"Clear Umbrella Leadership": Matt Garcia’s Guide to Leading with Kindness

Matt Garcia is the president of The Sasha Group, a social-forward, integrated marketing agency in the VaynerX family, with a specialism in helping growth brands and start-ups. Having taken the reins in February, he’s brought with him a distinctly human approach to leadership, putting collaboration and kindness at the heart of the agency.

It’s a management philosophy shaped by his childhood in a large family, his various mentors at agencies where he developed, and, since 2023, the influence of VaynerX founder Gary Vaynerchuk. Now taking on a new challenge with The Sasha Group, he tells LBB how he’s evolving as a leader to keep himself and his team happy, and ahead of the curve.

The eldest of six kids, Matt was used to wrangling chaos from a young age. He set his sights on advertising at college and jumped straight into account management, putting his abilities to effectively manage and convince others – learned from his experience with his siblings – into practice.

After some years “ping-ponging” between account management and new business roles at the likes of McGarryBowen, Saatchi & Saatchi and Deutsch, Matt eventually combined the two disciplines in 2015, becoming chief client officer at Razorfish agency, Rokkan. There, he developed his business leadership skills and relished the responsibility of answering to the CMO and seeing projects through from sale to completion.

Matt maintained this spirit at his next position, becoming MD and head of account management at Fallon in 2020, before joining VaynerMedia in 2023.

“This was an opportunity to work with someone who's fundamentally changing the industry while they're fundamentally changing it,” says Matt, drawing parallels to those who joined his former bosses and mentors, McGarryBowen founder John McGarry and NSG/SWAT founder Richard Kirshenbaum, during their own ascents in the ‘70s and ‘80s, respectively. “I could think of nothing more exciting than joining Gary [Vaynerchuk] and what he’s building.”

Matt also saw glimpses of another of his mentors, former Fallon CEO Rocky Novak, in the Vayner founder. “One of [Rocky’s] biggest things was something that Gary espouses and practices constantly: making sure people see you have a real interest in them as people.”

He adds, “When people feel you have their back and their best interest at heart, lo and behold, they like their jobs and they’re really dedicated… Rather than sitting and letting things fester, they trust you and see you as someone they can come to and have a human conversation with. It's really served me well.”

After two years of “endless and daily” pearls of wisdom from Gary, Matt has reinforced his leadership style with “kind candour” and a duty to ‘diffuse stress’ for others, moulding this last Vaynerchuk learning into his own philosophy: ‘clear umbrella leadership’.

“It means we will keep you dry when it's raining, but when there's praise and credit, it should go straight through us to the people who did the work,” he explains. “It's amazing what it does for camaraderie and people getting behind a mission.”

While the chance to work alongside Gary was certainly a draw, Matt was also attracted to the forward-thinking of VaynerX – and especially of The Sasha Group. “We were built for the challenge of today, as opposed to adapting a tried and true model to new opportunities,” he says. “We were built to harness consumer attention where it actually exists: in social media. The idea of someone playing this game differently and putting their money where their mouth is was just endlessly attractive.”

After moving across from VaynerMedia to The Sasha Group in February 2025, these reasons to be excited grew “exponentially”, says Matt, thanks to the agency’s focus on smaller and mid-sized companies in “the bottom half of the Fortune 1000 to Inc. 5000 area”, as well as start-ups and newer brands. Since joining, the agency has also launched a consulting arm to work specifically with brands in that early growth phase.

“It's the brands that people under 30 are going to be excited about. These brands feel like they have a real opportunity for discovery, and if we can help grow that – but not force them to grow at such a clip that they lose some of the authenticity and the ‘cool’ – that, to me, is an exciting place to be as an agency.”

Within this model, Matt says the agency’s main challenges are in identifying “where the juice is most worth the squeeze” to focus a client’s marketing, and the ‘drastically different’ reality today that media can no longer be used as a “bully pulpit” for sub-optimal creative. But perhaps the biggest hurdle is to deliver brand messaging in relevant ways to many different subsets and niches of people in an increasingly fragmented landscape.

“You've got a better chance at hitting that intersection if you put out content at volume, and against as many subsets or cohorts of that target as you humanly can,” he explains. “If we can get people to understand that model, the rest is easy and really fun.”

As well as adapting to this new business model at The Sasha Group, Matt has also developed as a leader in these last six months – not just learning new skills, but also ‘unlearning’ potentially detrimental habits observed across his decades in the business.

“One of those things is that you don't have to be right subjectively in the first pass,” he shares. “What you have to do is create an environment where the client will let you find what’s right; the right messaging, the right cut, the right cohort.

“If you can get a client – and yourself, for that matter – to adapt and accept a ‘Yes, and…’ model, it starts to become much less subjective and much more collaborative,” he continues. “It’s been incredibly freeing, because if the client’s really pushing us to do something we don't think is right… Fantastic! Let's find a way to do what they think is right and what we think is right! Let's try three or four things in between, too! Then it's math. We get lots of smart people together and pick the bits that are working so next time we start with the bits that worked.”

He adds, “It's really trying to find the most lo-fi ways to get ‘at bats’ at doing that.”

This centring of collaboration and kindness has become a pillar of Matt’s leadership style at The Sasha Group, whose heart-shaped logo and name that pays homage to Gary Vaynerchuk’s father reflects the familial, supportive environment that Matt is aiming to cultivate.

“The first thing I said to everybody is, ‘It's going to be stressful sometimes, but the one thing you can never do is not be kind to each other’... If we just put some of the care and attention that we put into every word we use in our work for clients, into our interactions with each other, you’ll have a lot of happy people who feel supported.”

Not only that, but he also wants his team to be able to turn up to work each day, work hard for each other, but importantly, have fun while doing so.

“I actually think one of the perks of this industry is the people I get to physically bump into in the hallway every day,” he says. “I recently ran into someone who had a very serious opinion on which Hold Steady album is the best and why – that, to me, is interesting!

“[These] people are culturally connected and doing interesting things, and have interesting hobbies. If you get paid to be around that, you should derive some joy from it – and that’s impacted my management philosophy.”