It’s been a hectic week. I put the finishing touches on a 50-plus page marketing directive for one of my global consulting clients, worked hard on transitioning Oddpodz into a more social and user-friendly Website, and took my mom to Chicago for two days to see Oprah.

Early next week, I’ll blog about my trip to Chicago and the Oprah experience.

This week I’m focusing on an important aspect of entrepreneurship, or what I call “the high cost/high return of learning curves.” My goal is to share some lessons that hopefully will help you turn your learning curve experiences into meaningful milestones too.

Most of you know, the Oddpodz team has been at this community-building thing for a few years now. The founders had strong marketing and business backgrounds, however, none had technology expertise. But, we are a Web-based business so naturally the Oddpodz business model is reliant on technology.

Sound like a crazy path to take? And a bit risky? It was. But if you look at successful businesses throughout history, it’s not what they didn’t know that really mattered, it’s how they managed their weaknesses and leveraged their strengths.

Our company’s lack of in-house technology has definitely been one of our most challenging obstacles. This was evident from our first major Web site build in 2006. We hired the wrong Web development firm, expended over $400,000; lost 18 months in time-to-market, then realized our site was total crap and had to rebuild it just to meet basic functionality standards. During that time, we also needed to manage our content changes and hosting fees in a cost-effective manner, which brings us to today; we have our interim site up and running but with a whole new slew of flaws.

These could have killed us. But they didn’t. They made us stronger.

Fortunately, in 2007, when it came time to re-build and launch our second site, we connected with a Web development company that worked in .php open source (versus .net- or Microsoft-based), and also needed branding services, which I could provide. So we bartered about $40,000 in fees and kept our shaky train on the track. The good news, this technology time around, was that our leadership team was starting to gain a little ground on the IT learning curve. The new site was built with a much more user-friendly content management back-end called Joomla; we could make more updates ourselves. However, we were still very dependent on a fee-based, external team for support and many site changes.

Our second site was light years better than our first one, and it functioned. But soon after its launch, the honeymoon was over. Oddpodz was not generating revenues, our funding was gone, and the amount of cash we had to invest with our Web development company was not significant enough to get any timely service. This is one of the challenges of being small. Read more.

This put us in a very tough situation. Social media sites are continuously evolving. The industry is learning what users want from a Web site and community experience, new tools are becoming available; but without in-house technology expertise at the time, we were unable to move forward.

We needed to find a new Web service provider. Unfortunately, moving from one Web developer to another, or even finding an independent programmer can be risky, time-consuming, and potentially costly.

Even in a perfect world, a switch in developers can open up a can of worms. Custom programming and issues with workaround applications are discovered and then a blame game starts between the old and new resources.

For us, it all boiled down to Oddpodz having to choose its pain: stay and suffer, or switch and suffer.

I started researching alternate Web developers that knew Joomla. Through a Joomla training company, I was referred to several resources.

I soon found a company that I was comfortable with and they seemed to welcome small businesses accounts. I provided the contact with our back-end access so he could carefully look at our site before we made the move. He assured me his firm could help us and their fees and hosting costs would be substantially lower than what we had been paying. He also mentioned that our site was built in Joomla 1.0, which is no longer supported. He stressed the importance of upgrading of our site to Joomla 1.5 soon, or our site could experience all sorts of problems with no easy answers. We discussed upgrade costs and he said most conversions cost between $3,000-$4,000.

All of that sounded great to me; significantly reduce our hosting fees, upgrade our back end, and have a firm that seemed like it was truly interested in helping us with affordable services.

During this time of trying to source a new Web service provider, our current Web Company was beginning to generate more frustration. Our site programmer unexpectedly left and no one who remained seemed to have a clue what he had been doing for us. I felt like a change had to be made quickly.

So I pulled the trigger with the new company. This “simple move,” as sold to me, was not. This was due to both parties; the old company not being responsive to what the new company needed and the new company had not really looked under our hood while they were pitching us on the smooth hosting transition.

Yes, our site was moved to new servers. And we were saving some money. But at this point, lots of site functionality was lost for a host of reasons, including certain applications tied to old IP addresses. Others were just not available at all. Bottom line, we incurred $500.00 in troubleshooting fees just to get the site to function at 90 percent. Among the ten percent not functioning was our member sign up. So, if you came to our site, you could read content, but you couldn’t socialize or sign up as a new member.

This was not acceptable.

When I contacted our new Web developers, I was told that Oddpodz must upgrade to Joomla 1.5. But with this new information, the cost would not be $3,000-$4,000, but rather more like $16,000, and more for our testing time and involvement.

This totally sucked.

We would have been better off overpaying and getting under-serviced from the old company… at least the community worked.

Hence, my quandary: I believe Oddpodz can start generating revenues by offering tools and content for a fee. There are many successful sites that do this every day and one of our company’s strengths is creating solid content. But can we earn $16,000 in a few months to cover this investment? With our current team and resources, I don’t think so.

So what were our other options?

Using our in-house expertise, rebuild in WordPress, add an ecommerce section and focus on our strengths in content development? This would cost under $5,000.

Upgrade the site to Joomla 1.5, but scale back functionality? This would cost around $8,000?

Throw in the towel and just focus on my other businesses.

After much deliberation, I concluded we would rebuild in WordPress with our core team of contractors. We will leverage as many free tools as possible, build it slowly, and build it right.

This journey I just walked you through has been a big expensive pain. A lot of it was due to my and my partners’ lack of knowledge in Web technology, and not knowing what questions to ask the service providers when we engaged them.

Today, everyone is a lot smarter. And the company is still swimming toward success without water in its lungs.

The happy ending to these chapters of learning curves is, every one of these experiences taught us valuable lessons in technology and managing service providers. Even though these lessons are in hindsight, this entire learning curve has been a meaningful milestone.

1. Don’t let your fear of not knowing something stop your dream from launching.

2. Don’t let the fact that you don’t now beans about some part of the business stop you either. Life is a learning journey. Just know that it may get bumpy.

3. Don’t beat yourself up when you make mistakes. Stay focused on what you need to do to keep moving forward.

4. No matter how excited you are about building something, when you are making a big investment in your company, ask questions of yourself and your vendors about worst-case scenarios.

5. Don’t delegate a major project to a lone team member who does not have expertise in that area. As the leader of the company, don’t micro-manage, but do stay engaged with that person until you are enjoying smooth sailing.

6. If you have at least $100,000 to invest in technology, consider hiring someone (a programmer) who just works for you, not a company.

7. Beyond the time anyone says it takes to build a Website, add 10 percent for testing, and 10 percent for unforeseen changes.

8. Don’t build anything in a version of software that will soon be outdated, just to get something up, unless you are certain of the cost for the upgrade.

9. When a company is giving you a bid on a technology build project, if they have not thoroughly looked under your hood, be prepared for a higher cost.

10. Journal all your learning curves. At least once a year, pull them out and remind yourself of the progress you made because of them.

I am fortunate that in addition to Oddpodz, I operate a successful consulting practice. I can continue to fund and contribute to this company until we really start rocking and making some money.

Within the next 30 days you will see a new and improved site and community. It will still be a work in progress, but it will be another important milestone toward our success.

About the author: Karen Post, a.k.a. The Branding Diva® is an international authority on branding, marketing, and entrepreneurial matters. She has been featured as a business expert in print publications; on TV, radio, and on Web channels. Karen authored the best-selling book Brain Tattoos Creating Unique Brands That Stick in your Customers’ Minds and she is co-founder and CEO of