What I Wish I Knew When I Started My Company

Hiring, location, and good execution top the list of one entrepreneur’s things he wished he knew before he started out.

What I Wish I Knew When I Started My Company
[Image: trainman32 via Shutterstock]

It’s not often that you hit the ball out of the ballpark on your first swing, and all too often, the learning curve for entrepreneurs can be painful and expensive.


I was a core part of the founding team of three companies before my fourth, Assistly, was purchased by and relaunched as To say I learned a lot along the way is probably a bit of an understatement.

Through my current role as COO at, I meet many hot startups led by passionate entrepreneurs that have a great ideas and are attempting to bring them to market. When I’m asked for advice, here are the five things I tell them to keep in mind:

1. Focus On Your Expertise

My previous startup was a consumer email provider where the only real experience the founders had in the space was that we were consumers ourselves. It’s much harder to get a company off the ground when you don’t have a concrete problem to solve for a specific user–or the experience and domain knowledge to hit the ground running.

By the time we started our fourth company in the customer service space, Assistly, we had this down to a tee. We intimately knew the problem that we were trying to solve and what our target customer wanted; that focus was instrumental in helping us jump-start our product development and go to market efforts.

2. Execution Trumps Ideas

Many people believe that having a great idea is all you need to make your startup successful. It certainly helps, but that’s not the secret sauce.

I’ve heard of great ideas that burned through lots of money but never really got off the ground. I’ve also seen what many would classify as bad ideas turn into great products or companies. The most important difference in these two scenarios is how you execute. Hard work matters. Dedication and ownership matter. You need to instill this in everyone that’s a part of your team if you want to get to something meaningful.


3. Location Matters

My first startup was based out of Long Island and the next two were in San Diego. In both cases, the location suited the founders at that point in our lives. San Diego in particular is an amazing city, but for a software as a service (SaaS), business-to-business (B2B) startup, it lacks proximity to interested investors and potential customers.

While it’s possible to be successful anywhere, your message is amplified when you’re closer to your customers, investors, talent, other innovators, etc. The ecosystem makes things move faster and further. A serendipitous encounter in a coffee shop can lead to a product or business development that never would have occurred anywhere else. It’s really important to know where your market is, where you might be able to get capital, and who you want to partner with–and plant yourself nearby.

4. Hiring Great Talent Takes Longer Than You Think

One of the most challenging things about starting a new business, especially when you’re a minimally funded startup without local connections, is how to get the best people. We understood that mediocrity breeds mediocrity so we hired incredibly slowly at first. We worked through connections, social networking, job ads, and third-party recruiters to get our first critical hires.

We found great people, but it happened much more slowly than we had anticipated. The right people are worth waiting for, but when you map your strategy and roadmap, you need to either account for that or seek out more creative ways to accelerate.

5. Never Underestimate The Importance Of Customer Service

Given that I was one of the founders of a support software company, I see the value of offering awesome customer service every day. Some startups are so focused on getting the most viable product out the door that they don’t invest enough in offering great support from day one.

Great service completes the overall experience and can erase and overcome product problems. In the early days of we were able to make bug fixes for customers on a daily basis and get important features implemented on a weekly basis.


But, not all startups may have that ability. Even when you can’t be that reactive, letting customers know that you hear them, understand their issues, and are looking for ways to help goes a very long way. In addition to providing a great experience, you’re able to build word of mouth, goodwill, and a stronger community.

Of course luck still has a lot to do with becoming a successful entrepreneur. Even if you do everything right, if you aren’t in the right place at the right time, your ball still might not make it over the back fence.

But if you know what to expect, your learning curve might be a lot less steep. And a lot more fun.

Gary Benitt is founder and COO of (a company).