Rob Woodbyrne of Regrow: “Surround yourself with a talented team”

Understand the Market Cap for your offerings marketUnderstand the pains of the marketUnderstand the competitive landscapeSurround yourself with a talented team. No slackersKnow your differentiators and be passionate about educating Startups have such a glamorous reputation. Companies like Facebook, Instagram, YouTube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles. […]

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  • Understand the Market Cap for your offerings market

  • Understand the pains of the market

  • Understand the competitive landscape

  • Surround yourself with a talented team. No slackers

  • Know your differentiators and be passionate about educating

  • Startups have such a glamorous reputation. Companies like Facebook, Instagram, YouTube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

    Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

    In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

    I had the pleasure of interviewing Rob Woodbyrne, CEO of Regrow.

    Rob Woodbyrne is the Chief Executive Officer at Regrow, based in San Diego, California. Rob is an experienced leader with a demonstrated history of bringing innovative, disruptive technology to market. As a professional with a proven track record in cloud solutions, SaaS, PaaS, Enterprise Software, Partner Management, and Enterprise Architecture, Rob & the Regrow team are focused on helping cannabis businesses manage their supply chain to grow more cannabis!

    Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    I started in sales during the boom, then moved into Disaster Recovery, which let me get very familiar with how businesses run. I later moved on to ServiceNow, until we took it public. I then founded a Hospital Asset Management startup called Connectiv, which we sold to Accruent, and it still remains the de facto standard in Healthcare today. From there, we decided to follow a path to something that was closer to our hearts, as well as an amazing business opportunity, in the cannabis industry!

    What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

    The ‘Aha Moment’ is usually determined far into the Stealth Mode launch process, and it was no different with Regrow. Once we determined what industry problems existed, and how we could solve them, the next step was to determine whether a market existed and if we could lead or be disruptive.

    Our ‘Aha Moment’ was when we did the research, determined that there was plenty of opportunity, and our return on investment made sense for 80% of that market. We knew we could do something meaningful in a space that would support a growing business.

    Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

    My old bosses — the good and the bad. I learned something from them all. The ones that were the best, I honestly still work with. Craig Harper was my boss at ServiceNow. Chris and I asked him to join our Board of Directors, as his leadership continues to make us better.

    What do you think makes your company stand out? Can you share a story?

    Regrow is the only enterprise supply chain management platform built for the cannabis industry that helps operators increase their yields, align to market demand and stay compliant by managing the chain of custody from raw materials to finished packaged goods. We’ve been solving these complex problems over the last two decades for the largest organizations on the planet, and now we are excited to bring this skill set and experience to the cannabis industry.

    How have you used your success to bring goodness to the world?

    I promote cannabis. That is really good, medically, environmentally, and socially.

    You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

    1. Team Building — The tremendous group of talented leaders and professionals that work with us.
    2. Tenacious — As Yoda says, ‘Do or do not. There is no try.’
    3. Supportive — In order to get talented people to join you on a journey, you need to make it engaging and interesting. As a founder, you are here to support their efforts, not the other way around. Always stay focused on your workforce’s experience. If they are not motivated or focused, they are flight risks. Talent is the most important thing in startups.

    Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

    It is tough because you are constantly adjusting. The final outcomes are determined by your ability to adapt to the current situation. Everything is a learning experience, I can’t think of an instance where I regret making a decision. Of course, many decisions have reversed course on a prior decision. When we realize we’ve made a wrong decision, it is important to identify it and come up with a strategic new direction and we operate under that new direction going forward. You can’t be fearful of making mistakes, otherwise you’re not giving yourself the opportunity to innovate.

    Can you tell us a story about the hard times that you faced when you first started your journey?

    Startups are naturally a challenging endeavor. I can count my unsuccessful startups as hard times, but without experiencing those challenges I wouldn’t be where I am today.

    Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

    When you start a venture there are other people that invest time and money into your vision. Being a vigilant stewart of those investments drives me.

    Surrounding yourself with talent and having a culture of transparency helps ensure thoughtful consideration of available options are being weighed. So, always move forward. If something doesn’t work, acknowledge it, learn from it, and determine a new path forward, and follow it. Don’t be afraid of making mistakes, be afraid of not recognizing them as such, and responding accordingly.

    The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

    It is about tenacity. You can run into walls, have your path blocked, but you have to regroup and go around those challenges. Startups are about how quickly you can adjust, and how successful your adjustments are. Business is more like life, not a seasonal competition. Temper success as a ‘we are doing it’, not as ‘we did it.’ Success provides opportunity to innovate, take risk, and continue working with the people we enjoy working with. Don’t view it as an event to take selfies at.

    Let’s imagine that a young founder comes to you and asks for your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

    It is an evolution. You always bootstrap at the beginning. Then you have to determine your road to profitability. The more success, especially revenue, you can get, prior to those VC conversations, the better the outcome will be. VCs are risk managers. They want your company to succeed, however, their patience is short, so the better you can articulate or even prove your path to profitability, the better the relationship will be.

    Ok super. Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need to Create A Highly Successful Startup”? If you can, please share a story or an example for each.

    Understanding your market before you launch is the overarching theme for these needs:

    1. Understand the Market Cap for your offerings market
    2. Understand the pains of the market
    3. Understand the competitive landscape
    4. Surround yourself with a talented team. No slackers
    5. Know your differentiators and be passionate about educating

    What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

    Not surrounding themselves with a good team of advisors and early employees. Not having a defined vision. Underestimating how difficult it is to start a business and accepting the risks that are involved with that. The successful founders I know are individuals who have already passed the part in their careers where they feel the need to manage people. It’s important to realize that you are a facilitator for the people that embark on this endeavor with you.

    Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

    I think this has a lot to do with personality type, then experience helps. Many founders are types of people that don’t sleep a lot, to begin with. Passion is something that you need, especially in a startup environment. The talented group of people that will join a startup love the risks, rewards, and freedoms that come with the startup culture, but they truly need that motivator, who can help guide the team through the high surf.

    Whatever it is that keeps you passionate is what you need to harness. Be self-aware and surround yourself with people that are honest with you.

    You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

    Learn about cannabis and your body. Every one of us has an endocannabinoid system inside our bodies. That means humans have had a symbiotic relationship with cannabis long before we became buddies with dogs, long before monotheism (Judaism, Christianity, and Islam) developed in the fertile crescent and demonized it as a pagan ritual.

    The natural things that cannabinoids can influence are anxiety, appetite, stress, pain, sleep, and nausea, just to name a few. Cannabis is medically proven to be non-addictive and non-lethal, at any quantity.

    Instead of using alcohol and opioids to manage those ailments, which have many negative side effects, research and understand how cannabis can naturally help your body address the issues through your endocannabinoid system.

    We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

    Elon Musk. I have this idea about growing psilocybin on Mars.

    How can our readers further follow your work online?

    Follow us at, you can find our blog and news sections there. Hit me up on LinkedIn too.

    This was very meaningful, thank you so much. We wish you only continued success on your great work!

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