Why Start-Ups Succeed: Top Tips for Entrepreneurs

Updated: May 23, 2021

People love to write about why start-ups fail. Maybe you’ve seen the statistics, or maybe, like Han Solo, you prefer not to be told the odds.

Either way, I’m not actually here to tell you why so many startups don’t succeed. I’m here to tell you why a few of them do.

For the last six years, I’ve been helping start-ups grow from seedlings into successful companies. Two of the companies I’ve worked with, PlayFab and Qualtrics, were ultimately acquired by major corporations (Microsoft and SAP, respectively). Others are still out there, growing and thriving on their own terms.

In helping these companies find their footing, hone their brand voice, and craft their unique culture, I’ve come to recognize certain practices that are harbingers of eventual start-up success.

May these tips help you reach all your big, hairy, audacious entrepreneurial goals!

1. Attitude

It all starts here

The single best predictor of success or failure, in my experience, is the attitude of those involved.

Here are some attitudes you’ll need to adopt if you want to beat the odds.

It may not be our fault, but it is our responsibility.

This is true across every aspect of life. We have no control over the cards we’re dealt, only how we choose to play them.

When calamity strikes and your best laid plans go awry, don’t waste time assigning blame.

Just jump on in and start fixing it.

Example: the most important conference of the year (GDC) was in just a few days, and I was 100% sure I ordered 200 T-shirts, but only 80 showed up.

Sure, I could have wasted time pointing fingers or digging through emails to figure out who dropped the ball and where, but the bottom line is that we needed more T-shirts, stat. So that’s where I put my energy: toward getting more T-shirts rush ordered and shipped directly to the conference.

Ask forgiveness, not permission

Honey badgers ask forgiveness, not permission

One of the most important skills for succeeding in Startupland is a bias for action.

The most efficient teams are those whose members feel empowered to make quick decisions.

Yes, mistakes will be made. But you won’t stagnate and everyone involved will learn something new.

“Yes, if…”, not no 

Instead of focusing on why something won’t work, focus on what resources, etc., would be needed in order to make it happen.

No is the end of a conversation.

Yes, if is the beginning of a negotiation.

The fastest way to grow is to go in over your head on purpose

Motivational speaker Dan Thurmon tells a great story about learning to juggle. He had three balls down cold, but was still struggling to master juggling with four.

That is, until he started trying to learn to juggle with five. Then, suddenly, juggling four balls became a piece of cake.

Counter-intuitive as it may seem, sometimes adding even more complexity or taking on even bigger challenges is the best course of action when you’re struggling. The only way to get un-stuck is to move forward, full speed ahead.

As the old adage says: the only way out is through.

Focus determines reality

That means that the more focus you put on the things you want to be real, the more real they will become.

Meanwhile, what you resist, persists. The more energy you pour into pathologizing problems, the more problematic they become.

In other words: focus on what you want, not what you don’t want.

2. Business practices

Build a business that works

Create a mastermind partnership

One of the most under-valued commodities in business is partnership.

We all have unique strengths and gifts; I guarantee there is someone out there who compliments yours perfectly. The right partner(s) will shore up your weak spots and allow you to shine, exactly as you are.

Find the person or people who make you better at what you do, who share(s) your passion for the mission at hand, and whom you can trust implicitly. Then let them all the way in.

Bring real value to your target market

So you’ve got this great idea, and you’re convinced that it’s going to change the world.

You put everything you’ve got behind it, and yet, somehow, it still isn’t thriving.

Why? Because you skipped an incredibly important step: determining product-market fit.

It doesn’t matter how clever your idea is. If nobody really needs it, they aren’t going to pay for it. Period.

The answer is to focus first on proof of concept.

Try this exercise:

Come up with at least three different, but related, ideasMake a simple landing page for each oneNotice which page gets the most web trafficStart pouring resources into that oneAdjust as needed.

Little by little you will discover which problems are the most pressing for consumers and come up with a solution that is genuinely valuable to them.

And once you’ve done that? You’re golden.

Come up with an ordered list of service priorities

In order for an entire organization to stay aligned, whether it’s a two-person mom & pop or a huge corporation, you need to agree on service priority order.

For example:

Whenever you’re faced with a tough business decision, refer to this list and make sure your actions reflect these priorities, in this order.

Under-promise and over-deliver

It is your job to set expectations for customers, vendors, etc.

If you promise them the sun and moon, even if you deliver them the moon, they’re going to be disappointed. But if you tell them you *might* be able to get them a mid-sized asteroid, and show up with the moon, you’ll be hailed as a goddamned hero.

Reaching for the moon

Reputation / word of mouth is everything

No business succeeds without earning customers’ trust. Every time you take an action, no matter how small, ask yourself if it will strengthen or weaken that trust.

You can never un-do an untrustworthy act, so err on the side of caring. Always.

Believe the big lie

A start-up, as opposed to a small business, is designed to grow.

Think of your company not as a seed with the potential to blossom, but as a fully-formed tree in full bloom.

If you see success as inevitable, others will too.

3. Company culture

Create a culture you're proud to be a part of

Values are key

Choose your values carefully, and post them prominently.

Your values are your company.

Cultivate a deliberate company culture

Every company has a culture. If you’re not deliberately cultivating a culture that reflects your core values, a culture will develop nonetheless. Just not necessarily one you want to be a part of.

Talk about culture. A lot. Make sure everyone on the team understands their role as a cultural curator, too.

Hiring: intelligence, attitude, and trustworthiness outweigh experience

Everybody is looking for a unicorn: that magical someone with a resume that is an exact match to their job description, AND who is a great culture fit, with plenty of growth potential.

Chances are, though, you’re going to find someone who is one or the other. Either smart, scrappy, hungry, and eager to learn; or preloaded with the requisite experience and skill-set.

Go for the one who is most passionate about the role and the company. Everything else can be taught.

Hire for strengths, not lack of weaknesses

Nobody is perfect. Everyone has flaws. The more you focus on those flaws, the more impossible you will find it to make a hire.

Focus instead on strengths. Who has the strongest skills in the most critical areas? The rest can be shored up over time.

Stay leaner, longer

It’s very tempting, once you have funding available, to fill every open position immediately.

But the best people are not generally available on a moment’s notice. You may find yourself filling seats with warm bodies, rather than holding out for the right fit.

Hasty hiring often leads to cascading culture problems. Those take a lot of time and energy to repair, if they can be repaired at all.

Err on the side of caution. Make the best use of the resources you already have, and hireA-players only.

Hire slowly, fire quickly

I know, I know: you feel like you need someone yesterday. You’re stretched thin, and desperate to find a worker bee to start taking tasks off your plate. But a bad fit will create *more* work for you, not less.

Take your time. Only make a hire when you’re convinced they’ll bring you value from day one.

If you see that it’s not working out, intervene immediately. Give direction, and set clear expectations (Radical Candor is an excellent resource on how to have these tough conversations). Then watch closely.

If they still aren’t performing up to your expectations, let them go. It’s no fun, but it’s better for all involved. And it only gets messier the longer you wait.

The truth is, people know when they’re not performing well. It doesn’t feel good to them, either. And if you’ve ever had to work with someone whose competency was less than stellar, you know what a profound effect it can have on the rest of the team.

When you fail to intervene, you not only bring down the productivity and morale of the entire organization, you condemn the low-performer to a perpetual state of stress, self-doubt, and lack of motivation. Besides which, it’s your job to maintain high standards.

Pay attention to red flags

If even one person on your team is uncomfortable, don’t dismiss their input.

Picture this: you’ve been looking for months to find a good PM. But candidate after candidate has been a disappointment.

Finally, you find someone with all the right qualifications, and he gets the thumbs-up from all your employees. All, that is, except one. This lone dissenter writes on her feedback form:

“I can see that [name] is talented, but the way he interacted with me was… disturbing. He was dismissive, condescending, and inappropriate. Not only did he assume I can’t code, he asked me where I live and suggested we could carpool. It put me in the awkward position of having to reject his offer (because, dude, I don’t know you, I’m not getting in your car), and created a tense atmosphere for the rest of the interview. Please don’t hire this guy.”

It may be tempting to sweep that one thumbs-down under the rug in light of all the other thumbs up. But that one dissenting voice can help you dodge a potential bullet down the road.

4. Management

Don't just manage. Lead.

Transparency is a must

You want all your employees to think like CEOs, and they can’t do that without all the same information the CEO has access to.

If you can’t trust your team with sensitive information, you need a new team.

Don’t hang the messenger

If you do, you’ll never hear bad news again. And without bad news, you won’t know where improvements are needed.

Don’t harp on mistakes

Instead, celebrate saves and solutions. Keep that growth mindset and encourage your team to do the same!

If you find yourself micromanaging or being overly critical, there’s a trust issue that needs to be addressed.

Managers often need to be the bearers, or recipients, of bad news. It just comes with the territory. So set aside time to share good news and praise on a regular basis. You’d be surprised how much good news and praise-worthy activity you can find when you start looking for it!

5. Team spirit

How to be an asset on any team

Be a winner, not a whiner

Never bring a problem to the team without at least one suggested solution.

Push back

Don’t be a yes-man. Offer your unique perspective, even if that means pushing back against something the rest of the team is on board with.

Likewise, when you’ve been tasked with getting something accomplished, and you encounter a stumbling block, don’t just give up and go crawling back to the team saying, “Sorry, I tried, but they said no.”

Instead, find out why they said no. What are the obstacles standing in the way of a yes? Once you have that information, you can work on coming up with a plan and proposing alternate solutions.

Question everything

It’s always tempting to simply accept the status quo as a given and avoid rocking the boat. But a fresh perspective may be just what is needed to solve a long-standing problem in the marketplace.

Don’t be shy to point out bugs in the system, or to interrogate those in charge. And don’t take, “That’s just the way it is” for an answer.

Own up to mistakes

As soon as you realize you’ve taken a wrong turn, ‘fess up immediately. Then explain what you learned, and what you’ll do differently next time. Then do it!

The only truly egregious mistakes are the ones you make more than once.

6. Personal Productivity

Get. Shit. Done.

Measure twice, cut once

It’s crazy how much this simple phrase changed my working life.

Yes, it’s annoying and feels slow to double check all your work. But it takes FAR less time (not to mention stress) to do a spot check before you pull the trigger than to have to do damage control after the fact.

This is especially applicable when you’ve already made a mistake and need to fix it. Nevertry to fix a problem from a place of panic.

If your adrenal system has taken over, you will have a severely reduced capacity to reason, and are likely to make poor judgment calls and make more mistakes.

Step back. Look out a window. Take some centering breaths. Think about a time when you achieved success. Focus on that feeling of confidence and competence. Take a short walk if you can.

Whatever you need to do to get into a better headspace, do it. Then fix your error, and this time double check your work!

Write everything down

No matter how good your memory is, when you’re surrounded by randomization and stimuli, something is bound to fall off your mental list.

Always keep a written task list, either in electronic or analog format. A small notebook that fits in your pocket, an app on your phone… whatever works for you. Every time something comes up, even if it’s just a quick task you can take care of right away, write it down.

This will ensure that you stay on task without letting anything slip through the cracks.

It also has the extra side benefit of providing a record of everything you do.

And I must say, it feels incredibly satisfying to mark off all those tasks as you finish them.

In meetings, leave your laptop at your desk. Bring a notebook and a pen, instead. You won’t be distracted by emails, etc., and can focus completely on what’s being discussed.

Taking analog notes engages your brain in a more powerful way than does typing. Increase your recall and forge unexpected connections with hand-writing.

If you don’t know, say so

Nobody expects you to be omniscient. They do, however, expect you to ask for information when you need it.

Whenever you don’t understand something, ask.

People like to play expert and share what they know, so you’re doing them a favor. Seriously.

Whenever someone asks you a question you don’t know the answer to, simply say you don’t know. If applicable, assure them that you will find out. There’s no shame in not knowing, only in not doing the work to find the answer.

And remember: someone always knows what you need to know. You just need to figure out who, and how to contact them.

Multitasking is a lie

Turns out there’s no such thing as multitasking.

The brain can’t actually do two things at once. It can switch back and forth rapidly from one thing to the other, but that is a very expensive way to work, energetically speaking.

It is far more efficient and effective to list your tasks in priority order, and simply focus on one thing at a time.

Your email inbox should NOT be your to do list

A lot of folks use their inbox as their to-do list. This is a bad idea for several reasons:

  1. Tasks are not listed in priority order, but simply the order they arrived in.

  2. New tasks are always popping up, distracting you from completing existing tasks and randomizing your focus.

  3. Tasks that are not attached to an email often get forgotten or de-prioritized.

Instead, do a quick look through your email a maximum of twice per day, and use it to populate your to-do list.

If you don’t have a to-do list, remedy that immediately.

Some folks prefer an electronic to-do list they can access from anywhere. Others prefer the brain-boosting benefits of an analog list. Whatever you use, use it consistently: make a habit of returning to it for direction whenever you finish a task, rather than looking at your inbox throughout the day.

Now go thrive!

Can I guarantee that if you do all of these things that your start-up will succeed? Nope. But what I can guarantee is that you will become a more effective entrepreneur and have the ability to create organizations that thrive.

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