How To Bulletproof Your Reputation In The Digital Age


“I date younger men… Predominantly men in their twenties… And when I date younger men, I have sex with younger men,” Cindy Gallop shared matter-of-factly.

Except this wasn’t a private conversation with a close friend. It was on the stage of TED’s main conference talking to hundreds of the smartest people in the world and the 800,000+ people that would go on to watch her video. It certainly wasn’t what you’d expect from a former senior advertising executive (49 at the time) and the former chair of the board at international advertising agency, BBH.

Cindy Gallop wasn’t being spontaneous. She was making one of the most calculated decisions of her career as a way to launch her new company, MakeLoveNotPorn.

Many of today’s top entrepreneurial leaders are making similar decisions to Cindy’s. They are deeply sharing who they are and what they believe with the world. Everyone from Tony Hsieh (founder of Zappos), Gary Vaynerchuk (co-founder of Vayner Media), Sheryl Sandberg (COO of Facebook), Jacqueline Novogratz (founder of Acumen Fund), Richard Branson, Jason Fried (co-founder of 37 signals), to Arianna Huffington (co-founder of the Huffington Post) are using books, blogs, social media, and speaking engagements to share their inside world while building their companies as the same time.

To understand why this increasingly makes sense in the digital age, we need to understand the explosion of online reputation platforms.

The Explosion Of Online Reputation Platforms

Online reputation platforms help others understand who we are, what we do, and what we own by organizing and publicly displaying related word-of-mouth. They help individuals make better decisions and facilitate exchanges that would never happen otherwise. How crazy was renting our most sacred space, our home, to a complete stranger before Airbnb!

The platforms that exist now are just the beginning. Every year, we’re collectively doubling what we proactively share about ourselves on social media and what we allow our devices to share about us. Now, for example, it is even possible to put a device in your car that shares your driving information in order to lower your car insurance rate.

We as as a society have not fully grasped the significance of this explosion…yet.

What It All Means

On the popular review website, Yelp, a Harvard study showed that a one-star difference in a restaurant rating impacts revenue between 5% and 9%. If you use Yelp, when was the last time you selected a restaurant with a bad reputation or no reputation? The Yelp for your industry is coming if it hasn’t already. It is impacting what jobs you get, the contracts you’re offered, your admission into schools and programs, and even what friends, significant other and romances you attract into your life.

Every reputation platform seems irrelevant at first. Then, it becomes a nice, useful tool. Finally, it becomes the price to play in the field. When this happens, having no reputation is as much of a red flag as a bad reputation.

Joe Fernandez, the founder of the largest reputation platform measuring influence, Klout, learned this firsthand in October 2011. Klout changed its algorithm in order to improve the quality of the overall score.  As a result, some people’s scores changed significantly. He expected some backlash, but he was in no way prepared for what actually occurred.

First, an #OccupyKlout hashtag was created.

Next, his cell phone was leaked and he received hundreds of death threats.

That’s when Joe realized the importance of reputation platforms. In his words,

In the future, people won’t just have one score. There will be multiple scores and people might live and die by those scores. The good thing about all of this is that social data has been democratized. You can control your reputation. The top ways to build your online reputation are to keep make sure your profile reflects who you are and is up-to-date, to be authentic in how you portray yourself, and to be consistent in what you say.

Here’s what you need to understand about what all of this means:

  • Your online reputation is your reputation.  People are using the first impression they have of you from the Internet to decide whether they connect with you and how they act toward you when they do.

    In short, your online reputation will precede you. Ben Huh, the founder of CHEEZburger, put it like this during an interview I had with him, “I’d like to think that we’re getting into a world where we’re understanding more about the substance of a person rather than just their biology. While we’re no longer in the wild, biology still drives a lot of decision making. For example, you still hear things like, ‘men who are taller tend to rise more quickly in their career’. At its face value, that’s ridiculous, but it also turns out that it’s true. We’re moving away from biology as our first impression. This is actually a good thing.”

  • Who you are in one area will be how you’re perceived in all areas. Reputation platforms scale your reputation. In the past, reputation was solely determined by word-of-mouth in a small community or by our one-on-one interactions. In this context, word-of-mouth diminishes quickly over time and distance. Now, our reputations can be seen by everyone everywhere. It is always a Google search away.

  • Other people can more easily make their opinions of you go viral. Whether online or offline, we ultimately can’t control what other people say about us or the context in which they say it. However, what’s unique in the online world is that it is easier than ever for others to make those opinions widely known. This can be a very good thing or a very bad thing.

The implications of the future of online reputation aren’t innately good or bad. What matters is how you handle the shift.

Thus, a new question arises, “How do we best build our personal reputations in this new age?”

To Play It Safe Or To Play It Real?

In writing this article, I had the opportunity to interview several people who’ve seen the shift coming for years and have found ways to prosper in it. Over the past year, I’ve explored this for myself as I’ve opened up about my life and lessons learned online.

If I had to boil everything down into one idea it comes down to the following words that Cindy shared with me:

If you identify exactly who you are and what you stand for, what you believe in, what you value, and if you then only ever behave, act and communicate in a way that is true to you, then you never have to worry about when anybody comes across you or what you’re found doing, because by definition you are never caught doing anything to be ashamed of.

By publicly sharing her sexuality with the world, a topic that’s an important part of her life and purpose, Cindy is putting a beacon out in the world. That beacon attracts people who ‘get’ her, and it distances or has no impact on people who don’t.

In so doing, Cindy is building an authentic network; a network of kindred spirits around her who deeply value her for for who she is. Kindred spirits are people we connect with at a very deep level and who play a transformative role throughout our life. As entrepreneurs, this means vendors, partners, employees, investors, mentors, and customers with shared values. Cindy has entered a virtuous cycle of success and fulfillment where being herself is rewarded because that’s what people want and expect. She doesn’t have to worry about other people discovering who she really is. She has already ‘outed’ herself.

Most people have the opposite of authentic networks; default networks. Default networks are the networks we fall into and then try to fit into. If we continually operate in a way where we feel like we need to be inauthentic in order to be successful or appreciated, we’ll feel like a fraud, be less authentic (therefore less trustworthy), and less passionate (therefore less effective). Ultimately, a vicious cycle will occur where we attract and ultimately become financially dependent on a network of people who do not reflect our deepest values.

The Perils Of Personal Transparency

Choosing to start MakeLoveNotPorn has not come without costs though. In Cindy’s words:

Every piece of business infrastructure that any other startup can take for granted, we can’t at MakeLoveNotPorn, because the small print always says, ‘No adult content’. For example, I couldn’t find a single bank here in America that would allow me to open a business bank account for a business that has the word ‘porn’ in its name and that does what we do. Putting payments systems in place is a huge operational challenge. PayPal won’t touch us. won’t either. None of the major credit card processors will. The same thing with trying to find an email partner to send our membership emails out with. We had to build our entire video sharing and video streaming platform from scratch because off-the-shelf video streaming platforms like Brightcove won’t work with adult content.

As Cindy went through all the challenges, a question kept on coming up in my head, “Why not remove ‘porn’ from the name if it is causing so many challenges?”

Before I could ask the question, Cindy answered it, “The more I encountered all of these obstacles that I had never anticipated, the more I realized how every single one of them represented how enormously important it is that we do what we do, which is make real world sex socially acceptable and socially sharable.”

The risk anyone faces of being more visible and unique in the online environment is trolls, individuals who use snark to put others down and who often hide behind the veil of anonymity. After Cindy spoke at TED, TED did not post Cindy’s talk because of the content. Eventually, they posted it on Youtube, but disabled the comment stream. After she asked for the comments to be enabled, over 3,000 comments streamed in. Cindy took the time to respond personally to 90% of those comments. Most of the negative comments were from young men, and when she engaged them, they either apologized publicly or through a private message, although some kept on going no matter what she did.

The overwhelming response to the talk was positive both online and offline.

Cindy doesn’t regret her choice to live a more transparent life; not even for a second.

Even with intellectually understanding the power of Cindy’s approach, it still feels risky to be vulnerable online. When I write more openly, my mind starts running through worst case scenarios that all have the same plot; if I share xyz about myself, people will not accept me. I will lose friends I want to keep and I will lose business that I can’t afford to lose.

It wasn’t until I read Nassim Taleb’s words that I fully understood how ‘un-risky’ Cindy’s way of being is.

Don’t Aim To Be Perfect! Aim To Be Antifragile

Nassim Taleb, co-director of the Research Center For Risk Engineering at NYU and New York Times bestselling author of the book, The Black Swan, is not afraid to share what he really thinks and put his reputation on the line. The first sentence of his website boldly states:

Ethics: “If you see fraud and don’t shout fraud, you are a fraud”.

 In his most recent book, Antifragile: Things That Gain from Disorder, you are definitely not left wondering what he actually thinks.

He takes on prominent economists who make bad predictions that cause taxpayers a lot of money, have no skin of their own in the game, and cherry pick and publicize their predictions that did come true. When talking about seeing Thomas Friedman, New York Times columnist and Nobel-prize winner at the World Economic Forum, he describes himself as feeling physically sick and nauseous. For Nobel-prize winning economist, Joseph Stiglitz, he coined a phrase ‘Stiglitz Syndrome’.

How does someone get away with saying his thoughts so directly and yet be so respected?

Nassim has built an antifragile reputation.

As he explains in the book, things that are fragile break when they’re exposed to stressors. A glass vase is the perfect example. If you drop it, it breaks. With fragile objects, you want to keep them as safe as possible.

Things that are robust do not change when exposed to stressors.

Nassim’s contribution is the introduction of a third category; antifragile. Antifragile things actually want stress up to a point, because they become stronger with it. Our bodies are a perfect example. We grow muscle by exposing it to lots of resistance.

As we enter a world where there is more and more uncertainty and where other people have control over our reputations, becoming antifragile by ‘outing’ yourself may be the best approach to building our reputation.

In his book, Nassim recommends:

Some jobs and professions are fragile to reputational harm, something that in the age of the Internet cannot possibly be controlled – these jobs aren’t worth having. You do not want to “control” your reputation; you won’t be able to do it by controlling information flow. Instead focus on altering your exposure, say, by putting yourself in a position impervious to reputational damage. Or even put yourself in a situation to benefit from the antifragility of information. In that sense, a writer is antifragile [benefitted by a stressor]…


Now let’s say I were a midlevel executive employee of some corporation listed on the London Stock Exchange, the sort who never take chances by dressing down, always wearing a suit and tie (even on the beach). What would happen to me if I attack the fragilista? My firing and arrest record would plague me forever. I would be a total victim of informational antifragility. But someone earning close to minimum wage, say, a construction worker or a taxi driver, does not overly depend on his reputation and is free to have his own opinions. He would be merely robust [not hurt or helped] compared to the artist, who is antifragile. A midlevel bank employee with mortgage would be fragile to the extreme. In fact he would be completely a prisoner of the value system that invites him to be corrupt to the core — because of his dependence on the annual vacation in Barbados. The same with a civil servant in Washington.

The Opportunity Of A Lifetime

The rise of digital reputation platforms is one of the most significant shifts in how people build their reputation in human history.

Beyond industry-specific reputation platforms, there is one major social platform that we all have free access to; social media.

Social publishing platforms have moved beyond traditional social media platforms (i.e., Facebook, Twitter) and have spread across every corner of the web. This includes everywhere  from audio (ie – Soundcloud and Podcasts), video (ie – Youtube, TED, & Vimeo), slides (ie – SlideShare), links (ie – PandaWhale, Reddit), photos (Pinterest, Instagram), documents (DocStoc, Scribd), to long-form articles (Medium, Linkedin Pulse).

Social media also is critical because our social media profile links are often the first few results that people see when they Google us.

Entrepreneurs who have the courage to authentically share their unique story and the generosity to share their best insights have an amazing opportunity to quickly build a world-class, antifragile reputation. In so doing, they have an opportunity to build an authentic network of kindred spirits and stakeholders.