How to Make Smarter Start-up Decisions

Overnight success is usually a myth and creating a successful start-up involves thousands of tiny decisions aggregated into one giant whole.

What do you do when you’re stuck on a problem and can’t come to a decision though? Rarely will one decision kill your start-up, but it could set you on a wind-about path and cause you to lose time.

These are techniques I’ve realized work for me over the years and I’ve decided to share. I would also love for you to share your methods for making smarter decisions with me in the comments.

Tip #1 – Take a Break and Relax

This may sound counter intuitive for actually reaching a decision, but letting your mind drift and your ambient thought process run can actually make you a more productive decider.

How many times has this scenario happened to you? You’re busy coding away and having a productive night, and then hit a problem you can’t quite figure out. Two hours later, you’re still hacking on the same issue. You feel like you’ve tried everything, and then find yourself trying the same things over again. Frustrated, you head to bed unsatisfied, only to realize a simple solution existed the next morning while taking a shower.

I believe our minds have the ability to sub consciously problem solve, taking in and processing much more information more efficiently than when we are stimulated by the world around us. When you let your mind drift, you can solve problems you wouldn’t otherwise be able to solve when you’re distracted by daily life.

I don’t suggest watching TV or playing video games when trying to solve a hard problem because your mind is unlikely to drift and relax by those stimulating activities. When trying to make a tough decision, take some time to recharge your brain’s batteries by going for a jog, reading a book, or getting a beer with a friend. You’ll be amazed at how clear headed you become once you take a step back.

Tip #2 – Sleep at Least 8 Hours

You wouldn’t want to compete in a race on a half night’s sleep because your body would be tired, so why would you try to compete in the start-up world when your mind is tired?

The benefits of sleeping enough not only help you, but also help your start-up. Sleep deprivation clouds your ability to make decision, and can even cause you to be overly optimistic. You’ll also be more pleasant to work with, allowing your team to make better decisions because they don’t have to deal with your crankiness. Make decisions for your start-up when your brain is 100% charged and ready to think.

Tip #3 – Know When You’re in the Weeds

“In the weeds” is a termed used in the restaurant industry for when you are overwhelmingly busy, are doing a poor job executing on your responsibilities, and are likely to keep doing a poor job because you can’t catch up.

The start-up weeds are no different and they can slowly kill your company. When you’re in the start-up weeds, you’re still moving forward, but moving very slowly and making almost no meaningful progress on a daily basis.

It’s not easy to know when you’re in the start-up weeds. A quick test I like to use to check if you’re in the weeds comes from Steve Jobs:

“When I was 17, I read a quote that went something like: “If you live each day as if it was your last, someday you’ll most certainly be right.” It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today? And whenever the answer has been “No” for too many days in a row, I know I need to change something.’ – Steve Jobs

Getting out of the weeds will help you make smarter decisions because your emotions will be at bay and your judgement will not be clouded by day-to-day problems. Escaping usually involves making a hard decision or two. You may need to better train or fire an employee. You may need to fire a customer that requests an excessive amount of personal support. You may need to think about pivoting your product to be simpler.

If you’re in the start-up weeds, take a day off from work and remove yourself temporarily from the problems that are causing you stress. This will help you conserve your mental and emotional energy, and create an escape plan.

Try to examine the root cause of why you’re having issues in the first place. Suppose you have excessive amounts of customer support to do everyday. The probem could be caused by bugs, which force people to contact you. Fix the bugs, and your customer support problem is solved. Perhaps your customers just don’t understand how to do use the product. You could make some short video tutorials to scale your support. Or maybe your customers aren’t using the support forums. Do customers even know where the support forums are? You could add a link into your product that customers won’t miss.

If you keep asking yourself why you’re in the weeds in the first place, you’ll eventually backtrack to how you got there, and can set out on a journey to get out.

Tip #4 – Go with your Gut

If you ever read Blink by Malcom Gladwell, you’ll know your gut is actually a sub conscious collection of all the experiences you’ve had in your life, which can be used to help you thing slice situations and make smarter decisions. More and more I’m learning to trust my gut and avoid poor decisions in the first place.

It’s much easier for someone you are actively working with to kill your start-up than for someone who is not involved at all. If an employee, investor, or vendor just doesn’t feel right, then don’t work with them.

Tip #5 – Hang out with Smart and Motivated People

Humans have a natural tendency to act like the people we associate with. Hanging around people who are constantly drinking and doing nothing will most likely cause you to drink and do a lot of nothing.

The good news is you are not forced to be friends with specific people, and have the opportunity to fraternize with smart and motivated people. When you surround yourself with smart people, you’ll naturally sponge up new information and ideas from them. When you are friends with smart people, you can ask for advice on hard decisions. When you hang out with smart people, you will naturally work as hard or harder than them to keep up.

Your parents have been telling you for years to avoid peer pressure, but in reality it’s nearly impossible to avoid. The best way to combat peer pressure is to just hang out with people who are smarter than you, and allow them to pressure you to be better. Do not underestimate how much personality you absorb from your peers, which is then baked in your product, start-up culture and every decision you make.

Please let me know what you think below or share your methods for making smarter decisions. I’m new to writing, and greatly appreciate any and all feedback.

How to Kill Start-up Distractions

Start-ups are hard, but there are a few things that you can do to make your life simpler and give your start-up a better chance of success.

These are lessons I’ve picked up along the way and now live by to simplify my life and optimize the amount of time I have to work on my company.

Side Start-ups are Poison

If you are a start-up founder, you should not have any other companies you work on. Do not start hacking on a new start-up idea. Do not get involved with anyone else’s companies. Do not even start thinking about other ideas unless you are ready to permanently throw in the towel on your current start-up.

Start-ups take a tremendous amount of energy and time to succeed, and by splitting your resources between multiple start-ups, you’re guaranteed to have a lot of of unsuccessful and half baked companies.

This doesn’t just happen to “bad” entrepreneurs. Lack of focus happens to almost every founder.

“After my first company died, I did an inventory of the projects I had worked on in the last year. There were something like 30 projects that I had started on and not finished. My total weakness was focusing on things.”
- Ev Williams, cofounder – Twitter

If you are tempted to start something new, here’s a good test. Keep track of where your mind is drifting to on weekends, in the shower, and when you sleep. If you are not thinking about your current start-up constantly, then it’s time to move on. Most start-up founders do not suffer from a lack of amazing ideas, they suffer from a lack of focus. If you stay focused, you’ll be unstoppable.

Also, I used the term side start-up above deliberately and I am totally fine with founders having side projects. In my opinion, a side project is something you work on in your spare time to hone your skills, learn and have fun. You should have no responsibilities to customers, employees, or investors on a side project, which is what makes it different from a side start-up.

Usually side projects help you learn something new that you can incorporate back into your start-up.This blog is a side project of mine that I use to improve my writing skills, help others, and archive my ideas. If I decided to close down shop tomorrow because it was making me stressed, I wouldn’t be letting anyone down.

Hell Yeah, or No

It took me too long to realize that my time is my most valuable asset. My start-up is all consuming, so when I agree to do things for other people on top of my already busy lifestyle, that is taking away from my leisure time. When I do not have leisure time, I do not think clearly and make poor decisions, thus hurting my company.

Derek Sivers introduced me to the concept of “Hell Yeah, or No” in his book Anything you Want (highly recommended). The basic idea is that if you aren’t thinking, “Hell yeah I want to have a meeting with you!”, then you shouldn’t take the meeting with the person who asks.

This rule has not steered me wrong yet, and has gotten me out of countless meetings and distractions that I would have regretted doing later on.

Let Your Customers Captain the Ship

There’s no better way to stay focused than to talk to your customers. Talking to your customers is never a waste of time. Your job as a start-up founder is to build an amazing product and sell it. By talking to your customers, your biggest issues and main priorities will automatically bubble to the surface, keeping you focused and on track.

Respect the Headphones

As a start-up founder, you have the opportunity to set the culture of your company. Building a respectful workplace free of avoidable interruptions is very important. Teach your employees that when someone has headphones on, you should avoid interrupting him at all costs. Being in a state of flow is when you are most productive (and scientifically proven to be happiest).

This concept was referenced in the Social Network as being “wired in,” and I 100% agree with it. Even if it’s inconvenient at first and kind of socially awkward, just try it out and you’ll quickly see gains in productivity across your entire company.

Use Chat

My cofounder and I communicate through chat during the workday whenever possible. When we had interns this summer, we asked them all to use chat and not interrupt us and each other. Compare the two scenarios below:



Bill: Hey
Ted: (ignores because headphones are on)
Bill: (wheels over, hits on arm)
Ted: What?
Bill: Do you think the sign up button should be green or red?
Ted: Red because…(2 minute explanation)
Bill: Ok – thanks (wheels back)

Bill: What color do you think I should make the sign up button?
Ted: red –

The talking scenario could take a total of 10-15 minutes for Bill to focus back on his work. The chat scenario takes 30 seconds total to finish, and because the interruption was shorter, getting focused again will not take as long.

Work Odd Hours

If all else fails, you can always try working early in the morning or late at night. These are times when the Internets are slowed down and there will be less tweets and post on HackerNews to read and be distracted. You’ll also be free of phone calls, text messages, and people wanting to bother you.

Start-ups are about moving as fast as possible. If you avoid distractions that slow you done,
you’ll greatly increase your chances of survival.

Do you have any tips or stories about how you killed distractions from your life? Share in the comments below.