Strength in Chaos

Have you ever been so close to the edge that you no longer know how to tell whether you’ve crossed it? It’s a hard thing to live this way, yet this is all I’ve known for years. When your credit cards are maxed out and the only thing you have is the cash in your wallet, it’s a paralyzing feeling just to pay a bar tab. There’s a certain panic in spending 60% of your available wealth on two beers and a stack of potato fries. Sure, you play off the declined credit card as an oversight, but deep down, you know just how close you are to oblivion.

It’s easy to see how such a situation might cripple anyone. Still, there’s a strength to be found in all that chaos and uncertainty. If you can look past the debilitating rejection of having tens of thousands of dollars of credit, all stretched to their full extent, you find yourself in a peace known to few. I imagine it feels something like drowning. Despite the sudden onset of declined credit transactions, there’s a looming catastrophic quality to the experience, like watching the boulder from afar as it tumbles down the hillside toward your imminent demise.

I envision it like kayaking over a waterfall. Sure, I could keep a constant pulse, checking in with the sherpa shouting from the shore, waving his arms madly in a futile attempt to inspire me to paddle toward the dock. Instead, I find solace in the knowledge that there is more to learn in the quick trip over the edge than I could ever hope to encounter in the safety of knowing that there is another force dragging my boat. Whether I measure it or not, I’m going past the event horizon. I can not know the terror that awaits me, nor could I ever embrace its totality. Still, I close my eyes and sing to myself sweet songs of my inevitable victory.

You may call it foolish or even insane, and you’d be right. In describing the audacity of hope, you will inevitably find yourself questioning the basic fundamentals of what it means to live. I promise I don’t have any answers you want to hear. Frankly, there have been as many times as not that I’ve wondered how much easier it would be to flip my boat and drift away in serene aquatic asphyxiation. But I’m not interested in that death. I have far too much to contribute to this world to seek that path.

I’m not done with this life after these 36yrs. I’m doubling down. I’m ready for another 72, and I’m willing to bet that at the end of all those years, I’ll do it again, if for no other reason than to dare the universe to give me a thousand times more hardship than I’ve faced in these 36yrs. If I can survive this chaos and use it as a source of continued strength, another hundred years will only serve to anneal my heart and soul that much more. I no longer believe there is anything the universe could throw at me that I could not use to grow stronger. And that is the most peaceful feeling I could ever hope for.


Get Married or Break Up or Maybe Something Else Entirely

I didn’t think it would hurt this much. When I told her I wanted to marry her the first time, she smiled and thought I was being dramatic. Maybe I didn’t mean it. Maybe it was a raw expression of emotions I didn’t understand. I didn’t have a ring. I didn’t propose. I just told her in the best words I had that she means the world to me. She always will.

This time, it was different. I had a ring. And I meant it. More than I’ve ever meant anything in my life. I’ve been married and divorced, yet I’ve never loved someone so much. Sure, it wasn’t a ring for her finger. It was a beautiful handmade bracelet a good friend gave me from India. I knew it was foolish to buy her a traditional ring, partly because I’m broke right now and spending my last remaining cash on a ring would mean she gets a decoder ring from a cereal box. More, it was a matter of simple facts. I’m moving to San Francisco, and she lives in the Other Bay Area, 3500 miles away.

I’m not sure what hurts more – the fact that we will be so far apart or her reaction when I gave her the bracelet and told her I want to marry her, but it’s not going to happen now, maybe not ever. It felt like she said yes to a question I didn’t ask. She kissed me with a passion I have rarely experienced with her.

We had only recently broken up. She said I love her too much, so much that it’s overwhelming. She thinks I’ve made a series of bad choices with employment, and she’s probably right. She doesn’t like it when she feels like I take better care of her than myself. Then, I told her I was taking a job at a great company in SF and would be moving within the month. I guess that was what she needed to hear to remind herself how much she loves me. We can’t be together now, but we’ve never been closer. The connection we feel with each other is stronger and more robust than ever.

They say absence makes the heart grow fonder. I hope not, for her sake. I fear if I love her any more than I already do, she will dissolve into the brilliant light of my heart and be lost forever. Still, I walk the city streets, taking pictures, find examples of thing she would love. I only send her one in ten because I don’t want my intensity to be her burden. I also don’t want to tease her with a life of adventures she shares only by digital proxy.

For now, our lives diverge. Like paths in a Robert Frost poem, it’s bittersweet and beautiful.

My Last 48 Hours in Tampa

7:50pm: get a Lyft downtown. Meeting Sierra for a drink.

8:05pm: Randomly run into Emily. She is also joining us, but I had no idea. Very happy to see her, as I had been trying to coordinate something before I leave. Emily tells me stories of her sudden and inexplicable hospitalization.

8:25pm: Sierra arrives. Drinks commence. Conversation is free, open, and genuine; just as it always is with good friends.

9:40pm: Sierra laments her absurd and hilarious mishap involving a boat, a slippery ladder, and stitches in her vagina. She shows me pictures. Legit. Ouch. Hospitals are becoming a theme…

10:10pm: Ride home with Sierra, who gingerly comments on the bumpiness of the road. Empathy cringe. I don’t have a vagina, but I imagine stitches there must be painful, especially while seated.

10:12pm: Remind Sierra her sunglasses are still at my place. She left them there 18mo ago when she gave me a massage. That was nearly the last time I saw her. She is unsurprised and thankful.

10:20pm: Outside my apartment, Sierra waits in her car while I run inside to retrieve her sunglasses. She gives me a big hug and wishes me well on my trip. I’ll see her again in a few weeks.

10:22pm: Attempting to burn through the last of the white widow before I go. Watch some old Star Trek. Nostalgia. Sleep soon follows

6:26am: It’s Thursday. I’m getting roasted tonight. My best friends in Tampa are sending me off properly. Looking forward to it. Shit, this is really happening. Snooze.

7:29am: Think of Sophia. My internal clock is incapable of sleeping past 7:30am, largely because Sophia’s birthday is 29 July. She sets her alarm at that time, so I’ve been trained to wake then, whether she’s with me or not. Miss her. Going to miss her a lot more than I’m comfortable admitting.

8:15am: Off to the WaVE. Or not. Distracted by Mike’s random app ideas from yesterday. Let me just take an hour to build this web app real quick. Might as well record my screen while I do it.

9:05am: App complete. Text Mike with the good news. Ok, now to get ready for my last day at the office.

9:28am: Witness a man, likely in his 60s, walking barefoot across Kennedy Blvd, wearing only a pair of shorts. He walks on the white painted part of the street. Smart man. He looks pensively at the bus stop bench for a moment, then grabs the two unidentifiable items from the bench, nods affirmatively. Light is green. Must go now, strange man.

9:30am: Arrive at the office. No interns at the desk. Typical. Feeling like I won’t get much done today. Also typical. I do more code-related things at home anyway.

9:40am: The congratulations begin. Chris, my neighbor, is the first to offer his regrettable and envious sentiment. He also asks me to help with a code problem, which I do. Volunteer time and a willingness to help is a key part of my having an office at Tampa Bay WaVE.

11:30am: Congratulations continue to punctuate my morning. Getting some editing done, but not very focused. Roasting is on my mind. Pan-fried ginger, I believe. Smiles. Now, time for coffee. Walk down to coffee shop downstairs. More goldbricking with baristas. I order a cappuccino, only the second time I’ve done that. Jared gives me the “wait… what?” face. I always order a small coffee.

2:08pm: Set up in the studio for podcast recording. Justin is late. He is forgiven because he brings a bottle of bourbon, which we haven’t had on the he show in months. We talk about his woes regarding web service API versioning. We talk for so long that we must break it up into two episodes. Good stuff. I asked if he wanted to do a farewell show. He said no. Not ready to admit I’m really moving yet. Hope this won’t be the end of the show. It’s far too much fun to give up just because we don’t live in the same city anymore.

3:40pm: Finish recording. Great episodes! Strike all the recording gear and head back to my office for editing. No possibility of getting this out before the roast. Punt. Do it on the plane tomorrow. Let’s get drunk instead.

4:05pm: People start to arrive for the roast. This is going to be good.

4:20pm: Drinks are flowing. Pizza is on its way. Great company already ramping up for the roast.

7ish: The roast was epic! Raffled off a bunch of my stuff for entirely less than it was worth. I think we gave away about a thousand dollars worth if stuff for a little under $100. Hope y’all enjoy my stuff as much as I did. Thanks for coming!

8ish: the roast has evolved into a band practice for Tech Jam. Ned straps on the wireless mic. I use the wired one. We sing. Justin plays guitar. It’s amazing. Really feeling a lot of flow and synergy. Only need to practice songs a few times and it sounds amazing. Gathering an audience, all very impressed. Deb tears up the background vocals. She’s going to be on stage with us, if I have anything to say about it. Of course, if Justin’s wife gives birth that day, there will be no show for us. And that’s how it’s supposed to be. 🙂

10ish: Done with band practice. Heading to the hotel bar across the street. Bump into Saxon, who has managed to find the prettiest girl at the bar and captivated her attention. Turns out she’s 50. Brava, ma’am. She looks like a sexy 32. But that’s Saxon, always ballin’ out. Everyone else drinks gin. I drink bourbon, with authentic maraschino cherry.

10:30pm: Trying not to be hungover for my flight, I bow out. Many hugs. Many good vibes. So long, folks. I’m going home to smoke some weed.

6:15am: Up early. Pleasantly feeling fine. Ok, gotta pack the suitcase. Shit, left it at the office. Ok, laundry then. How do I fit two weeks worth of clothes into a suitcase the size of a medium sized dog?

8:30am: Ok, gotta get to the office to get my suitcase. Then back home to pack. Then back to the office. Still have some editing to do. Gotta publish an episode today…

11:02am: Call from Mitch. Deb’s birthday is today. Going to have lunch to celebrate. Just finished packing, so I’m good to go.

11:16am: Chat with Lyft driver about SF. He wishes he were moving.

11:35am: Arrive at Anise for lunch, early. Find table for six.

11:45am: Mitch and Deb arrive. Wow, the samosas are amazeballs! Almost worth not leaving… Almost. We have three orders. 🙂

12:45pm: Bill is paid, gotta get back to the office! Got a plane to catch.

1pm: Stop by Justin’s office. He’s ready to go. We drive to the airport. I tell him about this article, including the random highlights. We laugh. The look on his face when I tell him about Sierra’s stitches is priceless. I will miss him the most.

1:30pm: Security was a breeze, like Ganesh clearing my path. One person in front of me in line. Effortless. It’s like the universe wants me to get to California.

1:43pm: Sitting at the Cigar City brewpub. I will miss their excellent beer. I will miss a lot of things about this town. Finish my beer and head to the gate. Perfect timing.

2:40pm: Wheels up TPA

Mentorship is Worth the Pay Cut

I’ve been writing a lot lately about humility and vulnerability and leadership. All of those things involve a great deal of sacrifice and a willingness to embrace the unknown. This week, I spent a few hours each day helping kids build software. Most of them had game ideas. Some had seemingly impossible goals they achieved and surpassed. A few finished early and went on to make two and even three apps. All of them showed something on a mobile device or laptop after only a week of development. We’re talking about campers age 10-12 building fully functioning games from nothing in a few days, all with original artwork.

As someone who started learning to build software at age 13, I am humbled to see what these amazing young people are doing each day. The rate at which they are able to absorb and apply the fundamentals of interactive product design is simply breathtaking. What was most astonishing to me was how much they remember. With every adult I’ve trained, they all universally needed to be shown something more than once. These aspiring engineers are routinely demonstrating their attention to detail and appreciation for the moral and ethical implications of their efforts.

As someone who has worked with intellectual property for years, I feel great pride in these intrepid young people. They recognize the right of the creator to be credited and possibly compensated for use of their work, even when discovered through Google Images. I feel embarrassed for my marginal use of such copyrighted material in my past work.

I’ve written before about the rockstar curse and what it feels like to be openly referred to as a god (still happens, still uncomfortable). My experience this week changes everything. I thought my choices were limited because I have trouble finding anyone with more skill or expertise than I have. As it turns out, I was looking the wrong way. Mentoring is the right way. I learned more this week than in the last month of client work. But it’s not about me. It’s about the brilliant young minds who will go on apply what we’ve taught them. That’s worth more than money can buy.

Measure Behavior. Stop Asking for Feedback

“Hey Twitterverse! Check out our new awesome app concept. Enter your email address to be included in our arbitrarily limited beta. We’ll nag you for feedback after you’ve barely used our hastily assembled product. It’s going to be epic! We’ll make billions and you’ll get this rad t-shirt.”

Does this sound familiar? There’s a good chance you’ve heard of some new concept before, making big claims about what they are eventually going to do for the world. Often, the people who build these concepts have no experience doing so. The lucky ones have guidance from mentors, folks who have founded, built, and sold companies before. Maybe it’s more accurate to say that some mentors are lucky enough to work with startup founders who listen. In nearly every case of entrepreneurial failure I’ve witnessed, the founders were reluctant to hear any advice that put them outside their plans and expectations about their business. Some died a quick painless death. Others managed to collect revenue, only to wallow in the pit of customer retention despair.

What was their primary mistake? Asking for feedback.

Many first-time entrepreneurs build immediately, based on their intuitions and (hopefully) years of experience dealing with some pain in a specific industry. They do not take time to survey potential customers. They are often blinded by the belief that they must be first to market. It never hurts to be first to market, unless you’ve rushed to get there. Typical bootstrappers have no budget, which means they choose to skip important steps, such as persona development and user research. Instead, they go straight to visual design so they can have pretty pictures to show investors. From there, they hire code monkeys to make software that looks like the pictures. This is exhausting for everyone involved, as no high level awareness of the core product exists without sketches and storyboards, which were skipped to keep costs low. Eventually, they send out those beta invites to the few hundred people who have expressed interest.

“Tell us what you think!” might as well be “share your deepest concerns about your edge case, so we can focus our time building things only one user requested instead of the one thing we set out to do in the first place.”

Publishing a product and allowing it to grow organically is a great way to gauge customer interest. It’s also an excellent path to information that will serve far greater purpose than customer feedback. By reviewing analytics of actual user behavior, we see a pure unfiltered stream of high quality information. Communication is hard. People lie. They don’t ask for what they really want. They are inarticulate. Behavior data never lies. Ask for feedback, and you’ll hear many suggestions for features. You’ll need to interpret the feedback, collect similar ideas, prioritize the resulting feature requests, and make difficult choices about which features to add and in what order. Look at behavior analytics, and you’ll see precisely the point in your workflow where users give up. If 75% of your users click cancel at the end of an interaction, there’s a good chance the interface is hard to use.

Focus on what you know, not what you think you know, nor what you hope to be true. Hope is not a business model. Feedback is at best a distraction. User research and behavior analytics are your salvation.

Wearable Society

Let’s do a thought experiment. Try to remember the first time you encountered someone in a wheelchair. In your eyes, it was an anchor. You most likely focused on the limitations they must encounter regularly in everyday life. In their eyes, it was a rocket ship. With a little finesse, it could take them to places their body would not avail.

I think of social media in a similar way. Some people see it as a possible threat to personal security. Others see it as a mechanism to provide security through community. No one disputes the additional exposure we incur for using location services on our mobile devices. The key is to provide the sensory value while also offering the ability for the individual to control their level of exposure. This personal authorization layer is critical to the long-term survival of any mainstream solution for data publishing.

As personal devices multiply, the infrastructure required to coordinate all the information becomes exponentially more complex. Sharing this information in real-time helps people make decisions. Decisions are the currency of the internet of things. The choices we make now ripple outwards to subscribing devices, which take actions based on our decisions. In many ways, this is the definition of society. Disney got it right when they depicted a team of dishes and appliances working together in harmony to achieve the goal of cleaning the house. Usually, they represented this as magical in nature. I’m sure Arthur C. Clarke would agree that we have achieved sufficiently advanced technology that we barely believe our own abilities.

Fortunately for our childlike dreams of magical solutions, reality isn’t far removed from the dream. We have just enough understanding of the idea of connectedness to envision a world where the conversation involves machines. We’ve all seen it from early life, when we watch robots make jokes with each other using noises we can’t understand (but still laugh about) in Star Wars. We’re already indoctrinated by science fiction to accept this future as a natural, inevitable outcome, and we couldn’t be happier about it.

So, when the waste band of my running shorts tells my shoes to cool off my feet, so my body temperature cools, allowing me to reach a higher natural speed, I doubt I’ll be aware that they’re having a conversation at all. In fact, I won’t even know it happened until I look at the details of my weekly fitness report and see my average cruising speed has increased. And if I can authorize my doctor and my immediate family to see those same details, I guarantee I won’t be angry if they comment about it in casual offline conversation. It would be wonderful if I could share this data with a wellness coach, so they can make adjustments to my daily regiment (diet, exercise, rest, etc) on my behalf. Granted, I’ll still eat a pint of ice cream all to myself from time to time. You can’t fight basic carnal desire…

All of this is possible with a little magic, if you choose to see it that way. Any way you look at it, we can not ignore the impact of machines on human society. I don’t think we’re headed for the Matrix, but I do believe wearable technology will change the fabric of humanity, pun absolutely intended. I, for one, would love to have a rocket-powered hover chair, which is clearly the natural evolution of the wheelchair. Duh.

Give Day Tampa Bay: A Humbling Experience

Rarely in my life, some say too rarely, I have had the good fortune to experience something awe-inspiring, something that humbles me and reminds me how powerful community can be and how small I am in the big picture of the universe. Today, I experienced one of those moments. I’d like to share it with you.

Last Thursday, shortly after recording a podcast episode for Distilled (iTunes link), my co-host, Justin Davis, made a comment to Ned Pope that changed my life. Ned is president of Florida Next Foundation (, which supports the efforts of non-profit organizations in Florida. His office is on the opposite side of the building from mine. Justin’s is halfway in between. Before last week, we barely discussed much detail about today’s event, but we chat all the time about the various goings-on of our lives. Ned and I shared a stage last year at Karaoke for the Kure ( He is a rock star in more ways than I thought possible, but that’s a story for another time.

Justin’s comment was a suggestion that we interview some of the folks running non-profits, as part of a live podcast during Give Day Tampa Bay ( I think he meant to do it as an audio thing initially, but it quickly escalated. Sunday night, we collectively realized we had never done a video podcast, let alone a live video podcast. Monday was a scramble of “oh shit” moments, as we quickly surmised we did not have the capabilities we needed to achieve the goal. Cabling issues persisted until this morning around 10:45am, when Justin returned from Tiger Direct with the one cable we didn’t have. Quickly, things fell into place.

What happened after that was one of the most impactful experiences of my life. I’ve walked away from a devastating car wreck uninjured. I’ve held my newborn child in my arms. I’ve built some products that captured the hearts of millions of free users and others that made over $1B in revenue. All of this pales in comparison to the magnificent display of collaborative problem solving and general excellence I witnessed today at Tampa Bay Wave.

We went from a whim to a high quality live video broadcast in under 48hrs with almost no structure at all. We tried two different cameras, only to barely succeed with a just-in-time cable purchase. We tried two different sets of mics because of background noise. We tried to green screen the Tampa skyline as a backdrop, but couldn’t get the software to play nice. We called an audible and stole (borrowed?) tablecloths to use as a backdrop. The only challenge we faced that we didn’t overcome was a Skype call-in for one of the ten guests we had scheduled. For that, we needed Just One More Cable™. The green screen was just a nice-to-have anyway.

Amazingly, nothing went wrong. People even started saying “nothing’s going wrong! this is amazing!” which almost begs for something to go wrong. But it didn’t. We coordinated video transitions smoothly. We showed supporting material when appropriate. The conversation was engaging and personal. We really had an opportunity to showcase some wonderful people doing great work for all aspects of the community. There were funny moments. There were tragic moments. Nobody dropped the F-bomb. For over three hours, we were a window to the world, empowering non-profit champions to tell their story.

This was an entirely volunteer effort. No one got paid to do it. And in the end, we raised over $1M for local non-profits in under 24hrs. That’s the power of community, and I’m proud to be a part of it.