Monday, May 28, 2007
I know that's an odd title, but I think it's true.
The Chinese have a great saying that puts everything into perspective:
"Every 100 years- All new people".
Think about that. It's effectively true. For the vast majority of people on Earth, their time here is nothing more than a blink of the eye and then they're gone. Poof. Dust. Forgotten.
Unless they write a blog.
I suspect that, 1000 years from now, your blogged words, thoughts, ideas, rants and tirades will, somehow, somewhere, still be stored in the Googleplex, or on the Internet (or it's equivalent) and accessible. Effectively the only thing left of you long after you're dead and gone.
I doubt anything else you do with your life will have that kind of personal staying power. Maybe if you write a book or record a song, but that's not something the average person does. The only other thing that might be really equal in representing you, and what is uniquely you is the DNA you pass on to your children.
Even then, your thoughts via blog are more personal, public and representative of you when you were alive and spewing energy into the void.
I've always known whatever I wrote here was available to anyone, anywhere. What I didn't think about before was that also means anytime. Now, or 1000 years from now.
This stuff isn't going away anymore. The internet saves everything somewhere.
I'm sure you've all thought of this already and you're doing the 'so what'. Still, the TIME aspect and what that means to a human with a deterministically short (<100 years) existence never really sunk in until recently.
Time to go read a book. :)
Sunday, May 27, 2007
I look at what I've done with ClickCaster, which was a traditional angel model. First the founder invests his own money/time/resources to get an idea to a certain point (a team that delivers, a market identified, a beta product in production) and then he goes for either angel money or VC money depending on how big his/her plans are. In high tech/internet, with the costs to get to the next level so low, it's usually angel money. Certainly less than $1m, and usually half that; call it $500K average.
So I'm an angel investor, and I've got, say, $50 or $100K into an angel round of an early stage startup. I've put a pretty fair amount of betting money into this one deal. Is that good? Is it the most efficient way to invest money on high risk ventures? Until recently, I'd have said yes. Now, I'm not so sure.
David Cohen's TechStars is bringing in 10 groups at $10-15K investment each. Invested amount of around $150K total. Another $50K for things like creating a space for 3 months for them to work out of, maybe some datacenter setup with servers and bandwidth everyone can use to prototype on and some computers in the space they'll work in.
$200K. 10 companies. 20-30 hungry and foolish entrepreneurs with big dreams. Out of that you're likely to get 1 or 2, maybe 3 real companies that get their claws dug into a real market. For the money put in, you get 5-6% of the company. But they've been seriously vetted to get there. Maybe 200 applicants for 10 slots of which 2 companies will emerge. That's a hell of an efficient tunnel that happens in very short order (2 months to screen the 200, 3 months to screen the 10). Get your other legal, data center, entrepreneur and angel friends to help out and, man, you've got a wisdom of crowds market that, I suspect, kicks ass on the traditional angel investing or even early stage VC model.
Old news to many of you I'm sure, but here's what's new news (at least to me).
I put in about $200K of my own money for ClickCaster and a couple of years of my life (so far). I'm over 40, I've got some money to bet, I'm reasonably smart. I've been involved in starting things for a couple of decades, I'm well versed in the high tech/internet space and I want to get involved in the startup world.
Would doing a hatchery have been a better approach than focusing on a single company? Should a guy like me do this as opposed to a single focused startup with that $200K?
I don't know the answer, but I would bet big that several thousand guys like me, and angel investors who already have networks of friends, VC's and resources needed to do startups, are having this exact thought right about now.
They're watching TechStars and Ycombinator and the other hatchery's and looking to see if this way of filtering ideas, people and markets is the best approach for this particular investment sector.
If I were an entrepreneurs or angel investor (or a wanna be) who was looking for what's next, I'd want to talk with David and gang, get the initial formula/playbook (and blessings), move to Austin, Santa Fe, Iowa City, Portland or any of a couple of dozen smaller cities with high quality of life, a university, get plugged into the local scene and fire it up.
One side note on Hatchery's vs. Incubators:
David likes to point out this is not the old bubble days incubator approach. An incubator owned a larger percentage of the companies, was more deeply involved in the day to day business and didn't have a well defined near future endpoint when the money stopped, dead, and you were kicked out of the nest to live or die.
A hatchery is fast, ruthless in it's selection process and, after everyone involved votes (by what I can tell, with angel or even VC money) shuts down the 7-8 companies that didn't make the cut and does everything it can to help the 2-3 survivors.
Darwin, I think, would be proud.
Wednesday, May 16, 2007
The "bad news for graybeards as entrepreneurs" meme rears it's head again- or - In defense of the over 40 entrepreneur
Here we go again. Now Valleywag says you can only do a really big win startup if you're in your 20's and then Fred Wilson back peddles (sort of) on his back peddle about funding in their 20's vs. over 40 entrepreneurs .
Bad news for the graybeards: a quick check on the great tech companies of the last three decades shows a pretty brutal rule. The most spectacular successes are launched by founders still in their twenties. The peak age: 26. Within a year of that age were Google's Sergey Brin and Larry Page, Apple's Steve Wozniak, Yahoo's Jerry Yang, Skype's Janus Friis, Chad Hurley from Youtube, and Tom Anderson from Myspace. Full post hereFred:
So I don't know if youth is an advantage in the tech/startup world, but it certainly isn't a disadvantage. And I see our job as being able to work with young entrepreneurs in a way that allows them to be their best while helping them where they need it. It's something we are working very hard on perfecting. Full post here.At least Fred tempers his with 'it's a state of mind' more than anything else. He's right. It IS a state of mind. I refer, again, to my post last year "Are early stage start ups and normal lives incompatible?"
Of course a 23 year old with no family, no mortgage, no kids, no college funds, no IRA or 401K to fund in perfect health (and no medical or health insurance bills), a paid for 1990 volvo and 3 roommates (who are also your co-founders), no cube life/big company work experience with the requisite cynicism/dilbert disease and with no fear and a 140 IQ unimpaired by 20 years of (pick one): Drinking, drugs, bad relationships, lousy kids, all of the above bills, etc. has an advantage.
Life can wear you down. And it does most people. Doing a startup requires dedication, focus, naive belief in the impossible, more dedication, long hours and sacrificing 'life balance'; at least for awhile. That's why alot of entrepreneurs kill themselves and succeed (or fail) take off a few months (or in some cases a few years if the battle was particularly gruesome) and do it again.
I would put forth that it takes a particular (some would say peculiar, others would say slightly warped) personality type that's similar in some ways to the addictive personality to do a startup company. In our case, the addiction is the process of creating something useful and valuable from nothing and marshaling it through all the creativity, elation, pain, fear and fun that doing it entails.
Age isn't the defining factor. However, it does change the equation. I would bet fewer over 40's have it in them to do it than the same personality type does in their 20's, for instance.
Our society tries it's best to beat individuality and creativity out of you as soon as you hit 'the workforce'.
Even the good companies do it. Near the end of my tenure at Apple, my boss had an executive consultant (who worked with executives and CEO's to make them them better at their jobs) work with his reports. She set up as series of meetings with me for a 6 week period. In our first meeting, we talked for 4 hours. At the end of it, she said "Scott, I'm cancelling the rest of our meetings'. Thinking I'd done something wrong I asked why. She said "your one of those guys that drive corporations crazy. You have the qualities all of them are trying to bring out in themselves, but they can't control you. They want to find a way to tame it, and still have it. If I put you through this, it's like taming a wild stallion (no shit, that's exactly the phrase she used) and this company needs people like you". My boss was a little pissed, but, interestingly, he also gave me alot more funding and leeway after that.
Most people in their 40's have had it beaten out of them. Even big company senior execs and CEO's (there's a whole consulting industry built around it). Them, maybe, more than most.
But some of us survive the process. Not many, but some. And those of us that do are the over 40's that are capable of doing startups.
And we bring experience, contacts and resources no 23 year old has.
So...if we over 40's successfully run the product, market and funding gauntlet alongside the 20 somethings, even with a graybeard, we shouldn't be written off or filtered out just because of a birthday.
Granted, I'm biased, but if you ask me, smart investors should seek out that hard to find seasoned just right over 40 entrepreneur. There's likely 1 of us for every hundred 20 somethings of like mind, but if you can find us, we're worth it.
Tuesday, May 15, 2007
David Cohen, of TechStars (www.techstars.org) a huge supporter of entrepreneurship in Colorado (www.coloradostartups.com) , and Angel investor, has a series he and Brad Feld do called Big or Bullshit. He just wrote one on Vertical Social Networks.
His question is: Will they ever be big enough to be worthy investments? His second question is: Doesn't the aggregation of these networks contain more value?
On the first one, I say: big, not bullshit. Why? Community. We're communal animals and community has been part of how humans operate from the beginning. We're clever beasts though and we use our tools to improve community. I won't go through a history of it here, but I'll start with computers. In the early 80's, modems became available to the average person. What's one of the first things we did? We wrote BBS's(Bulletin Board Systems). Each tended toward specific communities. The whole social networking phenom of today isn't new, it's just more common to have the tools in your day to day life. In 1982, few people had personal computers. Today, the majority of US households do. Put a cell phone in the mix (which is becoming the PC of choice for the rest of the world), and you have the tools you need to participate. Social Networking is just better interface, easier to use and more realtime communications and richer media. MySpace is just one big BBS system with more advanced user tools.
Can verticals be valuable enough to be worth investing in? Again: yes. It all depends on the drivers. Here's an excerpt from an article from CNN's Business 2.0 magazine on one set of verticals (note that the title is a bit sensationalized, this is, after all, CNN territory):
The accidental 'friend' finder
(Business 2.0 Magazine) -- You know how you'll be trying to do work, and the Internet will inexorably drag you into porn? That's exactly what happened to Andrew Conru's career.
A mechanical engineering doctoral student at Stanford who grew up with churchgoing Lutheran parents in northern Indiana--the kind of guy who holds the door for everyone until he gets stuck there so long that someone has to make a joke so he can let go--Conru started the first online dating site, WebPersonals, in the early '90s. He sold it in 1995, pocketed a minor windfall, and started all over again.
Now he owns 27 sites under an umbrella company called Various, controlling twice as much online dating traffic as better-known rivals Match.com and Yahoo (Charts) Personals. But his clients tend to be much more fun. That's because most of them post pictures in which they're having sex. When you've already seen your date naked, it's a lot easier to focus on what she's saying.
Of all the dating sites Conru has launched--ones for Latinos, seniors, Asians, Jews, churchgoers--the biggest by far is AdultFriendFinder, which accounts for more than 60 percent of Various's revenue. Conru says his privately held, 450-person company brings in well over $200 million in annual revenue, averaging 40 percent growth for the past nine years. With more than 35 million visitors in 2006 and 75,000 new users registering each day, AFF ranks among the 100 most popular sites in the United States.
OK, I'll grant you, this is effectively adult content and we all know how popular that is. But this (if you take recent numbers on the porn industry in the US into account) is around 8-10% of the entire adult business take in the US (about $2.4B in 2006). And non of it is professionally produced. It's all user generated social networking DNA at work.
People are passionate about sex (doh!) but what about their dogs? Music? Religion? Politics? It's all based on the driver and if that driver is something emotionally important to that community, that's powerful stuff. Will Dogster get to $200 Million a year in revenue? I doubt it, but $20 million? Yea, that I can see happening. And that's a marketcap in the $150-200M range. Not a bad investment if you ask me.
The packaging of these (and using the same infrastructure, development and some content) is where you can get to FriendFinder levels of revenue and profit. How about Petster Inc. doing a Dogster, Catster, Snakester, Birdster, Fishster, etc.? Go down the long tail and add it all up. Dogs and Cats-the most popular pets (the head): Say, $30 million (60%). All the rest (the long tail), say $20 million (40%). That's up to a $500M marketcap potential there if you play it right.
Second are his observations on aggregators. He says, take the idea of OpenID and expand it into your 'full profile'. These will take off as well, but for different reasons centered mostly around convenience for the user and the perceived, by the user, value of that information. As we become more sophisticated about the value of our own personal information habits online (your Clickstream) we'll want to control that and gain some financial advantages for our attention (discounts, coupons, better targeting of the ads we know we have to see anyway, etc). That's not community though. There's nothing social about it (if anything I'd say it's more selfish than social). Is it a business? Absolutely. A big one? Most likely yes, but it'll take average people becoming aware of the value of their attention first. That's going to take time.
In the meantime, everyone loves their dog.
If I was thinking 'next 3-5 years' and had to pick vertical social networks or social network aggregators, I'd put my money on the vertical social networks.
I received an email from a good friend who I have alot of respect for about my last post on Mark Udall, Colorado Congressman. He's got his supporters it would seem.
I'm also impressed with Udall himself. I emailed him directly and in less than 12 hours got a response that was similar to what my friend sent. The email from Udall was a cut and paste, but hey.. it answered my question. Rarely do I get a response to an email when I write a politician, and when I do, it's not on topic or some lame 'we appreciate your input' and then a pitch for money. To be fair to Udall, here's what my friend sent:
Udall Supports Iraq-Afghanistan Spending Bill To Take America In A New Direction
I voted for the Iraq supplemental spending bill because it will make sure that America's soldiers get the equipment and resources they need and the top-quality health care they may require when they come home. This bill holds the president and the Iraqi government accountable to the benchmarks they have set for themselves and it is an important step toward what I think must be our goal - a responsible end to the war in Iraq, based on a strategy of phased withdrawal, accelerated diplomacy and troop redeployment that avoids the crossfire of civil war.
The bill includes a goal of March 2008 for completing the redeployment of U.S. combat troops, and allows enough troops to remain to protect U.S. military and civilians in Iraq, conduct counterterrorism operations, and train Iraqi soldiers.
I remain convinced that we should steer clear of arbitrary public deadlines for military actions and focus instead on realistic diplomatic and political goals. Our military needs flexibility to be able to link movements of U.S. troops to the realities of the situation on the ground, and successful diplomacy requires this flexibility as well.
We are four years into a war the president told us would be short and decisive. The Bush administration's misjudgments, lack of planning and poor leadership have made a bad situation worse - and the "surge" is no substitute for what is needed, which is a strategy for containing civil war and a wider regional war.
I opposed giving the president the authority to wage war against Iraq, and whatever may be said about the wisdom of invading Iraq, the fact is that we are still deeply engaged there. So long as our troops are in the field, we must provide them what they need. And we must extricate them from this emerging civil war.
We need to be scaling back our military mission in Iraq. We need to make the U.S. military footprint lighter to salvage a critical measure of security and stability in a region of the world that we can ill afford to abandon.The president's decision to take the nation to war has made our country less safe. We need to change course and chart a path that enhances our national security and sets the right priorities for the war on terrorism and struggle against extremists.
Saturday, May 12, 2007
I haven't been writing much about politics of late but I just found out that the congressman for my area here in Boulder, Democrat (?) Mark Udall, voted against the McGovern Bill to get us out of Iraq. One of 59 democrats to do so. And one of only 13 in districts that carried Kerry in 2004. From the CommonDreams.org blog:
Thursday the House voted on a slightly revised version of the McGovern bill. It would have mandated the beginning of withdrawal (”redeployment”) of U.S. forces from Iraq within 90 days and completion of the withdrawal (”redeployment”) of most U.S. forces from Iraq within 180 days after thatThe bill was defeated 171-255. 59 Democrats joined almost all Republicans in voting no.
The roll call is here:http://clerk.house.gov/evs/2007/roll330.xmlI think it's pretty clear to everyone who's been paying attention to all the facts that as far as the Iraq War is concerned, this is one dog that just won't hunt.
State District Rep. 04Bush 04Kerry California 28 Howard Berman 28% 71% Colorado 2 Mark Udall 30% 67% Georgia 13 David Scott 37% 62% Illinois 3 Daniel Lipinski 41% 59% Nevada 1 Shelley Berkley 42% 57% Maryland 5 Steny Hoyer 42% 57% Pennsylvania 13 Allyson Schwartz 43% 56% Texas 29 Gene Green 44% 55% Maryland 2 Dutch Ruppersberger 45% 54% Georgia 12 John Barrow 46% 53% Tennessee 5 Jim Cooper 47% 52% California 20 Jim Costa 48% 51% Wisconsin 3 Ron Kind 48% 51%
I'm not a Democrat (or a Republican), I'm a Libertarian Hippie. I'm liberal on some things, conservative on others. But I'm no fool. The fact is, all of my left leaning friends are against this war. Interestingly, most of my right leaning friends (if you draw them out) are as well. All you have to do is look objectively at the facts (which have been clearly articulated in many other places so I won't repeat them here).
I think Udall needs a good whack upside the head. I think a primary challenge for Mr. Udall might be in order.
The amount of money spent on this war (around $450 billion, so far) could have funded education, healthcare, budget imbalances and a dozen other more worthy causes. And then there's the over 3000 dead American solders (with the death toll going up daily). with 10's of thousands more crippled for life.
For what, exactly? I'm generally not dense, but I cannot see why we're doing this.
If you live in the 2nd district in Colorado, email Udall. Tell him you're PO'd. Hell, email him if you don't live here.
Yes. A primary challenge, especially for the 13 democrats in districts that went Kerry in 2008. Something to be considered very seriously.
Thursday, May 10, 2007
I love this.
I've been a huge supporter of the Creative Commons movement over the last 3 years (we built it into ClickCaster from day one).
From their website:
Creative Commons provides free tools that let authors, scientists, artists, and educators easily mark their creative work with the freedoms they want it to carry. You can use CC to change your copyright terms from "All Rights Reserved" to "Some Rights Reserved."It looks like Andrew Hyde is putting together a get together for creative types in Boulder to talk more about it and, maybe, spread the word a bit. From his blog:
If I can, I'm planning on being there.
In Boulder there is a problem. There are hundreds of talented creative professionals working and creating some beautiful stuff, but you ask them to name some names at other companies they draw a blank. Our community, and design can only go so far in our isolated pockets. Let’s get together and start the conversation.I would like to invite you to the first Boulder Creative Commons. It will be an informal gathering of creatives of all types at my office in Boulder on Thursday, May 17th. 1035 Pearl St. 4th Floor. I will provide drinks and some snacks.
If you'd like more on what it's all about, check it out at the main creative commons site.
Thursday, May 03, 2007
OK, I've been doing this for a couple of years now and I've had enough people ask me about the experience that it's worth writing up a blog post on my observations for folks like me who are over 40 who want to do their first startup. Fred Wilson's post on mid life entrepreneurs (which initially implied it was less than positive to be an over 40 startup guy, then backed away from the premise in a second post) also got me thinking that this might be useful to the people that are thinking of doing this but aren't sure of what it takes.
There's a followup blog from Paul Kedrosky about how he disagree's with Fred and how the average ages of entrepreneurs is actually pretty broad. He blogs about it here. Some interesting facts from Paul's post.
- The average age of Inc Hot 100 members is 41, but there is huge spread
- U.K. data shows that while the average of entrepreneurs there is 36, there is little age difference between that group the rest of the working population. Matter of fact, 23% of entrepreneurs there are between 45 and 54
1) Having a balanced life and doing a startup isn't an easy thing to do.
See my post on early stage startups and normal lives. I know this may scare some of you away (and piss off some others) but I'm sticking to my guns on this. Startups are hard work and if you want it to fly, it's going to take up your every waking moment in one form or another (actual work or thinking about actual work). This is likely to be the hardest thing you'll have to do since you've very likely gotten comfortable in life. There will be many late nights and weekends when you think: what am I doing? Is this worth it? For those of you passionate about this, the answer is, of course, yes, but you'll feel it nonetheless. Key word there: Passionate. You've got to have passion for what it is you're doing or you'll burn out long before you get to where you need to be.
2) Assume you're going to self fund the first year. Maybe longer.
If you've spent the last 20 years working in big companies (as most of you first time wannabe startup guys have) you haven't built the network you'll need to get funding (Angel or VC). It's just that simple. The good news is it takes a lot less to get a startup to the point where you can get outside funding compared to a few years ago (now: $100K-250K vs. several million a few years ago). I know of some people that have done it for a few tens of thousands. The other good news is that having been around for a couple of decades, it's likely you've got some assets to draw on. Now's the time to do it. Form a corporation or LLC, open a bank account and put $X into that account. That's your funding and it will determine your ramp (how long you have until you either start making money or get outside funding). Assume that money's spent and be disciplined about spending it only on your new companies needs. The goal here is to make it last as long as you possibly can. Then, build your team (which is an art requiring an entire post onto itself and I'll write that up in another blog entry in the near future).
3) As soon as you decide you want to do this, start talking to VC's and Angels in your local area.
If you're not in an area with VC's and Angels, consider moving. Seriously. You're new to the game and they're going to want to be close to you. Count on it. Assuming you've got a good idea, and some chops (exec for a fortune 500 company, key person in a smaller company, impressive resume of experience/accomplishments, etc) , all good VC's will find time (30 minutes) to meet in a 'no harm no foul' type meeting. The second way is you very likely know someone who can introduce you to a VC (this is the best way and how I met our lead investor and chairman, Brad). Maybe have a low key lunch. If you like them, stay in touch. That's it. Just stay in touch. Do not ask for money; you're not ready anyway. Ask for advice on your idea and people you might talk to. You need to show you can do something other than dream.
Unless you plan to fully self fund, this really is important. You really need to spend a year or more building up a list of contacts with people that can help you and that you like and who like you. No one's going to fund you cold (unless you've somehow hit the right product out of the gate and built up a real business with revenue and profit already flowing).
Chances are you don't need $3M plus (VC territory). Concentrate on networks of angels (<$1M).
4) Don't do it alone.
This is where I made a real mistake in starting my current company. I did the benevolent dictator model where I funded everything and kept a tight rein of control on everything. We built some kick ass technology and saw some market success, but we didn't really nail the business side. I'm good a certain set of things and I'm weak at another set of things. I made the mistake of thinking I'd learn the stuff I hadn't done before on the fly. The reality is: you won't have time to learn the stuff you need to know when you need to know it. Yea, to a degree you will by fiat, but not enough. Find 1-2 folks you like, respect and want to work with and who compliment your skills. Essential. It's also going to be easier to get funded. Investors like teams that are filled out (at a minimum: a technology person that can make things real and a business person that can put together strategy and develop new business).
5) Don't ask for money to soon, or too late.
You've got an idea that's been put together into a working prototype (in today's tech world where I'm focused, that's a website with at least an active base of 'beta' users-usually 'at least' ). There's a degree of buzz about the area you're focused on. You've been in touch with potential investors for a while. You're running out of your 'I'm comfortable that I can lose this' money, or you really need to expand quickly and just can't bootstrap it. Now's the time to talk to your contacts. Tell them you're at a crossroads which is, usually, go forward and get funding or shut it down. If you've got something real, you've got a team that can actually build and deliver and you've got a market that looks interesting and you've got smart potential investors, ok, cool. Ask them to lunch and give them the pitch. I won't go into the pitch, but the reality is, it's more about you, the team and your tenacity and dedication at this point. That'll show, or it won't. They'll make a decision largely based on that.
On the flip side, don't wait too long. When it's looking real, don't hesitate. Call your folks and set up a meeting and lay it out. If you wait too long (i.e. too many competitors, someone else gets in the door first, etc.) you might miss the chance. As with everything, it's all about timing. And you'll find out pretty quickly if you have what it takes. Or not. Better to shut it down now than dropping another $100K of your own money to keep it going when it's not going to fly.
6) Start with one really good investor who's known as being a really good investor.
Easy to say, hard to do. I was lucky this way. Our lead angel investor, Brad Feld, also happens to be a VC and he's known as a guy who knows how to make bets like this. He's very smart, very likable and we were damned lucky to met him and click with him. Our angel round last year was a flurry of meetings between myself and his network of angels. I think something like 85-90% invested after initial meetings with me. It wasn't really me who sold it... our lead investor being involved sold it. The people you pick to work with are going to make or break your ability to get funding beyond your own bootstrapping. Pick early, pick wisely, and sincerely develop the relationship over time. And don't forget, you've got friends that can invest as well. Maybe not at the level a professional or serial angel investor would, but some. Pull them in too. Every little bit helps. The process for us was about 60 days from go to close. The reason? Our lead investor is a rock star in his field.
7) Getting the money is when the real work starts.
Up to this point you've likely been running your own show. No more. You're now going to have a board of directors and they're going to help you run your company. This is (initially) a big shift but an essential one and something you should prepare for. Your board is going to be made up mostly of your investors and they are a true wealth of wisdom and experience. Use it. And get ready for the ride of your life.
Wednesday, May 02, 2007
And man did he get some great comments! In the second he concludes with:
One of them asked me - do you know any 45 year old entrepreneurs?
Yes I do. But only one of the entrepreneurs in our current portfolio is older than 45. And he'll probably be starting companies until he dies. It's what he does.
But the facts are pretty eye opening. Nine of our eleven entrepreneurs are in their 30s. One is in his 20s, and one is in his 50s.
So I don't have any really good advice for the mid life entrepreneur going through a "what next?" crisis. But one thing I'd say is try to think like that late 20s/early 30s entrepreneur doing it for the first time. Don't let everything you've learned get in the way. Go for it with gusto and don't think too hard.Bravo Fred! I couldn't agree more. The key is keep the sense of 'it's possible' in the forefront of your mind at all times. As you age, and collect the scars of war that day to day business brings, you learn to avoid things. You collect things, assets, family, responsibilities that make taking risk a little more difficult. That can be the death of having an entrepreneurial spirit.
Sometimes, 'fools rush in' is exactly what it's all about. Sometimes, a fool that doesn't know better (or chooses not to know better) is exactly what's needed to create something truly great. To have the balls to think they might be able to change an industry or maybe create a new one. To believe that they might be able to use technology to democratize some capability out to millions of people that was once controlled by only a few.
When a 23 year old Steve Job's creates Apple Computer, mostly because he doesn't know he can't and that the odds are completely against him, and again, an 'in his 40's" Steve Job's takes a has been company slowly on it's way to irrelevance that's had the shit beat out of it by big bad Microsoft and revitalizes it into one of the hippest coolest (and most financially successful) companies in the tech world, it's because he didn't let the world beat that 'it's possible' thing out of him. When he was young he was often described as mercurial, arrogant and haughty. Today... Is he older and wiser? You bet. But he never lost his sense of 'it's possible'... in his case, to change the world. To make a dent in the universe. And yes, he's still mercurial, arrogant and haughty. And for Jobs, maybe that's just what it takes for him to keep at it, to believe that it's possible.