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7 Pain Points Entrepreneurs Should Expect—and Embrace

Peter Daisyme
Peter Daisyme
business.com Member
Dec 21, 2015

The famous saying of “no pain, no gain” rings especially true for entrepreneurs. 

When starting out, there's bound to be some bumps and bruises as you stumble through new situations and experiences.

Even as your company develops and begins to take flight, there will be growing pains. 

To prepare you for what's to come as an entrepreneur, here are seven pain points that I, and many entrepreneurs like me, have experienced over the years:

1. Finding the First Users

The first users of your product or service are the key because they can tell others about what you offer. However, convincing someone to be the first user can be painful because the most work goes into influencing the decision. That’s why many companies desperately try anything to get those first users, including giving away the product or service for free or by offering a trial use period. It can seem like an impossible task but it’s one worth the considerable effort it will take to locate and win over those first users.

That’s why many companies desperately try anything to get those first users, including giving away the product or service for free or by offering a trial use period. It can seem like an impossible task but it’s one worth the considerable effort it will take to locate and win over those first users.

As Lisa Stone, Co-Founder and CEO of BlogHer, said, “Wonder what your customer really wants? Ask. Don’t tell.” Those first users will come faster if you go out there and take the time to get to know your prospects and find out what they are really seeking. Then go back and make sure what you are offering fills that void for them. Return to those prospects and show them what you have done to see if it’s something they want. If they say yes, then you have the first users and that pain has been alleviated. Don’t give up either because imagine if others had done so. For example,

Those first users will come faster if you go out there and take the time to get to know your prospects and find out what they are really seeking. Then go back and make sure what you are offering fills that void for them. Return to those prospects and show them what you have done to see if it’s something they want. If they say yes, then you have the first users and that pain has been alleviated. Don’t give up either because imagine if others had done so. For example,

For example, Harland David Sanders (AKA Colonel Sanders of Kentucky Fried Chicken) had his chicken recipe rejected by over 1,000 restaurants before it was finally accepted. If he gave up, there’d be “no finger licking good” chicken.

2. Being Rejected From Investors

It hurts the confidence, pride, and wallet when investors don’t want to fund your startup. Hearing “no” over and over again continues to sting. If no one else believes in the idea, then it can’t be that good. That’s not necessarily true and the pain is a sign to find out why there is a lack of interest on the part of investors. It could be that you just have been targeting the wrong type of investors for your business or you need to provide more evidence of current and future success.

That’s not necessarily true and the pain is a sign to find out why there is a lack of interest on the part of investors. It could be that you just have been targeting the wrong type of investors for your business or you need to provide more evidence of current and future success.

Ask those investors for a reason why they turned you down so you can regroup and try again. The founder of Nutmeg was rejected by 45 different investors, which had to hurt. However, if he gave up and skipped out on meeting #46, the company would not be the success it is today. Each meeting taught him something about what investors were looking for and which ones he needed to target.

3. Getting and Keeping Talent

When starting out, there are not a lot of resources available to create that winning team. In sports, the winning teams are often those that have the most money to “buy” the talent they need.

However, in creating a startup, there are no funds to get the best and brightest. It may seem that without access to a skilled team, you will not be able to develop your product or service or you may not be able to market and launch it. However, not every talented individual out there is looking for the highest bidder. Many want to get in on the ground floor and grow with a company because their goals are to be a part of something that becomes big.

You can leverage this desire while also taking advantage of the incredible number of freelancers who are willing to work from anywhere in the world for startup rates. While you may not be able to keep all the talent you come across, there are those that will stay if they see career and income growth potential. It takes effort and not every individual you select is right for the company, but online marketplaces and networking sites put you in front of many fish that are in the workforce sea.

It takes effort and not every individual you select is right for the company, but online marketplaces and networking sites put you in front of many fish that are in the workforce sea.

4. Realizing It’s the Wrong Direction

Nothing cuts deeper than the realization that you have been heading in the wrong direction with your business, especially after dedicating a certain amount of time and money to it. You can kick yourself for thinking you’ve wasted resources, but what you really need to do is be glad you realized sooner than later that you needed to pivot and alter your course to better meet your market and target customers’ needs.

As Benny Luo, Founder of NextShark, DiscoverMe, and The Other Asians, explained, “One day I realized that after each failure, I always gained some valuable knowledge of things I could apply to or avoid in my next project. That was the attitude I adopted after every failure from then on, I focused on what I gained instead of what I lost, because that’s what really matters in the end.” The same goes for Ruslan Fazlyev, Founder and CEO of Ecwid, who originally started another company, X-Cart only to discover that small business owners already had websites. Instead, they needed a solution that would let them sell online, so he changed course and

The same goes for Ruslan Fazlyev, Founder and CEO of Ecwid, who originally started another company, X-Cart only to discover that small business owners already had websites. Instead, they needed a solution that would let them sell online, so he changed course and Ecwid was born. Take what you learned, put toward the new direction, and keep going.

5. Lacking Support

It hurts when you feel like you are all alone on your mission. Stephen King was rejected over 30 times with his first book, Carrie, to the point where he gave up and threw it away. However, it was his wife that removed it from the trash, encouraged him to try again, and from then on he was a success. Everyone needs that cheerleader on their side that believes and provides the emotional support necessary to work through the rejection, self-doubt, and frustration. Look to offline and online networking groups for a mentor or coach that can lend their support and advice to help you avoid the pain of working alone. Plus, you may even learn more from those that are supporting you.

As Reid Hoffman, Co-Founder of LinkedIn, noted, “The fastest way to change yourself is to hang out with people who are already the way you want to be.”

6. Doing It All – and Trying to Do It Well

Like the lack of support, doing it all yourself all the time and being good at it can leave you physically, mentally, and emotionally in considerable pain. Overwork those muscles and you not only will experience pain, but you could also be doing more damage than good. 

While it does conserve resources and feels satisfying to a certain degree, it is important to strike a balance, ask for help, and recognize when a particular area is not your strong suit. This does not mean you are a weak person; instead, it says you are smart and savvy in your understanding of where your skills and knowledge can be best utilized. Not even super heroes can do everything well. That’s why they often work in pairs or as a team. 

7. Failing and Shutting Down the Business

No one wants have to live that moment where it’s time to acknowledge that the business is just not going to work. You feel as though you have let yourself down as well as investors, staff, and family and friends. I have been through that painful experience of watching a business implode after seeming to be going so well. It's a sinking feeling when you see it fall apart. As the leader, I felt responsible but had to deal with it and keep going.

It happens and you can’t let that failure consume you and prohibit moving forward to try something new. Some of the most successful and admired people have failed numerous times and they will say they are glad they did. Thomas Edison remarked, “I have not failed. I’ve just found 10,000 ways that won’t work.” Henry Ford agreed when he said, “Failure is simply the opportunity to begin again, this time more intelligently.” Finally, Napoleon Hill stated, “Most great people have attained their greatest success just one step beyond their greatest failure.” Accept the fact that this particular venture did not make it, learn from it, and focus on making the next startup a success.

The way I see it (especially now that I’m successful), if being an entrepreneur was that easy to begin with, it would not have felt as satisfying as it did when success finally came. Pain doesn't last forever, especially if you are prepared with these "first aid" tips I've mentioned here. I have failed in business but grown in character, experience, and wisdom -- all of which have been beneficial for growing my business and exploring the potential of other startups. With each startup, the pain points have lessened or new ones have appeared, but when they do, I embrace and work through them.

Image Credit: Rawpixel / Getty Images
Peter Daisyme
Peter Daisyme
business.com Member
Peter Daisyme is the co-founder of Palo Alto, California-based Hostt, specializing in helping businesses with hosting their website for free, for life. Previously he was the co-founder of Pixloo, a company that helped people sell their homes online, that was acquired in 2012.