A few months before my 16th birthday, my mom wrote the below letter to Rick Reilly. I found it in my parents’ basement this past weekend alongside a One Headlight CD single from The Wallflowers. It’s a quick read:

If you don't ask, you don't get. Thoughtful.

Before Deadspin, before Grantland, there was the back page of Sports Illustrated. Rick Reilly wrote that back page in the late ’90s. In high school and college, my friends and I would rip those Reilly articles out, tape them to our walls, and get our sports commentary fix. Our brains were still forming, we appreciated puns, quick wit, and pop culture references- Reilly had a flair for the aforementioned trio.

Fast forward twenty years, we’ve got our Chrome bookmarks and Twitter favorites, and don’t much need scissors and Scotch tape to preserve our favorite articles. Now, HBO’s Bill Simmons is the sports journalist du jour, combining pop culture references with commentary on the games that to many of us, are embarrassingly more than just a game. But before Simmons, it was Reilly. He ruled the sportswriting scene.

My mom secretly wrote to Reilly, asking him to send me a few words of advice. I was interested at the time in becoming a sports journalist or a sports agent. How thoughtful of her:

“Yeah, he’d be happy with tickets to see the Metrostars, or a gift certificate to the Gap, but I just kept thinking how much your words on the back page of Sports Illustrated meant to him. And it hit me. What if I could get Rick Reilly to email him some words of advice about looking ahead, pursuing his dream?”

A few months later, Reilly wrote back. Well, he didn’t write back to her. He wrote to me. In the meantime, I probably did get that gift card to the Gap, but you can imagine the surprise when I received the letter below:


To me, that’s Reilly’s best ever work.

It’s not Mother’s Day today but why wait for Mother’s Day to expose such a hidden gem from my parents’ basement.

I’m really glad I found those two letters this weekend. My mom’s – a reminder of such a thoughtful move, and Reilly’s, a positive reaction to said thoughtfulness. It’s something that makes sense. If you’re thoughtful, and sincere, you can often make others happy, and use that thoughtfulness and sincerity for good.

Sometimes it’s nice to take a step back, take a deep breath, and realize that these are the types of people you want to surround yourself with. In business and in life.

Be patient, opportunities will come

Gmail screenshot circa 2005

My apartment search in 2005 in Tel Aviv was conducted primarily on the aptly named homeless.co.il- Israel’s top destination site at the time to find housing. Craigslist Tel Aviv was available, but the user adoption just didn’t exist. I eventually found a great place, but not before my patience was tested after a series of potential roommate interviews and apartment visits. Patience and perspective, at the age of 22, weren’t my strongest suits, even if perseverance was. My dad sent me the note above after another prospective living situation fell by the wayside.

“Remember the old saying about the bus, the house and the girlfriend? Never run after the one you see now, there’s always another one around the corner…”

It’s advice that’s just as valuable a decade later. I’ve improved a little bit when it comes to patience over the past few years. As much as we believe the first option is the best option, or as much as we look forward to willing our way to that next opportunity, there are often many paths towards happiness and success. The best poker players don’t play every hand that comes their way, they fold 75%+ of the time pre-flop. There’s always another pocket pair around the corner. And it’s not just poker, or a house or apartment search, the advice is ever-so-applicable to the fledgling startup too.

LA’s colorful seed stage investor Paige Craig wrote about his missed bus ride just this past week – missing out on investing in Airbnb back in 2008. It was an honest, open look at a missed bus ride. But these missed opportunities often lead to a tremendous amount of learning. Craig said, “After getting the cold shoulder, I realized I needed to go out and build some valuable knowledge, needed a more robust network, and needed to craft my own brand as an investor.” He’s since gone on to invest in Lyft, Plated, Zenpayroll, and other growing businesses. An internal recalibration can emerge from missing the bus.

A missed opportunity, a missed bus, allows you to refine your approach and be honest with yourself – what caused you to be late? How did that one get away? It’s worth asking for feedback, when applicable, in these situations. Missed buying the house? Ask your realtor what components of your offer (down payment percentage, appraisal contingencies, time to close, etc.) you must improve.

Lost out on renewing one of your largest SaaS subscription customers? Put in place an exit survey – a mechanism for you to gather feedback and better understand why your former client is canceling and moving on. You’ll be able to take that data, look within yourself, and make adjustments, as Craig did, to catch that next bus just around the corner.

The subject, on the left, and the author, on the right, both peaked from a footballing and fashion sense in the late '80s. [Klinsmann photo credit to Herbert Rudel]

The subject, on the left, and the author, both peaked from a footballing and fashion sense in the 1980’s. [Klinsmann photo credit to Herbert Rudel]

I like Jürgen Klinsmann, the Head Coach of the U.S. Men’s National Team, a lot. We have much in common. He’s a World Cup winner who flies helicopters, wore short shorts in the 1980’s and lives in Los Angeles. I also wore short shorts in the 1980’s and live in LA.

I recently met Klinsmann and asked him why the U.S. hasn’t produced any world class players. Our footballing equivalent of a “unicorn,” in startup nomenclature, as Aileen Lee of Cowboy Ventures coined back in 2013.

And his answer wasn’t the one you’d expect – the one you hear from casual sports fans: “Our best athletes choose American football or basketball,” or even hardcore soccer supporters, “the youth academies and infrastructure in the U.S. aren’t in place to compete with the factories producing talent in Europe or South America…”

Klinsmann’s answer was entirely different. He focused on one concept and one concept only: accountability. “There needs to be more accountability in the United States, and only then will we be able to produce world class players. At Inter, if we lost 5-0 in a derby to AC Milan, we couldn’t leave our flats for three or four days. We would be confronted at the baker, the butcher, the grocery store. If the Galaxy lost 5-0, Landon Donovan could go to Whole Foods in Manhattan Beach the next morning and no one will recognize him.”

Whether or not he knows where Donovan ate lunch after a big loss, Klinsmann’s point is vital. “When soccer players in the U.S. are criticized, held accountable, or even recognized as much as the other major sports in the country – then they’ll have that drive and an understanding to improve and reach those higher levels,” he said. Unicorn status. World class status. Without accountability, there is little drive or incentive to be great. People are a product of their environments.

The same is true when building a business. Managing a team. Or in entrepreneur turned VC (and SaaS legend) Jason Lemkin’s case, investing in a company.

Accountability improves your overall level. If you are constantly measuring yourself and accountable to someone – or a group, you will produce better. In Lemkin’s case, it’s a Founder or CEO being accountable to a board.

For a startup executive, accountability is key, especially today. I think Klinsmann would likely agree with this Harvard Business Review look on accountability:

“The youngest members of the workforce, especially in the US, have grown up in a sheltered environment; they expect praise and recognition and can be indignant when it is not forthcoming. They are not particularly open to critical feedback. No surprise, then, that at a time when talent retention and engaging employees is de rigueur we get silly advice to management such as, “don’t give employees a hard time about their weaknesses, celebrate their strengths.””

It’s OK to give people a hard time, as long as you also praise them for a job well done. If you’re constantly measuring things and accountable to someone, you will produce better, and more often than not, you won’t need to give anyone a hard time.

40% of America’s workforce will be freelancers and temps by 2020. We’ll be managing more and more people who are telecommuting, freelancing, consulting, and just logging in from faster and faster internet connections at more and more expensive local coffee shops. If we instill accountability now, it will be much easier to maintain it even if our interactions are less and less physical, and more and more virtual moving forward. I’ve seen quite a few startups struggle with scaling a virtual workforce when accountability (and proper communication) isn’t in place.

To be successful, and create those next unicorns, accountability is a must. Tools like Trello are tremendous – teammates can create virtual ‘boards’ and ‘cards’ to see the progress being made on work projects in a collaborative, real-time environment. There is no place to hide. That transparency feeds into the importance of accountability.

Many startups have mastered accountability within product development – specifically through agile development. Our Scrum Masters keep us accountable. Our priority lists keep us accountable. We meet on a week to week basis and assess the progress we’ve made. It’s formulaic, transparent, and collaborative. That’s great.

I think, outside of ruthless prioritization, the key to scaling a startup starts and ends with accountability. People stay on track by keeping others on track. Feeling that pressure can bring the best out of many entrepreneurs and startup employees in general.

I’m not certain that the next Messi will come from Livingston, New Jersey or Los Angeles, California. After all, achieving world-class or unicorn status is by definition, so rare, that the next Messi may not be American, he may be Swedish or Ghanaian. But that six year-old in the San Fernando Valley, running around with his AYSO team right now on this Saturday afternoon sure has a better shot to achieve greatness with a bit of accountability. A bit of extra pressure.

Who knows, maybe we’ll even recognize him at the Whole Foods in Manhattan Beach one day.

notes from dog walker, honesty, communication, trust

My honest dog walker likes Ginger Ale.

I found my dog walker April on Nextdoor. A few months later, the billboards lining Ventura Boulevard in LA’s San Fernando Valley began displaying ads for new dog-walking mobile apps like Zingy and Wag, but by then I was already covered thanks to my modern day e-mail listserv. Nextdoor is one of those hidden gems on the internet, that if used properly can provide substantial value. In addition to my (tremendous) dog walker, I’ve found recommendations for a reliable plumber, painter, and learned quite a bit about what goes on in my neighborhood. The site is far from perfect, it’s user base lacks perhaps, how could we call it, a sense of social media expertise, awareness or etiquette that a digital native may possess, but then again you’re never left confused by a sequence of emojis you don’t understand. The Venn diagram for Nextdoor users and Snapchat users would probably look something like this…

Snapchat Nextdoor Venn Diagram

Nextdoor’s structure provides the ability to interact with a tight-knight, private community but most importantly it truly enables authenticity and honesty. It’s the modern equivalent of shooting the shit with your neighbor at the end of your driveway, in your robe, picking up the New York Times on a Sunday morning. You get the honest recommendation. The peer review. A social Yelp without (most of) the bullshit. But it’s not Nextdoor that got me thinking about honesty and openness this morning (whilst keeping one eye glued to the TV watching the ageless Roger Federer fall short at Wimbledon), it’s my dog walker April.

April leaves us a note every day. That’s part of the job description, surely. Notes from dog walkers are essentially the startup’s version of the weekly product rollout email, or the quarterly Founder/CEO investor updates. It keeps us in the loop. But in April’s note above, she didn’t just perform her daily duty, she went above and beyond: “I stole a ginger ale. It’s so hot and it looked so good.”

And it got me thinking about honesty.

The internet is a place where honesty and authenticity so often win out. You can rarely pull a fast one around here. Someone on Twitter or Reddit will sniff out the bullshit, the lie. A Wikipedia editor will religiously scroll through a page’s revision history to make sure it’s kosher. There is a sense of nobility in keeping it real. Sure, there is still space to hide behind avatars, or operate superb pseudonyms such as Startup L. Jackson’s, but overall the pendulum online swings towards honesty and openness.

So I began to wonder if we’re lagging a bit in the startup world when it comes to that same honesty within our organizations that we’re displaying on the public web.

Honesty is vital within any organization and great for culture. There are many things to be honest about:

  • Giving credit where it’s due. Managers – give credit to your team. Why present a document beginning with “I put this together,” when you can instead say “our team put this together,” or “we put this together,” or even better, “Yoni took the lead on this one.” A little shout-out goes a long way. You’re already the boss, do you think we don’t know that you know how to work Google Docs?
  • Be honest with your co-founders / management team. If you can’t be honest with your co-founders, partners, or fellow management team members, you really should reconsider who you’re coming to work with every day. It’s very difficult to build things that are valuable, so keep it real with those who count on you the most, and who you count on the most.
  • Be inclusive, not exclusive. Being inclusive goes a long way for culture. People just love being included. The reason leaders often exclude others is due to perceived lack of efficiency. “It will slow us down.” Often times, it actually won’t. You may be nervous that if you include that one department or that other department in your process, somehow the project will slow down. But the less honesty and inclusiveness, the more people will get frustrated with you – which will actually slow you down more in the long run (and perhaps create resentment). Most of the time, your colleagues don’t even want to participate in the content of the discussion, they just want to be included.

Honesty shows you respect your peers.

Externally, entrepreneurs aren’t going to change. At the conference when we run into a former colleague or partner we haven’t seen in a while, we’ll still say, “we’re crushing it,” and “growing like crazy!” Fair enough. We’re optimists by nature and it’s smart to sell our momentum externally for a variety of reasons. But behind closed doors, it’s better to let your sales team in on the fact that the site is currently a bit unstable, and that you’re dedicating your focus to improving the infrastructure. Sure, the site may go up and down, but if they know ahead of time from you, that’s much better than receiving an email every month asking why the site is down. Be proactive, not reactive. Which is essentially being honest.

This isn’t a call for CEO’s to release employee option pool breakdowns, it’s just a friendly reminder for those same leaders and department/division heads to recognize the value of honesty on a day to day tactical basis. Your culture will improve through inclusion.

So let’s get back to April. April was honest with her client. She was thirsty and wanted a Ginger ale. Do the same with your customers. Once you are honest within, it’s natural to be honest externally. You can’t have one without the other. Going through a brand transition? A product update? Pricing changes? Honesty is the best policy.

And if you need a dog walker, you’ll probably find an honest recommendation on Nextdoor.

Venture Capitalist Josh Elman is loyal to his Dial Gold soap. He’s been using it since college, for twenty years. It keeps him clean…

I recently returned home from a trip to Las Vegas, where 15,000+ HR professionals were in need of more than just some Dial Gold to combat the 112 degree heat at the Society for Human Resource Management’s (SHRM) Annual Conference. I noticed something interesting while in Vegas: those sweaty HR professionals, like Josh, are fiercely loyal to their favorite brands too.

Day after day, hour after hour, minute after minute, the CareerBuilder and Monster.com booths were packed. Perhaps it was the free cupcakes or stuffed animals, but there were plenty of HR technology companies handing out conference swag that bettered that of the industry’s two seasoned veterans. And it got me thinking a bit about loyalty. Blind loyalty, perhaps.

There are certain brands that can so envelop their consumers that it’s tough to clearly see any alternative as viable. Apple fans. Harley-Davidson riders. Spotify listeners. Everyone has the “products they love to use.”

Do you frequently see a graphic designer abandon a fifteen year love affair with her Mac? No. A fiercely loyal Harley owner jump ship to Yamaha or Suzuki? Nope. What about an Amazon loyalist (for decades) start shopping elsewhere online? She just might…

Enter Jet.com. Very rarely does a company come along that is so disruptive in its business model, so brazen in its ability to square off against a powerful incumbent, that it could change an entire business category. After just a month using the product, I’m convinced we have a serious candidate in Jet.

Almost every study on brand loyalty conducted over the past few years has put Amazon at the top, or near the top, of the charts – which makes Jet’s entrance into the ecommerce category so fascinating to me. Sure, Uber disrupted the entire transportation industry, but people didn’t love the smells, prices, or reliability scores of their local yellow taxi cab companies. Same goes for Blockbuster / Netflix. People didn’t love their late fees nor did they love circling around the inside of a poorly laid out Blockbuster looking for a movie to rent, nor did they love renting Forrest Gump only to open up their video box and see that Angels in the Outfield was in there instead.

People love Amazon. I’m one of those people. I love Amazon Prime- it’s the greatest membership on earth. Free shipping on hundreds of millions of items. Access to digital content like the Golden Globe winning Transparent. I carry a Chase Amazon credit card. I own two Kindles. But Jet, over these past two months, has made me stray. I’ve stepped out on Amazon. That’s what makes Jet so intriguing to me.

Like Costco, Jet sells an annual membership fee ($50) which gives its members access to what Jet calls “profit-free pricing.” “We only make money on membership fees, not the products we sell. That means we’re free to get you the lowest price possible,” the company boasts. It’s a unique way to approach discounting, and it forms the basis for the site’s tremendous potential. Josh can buy an 8-pack of 4 oz. Dial Gold soap bars today at Jet for $4.97. That’ll cost him $9.54 on Amazon.

Despite the extremely competitive prices, the site is still in beta and the UX isn’t fully polished, but over the past two months my Amazon visits have decreased at the same rate that my Jet visits have increased. Some may say that Amazon’s leadership position (and profit margins) in its digital businesses – ebooks, music, video, etc. leave it in a safe position as Jet focuses on building out its physical goods membership service – perhaps that will be true. If Jet’s infrastructure and logistics teams are world class, it has a fighting chance. It will need to start by beefing up it’s inventory – which is obviously lacking in comparison to Amazon’s.

Of course this isn’t necessarily a David vs Goliath story. That does make for nice headlines, but in this case David has raised $200m+ prior to a public launch. That’s an awfully powerful slingshot, if not a modern day M16 to be carrying around on the way to a battle.

Bill Gates said, “We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten.” In the next two years, you may not bat an eyelash. Your Amazon Prime membership still holds tremendous value after all. Way more value than a blue and yellow Blockbuster video store ever held. But if Jet gets a bit of momentum, despite your fierce loyalty to Amazon, you will dip your toe in those purple waters.

Entrepreneurs know it takes patience, and it’s a long game, building a business and a loyal customer base. These things don’t happen overnight. Tinder is the exception, not the rule. Success takes time. Jet has the VC fuel – which buys the time – to develop their product, logistics, pricing models, and infrastructure to compete with Amazon.

If these (extremely) early signs are an indication of Jet’s staying power, Josh Elman may be ordering his Dial Gold elsewhere in a decade.