After doing tons of cover stories on entrepreneurs during my stint as a journalist at Silicon India — a magazine that dives into the stories of top executives and business innovators  — and soaking up insights from our CEO, Arjun Mahadevan (who’s probably talked to more founders than you can count on his podcast:15-minute founder), I’ve compiled this tiny list of mistakes that entrepreneurs in Silicon Valley often make. 

And trust me, they’re not the usual ones like getting sidetracked, not filing taxes on time, failing to plan ahead, or ignoring new trends.

Every entrepreneur knows those like the back of their hand before they even jump into this wild ride.

These are the sneakier ones that blindside you while you’re busy brainstorming for your next big product release.

They make you realize, sometimes too late, that you’ve made a big goof-up, either from not knowing or just choosing to ignore the warning signs.

Let me share an example. One founder told me he spent months perfecting his product, only to realize he didn’t have a solid customer support feedback system in place.

Another was so focused on rapid growth that he neglected company culture, leading to a mass exodus of talented team members.

It’s these less spoken moments or mistakes that can really throw you off your game.

And believe me, everyone goes through them but they are too late to take action.

So, in this post, we’re diving into those hidden pitfalls that even the best entrepreneurs don’t see coming. 

Let’s get started.

Here Are the 6 Most Common Mistakes That Will Guarantee You Get Stuck

Mistake #1 Not Delegating Enough

Ah, the classic entrepreneurial trap: thinking you can do it all. It’s like trying to build a big wall all by yourself.

Sure, you can lay a few bricks, but it’s going to take you forever and might not even stand tall for a day.

I get it. You trust yourself to do everything exactly how you want it done. And why not?

Handling all the tasks yourself seems like a cost-effective strategy.

For example, in the first few years, you might write every check and spend every Saturday at the bank, even though accounting isn’t your jam. 

You even try to monitor the design of your website, supervise customer service, and do marketing all at once — you end up spreading yourself too thin.

Now, you are not a superhero with superpowers. It’s utterly insane to dip your toes everywhere just because you hate delegating.

It’s simple. For your company to grow, you need to focus on what you’re UNIQUELY QUALIFIED TO DO. Think of yourself as the secret sauce. You’ve got the vision and the skills that make your company special. 

So spend time doing that.

Start small, but try delegating about 15% of your tasks each year. When you do this consistently, you’ll be able to concentrate your time and talents on making company-wide decisions more impactful.

So, instead of juggling every single task, start delegating. You might not nail it perfectly at first — you’ll probably still do some stuff you shouldn’t — but you’re improving at the end of the day. And that’s a good sign.

Delegation isn’t a sign of weakness; it’s how great companies get even better. Plus, it shows immense trust in your team when you let go of those tasks you used to micromanage with an iron grip.

In fact, Richard Branson, the entrepreneurial rock star himself, swears by delegation.

He empowers his team to take the reins, freeing him up to focus on strategic vision and innovation. If it works for him, it can definitely work for you, too.

So, the next time you’re tempted to do it all, remember — even superheroes have sidekicks.

Delegating isn’t shirking your duties; it’s how you supercharge your company’s growth and show faith in your team’s capabilities. Trust me, it is one of the best favors you can do for yourself and your business

Mistake #2 Not Setting Appropriate Customer Expectations

This mistake can be a real pain, especially as your business grows.

As you expand, one of your biggest challenges will be making sure customers understand that while you have a hand in everything your company creates and launches, you’re not personally crafting every single slide of every strategic plan. 

It’s tough, especially when you’re the face of the company and clients expect you to personally manage every project. 

But they have to understand you’re not Superman (or Superwoman) with endless hours in a day. Yes, no doubt you are amazing, but you’ve got a team for a reason!

A lot of entrepreneurs struggle with this.

So, what’s the trick? 

Start talking more about “we” and less about “me” when you’re discussing your company and what it can do. When you make this shift, clients start to understand that the whole team is working on their projects, not just you. And once that clicks, several great things happen. For example:

✅ They’ll start trusting your team: Clients begin to trust your team’s capabilities. This trust is crucial because it shows that your business isn’t a one-person show. Your team feels empowered and appreciated, which boosts morale and productivity.

✅ Boost in scalability: When clients recognize that the workload is shared, they’re more comfortable with larger projects. They know there are multiple experts handling different aspects, which means better quality and efficiency.

✅ Realistic expectations: It sets realistic expectations about what can be delivered and when. Clients know that their projects are in good hands, even if you’re not personally involved in every detail.

In addition, be upfront with clients, especially when it comes to timelines.

Imagine telling a client their project can start immediately, only to inform them later there’s a 3-4 week wait.  Frustration level = pro max!!

They need your honesty and we all know how honesty builds trust. This trust can lead to better long-term relationships and repeat business. 

Need a little more wisdom?

One of the big sharks, Amazon’s Jeff Bezos, once said, “We are stubborn on vision. We are flexible on details.”

That’s the approach you need to take with setting customer expectations. Be clear about what you can deliver and when, but be flexible with the details.

So don’t be eager to say, “Sure, I can get that to you by tomorrow.” Take a deep breath and think teamwork.

You’re gonna love this: The Lifestyle of a Successful Entrepreneur: 17 Winning Habits

Mistake #3 Not Gathering Enough Customer Feedback

According to Microsoft, 77% of customers view brands more favorably if they proactively invite and accept customer feedback. Need I say anything more? Well, I will anyway.

We’re in 2024, floating in data from every platform and media imaginable. If you’re not using this gold to figure out what your customers really think, then you’re stuck in the Stone Age.

Don’t get me wrong here, but you should be leveraging every single piece of feedback you get — from social media, community hubs, and even simple Google reviews. 

Look at what your customers are saying. Are they thrilled with your service or dragging your brand through the mud while you’re busy with your launch campaigns?

Meanwhile, your competitors are monitoring all those negative comments and swooping in with their products. You certainly don’t want that.

Here’s what actually happens. You might agree to disagree, but this is the reality.

Early on, when you’re personally handling every project and chatting with every customer, it feels like you have a solid grasp of what your clients think.

It’s like you’re in the thick of it, managing everything, and feedback seems informal but constant. 

But as your business grows and your team starts handling more customer interactions, that informal system falls apart. Suddenly, you’re not the only one talking to clients, and it’s critical to have a consistent, standardized feedback system in place.

Without it, you’re flying blind.

Many businesses, big and small, have learned this the hard way.

Take Airbnb, for example. In its early days, feedback was informal and inconsistent.

As the platform grew, they implemented a more structured review system, which has been crucial in maintaining trust and improving services.

Another great example is Apple. They are known for their rigorous customer feedback mechanisms, which have helped them consistently improve their products and services.

Apple’s NPS (Net Promoter Score) is reportedly around 72, showing how even the biggest brands prioritize customer feedback. And according to Bain & Company, companies with high NPS scores grow at more than twice the rate of their competitors.

The Importance of Customer Feedback

Customer feedback is essential for several reasons:

Identifying Pain Points: Feedback helps you pinpoint exactly what’s working and what’s not. Without it, you’re guessing, and guessing can lead to costly mistakes.

Driving Innovation: Your customers are a goldmine of ideas. They use your products and services daily and can offer insights you might not have considered. Leveraging this feedback can lead to significant innovations and improvements.

Building Customer Loyalty: When customers see that you value their opinions and make changes based on their feedback, they feel heard and appreciated. This builds loyalty and turns customers into advocates for your brand.

Benchmarking Performance: Regular feedback allows you to track your performance over time. Are your efforts to improve customer service paying off? Are new products meeting customer expectations? Feedback provides the data you need to answer these questions.

How to Harness Customer Feedback

Choose the Right Tools: There are many tools out there, like SurveyMonkey, Typeform, and specialized NPS tools.

For social media feedback, platforms like HubSpot offer comprehensive social media monitoring tools.

HubSpot not only helps in gathering feedback but also allows you to manage and analyze it effectively. It integrates with various social media platforms to provide real-time insights into customer sentiments.

Make It Regular: Don’t just ask for feedback once in a blue moon. Make it a regular part of your process.

Whether it’s after every project, quarterly, or semi-annually, consistency is key.

Act on the Feedback: Gathering feedback is just the first step. The real magic happens when you act on it.

Show your customers that you value their input by making tangible improvements.

Mistake #4 Giving Up First Mover Advantage

This one reminds me of an acquaintance who started a podcast on accounting in Mumbai.

He had a show called “Accounting Today,” one of the first daily podcasts in the bookkeeping space. It was going strong because, well, he was one of the first to do it. 

But after 18 months, he quit. He got tired and felt like he had nothing more to say.

But this break allowed others to step in and fill the space he left, and by the time he returned with version 2.0, he had lost that crucial first mover advantage. Yeah, that hurts.

Now, giving up the first mover advantage means losing the lead you had by being the first to enter a market or launch a new product or service, just like my acquaintance with his podcast.

In simple terms, if you wander off and don’t keep the buzz alive, others will swoop in and grab all the good stuff.

Think of it like being the first person at a buffet. You get the best picks — prime rib, fancy cheeses, the works.

But if you wander off for a long bathroom or smoke break, don’t be surprised when you come back to find only a sad-looking salad.

Even BIG brands have succumbed to this mistake.

For example, Kodak was a pioneer in photography but failed to capitalize on the digital camera revolution.

The brand had the technology but didn’t push it forward. Other companies like Canon and Nikon jumped in and took over the market. Kodak’s first mover advantage disappeared because they didn’t adapt quickly enough.

Here are some tips to keep up your first mover advantage, gathered from doola’s interactions with entrepreneurs around the world:

Stay the Course: If you’re the first in your market, don’t rest on your laurels. Keep innovating and improving. The initial lead is valuable, but maintaining it requires ongoing effort.

Adapt and Innovate: Markets change, and new competitors will emerge. Continuously adapt your strategies and offerings to stay ahead.

Leverage Your Lead: Use the time you have as the market leader to build strong customer relationships, refine your product, and set higher standards. Make it hard for newcomers to catch up.

Keep in mind: people only remember who got there first. 

So, never let fatigue or complacency open the door for competitors to steal your spot. Never give up on your first mover advantage at any cost. 

Mistake #5 Picking the Wrong Competitors

Imagine you own a cozy little coffee shop in your neighborhood. You make fantastic lattes, and your customers love the personal touch you bring.

Now, let’s say a fancy bakery opens up down the street, and you decide to compete with them by offering a wide array of baked goods. 

You see their massive menu and start to think, “I need to do all of that!”

So, you start focusing all your energy on creating the perfect croissant instead of your amazing coffee.

And that’s where you lose. 

Your customers came to you for that great coffee and personal touch, not for pastries.

By trying to out-bake the bakery, you lose what made your coffee shop special, and your regulars might start drifting away.

And you wouldn’t want that, would you?

To be honest, Picking the wrong competitors is like bringing a knife to a gunfight.

You might think you’re ready for a battle, but you’re completely outmatched and in the wrong arena. Don’t get me wrong:)

Focusing on the wrong competitors can lead to:

Wasted Resources: You spend time, money, and effort trying to match or outdo competitors who aren’t your real rivals.

Lost Identity: In trying to mimic competitors, you might lose what makes your brand unique and special. Nobody needs another cookie-cutter copycat.

Missed Opportunities: By not focusing on the right competitors, you miss the chance to innovate in the areas that really matter to your customers.

Instead, you’re stuck in a game of catch-up.

So, don’t waste your energy trying to be something you’re not by chasing the wrong competitors. 

Here’s what you should do instead:

Know Your Strengths: Understand what makes your business unique and focus on enhancing those aspects rather than trying to copy competitors. 

Identify Real Competitors: Look at who is genuinely impacting your market share and customer base. Sometimes, the biggest threats come from unexpected places. So, keep your eyes wide open.

Adapt and Innovate: Keep an eye on market trends and be open to tweak your market strategies.

Innovation often comes from understanding what your customers need, not just what your competitors are doing.

Mistake #6 Not Keeping Bookkeeping Records

Nasty Gal, an online fashion retailer founded by Sophia Amoruso, grew rapidly from a small eBay store to a booming online brand.

However, their rapid growth wasn’t backed by solid financial practices. 

The lack of proper bookkeeping and financial oversight led to cash flow issues, unmanageable debt, and operational inefficiencies.

Despite their popularity and massive sales, the financial mismanagement caught up with them, leading to bankruptcy in 2016. 

Nasty Gal’s downfall is a stark reminder that no matter how successful your brand seems, bad bookkeeping can lead to serious trouble. 

Here’s Why Bookkeeping Matters:

Financial Blind Spots: Without accurate records, you won’t have a clear view of your finances. This can lead to overspending and cash flow problems.

Tax Troubles: Come tax time, missing receipts and undocumented expenses can lead to inaccurate filings, which can result in fines or missed deductions.

Poor Decision Making: Good financial data is crucial for making informed business decisions. Without it, your financial goals are in the dark.

Here’s what doola advises most entrepreneurs during consultations. See if you can pick up one or two tips from here:

Use Accounting Software: Invest in good accounting software like QuickBooks, Gusto, Xero, or FreshBooks. These tools make it easy to track every expense, no matter how small, and keep your records organized.

Set a Routine: Make it a habit to log expenses regularly. Whether it’s daily or weekly, consistency is key.

Take a few minutes each day to update your records, and you’ll avoid the last-minute scramble.

Keep Receipts: Yes, it’s a pain, but keeping receipts for all business expenses is essential.

Use a mobile app to scan and store receipts digitally. Apps like Expensify, or even just Google Drive can make this process painless.

Hire a Bookkeeper: If managing finances isn’t your strong suit, consider hiring a bookkeeper. Even a part-time bookkeeper can help keep your records straight and provide peace of mind.

Review Regularly: Schedule regular reviews of your financial records. This helps you catch any discrepancies early and stay on top of your financial health.

Navigating the Entrepreneurial Rollercoaster

Did you know a startup has just a 0.00006% chance of becoming a unicorn? That’s like 3 out of every five million companies!

Struggle is part of the game you signed up for on your entrepreneurial journey. The road is full of risks, and the biggest risk is falling into common traps or mistakes.

But if you want to be the best entrepreneur you can be and grow your business, you must ensure these mistakes don’t trip you up.

You don’t want to be the bottleneck in your own journey.

To stay ahead of these pitfalls you need build upon these four things:

Acknowledge these mistakes and take action immediately. Don’t wait for your first dip in ROI to realize something’s off.

Track patterns that lead to these mistakes. Identify them early, so they don’t grow and consume your hard work and resources.

Nip them in the bud. Catch issues early and deal with them before they escalate.

Enjoy the journey. Don’t forget to take a moment to appreciate the ride, with all its ups and downs.

Remember, the goal isn’t just to avoid mistakes but to learn from them and keep moving forward. 

How doola Can Simplify Your Entrepreneurial Journey

Managing the nuts and bolts of a business can be quite taxing. This is where doola comes in. 

We are here to simplify your entrepreneurial journey with our “business in a box” toolkit, designed especially for new business owners. 

From the initial registration of your business venture to the preparation of accounting books for your business, we have covered you.

Here’s what we have in our arsenal to help you:

Business Formation Services: When it comes to the establishment of a business entity, doola assists in the creation process while guaranteeing that all legal formalities are taken care of.

Bookkeeping Services: Simplify financial management with our bookkeeping services, freeing up your time to concentrate on development instead of calculations.

Compliance Services: Stay compliant with all necessary regulations, reducing the risk of costly mistakes.

Tax Consultation: doola’s tax professionals take care of several tax and IRS aspects for you so you get to save money and time during tax filing season.

Would you like to know more of how you could benefit from our support? 

Book a free consultation with us today and see how we can help you succeed!

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