Startups really aren't that new…

Targeted Delivery Date: February 1492

Dear Chris,

Congratulations on getting your start-up funded! I know how hard it is to close a first investment round like that — it's like herding cats, right? And those Angel investors are such prima donnas. It's like they think they are royalty or something! Oh, I see…I guess in your case they really are. It's also amazing how some people just don't have the vision. Kings of Portugal and England struggle with seeing the big picture. Smart move of yours to wait until all that fighting by Ferdinand and Isabella had finished before making your final pitch — timing is everything in these situations. And you have got to know when to step back from the table as well — so pretending to go off and look for other backers made them even more hungry. Great that you closed the investment from Queen Isabella — nice to see girl power is alive and well in the fifteenth century!

I've been looking through your business plan — and actually I do have a few questions/comments:

1. 1

   So, as I understand it, the plan is to sail west (rather than east) in order to find a quicker route to Asia — saves having to sail round Africa...which would be a real boon. That Cape of Storms, as named by Bartolomeu Dias (a Portuguese peer of yours, do you know him?), is a real challenge isn't it? No wonder they changed its name to Cape of Good Hope to make people less scared. That's a bit like an old Viking called Erik naming a place Greenland! However, assuming your plan works, I presume your unique selling point (USP) would be a reduction in shipping costs and timing for those valuable goods? Time is money, as they say — but I do have some concerns about your projections for the length of the voyage — 2,300 miles seems pretty short. I know this is based on your estimate of the circumference of the earth (and you, and most of your colleagues, already know the earth is round — none of this flat earth nonsense). However, I'd advise you to read up on that guy Eratosthenes (276–194 BC) — since his estimates seem reasonably sound and are at least 3x that of yours.

2. 2

   I am a bit worried about how you stop other competitors getting in on the action — i.e., won't the route quickly become public knowledge? I see that you plan to have all the sailors sign Non-Disclosure Agreements (NDAs) to protect your Intellectual property (IP). However, I see a couple of flaws in that approach. First, at least in England, most fifteenth century sailors tend to be illiterate and struggle even giving a thumb print (it's a scandal, I know, the adult education departments in our local authorities really need to up their game). Second, and again maybe it is different in Italy and Spain, but here in England if you take a random sailor down The Dog & Duck, ply him with a few pints of the landlord's finest ale, mention the word florin a couple times, they'll tell you whatever you want to know.

3. 3

   The term sheet for your investment is a bit unusual. I like the fact that you get a 10% cut on all the merchandise, and you get first option on buying into follow-on commercialisation at a discount, but what's this about you getting to be governor and overlord of new lands? I just wonder if that might be a bit distracting? Building communities is a specialist skill and very different to that of an entrepreneurial risk-taker. How broad is your leadership team? Do you have these roles covered? I'd recommend making sure your team is as diverse as possible — don't make that old mistake of keeping it in the family — it can lead to disaster. I know you want to be bold, but keep that cautious edge too — you don't want to be so far out in front that you are like the cowboy getting arrows in his back (hmm, maybe that analogy won't make sense to you yet, it's a bit "cart before the horse").

So, I wish you well as you prepare to launch v1.0 of your solution — your first voyage west on the Santa Maria. Remember that most start-ups usually end up doing something different to what was initially planned — it depends on what they find with that 1.0 product. So, keep an open mind as to what you find out there — it may be different from what you expect.

All the best,

p.s. Oh and try to make sure you are seen as the first. If you happen to come across any Viking artefacts, I'd keep that quiet...no point in scaring the investors unnecessarily.