Living Like a Rich Teenager - Part 2 - The Longboard

This is part 2 of my “Living Like a Rich Teenager” series. In short, if you have no responsibilities, then why behave like a responsible adult? Instead, do stupid stuff and spend your life goofing off! For the longer version, see Part 1 - The Kayak.

If I’m known for one thing these days, it’s my skateboard videos. You’ve probably seen me flying through the air in slo-mo followed by a slowed down impact-and-grunt several times at this point. People watch this, cringe, and then say, “What the f… are you thinking?”

Here I will explain the what and why of my new hobby, but first, since this is tumblr, enjoy an animated gif…


The Board

My board is a Rayne Hellcat with Abec11 Freeride Classic wheels, plus a bunch of stuff that I know nothing about (trucks, bushings, etc.). It’s definitely a longboard, with no kicktail for jumping or any of that nonsense.


The Cost

My board was a gift from my wife for Christmas of 2013, and she bought it from a longboard enthusiast coworker for $150. After looking online, I’m pretty sure that was a bargain.

However, like the kayak, I’ve already spent much more than that in gear. Helmet and slide gloves ran me about $120, then I bought a full-face helmet for $70. Elbow and knee pads were graciously donated by Melinda Weathers. Padded shorts were another $70. Finally, there’s an almost weekly supply of $20 cargo shorts from Target. They get shredded after a few aborted slides.

All told, the hobby has probably cost me around $500 at this point, or about 1/2 the up-front cost of the kayak. If you want to go cheap, you can skip the pads and helmet, but you’ll definitely regret it. You will get your use out of the protective gear, likely on day 1 when you fall on your face just stepping onto the board.

The Pros

The number one pro is just how cool skateboarding is. All the cool kids did it when I was younger, but I was too busy reading fantasy novels, playing D&D, and being nerdy. Now all the cool kids are taking care of kids of their own and otherwise behaving in a totally non-cool manner, while I’m out there shredding. Oh how the tables have turned!

Besides being badass, It’s also actually fun. That may be hard to imagine when you’re watching me sliding across the pavement in slo-mo, but riding the board and pulling off a good slide is really exciting. When I finally started succeeding at the slides, I pendy’ed my way down an entire hill to the dead end at the bottom. It’s hard to explain how fun that was and the sense of accomplishment I felt at the bottom. Plus, having other skaters there to congratulate me was pretty great, too.

The videos have been an unexpected pro as well. I like being in the limelight, and it turns out that a lot of people enjoy my slide videos. I’ve learned that when I release one, especially one with some brutality, it’s enough to stop work in departments at both Vitrue/Oracle and Turner Broadcasting. In the picture below, daily scrum is put on hold so everyone can watch me wipe out attempting a standup heelside 180. The crash was brutal, but being famous is nice.


The Cons

As cool as it is, it’s actually much harder than people realize. I’ll be riding down the street and kids on the sidewalk call out, “Do a trick!” They don’t realize that just riding the damn thing and not wrecking is a trick!

The level of practice and skill required to just look proficient is pretty high. I’ve spent months learning the basic slides, and I’ve lost quite a bit of skin doing it. Plus, by most measurements, I still suck. By contrast, most people can learn to ride a bike in an afternoon and their skill grows very quickly at that point.

I had also hoped to be able to ride it around for short range transportation, but that’s no good. The effort required is high, and going uphill is basically impossible. A bicycle will always be faster, easier, and better than a skateboard for transportation. ALWAYS!

Finally, the worst part is how lonely I get. None of my friends do it, and the people I’ve met online are all on the north side of Atlanta. I’d have to drive for an hour to meet them and skate. So instead, I go alone to a few hills nearby and shred solo. It’s still fun, but it would be way more fun with some friends.

Overall Grade: B+

The loneliness is what brings this down from an A. If I had friends nearby that I could skate with, it would be a lot more fun. As it is, I just have to record the videos and post them for everyone’s enjoyment.

The constant falls and injuries kind of suck, but you’ll hurt yourself less as you get better, and seeing noticeable improvement is very nice.

Click below for a video of one of my better slides (at 2:40)…

Next Time: Singing Lessons

I’ve always wanted to be a better singer, I (or Sarah, in fact) signed myself up for singing lessons. In the next installment of Rich Teenager Life, I’ll explain the what and why.


Living Like a Rich Teenager - Part 1 - The Kayak

Early in 2014, I had a realization: I have no kids, a great job where I set my own hours, no big debts, nobody depending on me, and just generally very little responsibility. I decided it was time to stop acting like an adult, and instead act like someone with no responsibilities. In other words, I was going to live like a spoiled rich teenager. To the best of my abilities, I’ve been living that life for six months now.

To celebrate my new dedication to being gnarly and radical, I selected 3 new hobbies: Kayaking, skateboarding, and singing. Yes, it turns out that as a rich teenager, I’m still pretty boring. No drugs, no late night raves, no carousing…just good, wholesome, slightly dangerous fun. Today I take a closer look at kayaking, something every rich teenager should be doing.

The Kayak

In true entrepreneur form, I sold my “startup” (DoLeaf) and bought “a boat.” Unlike the traditional Silicon Valley story, I didn’t make a bazillion dollars and my yacht is actually a beat-up used kayak that has since been described as, “Huh…I haven’t seen one of those since the mid-90s…” She’s a beater, but I’m in love.


The Cost

Altogether, the kayak and gear (skirt, helmet, PFD, paddle, etc.) set me back around $850, plus the car roof rails and rack was another $600. In teenage dollars, that’s like a billion, I think.

After the initial cost, I realized something about being a rich teenager: A lot of activities have a high up-front cost, but then the cost drops to zero. Taking the kayak out on the river basically costs gas to get there plus lunch once we’re done.

The Pros

I’ve always wanted to go whitewater kayaking, ever since seeing the guys on the Ocoee River just sitting in the middle of the rapids. They could completely master the river currents and go in any direction they wanted. The best comparison I can imagine is a river otter. The water is just a playground for them.

Actually running real rapids is quite hard and still above my skill, but even simple rivers like the Chatahoochie are fun, if even just for the chance to float on the water and enjoy the outdoors.

As a bonus, I quickly learned how to roll the kayak, and that’s a real thrill. Being underwater and strapped in is a panic-inducing experience. Learning not to panic and enjoy the excitement and danger is pretty awesome. And with the help of friends, you get some sweet photos like the one above.

Speaking of friends, that’s another big plus. My wife also bought a kayak at the same time, and while she’s not as excited about whitewater as me, she’s getting better and enjoys just floating along. We also go with friends who rent sit-atop kayaks. It’s hard to beat floating down the river on a Saturday with friends. And, like I mentioned above, it’s dirt-cheap, too, once you own the equipment.

The Cons

The main drawback is the difficulty in getting to good spots. Running the Chatahoochie is a 30 minute drive, but everyone tells us we need to be going to the Nantahala. That’s a 2.5 hour drive and means we’d have to spend the whole time driving, or get a place to stay and make it a multi-day trip. That actually sounds like a fun weekend, but so far I’ve let regular life get in the way. I probably need to redouble my resolve to being a teenager and just do it.

Overall Grade: A

Of all my new hobbies, I think kayaking is probably the best in terms of ease of learning, enjoyment, and overall coolness. It’s fun to do, impressive, and you can bring along friends.

If you like being in the water, and you live within an hour of any halfway-decent whitewater, I’d highly recommend getting a full-day kayak lesson. You may find that you’re a kayaker and just didn’t know it!

Up Next: The Skateboard

If I’m known for anything these days, it’s my skate videos. In Part 2 of Living Like a Rich Teenager, I’ll give the skinny on the longboard. It’ll be rad, so get stoked and stay tuned!


Don’t Hide the Date!

It infuriates me when blog posts get clever about hiding the date, especially technical blogs. I don’t care how awesome the aesthetics are. If you’re not showing the full date you’re doing me a huge disservice!

Ruby on Rails has been out since 2005, and has a well-deserved reputation for changing all the rules every couple years. In addition, the majority of the real documentation is contained in the 1000s of blog posts that have been written explaining things from routing to exception handling to testing to whatever.

Putting it all together, you have nearly a decade of history, a rapidly changing technology, and a distributed (and rarely updated) documentation ecosystem. For someone landing on any given blog post, there’s a huge chance that it’s outdated and useless, or worse, irritatingly misleading.

Therefore, the most important piece of information to examine when first landing on a technical blog post is: When was it written? In the Rails world, if it’s over 2 years old, move on immediately, and even if it’s only 1 year old, you’re still in the danger zone. Before you spend your time reading and analyzing the material, you need to know if it’s worth it.

If your design is terribly clever and only shows the day or month or whatever phase the moon was in when you published it, you’re hiding that incredibly important information. Please do your readers a service and give us all the pertinent info!


Baked Wings Blind Taste Test: Does Thawing Matter?

Last night we executed a blind taste test on baked chicken wings. In the name of science, I’m here to document the results.


To determine if thawing the wings had any effect on the taste. Since taste is hard to really define scientifically, the real goal was for each person to subjectively decide which was better. Our hypothesis (more like a hope) was that we wouldn’t be able to tell a difference and therefore there’s no need to go to the extra trouble of pre-thawing.


  1. Traditional (fridge/counter) thawed wings
  2. Microwave thawed wings
  3. Unthawed, frozen wings

We cooked the 3 different groups of wings, then 4 of us left the room. Erin, our test executor, took the 3 sets of wings and distributed them onto 6 plates, labeled A-F, and created a master sheet matching the A-F plates to their original groups. So, there were 2 plates of each type of wing and only Erin knew which were which.

Aside: Poor Controls

To be fair, there were at least 2 variables that I poorly controlled: spice mixture and oven location. In the interest of staving off criticism of this study, I’ll address both here.

Spice Mixture

The spicing of the wings was a mixture of olive oil, chili powder, and garlic salt. I did not prepare the mixture using exact measurements, instead dumping in the ingredients into a bowl and just adding more as I saw fit. So, the spice variability in the different wings was significant. This had a significant effect on the testing outcome.

Oven Location

I’m not sure, but the location in the oven could have had an effect. One tray was on top, one on the bottom. However, it’s a convection oven which is supposed to circulate the air, so hopefully that helped address this variable.

Each of the participants (there were 4 of us) eats a wing off each plate, then scores it. We were lax here, letting each person define scoring as they wanted. I did it on a good/better/best scale.

Finally, we each announce our scores and Erin told us which plates had which wings.


There was no consensus that any particular plate of wings was better or worse than another. Although each participant had favorites, there was no correlation across the entire group.

Only one participant was able to correctly “pair” the different types of wings, essentially saying “Plate A and C were the same, plate B and F were the same, and D and E were the same.”

The difference in spice and texture (crispiness) was noted by several participants. Spice is completely unrelated to thawing, and while texture may be affected by thawing, it can also be controlled by cooking a little more or less.

Conclusions and Recommendations

From the results, one can conclude that there’s no real taste difference between the different groups. Therefore, since it’s easiest to just toss them in the oven without thawing, that’s our recommended approach. That’s the result we were hoping for.


Giving Without Expectation

There’s an idea in the entrepreneur world that you should give of yourself without expectation of return. If someone asks for advice, a meeting, or help with a problem, then you should oblige out of some general sense of altruism. Unfortunately, followed blindly, this principle can end up with you wasting a lot of your time and the entrepreneur community at large not really gaining anything.

Black Holes

The problem with unconditional giving is that there are so many “black holes” in the community that will happily take as much as you offer without doing anything. A perfect example of this is the hot “wantrepreneur” who has lots of ideas and always wants advice on how to proceed. They want to know about Ruby vs PHP, Agile vs Waterfall, or S-Corps vs LLCs. You spend time answering questions and debating ideas, only to learn later that this person followed none of your advice and most likely did nothing at all. Your time was wasted.

These black holes just consume energy from the entrepreneur ecosystem and then do nothing with it. The community is chock full of these people, and it seems like new ones appear on a pretty consistent basis to replace those who disappear off the radar.

How can you give back to the community while defending yourself against these black holes? Here are a few tricks that work for me:

Check References

When someone reaches out, do a quick check on them and ask them what steps they’ve taken on their idea/project/startup/whatever. The more time and effort they have invested, the more serious they are. If someone is serious about their idea, they’re probably serious about your advice.

In all fairness, sometimes reaching out for advice is the first step someone can take. If they don’t have a lot to show yet, don’t necessarily give them the cold shoulder, but definitely follow my next tip:

Minimal Investment

If someone asks for a meeting, give them your phone number and tell them to call at a specific time. If they email you with questions, give them a quick 2-line summary answer and tell them to call you for more clarification. Finally, if they do call, set a hard limit and get them to the questions as quickly as possible, then schedule a follow up where they will call you again.

The goal here is to respond politely, but force the asking party to work for your time. I’ve received many emails asking for advice and responded with long analyses, only to never hear from that person again. I’m not sure they ever even read my reply. In the end I feel like an idiot. Much better to reply with, “Sure, I’m happy to give advice. Let’s talk for 15 minutes. Here’s my phone number…”

Assign Homework

When meeting with someone, assign them some homework and schedule a followup. Then, prior to the followup, ask for a quick report on their homework. If nothing has been accomplished (or more accurately, attempted) then there’s no need for a followup.

The people who value your advice will take action on it and come back with more and better questions. If someone doesn’t have time to implement your advice, then why do they need more of it?

Value Your Time

Time is the most valuable resource any entrepreneur has. If you’re wasting yours on people who don’t value it, then you’re cheating yourself.

I’ll sum it up like this: Give without expectation of personal return, but with some expectation of action. Put yourself out there and help your fellow entrepreneurs, but be smart about it and make them earn it.

P.S. This isn’t about you…

In case anyone thinks this is addressed at them specifically, it’s not. I just wrote this instead of a really long reply to an email asking for advice about SaaS billing. I’m currently waiting on that person to give me a call… ;)

Tags: entrepreneur

Adios DoLeaf


My wife Sarah and I have sold our interest in DoLeaf to our third partner, Ryan Felton. It’s been an interesting ride these past five years, but I’m juggling too many things right now and I need to focus.

I’m still a parallel entrepreneur, running Obsidian Portal (and delivering on our awesome Kickstarter) while trying to be a conscientious co-founder and junior developer at The Agile League. There’s enough juggling there to keep me plenty busy.

I can’t say that I’m not sad, as I think DoLeaf may be my best product idea so far, and the execution was pretty good from the start. With very little effort we still make some decent sales, and the customers (both the sellers and buyers) have all been happy. There’s a significant amount of work to be done, but if Ryan puts in a good effort, I’m sure he will find success there.

I keep thinking that I could have been a part of that success, but I have to be honest with myself. If I haven’t put any significant effort into DoLeaf in the past few years, that’s not going to change. At any point I could have reoriented my priorities to focus on DoLeaf, but I never did. Rather than dreaming about what might happen, it was time for me to realize that it obviously wasn’t important enough and I had to cut the cord.

Ultimately, there is a great mental relief in knowing that I am no longer responsible for executing refunds, sorting out order errors, keeping the server up to date with security issues, deflecting feature requests, and so forth. Managing and growing a business is a lot of work, and right now I’m happy to refocus all that work energy into my other endeavors.

So best of luck to Ryan and DoLeaf. I expect great things!

P.S. Now I can also brag to everyone that I sold my startup and used the proceeds to buy a boat. In truth, I bought a scratched-up, used, whitewater kayak, and it cost a significant chunk of my “exit” money, but maybe I’ll just leave that detail out of the story. ;)


Honest Feedback vs Unconditional Thumbs-Up

Whenever someone asks me for feedback or an opinion, I try to hit them back with a loaded question: “Do you want honest feedback, or do you just want a thumbs up?”

Of course, everyone always says, “Oh, I totally want honest feedback.” It’s seen as cowardly or weak to say, “Nah, just smile and say you like it, then shut up.” And honestly, that makes me sad.

I’m a fairly cynical person, so my feedback is almost always negative. I will poke holes in your idea and point out all kinds of flaws. At first glance, this may seem like useful information. However, I’m not that smart, so my feedback is probably not all that good. I have some experience, but I also have a lot of biases and half-baked opinions. It’s hard for me to separate out what I know from what I believe, so the advice I give is muddled with incorrect viewpoints.

Plus, sometimes you don’t really need honest feedback. You’ve worked hard on something, you believe in it, and you just want to hear that someone else believes in it too. This is especially true if you’re already committed to a course of action and feedback won’t change it. For example, imagine you’ve just bought a car and ask a friend, “So what do you think of my new car?” You probably don’t want to hear about its bad gas mileage or issues with reliability. You just want to hear, “Hey, that’s a sweet car. Good job!”

I know what it’s like to need unconditional praise. So, if you ever need an unconditional thumbs-up, please feel free to come and ask me for one. I will be happy to be your cheerleader and tell you that everything will go your way and tomorrow will be a better day. I may not believe it, but what I believe doesn’t really matter anyway.

Tags: entrepreneur

New Shiny vs Old and Busted

Lifehacker posted an article titled, “Six Apps We Used to Love (and Where They Are Now)" I smiled at remembering some of the apps in there, and suddenly it hit me: Many of these tools debuted around the same time or even after Obsidian Portal. My 7-year old app is older than these old and busted apps!

It can be disheartening to wake up one day and realize that you’re no longer the new shiny. People start to ding your product just because it’s a few years old, and it seems like many are actively looking for a “better” replacement, where “better” really just means “newer”.

Luckily for me, it’s not like “online RPG campaign management” is a hotbed of change. We get a new upstart competitor every now and then, but most of them vastly underestimate how difficult the problem space is. On the flip side, I can’t even imagine what it’s like in the “new way to listen and share music” game. A new shiny comes out in that arena like every week. You’re lucky if your app stays popular for 7 months, let alone 7 years.

I’m not sure what the takeaway is, but I’ll go with this: If you’re a developer, just accept the fact that one day your tool will be old news. Ignore the hype as much as possible and just do your best to delight your users. And, when you find everyone praising a young upstart competitor, chuckle to yourself knowing that sooner than they expect, they’ll be old and busted too.


Survivor Bias Yet Again

On the news of his acquisition of The Washington Post, I heard a snippet of an interview with Jeff Bezos from 1999, showing how forward thinking and wise he was at the time.

I forget the actual quote, but it was something like, “We want our company to have the best possible interactions with our customers of any company, ever.” Then the commentator talked about how ambitious Bezos was, naming his company after a river that moves bazillions of liters of water per second, just like Amazon does with e-commerce items.

Now that the guy is worth billions and buying newspapers for fun, we can all nod and look back and remark at his genius for building Amazon to where it is today.

But who else was giving ambitious, bombastic interviews in 1999? Maybe the people of Pets.com? Maybe Webvan? I don’t have any interviews to point to, but I doubt they were espousing poor customer service or recommending building a tiny company over a global mega-giant.

Always remember that we’re only hearing from the survivors, and none of them really know why they survived. We can put their words on posters, or post them to our Twitter feeds, but that doesn’t make us any more likely to join their ranks.

Is there anything we can learn from listening to these success stories? Definitely yes, but only when contrasted with the failures. And since the failures aren’t out buying newspapers and getting their quotes in the news, it’s up to us to do that research on our own.



Yesterday’s post, “Working From Home is Like Saying No to Drugs”, caused a bit of a stir, which was expected (or hoped for, at least). Also as expected, I did a poor job of making my point and most people missed it.

I was attempting to make a reductio ad absurdum argument, basically stating that if productivity is all that matters, then a lot of absurd policies are suddenly viable. Forbidding work from home is just the start. You’ll also want to forbid hiring pregnant women. They will show reduced productivity within the next nine months, and potentially for years after that.

Unfortunately, this situation is not so absurd that we don’t need laws to protect ourselves. The Pregnancy Discrimination Act makes it illegal to discriminate in hiring decisions based on pregnancy. In other words, we need a law to protect ourselves from what seems absurd.

Obviously, now I’m equivocating between pregnancy (a basic human right) and working from home (at best, a perk). But I think my point stands: Evaluating a decision or policy solely on maximizing productivity for the company is wrong and leads to absurd policies.

Tags: wfh