The forgotten joy of iPod Shuffle

As you all know, I have been on a bit of cleaning binge — I am getting rid of many things to put space back into my “living space.” It has been quite an effort — sometimes emotional, sometimes a reminder of my own lack of clarity before buying things. With rains descending on San Francisco this weekend, I stayed at home and essentially purged, purged and purged some more.

And as I cleaned out my desks — between too many rollerball refills, ink cartridges and what not, I found this iPod Shuffle! On a lark, I plugged in my headphones and just like that, the songs flowed in my ears. I absolutely was taken back to a moment in time when this went everywhere with me. The best part was the discovery of these Incase Headphones – they are absolutely gorgeous and sound fantastic. Well made and probably one of the best designed headphones of their time, I find it strange that uglier, lesser brands succeeded in selling more headphones than this minimalists’ dream.

But back to iPod Shuffle — this diminutive little thing is one of my favorite Apple gadgets — simple, elegant, and minimal. One simple cable to charge the device — that’s it. It allowed the machine to do just enough. It forced me to be selective about the songs I put on the device. These days it is all about the iPhone 6+ and everything big, but to me it was during the iPod era that Apple pushed the design boundaries and changed our expectations around product design, especially in tech products. iPod collateral, iPod commercials, and the then Apple store displays were innovative — so much so that companies such as Tile are still copying them.

About ten years ago, I remember writing this piece, iShuffle Principle about curating one’s life and focusing on few and the best. By 2012, I had made progress but wasn’t able to get rid of all the trappings — furniture and fixtures that only distract. While I tried and failed to live with that philosophy, I was not completely successful and fell off the wagon. Suddenly, there are too many notebooks, books and other stuff which I don’t really need. There are gadgets that have become redundant. A television that hasn’t been turned on for nearly six months. And as a result I am once again back to purging and thus reducing my ownership of things.

The iPod Shuffle appears, ever so often to remind me of my failures to live by the iShuffle Principle. It reminds me, while I try, try and try, in the end the sway of advertising and marketing subconsciously leads me to accumulate more. So it is back to trying one more time, yet another attempt to cleanse and restart!


What to read this weekend

It has been a rather crazy and hectic week. I have struggled to find time to read. Usually I distill about 100 articles to roughly 10 — but this week, half my Pocket went unread. I hope to be more efficient next week. In the interim, enjoy these gems.  Have a great weekend everyone! 

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A Storehouse moment!

Seven years is a longtime in technology — both from a technological and business perspective. Technologies become redundant, behaviors are reinvented and new ideas coming at you like bugs flying into the headlights of a car speeding through the night. And perhaps that is why I am amazed that The Crunchies (which were started as a way to celebrate the startups by a loose affiliation of technology blogs) have lasted this long. Gigaom ended its affiliation with the awards earlier this year, though I have always had a soft spot for the award ceremonies, mostly for sentimental reasons. The first Crunchies was my first public appearance three weeks after my heart attack. It was not easy to go onstage at the first Crunchies, but it made me feel normal and alive!

And yet, yesterday, I felt woefully out of place, amazed that as a collective, we sat through TJ Miller’s schtick. I hope I don’t have to endure his inanities again. HBO’s John Oliver was very funny last year and yet he never crossed that invisible line where funny becomes just straight up rude and unfunny.

For reasons that are well articulated by Twitter’s Katie Stanton, whose values I respect and share, we can’t really afford an evening like yesterday. Silicon Valley/Tech is the focus of attention and scrutiny like never before and we need to remember that what we say and do has ripple and impact. As a group, we need to be not only cautious and thoughtful in what we say, but also what we do and who we applaud. I am not against satire or comedy — but there are some lines that shouldn’t be crossed.

As the evening went on, I went on stage with Michael Arrington (who started Techcrunch) to give the CEO of the Year award — to Marc Benioff, who 16 years ago started Salesforce.com and has been at it since. And while he has done a good job as leader of Salesforce, Benioff’s philanthropy is what makes him stand apart. I have had an opportunity to work with UCSF and I have come learn about how much they need in terms of resources and I can certainly appreciate Benioff’s largesse. He has been a positive influence on me from giving back to the hospital that saved me from saying the final goodnight!

If it was fun to be up there, but the biggest thrill for me was to see some of my entrepreneurial peers being celebrated. Matthew Prince from Cloudflare isn’t exactly a household name, and to see him up there was fun. Still, my face beamed with pride when two companies about whom I am utterly and completely biased were recognized for their work — Storehouse and Slack. I say biased because I have a financial stake in their success as an investor in both those companies.


Storehouse, a visual story telling platform co-founded by Mark Kawano and Tim Donnelly, won the best mobile app of the year. It launched a year ago and this wasn’t the first award they’ve gotten for their amazing platform, but continued recognition for a good and thoughtful product. That thoughtfulness comes every time I spend time talking to them about new features and their ideas. It is always — how are we making it better for storytellers! It is an old fashion Apple way of thinking — and I guess Mark who worked there learned a few things. Congrats, Mark and Tim. (Here is, what else, a little Storehouse story about the night at the Crunchies.)

I was also delighted that Slack‘s Stewart Butterfield and his co-founders, Eric Costello, Cal Henderson and Serguei Mourachov won the Founders of the year Crunchie. Those four have had a crazy year, both of growth and valuations, but I love that they are still really four hippies at heart. Stewart & Co and I are old friends (where in I put the old in that relationship) from his days at Flickr. It is good to see them being recognized for staying true to their core selves. Well done gents!

As night turned into dawn, I lay awake thinking about how everything has changed, including (and especially) me — especially since leaving my old profession and embracing my new life at True Ventures. What used to be and what is, are entirely different. As writer/historian Doris Goodwin once said, “The past is not simply the past, but a prism through which the subject filters his own changing self-image.”

February 6, 2015
San Francisco


When brands disappoint…

This rambling piece will (and should) fall under the category of #thingsyoulearnrandomly. And hopefully you will soon see, why!

Every morning, instead of reading newspapers, now I need curated emails and twitter lists. One of these early morning reads is Jason Hirschorn’s Fashion Redef email newsletter — I like fashion and style and it has an eclectic mix of links. This morning, email’s curator Adam Wray shared an article about the rise of the niche and non-mass market brands in perfume industry.

The Globe & Mail’s Nathalie Atkinson informed me that large companies are buying up smaller, independent brands and plugging them into their system. One of them, Le Labo, has been a favorite of mine, had been acquried by Estée Lauder , the cosmetics giant that owns some of the more iconic perfumes in the world. I have been a Le Labo customer for a long time — they make a specific fragrance that reminds me of the Mughal Gardens in Delhi. It is a cherished memory and hence that le Labo fragrance has become part of my daily life.

I was introduced to Le Labo by a friend, who like me is a champion of the small brands. Like her, I too actively try and avoid stuff that comes out of brand conglomerates in general (and LVMH in particular.) My desire is to spend money with smaller companies and artisans who actually benefit for their hard work. The large brand conglomerates are increasingly short on quality and charge a premium for advertising in those big fashion magazines. It is why I am constantly on the quest for newer talents — perhaps that also explains why I find startups fun to follow and champion. It must be that underdog thing. Google was great to root for when it was an academic paper called PageRank — today not so much.

Going back to Atkinson’s piece, when reading that piece, I felt a sense of distress, and a little bit of anger. Still, when thinking about this morning’s feeling, I was confused by my own reaction. Just as I am always delighted by the success of my friends who start companies in Silicon Valley, I am equally happy for Roschi and Penot especially as they stand to gain handsomely from the transaction. So why now was I feeling a sense of betrayal? Was it because the words the Le Labo founders used to state their mission and their eventual actions didn’t match up?

Edouard Roschi and Fabrice Penot, both left L’Oreal to start Le Labo. In an interview with a perfume-loving blogger, Penot once said, “Le Labo does not respond to anything, we just keep on doing what we know best, contributing to the well-being of our clients through our craft, fine perfumery, through true and honest humane connections with them.” Their inability to be honest about their connection to a large conglomerate doesn’t really reflect when Penot had asserted in that interview. If they truly believed the relationship they had with their clients then why didn’t they have the decency to write a small email announcing that it had been acquired by a larger brand. I wonder if they want to hide the fact that they are part of a larger company. After all that would take away the “authenticity” and the image of an “independent” brand.

As is the case, when something fosters a strong emotional and uncharacteristic reaction, I go into self reflective mode. My friends call it my frowning brow, tense face mode. My only explanation so far is that when forming a bond with brands, I am essentially letting them reflect my “self” through their products. Le Labo, then was a small, independent, upstart that made high quality products. It was an apt reflection of some of my values, except in a fragrance bottle. I felt it when I visited one of their many stores around the world. It was reflected in personalized packaging and it was reflected in their ethos.

So perhaps that is why this lack of transparency in their communication with their clients, Le Labo as a brand was suddenly at odds with my way of thinking — and hence why I experienced my unsettled emotions. I am reminded something Starbucks founder Howard Schultz said in an interview with CNN: Great companies that build an enduring brand have an emotional relationship with customers that has no barrier. And that emotional relationship is on the most important characteristic, which is trust.” This broken trust was the reason behind my anger and disappointment with a product that I till this morning, truly loved.

Having being around startups and their eventual acquisitions by large companies, I know that innocence is the first thing to go when part of a giant machine. Their obeisance to a larger profit motive and the quarterly results is what leads to defraying of relationship between us and the brands we love. It is why startups go from beloved to something to be wistful about. Skype, was one of those companies. Today it’s a sigh-inducing necessity. As profits become the sole driving factor, the beloved brands start to make some spreadsheet decisions — raise prices, flood the market, use lower quality ingredients. Who is to stop these changes from happening — the founders report to someone who is a career bureaucrat, motivated in many cases by their annual bonus and desire to not lose their job. Mediocrity is the unseen virus of a large corporation, thanks to the very basic fears of very people who make up a company.

February 5, 2015
San Francisco

Updated on February 9th: The fountain pen world is in an uproar as the new owners of Esterbrook, a vintage and much beloved brand have been playing loose and easy with the brand values. Pen-expert/blogger Leigh Reyes writes about the kerfuffle, which actually is very useful as a “what not to do with your brand.” guide.

Microsoft’s mobile inabilities 


Microsoft has acquired two iOS applications — Acompli (email) and Sunrise* (calendar) — for about $300 million. Those acquisitions are good for the founders (and their investors). Some might see it as a sign of a new Microsoft — aggressive and quick in trying to turnover a new leaf. To me, they are all of that, but more importantly indicative of the much deeper cultural rot facing Microsoft and its now not so new chief executive, Satya Nadella.

“He’s hit all the low-hanging fruit — that said, these things were not easy to do — but now he has to address all the long-term issues,” Brad Silverberg, a former Microsoft executive-turned-venture capitalist told Bloomberg Business in an interview. Spot on — and these two acquisitions are just a perfect example of these long term challenges.

It is a pretty damning indictment that Microsoft had to spend hundreds of millions on front end apps for its own platform –Microsoft Exchange — and it should send alarm bells ringing. Exchange is something Microsoft understands better than most and it should in theory be able to develop good apps as front end for it. And yet, it has to go seeking help elsewhere. Mind you, this is not some new technology and neither it it a new market (like Minecraft) focused on a new demographic. In the mobile OS sweepstakes, Microsoft has been left eating dust by iOS and Android.

If Yahoo’s birdshot like acquisitions and lack of product direction indicate a company struggling to find a toehold in the ever shifting attention game at an institutional level; then these two acquisitions point to Microsoft’s institutional unease & discomfort with mobile and how it intersects with people. Just as Yahoo’s shopping spree isn’t going to fix its cultural challenges, buying companies won’t make a believer out of Microsoft’s rank-and-file. If they were believers, by now Microsoft would have more to show for its efforts. So, in the end, Microsoft might find a very strong toehold in the cloud, but gathering clouds over its mobile future are decidedly dark.

* Microsoft is rumored to have acquired Sunrise.

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