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Building Challenger Brands in the Pandemic with 5&Vine’s Rahul Raj

jean pierre fumey



Rahul Raj 5&Vine

Rahul Raj of 5&Vine tells us about helping ambitious founders build, launch and grow meaningful businesses that disrupt categories and better society.

First of all, how are you and your family doing in these COVID-19 times?

Rahul Raj: We are fortunate, grateful, and doing well physically. That said, we are challenged by the state of the world. COVID has affirmed how interconnected we all are, alongside the divisive systems and structures hindering the progress and health of people of color, women, and other marginalized groups. The past year has been a tough but enlightening experience for our family. We’re always pushing ourselves to learn more and determine how best to mobilize our talents and energy to be part of the change we want to see.

Tell us about you, your career, how you founded 5&Vine.

Rahul Raj: I help Challenger Brands win.

I started 5&Vine to help ambitious founders build, launch and grow meaningful businesses that disrupt categories and better society. To date, our impact has helped our partners close over $1B in follow-on financing with two going public, and we’ve worked with some of the most exciting, game-changing brands in the world.

5&Vine was born from my time as CMO at ecobee, where I helped transform the brand from relative obscurity into the #2 thermostat brand in North America with a 30% share and developed a playbook on how Challengers could take down industry incumbents.

Prior to ecobee, I ran an incubator for Walmart in San Francisco. After seeing an opportunity to extract more value out of products that already existed, I built a refurbishing infrastructure that turned costly customer returns into a multi-billion dollar revenue stream. For these efforts, I was honored with Walmart’s Innovation Champion Award, a fellowship with the Aspen Institute, and by the GOOD magazine as 1 of 100 people pushing the world forward.

My commitment to bettering the world started when I was young. At the age of 17, I founded and developed Meal Exchange to build healthy, just, and environmentally sustainable food systems across Canada. To date, students have raised over $2m in food donations in over 100 communities, and our work has been recognized by TIME magazine as “revolutionary.”

Today, alongside my work at 5&Vine, I’m actively engaged in inspiring and empowering others to make their own positive impact. As well as being on the Design Team of the Aspen First Movers fellowship, I mentor entrepreneurs at First Round Capital, Tech Stars, American Marketing Association, University of Toronto’s Venture Mentoring, and Presidio Graduate School, and delivered a TEDx talk on the power of Challenger Thinking.

I know what a brand needs to take on Goliath and love helping them both identify it and put it into action. 

How does 5&Vine innovate?

Rahul Raj: We often engage with startups as their Fractional CMO, helping them uncover and resolve barriers to growth. As each startup is unique, the solutions either require customization if not creation from scratch. This is how our incubation process begins. Where one week might see us working with a hijab brand on a bold campaign to fight prejudice, the next might see us pivoting social media strategies for an organic food delivery service. As we begin to see the replicability and efficacy across our portfolio of clients, we productize these ideas, and so goes the cycle. 

How does the coronavirus pandemic affect your business finances?

Rahul Raj: There have been industries that have thrived during the pandemic – namely those focused on food, telemedicine, and fintech. We’ve doubled down on serving clients in those areas, which has enabled our finances to rebound and surpass pre-pandemic levels.  

Did you have to make difficult choices regarding human resources, and what are the lessons learned?

Rahul Raj: Sadly, yes. At the start of the pandemic, our longest-standing and biggest client died suddenly. We lost a friend and trusted ally. Working on his business enabled the expansion of our service offering beyond marketing strategy to content, social, creative, customer acquisition, and public relations. By contrast, his tragic passing had severe financial and human consequences. We were left with a notable deficit and let go of three team members dedicated to their work. This was the most difficult situation we’ve faced and resulted in a number of important lessons.

  1. Diversify risk. Overdependence on few clients has severe consequences when they leave. 
  2. Treat yourself as a client. If you can do it for others, you can do it for yourself.
  3. Treat your team with humanity even as they exit. Support with severance beyond the requirements, and help connect them with opportunities from your network. 
  4. Say ‘yes,’ and sometimes say ‘yes with conditions.’ Find a way to make new work, work. 

How did your customer relationship management evolve? Do you use any specific tools to be efficient?

Rahul Raj: Trust is key to winning business, and chemistry is needed to realize the impact. Both of these are materially easier to establish in person. When the pandemic hit, we had to evolve the way we approached both. We leveraged Google Meets to give clients a literal window into our world, with kids often traveling through the scenes. Instead of hiding it or being embarrassed, it was another point of authenticity that co-exists with our commitment, intellect, and experience. 

We also embraced the premise of a first date, aiming to solve a client problem in real-time, as a means to better identify the potential promise of the engagement. We followed that up with 1-3 days’ worth of paid work, based on the honor system (not a contract) to ensure we both had lived experience and could opt into a formal contract. Both of these were instrumental in helping us evolve our relationships with clients. 

Did you benefit from any government grants, and did that help keep your business afloat?

Rahul Raj: We benefited from the CEWS and the CEBA, both of which supported our turnaround.

Your final thoughts?

Rahul Raj: We have a strong and exciting plan for 2021. As we evolve into a Venture Studio, investing money alongside our services into startups, we believe we can deliver massive social and economic impact. This co-exists with our fee-for-service Fractional CMO and startup marketing agency.

We take our social commitment seriously and will ramp up our pro bono and mentoring to ensure the brands we choose to work with are delivering on their promises to better the long-term health of people and the planet. We align ourselves with clients and people we genuinely believe in. 

While we have a lot to learn, we also have a great deal of insight to share. We’re investing heavily in content to share those insights and better the startup community. You can see the start of that over on our blog

Your website? 

Jean-Pierre is a polyglot communication specialist, freelance journalist, and writer for with over two decades of experience in media and public relations. He creates engaging content, manages communication campaigns, and attends conferences to stay up-to-date with the latest trends. He brings his wealth of experience and expertise to provide insightful analysis and engaging content for's audience.

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