2% Value: Flick It

during my time between Wheels Up and Wildcard this winter…I took to ideating, writing and proof of concepting a lot. see: Oblige

here’s an idea called Flick It

if you’d like to see a similar product in the wild - check Picture Life. hats off to Nate and the team for building a great app that is saving my butt for the iOS 8 upgrade. 

originally I came to the idea (that’s what it was and still is) after thinking to myself..”hm..what native apple apps on my phone haven’t been replaced yet?” biggies like email, calendar and messaging were obviously taken by a slew of apps. but even the smaller ones too - dark sky for weather, a design focused calculator, wunderlist for notes, castro.fm for podcasting - were all taken by someone who invested the time and energy to make a better and focused experience.

the one that stuck out lying there in my homescreen was Photos. and man, how meh of a product. still meh. it just isn’t that much of a delightful experience (cue this) despite it being a daily use case for millions if not tens of millions.

ultimately, I wanted to brainstorm how one could replace Photos. key themes:

- how could I re-visit a particular photo in the fastest way possible? with photos it’s basically like playing the slots with your thumb if the picture wasn’t taken within the last week. how many scrolls up was that February vacation?

one simple hack to allow for faster navigation was making more recent pictures have larger thumbnails

- enabling faster recall was important and allowed us to surface different contextual data about groups of photos…this is the premise of “insights” group strings of pictures together based upon location and time of day (had a gut feeling that vast majority of photos you show to a friend in-person or share digitally fall into early am sunrise, midday lunch or late night outings)

improve the sharing experience which felt a bit bloated and slow. we wanted to make sharing fun and fast…ie thumb swipesimply swipe the photo to the social service you want. Picture Life actually has this option for social channels and other app actions

- Photos is a bare bones layer on top of your photos to share and edit (would barely say manage). vision was to still be a layer (no web storage/backup) but be a faster and sleeker method of doing what you do several times through out the day

just another opportunity to share janky mock ups. it’s always fun to see what things come to life

believing in the magic

there hasn’t been a day in the past 6 years where I haven’t been thinking about technology and startups. sophomore year of high school, I started blogging (posterous), tweeting and diving into the growing Boston tech scene.

one of my first cold emails was to Nick (formerly Sparkcloud, now Wefunder). the second outreach went to Sean Broderick of Techstars Boston as they were preparing for their second class in Central Sq. that conversation led to a final round interview with Tim Falls (formerly TS Boulder, now Sendgrid)

some funny notes that I distinctly remember from that “early time”
- DartBoston was rolling along steadily
- TS was the only accelerator in town
- Mark Bao was in high school selling websites
- Daniel Bru was blogging for techcrunch
- Boston based Springpad was battling it out with Evernote
- Thesixtyone was a daily music visit
- Gary V’s Wine Library Videos were in full swing
- My first exposure to SXSW was watching Robert Scroble livestream his bar crawl
- SCVNGR was competing with Gowalla and Foursquare

the reason I was so enthralled with tech was how fast things moved and how approachable both the products and people were. as is the case today, building an impactful tech business is largely a factor of speed (execution, getting to market, changing, learning). contrast this to the “knowledge” one was forced to consumer in an academic, albeit rigorous, setting and you can understand why a hyperactive teen would rather go online and explore. most importantly (this truly blew my mind), you could observe and communicate with the actual CEO, co-founder, VP behind the amazing thing you used on a daily basis. i still feel like this is one of magical qualities the industry has.

in the early days I couldn’t get enough of new projects and startups…to this day that largely holds true as well. the thing was, if it was a startup - I was fan. a big one. I wanted to be as an early adopter as one could be. I wanted to support them and spread the word. I wanted to communicate with the team. due to my natural inexperience and bleeding enthusiasm, I frankly couldn’t even take a stab at evaluating the team, product, market, etc. it didn’t matter.

nowawadays, I feel that same enthusiasm fading away ever so slightly. it’s been a bit more difficult to unequivocally praise everyone taking a stab at starting their own thing. you start to realize after reading thousands of articles, meeting dozens of people, watching hundreds of hours of interviews and personally using hundreds of products that not all people and ideas are the same. there are wantrepreneurs, grin fuckers, naive and talented, longtime operators with domain experience, truly talented veterans out there competing…and that list goes on and on.

a friend and I recently were chatting about this situation and how we should process it or take action (if at all). after all, we work in early stage tech and certainly want to be supportive and optimistic.

she had a nice analogy that fit the situation quite well.

she compared it to fitness levels. she asked what would I think if was to I see an overweight person venturing out on a run and I said “fuck yeah, good for them”. “how about a normal or athletic individual?” same thing. “fuck yeah or props or damn, impressive or I should be out there”

the form of the inexperienced runner may be way off. the normal person may be not be properly planning their training routine. the advanced runner may not be not doing enough preventive medicine. who knows.

the point being is that regardless of experience, skill level or motivation - these different and unique groups are out there challenging themselves. they are doing the uncomfortable thing to grow. bottomline is. they were JFDI and that’s the first ingredient on a path to success. [fist bump]

no one knows the future and where these paths may take them. everyone started somewhere and it sometimes it takes the most unlikely of people in the most unlikely circumstances to do something special.

it gave me a refreshed outlook on the next time I come across a first time founder or hear about a veteran looking to go from 0 to 1. go in with helping hands, hopes high and look for the magic.

Power of Groups Brainstorm

Few ideas I’ve been tinkering with and/or thinking about. Common themes: connected and trusted networks, explicit opt-in actions, surfacing value that lies closest to us. 

Collective Brain Trust

Several close friends and I frequently share provoking and substantive personal and professional content. The tool doesn’t really matter (formerly email thread, currently Honey)…it’s the notion that several individuals are looking to grow together and riff on quality ideas. The mental connection, commenting and sharing can (should) happen outside of coffee catch ups or spontaneous gchats. 
I’ve begun to realize there are currently several weaknesses / opportunities to incrementally improve the effectiveness of this. 
- Why are we “limiting” this to 5 friendly tech-focused young males? Not much diversity and chance for radically different viewpoints to shake up your perspective. 
- Chance for loose nodes in each of our network that we connect with personally to grow closer on a consistent basis. Potentially very strong way for individuals to grow closer online…later leverage that rapport for greater offline interactions.
- Encourage greater sharing of bold ideas, themes and stories rather than the regurgitation of short term news. 
- Without people engaged in a format like this, you rely on their explicit share via twitter, quibb…often the vanilla and mundane content that all of us think helps brand us and that our friends/followers want to see…not a great context to share something a bit more raw or embarrassing. Elements of freedom and white space that Secret or Whisper encourage. 
Angles to take. 
- Make it anonymous, there is one curator who invites all 15 individuals but no one can see what content is being shown.
- Information and insights (signals) are highly valued in today’s busy and overwhelming digital age. Would you pay for access to a prominent individuals personal and un filtered Pocket/Instapaper? Who wouldn’t want to get exposed to the feed that thought leaders are using for themselves? 
Digital locker for XYZs brain…curated digital “Quarterly.co
- Allow better linking of accounts amongst a Pocket, Kippt, Instapaper. ie I don’t want to have to take 5 seconds and have 5 thumb presses to send to a particular friend…almost like a Venmo trust feature where both individuals opt-in and want articles from each to show in their own feed.  
Let me know if you are interested in being part of this revamped intimate group, you’ll probably hear from me anyways. :) 
Connected Couches
Apply the Couchsurfing model to a trusted 1st and 2nd degree network. 
Before I moved to NYC two weeks ago, I had to take several trips down to the city. Ultimately the lingering thought I kept having was…”As a relatively connected and outgoing “good guy”, I shouldn’t struggle to find a couch to crash on in a major city.” Same could be said for your 25 best friends and colleagues. Where you’re staying should rarely be a factor for a young and flexible person when planning a serendipitous trip. We’ve all got folks we think we can count on but ultimately travel, health or acts of God can mess things up. Greater “coverage”, exploration and value. 
First version - shared google doc. 
Finding 20-30 close people in my own network and having them get onboard. Then asking each of us to recommend 3 friends across country (2nd degrees) that through the transitive property we would all feel comfortable and happy to hang with. 
Key elements. 
- Explicit opt-in. The friction / awkwardness most of the time comes from wondering if an acquaintance would be open to hosting you for a night. 9/10 your gut is right if you think they’d say hell yeah…though ultimately can circumvent this by having everyone on the directory raise their hand and say I buy into this fun experiment. 
- Keep it light weight. No specific tool is needed, one or two line fundamental rules.
- Allow to grow with approved people. 
Decision Maker 
Couldn’t think of name for this…but general premise: as a sales/bd/outreach guy…why should I have to do the “hard work” of finding needle in the haystack of a large org every single time when that particular VP has already connected with 20+ professionals in parallel industries. 
Yes - rapportive, email hunting, LI browsing, references, luck, etc, etc are all fundamental tools to use in a strong outreach. What they don’t address is what the actual person (esp at corp level) is really responsible for and how you quickly find out who you need to truly be speaking with. 
Why can’t my buddies at SaaS companies working in unrelated markets efficiently team up to share contact info but more importantly intel on what Mr. Smith is accountable for, what metrics his ass is on the line for, what deals he’s been in charge of, personal characteristics, etc ?
Digital BNI Groups 
This may be a bit foreign to most techies, but BNI (Business Network International) is a large international organization that effectively helps local professionals build referral networks in the offline world. Your small town lawyer, real estate agent, life insurance guy, mortgage broker, plumber are probably actively involved. Each chapter has vetted individuals from respective industries…all coming together 1x or 2x a month to share best practices, network and share referrals. 
Seems silly to me in this day in age why there isn’t a digital equivalent in a similar format? Doesn’t have to be as hokey and networky as BNI can be, but where is the outlet for the routing of explicit value and transactional opportunities amongst a trusted group….could especially help within digital professionals where geo doesn’t matter. Moving company guy needs to be within 30 miles but introducing your copywriter to a friend across the country makes sense. Requests or offers for help in the twitter stream often seem to “selfish”, have low visibility, and aren’t necessarily focused on the people that could actually help. 

2% Value: Oblige

As part of a self-guided learning experiment the past few weeks, I spent many late night hours as a maker going through several challenging thought experiments.

The two questions I have on the forefront of my mind. 

1. What is “product sense" and how does it manifest itself?

2. How can a non-technical person develop product sense AND (maybe most importantly) demonstrate that to the best of their ability?

I think it’s quite easy to say, “I’ve got good product sense” or “I know a great experience when I see one”…I used to think those things myself. Sure, you may consistently download the most recent apps and have high level opinions on each but is that truly impactful? It’s a much different story to start with a blank wireframe and try to build an effortless user experience from scratch. Or thoughtfully break down and analyze why your favorite calendar app is what it is. 

In the spirit of making, I’d like to share an idea that I’ve given much thought to in the past week. 


Volunteering needs to be re-defined. Think what charity: water did for the perception and application of charity, especially amongst the millennial generation. 

With a tech enabled experience and bold, authentic brand - Oblige could change how teams, groups and individuals give back. 

Oblige. Do good locally. 

Learn more: Deck + Mockups 



2% —> reasonably fleshed out novel idea. I understand execution, execution and more execution over the longterm is 98% of the venture and the only way to bring something to life.

Hope someone can run with this, no NDA needed. :)

Coincidental timing with LinkedIn launching the volunteer marketplace

Presentation created with Deckset, go check it out.

Product Feedback II

An example of product feedback sent to a member of the Memoir team below. Much of the feedback happened to align with how they were thinking and approaching the next version. A nice back and forth discussion followed afterward. 

Few personal (read: subjective) notes on approaching product feedback.

- Lead in with a note, include link to your digital presence. Demonstrate some rapport through commonality. long time user/interested in the space/mutual friend/etc

- Be humble and upfront that you understand your perspective is one data point. Expert or not, the team is living and breathing the product..they’ve probably thought of many points/ideas/opportunities.  

- Already telling them what they may have considered is helpful though. It can validate a hunch or similar feedback they are gathering to take action on. Dropping new insights is possible but rare. 

-  Try to understand who their user and audience is. Delicate balance between elaborating on your own experience (most likely coming from tech bubble) and who they think is most apt to use the product. 

- Include photos. Makes it much clearer what you are referencing and it engages them. Shows another level of thoughtfulness and care. 



Personal note 

1. During the onboarding process, I like the ability to fill waiting time with video…though I don’t think most users will simply remember Mac app URL. Perhaps on second screen you could simply put a ”remind me via email” button if you’ve got that info via auth. Photo


2. “Sync the photos on your computer” also is a bit confusing to me. Seems like a very utilitarian statement along lines of Dropbox camera upload…am I syncing phone photos / new Memoir photos/memories? Maybe just highlight fact I can access memories (more than just photos) on my PC. Inclusion of screenshot is very clear. Photo


3. I find the initial experience a bit overwhelming. There are potentially 20 things to click, explore, expand. One of the things that made it a bit much was highlighting “7 friends on Memoir” and calling me to take action there. IMO, it would be much more powerful to bring this CTA and feature a bit later after I’ve realized the awesomeness I am dealing with. Certainly know you want growth and sharing but let it feel concrete about what I’ve just spent time and energy downloading. Photo


4. I got a bit confused with the horizontal date/day fixed position. When scrolling it would list previous day though I was viewing 90% of another day on the screen. I think the eye focus is processing the center of the app and not seeing January 8 in memories across the top. Photo


5. The team has probably tested for this but I think a cleaner and faster experience would be to be able to toggle current stream of recent days and last years respective dates. I found it a bit clunky to see the year after follow it on main page. The emotionally and fun contrast can come as soon as I click into the day. I think if someone wanted to re-visit a long ago memory, they would use the calendar look up.


6. The calendar and search look up I think is an area where you guys can really win.
When I click it, I am expecting to see a digital calendar with months/days. That’s fine that I don’t. Instead of seeing recent memories (which I just saw), I think having a clean search bar would be cool. Under that, give me light colored text promoting me to try a variety of searches. 
"Applebees John" —> searches for respective text/check ins
"Feb 8th….February 8th" —> goes to particular day
I think these ways to mentally race back in time are quite powerful and more natural thinking…esp if combined with standard “May 5th 2011 was fun, let’s re-visit that party” 


7. Within Sharing Privately, the selection of parts of the day is a bit tricky. Rarely do users see interfaces (email unsubscribe comes to mind) where “Select All” appears multiple times. My hunch is that the more you try to unbundle the day into check ins and photos, it looses its touch as thematic memory. Did like the Sharing Privately name, as it focus on message rather than medium. Photo


8. I shared a memory with myself to test and didn’t realize the subject line wasn’t the text I put within the app which is ok, bit of a surprise. I wouldn’t include “Ryan Dawidjan shared this with you” on every single item. It feels like I’m transferring data more than I am sharing a beautiful, fun, sad, etc day/memory with them. 
Hope it helps a bit, please let me know candidly! Happy to clarify or provide more context as well.”

Product Feedback

Sending candid and thorough feedback regarding a product experience to a early stage team can be incredibly valuable for both parties. Three reasons why I’ve consistently taken an hour a week to send tech founders a note. 

1. Solid way to gradually hone your own product sense. Constructively think about sign ups, flows, layout and overall experience. Find weak spots and propose potential solutions. 

2. Start to build a relationship with a VP or co-founder. Come bearing gifts through a thoughtful investment of time and energy, leverage digital rapport for meeting next time you’re in their city. 

3. Realize the full potential of the product for your own use case. Discover best ways to streamline your workflow and use the tool/app more effectively. 

An example of product feedback and the best practices to follow

Mentorship Framework

Knowing which veteran and successful individuals you’d like to receive help from in the tech community is rarely a challenge for people genuinely involved. There are numerous ways to identify them, connect and tastefully stay on their radar. From my personal experience and observation of peers, the tricky part is establishing a reliable cadence in your outreach as their time is extremely limited and you maybe unsure if you’ve “earned it” consistently. 

After having a loosely held personal board of advisors for the past two years I decided to try and formally establish three mentor - mentee relationships in Boston. Six months later I can successfully report back that all have gone smoothly and the personal relationship with each has continued to grow stronger.

I’ve included a few notes and a framework below to potentially help those in a similar position. I’d be interested in hearing how others have approached this topic. 

  • I wanted to ensure that there was mutual “buy-in”. ie If an email or call came in, they wouldn’t see it as a nuisance but instead something they had welcomed and expected.
  • The schedule for updates every few months was to get the ball rolling and establish a regular pattern though most of the interaction revolves around unplanned events and opportunities. 
  • I had known the three individuals in a substantive way for at least a year before approaching this topic. I’d caution using the memo below if you are very early into a relationship. 
  • I opted for an email discussion because I was confident they’d quickly say yes in-person but wanted to fully layout the reasoning and context.
  • During calls or sit downs, I always ask about ways to potentially help with their list of priorities before anything else. ie How can I help with intern or junior hire recruiting, connecting with a brand, source a blogging opportunity, product feedback, etc. 
  • Think of ways to provide value in creative ways as well. ex Host a dinner for your mentors together where they can hang out, connect and learn from each other. 


Hi ___

[Personal note]

Would you be interested in serving as an informal advisor/mentor? Happy to chat more about this and actually would love your perspective if this is the best approach to a bit more structured (but flexible) and consistent long term relationship.


The gist is: I’m focused on making larger, more tactical personal and professional advances as the [current job] opportunity becomes larger and more challenging.

Immediate goal:

1. Be able to hire and recruit top talent in cities across the country.

2. Continue to execute and maintain valuable brand partnerships

3. Learn the foundational management skills necessary to manage multiple teams

Long term goal (2-4 years):

1. Start my own venture as a business co-founder who has demonstrated he can sell (build a big sustainable biz), has the network to raise money and skill to recruit a great team.

Format and Why You:

95% of this is learning by doing and learning outside the day to day by reading, interviewing and researching. The three individuals I would like to have serve as informal advisors are people I respect and know personally that have relevant skill sets. Simply there to be share insights, perspective and help with hurdles faced at that moment in time. I’ve seen you raise money, develop strategic longterm plans and build ABC co into a real business with a heavy sales component.

The Ask: A scheduled 30 minutes of time every 3 months to chat via phone. Brief catchup —> questions —> recommendations. This is a private connection, not for personal/public gain.

The Value: Help a young guy rise to the next level. Be able to tap into younger network for junior marketing, biz dev and engineering hires. Have fun sharing.

Getting a Handle on Identity

Hi John,

This is Ryan (@ryandawidjan), I hope you don’t mind me reaching out. [Insert reason and/or commonality]

For the vast majority of personal cold and warm-reference emails that I send, I lead off with this “technique”. The inclusion of the twitter handle is significant for several reasons.

First, it can help immediately trigger past moments of connection between the two of us. favorites/discussions/occasionally seeing the handle in the stream. Second and most importantly, it serves as a fast direct link to what I am doing, what I am thinking about and who I am interacting with. All important signals at a quick glance when someone is deciding to potentially invest their energy and time with you. Third, it shows I’m “a real” person to someone who may have never heard of me. By real, I mean, there are clear signals I’m not a bot or scammer. 

I think one’s online presence is hugely impactful in trying to foster and maintain offline relationships. I have the perspective that my twitter identity is by far the most important tool. I expect and even welcome a potential employer, date or company partner to explore @ryandawidjan. I have nothing to hide there. You can see the content I find fascinating, the types of individuals I follow and talk with. It isn’t a perfectly polished about.me or private Facebook page. It doesn’t serve as a purely promotional locked box. It serves as a consistent window into my mind and actions, things that I believe are substantive opportunities to relate to. 

Don’t underestimate your handle as a well of personal commonality, first impression maker and identity tool. It’s quite hard to fake 16,000 tweets over the course of 1000 days. Your next boss or date may just get excited about the opportunity to meet you.  

What online presences truly serve as an identity for you and when do you reference them?

Spirit of Making

I used to frequently sneak over to the neighboring Olin engineering school for their student “SLAC” (stay late and code) nights. The first few times were incredibly nerve racking as there have always been (and for the most, largely deserved) reservations of inbound visits from non-technical business minded folks. 

Olin students are a special breed and they will be the first to admit it. Often compared to MIT students a few minutes down the road, Olin kids are incredibly smart hackers and engineers with a bit more of a renegade personality. They can’t be pigeon holed as they move effortlessly from on-campus 3D printing machines to user orientated design projects. 

The countless late nights and early mornings I spent with friends like @juliananazare @tcr @wcdolphin and @mchang were incredibly stimulating. The most I could possibly do was to ask foundational questions, provide introductions to navigate the Boston tech scene and crack a few self-deprecating jokes. It was invigorating to be in a culture of creation…”wouldn’t it be interesting to build a script to create thousands of new mobile twitter accounts in a night…and win $3000 from Dharmesh Shah?” Novel/old/crappy/fun idea..it didn’t matter - within hours there would be something up and running to play with. 

In those moments of building I would look on amused, intimidated and curious. To be honest, I never ended up really grasping things like how GIT worked or why people often preferred Rails to Python. I did however learn two important things that have stuck with me along the way. 

The first being that folks like myself can provide meaningful value of varying levels to complement their abilities and that honing these skill sets (product vision, fundraising, BD/growth, etc) is crucial for being a future founder. Second and more importantly, I came away with a deep empathy and appreciation for the work that engineers do. The respect I have for the challenges of bringing something to life humble me and serve as a daily reminder that there are hard working people and teams behind each of the products we use everyday. 

The notion of being a maker and doer has been re-invigorated in me this week as I “develop” a new responsive personal website (go Webflow), witness @hijonathan launch his new venture and release a simple app with @zmh

We can only be excited by the thought of future tools and services to come that will allow both talented engineers and creative laymen the freedom to bring ideas to life. 

It’s fun to get in the game.

Control the Controllable

As cliche as it is to say, the roller coaster of emotions is quite real. One day you may be all smiles pumping landing a new partner dreaming big and the next week your decision maker at the brand happens to leave. Start the weeks of selling, evangelism and rapport making all over again..

The thing I’ve found best to combat the daily grind is to try and control what I directly impact..that being my mental, physical and “social” health. I consistently have long (and hopefully impactful) days with work being the core focus of my day..it’s what I derive most enjoyment (and pressure) from. 

Going to the gym at least once a day, checking in with a friend, following a particular diet and clearing my mind with some light reading are all strict habits now. Each obviously has a great list of benefits associated with it but the most important common theme is that it gives you a sense as well as actual control of your day. Whether things are going well or downhill for a variety of reasons with BL that may be even outside my actions, I know I can influence my fitness routine, mindfulness and happiness to a large extent. 

Too many young folks in this industry believe they need to strap every aspect of their life onto a high turbulent ride. Sacrifice is key, just invest in the right areas. 

Get fit, get fitted. 

Happy to discuss and learn more - @ryandawidjan

Snagged this one. 

Put This On Handkerchiefs
A few months ago, one of the most significant shirting shops in New York City closed. It sold only to the trade, and specialized in the finest cottons from England and Italy. They had to sell off their stock - decades of beautiful shirting fabrics.
Luckily, we got in on the action. We had the folks at the shop ship us a box of their finest stuff - all in lengths too short to make into shirts. Perfect, of course, for pocket squares.
The result is a limited-edition handkerchief collection. These pieces are made from the best cotton in the world and are hand-made, with hand-rolled edges, just like our other Put This On pocket squares, but they’re priced so inexpensively that you can use them to blow your nose if you want to. The squares are just $35 each, three for $95, or five for $125… but when they’re gone, they’re gone.
You can see the full selection here in our Etsy shop. Pick up a drawerful!

Snagged this one. 


Put This On Handkerchiefs

A few months ago, one of the most significant shirting shops in New York City closed. It sold only to the trade, and specialized in the finest cottons from England and Italy. They had to sell off their stock - decades of beautiful shirting fabrics.

Luckily, we got in on the action. We had the folks at the shop ship us a box of their finest stuff - all in lengths too short to make into shirts. Perfect, of course, for pocket squares.

The result is a limited-edition handkerchief collection. These pieces are made from the best cotton in the world and are hand-made, with hand-rolled edges, just like our other Put This On pocket squares, but they’re priced so inexpensively that you can use them to blow your nose if you want to. The squares are just $35 each, three for $95, or five for $125… but when they’re gone, they’re gone.

You can see the full selection here in our Etsy shop. Pick up a drawerful!

It’s Not What You’re Leaving, It’s What You’re Leaving For

[Originally composed May 28th, 2013…guess I’ve been busy]

Now in Chicago launching our offline presence, hiring a team, and ensuring more gents can receive a remarkable menswear experience. 


"But there is also something to finishing something you started." - Fred Wilson, sharing his personal perspective on his daughter’s well earned college graduation. 

I adamantly believe this statement to be largely true and that’s why a few months ago I mentioned that I had firmly attached myself to the focus on true impact. "Intense Focus on Results"

The long story short though: I won’t be finishing school. 

April was a month of considerable change. Within a few weeks, I had been in a car accident, gotten out of a relationship, ended my college lacrosse career, moved to a new spot in Cambridge, help execute Blank Label’s largest BD deal to date and take a leave of absence from school. 

A mentor of mine gave me this bit of perspective as I was considering leaving school to work full time at BL. “It’s not what you’re leaving, it’s what you’re leaving for.” While at the time it seemed like general high level advice, it actually was quite important in helping me frame the trade off I’ve decided to make. Regardless of the structure/path, you should opt for the one with greater personal and professional upside. 

Personally, I had felt for a longtime that the “check boxes” of college had been marked off. learn to live independently, find an area of interest, learn how to network, experience the social life, connect with professors, find about your drive/wants/needs in life, be exposed to a lot of interesting people and places, etc.

Having largely done all that within high school and the first year of college, I was open to exploring non-traditional paths to satisfy my professional interests. The “problem” was, I didn’t have an opportunity that was meaningful enough at the time to pursue. The summer before school I had done a lot of thinking about taking a gap year, even sounding it out with Seth Godin and Ben Casnocha. Then, the summer of my freshmen year I had considered taking time off to learn under Brent Grinna and the small crew at EverTrue who are now on a roll.

All in all though, these weren’t the right opportunities that were right for a significant (2-4yrs) time commitment. It was a bit early to making that call and I didn’t think I could find a high impact role for the organization. I’ve now found one and I’m more than excited to execute on it. 

I will be continuing to lead up our national partnership and offline showroom efforts as we raise money and grow as a team in different cities across the country trying to make custom the new standard for the urban professional. 

My friendship with Fan goes back at least three years now. I first tweeted with him when I was in high school in January of 2010 with an idea for the then just launched Blank Label. That summer when he was in Shanghai setting up manufacturing we had a skype call about a community manager position. 

Fast forward three years and we’ve been good friends that bond over basketball, menswear and trying to learn from the best in business. For the past year I’ve been working part time at BL while trying to balance four classes, lacrosse and Rough Draft involvement. Let’s just say between physical/mental drain from context switching, it’s incredibly frustrating not to be able to focus 100% when that one thing you really want is in from of you. 

I will join now a few close friends that have stopped their traditional path to higher education to try and become meaningfully different. There a few common themes from all our decisions but here are mine personally. 

- Optimize for the rate of learning. Yes, in almost any context you will be learning something (classroom, apprenticeship, internship, etc) but you should focus on finding that path that excites you the most because you’re being challenged, potentially failing and accelerating your rate of development. For the most part, doing entrepreneurial things > studying entrepreneurship. 

- Surround yourself with smart and driven people…whether it’s roommates or colleagues. 

- Work intensely on the things that you enjoy and couldn’t care less if you didn’t get paid or public recognition for.

- Be confident that your story you can tell in two years after failure or four years after a success will be much more interesting, rich and relevant to where you want to go.

- Acknowledge the fact that the individuals I want to mentor/be mentored by or hire/be hired by will not be ones putting much weight into the fact that I didn’t jump through small hoops for four consecutive years to get a high cost ($$, opportunity cost) piece of paper. 

- Be in a city with a peer group that will allow you to fully enjoy life, explore new activities and be an interesting person. 

Finishing is certainly a hard thing to do and I do think for the vast majority of folks, it’s still the right decision. I just know that for an ever increasing number of young intelligent and driven people who want to have an impact, it’s a harder but necessary decision to find and continue down the unique path that allows them to level up with their own ambitions. 

Summer and life has begun. Get fit and get fitted,


I Had a Craving..

I had a craving to buy something. A tie, pair of socks, new leather belt…something. A menswear piece that I truly liked and would wear this fall.

After a long few weeks of grinding here in Chicago, I thought it would a nice personal treat. 

I never did end up fulfilling that craving which came earlier this week. It was only as a result of not finding something that stuck - a piece that would have to be interesting enough to rationalize an impulse buy.

In a stupid and irrational kind of way, I sort of felt frustrated…my mind and wallet were ready to pull the trigger but I couldn’t satisfy it. Well, this feeling of consumerism didn’t last long and rightfully shouldn’t have. 

This morning after an early morning workout I headed to the local coffee shop to read. And there I found a man who also a had a craving but his craving was much different from mine.

It was for spare change..a snack..a drink. A homeless gentleman sitting on a black milk crate holding a sign leaning against a light post. His craving just few feet from me but a whole world away. 

There in that moment our two bubbles collided, forcing me to mentally slap myself in the face. 

I hope the man enjoyed his grande blonde with two squeezes of hazelnut and vanilla that I grabbed for him as much as I enjoyed forgetting about my previous 1st world problem. 

#5sentences Recruiting

Finding excellent new team members is a hard task and it’s one Fan and I are currently focused on for our city expansions. We can find these folks online and have really started to learn what to look for. The more challenging part is having the opportunity to meaningfully engage with them and then at that point when you do get coffee, selling them on the mission and future of BL.

These latter parts can’t be learned in a blog post nor by listening to a successful serial entrepreneur. Sure, you can read material to try and reduce the stuff you don’t know you don’t know. Ultimately though, you’ve got to hone in on it yourself and do it with dozens if not hundreds of times with real candidates. You may slip up even with a really qualified applicant sitting across from you. The problem for us is that our first 100 times comes in our first venture…we’re learning on our own dime.

Earn the Right to Invest Yourself

A large part of self improvement is taking the time, energy and money to better your health, quality of life, confidence, etc.

The journey towards being fit, well dressed, funny, well spoken, (insert positive skill) is almost always a long one. It requires hard work and sacrifice for results that usually aren’t apparent in the immediate future.

I think the area most people could improve on in respect to beginning and following that interest is really gauging if they truly do want what they’re going after. Ie Am I working out for purely vanity, will I show up to workout even if I can’t attend a group class, does everyone have to know I’ve been hitting the gym (check ins..), do I push myself when I’m there?

I believe once you 100% know in your own mind that you will go and do this thing whether no one knew or even it was a challenge, then you’ve earned the right to double down and invest in yourself. #thisiswhywecanhavenicethings

Committed to exercising 5x/week no matter the family, work, or personal challenges? Great. Go to a nicer gym that has more relevant classes or nicer amenities.

Taken and edited hundreds of iPhone photos, read a few books, gotten feedback from folks more talented? Cool. Now you may be ready for a DSLR and a nice minimalist tumblr page.

Read about brands and product reviews, took hours to finding “your look” and planning your wardrobe. Nice. Treat yourself and invest in some quality (maybe more expensive) casual and work wear.

I now spend $130/mo on a gym in Chicago. I have absolutely no second thoughts about it despite the fact most people at first glance would gasp at that. It’s convenient to work, has a lot of great networking and most importantly, I’m there 8x/week for basketball, lifting and classes.

I happen to bike there every morning. I ride on a 15yr old road bike from a yard sale. I know in my heart I don’t deserve nor enjoy biking enough to actually ride something with smooth gears and good brakes.

Determine the things that will bring you the greatest ongoing daily joy. Gauge your commitment. Double down when you’ve internalized the path ahead. Have fun.