9 Biggest Problems When Starting a Business and How to Solve Them

Dakota Shane
Nov 2, 2016 · 18 min read

We’re all living in the age of a lot of things. The age of the internet. The age of social media. The age of Kim Kardashian.

Above all though, we’re living in the Age of Accessibility.

Almost everywhere, content is being given away for free. Oftentimes, the best in the business are just a Tweet away. More books are being written, more videos are being created, and more courses are being generated than ever before — in human history.

Billboards cost anywhere from $8,000 to $25,000+ for a 4 week slot. Now, for $5 per day you can run a targeted ad on Facebook, which could be seen by thousands of prospects much more likely to buy your product than a driver whizzing by.

But looking at things objectively is tough…

If you’re trying to start a business or follow your passion, I know how easy it can be to look at your situation with disdain. With contempt. But remember this: if you’re building a business today then you are creating it in, perhaps, the greatest time to ever build on. Plain and simple.

To drive this point home, I’ve laid out 9 of the most common excuses people have when starting a business (or choosing to not start one), and how to dispose of these excuses. Fortunately, almost all of these ideas aren’t mine. Instead, they are the ideas of people much smarter me.

The information and resources below are taken from some of the top minds throughout various industries. I hope you get as much value out of them as I have.

Let’s dive in…

1.) Not enough money

Money is a tremendous concern when beginning a business. One that most people can relate to. Businesses cost money, and in most cases, a LOT of money. But remember, the time we live in is rich with opportunities people before us were not fortunate enough to have.

Here are some of the many ways to overcome this hurdle…

Taking Advantage of the Gig Economy

You’ll hear a lot of negativity being talked about jobs like Lyft, Uber, Door Dash, Postmates, Instacart, and more. While these jobs are not plush with benefits or without their pitfalls, the mere fact they exist is a blessing to many.

If you are an artist, a starving entrepreneur, or someone saving up for a trip to Europe, then taking a job like Uber could be one of the greatest things you could do. At least on a temporary basis. If you have a meeting with a client, an audition, a concert, a showcase, or something else then you won’t need to ask your boss to call off work.

Of course, it’s not all peaches and cream, but it’s definitely is a step up from flipping burgers for pennies or working a 9–6 that sucks your energy/motivation/time out of you, day in and day out while you try and bring your dreams to life.

Here is a firsthand example of the gig economy at work. Take the time to read this article by Greg Muender. It details how driving for Lyft on the weekends to has allowed him to fund his early-stage startup.

Say what you will about the gig economy. There are a lot of negatives (I was once a biker for DoorDash and, apart from my stint at a dog kennel for pitbulls, was by far my worst job ever), but the fact is the flexibility of these jobs present opportunities that weren’t possible ever before.

Note: If you do want to take advantage of jobs like Uber and Lyft, be sure to do so soon since the automation revolution is not far away.


Americans are shitty negotiators. We seem to always forget most things in life are negotiable. Whether it’s your salary or the price of your future car, there is always room for bargaining. Negotiating could save your business big bucks in expenses.

On this very topic, Medium mogul, Quincy Larson wrote a fantastic piece on salary negotiation (which can be applied to other fields as well):

Christopher Voss’ book Never Split the Difference is one of the best books you could ever read on negotiation. Before entering the business world, Voss was the top FBI hostage negotiator in the United States, so I wouldn’t take his word lightly.

Lastly, here is a very actionable piece of content on negotiation from Rick Harrison of Pawn Stars:

More Things to Read

Here are some of the most helpful resources regarding the issue of not having enough money.

If you want to start a business, are strapped for cash, and aren’t dead-set on the type of business you’d like to start then this article is right up your alley. Additionally, if you’ve caught the entrepreneurial bug and want to start a side-hustle, check it out!

Here’s another good one, especially for those starting a business to make some extra cash.

The 4-Hour Workweek by Tim Ferriss

If you haven’t read the 4-Hour Workweek, then order that shit right now. Actually right now, here’s the link: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357.

Tim Ferriss gives you tangible advice on how to exponentially increase your output, giving you more time to do only the most essential tasks to make your business the most money.

If you don’t have the time to read the book, don’t have the money to buy the book, or are just a cheap-ass, then watch this whiteboard summary of it here.

Chris Guillebeau has created extremely helpful content and a strong community through his work. His book, the $100 Startup details the roadmap for personal freedom by adding value to others, all while having a tightwad budget.

Offering your services as payment

I’m going to bring in one of my top mentors I’ve ever had for this example: my mother. She is a yoga instructor and owns her own yoga business. Last month, she realized how helpful a new iPad would be in marketing her business. Knowing her friend had an iPad, my mom offered her 2 free in-home yoga sessions in exchange for the iPad. Talk about a good negotiation.

Too many people do not think this way and don’t get creative when it comes to costs. If you’re a designer and need marketing, then offer to create design for someone who does marketing! It won’t always work, but it’s so simply you might as well try.

Websites like Simbi allow you to exchange your services for other services, avoiding cash altogether. If you’ve got a useful skill, then this platform might be worth your while!


Credit: edisonawards.com

Kickstarter & Indiegogo & GoFundMe are all some of the top crowdfunding platforms out there. Try them for yourself to see if crowdfunding is right for you.

One huge caveat to crowdfunding is one most don’t realize: the potency of crowdfunding mostly comes in the form of marketing, not in the money. In fact, the potential of virality that goes hand in hand with crowdfunding makes it nearly impossible to calculate and prepare for the results of your programs.

This is why there have been cases where orders not being completed, products not being shipped out, year-long waitlists, and more when it comes to crowdfunding.

Use crowdfunding judiciously. It can be a wonderful tool when done at the scale you’re prepared for.

Venture capital

While venture capital is certainly not easy to obtain, we do all live in a time where venture capital is relatively more accessible than ever before.

According to the National Venture Capital Association (who might know a thing or two about venture capital) there are 798 VC firms in the United States today. In 1995, there were 425.

There are also Angel Investors available today, along with social media platforms like Angel List designed to seek out these investors. The best estimates we have put the total number of angel investors in the United States at 300,000.

I’m not saying it’s easy. In fact, securing funding is a hell of a lot harder now than it was in 2014 or 2015, but it is still attainable.

Paying With Equity Instead of Hard Cash

Lastly, you can always pay with equity as opposed to hard cash. Hiring someone is very expensive, especially when you’re first starting out and strapped for cash. If you can get someone else as excited about your vision as you are, then bring them along for the journey. You don’t have to go on it alone.

2.) Not Enough Connections

I won’t spend much time on this bullet point because there’s this beautiful thing called social media. Be sure to use it! Thousands, even millions, of people are at your finger tips, waiting to connect with people just like you.

Social Media

When it comes to building a useful network to leverage for your business, not all social media platforms are created equally. Here are some of the best for networking:

  1. Meetup.com is my personal favorite for networking. I’ve never been a “cocktail party” kind of guy, and for people like me — who are most comfortable in casual scenarios — Meetup is a godsend!

2. LinkedIn Groups

3. Facebook Groups

4. Twitter Lists

Leveraging Your Existing Network

You know more people than you think you do. I guarantee it. I was fortunate enough to have worked with Don McQuade, former Vice Chancellor of UC Berkeley at my last startup position. Don taught me countless things, day in and day out. But one piece of advice stuck with me more than others:

The best advice I could ever give you is this: Always manage and maintain your relationships. — Don McQuade, UC Berkeley Professor of English

Don is a master networker whose circle includes everyone from Jeff Goodby to Noam Chomsky. Don told me to make a list of people I want to stay in contact with, or reconnect with. Then, every 6 months or so, I should shoot them an email to catch up. The trick here is to reach out to them just because, and not only when you need something from them. This builds trust, a substantive relationship, and hopefully a fruitful friendship.

Don McQuade

3.) Not enough time

“If you’re watching this on your laptop at home right now, and you’re not pumped — the one thing I know everybody can do is watch a little less House of Cards, it’s go to the bar a little less times with their buddies, don’t play f*#&$#*^# Candy Crush… That is why I’m obsessed with hustle. It’s the one variable that everyone can control.” — Gary Vaynerchuk to Entrepreneur Magazine

If you say you don’t have enough time, be sure you’re being honest with yourself on how and where you’re spending your time. The truth is, it doesn’t matter how fast or slow you go, as long as you make progress and don’t stop. Everyone can carve out half an hour a day, or 2 hours on a Sunday to get the ball rolling on what they love.

In short, you’re going to have to make sacrifices. We all know this is true. Be sure to choose wisely and stay firm.

There has been a fair amount of backlash towards the “getting up early” camp. I understand why this is. If I don’t wake up at 5am every single day, the last thing I want is some know-it-all stranger telling me how I should live my life and wake up earlier.

But here’s the thing: There‘s a reason why the morning is the best time to build something. In fact, there is a very good reason why it’s the best time to build something — the reason is because it’s completely yours.

In the mornings, you don’t have to answer to anyone but yourself.

Think about it. The rest of the day is unpredictable and in flux. You could get pulled into a meeting or have to catch your nephew’s cello recital. You could have a networking event after work or have to polish up that presentation you procrastinated for. Or — just imagine this — you might want to do something FUN in the evening!

When compared to the mornings, evenings simply have too many variables when it comes to having them free day in and day out.

4.) Not Enough Experience

With all the information available online nowadays, it’s getting harder and harder for anyone to use the excuse of not having enough experience. Despite this, it’s one you’ll hear a hell of a lot, so here are some resources to consider using when learning a new skill or sharpening an existing one.

Learn Things Yourself

With the internet generally, and MOOC/EdTech platforms specifically, knowledge is more accessible than ever before. Here are just a few websites where you can learn something for free or cheap:



Khan Academy




Podcasts — Stitcher, SoundCloud, PodCast store.

Of course, you can’t forget Medium — which I guess I don’t have to link up here. If you don’t enjoy reading as much as listening, check out Play. It’s a new product that converts Medium articles into audio files for you to stream and listen to anywhere.

If you are building a tech product, I know learning computer programming can be a huge hurdle to leap over. While I do recommend finding someone else to program for you versus learning CS from scratch, if you’d like to learn how to, there are an immense amount of services out there:

Codeacademy & Code.org & Free Code Camp are just a few of the resources out available to teach you coding from the ground up. Once you have the basics, graduate to more advanced online courses or drop into a course at a local community college near you.

Find Someone Who Can Do It For You

Finding someone to do it for you will save you insane amounts of time, and thus money. Not everyone can be specialists in everything, and finding someone to add to your team with the skills you need most is crucial.

Services like Cofounders Lab are outstanding tools for finding cofounders and early hires for your company. Cofounders Lab is the Match.com for cofounders.

You can sort by skills you need, location, and more. Then potential matches are displayed for you.

On the same topic, finding a design-savvy person for your team is one of the most important things you can do. Yet design is one of the most crucial elements to building a brand.

Image Credit: negliadesign.com

In January of 2008, Stanford University conducted an experiment where 11 CalTech graduate students who “occasionally drank fine wine” were given wine with 2 difference price tags: $5 and $45. When asked which wine they enjoyed most, the participants chose the $45 more than the $5 wine — by an obscene margin.

The only catch?

The wine was exactly the same. Literally, the same wine.

This is a prime example of what is called perceived value. In reality, perception is reality. People will pay for things that look and feel expensive, which is precisely why design is so important. If you have outstanding design, you have a huge leg up on the competition. Plain and simple.

The problem is, not everyone knows a great designer. Fortunately, there are options out there. Here are some alternatives you can use if you do not have a designer on your team yet.

Fiverr.com. This site has cheap options for “gig-based” work, including logo designs, website copy, and more. The only caveat is you get what you pay for. You — most likely — will not find incredible design here nor your dream design partner.

Unsplash. While not exactly “design”, stunning photography is one of the fastest ways to make your business seem more expensive than it really is. This website gives away free, top-notch stock photography. Unsplash is where a shit ton of Medium writers get their header photos from.

Image from Unsplash.com
Image from Unsplash.com

Pexels.com. Is another website just like Unsplash.

Carbonmade. This website is chalk-full of hungry, talented freelancers — mostly designers, but also copywriters — looking to beef up their portfolios and client list. If you do your research, your chances are very high of finding a diamond in the rough on Carbonmade.


99Designs. According to the website, prices start at $299, so this option is a little on the higher end but still way cheaper than what you would pay a design agency or high-end freelance designer.

I’d like to close this section out with a book I would recommend to anyone and everyone, and that is The Personal MBA by Josh Kaufman.

The Personal MBA is one of my all-time favorite books. While I have never received an MBA to compare the two, I trust guys like Seth Godin, Kevin Kelly, as well as accomplishments like the #1 International Bestseller to validate my opinion.

Kaufman goes into detail about all topics on the X’s & O’s of business. If you don’t have the time or money to go to business school but would still like to set yourself up for business success, this book is a must-read.

The best part is, you don’t need to read it cover to cover! Just read the chapters you think will be most helpful.

5.) Not a good enough idea

This can be a tough one. Ideas are like children, no matter if they piss on the neighbors porch they’re still perfect in the eyes of their parents. Being able to look at your idea(s) objectively is an invaluable skill.

For starters, read this article:

  1. Run your idea by your acquaintances or friends who keep it “real” with you.
  2. Test it using tools like Beta Easy to beta test.
  3. Offer your services/product for free at first! This will cut out the price barrier and gauge demand for your product or service.

Litmus test: Ask yourself the question, “Would you pay for the service you’re offering?”

6.) Not the right personality

From the outside in, personality seems to take a back-seat when it comes to the business world. There is a trend for valuing talent and skill over leadership abilities.

No matter how great you can code, you still have to have the ability to get others excited about what you’re creating. Especially in the competitive market existing today where you have to pitch to stakeholders about everything from which toilet seat your team is going to use and whether your team will order Clif Bars Quest Bars.

The only alternative here is finding a cofounder to do all the talking for you. Nonetheless, you’re going to have to speak at some point. So why not equip yourself with the tools in advance?

Here are the two best books I’ve come across on the psychology behind magnetism, leadership skills, and the ability to trigger human emotion.

Mike Dillard’s Magnetic Sponsoring.

Mike Dillard goes into detail around why humans feel attracted to specific people. He dives into the psychology of charisma, and how everyone can learn the tactics it takes to be magnetic.

If you are looking to sharpen your leadership skills, increase your sales skills, or just want to learn how to be more charismatic, then this book is an absolutely essential read.

Robert Cialdini’s Influence.

I finally got around to reading this recently. It’s fantastic and a must-read for anyone and everyone.

If you’ve heard of terms that frequent the business world, especially marketing, like the “Principle of Reciprocity” and “social proofing”, then you have been exposed to Robert Cialdini’s ideas laid out in Influence.

No matter if you’re a sales person, an engineer, or trying to sell more candy bars for your school fundraiser, this book is invaluable. Period.

7.) Don’t Know Where to Start

Feeling overwhelmed and don’t know where to start? Perhaps, you have so many ideas you want to bring to life you don’t know which one to start with.

The short answer is you’re going to have to start somewhere, and it’ll have to be with only one idea.

If you aren’t sure where to start, or which idea to start on then I know the perfect piece of reading for you: The School of Greatness, chapter 1.

I am a huge fan of Lewis Howes (I gotta show some love for a fellow Ohio boy!). If you’re in the position of trying to “start out” with your venture, then the first chapter in The School of Greatness will be one of the most actionable, helpful, and thought-provoking pieces you’ll ever read. I promise.

8.) Losing your inspiration

You might be burnt out from all the work you’re doing. If so, then be sure to read this article. It will help to get your head on straight again and avoid the craziness increasing.

Digital detox — This is another idea from Lewis Howes and The School of Greatness. A digital detox is any period of time you take completely unplugged and shut out from electronics, social media, Netflix, etc. It’s a day to take a step back, relax, and critically evaluate if you’re going in the direction you want to go in.

Digital detoxes can be any length of time. I try my very best to take at least a couple hours each Sunday to completely unplug, walk around Lake Merritt, and just think.

It’s amazing how refreshing it is to ask the most basic questions to yourself. We’re constantly evolving, and need to always be asking our new selves if what we’re doing is still aligned with who we are.

Identifying the difference between whining/excuses and rough times

No matter if it’s your first job or your dream job, we’re all going to have days where we just want to say “fuck this” and quit. Being able to take a step back and distinguish between a bad day or a bad job is a skill everyone needs to hone.

Additionally, never underestimate the effectiveness of passion. If you aren’t passionate about the thing you’re building, chances are you will not have the resilience to weather through the rough times you’ll inevitably go through. Build something you’re passionate about.

9.) Fear

Fear is one of the biggest inhibitors to throwing yourself off the edge and building your dream business/project. For this section, you only need to watch one piece of content to convince you to overcome your fear, and that is Steve Jobs’ commencement speech at Stanford.

If you haven’t seen this video, I’m so jealous of you right now because you’ll be able to see it for the first time. If you don’t get anything else out of this article, then please at least watch this video. It’s life-changing.

Entrepreneurship is throwing yourself off a cliff and assembling a plane on the way down. — Reid Hoffman

Final Point

Here’s the thing — there’s a reason why cliches exist: because they’re almost always true. They’ve been proven time and time again. Year after year.

Take advantage of all of the content in the world by learning from other people’s experiences. Scale your experiences by living vicariously through other’s journeys. Through other’s teachings and what they have learned.

Take advantage of all of the cliches the world has to offer. You might just find the right context to finally drive the point home for you. I know I have.

Thanks for reading! If you enjoyed this article, share it with a friend or just Michael Tyson that green heart. Either would be much appreciated :)


A network of business & tech podcasts designed to…


A network of business & tech podcasts designed to accelerate learning.

Dakota Shane

Written by

I help make content marketing simple. Columnist: Inc.com. Co-Founder: Copy Buffs (a copywriting agency). Follow me on Twitter. www.copybuffs.com


A network of business & tech podcasts designed to accelerate learning.