Hard learned startup lessons

10 short lessons learned from working with others, failing quickly and growing as a product creator.

Over the past year I’ve made an effort to volunteer my time to working with first time founders. Let me be clear, in no way, shape, or form am I a startup guru. Not even close. I simply like to help others get things off the ground because I’ve enjoyed building my own companies immensely and I want others to experience that as well. I’ve provided advice from the front line, helped build webpages, design apps, craft legal documents, figure out how to wind it all down when it didn’t work out as planned and spray paint logos on the wall of the brand new office- I’ll help any way I can.

Through a combination of my own entrepreneurial career and working with others I’ve settled on a list of 10 things to keep in mind when starting a company. I know, I know. Not another listicle. Please god not another fucking listicle. While I agree, I had no other way to organize my thoughts so buckle up for a listicle… ¯\_(ツ)_/¯

I find that these 10 tips apply to every industry, stage of company, type of founder and experience level. I’ll admit I’ve fallen victim to many of these tips myself. Hell, I still do to this day. However, I believe that documenting these sort of things can help ensure that we all stay on the rails and successfully build the thing we’re dreaming about.

Without further ado, please enjoy my top 10 tips for launching your thing!

1. Do your research

Research your idea for four months. I’m serious. Research it for four solid months. I know that sounds nuts but it’s necessary, I promise you.

During those four months you should learn as much as humanly possible about the industry you want to revolutionize or the user whose problem you are going to solve. Even if you’re solving your own problem, research it for four months from every possible angle.

Here’s how you could spend those four months…

Month 1:

  • Write idea down and keep a log of how it evolves. Record every iteration.
  • Google the hell out of it. Get that girl or guy you knew from college who aced every subject to Google the hell out of it for you (shout out to Hannah!).
  • Attend events, listen to webinars, subscribe to newsletters, shop where they shop, eat what they eat. Imagine you’re Frank Abagnale and you needed to perform heart surgery tomorrow as a real life doctor. Your research should be that good.

Month 2:

  • Call and meet with potential users. Talk to them without anything to show. Just talk and listen. You should talk for 10% of the time. Listen as much as possible and record everything they say.
  • Meet with 50 different potential users. Hold yourself accountable and actually visit 50 people. It’s easier said than done.
  • Begin learning who has built something slightly similar to your idea. Create a list of ~20 people you’d love to connect with to learn how they did it. You’ll be surprised how open important people are to connecting to share their story.

Month 3:

  • Learn the economics of your idea. How many of your thing would you have to sell to pay rent? Don’t go crazy with a business plan (or do, whatever works for you) but understand if you’ll have to sell 1 or 10,000 of whatever it is you’re going to make to survive.
  • Begin researching what you’ll need to pull it off. What team members do you need and how many?
  • How much money do you need to pull it off? How much is it if you double it because that’s a bit more accurate.
  • Figure out if you can do it alone or if you’ll need to depend on someone or something else to make it happen (a successful Kickstarter or finding a technical co-founder for example). This is a really big decision so take your time. Deciding to be dependent on someone or something else will have a huge impact on you and your business.

Month 4:

  • Spend the last month thinking about everything you’ve learned so far.
  • Is the idea that strong? Could you do it alone or do you really need someone?
  • A classic startup question is “would you be willing to spend the next ten years of your life on this idea?”… maybe it’s a bit extreme but it’s worth thinking about.

I know four months sounds like an eternity but it’s worth it. You’ll either discover that your idea is terrible or that there is hope. Don’t expect it to be a slam dunk immediately, at this point you’re simply looking for evidence that it solves a real pain point and not that it’s going to get you a Ferrari in every color next year.

2. Reduce how much money you spend

Dig through your bank statement and eliminate every monthly subscription you forgot you had. I was subscribed to a Woodworking magazine for $30 a month (what!?!). Do everything you can to spend as little as possible. You get the gist of reducing how much you spend but unfortunately it’s just as easy to ignore this step as it is to do it.

3. Beware of launching an assumption

Be very careful about launching an assumption.

Assumptions are not properly feared in the startup world like they should be. An assumption will derail your career convincing you it’s the next Facebook. An assumption will drain your bank account and give absolutely nothing back. An assumption will keep you up at night in a cold sweat because you’ve realized your assumption isn’t exactly aligning with what the world wants and you don’t know how to fix it.

That personal agony is not worth it. Trust me, I’ve been there dozens of times but that’s a post for another day.

I agree when more seasoned investors and entrepreneurs say that founder disputes are the number one reason startups fail. However, I think assumptions are the silent killer that no one has really put a face to yet. Thankfully it’s an easy thing to fix, please see step #1.

4. Exercise and sleep

However you prefer to sweat, try to do it a few times a week. Similarly, get consistent sleep each night. Personally, I’ve found that it doesn’t matter that you sleep a lot, only that it’s consistent.

5. Never compare yourself to others

Careful not to interpret this as “don’t look at your competitors”. That should be an obsession.

What I mean by this is, do not compare yourself to other startups around you. I promise, it’s entirely unproductive. Don’t stress about who got funding or who landed that mega deal or who got into YC. Inevitably, you’ll have a close startup friend whose company is killing it before yours is. Put your head down and jam on your product. Simple as that!

6. Don’t wait for the big idea

Don’t wait to come up with the next Uber. Would you wait for the love of your life to knock on your front door? For your dream job to call you at home? For Real Madrid to give you a ring and ask you to play up top with Cristiano? Nah. Go out and grab what you want by launching something small quickly. Everyone calls this approach something different but at the end of the day it’s all about putting an experiment in the hands of your (future) customer to hear what they think.

It’s necessary to say that I am not suggesting that you quit your day job immediately and go all in. See #1 and #3. There are many ways to test ideas without making a huge gamble.

7. Don’t waste time

Time is the most important thing an entrepreneur has. Maybe this one is obvious but it’s easy to get distracted by stupid little things.

There is a great book on this topic called “Will It Make the Boat Go Faster?: Olympic-Winning Strategies for Everyday Success” written by Ben Hunt Davis. You should buy it here.

The Cliff Notes of the book are that you need to eliminate anything that doesn’t make your “boat” go faster. Whenever you’re deciding to do something ask yourself ‘will it make the boat go faster?’. If no, don’t do it. However, please don’t apply this to exercise, social events, personal time or anything similar to that. You need those things to be extremely productive and happy.

8. Avoid the slow no

This is the evil brother of launching assumptions. The slow no can take many forms. It can be a sale that just won’t close or an investor that is dragging you along. Whatever the case may be, avoid this as much as possible. Let me say it again, avoid the slow no at all costs.

I don’t think a one size fits all tip on how to avoid a slow no exists because it always depends on the specific situation. My tip would be to look out for it from the jump and if you think you’re getting a slow no, you most definitely are. If that’s the case, cut it off before it harms you and your company because it will.

9. Be honest with yourself

Never ignore your gut. No matter how big or scary the decision is, never ignore what your body is telling you. It’s amazing what your body knows before an excel sheet tells you.

10. Always be kind

The startup community is tiny. Microscopic at times. Don’t be afraid to speak your mind but always do it with purpose.


I hope you found value in this short list. If so, share your comments below and connect with me on Twitter! ✌