Category: Uncategorized

A friend hit me up for some feedback last week and I thought I’d share.

Disclaimer: I’m not a startup advisor (except when I am), nor do I coach people (except when I do), so take it for what it’s worth.

So my friend — let’s call her Jasmine, since I think that’s a beautiful name and I like the idea of having a friend named Jasmine — is considering a project that would provide a service to the technology community in her city. It’s part startup directory, part job board, part connection platform. There’s a successful model for it here in NYC and this serves as the inspiration.

Jasmine has shopped the idea around to those who stand to benefit from it, and has been met with considerable resistance. Chiefly, as it turns out, because there are a lot of people who want to be the first to execute a project of this sort and they feel threatened by my friend’s interest in it.

To add another layer of complexity, Jasmine is in a bit of a holding pattern with her career.

She quit her well-paying job to strike out on her own in search of work that fulfills her. She’s known in social circles for having a competency in one particular aspect of digital media, but it’s unclear if this is what will “put her on” if you will.

When probing further with the idea, I found out that there are a few people interested in helping out, and that there is not yet a clear path to monetization.

So. My feedback was as follows:

1. No one’s opinion of the idea really matters, and asking the wrong people (those who want to ship it first) for their opinions seems to be a bit incredibly counter-productive.
2. If this isn’t a business, then what’s the point? You’re at a point in your career when your next move really should put money in your pocket and earn you respect in your industry, so anything not likely to hit that mark should be cast aside immediately.
3. There will obviously be some political backlash in your city’s (relatively small) technology community among those who want to pull this off. To be dramatic, at the risk of oversimplifying: are you willing to be hated until you’re loved?
4. Is this just the idea of the month or are you committed to seeing this through? You’re going to have to slog through months of thankless work in order to even gain some initial traction, and it’s possible that this still might fail.
5. Along the lines of the last point, it will be a travesty if, knowing what you know and having worked through these questions, after getting people excited about this idea and hacking away until it’s no longer interesting, people visit the website in six months and it has become a GoDaddy parked domain page. If you do it, see it through.
6. Having a few people interested in helping out might not actually be a good thing. If this is a business (and I hope it is) then are you prepared to pay these people? Will they all be happy to toil for free while you earn from it? Or has the expectation about money not been set at all?
7. Unless you’re going to learn the technologies required to execute this project, you’re going to be looking at hiring a developer to help make this happen. Have you thought through this?

I don’t need to know the answer to these questions, and neither do you. But I think the questions need to be addressed before another step is made.

Just happened upon this section of a restaurant’s website.

Emphasis mine:

Our delivery and credit card minimum is $10. Before ordering, we ask that you please consult our maps to see if you fall within our delivery range. Due to the high volume of deliveries, we can only make exceptions within reason, in which case we ask that you meet a $40 delivery minimum. We charge a 10% delivery fee for orders over $100.

Madness.

Sean “P Diddy” Combs is by almost all accounts a terrible rapper.

But despite his shortcomings as an emcee, he has managed to build one of the most successful and influential hip hop empires in history. Not to mention his restaurant, alcohol, and clothing ventures. Forbes estimated his 2012 net worth at over half a billion dollars.

That’s billion with a “B.”

Germaine “Canibus” Williams, on the other hand, is an emcee who rose to prominence in the 90s, and is regarded among hip-hop enthusiasts as one of the most talented lyricists of our time. I’ve been a fan for years and despite his lack of commercial success, he’s been an influential figure in hip hop who was known for outshining other artists when contributing verses to their songs.

Last I heard, he had been discharged from the ARMY for being caught with marijuana. And I’m not sure his music career is faring too well, either.

These are extremes, sure, but I’m making a point. I love examples from the music industry because it’s easy to gauge influence and success and trace the arc an artist’s career.

Seems to me that the thing you’re judged by might not be the thing that matters, and it’s more important than ever for artists to determine what their personal goals are when striking out.

Do you want to be famous? Rich? Respected? Accepted by most or just the people who get the joke? As an artist, I think it’s dangerous not to decide. And as a marketer, I think it’s foolish to make snap judgments without digging deeper.

The more I learn, the more I disagree with those around me about why things are the way they are. I think this has to do with people wanting to fit in and be accepted (it’s en vogue to talk about how good or bad something is when that’s the popular opinion, but it’s annoying to deal with a contrarian all the time).

As it relates to my career, I’m learning what the role that reputation and excellence play. You can be popular and well-liked and influential…and completely broke. This was one of the most interesting things I learned when I started making my living online — it’s a complete house of cards out here.

So my talent and natural abilities matter, sure, but if they’re not aligned with what matters in the context of those who need me (my team members and customers) then it’s for naught. People remember excellence.

I call my CEO the dark horse of web performance because he’s not a public figure in that he’d be recognized walking down the street, but the people who know him (large companies who have hired his firm, the hundreds of thousands of customers who run their site using technologies he architected) respect him immensely.

Because he’s got excellence in muscle memory so to speak.

That works.

The Indian restaurant that my apartment sits on top of is still proudly displaying an award received in 2005. They have a right to be proud, but it makes me wonder if the quality of the food and experience has deteriorated in the past eight years.

Has nothing remarkable taken place since then? Were the judges bribed with unlimited Mango Lassis that year? Was the 2006 batch of bribe drinks so awful that not even cheating could win them an award?

On a similar note: I sometimes review resumes for people who find them useful. Occasionally, I’ll see an award or distinction that’s the professional equivalent of saying “I was in the boy scouts and caught a fish one time!”

Cute, but cut it out.

If there’s nothing you’re proud of that has taken place in the past quarter or year and you’re not working on a product or project that will get you there, then what exactly is it that you’re doing?

…it will show.

My friend Ankit wants to work with Rap Genius. Clearly.

If they don’t hire him, someone will.

I’m currently being forced to enjoy an extended layover in Mexico on my way back to the states. I missed my connection on account of some astounding operational inefficiency here, but that’s another rant for another day.

As I was going through security following my arrival here (I guess they wanted to make sure that I hadn’t procured any explosives in the walk from one plane to another?), I was asked about the wines that were purchased in Argentina.

The gentleman wanted me to produce my receipt for the purchases and when I couldn’t find it after a quick look in my bag, he asked me if I wanted to search my other bags for it.

I told him no.

Him: “You don’t have time?”

Me: “I just don’t feel like it.”

I was tired of having my clothes and electronics rifled through, irritated about missing my initial connection, and of course ever-skeptical of the hoops we have to jump through in airports.

Interestingly, they let me go without another word about it. Security indeed.

Plot twist: there were alfajores in the wine box as well!

On the eve of my departure from Argentina, I’m reminded of how growth alone isn’t enough. Equally important is never falling past a certain point after progress has been made.

I’m shooting not only for new habits, but also for which a new level of progress below which I never fall.

Seeking out advice is seductive, because it feels like we’re making progress.

What we’re often doing, however, is trying to avoid deciding. More specifically, we try to avoid taking responsibility for a decision made that might end up embarrassing us. Feeling like a failure. Publicly ostracized.

In our noble quest to avoid deciding, we prioritize information-gathering, not failing, learning as much as we can, and all manner of good-sounding excuses that do nothing but prevent us from living the life we want.

What we should instead prioritize and value is courage, decisiveness, conviction, power, intent, resolve, and clarity. These things only come from being in the habit of both deciding and being willing to accept the result of what we decide. There’s no way around it.

My interests are many and varied. My friends and advisors and mentors know certain aspects of my character, but virtually no one understands how these things come together to form who I am.

My business partner doesn’t know that I write poetry, my musician friends don’t know (or care) that I build servers, my parents have no real idea what I do to make money, and only a handful of people know about my interest in improv, standup comedy, and singing.

Even if I took a week to explain everything about myself and my interests, you’d never understand what it felt like when I wrote this post or when I went on this trip or when I got off the plane five months ago (!) for my relocation to Argentina or why I sometimes work late into the night until my eyes burn.

And that’s fine.

But it means that I can never ask someone if I should attend conference x or move to country y or join club z. Not only do I disregard whatever feedback I’m given and do what I was going to do in the first place (you do it too, don’t front)…it’s both pointless and the manifestation of me trying to stall.

Courage isn’t developed in the shadows, nor are nerves of steel fortified behind closed doors. It happens on stage with your palms sweating while the voice of doubt in your head is the only thing louder than the applause of the crowd that you don’t notice because you’re petrified.

The fear is worse than the failure.

“Better late than never, but never late is better…” -Drake

This weekend, I had the pleasure of reporting to a customer that we were two days ahead of schedule and that we could launch early. They were thrilled at the news and I beamed when typing the message, irrespective of the response I anticipated.

I made a promise, kept it, and was ready to ship. Rah.

This isn’t the way every project goes, unfortunately. In one of my many roles (I know, I know…you have no idea what I do for a living. Join the club.), I implement technology solutions involving the software used to host websites.

On a good day, the only emails I get are from people wanting to throw money at me and telling me what a great job I did. Since I retired from exotic dancing, however, these “good days” are a rarity.

Instead, I often put out fires.

These vary in severity and frequency, but they always come. It’s just the nature of the beast. Because of this, how fast I get through my tasks changes…every day. Things typically blow up all at once, everywhere, so business hours during weekdays can get pretty exciting.

And by exciting, I mean an entire day can pass without me making meaningful progress on my important tasks. This is why it’s 10:30pm as I write this and I’m about to “go to work” 🙂

The point is, deadlines sometimes slip. It’s awful, I hate it, it’s preventable, and it still happens. I know. Don’t look at me like that.

Customers are generally gracious and understanding (most just want to be kept in the loop, few have deadlines that will end the world if missed) if you communicate properly, and for this I’m grateful.

But it’s still never fun to deliver a project late. It reflects poorly on me as a professional trying to build a reputation, reflects poorly on the mastery of my craft (if I were better at what I do, some fires would never happen), and reflects poorly on those who put their name on the line for me to be in the position I’m in.

Even if the deadline doesn’t matter and a final deliverable is received with a standing ovation, it still feels like I’m saying “Alright, here’s your broken promise — think of me next time you want to be disappointed!”

The best late can be is still late.

But shipping early is like delivering magic with a bow on it — few things compare.

More magic, coming right up.

iMessage didn’t initially ship with the ability to sync messages between devices. The result for many people is multiple conversation threads that remain unsynced.

For me, this was maddening.

I travel quite a bit a lot and I don’t always take every device with me, so the ability to have my discussions synced regardless of the device I’m chatting with my CEO on (for example) is critical.

Setting it up properly isn’t hard, but they key is twofold:

1. You must configure all devices to receive messages at the same number or email address
2. You must set “Start new conversations from:” to whichever number or address you selected for #1

That’s it.

For you visual types, here’s the step by step instructions with screenshots of my settings. My cell and alternate email addresses are redacted, terribly sorry. And shouts out to Frederick for helping me get this set up correctly in the first place.

iPhone
Settings > Messages > iMessage: on
Settings > Messages > Send & Receive > Start new conversations from: [email address you use across all devices]

iPad
Settings > Messages > iMessage: on
Settings > Messages > Send & Receive > Start new conversations from: [email address you use across all devices]

Mac OSX
Messages > Preferences > Apple ID > Enable this account: [checked]
Messages > Preferences > Start new conversations from: [email address you use across all devices]