Instagram Stabbing Itself By Leaving Twitter Cards Off

YouTube never disabled embeds on Twitter or Facebook, letting visitors to those products watch a YouTube video without ever coming to our site. YouTube worked with Apple to make our app a default experience on iOS, even leaving it effectively non-monetized until last year. Why? Because we knew our users were on those sites and we wanted YouTube to be synonymous with “video.” Because we knew we could create a differentiated on-site experience which drove clicks back to our site from those embeds. And because we knew that our community was OURS only so long as we served THEIR needs.

Instagram photos ceased being viewable on Twitter last December due to a strategic decision by Facebook management, which Twitter CEO Dick Costolo said was “their prerogative.” At the time Instagram was building out a web presence and seeking overall to drive more consumers to view photos within Instagram controlled properties (their website, their apps), rather than through Twitter. Since that time Instagram has continued to grow – 150 million user now – so everything seemingly is healthy. But is it?

What Instagram gave up, in my mind, was owning the word “photo” on Twitter. I spend a lot of my social tech time on Twitter and anecdotally see far fewer Instagram links than I used to. Or maybe it just feels that way since I certainly click on fewer than I did when the picture was embedded right there. These days “photo” for me on Twitter could mean their own native hosting, or FrontBack, or imgur, or any number of other destination links.

Twitter is reportedly getting ready to release a new app UI which puts more emphasis on media. It would be a shame if Instagram pictures still aren’t viewable within Twitter’s native app, and an even more glaring absence since I’m guessing “photo view” wouldn’t even include Instagram URLs.

If Instagram turns card support back on after Twitter launches the app it’ll be made into a big deal by the tech press (“Instagram Gives In”) so why not just do it now. Reverse a decision made when Facebook stock was below IPO-levels.

Letting me view Instagram on Twitter doesn’t commoditize the service, it keeps Instagram top of mind.

AngelList Syndicates Will Also Pit Angel Against Angel

Jason Calacanis thinks AngelList Syndicates will hasten the death of the worst performing VCs by further commoditizing capital and giving super angels more $$ to put into deals. I’m a big fan of AngelList (#investor) and Syndicates are going to change things dramatically (previous posts).

One aspect that hasn’t been discussed much is how they now make the angel environment more competitive as well. Before as a founder I might have been able to get both Dave Morin and Kevin Rose into my deal, offering them each $50k slugs. Now they each represent more than $300k in syndicate dollars. Does that full slug get invested into each deal or can they pro rata down? If not, all of a sudden the $250k in the round I set aside for strategic angels doesn’t get me a few value add folks, it makes me choose which syndicate do I want to include. Angels, who previously collaborated, now might be competing?

My guess is there are also some angels who were popular when they represented a $25k check but won’t be as sought after if they try to push $300k into a round.

Over the last few days there’s been a lot of momentum with angels starting to raise their Syndicate dollars. Maybe an angel differentiation before too long will be LACK of a syndicate so that they can put an easy $25-$50k into deals.

VCs Should Give Honest Feedback & Why They Often Don’t

As a new venture capitalist, I’m still refining my approach but when I read an investor attesting “very seldom do VCs give you the real reasons for passing to keep good terms with you for future investment optionality” my eyebrows raised. At Homebrew we try to always give specific feedback when we pass on a deal. We do this out of respect for the founders and the time we’ve spent together – even if it’s just one meeting – but I’d hope this behavior brings us closer to the entrepreneur. A soft pass shouldn’t result in optionality; a clear, honest relationship should.

My POV was met with some public and backchannel comments – from entrepreneurs wondering whether we’d still give feedback if it was a founder issue, not a business plan concern; from a good friend and fellow VC sharing that he had wanted to take this approach too but was finding it difficult; and another entrepreneur suggesting VC feedback is worthless, just tell them “yes” or “no” and move on. Let me try to address these in reverse order….

1) VC Feedback is Worthless

One of the things I love about my job is learning from founders during pitches. They always know at least one thing I don’t, and often it’s much more than that. At the same time, I possess data that can be useful to them: I hear many more startup pitches than they do; I’ve probably seen variations of the same idea pitched by other people; because of my operational background, I have some experience relevant to their company building. For me to spend minimally 30 or 60 minutes with them and not reciprocate, after they’ve just passionately told me about what they’re spending 100 hours a week building, well, that seems wrong.

Here’s what I try to do: couch my feedback with the admission that they’re closer to their market and the problem they are solving. Let them know that I respect their ambition and passion. Then, as articulately as I can, give them feedback on the pitch, their hypotheses and some of the things they might want to keep in mind. And, most importantly, I say “I’d like to talk more,” “I don’t think this is right for us” or “it’s too early for us. here’s what we’d like to see happen first and I understand this means you may close the round without us.”

I’m not sure that I always do this as elegantly as I’d like. Maybe sometimes I’d be better off just saying “oh we love it but really too busy right now to go deeper. Let’s catch up again in a few weeks” (and I’m probably guilty of doing this a few times). But I just don’t believe Homebrew is going to be successful if we don’t stick to our personal true north: building the type of fund that WE would have wanted to take money from. If you’re a founder and you think investor feedback is worthless you’re (a) talking to the wrong VCs or (b) not getting all you can be out of the time spent fundraising.

2) Giving Feedback is Difficult

Yes it is. It takes time. It can sometimes be perceived as re-opening the conversation (note: often a “no” is no, and not an opportunity to objection handle). But I think it’s really important to stick to your principles – if giving feedback is a principle, do it. If it’s just a strategy, it’ll probably ring false anyway. I’ve decided that my approach probably won’t improve my standing with someone who has already decided they don’t like me, but that for those who do appreciate me, it’ll bring us closer.

3) But What If It’s Personal?

Let’s be honest – at seed stage 99% of the time it’s personal. You’re betting on team more than anything else. We’ve looked at 400+ opportunities over the last two quarters and in only one case did we get far enough to pass based on “amazing team but we hate the market.” I don’t equate passing because of team with “bad founders.” Everyone we meet with who is starting a company is already someone special. To try and build something which doesn’t yet exist takes guts, drives and skills that are not average. To reject the path of “get a job and hold on to it for as long as you can” – that’s awesome. So what are the types of “pass based on team” that we do and how does that feedback sound?

  • Founders Not Mission-Driven: The “why” matters to us as much as the who, what and how. If I think the why is missing from a pitch, I might say “doesn’t resonate with us why this particular team is working on this problem and we really like to see mission-driven founders.”
  • Founder Skill Match for Problem: Be upfront that we think there’s a hole in the team that we’d want to see filled via key hire or at least strong pipeline before we fund. I’ll very soon be able to show a real example of this where we led the funding round for a team after watching them bring on amazing talent during the fundraising process. Skill match might also be about level of experience/familiarity with the problem they’re trying to solve.
  • Lack of Personal Connection with Founder: This is probably the trickiest but needs to be addressed. If there’s someone that I just don’t connect with during the fundraising process it would do both of us a disservice to try and work together. In these cases I say “we’re just not connecting and I don’t think it makes sense to work together.” It’s not that the founder did anything wrong per se. Equally so, the VC really really really needs to make sure their aren’t any unconscious biases at work. If they can’t seem to “connect” with founders from underrepresented groups, that’s their problem. Not just on a personal level, but they’re going to miss a lot of good investments. Similarly you don’t need to be best friends with all your founders. It’s not about can we bro out together, it’s about how each party reacts to feedback, to tough conversations, to the mutual commitment being made.

I’m a new VC with six investments so maybe my glass is half full and my view of the world is unreasonably rosy. But as a product leader, working for startups, angel investing/advising a bunch of founders, and just being a human being, I’ve always benefitted from and tried to contribute to, the exchange of feedback.

The only thing more dangerous than what is spoken is what goes unspoken.

Syndicates Gives AngelList Insight Into Finishes, Not Just Starts

Naval confirmed that with Syndicates, AngelList will, over time, show potential syndicate investors the track record of the syndicate lead – how good an investor they are.

1. It will prevent syndicate leads from cherry-picking – ie only syndicating deals where they want to diffuse the risk.

2. AngelList only had start info before – the terms that the round was raised. With Syndicates they start to collect info on exits.

That’s awesome.

Realtime Is A Trap & The Past Is Underrated

Faster realtime data is great for machines but largely distracting for people. Realtime is a trap. The most recent tweets you’re reading aren’t necessarily the most relevant ones you could be looking at. Give people two magazine articles about evergreen topics – one with a recent timestamp, the other a few months old. Most will tell you the newer is more important, more interesting. Take it further – put two different timestamps on the same article – one today, one six months ago. I bet the “newer” one has more engagement and more sharing.

When Apple livestreams a product announcements, 99% of the people watching or reading liveblog are wasting their time. Unless your job depends on gaining access to Apple news as quickly as possible to make immediate business decisions, you should just be waiting for the summary.

Machines love realtime data. They can sort, process, compute with little tax. People on the other hand are being lead astray. I’m no different – I’d probably be shocked to know the total amount of time I spend in Twitter each day. The 1-2 snacks that add up.

What can we do as technologists, as humans? Contemplate “slow media” – other mechanisms to drive engagement and habit besides increased information velocity? Stop undervaluing archives – novel ways to expose less recent but highly compelling content to audiences? Self-control – turn off notifications, close the background tabs.

This isn’t a screed against multitasking, or social media, both of which I enjoy. It’s a question about a cognitive bias being exacerbated by our current product design.

AngelList Syndicates: Three Examples of Their Powerful Future

AngelList recently started supporting syndicates, where a lead investor into a startup can solicit for other investors to join them in exchange for carry on the deal (a share of their profits). Some speculated that syndicates would immediately compete to disintermediate traditional VCs and while this may be true over longer periods of time, I’m thinking syndicates nearterm will be more powerful in other ways. Here are three examples:

1) The New Placement Agent: Essentially AngelList on steroids. Let’s say you’ve gotten direct commitments of $1m in a $1.5m seed round. Rather than try to round up an additional $500k in $10-$50k checks via individual LPs on AngelList, you use one of a new class of AngelList Placement Agents, who can round of that amount into a syndicate. These new Placement Agents would be a new type of intermediary who knows how to leverage AngelList, not just a rolodex of high net worth individuals. Benefit to entrepreneur is faster fundraising and single LP on cap table (since syndicates perform as a LLC) so they might start to move their more passive angels into this structure as opposed to direct investment.

2) Giving SuperAngels More Deal Leverage: There are a class of angel investors or technologists whose reputation and value-add exceed their bank account. Today these folks might write a small check as part of an investment and also get advisory shares but the leverage model still isn’t great. With syndicates, they can tell a startup that their involvement is tied to getting a larger chunk of the deal and filling via AngelList. This gives them upside on the carry without non-paid in capital dilution that advisory shares would otherwise bring. It wouldn’t surprise me to see some of the best individual angels “professionalize” in this manner – rather than raise a fund or become scouts for Sequoia, just do a few syndicates.

3) Going Where VCs Fear to Tread: Porn, marijuana, and even, gasp, internationally-based businesses. These are just some of the categories where startups have trouble raising seed rounds from US-based early stage VCs. I frequently get emailed from friend-of-friend founders in Japan, Brazil, Canada, Europe, etc who are wondering which seed stage US funds will invest abroad. The answer is very very few. But on AngelList, a “flash fund” can be created using a syndicate. Individuals with country-level domain expertise or ties to very specific industry verticals will be able to rep these deals now on AngelList.

So overall I’m very excited about AngelList’s continued movement towards open investment platform and expect syndicates to have a market-expanding effect as opposed to being competitive with VCs in the nearterm.

Look for Advisors Who Can Teach, Not Tell

Earlier this week, a newly funded founder and I were discussing advisory board strategies. Specifically the value of individuals with specific operational expertise (as opposed to industry domain expertise/relationships). One of the characteristics we identified as a filter was to seek advisors who could “teach, not just tell.”

The founder wants to fill in around his expertise with advisors who can help guide him and his team in areas such as distribution. Teaching, not telling means people who can share frameworks, formulas and programs that can be modified and reused. It means having an advisor sit down with a team member and perhaps provide training wheels through a real world scenario. It doesn’t mean having the advisor become part of your org chart or solve your problems for you. If you want that, create a separate consulting agreement.

By teaching, advisors create lasting impact extending beyond any limited-period direct involvement. They uplevel you and your team. This is one reason in building Homebrew’s entrepreneur advisory board we’ve focused on cultural fit and subject expertise. I’ve watched Andy Johns, growth guru of Facebook/Twitter/Quora, teach his framework, not just tell stories about his past successes. That’s real value.

When Google Went Public … (Twitter IPO)

Fittingly it was with a tweet that Twitter announced the filing of a S-1, the first formal step towards an IPO. The document remains confidential so debating their financials is nothing but a speculative argument at this point. Twitter has become my most important social messaging platform, a place where (as @hunterwalk) I’m able to share ideas, find new interesting voices, discover great content and get a snapshot of what the world is thinking. I use other products but I live in Twitter.

The reportedly 2,000+ Twitter employees must be thrilled about this next phase of their company. Besides generating incredible wealth for many of them, being a public company is both a symbolic step towards becoming indelible and a very real milestone with both benefits and costs.

I arrived at Google in late 2003, prior to our S-1 being filed in April 2004. There was already lots of internal and external speculation about our trajectory but until the document went public, no one understood just how powerful a business model the company had created. During my interview process Google HR was very secretive about the value of my equity. In fact they told me only the number of shares I had been granted. Without knowing the number of shares outstanding or the enterprise value of the company, a grant total was totally useless but they essentially said “trust us.”

What changed once we went public and how might these same shifts impact Twitter?

  • Data Got Locked Down: Before our IPO Google was notably open with its data internally. There were many ways to access near realtime revenue and other tools we could use in the course of managing daily business. With the public offering came regulatory requirements and many of these dashboards went behind authenticated logins, where only certain Googlers could access based on job needs. If you filed for access there was often a delay in approval. Larry, Sergey and Eric remained committed to being as open as possible but the days of our sales chief standing up at Friday meetings and announcing revenue for the quarter were obviously over. Google has done a remarkable job of remaining transparent internally but with a stock offering comes certain changes that are non-negotiable. If they haven’t already, Twitter employees will soon find themselves partitioning tools and data by function
  • Public Currency for Acquisitions, Hiring: Whereas all stock to this point as been speculative — it *might* be worth something in the future — liquidity in the public markets means Twitter will have a strong weapon for more acquisitions and hiring candidates. Not necessarily the employees who want the IPO pop (more on that below) but they can put together packages which match the current expected value of one’s current employer. From an acquisition standpoint it will be interesting to see whether Twitter uses cash or stock. Stock is cheap now but expensive later if you believe the share price will rise. Google historically pays cash, although there were notable examples such as the YouTube deal.
  • A Different Type of Employee Gets Hired: It’s silly to say that Twitter will no longer be a startup once they IPO. The reality is they’re not a startup now — risk is off the table, thousands of employees, hundreds of millions in revenue. Post-IPO though there’s a psychology that seems to impact potential hires — you start getting fewer risk takers applying and more careerists. This isn’t absolutely a bad thing — hiring more experienced leaders is important for a company’s stability and Twitter has certainly already raided lots of Google talent to build its management layer — but it does start to change the personality of the company. People would sometimes ask me if post-IPO did Google start hiring “B+” talent instead of “A” (the assumption being that the best people would no longer want to work at Google). My answer was a definitive NO. We still hired “A” quality people, it was just increasingly a different type of smart. More pragmatic, more about scale. Our founders worked hard to maintain the culture and I think much of Larry’s first few years as CEO has been about returning to what he remembers Google being in the early 2000s. Twitter CEO Dick Costolo and his team will have the same challenges — some old timers memorializing “the old days” while also realizing that Twitter 2014 cannot be the same as 2008.
  • Flight of Talent: There’s usually a burst of departures in the six months after an IPO, then it kinda returns to normal levels. Lots of fully-vested “old timers” leave. Since many Twitter employees are sitting on heavily appreciated stock options, a public offering will finally give them the liquidity to sell shares. Important to note this isn’t just about getting cash in their pocket, it’s about getting cash to pay the IRS for the tax burden that would come with exercising previous stock grants.

Having many friends at Twitter I’m obviously happy for the company. As a Twitter user it’s bittersweet because while this IPO will increase the stability of the company, it also will continue to push them to seek growth which may evolve aspects of the product I love so much.

When Google finally went public in August 2004, after a long and weird registration process, there were a few minutes of clapping, high fives and private calculations of net worth. Then we all went back to work.