Dennis O’Malley

Getting issues on the table quickly without emotion helps foster trust and enables quicker resolution to problem-solving.


Dennis O’Malley is President of Caliva, the largest vertically integrated cannabis company in California. Driven by a passion for enabling people to choose their own health and wellness options, Dennis has launched Caliva into a rapid growth phase, racing to become the #1 trusted brand in cannabis.

Dennis has over a 20 year track record of leadership roles in fast growing companies in emerging markets as well as successfully raising capital from institutional investors and in addition holds multiple technology patents.

Most recently Dennis co-founded and lead a venture backed software company that enabled brands like Red Bull, Nike, Adidas, The North Face, and Reebok to scale their revenue through ambassador marketing programs. The company was sold in 2016 for a 10x revenue multiple.

What does your typical day look like and how do you make it productive?

My job is to empower people, make decisions, solve problems, and remove obstacles. My schedule generally revolves around work around people, projects, and customers. Productivity is always top of mind, but the leading factor of productivity for me is being very straightforward – if you are able to hit the hardest issues in plain language with your team or customers, I generally find that I am able to take on more decisions quicker.

How do you bring ideas to life?

I can’t bring an idea to life unless someone else gets as excited about it as I do. Unless that happens it will never get executed (at least not to it’s potential). A goal is to provide the work and thinking behind ideas and what the end state goal is. Everything in the middle has to be trusted to your team.

What’s one trend that excites you?

The new consumer in our industry (cannabis). This new consumer is making a considered purchase ($150+ per transaction) and is demanding a trusted product in a compelling consumer experience. This groundswell of consumers who are empowered for the first time to self-prescribe natural health and wellness is starting a movement.

What is one habit of yours that makes you more productive?

I don’t have issues with conflict. In my experience, most colleagues appreciate straight talk – I know I do. Getting issues on the table quickly without emotion helps foster trust and enables quicker resolution to problem-solving.

What advice would you give your younger self?

Tons. Mostly work harder to make things clearer and simple. It does take a lot of work to make things simple and if you are not able to articulate a concept in plain language it probably isn’t a great idea.

Tell us something that’s true that almost nobody agrees with you on.

Picking up the phone and talking with someone is more effective than email or text or Slack or Google Docs or Asana.

What is the one thing you do over and over and recommend everyone else do?

Keep 1on1s. Having a 1on1 meeting cadence is critical to a flow of info from a distributed team. My week doesn’t start until my 1on1s are done.

What is one strategy that has helped you grow your business?

Hustle trumps scale everytime. Plan to ensure your initial products and services are very well received and you shower those early customers with lots of love. Once you are able to get a number of consistent proof points, then think about scaling.

What is one failure you had, and how did you overcome it?

Biggest failure to date was relinquishing control over our companies sales/marketing post-acquisition. I knew in my gut our team would have been able to execute better than the plan that I had agreed to. I wish I had a Mulligan on that one.

What is one business idea that you’re willing to give away to our readers?

Still think on-demand fulfillment of physical products / samples to ambassadors is an area that can grow significantly.

Key learnings:

  • Work to make things simple. Trusted relationships enable you to get straight to the point. Helps get stuff done quicker.
  • Team expects you to think big and show them the goal posts. Trying to execute against your own ideas always fails. Think bigger and think clearer.
  • I’ll take hustle and conversations vs. scale and project plans every time for fast growing businesses in new markets. Having a comfort level with fluidity here is critical.


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