Mentors - Closing The Loop

At Next Big Sound we have been incredibly fortunate to have world class mentors. I count Troy Henikoff and Jason Mendelson as the two most impactful. Instead of talking about them in particular this post I’d like to pass on what I’ve learned about finding and engaging mentors overall.

I’ve had people ask me explicitly to “be their mentor.” It’s not like a thesis advisor, or any formal position, it’s a relationship and like any relationship, it needs to be two ways. But what could a 40-year-old serial entrepreneur or venture capitalist possibly learn from a 22-year-old, first-time entrepreneur? And with hundreds or thousands of people reaching out to them each year for money or advice, why would they spend an inordinate amount of time and energy with any one of them? A feedback loop. Closing the circuit. Let me explain.

I’m sure I get 1000x less inbound requests than Jason or Troy but now that I have a lot of people reaching out to “pick my brain” I can get a sense of what happens even at my scale. I’ll have one 30 minute, first time, meeting with someone who connected with me via a warm introduction. The 30 minutes are slammed in the middle of an afternoon between my calls with customers, investors, current team members and prospective hires etc. I spend the first 10 minutes orienting myself to their situation - trying to subtly remind myself how we were connected, where they came from, where they are going, what they hope to get out of this meeting etc. We dive into a few areas and I will go into whatever relevant areas they want to talk about. We usually end the last few minutes with me prescribing something I’ve said before: time-gating; pre-mortem analysis; or don’t ask for money, ask for advice. Or I’ll make a few introductions. And then just as quick as the relationship started, it ends.

Here is where the feedback loop comes in. Right here, where 99% of people fall off the face of the earth, right here is where the relationship can become bi-directional and start building towards something beneficial for both sides. A quick note that says what happened!!#@&!

Did you use time-gating and it blew up in your face? Was the pre-mortem supremely helpful? Why? Did the introduction lead to the job you wanted? Or was it a waste of time? Even if you did literally the opposite of my advice, and it worked like a charm, that would be incredibly useful for me to know so I can stop blindly recommending something and can adjust my world-view.

If I wanted to find an amazing group of people who could be in my corner, give me advice along the way, and mentor me through a dynamic time in my life here is what I would do:

• Set a calendar alarm 2-4 weeks after my first meeting with the person with a reminder of the distinct piece of advice that was given or introduction that was made.
• Send them a short email that day with the implementation of the advice, what happened, and any other articles, video or reading on the topic that is relevant (this last one is just a bonus).
• I would set a second calendar alert for that person 4-8 weeks after that to ask for another quick call or email with hopefully a new, specific challenge I was facing.
• Rinse and repeat.

This obviously has to be paired with continual progress, sincere professional challenges you are facing, and solid interpersonal chemistry, but this is one of the surest ways I know to “find a mentor.”

For avoidance of doubt - I was far too clueless to do this with Troy or Jason, Troy was a professor of mine at Northwestern so we had forced interactions every week for 12 weeks. Jason was a warm intro and then lead mentor during Techstars for 12 weeks. My recipe above is trying to manufacture something like that in the wild and I’ve ended up using it with success myself.

“I’d Love to Pick Your Brain”

I used to say this phrase. This is, until I had it asked of me hundreds times over the last five years.

Three things about this phrase make it one of my biggest pet peeves:

First, it’s lazy. It skips the part where you think-through and specify exactly why you’d like to meet with your target. Most folks are busy but can make time to give relevant, helpful advice. Do you have 10 minutes for me to ask you a few questions about how you structured your first commission-based sales agreement? I’d love to ask you a few questions about your M&A process, particularly how involved your board was during that period. With more specificity your target may be able to answer quickly via email, bring a few constructed thoughts on the topic, or recommend someone else on their team or in their network to talk to instead.

Second, it sounds incredibly one-sided. What do I get out of the 20-60 minutes? My brain picked? What about learning what you’re excited about and planning to do? Or the last two experiments you’ve tried? Or your impression of the opportunities in the current market environment?

Third, the mental image of a  brain being picked grosses me out for some reason. 

I know this post sounds probably sounds like a mean, old curmudgeon. I’m fine with that. I like to think I’ve only collected a few pet peeves in the business world. Don’t get me started on lunch meetings (that’s for another post)...

The Next Big Sound Is Not The Last Big Sound

The next big sound will, by definition, be some combination of previous styles, recombined and re-imagined. Elvis Presley and rock and roll. LL Cool J, Run DMC and hip-hop. Skrillex and EDM. The biggest artists in history were the ones who crossed and combined genres, influences and styles in a way that resonated with millions of listeners.

Artists like this are hard to understand at the beginning of their careers because nobody knows what to do with them. They don’t fall into the pre-existing genres, radio stations don’t know which format to play them on, record stores don’t know where to stock them, parents don’t know what to make of them, and the press doesn’t know how to describe them. This is one application of my theory of intersections, that the most interesting things happen at the intersection of previously separate fields.

The artists that are simply following the sounds of the day are playing a long game of catchup and likely never to have the crossover and timeless appeal of the early trailblazers. That said, most trailblazers die in obscurity. And here lies the paradox.  

By the time a track like Omi’s Cheerleader or Magic’s Rude is number one, it’s too late for that exact sound. If you are only listening to the current top of the charts, you miss the months and years that have built up to that point. You miss the years when Magic! and Omi were writing, performing, recording, and finding their own voice that didn’t sound like what everyone else was currently listening to. If you try to mimic their style or sound, without authentically combining it with your own voice, you won’t get very far.  

I see the same thing in startupland. If you just watch the type of companies getting funding on Techcrunch, written about in the press, and think that you should start another gaming company (2009), mobile app (2010), big data company (2011), daily deals site (2012), Uber or AirBnB for X (2013), bitcoin company (2014), food delivery startup (2015) etc. you’ll just be chasing a mirage. The successful entrepreneurs are usually the ones who have been focused on this area for years, obsessed with the problem area since long before it was in the spotlight. The ones just there chasing the headlines and tailwinds are quickly weeded out (sometimes not quickly enough).

It’s okay to listen to the top charts, watch the startup news and learn about financings and exits, and read about the titans of business, just make sure you’re using them as inputs into your own kaleidoscope and not trying to chase their exact colors.

When You Don’t Know What To Do in a Competitive Situation, Do Something

We live in a chaotic, interconnected world. Each business has partners, direct competitors, frenemies, and everything in between. When we re-launched Next Big Sound in the summer of 2009 there was one company called Band Metrics that was around. Another one soon launched called Rock Dex. Billboard soon launched a competitor called Billboard Pro. And in the UK there was Buzz Deck and Musicmetric. After 5 years only NBS and Musicmetric remained.

I believe that we were the first company in our peer set to price our product. There was nothing comparable on the market so we decide to introduce a $79 per artist per month price point and experiment from there. Thinking there was some internal logic to the number, one of our competitors also set their price point at the exact same amount when they released their paid-for version.

Two stories, one from chess and one from the cold war, remind me of this principle.

Gary Kasparov was playing chess against the IBM super computer Deep Blue. This computer was capable of calculating millions of chess moves and long sequences of moves and probabilities. During one of the games, the computer made a mistake. Kasparov could not figure out why the computer would make this random move (neither could the IBM technicians).  Kasparov “knew” that a computer wouldn’t just make a random move and there must be some underlying logic that he, the greatest chess grandmaster of the era, was missing. It literally started to drive him to insanity.

Similarly, in the TV show The Americans on FX, the FBI captures a low-ranking KGB officer entirely by accident during a botched operation. The KGB thought there must be some inherent reason for the move and tore their staff up and down trying to figure out what this person knew and why the Americans would want to capture him.

Sometimes, when you don’t know what to do, just do something. With pricing. In a chess game. Or in espionage. The best move might be to make a random move with confidence, and let your competition destroy themselves psychologically.

August 18, 2008: The Day I Quit My Job

This post was originally published on the Techstar's blog: http://www.techstars.com/content/blog/day-i-quit-my-job/

“Hi Ed, I’ve decided to work on my company full time and won’t be starting in NYC on my scheduled start date next month.”

“Sorry to hear that, Alex, we wish you the best of luck on your new music venture. Robyn will send over paperwork and we’ll need you to return the signing bonus.”

Ed was the Chief People Officer of the management consulting firm I was scheduled to join in New York City in September of 2008. I had signed my offer letter in January of 2008, winter of my senior year at Northwestern. I had my NYC roommate figured out, opened a NY bank account, and was so excited to move to New York City, but that was 9 months earlier. That was before I’d taken Troy Henikoff’s entrepreneurship class and started working with David Hoffman and Samir Rayani. Before we’d launched nextbigsound.com, before we’d raised $25k, and before I realized that instead of consulting, business school, more consulting and then starting NBS, we had already started it!

I quit my job, mailed back the $10k signing bonus, and told my friends I wouldn’t be joining them on a summer trip abroad or moving to NYC. David and Samir were starting their senior year at Northwestern. I moved into David’s spare bedroom for a month or two and then downtown with three friends who had just moved in with one another. At this point, Fall/Winter 2008, my task was simple: I needed to raise $150k seed round for a consumer-facing streaming music site as a 22-year-old recent graduate and first time entrepreneur.

Anyone alive during the Fall of 2008 knows what happened next. The economic apocalypse hit; sending the economy into the worst dip since the great depression.

The timing of this recession, right as I was entering the workforce and starting Next Big Sound, has made a deep and lasting impression on me. Like a plant in the desert that adapts to survive on very little water we started our business with a very specific set of environmental conditions and thought it might always be that way. Given my starting reference point - the monster seed rounds of 2010-2015, the seed and A prime-prime-primes, the proliferation of angels, and accelerator explosion was all pretty mind-blowing for me to watch. As if a rainforest has bloomed in the desert. I love what the last 5-6 years have done for entrepreneurship, technology’s impact on the world, and the proliferation of strong startup communities but I’m curious if 2016 will be the year where I’ll get to see what a sustainable temperate climate looks like, in between the desert where we started and the rainforest that roared to life.

Find an Interesting Intersection and Obsess About It

Villages, towns, and cities spring up around intersections; the intersections where bridges, rivers, and roads cross paths. I’ve come to believe that all of the most interesting things happen at the intersection of two other fields.

When thinking about your career I love the thought exercise of finding the intersection of interests that you can see yourself obsessing over for a decade or more. Do you love history, hip-hop, and broadway musicals? Lin-Manuel Miranda is currently enjoying enormous critical and commercial success as the creator of Hamilton. But did you know that he’s been working at this unusual intersection for years? Do you love mobile location and urban exploration? Dennis Crowley is the CEO of Foursquare but his first company, started over 10 years ago, was at the same intersection years before the smartphone was invented. Do you love animation and computers? The Pixar team was working at this intersection for decades until the technology caught up to where they could release their feature-length smash box-office hits.

I think that the most successful people have found and pioneered an area at the intersection of two fields that might never have been combined. Scott Adams, the creator of Dilbert, was one of the earliest ways I identified the above maxim. He thinks he’s in the bottom half of illustrators and bottom half of business people on the planet. But business cartoonists? He’s the best in the world.

I think about my own life - The Wisdom of Crowds changed my world. I’ve been obsessed with collective intelligence ever since. I got approval from my dean at Northwestern to pursue this as my senior thesis.  I even got a chance to tell this to the author, James Surowiecki, when he checked into a flight right before me and we were trapped in the jetway while the plane boarded. I’ve also been obsessed with the music industry for years as an artist, working at a label, and leading the student group in booking $300k+ worth of shows a year in school. It’s no accident that Next Big Sound is a company that exists at the intersection of collective intelligence and the music industry.

“Do what you love.” “Follow your passion.” We’ve all heard this trite career advice. Like all cliches there is truth at the core but I think focusing on intersections might be a more concrete way to find what unique combination of skills, obsession, and excitement you can channel to make your mark the world.

The Perfect Morning

Good morning! Most of us have a strong sense of what we like; the things that put us in a good mood after we wake up, the things that stress us out, and the routines we like to begin our days. But how concretely do people know what comprises their perfect morning and how often does your day start off in an ideal way?

It wasn’t until I saw a Quora post on the topic that I realized that I could write down my perfect morning and try to live it as frequently as possible. We all calibrate our habits on a regular basis I just don’t know why it took me so long to do this explicitly.

My current morning routine for a weekday morning at 29:

Wake up around 6:30 as the sun streams into our bedroom in my NYC apartment on 28th and 2nd. I read the NYTimes on my iPad for half an hour in bed, I also check my personal email and read Delancy Place - a daily excerpt of an interesting, random non-fiction book. I aim to meditate for 5-10 minutes each morning using the Calm app on my phone. Push-ups (using Perfect Pushup h/t Jason Mendelson) and sit-ups if I’m not going to the gym in the afternoon then jump in the shower. Breakfast of yogurt and berries. Quick email check. Make a cortado for myself and write for 20-30 minutes. Walk into the office around 8:30 or 9am to begin my day.

I also have my ideal work day:

Internal meetings with my team in the morning and hopefully a 1-2 hour block of time before noon to really go on offense and accomplish something big on my list. Healthy lunch at my desk. Back to back 30-60 minute external calls or meetings from 1-5pm. An hour or so to catch up on emails, tasks, etc. Gym for an hour then drinks with other founders, music industry people, friends and dinner around 8:30 or 9pm at home or with whoever I was out with after work.

I’ve experimented with all sorts of workday routines and schedules and settled on one that works really well for me at this point in my life and career. I’ve probably been doing this the last four years on weekdays. My weekends are different and were already nicely written up and published (see Inside a CEO’s Weekend).

What is your ideal morning? How do you know if it’s your ideal morning if you never write it down? Why stop just at morning and write out your perfect day? From there the challenge becomes to revisit it periodically, tweak if necessary, and try to live it as much as possible.

If you’re looking for inspiration I highly recommend you check out the book Daily Rituals. I reached out to the author and met him for coffee one of my trips to LA, he has compiled an awesome book of the routines of luminaries throughout history. There is also http://mymorningroutine.com/ for more modern day inspiration.