Typical Old & Young Mistakes; demographically specific hints

(I admit full guilt of stereotyping, bias, etc. I KNOW that these are gross generalizations with many exceptions, I hope they are helpful, not offensive)

Newbie, YOUNGER entrepreneurs:  You tell us nothing about team relevance.  Often times that is because it’s a bit of a stretch, but we’d love your best attempt.  We’ll expect you are going to put in the all-nighters, survive on a shoestring budget, live and breath your space, and hustle.  We want know how you are positioning yourself to beat others and are passionate about your space, even though you don’t have years of expertise to back it up.

You usually haven’t prepared enough – market dynamics, competitor deep dive (not just their pricing, but their rough costs and future strategy as best you can guess).  You tend to think like the end-user which is great, but usually you are the target of your proposed solution, make sure there is a broader appeal.  Validate that the business is attractive given the economics and external dynamics.

Newbie, OLDER entrepreneurs:  You spend too long explaining your background – your path through life, how much you know about the space, etc.  We know (and expect) you’ve been around the block, we want to hear the 1-minute, high-level summary.  If we want to know more, we’ll ask, believe me.  One unique item you should hint at (maybe not explicitly say): what is your risk profile given your personal responsibilities (family, mortgage, etc.)?

You also tend to come prepared in the wrong ways: decks too long (esp. over 20 pages!) and overly specific (how do you know the IRR or that your 4^th year revenue will be $63.7M).  I’d encourage you to think more from the perspective of the customer (how and why they’ll use it) and nail that – as you come from a generation focused on pushing products.  Read Steven Blank’s stuff.

REPEAT entrepreneurs: Why are you reading my blog?  Pitch me your next business, you know we love ya!  But seriously, don’t ride on your laurels – we know you understand the risks and emotional rollercoaster that is part of the course.  Highlight the biggest one or two mistakes you made, prove to us you can be self-critical and you are just as hungry this time around.

Many will claim to be ‘seasoned/repeat entrepreneurs’ that probably shouldn’t – be honest about your past business.  People claiming to be ‘successful’ entrepreneurs that are quickly revealed to have sold a piece of software they hacked together on the side of their day job for $10K in a fire sale just as you were shutting it down is interesting & relevant, but doesn’t quiet count and a successful exit or real start-up pursuit if you were holding down your normal job.  If we like what your building, we are going to do research on you, so all will be revealed…

Likewise having failures, of course, count positively (as long as you havent had a string of 10) – we’ll want to hear about these t0o.