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Ann is the co-founder of Hummer Winblad Venture Partners which opened its doors in 1989. It was the first VC firm to focus exclusively on software. Since that time, 45 of its portfolio companies have been acquired or gone public. She began her career as a systems programmer at the Federal Reserve Bank. In 1976 Ann co-founded Open Systems, Inc., a top selling accounting software company, with a $500 investment. She operated Open Systems profitably for six years and then sold it for over $15 million.

$15 million in 1982 dollars is worth approximately $50 million today using GPD per capita measure, which is the appropriate metric for this kind of thing.

From page 299 of Founders at Work: Stories of Startups' Early Days:

When I went there, it was the first real business experience I had — although I had had part time jobs. I'd never been in a corporation, and it felt so glamorous to have a cubicle. Minneapolis is a bright city. There's the Nicollet Mall and you were right downtown in the city. It's like getting a job in San Francisco.

But it just wasn't inspiring. No one was chomping at the bit. I actually can't remember — I knew I was going to quit, but I can't remember the moment where I thought, "I'll quit and start a company." I still felt very empowered, like, "This isn't this hard a job. This is a big job and I've already gotten promoted once in the first 3 months and I know I can earn money. I can always come back to this, so why don't I break out?" So the three guys from the Federal Reserve that started the company with me — one guy did quit his job and the other two took a year sabbatical, just in case this didn't work. They held on to the safety ring.

There were not a bunch of people saying, "Start a company, start a company. Let's do this. Let's build something from scratch." It's so long ago now that I just remember the general feeling that there was very little to risk. I was somehow already fully trained for anything that might confront me. Of course, all that is false; there's a lot of risk and you are never fully equipped to… you just have to be very adaptable. It turned out that I was adaptable. I didn't know that until I did that, but it was just a feeling of fearlessness. "What's the risk? What will I have to lose? I'm sure I can do this." It was not cockiness, just that moment you feel in your youthfulness that you are sort of empowered to achieve.

I think what does separate some entrepreneurs from other entrepreneurs is we're not handwringers. We don't worry about the unknown. We don't really worry about the risk points ahead. As you get older and you get more experience, you train yourself to think ahead about the risk points versus just to take the next hill. But non-risk-takers and non-entrepreneurs would have really big headaches about this. They would need some level of comfort and safety.

That's something that we look for in entrepreneurs — that they have the courage to do the job. That they'll have the ability to judge the business situation. They'll have the ability to lead people. They'll have the ability to interact with the marketplace and to really build confidence into strategy.

I've been doing a lot of reading lately, and today I was reading "Hiring is obsolete" by Paul Graham. I loved it, and the section on risk really stood out to me, and I'd like to highlight some specific bits.

So what you should invest in depends on how soon you need the money. If you're young, you should take the riskiest investments you can find.

All this talk about investing may seem very theoretical. Most undergrads probably have more debts than assets. They may feel they have nothing to invest. But that's not true: they have their time to invest, and the same rule about risk applies there. Your early twenties are exactly the time to take insane career risks.

The reason risk is always proportionate to reward is that market forces make it so. People will pay extra for stability. So if you choose stability– by buying bonds, or by going to work for a big company– it's going to cost you.

Riskier career moves pay better on average, because there is less demand for them. Extreme choices like starting a startup are so frightening that most people won't even try. So you don't end up having as much competition as you might expect, considering the prizes at stake.

…

But it's not necessarily a mistake to try something that has a 90% chance of failing, if you can afford the risk. Failing at 40, when you have a family to support, could be serious. But if you fail at 22, so what? If you try to start a startup right out of college and it tanks, you'll end up at 23 broke and a lot smarter. Which, if you think about it, is roughly what you hope to get from a graduate program.

Even if your startup does tank, you won't harm your prospects with employers. To make sure I asked some friends who work for big companies. I asked managers at Yahoo, Google, Amazon, Cisco and Microsoft how they'd feel about two candidates, both 24, with equal ability, one who'd tried to start a startup that tanked, and another who'd spent the two years since college working as a developer at a big company. Every one responded that they'd prefer the guy who'd tried to start his own company. Zod Nazem, who's in charge of engineering at Yahoo, said:

I actually put more value on the guy with the failed startup. And you can quote me!

So there you have it. Want to get hired by Yahoo? Start your own company.

The entire essay is absolutely worth reading for anyone interested in starting their own business.

Back in January of 2007, I wrote a list of 52 things that I want to do before I die. To this day, it stands out as one of the most vividly-remembered things I've ever written. Turns out that writing a list of your life goals is actually pretty useful. It's sort of like writing a business plan for your life, and you might discover some things about yourself that you didn't know along the way.

[ All lists ]

1. Fall in love and get married
2. Stay married
3. Have a son
4. Have a daughter
5. See them both become self-actualized, successful people at whatever they choose to do
6. Meet my grandchildren
7. Never stop moving towards self-actualization and always make forward progress in self-improvement
8. Own my own business
9. Start my own financially-successful website
10. Be out of debt by age 29
11. Have a net worth in excess of $1 million by age 30
12. Have a net worth in excess of $50 million by age 35
13. Have a net worth in excess of $1 billion by age 50
14. Be on the cover of a prominent business or news magazine
15. Write a book
16. Go to South Africa
17. Visit Egypt and the pyramids with Fabien
18. Own a collection of fine watches. (God I love watches!)
19. Go to a professional driving school
20. Drive an open-wheel (Indy) car
21. Design my own home and have it built for me.
22. Own a new Ferrari
23. Order and pick up a brand-new Porsche 911 Turbo in Europe
24. Participate in a Porsche event on two seperate continents
25. Buy a Dodge Viper for Rich. Just to say "Thank-you."
26. Visit Australia, Fiji, and New Zealand with my dad
27. Visit Antarctica
28. Visit Iceland
29. Visit Norway
30. Go on an African safari (non-hunting)
31. Get my SCUBA license in Guam and go diving with Nick there
32. Dive the Great Barrier Reef also with Nick
33. Go to China and see the Great Wall
34. Throw a huge birthday party for myself when I'm old since I've only had one in my life.
35. Get rid of the bittersweet feeling that the holidays brings by having my own family where we stay home and celebrate and people come to us, rather than having to figure out where I'm going on what day. Be the center rather than participate in other people's centers.
36. Own a beautiful home somewhere in New Hampshire
37. Contribute something meaningful to a great charity or organization
38. Take my grandmother to a Red Sox-Yankees game
39. Take my grandmother to a Red Sox World Series Game
40. Go to the summer Olympics in another country
41. Do something truly extravagant with my close friends, just for the hell of it.
42. Create a full college scholarship to a worthy institution based on need and merit that can only be won by a white male.*
43. See a Josh Groban-Charlotte Church duet. Live. Somewhere in the first five rows.
44. Start a news-media company
45. Start an angel/venture capital fund for startups
46. Retire and run my own (or someone else's) charity.
47. Have a library in my home.

* There are many scholarships for women and minorities. At this point in time, however, boys are the minority in college. Society may have forgotten about them, but I have not.

Ben Franklin is one of my all-time favorite historical figures; there are few people who have been universally successful in all they've done: business, politics, science, and humanitarianism. Franklin was one of these, and he's left a guidebook for those who wish to follow in his footsteps. (And really, how can you beat $2.50 for a brand-new book?)

I've been reading through it lately, and while it's easy reading, it's so chock-full of wisdom that I find it slow going. Lunchtimes and evenings find me with pencil in hand, underlining and annotating the bits that especially speak to me, and there are many.

I came across this paragraph, and I was astonished. With the anti-vaccination crazies gaining influence and mindshare, this earthy bit of common sense was a breath of fresh air, written in the 1700s by someone who knew a world without vaccines, and saw the devastation caused by these diseases — smallpox, polio, and many others — first-hand.

In 1736, I lost one of my sons, a fine boy of four years old, by smallpox, taken in the common way. I long regretted him bitterly and still regret that I had not given it to him by inoculation. This I mention for the sake of parents who omit that operation on the supposition that they should never forgive themselves if a child died under it, my example showing that the regret may be the same either way, and therefore that the safer should be chosen.

Simple and profound. Alas, I don't think the anti-vaccination types will take his advice to heart, and we are all the poorer for it.

While going through my RSS reader this morning, I came across one of JD's daily links posts, and one of them was to A History of Debt in America. It's quite a long article, but well worth reading. Unfortunately for people like me, reading large quantities of text on a screen gets to be painful after a few minutes.

I whipped up a quick PDF of all of the pages, and Tom, the author of the article, has graciously allowed me to post it here.

It's 21 pages long, and will take you a little while to read it, but it's worth the time.

PDF link.

If you enjoyed this, you may enjoy my post on how paying off debt is like folding laundry — a behavioral, as opposed to mathematical approach to paying off debt.