It's time for me to start writing again.

I've started starting a few times over the years, but it hasn't stuck yet. I'm hoping 2019 is the year it finally takes hold.

I used to blog regularly early in my career, but stopped around the time I launched Formspring. That led to the busiest years of my life to date, which was a good excuse for me to stop writing.

And for a long time now, I've regretted stopping.

Yes, I got busy. But more than anything it's been my insecurities that have held me back from writing more. What can I really contribute in yet another blog post about rehashed topics? Why would anyone care to read my drivel? Why not keep my thoughts to private conversations and personal journals?

But I've noticed a difference between writing in a journal and writing for my blog. There's something powerful in how publishing forces me to think more deeply about what I've written. And there's something magical in a post sparking conversations I wouldn't have had otherwise.

My blog has been instrumental in helping me learn and grow, and I've missed that.

So here I am again, blogging.

The new year is a good excuse to make me take that first step. And maybe sharing my goal publicly will make it harder for me to use "too busy" as an excuse.

Thanks for reading. And thanks for helping me learn.


[Originally posted on Medium]

Look, I get it. Trump won.

I accept it. I’m not whining. I’m not rioting.

And I get it. There are millions of working class people across the country that felt left behind in Obama’s America. They wanted change.

And I get it. It wasn’t about race.

And you especially, I don’t think you’re racist because you voted for Trump. Truly.

But please don’t insult my intelligence by telling me that race wasn’t part of Trump’s campaign.

Please understand why as a black man I’m scared about the next four years in Trump’s America.

Am I supposed to forget that he spent years on the national stage as the leader of the birther movement?

Am I supposed to forget that he started his campaign labeling Mexicans as criminals and rapists?

Am I supposed to forget about all the other times he used racially tinged rhetoric on the campaign trail?

Am I supposed to forget what he said about Judge Gonzalo Curiel?

Am I supposed to forget what he said about the Central Park Five?

Am I supposed to forget all the times he retweeted messages from white supremacists and neo-Nazis?

Am I supposed to forget he hired Steve Bannon, a pivotal figure in the alt-right community, as CEO of his campaign?

Am I supposed to forget his calls for banning Muslims?

Am I supposed to forget his calls to bring back stop and frisk?

Should I go on?

Or did I miss the time that he apologized for any of these things? Where he reached out to the disaffected to clarify his position?

Or did I miss the time when he clearly denounced the acts of intimidation and violence against minorities carried out in his name?

Don’t think I’m pacified because he added Ben Carson to his transition team.

Don’t think I’m pacified because you point out something racist someone else said or did, someone who’s not going to be our president.

Don’t tell me Trump only said horribly racist things and appealed to white nationalists just to get elected. That he didn’t really mean those things.

Don’t tell me he’s really going to be a president for all the people.

Don’t tell me to deal with it.

Don’t tell me to shut up.

That, I do not accept.


[Originally posted on Medium]

“Well, once there was only dark. You ask me, the light’s winning.” — Rust Cohle, True Detective

The default state in any growing organization is chaos. The chaos of trying to integrate new people into the culture. The chaos of trying to align everyone toward common goals. The chaos of communicating what everyone’s working on.

In the chaos, it feels like the organization is falling apart. You remember how things were so much better back in the day, when everyone could all fit around the same table at lunch. And reading about other companies, you’re convinced everyone else has it all figured out but you.

The problem is that as a company grows, you can’t rely anymore on serendipity to solve communication problems. Metcalfe’s law is working against you — at 5 employees there are 10 lines of communication between each person. At 10, there are 45 lines. At 20, there are 190. By 50 employees you’ve crossed 1,000 lines of communication — chaos.

The good news is that if you’re able to get anything accomplished as an organization amidst that chaos, the light’s winning.

This doesn’t mean it can’t be better. It probably should get better.

The first step is to understand that chaos. Then tame the chaos by designing your organization’s communication protocols in a way that works through it. TCP, not UDP.

As Metcalfe works against you, you’ll have to create processes around deliberate, structured communication. Maybe that’s adopting OKRs, making your daily standups effective, or creating weekly reports and presentations to share internally. Find the nodes and connections that are left in the chaos, and be deliberate in how you communicate to overcome it.

The light will win.


Lessons learned building an anonymous social network

[Originally posted on Medium]

I built Formspring. For a while it was the fastest growing social network in history, but ultimately ended in failure. One of the defining characteristics of Formspring was that users could send questions to each other anonymously. There are a lot of reasons why we grew quickly and why we failed as a company, but it’s clear that anonymity was a significant contributor on both fronts.

As apps like Whisper and Secret have launched with early success, it’s likely that we’ll see more entrepreneurs experiment with products that incorporate anonymity. I think it’s worth sharing what I’ve learned in the hopes that it’ll help other entrepreneurs avoid some of the problems Formspring ran into.

Anonymity can be a good thing

I should lead by saying that I think anonymity can be a good thing. At Formspring, we spent a lot of time thinking and talking about ways to encourage expression. One of the reasons why I built Formspring in the first place was that I felt like the standard model for social interaction (aka Facebook) felt too rigid, too forced, too unnatural — it forces constraints on communication that don’t have any parallel in the offline world. Do I walk around with a name tag that shows you my birthday, my interests, and pictures of my mom?

Anonymity (and pseudonymity) is important because it’s part of how we naturally interact with others. We don’t have one “real” identity—we hide and reveal different dimensions of ourselves depending on the context of who we’re with and what we’re doing. Even more to the point, many of our interactions start off anonymously before growing into a relationship that’s structured by identity. I can strike up a conversation with a stranger between BART stops, stand up and ask a question during a conference Q&A session, or jump into a pick-up basketball game—and find those interactions rewarding without establishing my “real” identity ahead of time. It’s good to have equivalents to this online.

Of course, the problem we struggled with at Formspring was finding the right balance between all the ways that anonymity can be used in constructive ways without devolving into a product where anonymity is only used to say hurtful things about others. It’s tough, but I don’t think it’s impossible. With the right product and community mix, I think anonymity can be a very powerful tool for encouraging dialogue and sparking relationships. We saw incredible things happen on Formspring that wouldn’t have happened without anonymity—from the countless new friendships created around common interests, to support groups that formed to deal with difficult issues.

Fight perception early

One of the problems we faced is that it’s easy for people to instantly equate anonymity with abusive behavior. While anonymity can certainly breed abuse, it’s not necessarily the case. And it completely ignores the fact that abuse is rampant on apps that discourage anonymity.

In cases where we saw someone being abusive or being abused on Formspring, it was almost a given that we could find similar behavior on Facebook or other apps where that user spent their time. And sadly, we would frequently hear heartbreaking stories of abuse that was happening offline as well. The problem with bullying is bigger than any particular technology, and the solutions are much more complicated than might seem on the surface.

Given this, it’s not only important to find the right ways to discourage abuse, but to fight public perception early. Because people equate anonymity with abuse, it’s so much more important to get ahead of the conversation by being explicit about your vision for how anonymity should be used in the product in positive ways. I wish I would’ve tackled this much earlier at Formspring.

Perception is important for a lot of different audiences—employees you’re trying to recruit, partners you’re trying to work with, law enforcement, policy makers—but it’s most important with users. If users can’t see your vision beyond being a utility for posting abusive content, then it’ll be hard for the service to become more than that. That vision will need to be obvious as they explore the product, and in how they hear about the service from others.

Perception is probably most difficult in the press. Unfortunately, sensationalist headlines and soundbites work better than a nuanced discussion of complex issues. So it goes. This makes it even more important that your vision be clear to the public early.

The first mainstream media stories written about Formspring were about bullying. We hadn’t told our story well before that, so even as we worked on incredible things afterwards, it was was hard to overcome the initial perception about the company. When people read about abuse happening on Facebook, they already knew it as a place to see pictures of their grandkids. Without any context, a story about abuse happening on a new anonymous social network only cemented the impression that the purpose of the product was to encourage abuse.

Solve for long-term engagement

It’s hard enough for anyone to build a social app with long-term engagement, but anonymity introduces some unique problems.

Where anonymity was being used for abuse, we found that engagement had high amplitude but short wavelength. Like with any service, salacious content resulted in more activity in the short term, as users jumped into conversations to attack or defend each other. But most people don’t enjoy spending their time that way long-term. It’s easy to get burnt out and abandon the service forever. So combating abuse is not only the right thing to do, it also makes good business sense towards ensuring users stay engaged long-term.

Another problem anonymity poses for engagement is that it might create an unnatural barrier for continuing conversation. It’s easy enough for me to exchange phone numbers with the stranger I met on BART, but hard to reach out to the anonymous poster that seemed particularly interesting to me. That ability to shift modes of conversation can be helpful in keeping people engaged on the service long-term. It really depends on the core problem you’re solving, but most users aren’t looking for an anonymous utility—they’re looking for ways to express themselves and interact with others.

Work with the right people

The best advice I can give is that as you work on the policies and products to help shape the community, work with people who’ve dealt with these issues before. Even though I’d had a decent amount of experience working on sites with user-generated content, users used Formspring in ways that surprised me.

It’s easy to find people with strong opinions on product and community, but so often the things that sounded right at first weren’t really effective or had unintended consequences. Though we tried a lot of things early on, we didn’t get much traction addressing abuse until we started working with people that had direct experience working on these issues. Most often, they were people that spent their day thinking and learning about the type of problems online communities face.

It’s incredibly challenging to build a healthy community at scale. As challenging as it is, it’s harder still when anonymity is part of the product. Because of this, most people will tell you to rip it out. Investors will pass on your company, peers will criticize you, parents will yell at you. Maybe they’re right. And maybe not.

The best policy people I worked with understood the vision I had for Formspring, and why anonymity was part of that. They didn’t try to strip out everything in the product that made it unique, but worked with us to figure out how to fulfill that vision while building a healthy community.


Thanks to @sacchetti for encouraging me to write this, and reading an early draft.

Finding the "Right" Idea

It's hard to figure out whether your idea for a startup is the "right" one. If you're on the verge of starting a business, chances are you're starting with a few (or dozens of) viable ideas, and weeding the list down to one is a daunting task.

Of course, I don't have a magic formula for figuring out the answer, but there a few things I've observed that I think one can do to help increase the odds for success:

Ask Yourself

I think the best idea is one where you can answer honestly that you'll use the product yourself (and if you'll charge for your product, that you'd pay for it). Don't answer this as a hypothetical "you" in an alternate universe — ask whether you would buy this product today to solve specific problems you currently have.

Similarly, if you're in a role where you're frequently asked to make product recommendations or buying decisions for other parties — ask yourself whether this is what you would select for your client.

This certainly isn't the only criteria to test whether or not an idea has a chance for success, but it leads to a well-established pattern: 37signals created Basecamp so they could manage their projects, FreshBooks was created so they could invoice their clients, MailChimp was created so they could send email campaigns for their clients, and I created Formstack because I had to build online forms for my clients.

Ask Others

Neil Patel's advice is to quit asking people what they think and just start implementing. He's right — most people won't really know whether your idea will work or not. And those close to you are apt to try to make you feel good by saying your idea is the best thing they've ever heard, even if it sucks.

However, I still think you can get a lot of value by talking to people you know that fit your target market to get a sense for whether or not the problem you're trying to solve actually exists. Focus your discussion on the problem you're solving, rather than your idea itself. Most people will open up truthfully about how painful a particular problem is for them, and you might get a sense for why existing companies aren't already solving that problem.

Ask Your Market

Finally, before you spend time and money building out your idea, test it out to see whether a market for your product really exists, and gauge how hard it will be to generate leads and sales. Launch a fake AdWords campaign, as Eric Ries describes here — something that you can do quickly for less than $50. Unless you're launching rockets, it's probably going to be much harder to get enough customers to spend money on your product than it will be for someone to actually build it.

[Updated references to Formstack to prevent confusion about the name change]