Hanging up my spurs.

A few years ago, my wife Crystal and I were cleaning out our garage in Truckee when we came across an old notebook of mine from when I lived in Ireland at age 20. Back then, a friend had asked me, “What do you want to be when you grow up?” and I jotted down an answer.

Despite never having heard of venture capital, I went on to describe a job that would involve “a lot of time on the phone negotiating” and overall “high risk, high reward.” I envisioned it as a very lean operation, possibly working out of a bare warehouse, and I would do it half-time from the mountains and half-time from the beach. Last, I predicted that whatever this job was, I would “be the best” at it and then “quit at 40 to try my hand at something else entirely.”

Well, though these days most of the negotiation takes place over email, I did go on to risk every dime I had, more than once, and build Lowercase Capital. As prophesied, Lowercase has earned its spot among the best funds ever despite never having formal office space. Instead, I’ve always worked out of my homes in Truckee, California, Big Sky, Montana (mountains), and Los Angeles near the water (beach).

And underlying all of this? In a matter of days, I am going to be 42 years old. Two years late.

Thus, to dig up the deeply buried lede…

I am retiring from regular startup investing.

It’s hard to leave all this behind right when things are going so well. I’m good at what I do and still improving as I learn from mentors, founders, partners, friends, family, strangers, my own investors, and the experience itself. The better I get at investing in and helping companies, the result is more founders who are excited to work with me and more of my wonderful limited partners insisting I take piles of their loot to keep it all going. People offering you risk-free money is generally considered a positive thing. But, as I have increasingly realized…

Startup investing is one of my things, but it is not my everything.

For a few years, I tried to do this job part-time. But my personal style of startup investing doesn’t work when I’ve just got toes dangling in the water.

The only way I know to be awesome at startups is to be obsessively focused and pegged to the floor of the deep-end gasping for air. I succeeded at venture capital because, for years, I rarely thought about or spent time on anything else. Anything less than that unmitigated full commitment leaves me feeling frustrated and ineffective.

As you’ve heard me say on Shark Tank, if I’m not all-in, I’m out.

So what does this mean for Lowercase Capital itself?

We will continue to passionately support our current portfolio companies. When we invest in a startup, we make a commitment to help them for years and years. That isn’t changing. We just aren’t going to invest in any more companies going forward and we won’t be accepting any money from investors. Climate investing though? That’s another story.

So, all this sad news aside, when do you start filming Shark Tank again?

The love I got from you guys during my seasons on the show was incredible. It choked me up at times. When I first sat in that chair, I wasn’t sure what might happen and what you all might think. Turned out, the Twitter feedback was teeming with high fives, my episodes’ ratings were strong, the press and critics loved it, I invested in some fantastic companies, and most importantly, I had so damn much fun. We even won some Emmys! You all made Friday nights so special for me.

But no more Shark Tank. There simply wasn’t a way to do Shark without investing in a bunch more companies.

Funny enough, the person who is most bummed out to hear I won’t be back is Mark Cuban. Despite what you might surmise from on screen, he and I are actually good friends, just really competitive good friends. I’ll miss working with Mark, and all of the other Sharks. Each of them has been incredibly generous and warm to me and I am proud of all the episodes we made together.

Really? You just walked away from Shark Tank?

I loved taping the show. You can’t necessarily tell when watching at home, but those pitches are each usually an hour long and many are emotional, hilarious, and inspiring. Watched by millions every week, across red and blue states alike, it’s refreshing how many new people from outside my bubble continually reached out to talk with me. The show quite simply embodies the American Dream. You might still catch me doing some TV like the Zach Braff’s series that cast me as myself and I always enjoy a good podcast episode. But no more Shark.

Wait, is quitting all this stuff a prelude to running for political office?


If you follow my Tweets, you know, my attention and anxiety have been increasingly focused on the plight of our democracy (link: to the democracy post). I don’t say that lightly. I think the institutions, principles, norms, and traditions that make the United States of America genuinely exceptional are at serious risk. It has been hard to think about anything else.

As a rich white guy, being an activist/loudmouth in the #resistance often means taking up political positions that are against my own apparent self-interest. These oppressive zealots in the White House are giving people like me a massive tax break and adopting policies that make my already charmed life even easier all at the expense of those Americans who most need our help. But I was raised by parents who instilled in me a deep sense of gratitude and an obligation to give back the gifts I’ve received. My life has been guided by experiences here and abroad that highlight how much we are all in this together.

This is a good time to note that my success would not have been remotely possible without robust public education, access to healthcare, government creation and nurturing of the Internet, federally funded research and science, and the talents of brilliant people from literally around the world. My career would not have progressed without the leadership and contributions of immigrants of virtually every race, ethnicity, and faith. Period.

So, I owe it to do what I can to help, now more than ever.

That kinda sounds like you’re running for office.

I assure you, that’s not going to happen. Nevertheless, I am spending a great deal of time meeting with all of the beautifully spontaneous and decentralized organizations that have been popping up in the wake of our electoral calamity as well as dozens of candidates at all levels of government. I find so much hope in the new wave of leaders and builders who are standing up during these times and I want to be there to support them. To this end, Crystal and I are making seed investments in the startups and organizations that are building a more representative and responsive democracy.

So how else are you going to spend your time?

You mean beyond fighting a despotic regime, doing more television, pushing ahead on Lowercarbon, all while raising three wonderful kids under six? Fair question. My favorite author, Buckminster Fuller, wrote:

“We are blessed with technology that would be indescribable to our forefathers. We have the wherewithal, the know-it-all, to feed everybody, clothe everybody, and give every human on Earth a chance. We know now what we could never have known before-that we now have the option for all humanity to make it successfully on this planet in this lifetime. Whether it is to be Utopia or Oblivion will be a touch-and-go relay race right up to the final moment.”

Crystal and I are committed to doing all we can to ensure Utopia wins. We are passionate about solving our climate disaster, criminal justice reform, and women’s issues and we have a couple of irons in the fire. We are also deeply committed to paying forward the luck and opportunities we have enjoyed in our space. So we’ve been quietly backing the next generation of investors, but specifically women and people of color who have been starting venture funds. A lot more to come across all of these fields, specifically on climate, an effort we are calling:

Keep your eyes peeled for more from Lowercarbon Capital.

Anything else to add, Chris? Or are you just stalling?

Someone must be dicing onions in this room because it’s getting hard to see my screen.

I feel so grateful for all you have given me. Not just our investors and entrepreneurs. But all of you. I am very lucky.

Thank you.

“Why billionaire Chris Sacca is ‘Retiring’ at age 42”

“Chris Sacca retires from VC… and Shark Tank”

“Prominent venture capitalist Chris Sacca retires from investing”

“Chris Sacca says ‘I’m out’ as VC”

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And for that reason… I’m in!

Over the past few months I have appeared on Shark Tank four times and invested in four outstanding companies: HatchBaby, Rent-Like-A-Champion, BeeFree Honee, and Brightwheel. As you read here last year, a strange and winding path put me on the show in the first place. Filming was great and I had fantastic chemistry with the other Sharks. The producers loved the fit and thus my original agreement to tape one or two episodes was extended to tape four.

The ratings for my episodes were strong, especially considering that they kept scheduling me against the World Series and the NBA playoffs to make sure they didn’t lose audience share. But more important to me was the feedback on Twitter and other social media. I guess I expected a whole new universe of haters to emerge. Yet, I’ve been blown away by how many people wrote to say they appreciated my candor on the show and my willingness to have fun squaring off with Cuban and the others.

It’s strange knowing that on a particular day, when that first episode airs, the relative anonymity of your life is going to evaporate. Sure, for a few years there has been a subculture in San Francisco and New York that have recognized me on the street. But being on a show that is viewed by millions and millions of people and constantly re-runs has changed that dynamic. Pretty much everywhere I go now involves at least one selfie. Yet, what I adore is how every single one of those people has something nice to say to me. They are true fans of the show and they have embraced me as a part of it. That feels good.

The best are the kids who come up to say hi. I always wonder which of them are going to carry this passion for entrepreneurship and obsession with the show through to their future careers. The Shark Tank kids charge me up and always leave me optimistic.

I believe that Shark Tank’s success is not an accident. It is hands down the most authentic show on television. There are no scripts. No one tells us what to say or not say. There are no rules about how many deals we have to do. The Sharks are all betting our own money on the companies we back. The competition between us for deals is real and happens without any prompting.

The only thing that is different on the screen than from what you see when we tape the show is that the pitches tend to be an hour long. That gives us ample time to ask in depth questions about finances and supply chains, etc. That stuff can be a little boring, but it’s all vital information to put us in a great spot to make an informed decision about investing. (I have suggested to the team behind the show that they maybe post online one full, unedited pitch just so fans can see the process end-to-end.) Sacca on Shark set

This is a long way of saying, I’m proud to be on Shark Tank. I get a fair number of TV show offers despite the shirts. One major network this year even approached me to be a “Donald Trump-like character.” (Not exactly the best angle to land me.) With Shark Tank, I get to be me, the pitches are the pitches, the action is the action, and the audience can feel the authenticity.

So, I’m writing to tell you all that I have agreed to be back on Shark Tank next season as a recurring special guest Shark. ABC, Sony, MGM, Mark Burnett, and I were all mutually excited about the chance to work together again. While I am not allowed to say exactly how many episodes yet, let’s just say it will be “a bunch more” than I did this current season.

We start taping in June. I can’t wait. Be sure to follow along with me on Twitter (@sacca), Periscope (@sacca), Facebook Live (coming soon), and Snapchat (@csacca) where I promise to make all the show executives nervous about my excessive use of social media on a closed set. I’ll be sure to highlight Robert’s dance moves between takes, Daymond’s fashion advice, Lori’s apologies for walking all over me in deals, Barbara’s heartfelt advice right before she outbids me, the smoke coming from Cuban’s ears after I call bullshit and drop the gloves, and, of course, the extensive, hours long process behind getting Mr. Wonderful’s hair just right.

Meantime, I am grateful for all the love from you. This was a big risk for me and the good vibes have meant everything. See you on a Friday night again soon!


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You Have A Deal.

The punchline: I am going to be a Guest Shark on Shark Tank this season.

The setup: Many of you have asked me over the years whether I would ever consider being a Shark on Shark Tank. My answer was always clear: No.

Why? It struck me as a dime-store version of my current job. A circus of kitchen gadgets and stocking stuffers optimized for infomercials. A few years ago, my buddy Daymond John invited me to come by the set and watch a taping. I arrived just in time to see “Cowboy Ryan” pitch his Cowboy Abs fitness program. I didn’t understand then that it would go on to be considered to be one of the worst Shark Tank pitches ever. However, it solidified my impression that Shark Tank was far afield from what I do for a living.

Last Fall, I caught an old Shark Tank episode on repeat. By coincidence, it happened to feature another of the show’s worst pitches of all time: The Carsik Bib. The minute I saw the entrepreneur pour pea soup and corn onto the floor of the studio, I started teasing my pals Daymond and Mark Cuban on Twitter. I posted this:

Chris Tweet to Damon and Mark

Daymond quickly retorted:

Damon Tweet to Chris

Mark and Daymond retweeted me to their followers and triggered a torrent of passionate replies from their respective tribes. The ferocity was evident. Their fans insisted that Shark Tank was inspiring the next generation of entrepreneurs and even questioned what I had ever done with my life. Cuban and I kept jabbing each other in reply messages. But, all the while, it became clear to me that I had underestimated the impact of the show.

That night, Mark and I direct messaged about his experience as a Shark. He told me how much the show’s success had actually caught him off-guard. Even when he originally got involved, he wasn’t fully convinced of its promise. Now he realizes that it is beyond a mere timeslot. Shark Tank is a movement.

He is right. For starters, the audience is huge. Seven to eight million people watch each episode. It is Friday night’s biggest show with the 18-49 demographic. Among households with income over $100k, it’s is in the top 25 of all programs on TV on any network (broadcast or cable) on any night of the week. Plus, Shark Tank reruns are syndicated to CNBC where they draw another 500-600k viewers in their primetime slot. Episodes of the show are essentially evergreen and can be replayed many times over and still be captivating for viewers particularly when update segments are taped. Shark Tank itself is an incredible business.

Yet, even with those numbers in mind, it was only after talking to people around me that I grasped the reach of the show’s platform. What I had thought was a carnivalesque send-up of the world of venture capital is actually wildly popular among my investing peers. I had no idea. My investors? They love it. The Wall Street guys I work with? Many of them never miss an episode.

The best part? All of these people watch the show with their whole families. Kids are huge fans of Shark Tank and love playing along at home. My own niece and nephew stay up to watch it with their parents and debate which deals are worth doing. Yes, that’s the same nephew who successfully pitched me to invest $35 in his smoothie business, no doubt inspired by the show.

The more I asked friends and neighbors, the more emphatic support I heard for Shark Tank. People lit up when reminded of specific episodes. They said they love the drama of the pitches and proudly buy the products featured. More importantly, I heard more than a dozen times that folks were working on projects they hoped to bring on the show one day. Young viewers noted that Shark Tank showed them the value of knowing how to code and understanding the engineering and design principles behind innovative product creation.

I came to see that Shark Tank embodies the American dream. It is crispest illustration of how ingenuity, determination, storytelling, and a dash of luck can lead to spectacular success. As viewers, we stand right there alongside the entrepreneurs and nervously sweat out what may be the single most important moment in the history of their business, and their life. Shark Tank restores our faith in hustle and reminds us that optimism wins.

I had been so wrong about the show.

How serendipitous then that on Halloween night in Los Angeles, while my family and I were dressed as bottles of sriracha, I bumped into a ninja who was chasing his kid around near mine. In the midst of small talk, he mentioned he was the executive producer of Shark Tank, Clay Newbill. Clay asked me if I would ever come on the show and I let him know right away that I wasn’t interested. So he broke out some ju-jitsu…

If you ever want to get an entrepreneur or investor involved in your project, right off the bat, ask us what we would do to make it better. We can’t help ourselves. We can’t stay quiet. We have too many opinions and derive too much pleasure from building and fixing things. We stick our noses into things as a profession. We know we should be spending our time on some other project in which we are invested. But, if you ask us for our opinion on virtually anything at all, we can’t refuse.

Thus, Clay asked me to come visit his office and talk through some ideas I had for the show. From there, we dropped in to see some honchos at SONY so I could share a couple of recommendations. I went home from that meeting energized and started binge watching all the episodes I could find. In another get together, Clay had me pitching some of my suggestions to execs at ABC. I also found myself at Mark Burnett’s house engrossed in a conversation that ranged from Shark Tank improvements to charity:water to the viability of sea mist condensation systems for fresh water production. (He is a fascinating dude.)

Shortly thereafter, when Mark and Clay called with the offer to be on the show, I looked back and realized all those meetings had been recruiting sessions. They had reeled me in using the sound of my own voice and my inability to shut the hell up when given the chance to toss in my two cents. By that point, I had come to deeply enjoy hanging around with these guys and felt personally invested in seeing Shark Tank realize its potential. So, I accepted their offer on one take-it-or-leave-it condition: I would get to choose my own wardrobe. 🙂

I agreed to be on Shark Tank because watching the show reminds me of the early days of my investing career. Today, at Lowercase, we manage more money than we ever imagined. That certainly has its upside, but it also comes with a ton of politics, conflict, complication, distraction, and ugliness. Shark Tank takes me back to the times when I was sitting around a table at Brickhouse Cafe in San Francisco with just two or three founders, excitedly chewing on what could be the next big thing. There was never any talk of board director dynamics, accounting idiosyncrasies, nor earnings call scripts. Instead it was all about the product itself and musing about how to make it awesome. I have missed that simplicity, focus, and purity so much.

Plus, Shark Tank has introduced me to entrepreneurs that I would never otherwise meet inside the tech bubble. As you have likely read or experienced firsthand, Silicon Valley startup founders tend to be male, and many ethnicities are very underrepresented in our industry. Yet, Shark Tank has already given me the chance to mix it up with brave women and men from across the country and from staggeringly diverse backgrounds. It has been so refreshing.

From this point on, I have to be stingy with details because this upcoming season’s episodes are still being shot and who am I to spoil damn good television? I will say this much:

1) I have already taped a couple of fantastic episodes worth of Shark Tank pitches.
2) The quality of the entrepreneurs and companies is higher than ever.
3) I have done a couple of deals in the Tank so far. Good deals I am proud of and that I know are going to be big.
4) I lost a deal in some very heated bidding that included a fair amount of trash-talking with a fellow Shark. I have no doubt you’ll all bust my chops when when that one airs.

All told, this has been quite an adventure. I have been dying to tell you for months. To experience all of this without being able to Tweet? Consider me, sitting on the Shark Tank set, teasing the hell out of Kevin O’Leary and Mark Cuban and not even getting the chance to Periscope it. But as of today, ABC is taking the covers off and I am free to share this journey with you. By the way, my good friends Ashton Kutcher and Troy Carter have taped Guest Shark episodes too. Keep your eyes peeled for those two.

So, stay tuned. Much more to come in the months ahead. We will do a Periscope Q&A about it soon and I will definitely broadcast the next time I am on set. This is going to be a lot of fun.


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What Twitter Says, and What Investors Hear.

Disclaimers: 1) My funds and I own a lot of Twitter stock. 2) I am not your financial advisor. Don’t trade based on what I write. 3) I don’t work for Twitter, nor speak on behalf of Twitter, nor do I have any inside information about Twitter.

The last few days have been some of Twitter’s most tumultuous in the nine years since I started advising and investing in the company.

I have hesitated to comment on Twitter’s management changes because of the complexity, the sensitivity, and the political nature of the jockeying around who might fill that role. (To answer a question I have heard from many of you, I don’t want to be CEO, nor do I want to be on Twitter’s board.) I also don’t think there is only one right answer as to who should be CEO.

However, any observer will agree that the CEO transition announcements were sloppy and confusing. Investors were left trying to interpret seemingly conflicting accounts and trying to read the tea leaves about where the company was going. Along the way, specific statements about Twitter’s future crushed investor hopes and turned what could have been a very positive event for the company into a debilitating mess.

Yesterday I spoke to an audience of 100 institutional investors about Twitter and fielded their questions for close to an hour and a half. That combined with conversations with analysts and reporters has highlighted for me there there is a major disconnect in what Twitter is saying, what investors are hearing, and what Twitter thinks it is saying. As a person who translates between Silicon Valley and Wall Street for a living, here is what I see.

What Dick and Jack said:

We don’t anticipate any change in that strategy or the product direction.

Dick Costolo and Jack Dorsey held a conference call following the announcement of Dick’s resignation. The next morning, they also went on CNBC to do a live interview. During both of those conversations they made statements to the effect of “We are not changing our product strategy.” These were not well-received.

What Wall Street heard:

Despite slowing user growth and missed revenue projections last quarter we are not admitting there is anything wrong with our business and thus we are not making any changes in the approach to fixing our struggling business.

As a result, the stock got hammered. Investors assumed the leadership team was in denial about reality. Ever since, the stock has continued to lag the overall market and investor sentiment has remained exasperated.

What I believe Dick and Jack were trying to say:

We are nearly ready to launch the products that we are confident will re-accelerate our user growth. We have been working on this stuff for months, ever since Kevin Weil took the product helm. You have seen that our current team has been launching new products at a dramatically faster pace than ever before. These releases, and those to come very shortly, are all part of a comprehensive strategy that we know will attract and retain hundreds of millions of new users. Why would we change that strategy now?

The Twitter team has the benefit of seeing what the rest of us outside the company don’t get to see: the long list of forthcoming products. A strong example of that was today’s announcement of Lightning, a major overhaul of the Twitter experience that will undoubtedly make Twitter more appealing for casual users and enrich the logged-out experience making it much easier to capture and monetize that massive audience. Any of us seeing that product would probably be equally confident about Twitter’s future.

Let’s consider another example of the breakdown in communication between Twitter and investors.

What Twitter says:

Dick is staying on the board of directors and will continue to help the company.

What Wall Street hears:

We are going to have a board that is 1/3 guys who have run this company at some point and that is going to be a distraction for the new team. We need new ideas, not stale ones. How is Twitter supposed to radically change direction if all the old CEOs are still lurking around?

What I believe Twitter is trying to say:

From the time Dick Costolo joined as COO until today, the company’s value has grown by 20x. He oversaw the creation, from scratch, of an ad business currently achieving a +$2 billion run rate and growing 74% year over year. He grew the company by thousands of employees, maintained a very high rating for culture and leadership on Glassdoor, and, following some missteps, finally nailed hiring and promoting the right leadership team for the company. The seeds for the product renaissance that is coming were planted on Dick’s watch.

Product Launches as a Lagging Indicator.

If you have spent time building products in tech, you know that user and revenue growth are preceded by two separate and multi-month phases. First, you have to get the right team in place. Twitter obviously tripped all over itself in this regard for years. Since the era of Jason Goldman, who did an incredible job shepherding Twitter from a simple text-based service to a rich web and mobile platform, the head of product role has been a revolving door.

However, in October of 2014, Kevin Weil was promoted from his then-current role of managing the revenue products, to overall product head of the company. In parallel, his engineering counterpart, Alex Roetter, was promoted to head engineering for the company. Once those two assumed their new positions, it took time to realign their organizations, get status updates on current projects, centralize efforts, and let go any dead weight.

With that foundation in place, they could work with Dick, Adam, Anthony, Katie, Nathan, and others including some board members like Ev and Jack, to re-prioritize the product roadmap to address the challenges facing the company. With new priorities in place, the improved products could be designed, framed, fleshed out, tested, launched internally, etc. But those steps take months and months. It is hard work, particularly for an org that is tackling so much at once on both the consumer and the revenue side of the house. As an outsider, it is now clear though that such work is paying off. They have been making substantial progress advancing the product, and their efforts are now being released to the public.

Now we see the right products hitting the market. The NBA Live timeline was a hit and a giant step forward in making Twitter accessible and indispensable for users new and old. Interactive ads and click-driven pre-populated Tweets are also obvious ways to drive higher engagement and both are now out there. We have also seen Twitter experimenting on Android with using hearts in place of stars. Most important is the news today that Twitter is on the verge of launching their Lightning product, a bold rethinking of the entire product.

User and Revenue Results as a Lagging Indicator.

Will all of these exciting launches impact the company’s results in Q2? Nope. That’s why I assume the company simply reaffirmed their guidance for the quarter. Results will likely be bleak and could, as some analysts have written, show a shrinking user base. That is already priced into the stock and reflected in the general apathy about owning it. The Twitter that users saw for most of the past three months suffered from the lack of improvement that has continually drawn the frustration of users and investors alike.

Will the new stuff impact results in Q3 and Q4? If the company is able to get all of this launched broadly soon, I have no doubt we will start to see the user count and the revenue picture improve. (*Personal opinion, I am not your stock broker, nor your doctor, lawyer, etc.) This is why I remain very bullish on the stock and hope that the company remains independent.

Telling the Story.

Alas, I continue to believe that Twitter’s primary challenge isn’t on the product side of the house as much as that might have been the case in years past. Frankly, there is no shortage of ideas at Twitter about how to improve Twitter. There is no lack of product vision at Twitter.

What has changed is that Kevin Weil and Alex Roetter have been given the reins and they excel at getting shit done. They and their teams appear to now have in place the ideas and the execution to power the future of Twitter. Again, this happened on Dick’s watch and that is why the company’s internal confidence in him as a board member remains high.

Instead, there is an absence of storytelling at Twitter. The issue is that we outside the company have had to do to much work to see and understand all of this. Twitter often still acts like a private company. As a startup in Silicon Valley, you learn to shake off external criticism and continue to work in secret on your new products knowing that you’ll eventually prove your doubters wrong. Yet, as a public company, particularly one with damaged credibility in the market, communication outside the company becomes more critical than ever.

Is this all fixable? Yes. I am optimistic that Twitter will double down on its efforts to reach out to investors and actively listen to their concerns. I was pleased to even see some PR on the Lightning launch today. It has been forever since Twitter promoted a product launch.

While I don’t think Wall Street should be steering the ship, their feedback is immensely valuable. Every time an analyst asks a question, Twitter executives should be asking themselves, “Which cell on her Excel spreadsheet does she have in mind and how can I help her empirically understand the promise of Twitter?” To date, Wall Street has considered Twitter management to be tone-deaf to their questions. So this can easily get better.

In turn, going forward, it will be vital for the Twitter team to pause and consider how their messages land on the ears of investors. They need to be able to put themselves in the shoes of outsiders and very carefully consider how their messages will be heard.

There is so much to be proud of at Twitter right now. All indications are that this company is headed in the right direction. Let’s see if they can get better showing us how all of their moves fit into a cohesive strategy and how Twitter’s best days are ahead. Thoughtful communications will unlock so much value at Twitter and in the price of the company’s stock.

My money says they will get it right.

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What Twitter Can Be.

Disclaimers: 1) This is a very long read. Thinking about a company and using its product obsessively for nine years straight will do that to you. 2) My funds and I own a lot of Twitter stock. 3) I do not speak for Twitter. 4) I have no inside information about Twitter. The company could already be building all the stuff below. I sincerely hope they are.

Summary For Executives And Non-Executives Alike:

I believe in Twitter. The company itself is improving, not worsening. The stock market doesn’t get that because Twitter has failed to tell its own story to investors and users. Here is how I think that story could unfold:

Hundreds of millions of new users will join and stay active on Twitter, hundreds of millions of inactive users will return to Twitter, and hundreds of millions more will use Twitter from the outside if Twitter can:

  1. Make Tweets effortless to enjoy,
  2. Make it easier for all to participate, and
  3. Make each of us on Twitter feel heard and valuable.

Accomplishing this isn’t hard and there are obvious, concrete steps to fix it all. Done right, countless users new and old will find Twitter indispensable, use Twitter more, see great ads, buy lots of stuff, and make the company much more money along the way.

The Opposite Of A Summary:

As I wrote last week, I invested in and have been thinking about Twitter since its earliest days. It is a huge part of my life and my business. I am very bullish on Twitter’s future and I can’t imagine life without it. The way I put it, “I Bleed Aqua.

First, I want to apologize to those of you working in the sensationalist clickbait mines, but this post is not a hit piece. I never said it would be. I am not here to slam the company nor the team. I am not an activist investor.

I am a proud Twitter shareholder and Twitter user. I want this company to succeed. I want the people who work at Twitter to win. I want this stock to be worth more. I own more of it than virtually anyone working at the company. So with that kind of skin in the game, I wrote:

“I am going to post a few things that I personally hope the Twitter team will accomplish.”

If at any point I do sound critical or impatient, it is because I believe Twitter can be so much more than it is today. I assume each one of you who owns Twitter shares, and every single one of you who works at the company would agree. Candidly, I have no doubt that Twitter users have 302 million monthly active opinions as to how the product could be better.

Trying to pin blame on anyone for why Twitter hasn’t made these moves sooner is unproductive. I want Twitter to press forward. I am glad to say there are positive signs that Twitter is once again becoming an organization that can and will ship innovation.

Despite that, my biggest concern is the abundance of public doubt and misunderstanding when it comes to Twitter’s vision and the near future for the service. It’s hard to blame Wall Street or the press. Twitter has failed to tell its own story.

As a private company, Twitter never really had to account for its business to anyone outside the company. Information was tightly guarded and few stakeholders were given the keys. At the same time, investment capital was easy to come by for such a fast growing company, so the company never had to put much effort into pitching itself to raise funding.

The transition to being public has been rough. The company has disappointed Wall Street more often than not. Twitter’s earnings calls are mostly dedicated to playing defense while discussing incremental improvements to sign-up flows and tweaks to the service. Plus, new product launches are soft and rarely get the attention from investors or users that Twitter’s peers drum up. If the company has a bold vision for the future, it doesn’t come across in their communication with us on the outside, and that may very well be a function of pre-IPO legacy.

Over the last few years, my funds put more money into Twitter shares than any other investor in the world, becoming the company’s largest shareholder by the time of the IPO. Raising all that money required me to convince some of the industry’s most skeptical institutional investors of Twitter’s promise. I rose to the challenge, and those investors have enjoyed billions of dollars in profit as a result.

Nevertheless, when I am asked about Twitter’s future on business television, I usually have 90 seconds to answer before they say goodbye and cut to an ad for a Medicare-sponsored scooter. So, let me take this commercial-free chance to tell what I believe should be the focus of Twitter’s story.

What follows is mostly drawn from memos, notes, and presentations I have written over the years through the present day for Twitter management, the company’s board, institutional investors, analysts, power users, and key recruits.

What Is Going Well At Twitter?

  1. The pace of product development has accelerated dramatically.
  2. Twitter has shown a willingness to take more risk in making changes to the core product.
  3. Revenue is growing at 74% year over year. (There is no public company of that scale growing anywhere near as fast.)
  4. The management team has stopped selling their stock.
  5. The Google deal is a big win.
  6. Periscope and TellApart are strong acquisitions. (Periscope may prove to be the most important deal Twitter has ever done.)

Though you wouldn’t know it by looking at the stock price or by reading the headlines, Twitter is owed recognition for ramping up their product development, experimenting with much-needed new initiatives, continuing to grow revenue at astounding rates, and executing well in some marquee M&A and partnership situations. To boot, the executive team has stopped selling the stock and the CFO, Anthony Noto, actually bought a few shares recently. These are all hallmarks of the type of company I want to own.

What’s Not Going Well At Twitter?

  1. New user growth has stalled.
  2. Almost one billion users have tried Twitter and not stuck around.
  3. Direct response advertising has fallen short of hopes.
  4. Wall Street’s confidence in the management team has diminished.
  5. Twitter has been unable to convince investors of its potential upside.

It’s worth noting that Wall Street is the only place in the world where 300 million people using a service and an additional 500 million people visiting a site each month lead to charges that it isn’t “big” or “mainstream.”

That said, Twitter has failed to meet its own stated user growth expectations and has not been able to take advantage of the massive number of users who have signed up for accounts and then not come back. Shortcomings in the direct response advertising category have resulted in the company coming in below the financial community’s quarterly estimates. In the wake of this, Twitter’s efforts to convince the investing community of the opportunity ahead fell flat. Consequently, the stock is trading near a 6-month low, well below its IPO closing day price, and the company is suffering through a seemingly endless negative press cycle.

So Where Can Twitter Go From Here?

Twitter can be indispensable, engaging, and fun for everyone on the planet, and make even more money in the process. So why isn’t that happening?

  1. For most people, Twitter is too hard to use.
  2. For most people, Tweeting is scary.
  3. For most people, Twitter feels lonely.

None of this is a surprise, as Twitter was mostly built by and for its power users. The odds are high that if you are reading this, you are one of those Twitterers who has built lists and muted accounts. You quote Tweets and tag photos with ease, you have multiple group DM threads, and for anything remotely real-time, you turn to Twitter search before Google.

People like you bring incredible value to Twitter and your product experience should never be worsened. Your feedback to the Twitter team has quite literally shaped the product and your passionate opinions remind all of us that there is something really special here. Long live the raw feed and all of its serendipitous glory. Unfortunately, most of the features listed above are complications that chase normal users right back out the door they came in.

The good news is this is all fixable. However, an incremental and iterative approach to improving Twitter will not work. Instead, Twitter will need to take huge risks, deeply question its key assumptions, and launch materially new stuff early and often.

Twitter does have boldness in its bones. It took unreasonable ambition to go from a company where pundits asked “How will you ever make money?” to building a business that will rack up $2 billion in annualized revenue this year. In parallel, it has been no small feat to guide the company from being a wholly text-based service to one teeming with rich media and a growing video monetization business. Even buying Periscope shows the company has the capacity and appetite for taking risk.

But Twitter needs to be bolder still. It needs to place more bets with potentially oversized payoffs. It needs to question aspects of Twitter it has taken for granted. It needs to operate with smaller teams that require less permission to make change happen. Twitter can afford to build the wrong things. However, Twitter cannot afford to build the right things too slowly.

Ultimately, while there is no one Twitter that fits all, there is nothing stopping Twitter from fitting most. There is a Twitter that hundreds of millions more people will embrace and use daily. This is what it might look like…

Using Twitter Could Be So Much Easier.

The world’s very best content is already inside of Twitter. All of the news, sports, entertainment, human interest, music, branding, social justice, humor, politics, celebrities, technology, and beyond. Twitter not only has it all, Twitter has it in real-time, before any other platform in the world.

Yet, for most people, using Twitter to see that great stuff is too hard. Why? Twitter doesn’t work like our minds do. Our brains prefer signal over noise. Yet, on Twitter:

  1. Timelines are oriented in strict reverse chronological order.
  2. Twitter’s core timeline building block is an account follow.

Though immediacy does underpin the value of some Tweets, many other great Tweets have long shelf lives and are just as compelling hours or days later. Plus, a timeline rigidly restricted to specific accounts presumes we won’t value anything Tweeted by accounts we don’t follow. As a result of these two constraints, Twitter timelines are spontaneous, but scattered and of inconsistent relevance.

On any given day, 500 million Tweets are sent. Some of them are wonderfully insightful, funny, provocative, inspiring, heartfelt, or even historic. Yet hundreds of millions of those Tweets are noisy distractions. For any sample of accounts, the odds are extremely high that the most recent Tweets are not the best Tweets.

This is where so many new users get hung up. Hardcore Twitterers have the savvy and patience to continuously tune the array of accounts they follow. They even train the nuances of their visual attention to notice only what they care about when scrolling rapidly. However, new users usually get lost in the rough before they have a chance to find any diamonds.

The next few hundred million Twitter users will want to know that they are always seeing the most interesting and most important Tweets. Sometimes that will mean seeing the freshest Tweets posted. However, in many other cases, users won’t care if those Tweets are ten seconds or one hour or two days old. In parallel, they won’t care if the Tweets were posted by someone they follow or not. They just want the best stuff.

So it is time to ditch the assumptions that:

  1. Recent Tweets are always the best Tweets.
  2. Only the people we follow post the best Tweets.

Twitter Is Making Real Progress.

I am encouraged by some of Twitter’s recent moves in this direction such as Instant Timelines, While You Were Away, and Highlights for Android.

Twitter’s new “Instant Timelines” have definitely taken some work out of the signup flow. Users frequently give up during the new account step where they select whom to follow. Instant Timelines help focus new users’ timelines around meaningful themes of interest and ensure that their timelines are full from day one.

“While You Were Away” is a very positive step toward recognizing that, while real-time Twitter can be astounding, there are countless Tweets that do age well. This is a big, positive shift away from some lingering religion at the company. It shows Twitter is beginning to recognize that recency may not always equal value.

With “Highlights for Android” Twitter casts off restraints around both timing and whom we follow. Instead, Highlights works to show us what it thinks we will agree were the best Tweets of the day regardless of when they were sent and who sent them.

While it is still very early, the quality of the Twitter experience for users touched by these three efforts is dramatically improved. After years of discussing products like these, the fact that Twitter has launched them into the wild leaves me cautiously optimistic that the progress will continue. Going forward, Twitter should boldly push the envelope of these new explorations and try evolving the core product in three directions: Live, Channels, and a Save Button.

Live Is The Biggest Opportunity Yet.

No one else can do live like Twitter and Periscope. Facebook, Instagram, Snapchat, and even YouTube can’t hold a hashtag to Twitter’s live content. Facebook has certainly tried more than once to pinch Twitter’s game, to no avail.

Everything that is happening is happening on Twitter. Every game, every show, every debate, every war, every storm, every ceremony, every tragedy, every election.

Live events tug at the very threads of our being. We all crave shared experiences. Jokes are funnier when we have someone to laugh with. Victories are more exhilarating when we have someone to high five. Catharsis goes deeper when we can cry on the shoulder of another.

In a world of pre-fabricated and polished appearances, live events are raw, authentic, and vulnerable. They bring us together and reveal our commonality.

Yet, experiencing live events on Twitter today can be extremely hit or miss. Why?

  1. We may not know they are happening at all.
  2. We may know they are happening but don’t follow all of the right accounts to get the most immersive coverage.
  3. We are distracted by the rest of our scattered timelines while trying to experience an event.
  4. Even if we are all watching the same event, we have very distinct timelines among us.

Again, this is all fixable. The company can build a high-quality, captivating immersion experience for major live events. The necessary elements are:

  1. A separate tab in Twitter (or app).
  2. Thoughtfully curated follows to build the initial stream.
  3. Human editors.
  4. Scheduling and promotion to build traffic.
  5. No permanent commitment nor login required.

Live Twitter can be built right into the main Twitter app, but it should certainly have its own tab so we can concentrate on the live experience free of distraction. Once we click on that tab, we should see a stream of Tweets prioritized not just for immediacy but for relevance as well.

The event stream will be anchored in following a group of accounts that are directly relevant. For television shows, it might be the actors themselves, the show’s official account, some parody accounts, hobbyist commentators, and celebrities who are known to be big fans of the show. Twitter could also tap comedians and critics to live-Tweet along with the show. As described up to this point, the experience doesn’t seem like more than a well-organized Twitter list. That’s where the human editors come in.

During each event, the company should have an editor or two reviewing the Tweets in stream in real-time and culling them for relevancy, importance, humor, and value. Anything that is noisy will get cut from the stream seconds after it has been published. In parallel, the editors will watch all of Twitter for event-themed Tweets that are earning a lot of hearts and retweets. Anything particularly resonant will be inserted quickly and artfully into the event stream.

To ensure the broadest participation in live events, Twitter will promote them in the main stream and encourage us to subscribe to our favorites, essentially building a calendar of anticipation. The rollout will start with the biggest award shows, the most pivotal sporting events, key political events, and a couple of influencer-heavy shows like Game of Thrones and Shark Tank. This programming will ensure that the most interested audiences won’t ever miss a live feed and it will bring us all back to the service again and again as the range of covered events expands. Done right, live Twitter will have sports scores and TV listings front and center and will be the place everyone visits first to see how the game is going or when the show starts.

Soon after the live events are over these dedicated streams will go away and be replaced by suggestions for other events. No long-term commitment needed. No obligation to stay tuned to accounts of reporters in Egypt after the protests are over. No need to keep the golf commentator in our main feed after the Masters. Our core timelines remain untouched.

Notice also that nothing about this live Twitter format would require any of us to log in. Site visitors to Twitter would be just as engaged and very easy to monetize due to their easily identifiable interests, any search intent that brought them, location and time awareness, plus potential bonus targeting due to prior cookies.

Users will be delighted by the ease of these live events on Twitter. Event tabs will require no effort whatsoever from us. Plus, we will all be watching the same stream together as we enjoy the same show or game or debate, etc. Those shared moments will be intimate and unforgettable. Soon, everyday people will find Twitter to be indispensable during live events.

The best part? Twitter already built a tool that makes a feed like this possible: Curator. Currently, Curator is aimed at traditional media broadcasters who want to cull the best Tweets from the firehose and make them visible to their viewers. Twitter itself would likely need a stronger tool to accomplish this at scale. But once again, it is encouraging to see Twitter building more in the direction of live events.

The other best part? Periscope. I talk more about it in a separate section below. But the only thing more live than Periscope is being there in person. That acquisition was genius and it reinforces that live events are Twitter’s most obvious place to win.

All told, nailing live events will give new and existing users a compelling reason to regularly use Twitter and will be a strong impetus to bring back inactive users who signed up long ago.

Channels Will Make Twitter Easy, Easy, Easy.

Almost all media in our lives comes to us through some sorting and categorization. We have come to rely upon filters to help us focus our attention topically. Most of us have a few preferred websites for news and entertainment, we reach for a particular section of the newspaper, we have a handful of magazines we like best, and we know which are our favorite channels on television.

This makes the diversity and meandering of a typical Twitter stream feel dizzying to a normal person. While there is some value in the serendipity of discovering the unexpected, the energy expended to parse a busy stream is overwhelming for too many.

Twitter has shown that they understand at least part of this. As discussed above, their Instant Timelines launch takes a big step forward in orienting a new user’s stream around themes of interest. The result is a good start, but ultimately the user experience is muddied by multiple interests and subject matter all being forced into a single stream.

This can be done better and in a way that is immediately intuitive to most people with the introduction of channels that are oriented by:

  1. Topics
  2. Location
  3. Popularity

When it comes to media, people like programming. We like focus. We like doing the same thing at the same time and being told where to go next. For instance, in the realm of TV, with only a few exceptions, DVR audiences don’t compare to the size of live audiences, even for re-runs. We want to watch it together in the moment. Ever notice that whatever long forgotten movie TBS is playing on Saturday afternoons almost always trends on Twitter? We are sharing that moment.

To be successful, Twitter channels would require:

    1. A separate tab (or app).
    2. Consistent, focused content.
    3. Human editorial enhancement.

Topics Bring Focus And Consistency To Streams.

A natural extension of the Instant Timeline approach would be to launch simple subject matter Twitter streams on separate tabs or in separate apps. This would not be a major departure from Instant Timelines except that these channels would be concentrated on a single topic and would not just be algorithmically generated, relying also on human editorial contributions.

Topical channels would be less about immediacy and rather more closely resemble the Techmeme model of making sure that the most important content ultimately makes it into the stream. Plus, all of us watching a feed would see the same Tweets at the same time.

The most obvious channels to kick off would be news, politics, sports, entertainment/gossip, comedy, gaming, and a “Best of Twitter” highlighting the most popular content on the service overall. Never underestimate each of our desires to tend toward the mean and feel at home within a big group. Too much personalization can be exhausting. Overall, I can’t imagine there would be much objection within Twitter to this approach yet, it would immediately make so much sense to everyday people.

Location Is An Intuitive Yet Enriching Way To Stream Tweets.

In the early days of Twitter, there used to be views into Tweets that were oriented by the location from which those Tweets were sent. You could literally watch Tweets appear on a map.

So much relevancy and value can be inferred by the sender’s location. A Tweet about a protest would take on increased importance if you could see that it was sent from Baltimore or Ferguson. Tweets about the Super Bowl are that much more thrilling when we know they come from inside the stadium. In the midst of earthquakes and storms, Tweets have so much more value to us if they are written by others nearby.

For years, location has been neglected within Twitter. Despite a fantastic deal that Twitter signed with Foursquare for place data, and a fair amount of location tagging on Tweets, there is today no mainstream location-oriented view of Tweets. Yet, even Twitter’s newest users would immediately understand and enjoy that kind of interface.

Popular Content Wins Every Time.

A third way to organize content from Twitter is to highlighting what the Tweets are linking to. If you’ve used Nuzzel (disclosure: one of our portfolio companies) you know exactly what I mean and how simple yet magical that experience can be. If you haven’t used it, try it. Nuzzel makes Twitter better.

Want to know what are the most popular articles linked to on Twitter? That should be a channel. What are the most popular sites linked among the people we follow or people that our friends follow? Great channel. Which books are people Tweeting about? Channel. Which videos are garnering the most attention? Channel. Any particular .gifs blowing up? Channel.

In each case, Twitter already has all the information it could want.  There is often a temptation to overthink this and try to build more science around it than necessary. Basic link counts work pretty damn well. Twitter just needs to surface this lens. Once again, everyday users would immediately wrap their heads around this and come back again and again.

Twitter Can, And Should, Live In Separate Apps.

The channels described above and live Twitter itself could very well thrive in standalone apps. If Twitter acquired Nuzzel, it could become Twitter News tomorrow. The day’s most important news as determined by who we each follow? Obvious and easy to use. Not logged in? Doesn’t matter. Twitter still knows exactly which news was most popular and engaging across the network.

The company could also launch experiences with the governing bodies for each major professional sport. Instead of having a Twitter tab buried within a sport network’s app, Twitter could build apps that look and feel just like Twitter but with strong subject matter concentration, scores, and highlights.

For example, Twitter NBA could build off of the company’s fantastic relationship with the league and include a focused and live-driven stream full of the very best Tweets and the instant-replay video content under the company’s existing Amplify deal. NBA fans would be thrilled to use that app while the game is on and the ease of advertising in that app would generate plenty of money to share back with the content partners. The same approach would work for the biggest global soccer and cricket leagues as well as the WNBA, NFL, MLB, and NHL. Twitter should consider integrating a fantasy partner like Draft Kings as well to make it a must-open app. While there are a number of fantastic mobile experiences for hardcore fans, no one has built the perfect live-action companion app for casual sports viewers. Twitter has the best shot at it.

Twitter gave a standalone music app a shot a couple years ago. It didn’t pan out, but that had more to do with its limited functionality than anything else. My hope is that Twitter sees the Twitter Music experience as proof that radical experimentation is relatively painless in the end and worth revisiting again and again.

Additionally, new apps would give Twitter a fresh shot at mobile notifications. This was a primary driver of Facebook’s move to break out Messenger as a separate app. So many users had turned off Faceboook mobile notifications that Messenger had no chance at immediacy within the main Facebook app. More notifications equals more use and attention, so a renewed notification setting would be great for Twitter.

Overall, the focus and simplicity that would come with standalone Twitter apps would be irresistible to hundreds of millions of new users and would substantially improve the experience of countless existing users all while being exceedingly easy to monetize.

Twitter’s Save Button Would Let You Keep All The Good Stuff.

So much of the time, Twitter moves too fast. If we follow a couple hundred active accounts or more, the Tweets often come in faster than we can read them. As a result, we feel pressured to keep refreshing rather than dive in meaningfully and take our time to explore the stuff that interests us. At the same time, really intriguing Tweets and links go by and we don’t have a way to save them for later. Poof, they’re gone.

In parallel, fast streams are incredibly hard to monetize with commerce and direct response ads. We are living in the age of sales conversion, and Mary Meeker’s recent presentation highlighted that the next big trend in apps is indeed the inclusion of “buy buttons.” Twitter’s TellApart acquisition was very smart and will dramatically improve the intelligence behind the company’s direct response offering. However, if Twitter genuinely wants users to buy things at scale, they have to give us a chance to consider the offers and make a decision in a matter of minutes/hours/days, not just seconds.

Building the right conditions to bring commerce forward and more deeply integrated into Twitter should be a priority. Twitter has the former CEO of Ticketmaster heading up commerce. Very few people in the world know how to sell things online better than he can. It’s time to take advantage, and here is one idea how.

We have a wonderful company in our portfolio called Rex. It’s in a closed beta, but for anyone reading this they have offered a peek. Go install the app: Rex.is/here and use the signup code: SACCA.

Right away you’ll see Rex is a feed of interesting things posted by users in a follow model. It’s a place to showcase anything we love. Books, movies, restaurants, albums, gadgets, apps, etc. One feature that distinguishes Rex, is something we have been talking about around Twitter for years: the concept of a “Vault.”

See anything in the Rex app you want to remember or come back to later? One click and it is stored in your Vault. Later that week when you are thinking about which movie to watch? Check your Vault and see which you stashed there. Wondering where to go eat? Look at the new restaurants you saved to your Vault. Saw a cool drone in your Rex feed earlier and now have the time to read the reviews and decide on pulling the trigger? Good thing it is saved in your Vault. In fact, everything in your Vault is beautifully organized by the category of item it is. It’s a truly delightful experience.

Twitter should buy the folks at Rex and have them come on board to build what we have often called a “Save Button” for Twitter. (For what it’s worth, we have also have referred to it as a “Keep Button” or a “Twitter Keeper.”)

Imagine if every single thing we saw on Twitter could be saved/stored indefinitely. Not just every article or link like with Pocket, but every Tweet, every photo, every video. We could keep every product we saw mentioned, every book that looked interesting, every destination we wanted to visit someday, every concert we wanted to go see, and every ad that piqued our curiosity. All of this could be saved to a Vault within Twitter with just one button in line with the RT and Fav buttons in each Tweet.

That Vault would also be where brands could present offers to users. Using the same tech that targets those promoted Tweets very well today, Twitter could show us direct response and buy button offers but in a much slower-moving, and conducive environment.

Want to take time to consider Virgin America’s ticket sale? No worries, it will be waiting for you here in the Vault. Twitter knows you are a big Golden State Warriors fan? The Vault will be the perfect place for the team to make you an offer on tickets and merchandise.

The Vault will also be the ideal location in Twitter for iBeacons and real-time, location-aware offers. Walking into a store that has a great deal coming your way? If they put that into the main stream it will be lost. Instead, notify us the users, and let the offer remain in the Vault where we can read the fine print, discuss it with our partners, do some comparison searching online, and consult reviews sites.

Twitter can accomplish all this just by building a slower place in the app. A safe place where we can keep anything we want for as long as we want, cementing Twitter’s permanence in our lives. A place where everything we save is neatly categorized for us. A place where buy buttons and deals can linger long enough to let us all consider and act thoughtfully upon them. A place where we don’t feel rushed.

In all, live Twitter, channels, and Twitter’s Vault will evolve Twitter to feel more familiar and approachable to hundreds of millions of new users. By prioritizing events, Twitter can capture the excitement and intimacy that come with shared experiences. For new and existing users alike, channels will take so much of the work out of extracting good, predictable value from Twitter. The Vault will ensure that the best things we ever see, experience, and are tempted to buy on Twitter stay with us.

Enjoying Twitter can be so much easier for so many more people.

Tweeting Shouldn’t Be So Scary.

Since the earliest days of Twitter, we have known that a huge obstacle to people joining or frequently using Twitter is some version of:

“I wouldn’t know what to Tweet. I don’t really have anything to say.”

Feeling obligated to post to Twitter creates so much anxiety that it actually keeps hundreds of millions of people from sticking around. The company hears it all the time, and I have no doubt that you have heard it from friends as well.

However, we all know that you don’t need to Tweet to derive value from Twitter. The company has said that as much as 40% of the active user base only ever reads Tweets. In principle, that’s just fine. However, since Twitter is a company that gets paid based on engagement ads and not display ads, they can do better.

Every one of us wants to feel heard. It is a universal human desire. Twitter could be the perfect platform to make us all feel like our self-expression registered somewhere. Let’s run through some examples of how we might all contribute to Twitter without having to stare down the menacing white space of that Tweet compose box. These are in order from most user effort required to the least:

Nudges – Questions from an ever-evolving list would prompt free-form but focused responses from users. Example: “Who influenced you the most growing up?” “What is the grossest thing you’ve ever eaten?” Everyone has an answer to questions like these and feel very little risk in answering. The questions could be served up in the compose interface on a rotating basis. Any Tweets resulting would appear within the Quote Tweet construct showing our Tweet as a response to the original question.

What Do You Think About This? – Interesting articles could either be selected organically or as a result of paid promotion by a publisher. We would be pointed to the piece, driving partner traffic, and then asked to Tweet our reaction. Again, the resulting Tweet would be displayed within the Quote Tweet context.

Question Of The Day – Either ripped from the headlines or appealing to a popular approachability, Twitter could post a single question of the day for all. Feature it in the compose window and on the trends/search page. An editor could grab the best of our responses and feature them.

Show Us Your Best/Favorite/Goofiest – Capitalize on the engagement around Throwback Thursdays by giving people more opportunities and prompts to post images and video. “Show us your goofiest ever Halloween costume.” “Show us the best holiday lights in your town.” “Show us your favorite puppy.” The challenges would last only for the day and the best results would be posted in a digest the next day. Very engaging, adds some urgency, and gets users to load more media onto the system which we know makes them more likely to stick around longterm.

Surveys/Polls/Multiple Choice – Within our streams we might find an interactive Tweet asking us to click buttons to answer questions like: “Who will win Best Actor tonight?” “Who performed best in the GOP debate?” “Who will be the next voted off American Idol?” “Which should be the next Doritos flavor?” “Who should be the NBA Finals MVP?” “Which song should Beyonce start the show with?” They don’t have to be commercial or promoted, but they obviously can be. Questions like these are irresistible, particularly if we get to see how our choices stack up against the results.

This Or That? – Same as above but with only two choices. “Will Cleveland or Golden State win?” “Who should win this election?” “Who wore it best?” “Tastes Great or Less Filling?” Incredibly simple interfaces native to Twitter cards that invite to just click one side or the other.

In each example above, more and more burden is taken off of us to create Tweets from scratch. Yet in each we still feel like we have an opportunity to express ourselves and that our voice will be counted.

The good news is that, after a long time of talking about it, I have recently seen hints that the company is moving in this direction. An ad for the new Entourage movie had a click button quiz to determine “Which member of the Entourage crew are you?” quiz. Alluring to many users, pleasing to advertisers, and overall good for the level of user participation on Twitter.

Some of you who are power users and Twitter purists might be throwing up in your mouths a little what with all of the sponsored and interactive content mentioned above. I hear you and I will reiterate my support for always keeping the complexity of the raw feed alive. But the challenge for Twitter is to attract and retain the next few hundred million users and it’s clear the current product isn’t exactly doing it. So the doors need to be opened to fresh uses.

However, I have some things in mind that you too might like:

Native OneShot – It’s no coincidence that a former Twitter employee created an intuitive way to quote text while posting a visually engaging Tweet linking to the source article. The result has been rich Tweets with strong context and very high engagement. Twitter should acquire OneShot to be built directly into Twitter. With a little work, Twitter’s OneShot could probably learn to recognize optical characters in any imported photo or screenshot. Powerful stuff.

Autocomplete Links And Media – Today, Twitter suggests autocompletions for any user handles or hashtags as we start typing them. Twitter should extend this capability into making good guesses about what may be relevant links and media that we might want to embed in our Tweets. For example, if Twitter sees me typing about Steph Curry’s monster game, in the lower third of the compose pane it could suggest links to articles about the game. Similarly, Twitter could suggest public photos, Vines, or Amplify videos I might want to include in my Tweet. Twitter already knows which links and which media are seeing the most engagement, so why not give my Tweet a quality boost by ensuring it has the best content embedded?

Going Beyond 140 – I definitely think the 140 character limit per Tweet should remain sacred. It’s a beautiful constraint that has inspired a whole new form of writing. However, when users do need to type more than a sentence or two, it pains me to see them take that traffic and attention off the Twitter platform. Twitter should deeply integrate Medium and/or WordPress (disclosure: we are investors in both) into the Tweet compose interface. Need to write something long form? The first 140 characters would be your Tweet and the rest would be directly embedded into your Tweet and hosted in a Twitter-friendly way, already optimized for cards. Landing page monetization could easily follow.

Everything covered in this section would increase the number of people who are each adding value and content to Twitter. The light touch methods would reel in and retain new users who have traditionally been anxious. The deeper integrations would embolden the incredibly valuable power users to bring more great material than ever into Twitter.

Using Twitter Doesn’t Need To Feel As Lonely.

Most of us have a Facebook and an Instagram account. When we post our thoughts or photos to those services we are bound to get many likes, hearts, and comments from our friends and followers. Even users with the smallest followings receive these interactions.

Engagement like that with our content and our accounts triggers a dopamine response. As humans, we love getting attention. We crave approval. Those likes quite literally make us feel good at an emotional and a chemical level.

Yet, post that same material to Twitter and, though more people may actually see what we shared, we are unlikely to get much interaction with our Tweet. In fact, most Tweets will never be starred nor retweeted nor replied to at all. Thus, Twitter starts to feel lonely and less fun. This can be fixed. Twitter can make sure each of us sees more activity and feels more noticed and appreciated by considering the following:

Favorite Is Too Strong A Word – A very high bar is set by using the word “Favorite” on Twitter. Favorite is a superlative. It implies a ranking. In the early days of Twitter many of us interpreted the word literally and only keep a few Tweets in our favorites that were truly, well, our favorites. Today, many of my friends and I use the star as a “Like” button equivalent or even a simple acknowledgement that we saw a Tweet. Whereas other people use favorites as bookmarks. However, the majority of users are baffled by favorites and they don’t end up using the star much, if at all.

Bring On The Hearts – It is high time to introduce “Hearts” to Twitter. For years, folks at Twitter struggled with whether to use a more casual gesture. Suggestions even included buttons that said “Good” or “Thanks.” It is now clear from across the Internet and throughout the world of apps that the heart is universally understood and embraced. (In fact, Periscope’s unlimited heart repetition has elevated the social feedback loop to a mind-blowing new level.) If Twitter integrated a simple heart gesture into each Tweet, engagement across the entire service would explode. More of us would be getting loving feedback on our posts and that would directly encourage more posting and more frequent visits to Twitter.

Double Click To Heart – Instagram’s double-click to heart is a killer feature. Tweets are filled with so many actionable click opportunities that there isn’t an obvious way to make an entire Tweet double-clickable to put a heart on it. Nevertheless, there are two clear opportunities to incorporate the gesture into Twitter. First, all uploaded pictures and videos on Twitter should be double-clickable to heart. (They can still be pinch zoomable and single click playable.) As noted above, users would be thrilled by the love shown to their posted media and it would greatly encourage the uploading of more. Second, double click to heart should be introduced to Direct Message threads as a way to acknowledge and love a message.

Read Receipts Will Blow Minds – So many Twitter users are here among us just to follow celebrities or “VITs” (Very Important Twitterers). Twitter is uniquely great for that. However, following those VITs can sometimes feel distant. It’s impossible for a high profile user with millions of followers to meaningfully interact with them all. So Twitter should introduce Read Receipts. For example, if we follow Tyra Banks, the next time she scrolls through her notifications tab and sees that we followed her, we should get a notification in our feed saying “Tyra Banks saw your follow.” To feel like we just shared a moment with such a famous person and she saw that we exist? So cool, heads will explode. Similar notifications will be sent whenever a VIT sees that we hearted or retweeted their own posts. The same amazed reaction will result. Thus, even users who never Tweet will consistently see incredible activity in their notifications simply as a consequence of engaging VITs on Twitter.

Thank You Bombs – To kick it up one more notch, each VIT with a huge following should be given a button that triggers a “Thank You” notification to all of their followers at once. Again, it will create a sense of recency and togetherness with all of us who follow the VIT as well as give the VIT an efficient way to express gratitude to their entire following. The timing of it would be such a meaningful gesture and would draw the VIT’s following community together.

Trending Credit Where Credit Is Due – If a user retweeted, hearted, or mentions a theme or a hashtag that later starts to trend, put a notification in their activity stream acknowledging their contribution and the role it played in helping the make the trend possible.

Timehop And MorningPics Make Every Day Throwback – These two apps both do a fantastic job of bringing up past posts and pictures from a feed, sometimes going years back. Who doesn’t love looking at their own history? These services trigger instant nostalgia and make for really endearing content. Twitter would do well to explore working with them to build its own twist on such a feature. Speaking of, Facebook just launched something similar this week.

By moving past the favorite and introducing the heart, Twitter will invite levels of activity and engagement that the service has never seen before. New users will find the hearts familiar and comforting. Overall feedback will increase dramatically making Twitter a friendlier and more compelling place for users new and old. Plus, Read Receipts, Thank You Bombs, and Trending Credits will make every single one of us feel heard and valued on Twitter every day.

Periscope Will Be Bigger Than You Think.

As I mentioned earlier, Periscope may prove to be the most important acquisition in Twitter’s history. If Twitter’s unique advantage is real-time, then Periscope takes that lead to the next level. The audience response to Periscope broadcasts is emotionally visceral. There is live, and then there is standing just one selfie away from the planet’s most interesting people.

I have been very impressed by Kayvon, Periscope’s co-founder and CEO. With incredibly limited resources, he and his team have built a beautiful and intuitive product. He is sharp, thoughtful, and gets shit done with a smile.

Of course there are things I would like to see improved like removing the spammy and entrenched Periscope leaderboard, featuring more of the network’s high quality content, improving high value broadcaster discovery, allowing for broadcasters to schedule upcoming streams, and so on. But, Kayvon has his team executing very quickly and I have no doubt they will tackle all that they need to soon enough. With one exception…

The current 24-hour expiration of videos is heartbreaking. All broadcasts on Periscope need to be archived for playback permanently, unless the broadcaster chooses to delete the recording. So many treasured moments have been shared on Periscope only to vanish a day later. David Blaine has showed us some rare magic tricks, Oprah has brought us behind the curtain and into her life, Commander Hadfield played “Major Tom” in his living room, and Richard Branson gave us all entrepreneurial advice from his private island. Each of those videos would otherwise be interesting and watchable for a long time to come, but now they are gone.

This concerns me not just as a user, but as an investor. Ultimately when the time comes to monetize Periscope (which I agree is not yet), the easiest path will be to place very short/Vine-length ads just before the playback of archived broadcasts. There is absolutely no need to place ads into a livestream and interrupt the user experience. The archived video playback alone will generate incredible cash-flow in addition to being perfect for search results and a huge honeypot for attracting new users. Beyond that, Periscope will also be able to do promoted broadcasts and promoted accounts just like within the Twitter model.

As I said, Kayvon’s product instincts have been strong. Look no further than his team’s innovation around the constantly streaming hearts in the app for an example of that. I have no doubt he will deftly guide Periscope for years to come. Watch this space.

Conclusion: Twitter Can And Will Be Huge.

Twitter’s biggest challenges today are its slow-growing user base, its high number of inactive users, and a product flow that makes direct response and commerce transactions challenging. All of this is compounded by Twitter’s unsuccessful attempts to convince investors and the public that it has a clear vision and product roadmap that will accelerate growth. The stock price reflects the resulting misunderstanding and doubt.

In the absence of any better metric, investors and the public have focused on Monthly Active Users (MAU). While MAU can be one helpful guide, it certainly misses the entire picture of the state of the business. Logged in users are always nice to have, but Twitter’s logged out visitors will continue to be increasingly valuable. Between search and referrer intent, geographic and time context, TellApart data, cookie data, data gathered from developer tools, and inferences from engaged participation in the stream, there is no ceiling on the potential to make money from this logged out audience.

Twitter has already shown it knows how to build a healthy business at scale and continues to grow faster than any public company of its size. In addition, with every proposal in this post, obvious opportunities for additional monetization emerge. Everything I discussed can be thoughtfully and effectively promoted. Plus, by creating a save button, Twitter can build a home for a significant direct response and commerce business.

On top of all this, Periscope will grow to be the world’s most compelling and intuitive app supported by a YouTube scale business monetizing some of the most valuable and engaging content archives in history.

Since 2009, when I decided to start buying all the Twitter stock I could find, and through all the years I convinced huge institutions to invest in the company with me, I have focused on one measure of the health of Twitter’s business:

“How big is the audience they can show ads to?”

Nail that, and everything else works itself out. So, to make sure no one is ever surprised by the answer to that question again, Twitter simply needs to:

  1. Make Tweets effortless to enjoy,
  2. Make it easier for all to participate, and
  3. Make each of us on Twitter feel heard and valuable.

Done right, and done soon, hundreds of millions of new users will join and stay active on the service, hundreds of millions of inactive users will return to the service, and hundreds millions more will use Twitter from the outside. Countless users, new and old, will find Twitter indispensable, use Twitter more, see great ads, buy lots of stuff, and make the company much more money along the way.

I believe Twitter can do it. I hope now you do too.


(Footnote: I didn’t touch on Direct Messaging, Vine, Developer Tools, Niche, Search, Digest and Offer Emails, nor a host of syndication and M&A opportunities. Each of those is an exciting area with material potential. For now, I chose to focus on the most core and attainable goals that I believe will have the largest and fastest impact. Plus, for the love of god, this thing is already 8,500 words long.)

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I Bleed Aqua.

Disclaimers: 1) I own a lot of Twitter stock personally and in my funds. 2) I definitely do not speak on behalf of Twitter. 3) I do not have any inside information about Twitter. 4) I can’t think of a fourth thing to disclaim, but putting this here just in case.

Twitter has held a close place in my heart since Ev signed me up in 2006. It made me feel closer to people who I wasn’t actually near. It brought me more diverse perspectives than any blog reader ever could. I found myself in the center of events, sharing experiences, posing questions, passing along lessons learned, and making unexpected friends.

My initial investment in Twitter was relatively small, but as I grew increasingly confident the company would change the world, I bought more and more stock. At one point I had even exhausted all of my savings purchasing Twitter shares and was technically insolvent. During those years, I walked into the company’s office, often uninvited, and did whatever I could to be helpful. The now CEO of Microsoft, Satya Nadella, sat across the table from me as I helped negotiate Twitter’s first few search monetization deals. I had investors like Jerry Murdock at Insight Ventures gas up their jets to fly to SF and invest at a then-staggering $1 billion valuation. I grabbed the phones of any celebrities or politicians or company heads I knew and installed the Twitter app before they could say no. I pitched in to land big recruits like Adam Bain and Alex Macgillivray. I was obsessed with helping.

Twitter went from just being an investment to a huge part of my identity. My kids can spot a Twitter birdie from a hundred feet away. I have very few t-shirts that don’t sport the company logo. On Twitter, I have shared my wedding, my kids’ births, my proudest and darkest moments. I have shot my mouth off, and (sometimes) apologized for being wrong. I have taken unpopular stances, and revealed my code for living and what drives me. I have raised money for charities, raised money for politicians, and raised money for startups. I have cracked lame jokes and made vulnerable admissions. My wife and I even painted a room in our house the exact shade of the Twitter bird.

Along the way, I cultivated a precious group of Twitter followers. In the early days, my Tweets were pretty goofy. With time, the increasing size of my audience was daunting and I felt a sense of responsibility to add some value to their days. Through the ups and downs of my business and my personal life, I came to rely upon the feedback and support from my followers. Through the years they have kept me honest, focused, optimistic, and never feeling alone.

In parallel, since the earliest days investors and pundits had been asking skeptical questions like “How will Twitter ever make money?” and writing doomsday pieces with dead bird clip art. I spent a couple of years trying to convince them of Twitter’s potential and ultimately decided that rather than waste the energy, fuck it, I would just buy all the stock I could find. It was a seemingly impossible aspiration for a guy living in Truckee with no office and only one employee. Nevertheless, by the time of the IPO, my affiliated funds had accrued the biggest stake in the company.

Throughout this entire time, I never worked at Twitter and I was never on the board. I have been involved with the company as long as the now-CEO, Dick Costolo. We both invested in the earliest outside round and we both served as advisers. In 2009 he joined Twitter full-time as the CEO and I stayed outside.

Consider for a moment having so much of your life, your energy, your attention, your passion, and your net worth tied up in a company where you don’t work. A company where no outsider can attend the weekly all-hands meeting. I am no longer an official adviser to Twitter and I have no more exposure to the product roadmap than any other person who isn’t a Twitter employee.

Yet, I certainly have strong opinions about Twitter. Frankly, who doesn’t? I yearn to know where this company is headed. Having been one of the first 140 users, I have seen multiple eras of the product. I have navigated three CEOs, a couple generations of the board, and continual evolution of the management team. I have listened to 9 years of complaints about what isn’t working and bold claims from all directions about what Twitter is/isn’t and should/shouldn’t be. I have offered countless of my own suggestions about what could be better and what Twitter should do next. (For the record, a bunch of those ideas were dead wrong.)

During all of these years, I haven’t been as candid as I could be in public discussions about Twitter. I have made dozens of television appearances in support of Twitter and thousands of emails and calls with analysts, investors, reporters, potential hires, partners, you name it. I always felt like the birdie was one of my children and I needed to defend it at all costs. I never expressed any frustration or disappointment at missed opportunities or any exasperation at what wasn’t happening. However, a recent Periscope I did with Jim Cramer at CNBC changed my stance on that.

In the hours following the latest earnings call, Cramer and I traded insights as to what we each thought was going wrong and what could be better. It felt good to be both a critic of Twitter and yet reaffirm my steadfast belief in its potential. It was cathartic to say what was on my mind to an audience broader than just a few executives at the company. Most importantly, those messages resonated with the viewers, some of whom were Twitter employees. My Tweet mentions and email inbox were filled with passionate stockholders and Twitter users who cared deeply about what was ahead for the company.

I write all this because I am soon going to post a few things that I personally hope the Twitter team will accomplish. I want to make clear that my feedback comes from a place of loyalty and persistent gratitude. I love Twitter. I use it for hours each day and can’t imagine life without it. I also love the people building Twitter. Many of them are like family to me.

I believe without reservation that Twitter can soon evolve to be used by over 500 million people a month. I believe there is no natural ceiling on the revenue Twitter can generate. I also believe that Twitter’s reach can become more pervasive and its impact on the world more meaningful. I believe Twitter is a great investment and that the stock is cheap.

So stay tuned for a few more of my thoughts about Twitter. In the meantime, thanks for giving me the chance to reflect on a journey that has meant so much to me.

I bleed aqua.


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Why I would never want to compete with Travis Kalanick.

(Disclaimer: I own a bunch of Uber stock.)

Over the last couple of days, there has been assorted press speculation about Google launching an Uber competitor. As a proud Google alum, I have deep respect for the company and, in particular, I consider Larry Page an absolute genius. Working with him was a privilege. However, when I posted this Tweet about Larry and Uber CEO Travis Kalanick and it led to a lot of reporters asking me for a deeper explanation:

Let me tell you a little story that might give you a sense of why I think trying to take on Travis is a losing proposition:

A few years back, before Uber was anything more than an app used by a group of our friends, Travis was staying at my house in the mountains over the holidays. One morning before snowshoeing, my dad challenged Travis to a friendly Wii Tennis match. My dad is a competitive guy and used to enjoy playing in local, real-life tennis tournaments when I was a kid. He also had a Wii at home and considered himself versed in the virtual game. So, he thought it could be a good opportunity to dish out a little good-natured pain to Travis.

As the match kicked off, there was my dad in an athletic stance and confidently giving it his all. He might have even been sweating a bit. Yet, Travis was barely moving his arm or breaking his wrist. Though my dad hung in there and kept it close, Travis won every game.

That was when TK, with full Princess Bride panache, announced that he had been playing with his opposite hand, and promptly swtiched. Uh-oh. For the next 20 minutes, my dad didn’t manage to score a single point. He was completely skunked. Yet, looking over at Travis, it was clear he was still waking up.

Travis could tell my dad was feeling dejected. I mean, the poor guy was getting aced at least every other serve. A slight smirk came over TK’s face and he reached out to shake my dad’s hand, offering him a touch of consolation.

“I have a confession to make, Mr. Sacca. I’ve played a fair amount of Wii Tennis before.” While talking, he used his controller to navigate through the settings pages on the Wii to a list of high scores. “In fact,” he continued, “on the Wii Tennis global leaderboard, I am currently tied for 2nd in the world.”

I had known Travis since the days I worked at Speedera, a head-on rival of his company, Red Swoosh. I knew he was eerily brilliant and could do some powerful math in his head. His reputation as a gifted salesman and product strategist preceded him. I had also seen years and years of how scrappy, ingenious, and resourceful Travis can be when building his business. It was a mutual admiration of these characteristics in charting our careers that led to us being friends in the first place.

But that day in Truckee, I was reminded of how tireless and obsessive Travis can be when it comes to achieving goals he sets out for himself. If he decides he wants to research a new industry, he will be a veritable expert within days. If he wants to understand a new city, he will be there 24 hours from now with just a half-sized backpack and already hanging with the locals. If he wants to be one of the best Wii Tennis players in the world, even while busy co-founding one of the fastest growing companies in history and advising a half dozen others from his storied Jampad, just give him a couple weeks.

He doesn’t sleep. He doesn’t lose focus. He will even forget to eat. He executes again and again, inspiring those around him to have the same passion for the end game as he does. So, if Travis decides he wants to provide a cleaner, safer, easier experience than the current taxi system, he will make that work. If he sets his sights on reforming pervasive, anti-consumer regulatory corruption, watch those laws soon fall while exposing the shady backroom deals that created them. If he wants to eviscerate the racism that keeps people of color from having consistent access to rides in taxis, that will be the result. If he wants to take drunk drivers off the street, you will see the fatality rates fall wherever he operates his business. If Travis wants to build a company that offers, as Uber’s mission statement reads, “Transportation as reliable as running water, everywhere for everyone,” he will make that happen.

As my dad learned playing tennis with him, and as I have been reminded time and again, thinking about competing with Travis Kalanick? Good luck.

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Staying Safe(r) Online.

In light of the celebrity photo hacking debacle over the weekend, we sent an email to some of our investors, partners, and friends this morning. The more we thought about it, the more we realized that a broader audience could benefit. So here is a version…

Dear Friends,

We saw how ugly it can be when hackers get into your private pictures and emails. In addition to having very long passwords/passphrases, here are five concrete things you can do to make sure this kind of privacy invasion is less likely to happen to you or any of your pals/family:

1) Email – It goes without saying, use Gmail. Turn on what’s called “Two Factor Authentication” for your Gmail account. With that in place, when you want to log in to Gmail, you enter both a password and a secret code generated by an app on your phone. No hacker can get past that, even if they guess your password. (Well, other than the NSA.) Go here for directions on how to set it up: google.com/landing/2step/ If your business isn’t already using Gmail/Google Apps, it is time to make the switch. It’s the most secure platform.

2) iPhone – turn on “Two-Step Verification” for Apple as well. Same idea. Whenever you need to enter your iTunes password, Apple will also send you a text message in that moment with a secret code. Type that in and you will get access to Apple. This matters because so many of your photos are in iCloud and Photostream, though researchers have revealed that Apple doesn’t actually protect photo backups using two factor authentication. That is disastrous and will hopefully be fixed ASAP. Meanwhile, you can still follow the steps here: support.apple.com/kb/HT5570 (If you use an Android phone, be sure to install Lookout: https://www.lookout.com/android)

3) Dropbox – If you use Dropbox to back up photos and documents, they have the same feature. Log in to your account and click on your name in the upper right to open your account menu. Then go to “Settings.” From there, select “Security.” Under “Two-Step Verification” click “Enable.” Then “Get Started” and follow the instructions.

4) Twitter – Instructions on setting up Twitter’s “Login Verification” are here: https://blog.twitter.com/2013/getting-started-with-login-verification

5) Facebook – Here is their “Login Approvals”: https://www.facebook.com/note.php?note_id=10150172618258920

Please note: each of these solutions will provide you with some backup codes just in case you lose your phone or phone settings. It is crucial to print them out and keep a paper copy of these (not a digital copy) in your safe at home. If you get locked out of your services, you may need these paper codes to manually get back in. Please print these out and store them safely. You will be sad if you don’t.

Also, consider using a two-factor authentication app like Authy or Google Authenticator to keep all of these profiles organized. They can also sync across devices if you have multiple phones or might be on a tablet without text messaging service.

All told, there are a bunch of other services that enable this kind of extra security now. WordPressYahoo MailMicrosoft AccountsLinkedIn, and Stripe are some big ones. But the five listed above tend to cover where all of our most sensitive data and content reside. The most complete list of other services using two factor authentication I have seen is here: https://twofactorauth.org/.

As I am sure you know, it’s not really about whether you have steamy photos on your phones. It’s about maintaining maximum privacy and control over your life. So much information lives on these devices now. Personal addresses, bank information, family matters, kids’ stuff, passwords to other sites, medical questions, etc. Skilled hackers can be relentless and their genius at devising new ways or breaking security features is almost eerily impressive. Using very strong passwords and taking the steps above will be a very strong step toward making sure your private stuff stays private. However, above all, please be smart about what you put in the cloud and realize there is always a chance it ends up in the wrong hands.

(Note: all security geeks, nitpickers, whitehats, etc. I love and admire you. You make all of this stuff work so well. You find the ridiculous corner cases and engineer against them so that we can stay safe. Thank you. However, this post is not intended to be an all-encompassing treatise on security. I just think we can agree that if more good people take these reasonable steps they will likely be in much better shape. Cool?)

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Four guys who deserve to win a Crunchie.

It’s flattering to be nominated for any award, let alone a Crunchie. I mean, these are the geek Oscars. I even picked up some fresh dry cleaning to wear to the show.

But, it doesn’t make sense to include me on a list of finalists for Angel of the Year. Put simply, I am not an angel. Lowercase is a family of funds that risk some of my money paired with lots of money from my investors. I am also not the only guy here after we recently hired Matt Mazzeo as a partner in the firm.

True angels are accountable only to themselves and their portfolio companies. They put their own cash on the barrel and know that if they lose it all, they don’t have anyone or anything else to blame. It’s entirely on them.

A few years ago, a class of investors called superangels emerged. Generally speaking, we raised small funds to match our own dollars and wrote checks to startups that were larger than those from traditional angels. These scrappy, understaffed funds still feel angel-ish to me. But, once a firm starts investing bigger checks in later stage deals, like we have done at Lowercase, I am not sure the angel moniker still applies.

On the other hand, I also wouldn’t begin to be named a finalist in the VC category either.  Those guys listed are all first-rate company-builders. The work that gets done at a Series B or C is very different from what we do at the seed level. It’s an entirely distinct form of efficacy, scale, and execution that my peers and I don’t deliver. So, no Crunchies with my name on them this year.

Nevertheless, I think each of the four other finalists for Angel of the Year is worth a shout and recognition for their impact on startups:

Mike Arrington – Sure Mike has a fund behind him now, but to get to that point, he risked a hell of a lot of his own money and well before he had seen any liquidity from the sale of TechCrunch. He backed up his talk with plenty of walk and ponied up his own coin to get into deals that moved him. More importantly, we can all agree that Arrington catalyzed a community from a loose and scattered mess and taught so many of us the language and process of this entire realm. It’s unnerving to consider what angel investing would look like without Arrington’s impact on the space.

Chris Dixon – Probably the most authentically angel-ly of the bunch, Chris always tends to find his way into extremely solid companies and has developed a strong reputation for being helpful to his entrepreneurs. His blog is incredibly rich and evidences how selfless he is with his time when it comes to educating new entrepreneurs and investors. He is also due credit for being one of the most ardent and unwavering fans of the NYC tech scene. Yet all this aside, I think it is most amazing to consider that he has accomplished all of this while busy founding, leading, and exiting his own startups as well. He is the real deal.

Paul Graham – No single person has had more impact on the creation and financing of tech startups than PG. Period. The YCombinator revolution emancipated the engineering class from servitude to MBA overlords, demystified the art of company-founding, and made huge leaps toward democratizing access to capital. I could go on, but we all already know how lucky we are to have Paul.

David Lee – This guy has only recently started to get the credit he deserves. Of course, he too is investing a fund’s money, and doing it very well at that. He also has started blogging more regularly and his pieces are invariably thoughtful and worthy of any entrepreneur or investor’s time. However, take an extra moment to consider the sheer gutsiness of the Start Fund, a project he created. By ensuring that an entire class of companies automatically had the funds necessary for months of operations and growth, David brought a previously unforeseen level of accessibility to startup capital. At the most crucial stages of a company’s life, thanks to the Start Fund, founders could focus on product and not be distracted by the harrowing burden of fundraising so early. That in itself is an entrepreneurial move and it makes me happy to see people recognizing David’s impact.

I will be excited and grateful when they call any of these guys’ names at the Crunchies. The startup world is a better place thanks to each of them. As for me, don’t you worry. Alexia assures me that a Western Themed Investor Attire category will be included in the voting any day now.


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WANTED: Cowpoke/Intern

[Update: The job has been filled. But, stay awesome.]

So, it turns out that managing a portfolio of thirty-nine companies, a couple of secondary vehicles, and two private equity fund partnerships is time-consuming. Who knew? Result is that there are lots of loose ends at Lowercase just begging for knots. Thus, we seek an intern with tiny, nimble fingers.

There is no formal set of requirements, many of the responsibilities will be up to you to propose, and the position will be mildly compensated. “Mildly” meaning on a heat scale ranging from Sweet Bell peppers to Habaneros… ketchup. You can perform your Lowercase duties from anywhere in the world, and this is non-negotiable, for the most part, usually, kind of. The prospect of a field trip to visit Lowercase HQ in Truckee should worry you a little bit, but you will nevertheless rehearse your best Real America colloquialisms and be ready to wear a “My kid shot a deer while your honor student was in school” shirt if survival requires it.

Broadly speaking, your professors/bosses consider you brilliant and therefore turn to you for help managing their Facebook privacy settings. (Having actually successfully reset them is not a required skill.) You have strong opinions about new tech products, are ultimately wrong more often than you are right, and are proud to admit so to everyone except the TechCrunch journalist you called a “sycophantic fanboy douchebag” in the launch post comments. You know exactly how Google could win at social if you could just get Eric, Larry, and Sergey to return your damn emails, and you have tattooed three potential business models for Twitter on your inner thigh. You can foresee how Groupon will be retailing human organs by Q3 2011, and you have asked your parents to stop calling you on Sundays and instead submit their questions to you via Formspring.me.

By this point, your copy of Excel should have a Pavlovian desire to please you, and of course, you have a pet name for it. You have considered if and how spreadsheet macros could solve the climate crisis and you have already begun coding them. You’ve gotten to second base with HTML and PHP, even better if at the same time (you animal). Your business-y friends tease you for being a geek, but your money-allergic nerd friends bust your chops for being a greedy sellout and they write open source rallying cries on your forehead when you pass out. You have considered whether there is a mass market for Fred Wilson, Chris Dixon, Ron Conway, Brad Feld, Josh Kopelman and Dave McClure trading cards, and even if you decided there isn’t, you printed yours anyway.

You refer to people by their Twitter handles first, and find every third sentence from the old lady who lives next door to be OH’able. You have submitted at least one word to the Urban Dictionary and you’ve said “stack that cheddar” to someone 20 years your senior. You believe that golf is the old golf. You can immediately tell if you have stepped in a new meme and have it all over your shoe, and somewhere bit.ly has data showing you are Patient Zero for viral links. Gary Vaynerchuk and Kevin Rose order whatever you’re drinking, Tony Hsieh calls you when he is feeling unhappy, and Tim Ferriss has given you the password to his inbox.

You’ve had a tipping job, or dug ditches, or dug ditches for tips. You’ve traveled extensively abroad and can say “What is your Wi-Fi password?” in over 10 languages. You have a hobby or an interest that has likely put you on a government watchlist, and you’ve responded by putting the government on your watchlist. You play sports more than you watch sports on TV (partly because you think TVs are quaint anachronisms), and you likely grew up somewhere that when you mention it to others you have to follow it up with, “No. Really.” You wish the Dos Equis guy would post his 23andMe results with you to see if you really are related.

To apply, send us your resume, a bio, a general statement of why the hell you would want to sully your reputation by being associated with such a sordid outfit as Lowercase, and what three things you would do if you were in charge of Fanbridge, Twilio, and Posterous. Lastly, to insure you have actually read this far, and if you have, I probably owe you an apology, please include a link to your favorite cowboy shirt made by Scully. Bundle all of this up in a digital saddlebag and Pony Express it to: [the job has been filled for now…]

Thanks, all,


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