Category: Q & A

It's the longterm potential versus the short-term payout. Put the ads up early, people may not get super excited and share your site with all their friends. Wait too long, and you may not be able to pay your hosting bills. Either could result in the death of your site.

Personally, I think anyone who isn't familiarizing themselves from day one with the various options for display advertising, how their various back ends work, etc, is putting themselves behind in the game when they do get to reasonable traction.

The typical blog doesn't look remotely spammy if it has a single sidebar text-only adsense unit, especially if the overall site is well designed, and the ad is both clearly separated from the content and subtly pushed into the background. Especially when you're just starting out, you can be doing a tremendous service to your readers – sending them to another site with more/better content. Plus, you get paid $0.02 for it! Everyone wins!

The important bit is this: Once you have ads, there will be a tremendous opportunity, and accompanying pressure, to increase their performance and value.

If you're a small blog or site, these efforts all rob time that you could be using to make your own site better, or at least procrastinate by answering web dev questions on Quora. Hypothetically speaking, of course.

When should one introduce advertising to a new website?

Depends almost entirely on your background/experience/skillset/desired working conditions.

If you are simply burnt out energy wise, then you need to take a break. Career burnout is just like physical muscle strain – if not dealt with immediately, it can create greater issues or even permanent damage longterm.

If you just feel directionless, but antsy/ready to jump back into the game, you might join an existing startup on an equity-only basis. Since you'll lack the stress of needing to pull in revenue/become profitable NOW will be less, you can potentially have all the pluses of the startup lifestyle without as many of the soul-crushing worries.

Save your own idea for a second startup, when you have the startup experience AND social proof under your belt of an exit/implosion at startup #1.

Oh yeah, and if you're a developer, and looking actively for a startup to join… 😉

What should I do if I'm ready to quit my 9-to-5 job, to run a startup but am burnt out?

Reduce the penalty of failure at the LOWER end of the economic scale, at least within reason. In the current economic client, entrepreneurship is not stifled by taxes, it is stifled by a lack of social supports that would allow prospective new businesses to try something groundbreaking, fail utterly, and not worry about having destroyed all hope of their own, and their family's future.

As things stand now, the penalties have only been removed for the largest businesses, the ones which also happen to be the slowest moving, most resistant to change, and unable to exploit new opportunities.

What next steps should be taken in the U.S. Congress to encourage/strengthen entrepreneurs?

It's dead simple: 100% of nothing is nothing. 10% of Google is more than you can spend in ten lifetimes.

When in doubt, split everything evenly between cofounders at your first startup. Giving it any more thought is a waste of time.

Don't lose an A player to haggling, and settle for a B or C who meets your terms. Fractional millions is a win in any record book, and you have a product to roll out, and competition that doesn't sleep, has spies in your organization, and knows what you look like naked.

Worst case scenario, you revel in all the stories you'll be able to tell people about how my Quora answer screwed you and got you kicked out of your own bazillion dollar company. Then order another $400 bottle of wine from the oceanside restaurant your yacht has pulled in to, before retiring to your 800 thread count sheets so you can cry truffle-scented tears into your duckling-feather pillows.

On a more serious note – if you've already put in a ton of time and effort, make sure that shows up in the vesting. 50% with a vesting advantage at least gives you solid control for a few years, or until an investor takes interest.

For the record, I also recommend a four year vest with no cliff – just 1/48th of their total share each month for each cofounder, starting from the moment they sign on board. To me, the one year cliff is just laziness – why would you hold on to someone who wasn't working out for a WHOLE YEAR? From the opposite side, why work for a vaporware company for a year with potentially zero return?Think about it…

How much equity should you give a CEO/Business Manager at a startup which has already started making some money?

While it's a newer site compared to things like Plancast.com or Meetup.com, you might try posting your question at http://www.quora.com, there are lots of helpful people on there generally, but the core group of regular users seem to be largely SF/SV-based tech entrepreneurs. 
 
By asking your question on quora you will most likely receive several well-researched and well-meaning answers, as well as uncover specific quora users who, by virtue of their responding to your query about making connections, will most likely themselves be interested (or at least open) to meeting a fresh-faced startup newbie, and introducing them to their favorite events/people in the area.

Good luck and welcome!

What's are some great ways to make tech and startup connections?