'When You're Doing Good Work, It Travels': Herb Founder and CEO Matt Gray Shares What He Used To Scale The Cannabis Company

Entrepreneurs are often too obsessed with the outcome.

That’s not necessarily the right thing to do, explains Herb founder and CEO Matt Gray whose mission is to pay it forward and inspire 10 million entrepreneurs to live their dreams.

Amidst a slowing economy, Gray urged entrepreneurs to recognize their venture is a marathon and, in order to speed up, they should consider “slowing down and taking better care of themselves and those around them.”

Why’s that? Read on for Gray’s journey in building and selling businesses, perspectives and tips for success.

Find A Problem And Solve It: The Sharon, Ontario native’s foray into entrepreneurship started at 20 years old.

While managing 28 retail locations for Kraft Heinz Co KHC, on the side with three friends, Gray built Bitmaker Labs, a school for technologists.

“It was a place for software engineers to train for jobs at technology companies like Shopify Inc SHOP, Meta Platforms Inc META, and IBM IBM.”

After training nearly 3,000 technologists, and selling it to General Assembly, Gray pivoted.

This time, the problem was that there “existed no platform for consumers and brands to connect over curated and trustworthy content,” he explained on getting the word out about the treatment that saved his friends' lives from feelings of suicide and depression.

“There wasn’t an experience akin to the kind you’d expect outside of weed.”

The Google Of Weed: Over the course of nearly a decade, Gray and a small team of up to 50 grew Herb to a community of 14 million loyal fans, all raving for what is 31,000 published pieces of cannabis-focused content.

Gray practices what he preaches. For those years Herb has operated, it has only published, consistently, 12 pieces of content a day on culture, education, “and everything in between.”

Now, some may wonder how this endeavor makes money? That’s simple, Gray says: “When you’re doing good work, it travels.”

In observing readers’ responses, Herb has constructed Herb Analytics, its version of Google Analytics, which gives people in cannabis a “full picture of the entire funnel” to find consumers.

“It’s the Google of Weed,” he said about Herb, with Gray having looked to the likes of Shopify CEO Tobi Lütke, NFL Hall of Famer Joe Montana’s Liquid 2 Ventures, and Complex founder and CEO Rich Antoniello, among others, to ideate, fund and build technology that helps with reach audiences, beyond the traditional “combination of email, programmatic advertisements, as well as SEO.”

“We’re looking at, for instance, those small dispensaries in Denver that are seeking to get on the map, all the way to Cresco Labs Inc CRLBF and Curaleaf Holdings Inc CURLF who are entering new markets and a strategy for domination.”

Building Engaged Audiences: Though “trusting the data” seems like an un-authentic way of describing the key ingredient in penetrating larger audiences, it’s really that simple.

“It helps us get better insight into the unique tastes, preferences, and interests people may have, as well as where to drill down. Otherwise, we’re shooting darts as many others do.”

The way to gather reliable and impactful data is to establish a clear and consistent format that is altered, progressively, through time.

“Mistakes and successes allow us to adapt what we’re doing and progress much farther than most,” Gray said. “It’s the brands who aren’t consistent and give up on strategies after months. We’ve been doing this consistently with 12 pieces of content a day for nearly nine years, now.”

Cannabis Is Having A Moment: Cannabis is where hip-hop and sneaker culture were in the '90s, Gray puts forth.

“I think cannabis is having that kind of moment where it’s bridging the gap to like mainstream adoption and the kind of cultural zeitgeist. Herb is ushering it there in our own way.”

Gray did say that regulatory evolution, as well as the conservatism of social media platforms toward Schedule 1 drugs such as cannabis, have cut into the good work Herb is doing, which leads to “sleepless nights.”

For that reason, just like when building any product that has an attached community, you have to “lean into raving fans and growing profitable business” lines that were “not necessarily sexy.”

“We have been the tortoise in the game and we don’t chase fads. We’re focused on building really trustworthy brands that more people will turn to.”

How Do You Do It Over And Over: The key is to take care of your health.

“The more you’re at your peak performance, then, the better able you are to take care of your business, family and the relationships that surround you.”

Gray was too obsessed with outcomes early on in his career. He explained they were a detractor from the growth of his businesses. Treating himself as an athlete, he realized that as businesses were built over a long time horizon, it unlocked more opportunities.

“In order to be the best in my area, I’ve looked to people like Greg Isenberg, Rich Antoniello, Jesse Itzler and a bunch of others. I built a personal board of advisors, and that helped with curating a business in which workers are a really good fit.”

Additionally, great artists look toward other great artists for ideas.

“When I’m looking at the infrastructure we’re building, I’m modeling how Alphabet Inc GOOGL GOOG, Zendesk Inc ZEN, and Apple Inc AAPL have built things, as well as how they’re structured.”

Focus Points In The 2020s: “Having a great team of operators that know what they need to do,” removed the burden from Gray’s shoulders, leaving him more time to hone the “brand, culture, strategy and content.”

“We’re going to survive through formidability and anti-fragility.”

The End Game: Beyond building “the most beloved cannabis brand in the world for a global community of nearly 100 million,” Gray is seeking to surround himself with people indicative of the future self he’s trying to build.

“It’s important for young entrepreneurs to do an inventory check,” he said, pointing people to his newest initiative, The Soulful Entrepreneur, a series of courses, community, and a SaaS toolkit for aspiring entrepreneurs to build shortcuts for content, copywriting and community growth.

“I’m democratizing my knowledge to help other entrepreneurs do the same.”