The ups, the downs, the good and the bad -- Here's what one entrepreneur learned from launching his first startup.

About a year ago, I sat in a coffee shop pitching a new idea to one of the founders of Startup Weekend, Clint Nelson. What we thought would launch in a month turned out to take us nearly a year.

Here are the ups, downs, the good and the bad. Here are 10 things we learned:

1. What you think people should pay for, may be what they think should be free.

When I had the idea for Hello There, I was obsessed with video and the ability to display more effectively who you actually are. I thought people would pay for a custom video page and that analytics would just be a cool added feature.

Wrong. Most people thought the video should be free. (Thanks, YouTube.)

What people perceived as “worth paying for” was the ability to make and unlimited amount of webpages for every job they applied for. In their eyes making a webpage was expensive, hard, and cost a lot of money. They also felt analytics was worth paying for because it helps a user track progress and sentiment. Both huge drivers in pricing psychology.

2. Do not hide your idea! Ever.

I can’t tell you how many people want me to sign f***ing NDAs or are afraid to tell people their ideas. I used to be like that. Thanks to Brad Feld for telling me that was stupid. Most (good) VCs won’t sign them anyway.

The real reason to share your ideas is to find team members and people willing to help and join you. I can’t tell you how many times someone has offered to help because I shared my idea. Without sharing my ideas, I wouldn’t have the bad ass team that I have and I might have had mediocre players.

3. It’s all about the team and motivation.

I don’t outsource product stuff. I actually have never outsourced. I am totally cool with splitting up founders shares and finding the best, most dedicated talent. I think this is more valuable than having total control and working with people who are not invested in the idea.

Building something when you believe in it and being part of something bigger than yourself can be more rewarding than going it alone. Teams, with the right skill set, help drive ideas forward. For me execution is key, and I find top players perform at their peak when it’s crunch time.

4. Why do you need money? Bootstrap it damn it.

I’ve believed in Jason Fried’s philosophy ever since I heard his talk at Big Omaha last year. We lived and breathed it with Hello There. Kept cost at almost nothing, didn’t quit our other jobs, and made deals with third party vendors to get free stuff. Scrappy is the word, I think.

I truly believe that the new economy will be built by people who hold multiple jobs and incomes to survive. Having a job doesn’t mean you can’t work another. For all of you who are saying right now that you don’t have time, I don’t want to hear it. Time is all about prioritizing which is not easy. It takes sacrifice and often it takes sleepless nights. If you are hungry then you will find a way to make food.

5. Build products that make other people look good.

Seriously, I could have never expected the amount of feedback that comes my way, it often sounds like “Thank you for getting me a job.” With this economy it sure makes waking up everyday worth every minute, of every day. Spend time making beautiful, simple products and people will love you for it most of the time. It has made the customer the marketer and evangelist for our brand. Customers are your greatest marketing resource, use them to spread your idea.

6. Your main feature may not be so important.

I love video. I love skype. I get so much more from it than audio or text. Video is how this entire idea started. I am also an extroverted whore and don’t mind being on video. However, I am also not part of the mainstream. I see how the youth interact with videos. Once I realized that making and recording a video was a hurdle, I knew I needed to rethink things. You will probably see the option for photo and PowerPoint in a future release. Human nature and psychology will always drive how we communicate. Sometimes it will revert back to its simplest form.

7. Your product can be in different markets but it needs different branding and pricing.

Hello There was meant for people looking for jobs. That obviously means they probably didn’t want to spend a lot of money. I wanted to make looking for a job affordable. In the process of trying to find bloggers to write about us, I pitched career blogger Heather Huhman, who said she would love to use this for sales. I hadn’t even thought much about that vertical because I wanted to be extremely focused on the career seeker, but it sounded good. Sales people pay for stuff. So I told her that she could use it however she wanted since we don’t brand our pages.

The lesson: perception is reality. If you think you can convince a sales guy to come to your homepage, which is all about careers, and believe in your product you may be nuts. However, you may also be onto something.

8. Freemium, freemium, oh freemium — It can work.

I like freemium or anything that I can try, touch and use before paying. I wanted to offer a product with all the bells and whistles so if the customer thought it was worth it then he could pay for another one and another one… etc. So, we give everyone a free first page. If you get value and like the product then you pay for the next one. It’s actually pretty simple and most customers appreciate a taste before they buy.

9. PR is much easier with a simple product and success stories.

Good luck with your PR efforts if it’s hard to tell someone why they should use your product, unless you pay that awesome $5,000 retainer for an agency. I’d rather find writers and try to build my own relationships with them, then work to give valuable stories to them. Do the work for them and you will be surprised what happens if you have a good product.

10. Don’t give people choices.

I heard a stat one time that almost 90 percent of people need to be told what to do. I believe it. It’s called the paradox of choice and a great book on this is Switch. Our product always had one path which guided the customer throughout the process. Remember, people can only do one thing at a time so only give them one thing to do.

Go buy a notebook and start writing down some ideas. Tell everyone about it and inspire people to join you. Keep everyone motivated with feedback and transparency and find the right markets. And launch a company — profitable or not, it will teach you more than you could ever ask for. Be an entrepreneur. Those are the people who change the world.

Shane Mac is the director of product at zaarly. He’s the founder of Hello There, an author, a professional musician voted best wedding band in 2009 and is obsessed with creating technology that can connect people and change the world for the better.

The Young Entrepreneur Council (Y.E.C.) is an invite-only nonprofit organization comprised of the country’s most promising young entrepreneurs. The Y.E.C promotes entrepreneurship as a solution to youth unemployment and underemployment and provides its members with access to tools, mentorship, and resources that support each stage of a business’s development and growth.


  1. Usman Khan

    Well i agree a successful entrepreneur does not quit his job while works hard to establish his start up part time. There is a lot of risk engaged and i liked the idea of keeping a single product rather then giving user’s a choice

  2. Sign Letter Depot

    Ideas and plans are useless unless you act. I often encounter people that have good ideas and great plans but they never act because they are afraid of making a mistake or not getting everything right. That first step has to be taken even if you don’t think you are ready. Learn by doing and adapt and adjust to grow your business as you grow.

  3. Suresh_Babu

    All of us someday want to own and manage our own companies. Am a aspirant entrepreneur and I kind of feel good for following some of the ways highlighted here. I got a lot more encouragement too and tips. Surely worth a read!

  4. Barry Wheeler

    Your point on NDAs and giving people choices are so true. Ideas need an opportunity to grow, and allowing people to talk about them is one of the ways to aid this growth. As well, the more choices you give people, the more likely they are going to go the wrong way. Limit their options and you will have more success in your sales!

  5. M Solomon6

    My biggest point of contention is in the second paragraph of number 4, which starts to contradict number 3. If your founders are working at their job/multiple jobs, then it will be difficult for them to make the kind of commitment that takes the company to the next level. Furthermore, you will find yourselves setting meetings and deadlines around everyone’s schedules, which is a logistical nightmare. Although it is not popular, the entrepreneur’s ‘leap of faith’ aka quitting your job is still the best way to go IMO

  6. Ty~dogg

    yeaaaaaaaaaaaaa nice

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