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Jonathan Anastas of Alpha Tech: “Better to ask for forgiveness than permission”

“Better to ask for forgiveness than permission.” In my first job, working in media, I had sort of a “Rain Man” moment looking at a set of contracts.” I was like, “Hey, if I just cancel this contract and sign a new contract with this new date, the client will save 17%. With no change […]

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“Better to ask for forgiveness than permission.” In my first job, working in media, I had sort of a “Rain Man” moment looking at a set of contracts.” I was like, “Hey, if I just cancel this contract and sign a new contract with this new date, the client will save 17%. With no change to the plan or delivery,” Despite it being my first job, I just did it and brought it to my boss. He put a cover note on my work and sent it to the client saying, “Merry Christmas, we saved you 17% on the cost of your media.”


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jonathan Anastas.

Jonathan Anastas is a prominent director at Alpha Tech. He is also the CMO at ONE Group, overseeing all marketing for both ONE Championship, the largest global sports media property in Asian history, and ONE Esports.

Jonathan was previously CMO at LiveXLive Media, a publicly-traded digital streaming music service focused on live experiences, where paid subscribers doubled under his leadership. He was also CMO at the Motor Trend Group, a Discovery Inc. company, leading the launching the brand’s first subscription video on demand (SVOD) service. Anastas was part of the senior management team that sold the company to Discovery in 2017.

Prior to The Motor Trend Group, Jonathan served as Global Vice President, Head of Digital and Social for Activision Blizzard, part of the Fortune 500. In this role, he established “Call Of Duty” as the number-one console game on social media, which helped it to become a 10 billion dollars franchise; oversaw digital marketing for the multi-billion dollar launches of “Skylanders” and “Destiny,” achieving record launch sales for new gaming intellectual property; and launched “Call of Duty China” in partnership with Tencent, a free-to-play franchise extension that was the series’ first IP released in China. Jonathan began his brand marketing career as the CMO of iconic gaming brand Atari.

Before his brand marketing career, Jonathan spent more than a decade at the world’s best digital and integrated ad agencies, including Tribal Worldwide, where he was a Divisional President; Omnicom’s Think New Ideas, where he led client service on the West Coast as SVP; and Saatchi & Saatchi LA, where he was the agency’s first Head of Digital.

Jonathan has spoken at the industry’s leading conferences including Cannes, CES, Advertising Week, and others. He sits on the advisory boards of Cluster and other early-stage companies disrupting their respective categories.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I was a musician as a teenager, making records and touring the US and Europe. Over time, I realized I was the default marketer in the band and that I was better at marketing than writing music or playing my instrument.

After college, I began my career on the ad agency side. My first big global job was running Digital for Toyota at Saatchi & Saatchi, and my last agency gig was as a Divisional President at Tribal DDB.

In 2009, I left agency life for the brand side. As a brand marketer, I’ve focused on monetizing and engaging Gen Y and Gen Z around their deepest passions: music, streaming, sports and gaming. At companies like Activision, Atari, LiveXLive and The Enthusiast Network, which we sold to Discovery in 2017.

Today, that’s manifested in my roles as Group CMO at ONE Championship and ONE Esports, my board seat at Alpha Tech, and advisory work I do for several early-stage start-ups in the social cause and entertainment sectors. I’m also an investor in Honeybee, a vegan burger QSR brand in the US.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

While this strategy was set very early by our Founder, Chatri Sityodtong, ONE continues to disrupt by applying a traditional Silicon Valley start-up model, creating scaled digital reach and engagement first, then pivoting to monetization once scale is reached. Chatri and ONE were the first to apply this model to sports.

According to Tubular Labs, ONE was the #4 sports property in the world in 2019 looking at Digital video views, achieved by using this disruptive strategy. At Alpha Tech, the disruption focuses on building an Esports business around casual vs. core gamers and mass casual IP not just focusing on shooters. At the end of the day, we believe that this delivers a larger addressable audience pool.

Can you share a story about a mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’ve made hundreds, if not thousands of mistakes over my career — large and small — and ranging from strategic, execution, financial, and interpersonal. Some mistakes came with big implications and others with small implications.

The biggest learnings have been to ask for help and advice before you’re in too deep. You never know everything, and very little can be done alone.

I have also learned to dream bigger, risk more, and focus more on how something can succeed vs. how it may fail.

On the latter, I’ve been offered investment opportunities and jobs and amazingly successful start-ups. Unfortunately, I was very good at identifying the challenges or the flaws in their models, vs. the huge upside they ended up having. So, I was not able to participate in the big disruptive wins or their profits.

This realization has led to my doubling down on opportunities like ONE Championship, ONE Esports, Alpha Tech, and my other start-up investments and advisory roles, as well as being part of Jason Calacanis’ Launch syndicate.

So, the other lesson is that it’s never too late to learn, grow and evolve.

As you noted, we all need help. Who has been some of your mentors? Can you share a story about how they made an impact?

Mentors are even more important than people tell you they are. The times I’ve not had good mentors or great leaders have been the hardest. While, indeed, you can learn “what not to do” from a poor leader, the upside and depth of learning are far more limited than what one can learn from a great leader. I’ve also learned different things at different times.

Off the top of my head, I learned how to run a large-scale global business from Ian Beavis, who ran the Toyota account globally for Saatchi & Saatchi.

I learned the power of a network by watching — and participating in — the incredible flow of people in and out of Rob Ellin’s office at LiveXLive.

And, overall, I’ve learned the power of “nothing is impossible, never take no for an answer” from the start-up leaders and founders and entrepreneurs I worked for, from Jim Mullen to Rob Ellin to Chatri Sityodtong. The ability to close huge rounds of VC at incredible valuations, build something from nothing, sell ideas before they are scaled businesses, and push through “no after no” all the way to “yes” is a special superpower.

As my work pivoted internationally, I learned a lot from Brian Hodous, Activision Blizzard’s Chief Commercial Officer, who spent most of his true global roles. He’s also a huge music fan, a massive charitable contributor, and a great source of weight training advice.

In today’s parlance, being disruptive is usually a positive adjective. But is always disrupting good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Overall, I defer to disruption first and figure out how to solve the downsides later. If we’re not willing to break things, change won’t happen fast enough. For example, look at streaming. The legacy media companies put “protect current revenue and profit first” and lost leadership. In music and in video, it took big disruption to create pivots. COVID, for example, forced companies like Disney to pivot faster. Now — combining ESPN, Disney Plusand Hulu — they have more US subscribers than Netflix. Maybe a decade earlier, I erred to the “protect what you have and evolve” POV too deeply. I was wrong.

A key learning was watching Activision commit to digital and triple their Call of Duty revenue over half a decade. Or at TEN, we pivoted to digital video from print, launching Motor Trend OnDemand. We sold that small year-old SVOD service and accompanying digital assets to Discovery in 2017 for far more than the whole company’s legacy print valuation.

There has been a lot of debate about the dark side of disruption. I reject much of that for two reasons: First genies never go back in bottles (Metallica fighting NAPSTER, anyone?). Secondly, the upside always far outvalues the downside. Can you imagine life without Uber, Airbnb, Netflix, Venmo, or Spotify? Each one of those verticals is still fought to this day on some level by the legacy haters.

Can you share some of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

“Better to ask for forgiveness than permission.” In my first job, working in media, I had sort of a “Rain Man” moment looking at a set of contracts.” I was like, “Hey, if I just cancel this contract and sign a new contract with this new date, the client will save 17%. With no change to the plan or delivery,” Despite it being my first job, I just did it and brought it to my boss. He put a cover note on my work and sent it to the client saying, “Merry Christmas, we saved you 17% on the cost of your media.”

“When there are many possible reasons for an occurrence, the one that requires the smallest number of assumptions is usually correct.” Almost no lesson has added more value and saved me more time from wasted overthinking. Add “Moneyball” and weighing the level of risk to the level of reward, to Occam’s razor and– together — these form the core for much of my decision-making in business and life.

Speaking of “Moneyball,” that ability to identify undervalued assets — in this case — Esports players who are operating below the pro-level is one of the big disruptions we’re bringing to the market at Alpha Tech. The bulk of the category is looking at metrics like professional Call of Duty players and overlooking someone who might be great at a sport or racing game who’s livestreaming from their bedroom.

We are sure you aren’t done. How are you going to shake things up next?

Given the pace of disruption and innovation today, there is always something new to learn and absorb in marketing. That said, I’ve been interested in flexing my muscles as a P&L owner, a vision driver, and an operator. Joining Alpha Tech’s board has been an ideal opportunity to do that. I’m in a space I know well (Esports) but am tasked with more of a business success role than a marketing success role, working with the CEO and CFO to grow the business and drive shareholder value. I’m also in a deep dive on marketing in Asia and India as part of my role at ONE. It had been several years since I launched Call of Duty China, and this part of the world evolves so quickly that there are always new developments to learn and adapt to.

Do you have a recent book, podcast, or talk that’s had a deep impact on your thinking? Can you explain why it was so resonant with you?

Sometimes, lessons can come from anywhere and can hit you when you least expect them. My wife and I had been very much enjoying “Ted Lasso” as light entertainment. We sort of stumbled into it randomly in part as our son went to school with Jason’s Sudeikis’ daughter.

In the show, Jason plays a Football coach, which is much like being a business leader. His character had been progressing as likable and a good man, but not very driven or successful until one scene, where he makes a big bet on a game of darts with one of the show’s villains. In it, Ted lays out the series’ moral lesson in a monologue where he notes being underestimated his entire life and how much that used to bother him, until one day he drove his son to school and saw a Walt Whitman quote on a wall that changed his entire perspective.

He recalls that it read, “Be curious, not judgmental.” He then calls out the villain for not being “curious” before accepting the darts bet. Not asking how long Ted had played darts, why darts is a passion, etc. It turns outTed is a darts expert. That lack of being curious and that assumptive and dismissive judgment of what appeared to be Ted’s weakness cost the villain the game and the bet.

This entire concept really struck me. Certainly, I’ve been too judgmental in business situations, too confident, too dismissive, and not curious enough. It was a great reminder and a great business lesson. Found in an unlikely place and spoken by an unlikely source, fictional or not.

I’m also obsessed with Spike’s Car Radio. Spike Feresten is a comedy writer who grew up in Massachusetts (like I did) and became a car collector while working for Jerry Seinfeld. He and his co-host — one of LA’s biggest personal injury lawyers-dive deep on cars, motorcycles, racing, and of course, life. Sharing a bit of an origin story, a passion for things that go fast, and having moved to LA from New England around the same time, I just clicked with his POV.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I really believe “Grit” is the greatest underrated attribute. Too easy to dismiss, as it’s not magic, and it isn’t rooted in some sort of exceptionalism. At ONE, our founder values grit and expresses it as “PHD” (poor, hungry, determined). Most of what I’ve achieved in life is from not giving up. And most of my successes come from putting in the work and training harder for longer than others around me. Starting earlier, going later, not skipping out on sweat equity. There are a lot of quotes on the topic, but — being half-Greek — I’ll go old school: “We are what we repeatedly do. Excellence, therefore, is not an act but a habit.” — Aristotle.

Of course, I also agree with Malcolm Gladwell’s version where 10,000 hours of practice, plus life experiences plus luck (being born at the right moment) is the equation for success.

What movements do you believe have the power to add great good to a great number of people?

The health and wellness movement — likely — provides a lot of mass good. For example, vegan foods are good for the planet’s climate, can bring a better diet to much of the world population, and create millions of new jobs, brands, and GDP growth.Also, alternatives to alcohol for social settings are becoming better tasting and better positioned as premium products. Categories like these manage to blend my music past and punk values (Vegan, Straight Edge) with my business desire to disrupt and create. I’ve become a modest investor in an LA-based Vegan QSR concept called Honeybee. We’d like to become the Vegan In and Out Burger.

How can our readers follow you online?

For business observations, @janastas on Twitter, or LinkedIn, for my non-work passions, my Instagram @jabostontola

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