The 10 biggest challenges facing entrepreneurs

Many people dream of owning and running their own business, being their own boss, not being beholden to the whims and fancies of other people or an other organisation generally. Many people never actually take the step and make the dream a reality, whilst others, you just cannot hold back.

Much of it, as all the ‘Being an Entrepreneur’ research shows is about an individual's attitude to risk. Many people have all the right creative skills and attributes to make it happen, but are risk averse and so therefore never take the leap of faith required. Conversely, many people do not have either the right creative skills and attributes to run their own business, they just have an idea of one, but because they are risk takers, jump blindly in. Often these are regarded as the ‘Tombstoners’’, with the onlookers always claiming it was never going to work anyway.

For those few individuals who have both the right skills and attributes, plus the ability to control their anxiety caused by risk, it’s still a gamble and one not for the faint hearted. For those who do make the leap of faith, their top ten issues across all the research are the same. These may not be in the same rank order, but they appear on the ‘bucket list’ of entrepreneur issues.

1. Taking the first leap

The biggest struggle for most would be entrepreneurs is taking that first leap. It may be quitting a job, putting up a website, entering a startup accelerator program, approaching someone with your first pitch, or just announcing your venture to the world and family and committing the cash and credit you have. This normally comes after a fair amount of brainstorming and planning. That can be a time when your mind frequently plays tricks on you. Fear, anxiety and doubt creep. You can make plenty of excuses. There are more than enough to choose from. Including timing of your launch.

2. The time it takes for results to show up

Big ‘overnight’ success is really the culmination of steady, consistent small efforts over time. That applies to sales, press and fundraising. Unfortunately, the vast majority of entrepreneurs fold and quit right before the big pay off hits. If only they would have held on for another day, week or month, everything would have come together. Often far bigger than they imagined. In fact, just like Muhammad Ali, the big startup winners are often just those who held out longer, and kept going when everyone else quit and went home. Determine to hang in there. It’s worth it.

3. Cash flow

Cash flow shortages are one of the most common reasons for new business failures. During his interview on the DealMakers Podcast, the founder of the hot TRX suspension training brand, Randy Hetrick, warns that you can go broke in your best month. In fact, that’s often when it happens. You may have just taken a record number of orders. Yet, you also may have a record amount of expenses to deliver on those promises before you get paid and put the money back in the bank. Deal with this by paying attention to your cash flow needs and projections. Then make sure you have insurance and have some financial reserves. Or at least some emergency credit. Always raise more money than you think you’ll need.

4. Fundraising for your startup

There’s a lot more work to startup fundraising than most new entrepreneurs realise. Not having a full understanding of the process and what it takes can lead to a lot of frustration, if not failed rounds, or at least miserable terms. Raising a round can take from 6 to 12 months. Even the best startups and founders can face 'no' 200 times for every cheque they bring in. Then it all starts again.

5. Due diligence

What really becomes challenging in fundraising is the due diligence process after you get funding commitments. The same applies to exits. Learn as much about this process in advance, and get expert advice on how to manage it well. Not only in terms of execution, strategy and investor updates, but mentally and physically surviving the mayhem and stress as well.

6. Time management

We all, always want more time. Why can’t there be 48 hours in a day, and 10 days in a week

Unfortunately, we all share exactly the same number of hours in a day. Some will have far fewer days than others. There will be a lot more to juggle than you imagine if you are hoping to build a true fast growth startup. You’ll be wearing many hats and probably doing tasks you never imagined. Yet, you can’t allow that to rob you of time for a full life either. There are no do-overs when it comes to relationships. Set some boundaries in advance. Remember what is truly most important. Harness all the best time and productivity hacks you can.

7. Delegating

Many great entrepreneurs and business owners still really struggle with this. They may preach it. They may be very intelligent and talented. They just can’t get out of their own way. So, they get stuck owning a small business or being a freelance agent, instead of scaling a true startup and industry disrupting company. The bottom line is that you aren’t going very far unless you learn to hire, outsource, delegate, and more importantly, empower those people to do awesome work. Hire the best. They might not do it 100% like you, but they may actually generate even better results.

8. Balancing perfection & progress

The above is a great way to break the chains of getting bogged down in the never ending pursuit of perfection and detailed minutiae.

Do pay attention to the details and polish. It can make a difference. Yet, you aren’t getting anywhere unless you actually take action.

As Seth Godin puts it, you need to recognise the difference between almost barely good enough, and perfect enough.


9. Keeping ego under control

So far this list has focused on challenges in getting to the top. Well, success can bring more. Chief among them is ego. Your ego can lead you to make many mistakes, bad decisions, and generally let your inner beast go on a rampage at the cost of your relationships, if you aren’t mindfully keeping it in check.


10. Seeing the company fail after an exit

It’s a lot sexier to talk about raising big rounds of VC money and selling companies for billions of dollars. What few talk about is the challenge and pain in seeing a company once loved not be used, underperform or go bankrupt after an exit. If you’re lucky you might be able to buy it back at a discount. A better strategy is to find a great home and custodian for it when you decide to sell. That may be far more valuable to you than the price you get.


Final thoughts

As a footnote to points six and seven above. I have worked with and still see many people who seem to believe that working a 70 to 80 hour week is a badge of honour, almost as a right of passage to being successful. All my experience tells me the opposite. These people end up being the least creative, least productive, least pleasant, least successful, but at least they can say they were present when it goes down around them. 

The above is enough to put anybody off and can be the stuff of nightmares. However, if you have a good idea and can get it to market either on your own, or with the support of others, being an entrepreneur is and can be an extremely rewarding experience. One final thing to consider though is a famous Churchill quote; “To improve is to change; to be perfect is to change often”.

About Ascento

Ascento learning and development specialise in providing workforce development apprenticeship programmes to both apprenticeship levy paying employers and non levy employers. We work closely with employers to identify the key areas for development and design  strategic solutions to tackle these with programmes that are tailored to each individual learner. With two schools of excellence focusing on Management and Digital Marketing we don’t deliver every qualification under the sun, but focus on what we know best and ensure that quality is at the heart of everything we do.


Simon Taylor

Written by Simon Taylor

Ascento L5 Management Tutor.