5 years ago, I quit my day job and I started WordStream. The idea for my start-up was pretty simple: That paid search is potentially an incredibly effective way to grow your business, but unfortunately, you need to be a math wizard to make it actually work. Since most small businesses don’t have these kinds of skills (or the money to hire someone with those skills) our mission would be to develop software that would make it possible for millions of small businesses to be succesful.

In the last 5 years we’ve accomplished quite a lot! Today, we’re the industry leader in our market segment, we’ve developed innovative products and features like PPC Advisor and the 20 Minute PPC Work Week, we have many customers, and we’re growing remarkably fast! But it wasn’t always like this and so, this morning, on the bus ride to work, I jotted down 3 key things I’ve learned along my journey. Here they are!

1. It’s Really Hard!

Early on, when it’s just you and some idea, it’s pretty hard! If you don’t have a co-founder or angel investors, you basically need to figure out how to get people excited enough about your idea, to the point where you can convince them to quit their jobs and join you. Oh, and, you also need to figure out how to pay them.

When you’re working late at Panera Bread on your start-up, you will no-doubt experience some moments of weakness along the way, such as: Is this really going somewhere? Why am I sinking all my time and savings into this? I can definitely say that bootstraping Wordstream — developing a prototype, hiring talented people, bankrolling the operations, acquiring initial customers, and raising Series A Venture Capital financing was the most challenging thing I’ve ever done in my life.

Thanks to Gerard Escalante, Tom Demers, and Peter Swanton (WordStream’s first three employees) for taking the chance on me!

2. It’s Really Hard!

No, that’s not a copy-paste error! Even after you raise your first few million in venture capital, it actually gets harder. Sure you get perks like a new office (and… maybe a few other perks like a Coke machine, Wii, foosball table, heh.). But along with the perks, you have to tackle far bigger challenges like:

  • Establishing the company culture
  • Putting together an awesome team
  • Figuring out your target market
  • Designing an outstanding user experience
  • Developing a quality product that aligns with your target market and provides lasting value
  • Acquiring leads at scale
  • Providing incredible customer service
  • Finance stuff like LTV must be +3x more than COCA
  • Etc.

I’m incredibly thankful for my partner, WordStream CEO Ralph Folz, for his incredible leadership in tackling all this and more, as well as for the support of my amazing investors, Paul Flanagan (Sigma Partners) and Frank Andrasco (Egan Managed Capital).

3. It’s Totally Worth It!

On Tuesday this week, our AdWords Grader won the Massachusetts Innovation and Technology Exchange (MITX) Award for Best Customer Engagement Driver. MITX is the premier Internet business and marketing association in New England, and our award category was for technologies that are helping enterprises small and large drive their sales and marketing efforts and support their customers in ways that were not previously possible.

Not that this kind of validation is required or anything (nor are we anywhere near ”finished” with our journey as a start-up) but it’s an incredible honor to have won this, especially given the high caliber of companies that were also nominated for the award. (Congratulations fellow category nominees: HubSpot, Affinnova, SnapApp, TalkTo, and Vsnap!)

So right now, I just want to say thanks! To all the WordStreamers and customers who make WordStream the amazing company it is today. Thank you for everything that you do and for your continued business!