How much of a set plan do you need to have from the outset of a startup? Is launching, learning and adapting over time the wrong approach?

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/

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.

As you may suspect, there really isn't a hard and fast answer. You can review averages to see that a CEO typically becomes a major shareholder in a startup, but your role and renumeration will be based on the perceived value you bring to the organization. You value someone's contribution through equity when you think that they will be able to add long-term benefits, you would prefer that they don't move company part way through the process, and to keep them from being enticed by a better salary (a reason for equity tied to a vesting arrangement). Another reason is when the company doesn't have salary money available but the potential is very strong. In this situation you should be especially diligent in your analysis because you will realize that even the best laid plans sometimes fall completely short. So to get the best mix, you have to be very real about the company's long-term growth potential, your role in achieving it, and the current liquidity necessary to run the operations. It should also be realized that equity needs to be distributed. You cannot distribute 110% and having your cap table recalculated such that your 5% turns into 1% in order to make room for the newly hired head of technology is rather demotivating for the team. Equity should be used to entice a valuable person to join, stay, and contribute. It should not be used in leu of salary that allows an employee to pay their bills. So, like a lot of questions, the answer is really, it depends. Analyzing the true picture of your long-term potential will allow you to more easily determine the correct mix.

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.

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.