The 10 Biggest Challenges Every Entrepreneur Faces

The 10 Biggest Different Challenges Every
Entrepreneur Faces (And How To Conquer

Them)
To be an entrepreneur means to be someone who takes on challenges. It is absolutely
synonymous. It also means you are a problem solver. Knowing what is ahead is half the battle.
The list below is compiled from the challenges that I have recognized from reading articles in
relation to this assignment and also from the most successful entrepreneurs on the DealMakers
Podcast.
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 dollars
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 and doubt creep. You can make plenty of excuses.
There are more than enough to choose from. Including timing of your launch.
From all the super successful entrepreneurs I read on , I understood two things stand out here.
The first is that many of the most successful billion dollar startups were launched and acquired in
what most would consider the worst crises and economic times. The timing is always better than
you think. Figuring it out as you go is one of the most fun and rewarding parts of being an
entrepreneur. Just do it.
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 is cash flow
management.
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. A hurricane could come through and stall your income for a month. A government
shutdown could kick in and freeze all the payments from a big government contract.
Beat 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 realize. 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.
From my point of view raising a round can take from 6 to 12 months. Even the best startups and
founders can face 200 no’s for every check they bring in. Then it all starts again.
When it comes to fundraising it is all about mastering storytelling and capturing the essence in 15
to 20 slides. For a winning deck, take a look at the pitch deck template created by Silicon Valley
legend,
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 mayhe;e 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.
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 recognize 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 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
franc. 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.

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The 10 Biggest Challenges Every Entrepreneur Faces

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The 10 Biggest Different Challenges Every

Entrepreneur Faces (And How To Conquer

1) Taking the First Leap

2) The Time it Takes for Results to Show Up

4) Fundraising for Your Startup

8) Balancing Perfection & Progress

9) Keeping Ego Under Control

10) Seeing The Company Fail After an Exit

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