Startup Q&A

by jeffhilimire on August 28, 2009

I had the great pleasure of doing a short interview with a friend who’s interested in being an entrepreneur.  I’m always humbled that someone would want my advice.  Typically I only have one bit of advice: Just do the damn thing (and nothing else).  The “nothing else” is perhaps the most important.  You can’t do this on the side.  Sorry, just not going to happen unless you put everything into it.

Anyhow, some of his questions were new to me so I decided to throw the piece up here for anyone interested.

What’s the best advice you’ve ever received in life? And what’s the best advice you would pass on?

I get asked this question a lot and unfortunately I don’t have a good answer for it.  I’ve received a TON of great advice over the years, mostly from the advisory board that I put together.  It’d be too hard to isolate it down to one.  But that flows nicely into my advice to pass along: PUT TOGETHER AN ADVISORY BOARD.  You need people around you to give you advice and creating one was easily one of the best things I ever did to help be successful.

What has been the biggest challenge in your career?

Cash.  When you’re starting out, cash is your life blood.  Running out of money is the #1 killer of startups.  I can’t tell you how many credit cards I juggled trying to get my company started.  Be frugal and savor every dollar.

How did your business model evolve from initial concept to launch? Were other parties responsible in this evolution?

Our business model stayed fairly the same, even though it took us over 10 years to build the company and sell it.  Our differentiator changed and we added some services along the way, but we were pretty focused on being a digital agency and tried never to sway from that.

What’s the biggest DO and DONT of starting a company?

DO: quit your day job.  You can’t do it on the side, period.

DON’T: think you’re the only one doing this.  Research your competition (there is ALWAYS competition).

DO: be confident AND humble at the same time.  Strive for humility while always believing in yourself.

DON’T: forget to celebrate every success.  It’s easy to get bogged down in the details and problems.  Look up and celebrate!

Looking back, is there anything you would have done differently in building your business? If so, what would that be and why?

Nope.  Every mistake we made led us to make better decisions going forward.  The mistakes are what make you successful.

If you had to choose one trait or characteristic that defines a successful business, what would that be and why?

Flexibility.  You have to be willing to allow your business to change as your customers or the market demand it.  Read “Founders at Work” and you’ll see what I mean.

How did you balance management and ensuring the evolution/implementation of your idea?

I had 3 amazing partners that helped me steer the ship.  It doesn’t always work out this way, but we were friends before and remained friends during.  Having that trust is invaluable and something that allowed us to evolve and manage the business successfully.

Not only ‘how did you raise capital’, but what financing options were available to you at the time of start-up and now?

We didn’t seek funding the way that startups typically do.  Instead, we kept costs as low as possible and (not that I’m suggesting this) we maxed out every credit card we could get our hands on.  When we finally didn’t need a line of credit from the bank (after trying for YEARS to get one), they gave us one.  As soon as you can do that, even if you don’t need it, do it!  Banks will only give you money when you don’t need it, so get it while the getting’s good.

As an entrepreneur, how do you know to recognize the distinction between dogged perseverance and blind stubbornness? Is there a difference?

This is a fantastic question.  I only know dogged perseverance.  I’m sure there were times in my career where people felt like I was being stubborn but I always believed and put everything into making the company work.  You have to have that in order make it happen.  I break it down to when people are telling you to quit and you’ll never make it, be dogged in your perseverance.  When customers are giving you suggestions, try hard not to be blindly stubborn.

  • hannonhill

    Great post Jeff. I agree that you need to just put yourself out there full-time and treat it like a marathon and not a sprint. Here are my thoughts on the topic:
    http://davidcummings.org/2009/08/28/five-habits

  • johnwaddy

    Great advice Jeff. Reminds me of a quote I like:

    Good judgment comes from experience, and experience comes from bad judgment

    Building a successful business is the hardest and best thing I ever did. In the beginning, it is hard to keep going when you don't know if you are going to make it. After you make it past break even, you are lucky if you are not burned out. But once you've done it, you know you will never work for anyone else again – unless they give you millions of dollars :)

  • http://www.jeffhilimire.com Jeff Hilimire

    I love that quote, “Good judgment comes from experience, and experience comes from bad judgment.”

  • http://www.jeffhilimire.com Jeff Hilimire

    Awesome post. Every entrepreneur should follow David's 5 habits plan:

    1. Read one of the Personal MBA books every other week until you’ve finished all of them, and then never stop reading a highly recommended book every other week
    2. Have lunch with an entrepreneur you don’t know well every week and prepare a casual list of questions that you’d like to know his/her thoughts on
    3. Join an EO-like organization immediately for peer-to-peer accountability groups and get actively involved on the board in a leadership role
    4. Improve at least one thing in your business every week and don’t be afraid to try improvements that will fail
    5. Actively re-evaluate your company corporate culture on a monthly basis and continually make it better knowing that your corporate culture is the most sacred thing you’ll spend time on as an entrepreneur

  • http://www.jeffhilimire.com Jeff Hilimire

    I love that quote, “Good judgment comes from experience, and experience comes from bad judgment.”

  • http://www.jeffhilimire.com Jeff Hilimire

    Awesome post. Every entrepreneur should follow David's 5 habits plan:

    1. Read one of the Personal MBA books every other week until you’ve finished all of them, and then never stop reading a highly recommended book every other week
    2. Have lunch with an entrepreneur you don’t know well every week and prepare a casual list of questions that you’d like to know his/her thoughts on
    3. Join an EO-like organization immediately for peer-to-peer accountability groups and get actively involved on the board in a leadership role
    4. Improve at least one thing in your business every week and don’t be afraid to try improvements that will fail
    5. Actively re-evaluate your company corporate culture on a monthly basis and continually make it better knowing that your corporate culture is the most sacred thing you’ll spend time on as an entrepreneur

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