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Obsolete on All Fronts: How Mainstream Media Lost Its Way

Mainstream media today exists in a precarious space, navigating its decline across four essential vectors: economic, structural, cultural, and moral. The problem isn't that this decline is invisible—far from it. But what’s striking is how the mainstream media's introspection remains confined to the easiest and most visible aspect: economics. Everyone loves a business story, and it’s easy to point to failing revenues, shrinking newsrooms, and the pivot to whatever-new-thing-comes-along gone awry. It’s the most accessible part of the narrative. Yet, the bigger picture reveals an institution grappling with obsolescence in ways far more profound.

Economic Obsolescence

Let’s start with economics, as it’s the area mainstream media itself understands best—or claims to. Plunging advertising revenue, subscriber fatigue, and an ever-fractured attention economy have created an existential crisis. This is the vector everyone talks about because numbers don’t lie—or so we believe.

Yet, focusing solely on economics feels like mistaking the symptom for the disease. The revenue decline isn’t just about outdated business models but a failure to adapt to how people consume information in a fragmented world. Still, it’s here where the media punditry—and even some of its sharpest critics—get stuck.

I was listening to the latest episode of Semafor's Mixed Signals media podcast where Ben Smith and Nayeema Raza interview Ken Auletta, the storied media journalist from New Yorker and their analysis is so mainstream, so out of touch on the vectors that matter beyond economic and some structural. This analysis is mainstream media's idea of what a heterodox media view is, which itself says a lot.

Structural Obsolescence

Next comes the structural challenge, which is both more complex and less understood. Alternative media platforms have dismantled the monopoly mainstream outlets once held over information dissemination. Podcasts, newsletters, YouTube creators, and Twitch streamers represent a democratization of media, where the para social nature of the relationship has made brands obsolete, distrusted and shunned.

But the mainstream media often misreads this shift. Many interpret the rise of alternatives as merely technological disruption—a mistaken belief that matching formats or platforms will bring audiences back. The truth is, this is not about tech. It’s about trust. For decades, the media's power lay in its ability to manufacture consent, a process of shaping public opinion to align with elite interests while presenting itself as impartial. People are increasingly aware of the subtle ways narratives are framed, facts are omitted, and dissenting voices are sidelined. People have grown tired of media that speaks from the top down, interpreting events from elite echo chambers while alternative voices resonate precisely because they fill this gap.

Cultural Obsolescence

Cultural irrelevance is where mainstream media truly shows its age. It’s not just out of touch—it’s on a different wavelength entirely. When media organizations represent a narrow spectrum of thought and identity, they miss the nuances of a world becoming increasingly global, diverse, and decentralized.

Take, for instance, their coverage of elections, protests, or social movements. Too often, these stories are filtered through a lens of elite centrism, leaving vast swathes of the population feeling unseen or misrepresented. Meanwhile, independent platforms thrive by acknowledging that culture is lived, messy, and personal.

The rise of "outsider" journalists and platforms is not just a rejection of the mainstream media's content but its tone—a patronizing detachment that fails to resonate with real-life struggles, aspirations, and values. Audiences, particularly younger ones, reject the monolithic and often outdated perspectives of traditional outlets in favor of creators who reflect their lived experiences and values.

Moral Obsolescence

Finally, the moral dimension. Here lies the deepest and most damning failure of mainstream media: its inability to interrogate its own complicity in systems of power. The media, as it exists today, still operates as a product of the establishment, often aligning itself with corporate and governmental interests under the guise of neutrality.

But neutrality is a luxury of those who hold power. The world increasingly divides itself along the axis of establishment versus anti-establishment. People no longer want media that acts as stenographers to power; they seek institutions willing to challenge it. And yet, mainstream outlets cling to outdated paradigms, mistaking access for relevance and equating insider gossip with hard-hitting journalism.

This moral failure also manifests in a broader inability to reckon with its role in shaping the very crises it reports on. Global wars, climate change, social inequality, are too often reduced to headlines and soundbites – ignoring the systemic forces driving them—forces the media itself often amplifies.

The Israel-Gaza war is a glaring example of the moral obsolescence of mainstream media. While the vast majority of the world can now see the facts for themselves—raw footage, firsthand accounts, and undeniable evidence of a massacre—mainstream outlets still attempt to "both sides" the narrative, manufacturing consent for power structures instead of acknowledging the stark realities on the ground. This failure to align with global conscience only deepens the chasm between media institutions and the audiences they claim to serve.

It is Over

Mainstream media’s decline isn’t just inevitable—it’s irreversible and, perhaps, deserved. The very institutions that once shaped public opinion now find themselves exposed, their mechanisms of influence dismantled by alternative platforms that are more transparent, diverse, and aligned with the realities of the modern world. Turning the ship around would require an upheaval so radical that it’s almost unthinkable for these legacy organizations. This isn’t just the end of an era; it’s the rightful conclusion of an outdated model. The future belongs to those who can rebuild trust from the ground up, outside the shadow of power, and that’s a task mainstream media is no longer equipped to handle.

Why Mainstream Fails to Understand B2B Media

There’s a fundamental disconnect between how mainstream media executives or private equity dealmakers perceive B2B media and what actually makes it thrive for the communities they focus on.

Here’s the scene: a dedicated B2B entrepreneur—let’s say someone passionately focused on the global travel industry, like Skift, or fashion insights, like Business of Fashion—is approached by these industry outsiders. Almost invariably, the first question thrown at them is: “This looks great, but when are you going to expand into five more sectors?” I have been asked this hundreds of times over the years of building Skift.

This mindset misses the magic of going deep into a sector. B2B media, when done right, is about obsession, depth, and relationships. Entrepreneurs in this space don’t just cover a sector—they live it, breathe it, and connect deeply with the flows and rhythms of their chosen industry. Their editorial output, events, and business information products are rooted in years of painstakingly building credibility, understanding industry nuances, and cultivating trust. This is not about chasing scale for scale’s sake. It’s about being indispensable to a community, what I has written before as providing daily utility value.

Yes, there are organically grown exceptions that prove the rule. Companies like Industry Dive have successfully tackled multi-sector B2B media, leveraging operational efficiencies and disciplined editorial strategies. But even these rare successes are the exception, not the standard. And often, the minute private equity money flows in, the pressure to scale even further—often into ill-fitting sectors—risks unraveling the delicate balance that made these businesses work in the first place, again, even in the face of exceptions.

The beauty and power of B2B media are in its intentionality. This isn’t a sprint for quick wins or an attempt to cast the widest possible net. It’s a marathon where staying small -- and the aim of becoming the most influential force-- and deeply embedded in one sector often means having the sharpest insights and the most loyal audience. Those who try to force a different model fail, not because B2B media can’t scale, but because it shouldn’t scale the way outsiders think it should. Depth over breadth isn’t just a choice—it’s the foundation.

So, the next time a B2B media entrepreneur is asked, “When are you going to expand into other sectors?” the answer should be simple: “Never. That’s not the point.”

The Rule, the Exception, and the Structural Obsolescence of Mainstream Media

I’ve been thinking about the structural obsolescence of mainstream media and, specifically, the fate of the story format that they depend on for their existence. There’s a rule I see unfolding—and an exception that proves it.

The Rule: The Obsolescence of the Story Format I’m increasingly concerned that the traditional story format—particularly long-form, text-based storytelling—may be on its way out. For years, I dismissed these predictions, believing that the simplicity and longevity of the format would ensure its survival. But two trends are forcing a reevaluation:

The Rise of Multi-Format Media Platforms like podcasts and of course TikTok have pioneered a seamless, multi-format approach, where users move effortlessly between video, audio, and text without even noticing the transitions. This immersive consumption experience strikes a major blow to traditional formats by offering richer, more engaging ways to tell stories.

AI as the Default Information Format AI-generated outputs are fast becoming the standard for delivering information. Tools like ChatGPT provide answers in highly efficient, information-dense formats, which prioritize user-friendliness and retention. While these outputs can feel monotonous or homogeneous, advancements in technology—and the human element that will persist—are likely to solve this problem over time. As @troyyoung and @bmorrissey have pointed out in their always excellent People vs. Algorithm podcast for a while now, this shift toward AI-driven formats is reshaping how information is consumed and valued. The story format, in its traditional sense, is being overtaken by new methods of engagement that prioritize efficiency and density.

The Exception: DropSite News And yet, there’s an important exception example to this rule: @DropSiteNews. This site has seemingly emerged from nowhere (though, of course, it hasn’t). It’s a direct descendant of @theintercept groundbreaking work, with alumni who have channeled their energy and vision into something extraordinary. DropSite News proves that sheer gumption and focus—when tied to the right cultural and moral structures of society—can push investigative journalism forward, even as mainstream media struggles. It reminds us that unless you have an incredibly compelling reason to tell a story in long form, it’s not necessary. Short-form or information-dense formats will continue to dominate.

The Irony of the Shift The irony here is that I’m acknowledging the death of the story format while also highlighting its rare and powerful exceptions. Unless there’s a truly compelling case for long-form storytelling, the short form—or at least structured, dense formats—will rule.

Efforts like @axios and @semafor have tried to reimagine this balance. Axios, in particular, deserves credit for breaking through with its “Smart Brevity” approach. Still, much of the innovation in this space feels performative. The real future lies in how media embraces these shifts: combining multi-format consumption with AI-driven efficiency while preserving the human elements that make storytelling compelling.

As Troy and Brian have been discussing on their podcast, this tension is where the future of media resides. The traditional story format faces significant challenges, but for those willing to innovate—or for those rare cases with a truly exceptional story to tell—the opportunity remains to make an impact.

The Balancing Act of Scaling Your Media Business: Simplify or Complicate

At all times, the struggle you have as a bootstrapped media company is between simplifying your business to scale versus complicating your business to scale.

It's tempting to look at software businesses and wish that scaling a media company could be just as binary. In the software world, you grow by building a single product, refining it, and selling that relatively static product millions of times over, just like Slack.

In media, it's much more challenging because you have to bring along all the revenue streams—subscriptions, advertising, events, commerce, or variations of these. These streams help you diversify your revenue in a fragile media revenue ecosystem.

To build a well-rounded and resilient media business, you must diversify, diversify, diversify, rinse, and repeat. This is particularly true for B2B media companies where any single business line may not be large enough.

For instance, it's always best to have subscriptions as a good part of your revenue stream during downturns. Recurring revenue stabilizes the business. However, during boom times, advertising boosts the top line, even if it's costly to service. Subscriptions and advertising sales have entirely different structures, and at times, they conflict within a single company. Advertising relies on traffic scale, while subscriptions restrict output to paying customers, limiting traffic.

Events are often the first revenue lines to go in a downturn. However, in times of boom, they provide dual revenue streams from sponsorships and user ticket sales. They also bring a significant upfront cash flow boost but are challenging to scale across sectors and geographies, adding complexity to the business.

(P.S.: A decade in, we at Skift are there, our business is split one-third each between subscriptions, events and advertising. That was my original pitch when I first came up with Skift, to have a three-legged stool of revenues.)

One other added complexity in any media business, particularly those with news, is that we recreate a brand new "product" every day, to be judged and live and die by its quality. Every damn day.

Yet, underneath all the complexity lies a simple business premise: pick a subject, report the hell out of it, and either sell the audience or sell to the audience. That's the media business. Everyone looks from the outside and thinks they know what will be best for your business, do this one thing, and just scale that.

Many digital media startups in the past decade raised hundreds of millions of dollars on this premise and are now in trouble. You know their names well; I don’t have to repeat them here. These companies raised money based on the fallacy of infinite scale and focused on one-hit-wonder business lines (e.g., advertising). This isn't software, and it certainly doesn't have the ARR or margins of software subscription businesses, but somehow they — including investors — all forgot that.

However, even amongst all this, the goal at all times is to strive for simplicity while embracing complexity. The allure of simplicity is always there, particularly for a media founder, as a way to grow bigger, possibly faster. Simplicity is easier to market to your intended audience, and it's simpler for the audience to understand your offering and, consequently, spend money with you. And if you can optimize for simplicity of offering, you can also optimize for higher profit margins with a dedicated focus on a single product.

So there you have it, the constant struggle of scaling a bootstrapped media company. It's a balancing act between simplifying our businesses and embracing the complexities necessary for growth and stability. It then becomes a long-term game of intentional growth.

While we might occasionally daydream about the simpler life of a software business, we have to remember that the media world offers its own unique challenges and opportunities.

No one said it would be easy.

#media industry

Life learnings and such, 46 years in

In the fall last year, I hit a mental wall. Starting from my father passing away in Dec 2019 to the pandemic challenges in spring and summer of 2020 rescuing the business I had spent almost a decade building, to the lockdown challenges with our family trapped at home, it all caught up with me. Having suffered through mental health challenges through my life — it runs through my paternal side of the family — in my 40s I am getting better at reading the signs of mental overload, though I still haven’t figured better ways to back off before these signs manifest.

I took two weeks off in Oct-Nov to detoxify myself from the sensory and emotional overload — and took it easier the rest of the year after — and those two weeks were some of the most present-in-the-moment days I have had in a long, long time. And through those pre-dawn clarifying type of days, I wrote these life learnings for me, most of them reflect in both my personal and professional lives. I have always written my way out of most of life’s curveballs, and this one came through typing on my iPhone notes app on and off for a few days.

You may find you own reflection in some of these.

Life is unfair, get used to it. That also is the point of it that drives you, in ways health and unhealthy.

Delayed reaction is the biggest power you have that you use the least.

Listening -- and not reacting -- is the lost art of our generation.

We’re not as strong as we think we are, and we’re not as weak as we think we are.

The ability to hold two contradictory thoughts at once is the biggest skill to aim for, and that takes time.

No one learns wisdom in the moment while they’re going through it, unfortunately it’s always on the other end of things. P.S.: we always start drawing lessons about life too early. I know, I know, the irony of this...

When everyone else takes a right turn, turn left. Turns out, I have taken this literally: this has been my default traveling style as well.

Curiosity is everything, so question everything but know that not everything has answers.

Believe the experts, they have spend time that you haven’t on the subject.

Read history books — particularly not written by winners of history — the key to curiosity and wisdom in life, in that order.

Kids are worth every pain they give you, for the joy they give you

Writing it out, long form, is always usually the best answer.

Always check your calendar the evening before.

Real time will kill you, the key is figuring out asynchronous life.

Demography is destiny, but reaching destiny takes a long time and it’s really messy while going through it.

Every setback *really* is a learning opportunity, and unfortunately we always learn that lesson after the fact

Nature is all around you waiting to welcome you back if you can stop for long enough.

The quiet competence usually doesn’t shout from the rooftops, it usually tiptoes in for those who stop to listen.

Your most lucid moments come usually when you aren’t ready. Have a pen/notebook as handy as you can.

Everyone always has things going on that you have no idea about and has nothing to do with you, practice kindness and generosity, the keyword being “practice”.

Everyone always uses too many paper towels.

You become what you watch, listen and read.

The answer, as always, lies in the middle even though the question — and change — almost always start from the edges.

Celebrate the small wins along the way, otherwise you will keep waiting.

Cheerleading others becomes the biggest joy in life after the early execution phase of your life, even if you don’t get anything in return for it.

Everyone’s path to the learnings usually differs, though they end up with mostly the same learnings of life.

We are all guilty of what we accuse others of.

There are enough decent people working selflessly in our communities, find them and amplify them as you can.

Faith is important, any kind of faith, and those who say otherwise are privileged enough to say so, be wary of them.

Read as widely as you can to connect all the dots. Connecting the dots is the biggest skill of all.

Always play hide-and-seek with your kid if they are asking.

Constraints do make you more creative, even if you don’t see it now.

It’s not the lens that make a great photograph, it’s your eye looking through that lens.

The commingling of personal and professional lives, how we live our lives these days, manifests itself in so many harmful ways through us and our circles we care for.

Self care, family & friends, and then work, in that order.

Therapy doesn’t give you answers, only the framework to get the answers yourself.

Asking the hard questions is one of the biggest fears of life to overcome.

We all catastrophize too much.

In the long term, consistently making small dents in the universe is a lot more satisfying than one big dent every so often.

As in life, so it is in business: everything runs in cycles, even if the other end of the new cycle is different from what it was before.

To sleep on it is *always* the best strategy.

If you don’t follow up, you never get the call back.

All-in-one solutions are not best at any one of the solutions they offer.

We are all dispensable, however indispensable we think of ourselves in the moment.

Becoming older *is* better.

In the end, everything works out, and if it hasn’t yet, it isn’t the end.

On Breaking Away: 18 Years Of Lessons On Journalist-As-An-Entrepreneur Life

Back in 2003, I wrote this rather bombastic “screed” about life as an individual journalist-entrepreneur, then a year into my journey on solo media entrepreneur life back then through paidContent.org (now defunct).

I was in my 20s then, barely two years into my career out of school and was a know-it-all, living in an East London tenement with a leaky roof, creating my own path on the backs of early blog publishing tools like Blogger, pMachine (anyone remembers that?!) and MovableType. This was 2003 and I had been blogging for four years then, had a Btech in Computer Engineering, MA in New Media journalism and loved the merging of reporting skills, DIY tech publishing tools and immediacy & freedom of blog journalism world. I was barely making subsistence money and still happy to just be doing my own thing.

Fast forward to 2020s, a year like no other for media, and the Substack generation is the new blogging-in-pajamas generation. Lots of hard knock lessons we learned back then still apply and figured I would jot them down, might be helpful to the new generation of journalists-as-entrepreneurs.

If you want control of your own destiny, then you’re in for the long-haul. This will take much much longer than you think or the initial reception will indicate.

If you can, give yourself two years as a good ballpark before you can become fully self-sustaining. After that time if you aren’t, you know the answer from there...

Own the stack and everything else along with it. While tools like Substack and others are enticing to get you started, there’s nothing like having your own site, where are you can do whatever you want to without the constraints of whatever choose any of these third-party providers will create. These days creating a Wordpress site and putting an email newsletter other, charge for it and dozens of other things in it are very easy these days and don’t require any technical knowledge, and even if they do, you can find cheap freelance talent to help you put it together and maintain it.

OWN your email newsletter list, don’t outsource that part to anyone or any entity.

While the newsletter format is great it get started, don’t ignore a standalone site which will allow you to better showcase previous work, archives, and pull in people better through search/SEO than just a newsletter format can. Also be ready to be multi format: podcasts, online webinars etc, whatever it takes to build the paying audience.

Subscriptions aren’t the only way, don’t let the herd guide you on this. Smart, long lasting businesses — even solo journalist entities — have multi pronged revenue streams built into them, including advertising, yes that dreaded A-word these days.

There’s nothing called the first mover advantage, that’s a myth in media. It works in platforms but popularity doesn’t necessarily mean revenues.

However crowded a sector you are in is, you can create your own whitespace by your own unique worldview. So better know what your unique worldview is before you get started.

Starting out as an ad-supported site/newsletter doesn’t mean you can’t convert to paid later, it’s just harder but it can be done. In fact a hybrid free+paid makes most sense for maximum impact.

Pace yourself, or else you will burn out quickly. Don’t “out-blog and out-news anyone to death” as I foolishly said 17 years ago when I started on my solo journey.

Frequency of output does matter, and consistency in frequency matters. You can be daily or weekly or mix of both, anything longer people won’t know how to value your work when deciding to pay for it, or not.

Bring original reporting and original thought into the world, that is what people will value in the short and long term. One step removed from original editorial is one step too many removed from success.

Build franchises people return to every year or every quarter. Yep, lists matters, and there are meaningful ways to do it.

Ignore and break the silos in whatever industry/sector you are writing about, the forward looking people in your sector will thank you for it.

Don’t write for praise of fellow journalists & media people, they have no bearing on your success, write for the audience that will care for what you write and build.

VERY IMPORTANT: Pay up for good financial advice, company structure and tax advice, your future self will thank you for it.

Stay solo or hire more people? You don’t need to know the answer right away, don’t worry about it, you’ll figure it out along the way. Just make sure your financial/company structure is set up right way for either, from the start.

Over a period of time, you’ll figure out what you are good at, and more importantly, what you aren't good at. Ask for help from experts and you’ll be surprised how many are willing to help you pro bono.

Will anyone miss you if you stop your newsletter/publication tomorrow? That is the ultimate mark of impact you can have, it will take time to get there.

“Fuck it, I’m going for it” will take you a long way in building your own destiny. Fuck the naysayers.

An Ode To My Father I Am Finally Ready To Mourn

On Oct 18,1999, my dad wrote me a letter. Yes, an actual physical paper letter, six pages long in his bold, clear writing with his ink pen.

I was 25 years old, about three months into my life in America, an Indian Muslim student in Indiana trying to fit in. I was trying to conform to the mores of student life in a completely alien culture and was failing badly at it, so much so that I was about to give up and go back to India.

In my moment of weakness, I called my mom — those days phone calls from U.S. to any foreign country were very expensive, hence surprising and even shocking — and confessed about my loneliness and my desire to come back home.

This letter he wrote was in response to my distress phone call was an exhortation to not give up on the promise of America that he knew having lived here for a few years earlier in his life, and most of all, not give up on my own ability to figure my way out of this. He was the conventional strong and silent-type of dad and he and I never really spoke at length, he was the one we older siblings were always afraid of; he softened later in life (and my younger siblings had a different relationship with him as a result) but by that time I had left home. This letter was probably amongst the longest he ever “talked” to me.

Twenty years later, I now realize re-reading this six months after his death, that this was the letter that saved me and defined my life from then on. It was a distillation of everything I learned from him, directly and by osmosis: Get up, snap out of the funk, set priorities in life and forget trying to be like everyone else around you. Be curious about everything, be fiercely independent in outlook, simplify things as you go along, and above all, create your own space in America and the world, and arrange the space however you want.

I rediscovered this letter three years ago on a visit back to my parents home, and while he was already ailing by then, I relearned my respect for him and knew this would be the succor for me after he was gone.

Six months since he died, I have not been able to start mourning his passing yet and have been trying to figure out how to. I wasn’t allowed to cry or ruminate when I was there for his funeral in India, to be strong for my mom and siblings. When I came back to U.S. around mid-Jan, after readjusting back to life here, was shortly after thrown into the biggest professional crisis of my life and indeed our lifetimes: the global pandemic and the complete decimation of the source of our sustenance as a business, the travel industry and life since then has been, well, you all know.

Now, six months later, I am finally ready to start mourning, to appreciate the life he lived, the quiet fortitude of his existence, and an urgency to make the most of my life ahead in my adopted country despite the gloom of its current promise, for my family and most importantly for my 5 year old son’s sake. Some day he will have to be ready to read the letter I will write him.

I share this letter to start the process.

P.S.: For context, Nadeem is my family name, a very Indian thing, and my parents were then was living in Saudi Arabia. Earlier, we lived in America from 1975–79 when I was kid, hence his knowledge about this country.

The Challenges In Building An Inclusive Organization Even As A Minority Founder

I’ve created two companies that have employed a couple hundred people during the past 15 years. Much through that time, I’ve shared thoughts and lessons on that journey here and in my other essays. Today, I’d like to share a few more because I believe all founders and CEOs in America have an important opportunity and responsibility in this moment. The reckoning is real, even for minority founders and their well-intentioned teams.

What is that collision — and tension — between being a minority and being a founder? Exactly two decades since I came here as an immigrant to America, I have been thinking through these existential questions. Today, we finally are having a larger conversation around diversity and inclusion in our society and workplaces, including ours.

Everyone on the leadership team at my current company is thinking deeply right now about our responsibilities around diversity and inclusion. We’re prompted by the larger conversation America is having, and feedback we got from our team on a lot of work still left to be done to improve the way our company shepherds both diversity and inclusion. Like many companies, we should constantly be aware of unconscious bias and structural racism at our organization and in our industry.

We’re throwing ourselves into this. Even as we are in survival mode as a business during this pandemic, we’re moving quickly to define areas for improvement, assembling cross-company teams to identify options and recommend immediate and long-term courses of action, and we’ve set out a schedule to get our initial improvements in place as rapidly as possible. We’re treating this work as seriously as we treat our service to readers and customers. And it’s being done alongside other business improvements prompted by sweeping changes to the sectors we exist in.

Here are the challenges we’ve faced, mistakes made, and lessons learned so far:

We overreached on our promises to the team. In hindsight we were naive about what it took to shape a culture. I believed the intensity and quality of our work were all that mattered, and I believed that our culture would organically spring from that. I realize now there’s no way a small and mostly bootstrapped company, with no real systems in place in early days, can keep everyone happy or intentionally create its intended culture without help.

I started this company after a two-year journey that took me to 15 countries. I saw first hand the fault lines and inequities of the world; experienced world events as a minority; and then threw myself into self-education and expression around it. When I returned to the U.S., I first found my voice on social media, my personal blog, and by writing and speaking about diversity and inclusion through media outlets. I pursued the topic at times to the point of exhaustion — after 9/11, the Othering of Muslims happened in America in large and small ways, and a chance run-in with Glenn Beck in late 2011 went viral when I confronted him about being a racist bigot tearing away at the fabric of our country.

Finally I decided to create a company that would forever improve travel, one of the world’s largest business sectors. It would be a global media business, and the team at its heart would look like the changing and diverse world of the travelers criss-crossing the globe — even though the travel industry itself was not at all reflective of that… and still isn’t. We would be a refuge among the decimated media businesses that surrounded us. Our hiring motto in every job posting said: “Our goal for our team and culture is to reflect the diversity of the globe of travelers.”

Investors had other ideas — we could not raise venture money beyond seed stage, despite hundreds of pitches. Among other reasons, it was clear there was a subtext of overt and covert inequities at work — especially ageism against older founders (I had turned 40) and white male founder privilege(one investor told me “jokingly” he could invest only if I was the “right religion”).

Nevertheless, we promised potential team members:

Joining Skift will be a transformational move for your career. You will do the best work you have ever done while you are at Skift. You will be the happiest you have ever been at work while at Skift. You will be set for life, your success beyond Skift means everything to us.

I believed our good intentions on this would carry the day. After all, I was a minority putting everything into this as transparently as possible. I was out there, very online, with beliefs about every injustice and progressive movement in the world — from the Arab Spring onwards — and that would create a progressive company. Because everyone else would see it that way too, right? Wrong.

In hindsight this was very naive and by overreaching on the promises, we were setting ourselves up for failure.

We didn’t put enough resources against our diversity goals.Diversity requires putting extra effort into the normal hiring process — and with no recruiting help, we weren’t able to access enough candidates to achieve true diversity. We didn’t have enough time to do it ourselves while also building other aspects of the company, and our personal professional networks weren’t diverse enough.

We’ve succeeded in stretches. At one point, and for almost two years, no one voluntarily left the company. We became obsessed with keeping that going, learning later that holding on to an impossible ideal was a growing-up folly, too. We succeeded in becoming a female majority company three years ago. But we have a lot more work to do — we’ve hired Asian, Indian, Black, Hispanic and LGBQT+ people as well as people across the age spectrum, but it hasn’t been enough — and I’ve shared those challenges along the way, internally and externally.

We didn’t transition our operations from a start-up to a more mature, early-stage company soon enough. Although we were well-intentioned, we were not well-equipped to achieve all of our ambitious goals. Two examples stand out:

We should have brought on professional recruiting and HR sooner.Other startup founders and investors I talked to along the way said to hire our first full-time recruiting and HR professionals once we crossed 50 employees. That advice may be relevant for well-funded startups that hired 50 people in their first year or two, but for a boutique, thinly-capitalized, and seemingly always overstretched company, those 50 people took seven years.

If you are a founder and have never worked with a business coach in your journey, get one as soon as your company grows beyond the start-up stage. What brings you success at the beginning may not get you to the next phase of your business or culture. This transition from early-stage full-hands-on, push-and-probe-to-get-the-best-results-from-people founder to a more mature, systems-in-place style happens with every founder, and every founder hopes they will avoid the pain that comes with it. Few do.

I started working with a coach two years ago and I still have a lot of learning to do. The founder in me intersected with my own life as an immigrant in America, the very-true cliche about having to hustle twice as hard to get the same results, resulting in a demanding work environment. I originally saw a very direct working style as a proxy to transparency. The coaching helped me realize that at a certain point, my personal intensity and company power dynamics overpowered any good intentions.

Diversity isn’t enough. Leading a successful company means creating real and consistent inclusion. As a Brown Muslim in America for the past 20 years, I’d experienced much of my personal and professional life through a lens of exclusion, but the real lesson we had to learn was inclusion. We became so focused on building a diverse team that we didn’t focus on the even harder part — creating a supportive culture once this diverse group was inside the company. From retaining employees with different needs to being cognizant of and celebrating differences; from creating safe spaces for people with different frames of reference to mentoring and finding ways to support professional and personal growth paths in the ways larger companies with greater resources can.

We have been well intentioned but not well equipped to carry out the intentions, intentionally. We finally brought on a very experienced HR leader last year. We could not be doing this important work without her.

There will be more insights and learnings — and probably mistakes — as this work continues. When we learn more things that could be helpful to other founders and CEOs, I’ll continue to share them here.

This is a critical and existential time for our company in so many ways. The travel industry was hit hard by the pandemic. We lost 80 percent of our revenues in March and April, and May and June have only slightly better with somewhat more clarity on business outlook ahead. We had to scramble to cut every non-employee cost we could.

We are surviving because of the sacrifices of our amazing team — including furloughs and pay cuts starting at 10 percent (I took a 100% pay cut and my leadership team has taken pay cuts of up to 50%). We have given up our New York and London offices and are going fully remote as a company — a decision that saved many jobs. Unfortunately, we still had to reduce our team size by one-third last month.

For now, as we create our next phase, we will continue to improve our business, and we have committed ourselves to creating a better company — to listen, to learn, and to act — and we will continue to reshape our culture for meaningful and lasting change.

Digital Media: What *Really* Went Wrong in 2018

Seven years into running Skift as a fiercely independent business media company, I have become a fan of this financial term called “optionality” which by the way is also Mohamed El-Erian’s favorite word. What it means in Buzzfeed’s context is it lost a number of options when it took so much venture capital, one of which would have been slower growth, another of which would have been not artificially looking for an exit within a fixed time frame or too early. Or, that the $1 billion deal they were getting from Disney would have been enough money for everyone, but investors likely balked because they thought they could get more returns than that.

All of them — Buzzfeed, Vox, Vice — raised this money based on the fallacy of infinite scale and even more problematic, that one-hit wonder type of business line (advertising or specific type of advertising) would scale infinitely. This isn’t software, certainly doesn’t have the ARR or margins of software subscription business, and somehow they — including investors — all forgot that. Vice is in slightly different bucket because it predates this era of Web, but then mismanagement really did it in.

Another big hurdle: the potential buyers have whittled down as well: AOL and Yahoo used to buy such companies are now done with and in lots of troubles of their own. Comcast, Disney, AT&T and other large conglomerates are focused on much larger TV/video deals, dealing with a much bigger enemy such as Netflix. Time Inc and Conde Nast are, well, you know their story, completely out of the picture and Hearst is buying big companies in B2B media. Axel Springer is not an option, it has its hands full with Business Insider and if that goes south for them they will sit out the market. Facebook, Google and Apple are not coming to anyone’s rescue, particularly not in media. Unless Vision Fund buys everything, which you never know with Son, the buyers are gone.

They got seduced by the idea that this is easy, digital media is easy to build in a platform era. It should be really hard to raise millions and millions in funding. It should be hard and maybe impossible to have a valuation in hundreds of millions. It better be freakin’ hard to have millions in revenues and reach sustainability as a media company. That is what every other previous era of media taught us.

The democratization of publishing has had lots of good effects for the growth of media around the world, the biggest being the proliferation of previously under-represented groups to have a voice. But amongst the worst effects of it has been the perception that it is easy to be in media, raise money in media, build a company in media — driven in large part by availability of venture money.

As soon as you take money in any big way, you are not in control. This is a digital media fallacy: That big venture money backed digital media startups are independent. They’re not, boxed in to do whatever it takes to get to desired outcome promised. If anything has a timed outcome in a 3–7 year horizon, which most venture backed companies have, that dictates *everything*. Truly independent companies are meant to last forever. That is the box these digital media companies are in: these are artificial constructs meant to exit in a decent timeframe, with no exits in sight.

For us at Skift, we raised peanuts compared to everyone else, total of $3 million in seven years we have been in existence and we haven’t officially raised since 2014. We have always been very intentional in our growth and know that we can be innovative within the constraints we have. Being a small company has meant always being short on resources. Less is better, less is deep, less is slow and deliberate, less is human, and humane. In many ways that has defined the ethos at Skift, and has kept the primacy of action over intent. Constraints — having less — has also means less panic about every new thing every other media company is chasing. We know what we’re good at and what we aren’t. Now having crossed our early phase and now in our Young Adult phase, we have lots of options ahead and we are in control of which option we take.

Lots of people are knocking on our doors, and I have relished saying no again and again.

It *Should* Be Freakin’ Hard To Be In Media

I have usually held unpopular views well enough, so I will go for it: it *should* be hard. Starting something in media, building in, being in it, building a career in it, it should be hard.

It should be hard to have and hold down a job in media, to have and hold down a job in journalism. It should be hard to report, it should be harder to write great stories out of reporting.

It should be really hard to raise millions and millions in funding. It should be hard and maybe impossible to have a valuation in hundreds of millions. It better be freakin’ hard to have millions in revenues and reach sustainability as a media company.

It should be hard to do great video, harder to have anyone watch it. It should be hard to get traffic from platforms, hard to get people to “share” your creation through platforms. It should be harder to start a media publication than putting up posts on Medium.

It should be harder than just coming up with some bullshit idea to start a millennial media outlet, whatever that means. It shouldn’t be easy to get two full floors in World Trade Center building as your office, when you’re running on borrowed money and time. It should be hard to call yourself the Condé Nast of the next generation, harder to even build one. It should be harder than starting with clickbait and then pivoting to quality, and then raise up hands when that is hard to do. It should be hard to replicate your success in one vertical to others.

It should be hard for man-child douchebags to start media companies, harder still to make money off it. It should be hard for white privilege to “reinvent media”, whatever the fuck that means. It should be hard to fail upwards for white males in media.

The democratization of publishing has had lots of good effects for the growth of media around the world, the biggest being the proliferation of previously under-represented groups to have a voice. But amongst the worst effects of it has been the perception that it is easy to be in media, have a career in media, raise money in media, build a company in media.

Few are in it for tons of money, that still remains true, most of us are in it for glory.

Getting glory should be really hard.

Six Essential Reads to Understand My Building Philosophy

Since 2015, I have increasingly been writing about the process of how I look at building companies -- specifically boutique media companies -- the lessons I have learned while doing them, and the philosophies on creating, nurturing and sustaining that I have developed as a result.

Thought I would gather the six longer writings/presentations I have created and posted, in one place; it may be helpful to many of you looking to ways to think through your own businesses. So here you go:

The Process of Growing Up: Go Slow To Go Fast

How We Got off the Addiction to Venture Capital and Created Our Own Way to Profits

Small And Mighty: Why Small is Having A Big Moment

That Company Culture Question: What Is it?

Patience: The Radical New Business Model

Lessons From A Decade In Media Entrepreneurship

#entrepreneur #company #business

Patience: The Radical New Business Model

Skift is turning six. Of all the achievements anyone can ask of a company from its infancy, staying power — mere survival — is the toughest of them. Let no one tell you otherwise. Make it a media startup in an age of existential crisis in media all around, and you’ve created the biggest odds against yourself right from the start.

Six years into the serpentine journey of building Skift — 2,191 days after launch — we are still here and intend to be here for a long, long time.

Longevity is not top-of-mind for many founders just starting out. Certainly, having a legacy is even further off the map. But there are certain catalysts that move you toward that realization as a founder, and I had mine about halfway into the six-year journey.

My son was born in early 2015, right about the time when the company I founded three years prior was growing out of its early-stage, survival-at-all-costs phase. Clichéd as it may sound — because everyone who has ever been a parent tells you so — the new life in my life ended up changing everything about my outlook on, well, life and business.

As I started thinking about this new life we had to take care of, I started thinking about the values I would love our son to grow up with, and that would have to start with us parents teaching him what we held dear, the values we got from our parents as we grew up.

The biggest one I kept thinking about and finally honed in on was patience. In the on-demand world of instant gratification we all live in now, patience — in intent, in living, in outlook on life — is becoming a rarer and rarer life skill, incredibly. And make no mistake, it certainly is a life skill.

Having grown up in socialist India in the 1980s, the precursor to learning patience, frustration, was not a bug in the system. It was the feature of how everyday life worked. Anything and everything was a wait. It was a wait with lots and lots of people in line with you, and that was if there was enough civic value in us to form a line in the first place. India breaks you down if you come in with Western notions of efficiency, a clean logical version of input versus output of effort. If you grew up there, like I did, it builds you up with an ingrained sense of equanimity about everything.

The daily knocks on your inner resolve to not give up, on your self-esteem, on making do with what you have, taught us patience. It taught us the long view, that in the end everything will work out if you just keep at it. All is well in the end. If not, it’s not the end.

That is the life skill I want to teach my now-pre-schooler-and-already-impatient son. “Le pause,” the great way French parents teach their kids patience. Pausing before rushing in. As simple as that.

It is the value I have brought to the company I started and I am building now along with the Skift team.

Not raising lots of money, and deciding not to raise any money beyond seed and building our own way, has given us patience. Patience gives us the ability to block out the extraneous noise and buzz of the startup ecosystem, and focus on building the products and brands that matter.

Think it through, slow down a bit. Go slow to go fast, a philosophy we adopted in 2015. I wrote this in that memo: “This is the new Skift operating principle — both in our work and culture — that we want to embody going forward.

Doing less with more is the new doing more with less.

Going slow to go fast is the new scaling up.

Less is better, less is deep, less is slow and deliberate, less is human, and humane.”

When every prevailing startup wisdom says move fast and break things, there is value to doing the complete opposite. When everyone wants speed, pivots, scale, fail quick, there is value in focusing on your vision, burrowing deep, and taking time in building. Quality is the end result of patience. Quality is the table-stakes start of longevity.

That means reorienting everything patiently to this long-term thinking.

For us as a media company, it starts with our editorial and research: Think beyond headlines, to the trendlines shaping the business and future of travel, something we have embraced for all of our existence: finding, following, and deciphering the trends in travel. Think in multi-year narrative arcs — that is a mantra I tell our editorial leadership at every occasion I can. Every story we are chasing has a longer-term view, a history longer than we can imagine, a wider and deeper perspective we are currently planning to write. Everything we write can be enriched by speaking to sources beyond the usual suspects. The diversity of views makes the writing we do more relevant today and relevant in the long term. Writing in a human language — outside of the current buzzwords — about the business of travel means we are readable today and likely readable a long time from now, when the industry has completely changed.

That also means redefining what innovation means to us. One of the fallacies of media innovation today is 1) new = innovation 2) new formats = innovation. It is the basis of much of the ruin in media, chasing every new thing that comes along. Innovation for us, what I have bet my media companies on, is not chasing formats, but new ways of looking at existing sectors. Chasing new formats and hoping for innovation is like changing your reading glasses again and again and hoping you will read different things with each new pair you put on. Bringing new perspectives requires a lot more patience and innovation than cosmetic format changes. New ways of looking at the world — that’s the real innovation we are betting on long-term.

That also means redefining what scale means to us. The internet changed what scale meant to everyone, and it became a never-ending quest of chasing bigger and bigger audiences. It became “scale for scale’s sake” and investor-driven frenzy to prove out a model that ultimately ate itself. We gave up chasing scale around 2014, after this realization and have redefined it since: The media we are building is a big part of those who care about travel. That for us is scale, to be a big part of the professional lives of the people in the travel industry. That is how we gauge the effect we are having.

That also means redefining what hiring means to us. We want to hire and groom travel careerists, people who want and have deep expertise in travel — not dilettantes — and want to make a career in one of the most exciting and largest sectors on the planet. We give an audacious four-point promise to our employees, a long term commitment from us to them:

Joining Skift will be a transformational move for your career.

You will do the best work you have ever done while you are at Skift.

You will be the happiest you have ever been at work, while at Skift.

You will be set for life; your success beyond Skift means everything to us.

That’s also what performance — of us as a company, of our team — means to us. That means show up and produce, every day, day in, day out, over and over again. Consistency, in the right amount every day, matters a lot more than being consumed by work and work alone. The quality of our work is the end result of this consistency mixed with patience. That’s the not-so-secret of our long-term fecundity.

That also means redefining what culture means to us. It is not this mythical, magical thing that comes at the end of work, an add-on to make the drudgery bearable. For us, culture stems from the meaningful work we do, and each of us seeing the tangible in-situ effects of that work — helping change the direction of the future of travel and dining, even — in a reasonably short time frame for the people for whom we create everything. It gives us a purpose to create a long-term culture, around the larger promise of travel and our promise to the travel sector: We are eternally curious about the business and creative possibilities of travel, and what it means to the world at large. “If you are tired of Skift, you are tired of the promise of travel,” is a line I use often. That is what inhabits our culture, today and well into the future.

That certainly means redefining how we look at creating value in the company we are building. What does it take to build a media company that matters to people in their daily personal or professional lives, that can survive any kind of micro or macro correction, that can thrive in the long haul?

We have come up with a “metric” to gauge the longevity of media brands. It goes something like this: Imagine, because of some catastrophe, the media company you know suddenly shuts down tomorrow. Will anyone miss it, and will the disappearance of said company harm the ecosystem at large in various ways? The first part of this question is a level-one test, the second part a level-two test, both of which take time to build up to.

What would happen on day two and beyond, if you suddenly go away tomorrow?

These are two ways of saying the same thing: How much of a personal or professional utility value do your users ascribe to your brand? And how indispensable are you to the ecosystem you exist in?

All of this hides an ugly unspoken truth about media in general: that it is disposable, in so many ways. The key is to move toward making yourself indispensable, by adding enough value.

That also means redefining what leadership means to me. Instead of “leading from the front” as I have done for the first five years, a necessary role to build a company in its infancy, I am now transitioning to “empowering from behind” as is the management of our company. After being the face of Skift, being a face of Skift is role that I now cherish. The long-term goal of any founder is to make themselves useless. I am on that journey now.

Last week we launched a book, “For the Long Haul.” This book is an aspirational manifestation of our philosophy on longevity, using travel companies as a mirror to look at the qualities of long-lasting companies and brands. From the efficiency-focus of JR East in Japan, to the courageous will to disrupt from Southwest Airlines, to never putting a price on serving your customers from Oberoi hotels, to Expedia’s realization it could make real people’s lives easier, the chapters here offer valuable lessons. Autogrill’s ability to create a sense of place with all its offerings, and the South by Southwest festival’s willingness to embrace outsiders are testaments to the long view. We, at Skift, salute these strategies as we look ahead to many more of our own anniversary celebrations.

Six Lessons in Year Six Of A Sustainably-Grown Media Company

Skift, my second company, is turning six on July 30th. Jotting down some topline lessons we as a team have learned in the last year of this sustainably-grown media company.

After year 5, the honeymoon period is over, you are no longer given the benefit of doubt by your customers. Which actually works for you in best ways to help you grow up. For instance, you become serious about churn in business, and build client retention as a discipline.

Everyone else who has built a company tells you about the growing pains they went through past the early stage, you think it won’t happen to you and then they do and you realize it is ok, this is supposed to happen too.

Somehow this seems to be the magic year where people start knocking on your door to see if you’re interested in selling (WE ARE NOT.) Also seems to be the magic year where acquisitions to grow inorganically start to make sense (Stand by.)

Keeping the curiosity for the years to come needs to become a process, otherwise you just keep on producing story after story (the unit of production at a media company) for the sake of it. I made that mistake in my first media company paidContent.

Doing things together a company— the full team — becomes even more important, an organized event, something you took for granted when you were 5-10 people hustling away in a small room. You create and tell stories about your company, and don’t feel silly about it because it is what the new people joining the team *want* to hear.

My role as the founder/CEO seems to have reversed completely: from “Leading from the front” to “Empower from behind.” I wrote about that here. Also the year where other long time early employees are more likely to change roles as one tour of duty is over.

That Company Culture Question: What Is it?

Note: Below is a version of a memo I sent to the Skift team, after our annual retreat in Puerto Rico last month. It has become bit of a tradition: I write a team memo after every retreat, and this retreat was the best we had in our company history, for so many reasons. I wrote up some lessons as I reflected on the retreat, what came out of it, and the six years of building Skift along with all of the Skift team.

Six years into Skift, one of the most common questions I get as the Founder and CEO is a cliched and simple one: What is your culture like? And for those who know us — have known us for a while — the question turns into: How do you keep your culture?

The first one usually comes from candidates we interview for hiring. The second one comes with a subtext of wonder: Everything about Skift culture looks amazing from outside, how do you do it?

I always start by defining what our culture is not: it is not this mythical/magical thing that comes at the end of work, an add on to make the drudgery bearable.

For us culture stems from meaningful work we do, and *each of us* seeing the tangible in-situ effects of that work — help change the direction of the future of travel and dining, even — in a reasonably short time frame on the people we create everything for.

Our culture ties in to the larger promise of travel. “If you are tired of Skift, you are tired of the promise of travel,” a line I use often. That, in essence is what our promise is to the global travel industry: that we are eternally curious about the business and creative possibilities of travel and what it means to the world at large.

That is what gives meaning to *everything* we do as a company. That is what inhabits our culture.

We see the effects of that work best at our flagship Skift Global Forum in New York, where you all see the best of Skift brand and culture comes to life in every way possible. That is why the team dinner at the end of the Forum is such a great feeling — an adrenaline rush — , even though we are beyond-dead tired at that stage.

“Assume Good Intent”

Now to the part about keeping the culture. Those of you in our New York office may have noticed these two new “posters” that came in recently (still waiting to be mounted on the walls). They give you a sense what is at stake to keep that culture we have and why it matters.

It hasn’t been easy to work at keeping our culture-stems-from-meaningful-work culture and it won’t ever be. It is supposed to be hard, the hard is what makes it great.

We have gone through a growing up — the “Young Adult” phase as I call it — of Skift over the last year, especially the first half of this year. The growth pains, on team organization, on processes, on some hiring misfires, on my own transition to hands-off management, all of these gave us a needed push to evolve in so many tangible and intangible ways in the last year. And that Sisyphean task on our evolution continues in quiet ways every day.

“Assume Good Intent.” That is a phrase I came upon in the last year and I have been so taken by its radical simplicity. I am really struck by the open vulnerability implicit in it. So much of the meaningful and non-political nature of the team, of our intra-company relationships, of your relationship with the company, can be preserved if we use good intent as a construct for navigating the work life. The Skift Life Principle, if you will.

In practical terms that means our responsibility as a company to you is to continue to build the boutique, humane company we celebrate in our core values, that we put your professional and personal lives first in building the company, and that you buy into that intent. That we assume you have the best of the company at heart in every bit you give to it, through your inevitable ups and downs of work life you have here at Skift. That we are all in it to do great work that gives great value to our readers and subscribers. And while we are at it, we are having a great time doing it.

“Empower From Behind”

There are so many reasons why our annual retreat last month in Puerto Rico was so meaningful. That glorious last evening at the beach in San Juan, that first photo above captures so much of where are today as a team that really likes being with each other, that easy camaraderie we have with each other. I am humbled by the thought of it, blessed that you all are part of it, and proud of how far each of you have come in your long and short journeys with Skift.

I posted the photo on my social media channels with this language: “If you’re ever so blessed in your life to build and be with a team like this, make sure you end up celebrating them & with them on a beach and a sunset like this. As Skift retreat in Puerto Rico comes to an end, feels like a seminal moment in the growth of our company, each of us.” And the amazing part is it came through to others who saw this photo, in the reactions that I got after, two of which you can see below which capture the gist of it.

The second comment from Jason, a long time industry friend of ours, is particularly resonant to me and as I have thought through it since, the visual presented through this photo has been very clarifying on my role — and indeed the role of our management and team leaders — going ahead. Instead of “lead from the front” as I have done for first five years, a necessary role to build a company in its infancy, I am now transitioning to “empower from behind” as is the management of our company. From being *the* face of Skift to being a face of Skift is role that I now cherish.

So the next time anyone asks me that culture question, I now have a better answer: I will just show that photo above. This is us, this is our culture.

***********

P.S.: If they ask me for more visual evidence of our culture, I’ll show them this photo below. I think I don’t have to explain anymore why I love it so much.

The Best Slide I Ever Made

Exactly 16 years ago in the depths of economic despair post-9/11, I started an incongruously-named blog called paidContent. It started as a way to track the then-moves by media, entertainment and information companies to get revenues directly from their users, an attempt to pull back from the Web 1.0 historical “mistake” of giving away everything for free online.

It was 2002 and still early enough in the digital media world. I started it as a solo blog reporting and emphasizing the need for 1) the media companies to embrace digital because the consumer were moving online and mobile 2) the need to diversify revenue streams, including getting direct user revenues through “paid content” initiatives.

I worked out the editorial mission of the company two years later — when the blog became a company — “Our belief is that in the near future, all media will be digital media, and we are helping define sustainable business models and innovation within this sector.”

It also became my personal ethos, to build media companies that are sustainable and innovative, a calibration that as we all now know is amongst the hardest challenges you can give yourself as an entrepreneur, especially in media.

16 years of being rationally contrarian, on building media businesses, on reporting, analyzing, opining, ranting and shouting about media’s hype cycles, on being the official/resident hype buster of the media world, has been hugely rewarding and frustrating in equal doses.

It all came together one evening earlier this year, as I was working on a presentation I was going to give to the Skift team, as part of our semi-annual SkiftOne day, a day where we discuss — and present about — the state of our business.

My opening presentation was about the first half of 2018,the growth plans for Skift for coming year, and the opportunities and challenges for us as we grow. Towards the end of my presentation, I added this slide you see above, almost as an afterthought.

It ended being my favorite slide I ever created.

I could hear some audible gasps when I showed this slide to our team, that reaction alone made the years of toil all worth it. The clarity of our purpose, it all converged in that moment.

The realization that all the crap happening in the larger media ecosystem we don’t have to give a shit about, that is a deliberate choice-- million hard choices along the way -- we have made to build a meaningful media company that matters to our people, who then create amazing work that matters a lot to people in the world’s largest industry, helps them change the direction of this giant sector, is an incredible one to put down in this slide, for me, for our team.

Every bit of sanity I have lost, and God knows how much I lost along the way, is worth just to be in a position where I could visualize my career’s output -- the companies we have created -- in the way it came together in this one slide.

Creating media for media’s sake, versus creating media for creating daily value to your users, that has been the difference, that is this slide.

P.S.: Just in case you’re curious how I ended that presentation, here are the last two slides following the one above:

#entrepreneur #media #business #skift

My Biases In Media Business: A Primer

Me with my Tweets, visualized.

For those who have followed my career, many try to decipher biases in my media business writing/analysis/rants (aka Tweets), especially those on receiving end of them. Certainly I have my share of media people I have pissed off with my Tweets, and many who assume I am out there just to slash and burn.

So, I’ll try and explain. I have been a media operator for 16 years now, have built two boutique media companies, have spent 10+ yrs as media business reporter (haven’t been one since 2010) and have gone through every up & down you can imagine in media, as a journalist and as an entrepreneur. And as an immigrant in America. I am a media operator, hence I critique. I am biased against unearned privilege in media (which is sadly a majority of media owners and executives) and the essential bullshitness of the whole ecosystem around “future of journalism/media,” so much of which media founders and executives inhabit as an act. I am biased against scenesters in media, a category in which majority of digital media startups (and founders) fall, with little long term conviction of the discipline required to build something long lasting in media. I am biased against over-complication of media, biased against those who claim to be reinventing media with their new companies, biased against those claiming supposedly new business models in media. All of which is bullshit. I am biased against the valuation chasers in media, also the majority of digital media startup founders. I am biased against media companies/founders/executives pretending to be tech companies, also a surprisingly high number. I am biased against momentum/herd venture investors in media, with little understanding of the long term nature and nurturing of media and nature of returns. I am biased *for* the media operator, the one keeping their heads down and executing. I am biased for the underdogs in media, of which many exist but don’t get the spotlight. I am biased for what I call the “Small and Mighty” media companies, companies and people with deep impact in their domains. I am biased for those creating media with a confident worldview and understand the primacy of it – and primacy of editorial - above all else, in building a media company. Conviction is a very under appreciated talent in media. I am biased for the older entrepreneurs in media, those reinventing their careers, those proving the skeptics (many times me amongst them) wrong. I am biased for journalists-becoming-entrepreneurs, it is amongst my only evangelizing functions in life. Sadly many of them become future-of-journalism types, those I am biased against. I am biased for those media entrepreneurs betting on longform text, the past, the present and future of media, instead of running after every new formats and pivots emerging. I am biased for those creating finite, packaged media in an age of overwhelm. I am biased for those media entrepreneurs & executives who see opportunities outside the general catch-all media, pick the right topic & own it. No surprise there, I have lived all my life in vertical media after all.

Above all, I am biased for those *always, always*, doing their own thing in media.

Hope that explains it!

#media #entrepreneur #business

Small And Mighty: Why Small is Having A Big Moment

Last month I gave a talk at the Chicago Ideas Festival, as part of the entrepreneurship track, along with other well-known entrepreneurs, all of us women or PoC.

My talk focused on what I know best: building boutique companies and why small companies matter. While everyone exhorts you to think big, I have built two successful companies embracing thinking small and deep. My talk focused a bit on my journey and why small companies — with outsized influence — are having a moment.

The full talk is now available to view, below:

I led off with this video trailer of the upcoming film Downsizing, as a precursor to why small is really the future of the world, in many ways beyond this improbable comedy.

Chicago Tribune did a good accurate summary of my 10 minute talk, which I am extracting below, along with my slides.

Rafat Ali, CEO of travel news site Skift, noted that he was possibly the least well-known person on the stage, but that’s kind of his point: Don’t focus on scale, but resonance.

“Young people… are navigating their life through a lens of travel, food and retail. In an age where community, family and others are being replaced by digital, where you’re also a lot more isolated in the world as you grow up, people have latched onto brands,” Ali said. “So brands then become a conduit to how you live your life. Young people are looking for a shared sense of community with their brands… Small is where these types of businesses are possible.”

Aim instead, he said, for outsized influence in specific areas.

“In the internet age, one of the big words that came about was scale. You can’t survive in this age without scale, meaning having big, giant, giant companies: Amazon, Facebook, Apple.

The full PDF of the presentation is here: Small And Mighty: Why Small is Having A Big Moment

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