Brent Simmons

By Mike / On / In Personal

One of the most important lessons from my apprenticeship did not come from my mentor, but from my fellow apprentice, who talked me into coming out of my shell and meeting the community of Seattle Xcoders. I met a lot of important people, not the least of whom was software legend Brent Simmons.

This would soon become vital, when things started to get tense between my mentor and me. Brent told me stories of his own apprenticeship, and the tension that grew between him and his mentor. He explained it as an inevitable phase, indicative of growth, a sign it was time to move on.

We often call him the godfather of indie software development, but in truth he more closely embodies the Japanese word, “sensei,” which is translated as both “teacher” and “doctor,” but literally means “born before.”

Just as your doctor is able to give peace of mind by assuring you what you’re experiencing is normal, just as a teacher is able to draw from their superior knowledge and experience, so too has Brent set the tone and led the way for a generation of App Makers.

I can honestly say I would not be where I am today if it weren’t for Brent Simmons, and I think several other people would say the same thing. On the occasion of his birthday—it’s hard to believe it’s been 5 years since B4[0]—I thought I would share some things I’ve learned reflecting on Brent Simmons.

The first time in my life I ever missed a flight was to Las Vegas, for Brent’s big 40th birthday bash. I mixed up a.m. and p.m., which is very much unlike me, the former airline employee. I was flying back and forth between Seattle and San Jose because I’d just come on as co-founder of Tapulous.

I have always prided myself on an attention to detail and a willingness to push myself. Here, without even trying, Brent gave me a permanent reminder that pushing yourself too hard will lead you to make mistakes.

Brent is a hardcore dude, but he knows when enough is enough. Since his 40th, he’s lost a lot of weight and gotten into really good shape. It’s no secret nerds in our community have been getting in shape lately, and while some of that is attributable to Steve’s early demise, I think it precedes that.

I know for me, seeing Brent get into shape was a real kick in the pants. If he’s not immortal, nor immune to the laws of nature, who the hell are we?

I’ve noticed something else about Brent. He’ll disappear. He’ll decide he’s had enough, and would like to get some sleep, and will just disappear. If you happen to be standing next to him, he might say goodbye, but otherwise, he’ll just be gone.

I, on the other hand, always make the rounds and say goodbye to people. I stress about other people’s feelings. A lot. Brent doesn’t, and yet we all love him. I think there’s a lesson in that. Something about being genuine and useful and spending your energy on things that matter.

You can draw boundaries, and take care of yourself, and people will still respect you. That is what I learned from Brent Simmons.


By Mike / On / In Personal

I’m a very lucky man, and one of the things that makes me so lucky are my friends. These are the nicest, most talented people I’ve met in my life, and many of them have skills that have made them vital contributors to my success over the years—not only in making my products and building my brands, but in getting my message out there (for what it’s worth). For example, a bunch of them have started great podcasts with unbelievable guest lists, which they have generously allowed me to be part of.

My friend Saul Mora has assembled one of the finest collections of interviews in our industry with his NSBrief podcast. Seriously, look at his archive—it’s like a who’s who of NSCoders, and he’s had me on not once, but twice.

What’s cool about NSBrief is that the audience is just as illustrious as the guest list. Both times I’ve been on the show, I’ve ended up getting amazing, life-changing feedback from its audience. Most recently, I talked about trying to blend consulting with making our own apps, and ended up basically having the implementation details of that handed to me after the show.

Short version: we’re setting thresholds for when our consulting flag goes up or down. If we drop below 3 months burn, we have to accept consulting until we get back up to 12 months burn. Since we don’t have capacity for business development, we’re doing all our contracting through Big Nerd Ranch Europe. (So if you’d like to hire us, contact Marcel and Bolot!)

My friend Dave Wiskus and I were recently able to celebrate our strange relationship on his show, Unprofessional. Because Dave is the protege of my protege, I am always busting his balls. He wanted to do a show themed around being offensive, so I spent the whole show pretending to hate the show (which I actually love) and ripping on Dave (who I actually love).

It’s a beautiful piece of performance art. At one point I even insulted Dave while the call was muted, an act so dickish it calls to mind the old Dutch expression, to wipe one’s ass on the door. I had a really good time. Given how successful the show has been, it should come as no surprise that Dave (and everybody’s best friend, Lex Friedman) are not only genuinely great people, but incredibly good sports.

Finally, although the episode is not up yet, I had the great pleasure of being interviewed by my old pal Guy English and Rene Ritchie on their show, Debug. I was so excited when they started this show, because of Guy’s skill as a conversationalist. Really, of all the many things to envy him for, that’s the one I envy the most.

Maybe it’s my internal journalism major, but I always pay attention to people’s interview styles. Saul sets up the guests and lets them talk. Dave and Lex relate to their guests by sharing their own anecdotes. Guy and Rene ask probing follow-up questions to encourage their guests to dive deep in exploring their topics.

I know the key to great conversations is asking great follow-up questions, but that’s easier said that done. I’ve always admired Guy for this, and I listen to their show as much for the interviews as for a case study on how to talk to people.

That’s what makes me respect my friends so damned much—they have so much to teach me, just by doing the things I can’t.