Reflection · Hard questions

The One Question Every Entrepreneur Should Ask Themselves....

Jessica Alter Entrepreneur & Advisor

May 22nd, 2013

We just posted a blog about the importance of gut checking yourself and the big picture as an entrepreneur: http://founderdating.com/the-one-question-every-entrepreneur-should-ask-themself/

Curious to hear other's thoughts from the community on moments you've realized you were or were not really doing what they want to do or how you gut check yourself....

Lona Duncan

May 22nd, 2013

I'm on my third company and my experience of entrepreneurship has been  "like eating glass and staring into the abyss of death."  However every time I check in with myself, there's nothing else I'd rather do.  Getting a job and being employee number 4,987 at X company sounds like a slow painful death to me.

Therefore I can not stay away from entrepreneurship. Its like a drug and even though it hurts more than it pleases I can not get enough of it.

Thomas Knoll Executive Advisor & Business Coach. I help entrepreneurs survive and thrive at building their teams and businesses.

May 22nd, 2013

These rough times are automatic reminders to ask this question... what can be even more dangerous is when things are going really well according to external measurements and an entrepreneur doesn't feel like they can ask that question.

Rex Farrand Sr. Account Manager @ PlaceIQ | Founder at Simplex Digital

May 22nd, 2013

As LinkedIn's Reid Hoffman says, stop asking what is in it for you, but what is in it for everyone else?  Translation: What market exists, with what problem, and how do you fit it?  (Hint: Don't over think this).

Rex Farrand
@rexfarrand

Joseph Moniz Software Engineer

May 22nd, 2013

I whole heartedly agree. Every career move i've made in my life has been based off of me optimizing for happiness. For me the biggest joys in life are having huge impact in peoples lives and solving hard problems. If i haven't been able to do even one of those i'll move onto the next thing unconditionally.

- Joseph Moniz


"Wake up early, Stay up late, Change the world"

Rob G

May 22nd, 2013

i'm on my 4th. It is essential to build 'think time' into your week - go run, ride your bike, surf, whatever it takes to get above the trees so you can see the forest. Entrepreneurship is about calculated risks...don't forget to listen to your internal calculator.  Entrepreneurship is about questioning the status quo...both external and internal.   

Paul O'Brien

May 22nd, 2013

Great question though I've heard it perhaps better asked, WHY am I doing THIS?

The one oversight many entrepreneurs make in trying to define their business objectives, raise capital, get traction, build a team, etc. is WHY?  

We often develop our understanding of the exit strategies available.  We talk of just wanting to solve a problem.  We get excited about the prospect of an acquisition (or even more exciting but incredibly unlikely, an IPO).  But the goal that VCs pick up on, potential partners infer, those joining the team, is WHY as it pertains to what's in it for me?

Important distinction?
Ultimately, the direction a new venture goes is dependent on the personal goal of the entrepreneur.  Is this a lifestyle business in which they'll be satisfied with a steady stream of income?  Is an exit at $10-$20M  acceptable or do the founders want to hold out?  Are you providing a service and plan to grow methodically and safely?  OR is this a game changing innovation with global aspirations the likes of Google?  

It's easy to look at the tech, business model, and potential and have AN answer to that question, but if your answer is inconsistent with that of the founders, you're going to mismatch expectations and have a challenge.