Jonathan Siegel is a buddy of mine who lives in Tokyo. I can’t decide whether I’m more floored by the fact that he runs five businesses at once or has eight kids. He recently wrote a book The San Francisco Fallacy, mostly to share his experience with running software businesses for the last two decades with folks who might be getting a wee bit too much of their advice from Techcrunch.

I think this makes an interesting companion interview to the last one we did (~6 months ago) with Thomas Smale, who runs the firm which helped me sell both of my businesses. Jonathan is an operator but he’s also a buyer of businesses, as opposed to me (an operator who recently sold businesses) or Thomas (a broker of them).

[Patrick notes: As always, the below transcript occasionally has my thoughts inserted in this format.]

What you’ll learn in this podcast:

• Why folks with successful businesses sometimes sell them (and how this creates opportunity for buyers)
• Why to make good decisions as a businessperson so that you can make “bad” decisions as a coder/artist/etc
• How to run five businesses at once (spoiler: put people in charge of the day-to-day work)
• How two entrepreneurs have found their goals changing over the course of their careers

Running A Business Portfolio with Jonathan Siegel

Patrick McKenzie: Hideho everybody. My name is Patrick McKenzie, better known as patio11 on the Internets, and I’m here today in Tokyo with my friend, Jonathan Siegel, who also lives in Tokyo. Jonathan is a multi-time entrepreneur, but I’ll let him give his self-introduction.

Jonathan Siegel: Thank you, Patrick. It’s a pleasure to be here. I’d say my background is easiest to understand if you really think about me as a techie. I grew up loving anything that had a battery or I could plug it in the wall. I took apart everything, tried to put it all back together, and it rarely worked. I remember when I was 12, got my first computer. It was a 286 12 MHz. Took it apart, put it back together, and it actually worked.

That’s back when you had the big cards in the computer with the hundred little ICs on the green silicon chips. Then after that, I got fascinated, and just did everything else that I possibly could on top of the computer. Ultimately, I learned how to do some software, and then went to school and did more software.

Ever since then I’ve been tinkering around, for fun, on the computer and I’ve been rewarded with tons of opportunity from that, business and otherwise.

Patrick: Yeah, I remember, I think I met you originally because at the time you owned, Earth Class Mail, which is a mail forwarding service that I’ve used to have a virtual mailbox in the United States for sending stuff to Japan for the last couple years. But it turns out –...

For the full transcript see here.