting scammed for your money

I call these “bad” problems because solving them brings zero progress — they only bring you bitter wisdom. They leave you worse off than before you had them, and you have to do a lot of legwork just to get back to the baseline or where you started.

For example, if you get screwed by an investor, it’s typically death to the company. Even if you survive, you rarely feel like it was an opportunity in disguise — you just feel like you woke up from a nightmare that you should never have had in the first place.

Bad problems are best avoided altogether, because dealing with them is a big waste of time — you’re better off working on productive, GOOD problems that move your business forward. Think about that for a second.

Now, where am I going with this?

In this article, I want to give advice around some of these BAD problems, specific to non-technical founders. I hope to save you a lot of wasted time, money and sobbing in the bathroom, so you can build your business instead.

Most engineers love to believe that non-technical founders shouldn’t be starting tech companies at all. I have no idea why this belief is still so popular, when there has been so much evidence to the contrary.

But I will admit that there are certain reasons why “non-technical” founders find it harder to successfully build a tech company — nothing that can’t be fixed, of course, which is why I’m writing this article. I’ll tell you about the major mistakes I’ve seen these founders make, and some advice on what could be done differently.

Let’s begin! I’ll first list all the mistakes, and then talk about prevention measures.

Mistake #1: Hiring an engineer without personally knowing how good they are

Most non-technical founders have no way to judge an engineer’s ability. They fall back on proxy measures like their resume, or a recommendation from a friend (or worse, a stranger), or just a “hunch” that it’s the right person for them (usually heavily influenced by the engineer’s confidence in themselves).

“They worked at Google/Netflix/<insert brand name>, so they must be a safe choice for my business.”

“They’ve built and sold startups before, so they must be really good.”

“They have a lot of experience and are very interested in my business idea, so they’re the perfect choice!”

Well, no. Unless you personally understand and respect their abilities, it will take only ONE surprise — one instance where you’re no longer on the same page — for your relationship to fall into distrust and disappointment.

Mistake #2: Allowing an engineer to make you feel “stupid”

Gosh this is a mistake I feel very passionate about. I’ve met a lot of gifted engineers who take pride in their technical ability, but a small % of them see non-technical people as “below them” in the universal hierarchy.

I’ve seen it happen too many times: a non-technical person will ask a legitimate question or ask why something wasn’t done as promised, and instead of patiently explaining why, the engineer will protect their fragile self-esteem by looking down on the non-techie and almost bullying them into feeling like they have no place asking questions in the first place, because they “don’t understand how things work.”

If you ever find yourself in this situation, let me tell you this — it’s not normal, and it’s not okay.

If an engineer makes you feel stupid or incapable, they’re not the right person for you to work with. It’s THEIR JOB to explain to you how their stuff works, as long as you’re willing to listen and learn and meet them half-way. Don’t ever let them “skirt over” your concerns.

Mistake #3: Not managing the technical expert, because “they know more than me and probably doing their best”

This is closely related to the previous one, but is more your own fault than the engineer’s.

It’s very convenient, and commonly encouraged, for non-technical founders to “fire themselves” from all the technology-related stuff in the company, and let the expert handle the reigns, in the name of “division of labour.”

Often, the technical cofounder is so talented, that the founder believes they’re lucky to even have them, and that it’s foolish of them to “question” anything the techie does or says, let alone manage them.

A lot of non-technical founders fall into this category without even realizing it — they live in denial! A good measure of this is, out of your last 10 conversations with your engineering team, how many times did you actually influence their direction (meaning they decided to do something differently compared to when the meeting began), versus them just telling you how it’s going to be, with you  listening to them without many follow up questions? If it’s less than 3/10, take another look at your relationship objectively.

“Hire for your weaknesses, stay in your lane, don’t dig your nose into matters you don’t understand, let the engineers do their job.”

This is good advice when coming from a place of encouraging trust and avoiding micromanagement. However, this advice often comes from a place of disrespect for the non-technical founder’s authority and the “value” of their opinions on their company’s technical strategy and execution.

If you as a founder take a very hands-off approach, and don’t care to manage the CTO or engineers at all, you can expect to hear more often than not that something which was supposed to take 3 weeks is still unfinished after 12 months (that is not an exaggeration). You can also expect to feel by the end that most of the engineers aren’t even loyal to you, because they don’t see you as the REAL leader of the company.

Please, please, please. You’re well within your rights to manage your CTO, even if they seem much more “experienced” and skilled at their job than you feel at yours. Don’t let your insecurities get in the way of your company’s success.

Mistake #4: Outsourcing the entire development of your “app”

Dev shops and freelancers can be a great resource, and some of them are very good at what they do — no question about that. But if you’re building a tech company, if you think you can outsource the whole “app development” and build a company on that foundation, I beg you to reconsider.

Outsourcing should be for things that aren’t absolutely core to your business — and that includes tech. The CORE of your product should be built in-house, and must never be left in the hands of anyone else.

More often than not, a founder will get an app built by a dev firm to get to market, but as soon as they hire their technical cofounder, the whole app gets torn up and thrown in the trash, and the cofounder decides to build the whole thing from scratch again.

And there are many good reasons for it — for the unsuspecting non-technical founder, the dev firm will usually deliver an app that’s very hard to make changes to, so that the founder has to hire the same firm on a monthly retainer for eternity, just to maintain and fix bugs in the app. A great source of recurring revenue for the firm, and endless nightmare for the founder.

I wrote a more detailed post about outsourcing best practices back in 2016, here: Act like a pro, not a virgin, while outsourcing your software project

Mistake #5: Using the absence of an engineer as an excuse for not getting started

This goes counter to the mistakes above. Yes, it’s hard to hire good engineers and manage them. But that doesn’t mean you give up altogether on your business until you can find someone to build an app for you.

There are plenty of ways to get started on your own and make progress without a professionally-built app.

A lot of founders these days have used No-Code tools to build a rough prototype that works, to get customer feedback and even to make thousands of dollars in revenue, enough to pave the way for the next stage of the business.

Good engineers and technical cofounders want to work with someone who has their sh!t together — you have to earn their services by showing some sort of progress — market validation, funding, revenue, etc. Don’t sit on the sidewalk waiting for the perfect developer to come by before you attack your dreams!

(Most Important) Mistake #6: Not taking OWNERSHIP of your business

All the above mistakes can be summed up into this one. This is entirely psychological. You, as an entrepreneur, need to mentally take ownership of your company.

It means saying, “This is my company. It’s my baby. Even if everyone else leaves and the money dries up, as long as I’m willing to keep working on it, the company isn’t dead. Therefore, it’s also my job to make sure everything is okay.”

This mindset will give you the attitude to avoid all the other mistakes listed above.

So, how can you protect yourself?

Tip #1: Look for the “Heart of a Teacher”

As a non-expert in any field trying to hire someone with more knowledge than you do, this is the BIGGEST quality that can almost single-handedly ensure that you have a healthy long-term partnership.

Your first engineer should have the ability and patience to simply explain to you what they’re doing and why they’re doing it. They don’t get mad or look down on you for not knowing as much as they do.

They actually add value to you and make you better at managing them, every single time you discuss their work.

There are 3 good reasons for this:

  1. If someone loves teaching and is good at it, they’re usually very competent, and have a fairly deep understanding of their field. You can easily separate the bullshitters from the real deal.
  2. Someone with this attitude will be also be a good coach and manager, thus helping you build a team with healthy culture.
  3. They’re usually proactive with communication — if they love teaching, they’ll be excited to tell you about whatever it is they’re working on.

You should easily feel this quality when you talk to them, but for further proof, see if they’ve written a blog or book teaching about their work.

Tip #2: Look for a “Student of the Craft”

While the first tip alone will safely ensure you find a competent person, looking for this second quality will net you a world-class performer.

Being a “student of the craft” means someone who is always seeking to get better at their job, as a general attitude. They treat their profession as an athlete or scientist — always figuring out how to improve their performance.

Every single top performer I’ve ever seen, in any discipline is a student of their trade. No exceptions.

It’s a chef who spends a lot of time experimenting in the kitchen, trying new ingredients and recipes, and also traveling around the world to get better at their craft. It’s a filmmaker who watches as many movies as she can to learn new tricks from her peers. Or the engineer who’s excited to read the latest book about a new technology.

A clear sign of this is to ask them, what have they done or learned recently that helped them improve at their craft? (It could be reading a book, practicing a certain skill deliberately, etc.)

Or, what could they work on to improve? (True students of their craft ALWAYS know their weaknesses and key areas of improvement, and have a reason explaining why.)

Another excellent question is, “what is your daily routine as a professional in your field?” A routine is the fundamental infrastructure of any profession. Every top performer has one, along with reasons for why they have it. They also know what’s NOT their ideal routine (because they’ve probably tweaked and tested their routine many times).

Tip #3: Become “Technically Fluent”

Technical fluency means you have a solid understanding of how the tech works, the big moving parts, and what you should care about. You should be able to ask good questions and weigh in on high-level strategic decisions relating to the technology, even if you aren’t a great programmer yourself. It will also help you avoid blatant scams and call bullshit on people trying to take advantage of your lack of expertise (ever visited a car mechanic without knowing anything about car repair/maintenance? It’s not fun).

It doesn’t apply only to tech. Take finance for instance. I’m not a finance professional, but as a CEO I’ve taught myself the fundamentals from a strategic standpoint. I can read an income statement, I know the major types of accounting frauds/mistakes and how to avoid going to jail, and I know what to look for while analyzing our burn rate and economics as a business.

Or, consider that billionaires who own sports teams aren’t professional sportspeople. They hire coaches for their teams. But they understand the sport deeply enough to make big decisions about players and the way they manage the team!

A lot of decisions we have to make as CEOs/founders are strategic. Have an informed strategic opinion on every aspect of your business!

Here’s a free essay to help you get started: The Non-Enginer’s Ultimate Guide to Software Technology

Good luck!

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