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  • Writer's pictureZach Servideo

100: Boston Speaks Up with Nick Cicero, Media Entrepreneur & Analyst

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs.

Nick Cicero is an analyst, entrepreneur and growth expert operating at the intersection of digital media and advertising. He made a name for himself in the 2010s when he founded Delmondo, a social video analytics company. 

Founded in 2014, Cicero quickly established Delmondo alongside established media measurement companies by introducing numerous industry firsts, including the first enterprise analytics solutions for Snapchat, Instagram Stories, and Facebook Live used by clients such as ABC News, the NFL, WWE, Fox, UEFA, Paramount and more. He and Delmondo also co-produced the first Snapchat Branded Long-Form Ad Series with Marriott Rewards. 

Raising only a single angel investment round, Cicero steered Delmondo into a profitable startup that garnered millions in revenue, hundreds of loyal customers; and set new industry standards culminating in its acquisition by Conviva in 2018.

During his time building Delmondo, Cicero was also a cofounder of TVREV, an analyst business reporting on the convergence of TV and digital media. He partnered on TVREV with a who’s who list of media executives that all participated in Conviva’s angel investment round –  Gary Vaynerchuk (VaynerMedia), Jesse Redniss (former WarnerMedia, current founder at Qonsent) and David Beck (current Brightcove COO) – who collectively operated as BRaVe Ventures

Cicero stayed on at Conviva for several years to lead Conviva’s social intelligence business in a VP of Strategy role. At Conviva, Cicero focused on extending their portfolio of measurement products that enable video publishers, sports teams, leagues, and streaming TV providers to get a 360-degree understanding of the viewer journey and grow viewership, engagement, and revenue. 

He departed Conviva in 2022 to pursue consulting opportunities and explore new entrepreneurial endeavors. He joined the ranks of consulting firm Value Creation Labs (VCL) in 2023, establishing himself in a GTM Lead role for VCL and its partners such as Vevo, Precise TV, PadSquad and T-Mobile. 

Cicero is a regular speaker at industry trade shows, and is an expert commenter on industry trends such as his analysis of the $5 billion Netflix-WWE deal featured in The Drum. He also has a passion for mentoring the next generation of media entrepreneurs. He’s an adjunct faculty member at his alma mater, the S.I. Newhouse School of Public Communications at Syracuse University, where he recently announced the formation of the inaugural Emerging Leaders Alumni Board of which he plays a lead role. 

We explore Cicero’s impact on the media innovation community, what he’s up to at VCL, and much more in this latest  ‘Boston Speaks Up’ episode. You can listen to our podcast discussion embedded below or on any podcast platform you prefer (YouTube, SoundCloud,Spotify, Apple Podcasts, Stitcher, and Google Play):  

Before we dive into the written Q&A, here’s a teaser clip of Cicero sharing insight about the importance of founders being scrappy without spreading themselves too thin: 

Written Q&A: 

Where did you grow up and how would you describe your childhood?

I grew up in Upstate NY - when I look back on my childhood I have nothing but good memories. My parents were hard-working and taught us the value of a hard day’s work, but also the importance of art, music, creativity and the outdoors. My dad was in construction and worked hard but always wanted to provide us with the best opportunities in life. My parents are where I get a lot of my entrepreneurial knack from, my dad was always doing side jobs and when he started his own construction business and my mom constantly fueled my creativity and encouraged me to try new things. I played a lot of trumpet, fishing and backyard hoops with my friends. 

Can you tell us about your entrepreneurial journey starting out in 2003 with Modern Day Cicero? Any fun stories from your team working with clients like Cyhi the Prynce, NY Giants, and Kendrick Lamar?

In high school I started to learn how to produce music on computers, combined with access to the internet started using platforms like Myspace or forums to connect with other people online. When I realized that I could find people who would pay me to make music for them, I really dug in and started producing and uploading music online. As I entered college I had two key things: a lot of free time and 24/7 access to the internet, something I never had before. 

Facebook was brand new (I had to borrow a friend’s digital camera to put a picture online) and Myspace was the game. I started to teach myself some basic html, css so I could build simple websites, blog and customize Myspace pages. 

During this time I met music licensing professionals from NY and LA through the internet and ended up placing songs on TV networks like Fox and A&E. One of the memorable campaigns I worked on during this time was for Burger King, I helped them chop up Garageband files to offer a remixable track for people to play with online. 

As social media started to develop more, I transitioned from producing music to working with brands and artists on what was now known as “social media” marketing - one of the people who supported my music career Big Mike saw the value of social media and this led to working with Kanye West’s artist CyHi the Prynce running his social media channels and helping to launch a few mixtapes. 

As the Lead Strategist of LiveFyre, what was your favorite project you ever worked on? (ie: Oprah’s Lifeclass, Sports Illustrated Tailgate Tour, Eminem’s Lyric Campaign, etc.) Any big takeaways from that role?

Two that really standout are the PlayStation 4 Launch and Oprah’s Lifeclass. At Livefyre, we were really one of the first companies to use social engagement and engagement data as part of customer experience - building some of the early Media Walls that you’d see on websites, events and activating social content through TV. 

For the PlayStation 4 campaign - we partnered with Playstation and their agency to create the launch site when the product was announced. We built a widget that used trending data to rank the launch games based on their popularity and volume of social media comments from fans. We curated top youtube review vidoes of the launch as well, leaning into the gaming creator community before it was the massive industry it is now.

For Oprah’s Lifeclass - I was fortunate to go on-tour with Oprah in Chicago and Dallas for her Emmy-winning series which was an amazing experience to work alongside the Oprah team. They truly are incredible in what they’re able to execute as a media business but also stay personable and relatable to her scores of female fans. From a technical side, with Instagram having just launched videos on their platform, we were able to quickly integrate that API in time to put the first Instagram Video on TV, which I was really proud of.  

You've been a leader in the digital marketing sector for over 15 years now. What values or principles have guided you throughout your career to always stay on top of (and ahead) of what’s next?

Never stop learning. Never stop connecting. Never stop helping others. 

Outwork everyone.

Stay curious. Write down your thoughts.

Across the 4 years you spent growing Delmondo as the Founder and CEO, what were some of the biggest learnings you took away from this experience?

There are many individual learnings about all different facets of starting a software company from scratch, building with social platforms and ultimately exiting that I could talk about but I think there’s one main takeaway that people can learn from the Delmondo story.

You have to adapt and innovate quickly in order to push your business ahead. When we started out we focused on being a hybrid influencer marketing agency and software. We recruited influencers who created content for brands and then we measured it in our platform. After the first year we quickly realized there was a much bigger opportunity with being a social video analytics SaaS platform and all our existing customers would buy it. By being nimble we were able to pivot quickly and embrace the unique value we had developed as the first analytics for Snapchat. 

What was the most fulfilling part of the journey growing Delmondo? Was it the early days building the team, once you started seeing real growth, acquisition day…?

The most fulfilling part was seeing our team's hard work translate into meaningful industry contributions, such as pioneering analytics solutions for emerging social platforms. Witnessing the direct impact of our work on our clients' success, and helping shape the future of social video analytics, was incredibly rewarding. The journey of growth, from a startup to an industry leader, and finally to profitability and then acquisition, was a testament to our team's dedication and innovative spirit.

Since leaving Conviva, I also am always excited seeing members of my team grow and thrive in their careers as a result of the work and relationships that the company led them to. 

Once acquired by Conviva, how did your role change? Did you still have the same passion for the work?

Post-acquisition, my role evolved to focus more on integrating Delmondo’s solutions into Conviva's broader offerings while still leading the social intelligence business unit. As VP of Strategy I sat at the intersection of product management and corporate strategy, working closely with product teams to develop our roadmap and new product features, meeting with customers, and helping our sales and marketing teams advance the company’s position. 

The passion for the work not only remained but grew, as I had the opportunity to influence a larger scale of operations and contribute to shaping the future of video streaming analytics. The transition allowed me to leverage my experience in social video to enhance Conviva's suite of products around audience measurement, content engagement in streaming video and work with major companies like Disney, NBCU and DAZN during pivotal moments of their growth.

Unleashed again as a consultant-entrepreneur working alongside folks at Value Creation Labs, what do you find most fulfilling in your work? Any favorite stories thus far?

I really enjoy the entrepreneurial spirit of VCL, everyone collaborating together on projects bringing their own expertise into the mix to achieve great work. One of the most rewarding projects so far is the partnership we have with Precise.TV. YouTube is currently at the center of the living room when it comes to media consumption, with everyone from kids to grandparents turning to YouTube more than any other video platform. With so much attention being spent there it has been rewarding to work with Precise.TV on finding unique stories and trends in kids media consumption and helping them tell that story to the industry.  

Where are you most excited about in 2024 and beyond?

Among many things, one in particular is the Newhouse Emerging Leaders Board that just launched at the Newhouse School at Syracuse University that I have been fortunate to co-chair. We’ve brought together 18 young alumni leaders from companies like Google, Amex, NBCU, Instacart and more together to advise the university, develop mentorship programs for recent grads, and build a strong Newhouse network of alums to help eachother out in the communications/advertising/media industries.

As an adjunct professor at Syracuse University, what advice do you have for young innovators who aspire to make a positive impact in their sectors like you have?

My advice is to embrace curiosity, seek out diverse perspectives, and not fear failure. Innovation is as much about learning from setbacks as it is about celebrating successes. You have to just start the thing! Cultivate resilience, stay informed about industry trends, build a community of people who can support you and always look for ways to apply your knowledge in solving real-world problems.

What’s your favorite part about mentoring the next generation of innovators?

I like to think about it like “unlocking the gate” - mentors can bring experience and relationships but they also can give it to you straight. This unlocks your true potential when you know you have someone who believes in you. I have great mentors like Jesse Redniss who have shaped my journey by empowering me and challenging my beliefs.

Tell us about a particularly challenging moment in your career and how you overcame it. What did you learn from that experience?

A particularly challenging moment was navigating the uncertainty of the early days of Delmondo. After I had the initial investment from Jesse Redniss, David Beck and Gary Vaynerchuk, I met with a number of VC’s trying to raise money for our business.

Snapchat didn’t have an API yet, Facebook Video was a thing for friends, Instagram Stories didn’t even exist yet and we were facing skepticism about the viability of our business model. Despite this, we just kept on making money. We kept our costs low, leaned into thought leadership to establish our industry presence and continued focused on proving the value of our solutions through relentless innovation and customer success stories. We became official Facebook Measurement Partners as they rolled out more video products and launched the first analytics for Facebook Live and Instagram Stories. This drove more and more word of mouth referrals and led us to become profitable in 2018 when we were acquired. 

This experience taught me the importance of resilience, the power of a clear vision, and the value of customer feedback in shaping a successful business.

Finally, can you share your vision for the legacy you hope to leave behind in your career as an innovator in the digital marketing space?

I hope to leave a legacy of innovation and fearlessness in the world of entrepreneurship and digital marketing. Proving that new mediums need new forms of measurement to use data to tell better stories. Demonstrating that you should ask the hard questions and solve the hard problems and not wait for the world to tell you what to do.

FINAL QUESTION: We like the idea of ending our episodes with a challenge for the  listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from  a book, creating a new healthy habit… What is one challenge you have for the listeners? 

Spend 15-20 minutes minimum per day in nature. Taking a walk, stopping to listen to the birds and the wind and appreciate the natural world.


You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting

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