What types of questions should I be asking before I sit on a board of advisors for a new startup?

The idea is a very small fraction of what it takes to earn the first million. Certainly billion. What actually matters is your ability to *execute*. Entrepreneurship means "having the talent of translating opportunities into money". Or, as Alexis Ohanian of Reddit said, "entrepreneur is just French for 'has ideas, does them'." As much as it may seem that transitioning off your 9-to-5 is the biggest hurdle, it's not. If you can't "get out of the gate" then you're also not ready to deal with the real challenges of business, like "competition that has 1,000x your funding" or "suppliers that jerk you around" or "customers who steal your intellectual property". It's easy to have a "billion dollar idea". I'd like to mine gold off of asteroids; I'm sure that would be worth billions. I'd also like to invest in Arctic real estate that will become coastal vacation property after fifty more years of warming. And, of course, to make a new social network that everyone loves. But saying these things is very very different from accomplishing them. Prove your concept by first taking a small step, such as making the first dollar. (Maybe try Noah Kagan's course at http://www.appsumo.com/how-make-your-first-dollar-open/). If you can't figure out a way to "make it go" without a giant investment, then you're kidding yourself about your ability to execute the business. If you *can* figure out a way to get a toehold, then by all means do it now! Happy to advise further, feel free to contact me for a call.

Kudos to you for seeing the value in great copy. I love that you mentioned 37signals, which is an organization that's made copywriting part of almost everyone's jobs (or so they've shared on their blog). MailChimp and Zendesk are two others that people often point to re: great copy that builds a brand and differentiates; Groupon is another awesome example of really, really tonal copy that people actually read (which is more than half the battle). MailChimp has in-house copywriters, including Kate Kiefer (https://twitter.com/katekiefer), and so does Groupon. I'm not sure who writes for Dropbox or Zendesk, though searching companies on LinkedIn can often reveal little-known in-house geniuses. The startups you mention have a certain style and tone that I have to say is different from what you'll normally get with a "direct response" copywriter, though by all means check out the link David Berman submitted to you because you never know. I recommend that, to achieve the slightly funky, funny-ish copy you're looking for, you seek out a conversion-focused copywriter with a creative and UX background. You need someone who's totally at ease adopting a new voice / tone and using it appropriately across your site and in your emails; less experienced copywriters might be heavy-handed with the tone, which often gets in the way of the user experience (e.g., button copy that's tonal can lead to confusion). Be careful, of course, not to push your writer to be exceptionally creative -- because a little touch of tone goes a loooong way for busy, scanning eyes. Here are some great freelance copywriters you could consider: http://copyhackers.com/freelance-copywriters-for-hire/ The link to Neville's Kopywriting peeps is also great. Before hiring, ask to see a portfolio or get a) links to websites they've written and b) a zip of emails they've written; if a writer is accepting clients, they'll usually showcase their work on their website. Check out their blog and tweets to see if their voice comes through in their own writing. Don't hire bloggers or content creators for a job a copywriter should do. Don't hire print copywriters for web work unless they do both. And when you find a great copywriter, trust them... and don't let them go - because 10 bucks says, they're in demand or about to be.

It all depends on what one decides to be a definition of a "success story." For some entrepreneurs, it might be getting acqui-hired, for some -- a $10M exit, for some -- a $200M exit, and for others -- an IPO. Based on the numbers I have anecdotally heard in conversations over the last decade or so, VCs fund about 1 in 350 ventures they see, and of all of these funded ventures, only about 1 in 10 become really successful (i.e. have a big exit or a successful IPO.) So you are looking at a 1 in 3500 chance of eventual venture success among all of the companies that try to get VC funding. (To put this number in perspective, US VCs invest in about 3000-3500 companies every year.) In addition, there might be a few others (say, maybe another 1-2 in every 10 companies that get VC investments) that get "decent" exits along the way, and hence could be categorized as somewhat successful depending on, again, how one chooses to define what qualifies as a "success story." Finally, there might also be companies that may never need or get around to seeking VC funding. One can, of course, find holes in the simplifying assumptions I have made here, but it doesn't really matter if that number instead is 1 in 1000 or 1 in 10000. The basic point being made here is just that the odds are heavily stacked against new ventures being successful. But that's also one of the distinguishing characteristics of entrepreneurs -- to go ahead and try to bring their idea to life despite the heavy odds. Sources of some of the numbers: http://www.nvca.org/ http://en.wikipedia.org/wiki/Ven... https://www.pwcmoneytree.com/MTP... http://paulgraham.com/future.html Here are others' calculations of the odds that lead to a similar conclusion: 1.Dear Entrepreneurs: Here's How Bad Your Odds Of Success Are http://www.businessinsider.com/startup-odds-of-success-2013-5 2.Why 99.997% Of Entrepreneurs May Want To Postpone Or Avoid VC -- Even If You Can Get It http://www.forbes.com/sites/dileeprao/2013/07/29/why-99-997-of-entrepreneurs-may-want-to-postpone-or-avoid-vc-even-if-you-can-get-it/

The previous answers given here are great, but I've copied a trick from legendary investor Monish Pabrai that I've used in previous startups that seems to work wonders -- especially if your company does direct B2B sales. Many Founders/ CEOs are hung up on having the Founder/ CEO/ President title. As others have mentioned, those titles have become somewhat devalued in today's world -- especially if you are in a sales meeting with a large organization. Many purchasing agents at large organizations are bombarded by Founders/ CEOs/ Presidents visiting them all day. This conveys the image that a) your company is relatively small (the CEO of GM never personally sells you a car) and b) you are probably the most knowledgeable person in the organization about your product, but once you land the account the client company will mostly be dealing with newly hired second level staff. Monish recommends that Founder/ CEOs hand out a business card that has the title "Head of Sales" or "VP of Sales". By working in the Head of Sales role, and by your ability to speak knowledgeably about the product, you will convey the message that a) every person in the organization is very knowledgeable about the ins and outs of the product (even the sales guys) and b) you will personally be available to answer the client's questions over the long run. I've used this effectively many times myself.

Cash money should be treated separately than sweat equity. There are practical reasons for this namely that sweat equity should always be granted in conjunction with a vesting agreement (standard in tech is 4 year but in other sectors, 3 is often the standard) but that cash money should not be subjected to vesting. Typically, if you're at the idea stage, the valuation of the actual cash going in (again for software) is anywhere between $300,000 and $1m (pre-money). If you're operating in any other type of industry, valuations would be much lower at the earliest stage. The best way to calculate sweat equity (in my experience) is to use this calculator as a guide: http://foundrs.com/. If you message me privately (via Clarity) with some more info on what the business is, I can tell you whether I would be helpful to you in a call.