The Top 5 Lessons I’ve Learned As An Entrepreneur (What I Would Tell My Younger Self)

James Ramadan
6 min readSep 5, 2019
Me in Portland

Everyone likes to romanticize being an entrepreneur.

“Living the dream,” they say.

The truth is I am almost certainly in more emotional pain than when I worked in the corporate world. While there are some nice benefits, like increased flexibility, which I appreciate, the fact that I control my hours is a double-edged sword — there is no end work time — no matter how much work I do, it feels like I am never accomplishing or moving fast enough.

I have made mistakes that cost me time and money. I want you to learn from me and my mistakes.

These are my top 5 lessons (so far) from my entrepreneurial journey:

1) Product And Sales Are Your Only Two Real Concerns; Start With Sales

Product and sales are both hard. Each a ton of work.

Coming from a technical background, I was confident that the technical part would be, far and away, the hardest.

I figured, if I can nail the product, everything else will take care of itself. And, if not, I could just pitch a couple of lines and that should do the trick. People will get it! Just take a brief amount of time to understand users and then hit them with your grand product idea!

Wrong!

I was as confident as Gunner Stahl from the D2 Mighty Ducks:

“What if he goes stick side?”

“He’s fancy. He’ll go glove.”

We both know how that shot worked out for Gunner..

Product and sales require persistence, time, and rejection. There are no short cuts in either case: you must face constant rejection — In one case, you are rejected by a computer interpreter telling you that your code isn’t good enough to work, and in the other case, you are rejected by people either explicitly telling you no (which is actually better because then you at least know to move on) or, worse, just ignoring you.

The other parts of building a company like incorporating, building a website, etc. are not as difficult, and shouldn’t be the focus (though still do them).

Don’t worry about investors — they don’t want to invest in you until you have product-market fit and a scalable business model. You need to go sell.

“Don’t sell something you can make, make something you can sell.”

If you are building a technical product, start with sales. The focus should be on your users and their problems. You should constantly be iterating your product after conversations with users. See: lean methodology.

2) Sales Is About Building Relationships NOT Pitching Your Product

This brings me to my second point: how to sell.

I already mentioned my initial lead generation strategy — see someone you think could be interested and pitch a couple lines about your product. As it turns out, this method is highly ineffective because..

NO ONE CARES!

You are lucky if anyone in your industry even wants to talk about your product.

This lesson finally hit me when I was at the restaurant bar pitching my product to a manager, as a sipped on my coke. I was trying to get feedback on my product so I started a conversation with her, and while she did entertain a conversation briefly, after walking away and returning she exclaimed, “you’re still pitching your product!?”

…that was my cue to stop inquiring. At least I enjoyed the coke that day…

If you are trying to pitch a solution when you haven’t yet established a mutual understanding that there is a problem to be solved, you are skipping steps. If people don’t trust you to talk about their issues, you are also skipping steps.

A mentor once told me,

“No one cares what you know, until they know how much you care”.

Truer words have never been said. And this seems to be particularly true for B2B sales.

Nothing lost me points faster with potential customers than continuing to weave my product back into the discussion when they wanted to talk about another problem.

Stop talking, and start listening. Ask the right questions and listen. You need to empathize with your users and their problems and build trust with them so they actually believe that you can offer the right solution.

3) Everything Will Take Longer Than You Think It Will

Frustrating, but true.

Plan accordingly. If you think something will take 1 month, plan to get it done in 3. If you think something should take 6 months, plan for it to take 1 year.

Even for you superstars that work twice as hard as everyone else, things still take longer than you think they will. Trust me.

This fact is especially true for tasks that depend on other people.

I had to go back and forth with Apple multiple times to get my application approved in the Apple Store. Even with some expected delay, the process took 2–3 months longer than anticipated, and I felt dumb when I told people, who I had recently met, that I would show them the app by a certain time and then could not.

“Planning is everything, but plans mean nothing.”

It’s important to plan and prioritize, just remember that patience is a virtue. Be ready to adjust plans when life throws the unexpected at you.

4) Prepare For a Marathon, Not a Sprint

Emotionally. Mentally.

You have no salary. You will be lonely. It is stressful. You will be tested.

It’s ok. So pace yourself.

My initial instinct when I first started was to work myself almost all hours of the week, also known as “ the go, go, go strategy.” I soon realized that this strategy backfired because I would burn out and then shut down for days afterwards due to stress. Weekdays included. Pretty counterproductive.

I finally learned to take breaks when I needed them. I can now sense when I am approaching a breaking point, and I proactively take time to disconnect and take my mind of things.

“Do what you can, with what you have, where you are”. -Teddy Roosevelt

There is no way you should be feeling on any given day. The way you feel is the way you feel. Just accept it, and do the best you can with your emotions and in your current state. It’s good to have goals, but, even if you fall short, you should still be progressing. Remember that. And remember to look back and appreciate your progress too.

5) Only Become An Entrepreneur If You Really Want To Solve a Problem

While almost everyone gets into entrepreneurship for factors like schedule flexibility, control, “perceived coolness”, or money (if we’re being honest), I can now safely say that no one would stay in it for any of those reasons.

You will give up early if one of those is your primary motivation. The emotional and financial disturbances are just too large. It is too easy to look at an alternative timeline where you continue to draw a salary from a company.

The only reason you will stay an entrepreneur is if you become passionate about solving a problem.

And note that I didn’t say, “implementing an idea”. I said, “solving a problem”.

The most common reason tech entrepreneurs fail is because they are passionate about bringing their idea to market rather than solving a problem. They tie their startup’s success to their passion for their idea.

While an idea may be cool/unique/creative, if the market is not willing to pay (enough) for it, it will fail. The idea will become a product that no one wants.

But if you are passionate about solving a problem, and your initial idea fails, the problem still remains to be solved, and you can continue onward with your next potential fix.

Well, good luck! Go chase your dreams! Hope this post has helped!

P.S. I want to send these tips back to myself…does anyone know where I can find a time machine?

Thanks for reading :P

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