I’m not sure how old I was, somewhere around 8 I’d guess, when I noticed that the wire from the wall outlet to the toaster was actually two separate wires.

This didn’t make sense to me. The power came out from the wall socket and flowed into the toaster. Why have two wires? I wanted an explanation.

This marked the start of a long period of my parents — principally my dad — being challenged by my questions. He took me to the stores that had the electronics supplies I wanted, and spent money he probably didn’t have to support my projects.

By the time I was about 12, my dad took me to sales of surplus equipment that was available only to people connected to the schools, as he was. It was all sold by the pound!

I got all sorts of equipment, generally non-functional at least in my hands, which I disassembled into its parts. I still have some of those parts.

The Lone Repairman

I remember taking our TV to a local repair shop, which was in fact the garage behind someone’s house. To me, his TV repair shop looked the ideal workplace.

I said something like that to my father, and he responded unusually sharply, that I can be much more than that, a degreed engineer with a job in a big company.

My passion for all things electronic drove me all through my teenage years, and then to UC Berkeley, where I got my BSEE in 1977. My preference remained for running my own small companies. My father’s ambitions for me helped ensure that I got a degree, but ultimately being in a big company was not where I wanted to be.

From Analog to Digital

By the time I was in college, the hot topic was not television but computers. This turned out to suit me well, because I was tired of spending years learning advanced math so I could apply it to analog electronics. The true and false, one and zero, and AND and OR of digital electronics made perfect sense to me.

I never did really come to understand how radios and TVs worked. At Berkeley, those were subjects too practical for discussion at the university.

Into the Working World

My first job out of college was working for Hewlett-Packard, back when it was all one company. I helped design a training computer for technicians and wrote the self-instructional manual that went with it.

Within a couple of years, however, I had consulting clients on the side, and that itch — part entrepreneurial, part independent — led me to leave HP after three years.

My insatiable curiosity, desire to be independent, and fascination with making things have continued to shape my life.

It was 1980 when I left HP, and the 35+ years after that will have to wait for future articles.

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This year, I’ve done a full reset, keeping most of the old content as an archive, and starting fresh with a new concept for the website I want to build.

The rethinking was driven by a major change in my life.

Last fall, I was diagnosed with intestinal cancer, and dealing with that has been my focus since.

Treatments are been going well, though not, of course, without ups and downs. I’ve been writing about the personal details on my private blog.

Because of my illness, I have dramatically cut back on my work hours. With lots of time on my hands but relatively little energy for physical activity, I am now focused on writing. Getting sick does have a silver lining, odd as that may seem.

I have a lot of things I want to say that have been running around in my head for many years. You’ll start seeing them here shortly.

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We’ve enjoyed the property immensely, having raised two kids and built three businesses here. But it’s now much more space than we need, and the wonderful grounds are demanding.

Now that my office is in downtown Sebastopol, and Amanda is at Analy High School, it’s come to seem very enticing to move to a smaller house in town. I know we’re going to miss our gardens and woods and total privacy, but after more than 20 years we’re ready for a new adventure.

We’ve been cleaning up, packing away non-essentials, and fixing all those nagging little things you never get to, for the past 6 months, and the house and gardens are in their best shape ever. It makes it that much harder to leave!

We hope to be settled in a new house in Sebastopol in the fall. Just in case you know of anyone who is thinking of selling, we’re looking for a 3-bedroom house, within walking distance of downtown Sebastopol, in a reasonably quiet location.

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What has made it most challenging is that I’m up to my eyeballs in running Webvanta, the startup I cofounded with Christopher Haupt. Startups are always all-consuming, and the current economic climate has made it even more so because of the difficulty of raising capital.

We have managed to raise a modest amount of capital, but it’s been very time consuming, and it’s not enough for us to get out of bootstrapping mode. So my time is split between ongoing fundraising, growing the business, and doing contract work as part of our bootstrapping process. It’s fun, but exhausting.

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Kestrel II in Ayala Cove

Two weeks ago I closed the sale of Kestrel II, a 30-foot Sea Ray cruiser built in 1979. I owned her for 9 years, and spent many happy days and nights aboard.

Some of the most memorable times were trips out the Farallon Islands; trying to keep up with the Queen Mary II as she came in the Golden Gate; a week in the Sacramento Delta with my family; several lovely evenings at Paradise Cove with my wife; many 4th of July fireworks shows; Fleet Week; Tall ship visits; and countless visits to Angel Island’s Ayala Cove.

Seals in Richardson Bay

Watching the flocks of pelicans and other birds was always a joy. Once we saw a whale off San Rafael. And there were many times we enjoyed the seals and sea lions on the buoys and floats around the bay, as well as their heads popping out of the water.

Deer in Ayala Cove, with Kestrel II in the background.

I took many thousands of photos from this boat, some of which you can see on my boating site, BoatingSF. I’m a sailor at heart, but one of the things I love about power boats is that they make much better sightseeing and photography platforms, at least within the context of San Francisco Bay.

Sunset at our Sausalito slip

There’s an old saying that the happiest day in a boat-owner’s life is the day he buys the boat, and the day he sells it. That may be true for many, but it wasn’t for me—I was sad to part with Kestrel II. I gave her up because owning a boat was just too expensive and too time-consuming a hobby while living on savings and building a new business.

Another factor was the unconscionable rate at which the boat guzzled gasoline. Not only was it awfully expensive at today’s gas prices, it started to feel irresponsible in these days of global warming.

The Irrational Love of Boats

I love boats. I can’t quite explain why. It has something to do with the freedom they offer, and the different view of the world they provide.

Tall Ship Pallada Visiting San Francisco

Many guests remarked how utterly different San Francisco seemed when viewed from the water. I often reflected on how much the water was an integral part of San Francisco’s life for centuries, yet it has become almost peripheral to most residents and visitors today.

Being on a boat puts you back in touch with the realities of San Francisco Bay, in a form that is largely unchanged (despite huge changes in the shoreline) since its settlement.

Boats do consume ungodly amounts of time and money. A complex mechanical contraption, bathed in salt water and salt air and constantly jiggled around, is a formula for endless repairs. For a long time, I enjoyed the never-ending projects, but I’m ready for a break. And it’s a much lower-stress undertaking when money is plentiful than when it’s tight.

Sunset at the Golden Gate

I replaced nearly all the guts of this boat, bit by bit, even including the engines. Replacing the engines cost as much as a nice car—and more than I sold the entire boat for. One of the troubling things about boats is that most of the money you put in to them you can never get out.

Yet there is something just wonderful about boats. They can be things of beauty (though this boat wasn’t), retreats, projects, and traveling machines. The variety of them is endless, and it’s fascinating all the different tradeoffs made by various designers and owners.

The stunning Lynx

If you want to see just how far a boating passion can be taken, pick up a copy of Mine’s Bigger, the story of Tom Perkins’s creation of the Maltese Falcon, the world’s largest private sailboat.

What’s Next?

For a while, I’ll enjoy my kayaks and the occasional rented boat. But there will, I’m sure, be another boat in my future. Maybe a catamaran based in the Caribbean, if my current startup is as successful as I hope it will be…

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I’m as busy as I’ve ever been, and my income in the past year is the lowest it has been in more than 25 years. But I’m having a great time, and I have a good feeling about where things are headed. I thought I’d take the excuse of this one-year anniversary to look back on my decision to leave Adobe, and catch my readers up on my business thinking.

Looking back on Adobe

I’ve not written much about my experiences at Adobe, in part because I want to avoid any possible appearance of breaking confidentiality agreements, and also because I wanted to gain some perspective first.

Looking back on my five years at Adobe, there’s a lot that I’m grateful for. I learned a tremendous amount about digital imaging and the PC software business, and about life inside a big company. I met a lot of great people, was able to immerse myself in digital photography, and had the opportunity to lead a research team and do technology licensing with the power of a big player behind me. The team I helped build for Fotiva continues on, in large part, as Adobe’s Santa Rosa office, and I’m pleased to have had some small role in growing the software business in the North Bay. And the product that started life at Fotiva has an enduring role as the organizer in Photoshop Elements.

In a strange way, though, I’m most grateful to Adobe for being so thoroughly dysfunctional when it comes to enabling innovation that it drove me out. As someone with a entrepreneurial heart, I found Adobe stifling. If I had been able to accomplish a bit more at Adobe, I might still be there, and then I would have missed out on so much.

To a large degree, the challenges I faced finding happiness at Adobe would be there in any businesses at that scale. But not entirely. Many of the other entrepreneurial folks I met at Adobe, who tried valiantly to build new products and services, have also left. They’re at an assortment of small companies, but also at Google, and Yahoo, and Apple.

One of Adobe’s biggest weaknesses, in my view, is the distance between top management and the people who have passion for innovative new product ideas. It is exhausting, and usually dispiriting in the end, pushing ideas up through a chain that, at it’s pinnacle, doesn’t seem very interested.

The difficulties I had getting new concepts to market at Adobe, especially when they were web-related, are symptomatic of top management’s resistance to exploring new concepts in the marketplace. Adobe doesn’t like to accept the risk of new markets in return for a role (and learning opportunity) as an early player. Perhaps at Adobe’s scale their approach of waiting until market opportunities are clear, and then buying their way in as needed, makes sense. But it did not make for a satisfying place for me to work.

My evolving Ruby on Rails business plan

When I left Adobe, I had done a little Rails development, and read a lot about it, and I felt strongly that it was going to be a big deal. I spent the majority of this year building custom Rails sites for small businesses, and set up Topaz Web Solutions LLC as the home for that work. I enjoyed it, and some of it is ongoing, but my focus has now shifted to Collective Knowledge Works, Inc., the company I cofounded this fall with my partner Christopher Haupt.

I spent quite a while looking for ways to build a business around delivering Rails-based solutions to other small businesses. I continue to believe there is a great opportunity in this domain, but the sales and support challenges are significant.

Collective Knowledge Works grew out of an idea I had to create a portal for Ruby on Rails developers. We’re now deep into doing just that: you can sign up for the beta list at BuildingWebApps.com. Within a couple weeks, we’ll be letting in beta testers, and early next year it will be public. I can’t wait to show it off, and I think it’s going to be a great resource for the Rails community. After eight years away from the editorial, publishing, and training business, I’m glad to be back in it.

Initially, we don’t expect BuildingWebApps.com to generate much revenue directly. Our first revenue stream will be from the Ruby on Rails QuickStart Seminar that we’ll be presenting in February in San Francisco. Later, we believe we can create revenue from the site itself in various ways.

Christopher and I have just launched the Learning Rails podcast, which has been an adventure of its own.

There’s a bigger plan in the background, too. All the technology we’re building for BuildingWebApps.com can be used for any knowledge domain. After we’ve had time to build out this first site, we’re going to develop additional knowledge domains, and enable others to host their own knowledge domains. That’s why we named the company Collective Knowledge Works.

It’s great to be back in this early business-building phase. And it’s wonderful not to have to try to sell new ideas up through multiple layers of management, but simply to decide what to do, and then do it.

The post Celebrating a Year of Freedom appeared first on Parting Thoughts.

This blog will focus on my major business activity: developing custom and semi-custom web sites for service businesses using the Ruby on Rails framework. I’ll have another blog, to be announced shortly, for nitty-gritty technical topics; this one will focus on how the web can deliver much more value for small and medium businesses.

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When I left Adobe at the end of November, I promised myself that I would “take a break” for perhaps as long as three months, and certainly through December. So for the first time in decades, I’ve had a little while without a job, and not actively building a business.

I had a great job at Adobe. There were a lot of exceptional people I had the pleasure of working with. I’ll miss working with many of them, but I’m sure the relationships will endure. I’ll miss being in the digital photography industry, though I think I’ll enjoy it even more as a hobby.

I won’t miss the shrink-wrapped software business model, the isolation from strategic decision making, the split between marketing and development silos, the financial tyranny of being in a public company, and, most of all, the too-small box I felt I was in.

Seven years ago (on Thanksgiving day, in fact) I had the idea for a photo appliance, and registered the PhotoTablet domain. A couple months later we raised a round of financing and started a company, which evolved to be a PC software company and was renamed Fotiva. Two years later we sold the company to Adobe, where I’ve been for five years.

I’m starting on my fourth career. First I was a hardware/firmware engineer; then a newsletter publisher and conference producer; then a manager of software development and research. Now it’s on to building a business based on web applications. I think it’s a bigger opportunity than anything I’ve done in the past.

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