Ari Evans of Maestro: “Live streaming brings fans closer and makes them part of the experience”

Live streaming brings fans closer and makes them part of the experience. That is a game-changer for an industry that has been rocked during the pandemic. On a business level, it also opens up new revenue streams for a sports organization. New technologies have changed the way we engage in and watch sports. Sensors, Wearable […]

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Live streaming brings fans closer and makes them part of the experience. That is a game-changer for an industry that has been rocked during the pandemic. On a business level, it also opens up new revenue streams for a sports organization.


New technologies have changed the way we engage in and watch sports. Sensors, Wearable Tech, Video Assistant Referees (VAR), and Instant Replay, are examples of new technologies that have changed the way we play and watch sports. In this interview series called, “The Future of Sports; New Emerging Technologies That Are Disrupting The World Of Sports,” we are talking to sports leaders, athletes, sports tech experts, and sports equipment companies who can talk about the new technologies that are reshaping the sports world.

As a part of this interview, we had the pleasure of interviewing Ari Evans is the CEO and founder of Maestro.

Ari is an industry thought leader helping creators build more meaningful relationships with their audiences. By inventing new tools and best practices in live stream engagement and monetization, Ari is unlocking live streaming’s true potential as an internet-first experience.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My Dad was a major contributor to my entrepreneurial journey, starting with buying me an original Nintendo console when I was four. That had a major impact because back then games, in general, were much harder than they are today. They required persistence, getting back up and trying again after repeated failures, identifying and tweaking strategies, and perfecting constantly until achieving victory. Looking back, I was hooked on the feeling of improving and the rush that comes from success.

I’ve always been driven with a strong sense of confidence. At the age of 12, when I started my first business on eBay, I wasn’t explicitly planning to be an entrepreneur; I simply saw an opportunity and was curious to explore how I could take advantage of it.

When I was in high school, I played soccer and ran track, which taught me the power of teamwork. That experience was tremendously amplified when I became a raid leader on one of the earliest MMORPGs called Everquest. 4 or 5 nights a week, I would lead 72 people into a very difficult challenge. This role was an incredible early training on how to be a CEO. It required organizational structuring; design, communication, and execution of strategies; and reward allocation. We frequently faced failure and I had to shoulder that, continuing to be positive, optimistic, and determined to succeed to keep spirits (and retention) high.

These experiences, combined with my vivid imagination and strong support from my family and friends, drove my journey in the early days, and even to this day, with Maestro. Much like video games and sports, working in technology is the never-ending pursuit of better, of innovation and personal improvement. As much as they were guiding lights for me as part of the journey, they’re, in many ways, the same guiding lights for the team at Maestro.

Can you share the most interesting story that happened to you since you began your career?

I enrolled at Cornell planning to be an electrical and computer engineer, but in my sophomore year, I stumbled across a brochure about a relatively new major that sounded like a good fit for me. I switched majors soon thereafter to Information Science, Systems, and Technology in the engineering school. One of the classes I took in the major — Human Computer Interaction and Interface Design — had a profound impact on me. I immediately fell in love and the affair was amplified by books like Dan Norman’s The Design of Everyday Things. I knew from then on that UX design and product development was part of my calling. At Goldman, I was limited in being able to explore that professional path, which was one of the reasons I left.

But when it came time to graduate from grad school at Stanford, I still wasn’t ready to jump into entrepreneurship full time. I felt that a product management role was what I needed next and Zynga had a great opportunity available, so I jumped onboard their incredible rocket ship and rode it through the IPO.

The experience at Zynga was invaluable. I worked on CityVille, the biggest game on Facebook at the time, with over 20M daily active users. It was a wild ride and I drank from the proverbial fire hose, designing features, forecasting their success, managing pods of engineers, artists, and designers, and managing revenue pipelines. I loved the interdisciplinary aspect and level of responsibility in the job. I was surrounded by an incredible group of product managers who challenged me to unlock my own potential — ideal conditions, in which I thrive.

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

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” — Theodore Roosevelt

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I would say my father and grandfather. They were the biggest contributors to my entrepreneurial journey, starting with buying me an original Nintendo and a plethora of other examples along the way. There’ve been countless others along the way, but they’re the two that really sparked something in me.

For example, it was my grandfather who first introduced me to the stock market as he was an active trader and avid researcher. I’ve always found it fun to watch trends and anticipate their implications, dreaming up ideas about what the future might hold. Tech is an area where I felt like I had a good sixth sense developing. So, that was a natural sector to start with, given it combined a lot of my strengths.

It’s these micro-examples that add up to make us who we are — the nintendo, the stock market introduction, Ebay business, my mentors, professors, our board and so many others; each interaction empowered me with a new perspective, skill or support.

Is there a particular book, film, or podcast that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

There are so many I could list here — and in general one of my big points of advice for any entrepreneur is to read more books. It’s one of the biggest cheat codes I have found in my experience. The book I’ll pick here is How to Decide by Annie Duke. Everybody, and especially entrepreneurs, need to make a tremendous number of decisions on a daily basis. We’re generally fairly bad at it because we’re never taught any frameworks to help guide us and it turns out that the evolution of human biology biases us in ways that can be more harmful than helpful given the modern human existence. Ultimately, the book teaches how to avoid “resulting” which is a behavior in which we associate the quality of decisions with the quality of the outcomes.

It’s a simple observation that is literally game changing in how to approach decision making and, perhaps more importantly, has a tremendous impact on your mental state. I, like many, tend to beat myself up over bad results, but through the use of this workbook, I have identified that in most of those situations, the decisions I made were actually good ones; it’s just that chance didn’t favor me in the outcome.

When we accept chance and think through our choices with probabilities of outcomes and don’t fall victim to hindsight bias, we feel better about our choices and increase the likelihood of achieving our objectives. Given the absolute marathon of a journey that running a company represents, this book is a secret weapon to extend your stamina and alleviate some of the roller coaster along the way.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Be an exceptional listener — leaders need to be very good at listening — to their customers, to their team, and to the market — and then be able to synthesize information to inform their strategic decisions. As Maestro has evolved, we have been continuing to expand to new market segments. It turns out that though the needs around live video are similar across the board, there are nuanced differences that turn our product into a need-to-have vs a nice-to-have. In particular, individual creators and small businesses are much more driven by being able to sustain their livelihoods via their streaming careers so monetization is much more at the forefront of their pain points. These learnings have caused us to target our messaging for each specific customer segment and the results have been great so far.

Relentlessness — Call it thick skin, call it masochism, or obsession, but relentlessness is a key to my success. Like every entrepreneur, I’ve been rejected more times than I can count. Especially in the early days, there is likely going to be a gap between your vision and the first implementations of your ideas. You’ll need to find the stamina and inner strength to push forward and find the right investors who align to your view of the world. That said, it is critical to simultaneously be optimistic and realistic in your approach. Early on, our basic thesis was that engagement is more important than reach and will drive increased watch time, retention, and revenue. Even though we ended up proving this, that thesis ended up not being enough to drive massive adoption of the product; ok, so users spend more time — so what? Does that improve the customer’s actual underlying KPI? So we helped the customer capture thousands of email addresses. So what? Is there a dollar value that can be attributed to an email address? In general, customers can more easily grasp propositions that save them time, save them money, or make them money. It’s best if you can align to one of those and prove it in a very obvious way. Relentlessness helps you power through these kinds of evolutions in order to better address product-market fit.

Dream Big — This is one of Maestro’s core values and we’ve chosen it for a reason. Iteration is of course necessary, but sometimes the real breakthroughs come from dreaming bigger. Zooming out of the problem you’re trying to solve, asking the “what if?” question and seeing where it takes you. Of course solving bigger, hairier problems also tends to capture investor attention (Elon Musk comes to mind) so that can be a plus on the fundraising side — investors love to fund ambitious entrepreneurs. It can also provide new perspectives, go-to-market strategies, product innovations, and all kinds of other useful byproducts. Maestro itself was conceived of by dreaming bigger, asking “what if video wasn’t just a one-way experience?” and “what will be the next phase of the evolution of video after the core challenges (i.e. consistent quality and delivery, etc.) are solved?” Even more recently, we’ve dreamt bigger to imagine how to both double down on our assets and expand our value proposition in new ways. This kind of thinking helped us formulate our market positioning, develop our product roadmap, and evaluate new growth opportunities.

How have you used your success to bring goodness to the world?

As we continued to evolve Maestro, one of my proudest moments came this year when we were able to accelerate the release of our Maestro monetization tools. So many were looking for solutions to bring new revenue streams, as their previous world had come to a screeching halt.

I’m incredibly proud to say that since Spring 2020, we’ve helped our Maestros bring revenue back online across a wide variety of industries — brands, creators, sports, worship, politics, music, comedy, film and many more. We’ve done this in a way that elevates human connection in the digital realm, immersing participants into experiences that build more meaningful relationships.

  • 1M+ Unique Purchasers

An exciting milestone for the company; 25 40,000-person stadiums worth of people have made a purchase since April 2020. 450K of them were new this quarter.

  • 12M dollars+ Paid Out to Creators

Nothing speaks to our mission of growing the GDP of the creator economy than watching our customers get paid to do what they love since we launched our monetization tools. 5.7M dollars of that was paid out this quarter, and we’re just getting started

  • 93Kdollars + Avg Incremental Earnings per Customer

Monetization use cases continue to flourish with customers making an average of 93,000 dollars per year with us, which is purely net new revenue, complementary to existing revenue channels.

Additionally, we were able to aid in communication efforts around voting, COVID, social justice and so many more focal points in need of platforms. All of which, I’m humbled and inspired to have played a supporting part in. Truly blessed to be in this position today, and that’s something I am reminded of often.

Ok wonderful. Let’s now shift to the main focus of our interview. Can you tell us about the sports technologies that most excite you at the moment? Can you explain why you are passionate about it?

It’s hard to argue that live streaming has completely changed the way viewers enjoy esports and sports. Alongside the technological advancements, what has evolved more radically are the philosophies and approaches to creating experiences that are “web-first.” Streaming is undoubtedly the future and the scales have only started to tip this direction over the past year or two. Mainly it’s about starting to think about the content less as a one-way static asset and more as a two-way interactive experience that is personalized to different viewer segments. I view this as a win-win for all parties because this approach creates deeper fan affinity, increasing watch time (and ad revenue), and also opens the doors to many new monetization opportunities that take advantage of audience segmentation. At a physical event, VIP is completely different from GA in the bleachers; why isn’t there that kind of distinction virtually? Why should a season holder VIP viewer be capped at the same ad CPM rates as a casual viewer? This is the reality of modern broadcast experiences which simply points to the massive opportunities ahead. The timing is particularly significant as physical venues won’t be able to stuff as many fans into their stadiums as they once did nor will audiences be as eager to attend as they once were. That said, the changes being born out of the pandemic will permanently change broadcast strategies for the better and force a renaissance of sorts in the field.

In our experience we’ve had the honor of working with many top sports properties, ranging from the Dallas Cowboys to the Golden State Warriors, CBS on the PGA championship, and even smaller leagues like Bowl TV. The benefits to adopting a “web-first” strategy for broadcast are significant and increasing daily as more companies explore new dimensions of engagement and monetization. We are particularly excited by a few different vectors of technology:

  • Telemetry: how can I as a viewer understand more about what is going on in the game? Sensors have come a long way and are evolving both the moneyball side of the business as well as education for aspiring athletes, and even interactive broadcast experiences for fans.
  • Production automation: everything from cameras automatically producing a broadcast with the best angles at all times to using stats APIs to automatically drive engagement and education during a stream.
  • Free to play and real-money gaming: these kinds of experiences are getting merged into layers over the broadcast, making it easy to “watch and play” in ways never before possible. As legislation continues to sweep the US, we see this as a big growth opportunity.
  • Social: new ways for fans to interact with each other around the game in real time similar to how they do in real life; watch parties, heckling and bragging for fantasy performance, showing your excitement, getting on a birthday or kiss cam, etc. There’s so much to explore here.

How do you think this might change the world of sports?

As we’ve seen during the pandemic when there’s been empty stadiums or arenas, sport is nothing without fans. Everyone watched a game during the last few months and it felt somewhat soulless for fans.

What interactive live streaming does is offer franchises, teams, players, leagues, institutions and coaches a way to develop a direct relationship with more fans. How many people can say they’ve had a 10–15 minute 1-to-1 conversation with their favourite basketball player just before a big game? That’s made possible with live streaming. You can watch games with your friends who live in a different city or state. You can experience drafts in a completely different way. You can attend a virtual Watch Party. It doesn’t stop there, this includes PPV and free formats, subscription or membership based programming, shoppable and gamified destinations for nearly every sports event format across conferences, preshows and postshows, jersey reveals, in-stream fantasy broadcasts, fan-driven draft parties, virtual tailgates, press conferences and so many more. Anything is possible.

Live streaming brings fans closer and makes them part of the experience. That is a game-changer for an industry that has been rocked during the pandemic. On a business level, it also opens up new revenue streams for a sports organization.

The future of the sports industry is interactive, and live streaming could soon become the primary medium for fan engagement in traditional sports, much like it is in esports. In our most humble opinions, it’s about damn time.

Keeping “Black Mirror” in mind, can you see any potential drawbacks about this technology that people should think more deeply about

Black Mirror did an incredible job of forcing us to imagine in greater detail what our life and society might be like if technologies evolve in various ways. We can take the content and have a negative reaction with fear about the future, or we can heed the lessons and make changes to avoid the less than desirable outcomes.

In sports in particular, the above technology vectors appear relatively benign as far as scary potential short-term consequences. Are there drawbacks to athletic heroes being more accessible than ever before? Potentially, but if so, it doesn’t feel like we’re anywhere near that outcome. What about the idea of turning a human into a data-producing machine and then evaluating that person only based on their stats? Whether or not we disagree with this ethically, the ship has sailed; fantasy sports and moneyball are good examples.

Thinking further out is where things get complicated. When will we see the first cyborg games? Will human sports be as interesting when we have cyborgs competing against each other? Battle Bots certainly has a dedicated following…

One of the most exciting and positive prospects of technology is that we will likely see many new sports or flavors of existing sports be developed. Take a look at the Drone Racing League, World Chase Tag and the Fan Controlled Football League as great examples. What kind of sports can we create in zero-gravity environments? If nothing else, interactive live streaming will likely accelerate the awareness of and popularity of these new sports if they are destined to be successful. The combination of the power of the distribution, immediate monetization channels that don’t rely on reach (very important), and the immersiveness of experiences that can turn new sports into mega properties quickly. Esports demonstrates this phenomenon constantly as new games are released and esports programs develop.

What are the 3 things that concern you about the sports industry today? Can you explain? What can be done to address or correct those concerns?

Media rights — not exactly a concern but more of something to watch; how will media rights change as the streaming paradigm continues to evolve and flourish? We’ve seen leagues go deeper into their own apps and direct-to-consumer distribution and in some cases (e.g. the NFL), they have seemingly at least considered abandoning that strategy. Media rights in esports have not become as big of a revenue stream as many had hoped; it’s not clear that this situation will change anytime soon.

Slow rate of innovation — broadcast formulas have been largely unchanged for about a decade. That surely isn’t due to a lack of companies trying to help evolve the space. There are a combination of factors at play; for one, there’s a general aversion to risk — anything new is risky by default. Second, there is a lack of precedent for many of the new monetization opportunities, e.g. NBC selling MLB merchandise via a Fnatic integration; how does this deal work? We have yet to find an existing deal to what seems like a very basic use case. Third, who has the rights to add interactivity to the stream? This is a pandora’s box across the sports ecosystem. These questions need to be answered — by big players — to set the stage for everyone else.

Gambling — we are big supporters of legalizing and regulating what is already an enormous market; the question is how to provide proper safeguards that keep fans from ruining themselves financially. Integrating these experiences into the broadcasts adds to the convenience factor and increases the volume of transactions, so we’ll want to be confident that appropriate legislation and cultural guardrails are in place.

Fantastic. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

#1 Validate before you build

It’s fun to build things. Whether you’re a product person, engineer, or designer, there’s a feeling you get when you’re looking at or using something you’ve created. If you want to build as a hobby, by all means, do what comes naturally. If you want to build a big business, you should validate your idea as much as possible before writing a single line of code. A prototype of a cool product idea just testing out the market is much weaker than proven demand for a product that needs capital to actually create. The latter is significantly lower risk to all parties involved, least of which is your potential investors and most important of which is you and your team. You can put together a simple landing page and signup with a Wix website in a weekend and start testing the market demand. Force yourself into this practice and it will change the way you approach product design. Paired with this, be sure to have an open mind and let your idea morph and change given the feedback you are receiving — focus on discovering a pain that you can solve. To be candid, I wish I could tell you a story about Maestro that fits with this advice, but I can’t. We first built a cool piece of tech and looked for a problem to solve with it; this almost killed us at least a couple times. We got lucky and while our customers have validated our product, we are incorporating customer research into all future R&D. Please save yourself immense headache and stress and validate first.

#2 Use the jobs to be done framework

Products generally fail because of a lack of deep understanding of the job that the customer is hiring your product to do. While that sounds fairly obvious at surface level, the theory of jobs to be done is an invaluable framework to increase the probability of success. Asking the right questions and really understanding when and where your customer is when they are having the pain that they need your product to solve likely will change your approach for the better or at minimum refine it further. At a high level, your objective as an entrepreneur should be to pattern match for a deeply painful problem that directly affects a very large market who are willing to pay money to solve their problem. Once you’ve found that, you need to define the pain with as much context as possible. The degree to which you can get this fundamental element right will have the largest impact on your outcome and the ease with which you can achieve it. One of the earliest examples in Competing Against Luck is about smoothies being one of the most successful breakfast products. Why smoothies? It has a lot less to do with the factors you may consider important and a lot to do with a critical piece of the context of the pain: customers need a clean, filling, affordable, and easy solution to eat specifically while driving during a long solo commute to work. This is a perfect example of how understanding the pain in more detail totally changes the product outcome.

#3 People are your most valuable asset

This point is absolutely critical. There are few decisions that matter more than choosing the people that are on your team. Especially in the early days, you are looking for “T people;” individuals who have a wide breadth of knowledge and skills but who have significant depth in one area. Sometimes you hear people — engineers most frequently — referred to as 10X engineers. These are not a myth and I strongly recommend you seek them out. Though you will have to compensate them more, it is completely worth it every time. Not only will you get where you need to go faster, but these people will keep the flywheel spinning without you. They will similarly recruit great talent who they respect and admire and next thing you know, you will have a superstar crew. By the same token, it is important to actively define and work hard to create the culture of your organization so that your people feel the affinity to your company and genuinely care about ensuring its success. At the end of the day, almost every problem that happens in a startup is a people and/or communication problem. You should strive to be empathetic but not emotional in the way you lead. This is fairly nuanced; a good example would be for underperforming employees: ask questions to understand systemic issues, unclear expectations, improperly prioritized task lists, etc. but after you’ve done this, unemotionally cut ties with your hope that an employee will somehow change into something they have demonstrated they cant or simply dont want to become.

#4 It’s a marathon, not a sprint

In extremely rare circumstances startups hit the exact right product-market-timing bullseye. They are so rare that the press loves talking about them. This highly skews your reality and may make you think that if you just sprint quickly toward your objective, you’re going to get there, too. I sincerely hope that luck favors you this way, but it’s not realistic and you should plan for multiple small or large pivots along your way to glory. Though you can train yourself to avoid emotional turmoil, self doubt, and other negative consequences of these changes, the truth is that they will be draining even if you are a world class entrepreneur. To not only survive through these but remain as eager and enthusiastic as you started (which is important), you need to adopt the marathon mindset. Find a pace that is quick and agile, but one that you can sustain for the long haul. This is also critically important for your mental health and to keep somewhat of a balance in your life. The extent to which your life isn’t solely consisting of work will actually make you happier and more effective in your role. The precursor to Maestro was an electronic music blog called LessThan3. It has been a long journey and keeping the right pace has kept our enthusiasm and excitement high as we’ve developed our offering within a rapidly changing macro environment.

#5 Read more books

Throughout my career as an entrepreneur, I have surrounded myself with world-class mentors, founders of unicorn companies, experts in their fields, and other incredibly inspiring individuals. Despite the valuable network I am humbled to have assembled, I still find that books are the ultimate method of acquiring knowledge that can help leapfrog one’s journey to success. There’s something magical about someone distilling what could be an entire career of exploration into 100-something pages that you can absorb in a day or two. Perhaps most valuable about this particular medium is that you can digest the material at your own pace and you can also annotate the pages to get the most out of the material. Best practices are constantly evolving and there are so many lessons that can be learned to help frame your daily work or your strategic vision. Blogs and podcasts are of course also awesome, but there’s something about the depth within a given topic that I find extremely valuable. Wouldn’t it be nice to not put your hand on the hot stove before you burn yourself? That’s what other entrepreneurs are trying to help you with when they write a book for you.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

The ‘Creator Economy’ is a huge topic right now — everyone’s talking about creators and the platforms they use to develop a following and get paid. Facebook’s recent announcement that they are committing 1bn dollars to attracting creators and YouTube’s 100mn dollars Shorts Fund highlight just how much creators and their content is worth to the major platforms. VCs have piled an additional 850mn dollars into creator-focused startups since October 2020 too.

I believe the Creator Economy will be the most transformative job creation engine since the industrial revolution. It’s an economic shift that provides livelihoods and sustains creators who build intangible goods that have real value. I’m mainly talking about the 99% of creators and not the top 1% who typically make up these enormous payout numbers shared by YouTube and others. The truth is that, uUnfortunately, the current design of the ecosystem and the role of major platforms aren’t aligned with the creator’s long-term interests.

Unfortunately, the real story is being ignored. In the simplest terms possible — big tech platforms are taking advantage of creators. Twitch and those mentioned above are increasingly taking oppressive or burdensome percentages of the creator’s earnings, while touting large short-term funds across headlines to detract from these practices to attract more creators to join. For the creators, they get locked into certain platforms because that’s where they have built their audience, become dependent and ultimately lose creative freedom over their content, no understanding of who their audience is from a first party data perspective and only a small fraction of the money they’re generating for the platform.

So we want to create a movement that inspires creators to own their content and everything that comes with it. We saw a similar transformation in the physical goods space with platforms like Shopify empowering merchants to do it themselves with their own storefront on their own website. We are powering a similar movement to accelerate the inevitable parallel that we will see in the Creator Economy.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch, and why? He or she might just see this if we tag them 🙂

This one is easy. Hidetaka Miyazaki, the creator of the Dark Souls series, which has had a profound impact on me over the past few years. In many ways, his games have helped me through the ups and downs of startup life. Time and time again the player is faced with seemingly insurmountable challenges and must watch carefully, often fail countless times in a row, and then execute almost flawlessly to win. In a future chapter of my life, I hope to create something as well designed as these games. Miyazaki-san has my eternal respect and admiration.

How can our readers further follow your work online?

You can follow our work at Maestro here and also through my LinkedIn.

Thank you so much for these excellent stories and insights. We wish you continued success on your great work!

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