In Conversation with Ali O’Grady of Thoughtful Human

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Describe Thoughtful Human in a few words?

Honest. Empathetic. Quirky. Fun.

What made you take the leap to start your own business?

For me, taking the leap resulted from an “aha” moment in my professional life and a series of unfortunate events in my personal life.

I was working for a small urban farming startup where I had the opportunity to watch and participate in their rapid growth. We were all so young and green, so I was really surprised to see how many industry leaders were looking to our small brand for innovation and marketing insight. It was really empowering and liberating to learn that, to an extent, we’re all just making it up. Of course there is much to be learned from industry vets, but with things moving and changing so quickly, I realized you don’t have to have the stereotypical resume or X number of years experience to start something and shake up an industry. I thought, if everyone’s just making it up, why can’t I make something up to address the issues going on in my own world?

A few years prior, I had lost my favorite human after a ten year battle with colorectal cancer. Over the years, I noticed glaring communications issues on all sides — everything from me struggling to talk honestly with my dad about his feelings and fears before he passed, to everyone else struggling to talk with me and my family about grief, depression, addiction, and other issues we were facing after he passed. I started talking with more and more people about this phenomenon — our cultural inability to broach difficult subjects and show up over time. The more people I talked to, the more common I realized this was, and just how many people were left feeling isolated and alone in their most trying moments. I wanted to change that.

Empowered professionally and inspired by this response from my community, I decided it was time to take the leap!

What was your background prior to starting your own business?

I was always passionate about sustainability and writing, but ended up fascinated by and majoring in psychology at UC Santa Cruz. After college, I held positions in marketing, sales, and project management across various industries (with lots of serving positions along the way!). Prior to launching Thoughtful Human in 2017, I was the Marketing Manager at an urban farming startup.

Did you always know you wanted to be an entrepreneur?

I was always interested in entrepreneurship, but was weighing other pursuits like journalism, nonprofit/community organizing, clinical therapy, etc. I always liked the idea of working for myself and doing something different but, at the time, I had a limited idea of what entrepreneurship meant. I thought more about creating a boutique coffee shop or bookstore, not a consumer brand. I certainly had no idea I’d land here, but always knew I wanted to do something impactful and try to avoid the traditional rate race.

Take us back to when you first launched your business, what was your marketing strategy to get the word out and did it go as planned?

I intended to sell card bundles exclusively on my website in specific categories, and market them exclusively through social channels. And no, it absolutely did not go according to plan! It was super expensive, and quickly evident that my customer’s needed more flexibility in customizing their bundles. I saw interest from brick and mortar retailers early on, and quickly shifted my strategy beyond social advertising to leveraging our in-store distribution and developing meaningful partnerships with companies/orgs that shared our target audience.

We always learn the most from our mistakes, share a time with us that you made a mistake or had a challenging time in business and what you learned from it?

Last year I did my largest program to date with a retail partner that swiftly went bankrupt and left us in a very challenging financial situation. At the time, it felt very personal and truly insurmountable. However, the months that followed proved it was neither of those things. 

I learned to always consider your absolute worst case scenario because it can become your reality (especially now in COVID), and to thoroughly vet new partners and opportunities, even if you feel like the small fry in the situation.

I learned to process, cry, and leverage my wins to move forward. In spite of this blow, I was able to take the success we showed with the program and use it to open up bigger opportunities.

What is the accomplishment you are the most proud of to date?

Caregiving for my father — easily the most challenging thing I’ve ever had to do.

Giving my TEDx talk is also up there…I have pretty debilitating performance anxiety so it was not something I ever intended to do, but I was invited to speak and felt like it was something I needed to face. The final product is far from perfect, but there are few things I have had to work as hard at, and few moments where I have been as vulnerable. I’m proud of that.

When hiring for your team, what is your go-to interview question? Please share any hiring tips you can share from your experience?

What’s an experience that has shaped who you are today? The right skillset is key, but understanding someone’s character and values is equally important in a business like mine.

How has your business or industry been impacted by the COVID-19 pandemic?

All of our physical retailers closed in March. This caused large order cancellations, returns, significant payment delays, USPS shipping delays, and beyond. It has certainly been challenging to navigate and kicked many of our original 2020 plans to the curb, but in terms of our products and mission — to help people connect and communicate through adversity — our products have never been more relevant or resonated as deeply.

What’s next for your business? What can we expect to see over the next few years?

We will be growing in some exciting ways in 2021 — of course pending safety and COVID measures, you can expect to see our retail footprint expand quite a bit with new and existing partners. We will also be introducing products in some new and unexpected content areas…stay tuned!

What is the biggest lesson you have learned in 2020?

Be flexible, stay aggressive, focus on your “why,” and remember: you are entitled to nothing. Not time, health, success, money… whatever you have now is a gift and may be fleeting — treat it as such.

What do you know now that you wish you knew when you were first starting your business?

Everything is negotiable. Starting out, I didn’t have the confidence to push back on certain things with people and partners who I deemed to be bigger, more important, or more knowledgeable than me. But your time and money matter regardless of your size and, many times, they need you more than you need them so you have more leverage than you think — always push back, always negotiate.

How have you managed to stay grounded this year?

I have certainly gone through some phases throughout COVID  but, in general, things like exercise, being around kids, animals, the ocean — anything that gets me out of my own head and thinking about others.

Surfing has been super helpful (and humbling) for me in many anxious moments this year — no choice but to be present and try to stay afloat. 🙂

Do you believe in work/life balance? What are some of your best tips?

Absolutely! It’s definitely a bit different for entrepreneurs, but I have really come to accept the ebbs and flows of my creativity and motivation and don’t work by a clock anymore.

When they’re lacking, I don’t try to force it. I just trust that both will return, and I will be more productive and do higher quality work when they do. I also know now that if I’m not operating at 100 it’s usually for a pretty good reason, so I allow myself to process and sort through whatever is hanging me up.

What’s something our audience would be surprised to learn about you?

That despite all efforts, I am an out of control night owl with an out of control sweet tooth.

What are your top 3 tips to stay productive each day?

Good sleep, calendaring/blocking time for all to do items (not just meetings), and creating a personal reward system.

What does being an Entreprenista mean to you?

Being an Entreprenista means pushing the boundaries and being fearless in pursuit of a greater purpose — working with grit, and leading with empathy, kindness, and conviction.

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