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Meet the Founder

After spending 7+ years working as a top-level personal assistant and Chief of Staff for A-List celebrities, CEO’s and high-net-worth individuals! Valerie discovered that she could bring the same level of excellent service to individuals, entrepreneurs, and small business owners. This is the foundation that ChatterBoss is built on. ChatterBoss is a dedicated and on-demand virtual executive assistant company. 
Everyone is remote,15 assistants across the US, and 2 assistants in South Africa. 
Bootstrapped. Chatterboss originally bootstrapped because they needed to get a proof of concept before raising any rounds of funding, but as time went on, the business took off, and they realized they’re able to continue running it without relinquishing any control of the company.
May 14

3 min read

"When You Find People Whose Soul Is Easy To Read Without Too Many Words, You Have To Hang On To Them."

Every week we send the same list of questions to a different founder from companies of all sizes. Each week we get new answers, insights, perspectives, and tips on how we all can shine a bit brighter.

Valerie Donohue

CEO & Founder at Chatterboss

Valerie has been now traveling and remote managing her company for 5 months. She also has a podcast called Entrepreneurial Minds, for which she has been interviewing entrepreneurs around the world during her travels.

Meet the Founder

After spending 7+ years working as a top-level personal assistant and Chief of Staff for A-List celebrities, CEO’s and high-net-worth individuals! Valerie discovered that she could bring the same level of excellent service to individuals, entrepreneurs, and small business owners. This is the foundation that ChatterBoss is built on. ChatterBoss is a dedicated and on-demand virtual executive assistant company. 
Everyone is remote,15 assistants across the US, and 2 assistants in South Africa. 
Bootstrapped. Chatterboss originally bootstrapped because they needed to get a proof of concept before raising any rounds of funding, but as time went on, the business took off, and they realized they’re able to continue running it without relinquishing any control of the company.

1. What is a daily habit you love doing?

To be honest, I find a lot of value in daily routines but also my personality is such that I get bored of routine easily. So I'll usually develop a routine that I keep for a few months and then switch it up. One of my favorites has been "The Five Minute Journal". It asks you to answer the same 5 questions in the morning and night each day, and it's amazing how much you can learn about yourself by doing it consistently.

2. What piece of advice would you give yourself when you started? What advice would you ignore?

To trust my intuition. A lot of the times entrepreneurs come up with ideas in their field of expertise because they have some nice insight. It's natural to ask for advice from mentors, and it's very helpful – but at the end of the day, you have to run it through your own filter because you'll get a lot of conflicting advice especially in the beginning.

3. What piece of content (book/podcast/Ted Talk) is your favorite or has influenced your life?

I love the self-help/psychology field and consume it all, regardless whether it's relevant to my life at the moment. Sheryl Sandberg's Option B is a powerful dive into dealing with grief and life after a significant loss.

Option B, Sheryl Sandberg

See Chen Levanon’s column who was empowered by another one of Sheryl Sandberg’s book, Lean In.

4. What is the most valuable investment (time, money or energy etc.) that you’ve ever made?

Therapy! I think it's such a superpower being able to learn about your wiring, responses, etc.. and having the control of how your brain works vs. being run by automatic responses in certain situations.

5. Is there a quote, mantra or message you live your life by and that you resonate with? It can be someone else's as well.

I believe that there are people you meet that "speak your language". They 'get you' without having too much explanation, and those are the people who should be in your inner circle. Of course, communication is very important and you have to voice your needs, but when you find people whose soul is easy to read and vice versa without too many words, you have to hang on to them. I find these kinds of connections one of the greatest gifts in life.

6. What helps you stay motivated on good and hard days?

Perhaps like many entrepreneurs, I actually find it easier to stay motivated during hard days because there's more of a constraint. I struggle more with motivation when things are good. I read somewhere that if this is how you work, you have to put constraints on your time so that it becomes limited and thus pushing you to get more done.

7. What are you passionate about other than managing your own company? 

I started running a year ago. It's been incredible to see how far I can push my body and mind. Running also connected me to the changing of the seasons, which is so cool. I've spent much more time in 2019 outdoors than I did in a very long time because of the running, and for that I'm grateful.

Valerie finishing the TCS New York City marathon.

8. What have you recently thrown away or released from your life that made a positive impact and why?

The last 5 months have been the first time I have traveled on my own for an extended amount of time. This has shown me how little I actually need in my day to day life. At the end of the day, belongings of any kind take up mental overhead, and being down to the basics has been really liberating. Unintentionally it seems I’ve also released jeans from my life, but I hope to get those back (and still fit into them) at some point.

9. Share a failure you have experienced and what you learned from it.

I spent a large part of my career fighting against my 'natural modes of operation' – my own personality traits. Once I learned my personality better (a very useful tool is the Kolbe test) and started organizing my work and personal life around my strengths, things became much easier.

10. If you could have anyone in the world answer these questions who would it be and why?

Esther Perel. Esther is changing the way we think about relationships and the conversations we are having. I find it very inspiring when someone is able to come in and say that things aren’t necessarily as we know them and get people thinking and talking. 

To read more about Esther Perel, click here.

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