Is It Better to Start a Company at 25 or 45?

A VC An entry that Fred Wilson wrote back in May has been stuck in my mind. What’s the optimal age of being an entrepreneur?

It’s a bit of a contentious question. He started by asking innocently, “Do you know any 45 year old entrepreneurs?” Or rather, one of his friends asked him that.

Then Nick Denton of Valleywag picked it up and asked, “Is 30 too old to start a company?“, adding more fuel to the fire. Denton also selected some media darlings and compared the ages at which they founded their companies:

Valleywag Age Question Chart

Finally, Clay Shirky weighed in with what he referred to as the (Bayesian) Advantage of Youth:

I’m old enough to know a lot of things, just from life experience. I know that music comes from stores. I know that you have to try on pants before you buy them. I know that newspapers are where you get your political news and how you look for a job. …

In the last 15 years or so, I’ve had to unlearn every one of those things and a million others. This makes me a not-bad analyst, because I have to explain new technology to myself first — I’m too old to understand it natively. But it makes me a lousy entrepreneur.

So is 25 really a better age to start a company than 45?

Personally, I agree with Wilson’s conclusion: “I don’t totally buy that age matters. I think, as I said in my original post, that age is a mind set.”

Shirky has a point about inexperienced minds being able to make connections that more experienced minds wouldn’t see. Age can usually offer that, but not always. I know some really dumb young people.

One can also train one’s mind to think more creatively. IDEO is a famous example of a company that’s done just that. Then there’s also the Conceptual Innovator vs Experimental Innovator effect as well. So if you’re not 25 anymore, don’t lose heart!

What I believe to be more of a factor is not making mental connections and creativity — but risk. Creative thinking can strike at almost any age. But being able to take grand risks doesn’t; at least, not really.

In our society, the older we become, the more likely we’re in a situation where we have to care for a house & mortgage, an immediate & extended family, and a host of other responsibilities.

Compare that to a fresh college graduate with only him/herself and some school loans, and what do you see? A younger adult who’s realistically able to take greater risks.

That’s just an assumption, of course. But when Entrepreneur magazine recently published their “2007 Hot 500 Fastest-Growing Businesses in America” results, I thought: Ah!

What did they find was the average age of the entrepreneurs in their Hot 500? Forty-four! 44 years of age, for the average entrepreneur of one of America’s fastest growing businesses. Food for thought!

Their survey cover all sorts of businesses, tech and non-tech. Wilson, Denton, and Shirky, I believe, were thinking mainly about technology businesses. So it’s possible I’m comparing red apples to green apples here – same topic, but slightly different versions of that topic.

Still, I’m hopeful. It’s not the age that matters, it’s the mindset, the creativity, and the courage to take a big risk that matters.

Free Stuff to do in San Francisco

SF MOMA Being on your own means you have a lot more “free” time. Well, honestly, it’s not free, because any time you waste now is your own time. And time is money.

But if you’d like to take a break from business and do something cost-effective (read: free), then here are some suggestions:


Take a nice stroll through one of San Francisco’s wonderful parks. Walk your dog, read a book, go for a run. Or just breath in the fresh air.

Museums, Art Galleries, & Zoos

Soak in some culture and brain candy at these great institutions. After all, one of San Francisco’s main charms is its culture! Some are free only on certain days of the month, others are free all the time.


Tours can be full of fascinating knowledge and surprisingly fun. At the very least, they make for interesting conversation pieces or help jump-start your brain when you’re in a mental standstill.

Movies & Concerts

Sometimes it’s fun to just relax and watch a good movie or listen to a good performance. During the summer and fall, San Francisco is full of such fun events.

Book Readings & Story Tellings

Another great way to get your creative juices flowing is to experience the creativity of others. These bookstores and organizations offer book readings and story tellings by established and up-and-coming authors.

Free Wifi Cafes

And what list of free stuff would be complete without free wifi cafes? These sources all list lots of great free wifi hotspots in San Francisco.

I’m sure there are a ton of other free things you could do in San Francisco. This city is a treasure trove of culture and activities. I haven’t even listed the yearly events that take place. That could be a whole other article in itself.

Do you know of any other great free activities?

The Caffeine Curve

Now for some Friday fun. This pic seems to be circulating the Interweb quite a bit; a friend forwarded it to me earlier this week.

Every entrepreneur lives off of caffeine one way or another. So what exactly happens when we ingest copious amounts of caffeine throughout the day?

Glad you asked. As this highly-scientific chart shows, you can reach deity-level elation at your peak, for those wonderful orgasms of creativity. Then you can drop down so low that you’re playing Duck Hunt with your neighbor’s dog.

The Caffeine Curve

Colorado-based cartoonist Tom Edwards is behind this hilarity. He’s pretty sure that he’s “the only cartoonist in the world who distributes his one panel cartoon almost exclusively on wheel-thrown porcelain pots.”

I’m not sure if he intended this pic to be a viral marketing gem, but it seems to have worked. This pic is on Digg and countless other blogs. He’s cleverly included his name in the pic, enabling people like me to be able to hunt him down. A smarter tactic would have been to include his URL, but hey, either way, he’s still gaining notoriety.

If you’d like to monitor your daily caffeine intake, you can purchase a mug and support Tom’s art. As an added bonus, you can even fill your mug with your favorite caffeinated beverage. Fun!

The First Week

“How was your first week out?” I asked Eric. “Now that you’ve left your job, has it been great waking up and not having to go to work?”

He sat back in his chair. “The first week was great. I did a bunch of errands, got onto all the necessary social networks, and set up my routine. It was a lot of prep work.”

I nodded and took a sip of my coffee.

“The second week though, wasn’t as easy. That’s when reality began to set in,” he laughed.

“Oh? What do you mean?”

“When you’re working for a big company, it’s easy to screw around and waste time. But when you’re working for yourself, the time you waste is your own.”

“Ahhh…” I nodded slowly.

“I also miss my coworkers. I had a lot of good friends at work. It was easy to just get up and get coffee with them. Now, I can’t really do that.”

“I can see that. I had a lot of good friends at work too. I’m really going to miss them all.”

“Staying focused and motivated is hard too. It’s easy to get distracted. Sometimes I need to write down my goals helps me keep focused.”

I sipped my coffee and continued nodding.

“Staying at home can be a little cabin-feverish too, if not distracting. So I’d go out and work in a cafe or something.”

“That’s a good idea. I totally plan on working from cafes also.”

“I don’t about you, but for me, getting into a routine helps too. I decided to replace my morning commute with working out. So now I do that everyday, first thing in the morning.”

“That’s a really good idea.” I smiled. “A really good idea.”

“Finally, since I sometimes feel a little isolated, I make an effort to go out and meet with people. I’ve been calling up friends, ex-coworkers, former classmates, and doing lunch or coffee with them. I find it really helpful to stay socialized and in touch with people.”

I nodded. “That’s awesome advice man. Thanks!”

Eric smiled. “It’s not all fun and games. People think that when you quit your job, you’ll have a lot of fun. Not true if you’re an aspiring entrepreneur. Instead, you have to work really hard. But as long as you realize that, and keep focused on your goals, you can totally do it.”

Three Reasons to Become an Entrepreneur

I’ve been talking to many aspiring entrepreneurs lately. The question of Why usually comes up. Why do you want to become an entrepreneur? Why do you want to give up a steady, full-time job, to enter the uncertain world of business ownership?

From the responses I get, the answers seem to boil down to these three fundamental reasons:

  • To Be Independent

    You want to be your own boss, an employer, not an employee. You don’t want to work for The Man anymore. You want the flexibility to do what you want, when to do it, and how to do it.

  • To Be Wealthy

    You want to make a lot of money, to make millions. And you can’t do that with your 9-to-5. You’re aiming higher than financial security; you want financial comfort or financial wealth.

  • To Be Idealistic

    You want to change the world, to make a positive impact. You want to follow your dreams and do something you’re passionate about. You want to truly care about what you’re doing.

Each entrepreneur seems to be some combination of the three, in varying degrees.

Me, I’m mostly an idealist. I want to change the world, to fundamentally improve it. Being financially wealthy wouldn’t hurt either, especially since money is necessary for the kind of change I’m envisioning. Being my own boss isn’t as important, though it’s the ultimate test of my decision-making abilities.

How about you? Why do you want to become an entrepreneur?

My Last Week

Yahoo This is a sad week. It’s my last week as an employee of Yahoo! (YHOO).

The last week of a job is always sad. They’re always full of goodbye lunches and farewell drinks. Especially if you’ve been at the company a long time.

There was a time when I used to look forward to my last week at a job. Before Yahoo!, I would generally leave my job after about a year. That was my limit. One year. After that, I’d grow bored and crave a bigger challenge.

Yahoo!, however, was able to keep me challenged for nearly six years. That’s quite a feat, let me tell you. That’s not for a lack of competing job offers either. I was able to take on vastly different roles and responsibilities each year, partly because the company offered lots of opportunities, and partly because the company supported my initiative to take advantage of those opportunities.

But now it’s time for me to move on. I’m off to do my own thing, to be an entrepreneur.

No, it’s not Yahoo!; even if I worked somewhere else, this would still be my last week. No company could keep me right now.

You know what it is? It’s the desire to start something from the ground up. To build something great, yet viable—or starve. To not have that cushion of a steady paycheck and take very real risks. To follow your dreams, your passions, and your own path.

So I’m going into this last week with mixed feelings. There’s the excitement, of course (“Oh man, I’m finally doing it!”). There’s also nervousness (“What if I fail? What if I lose it all?”). And there’s loads of sadness (“I’m really, really going to miss my friends here”). Sniff.

Goodbye, Yahoo!.

Will Blog for Cash

What are all the ways to make money off your blog? When Darren Rowse of recently published his top income streams, it got me thinking.

My aim isn’t to make a living off my blog. I already have a job I love (it’s like getting paid for a hobby). But I’ll admit I’ve fantasized about making a side income from my blogs. And c’mon, what blogger hasn’t?

So far, there are three five main sources of income for blogs. All are essentially advertising vehicles for businesses, but with some differences.

UPDATED 12/16/2007: The lists below have been revised as I’ve gotten new info from advertisering providers.

  1. Ads
  2. Affiliate programs
  3. Job boards
  4. Paid reviews
  5. Video


There’s a wide variety of ad types from which to choose. First, there’s the UI of the ad: text, image, video, or RSS. Then there’s the payment method: CPC (cost per click), CPA (cost per action), or CPM (cost per 1000 impressions). Finally, there’s the ad selection: automatically matching your content, explicitly setting the criteria (category, location, keywords, etc), or a hybrid of both. Each will vary in revenue potential, depending on your blog’s content, audience, and popularity.

Affiliate Programs

Affiliate programs basically offer what look like ads for your blog, except they focus on the product or service sold by the parent business. Most offer CPA programs where bloggers get paid for qualified leads. A qualified lead is when a click from the blog leads to a sale. Bloggers get a share of this revenue.

Shopping comparison engines are an exception. They offer CPC affiliate programs because they earn their revenue not from sales, but from clicks from their site to their merchants. Bloggers get a share of this click revenue.

There are too many affiliate programs to list. They can range from direct providers (e.g. retail stores, mortgage providers, insurance companies, etc) to affiliate networks (third-party companies that have set up affiliate programs for others). What I have here are some of the more popular ones, including several affiliate program directories.

Direct Providers

Affiliate Networks

Shopping Comparison Engines

Lists of Affiliate Programs

Job Boards

Job boards are the newest offering on the block. They basically offer businesses a way to advertise their job listings on blogs – and bloggers get to set the price for hosting these job listings. Prices can range from $10 – $500, though bloggers aren’t paid until the job is “closed,” meaning the business hired someone that came through that blog. Essentially, this is a CPA model. One job board, HiddenNetwork, offers a CPM model instead.

This trend seems to be just the tip of something larger: CPA classified listings of any kind of product or service. Anyone, from large businesses to your neighbor down the street, could be creating these listings and advertising them on blogs soon.

Paid reviews

Paid reviews are a new and somewhat controversial form of word-of-mouth marketing using blogs. Business pay anywhere from $5 – $500 for each blog post written to review their product or service. A recent FTC ruling has made it necessary for bloggers to disclose that they’re getting paid for the posts too.


As embeded videos become more widespread on blogs, some companies are finding ways to monetize them through CPC video ads. Placed at the end of the videos, bloggers get a share of the revenue earned each time a video ad is clicked. The creator of the videos also get a share.

Good luck getting rich! And don’t forget the little people who helped you along the way!