ABOUT ROBIN WOOD SAILER:
Her career began in journalism, with roles at CBS News, Bloomberg News, and The Wall Street Journal | Barron’s Group, where she produced award-winning content across digital, broadcast, audio, mixed reality, and nearly 100 major live events.
Today, Robin advises founders, investors, and executives on how to tell their stories, build partnerships, and grow through strategic events. Le Labs’ portfolio spans Fortune 500s, nonprofits, startups, and visionary investors. She also serves on the board of the New York Financial Writers Association.
Q&A WITH ROBIN WOOD SAILER:
What is your most valuable possession and why?
My most valuable possessions are my children. They yield love and pay huge returns everyday. A mother’s work is never done, but it is a job that gets me out of bed everyday with a full heart.
What are your top 3 life lessons and how have they changed your life for the better (in other words, how have you implemented them to better your life)?
- The most inspiring word is, “No!” Think of all the people who have set out to prove someone wrong who told them that they can’t do something. “No,” is often just the beginning of an incredible underdog story.
- Don’t carry anger. You can spend a lifetime being angry with someone you love, someone at work or a person who cut you off in traffic. There is a wonderful story in Jon Muth’s children’s book Zen Shorts about carrying frustration. I have read it to team members in my one on ones. Do not carry negativity. Put it down and move on – you will sleep better at night.
- It is never too late to follow through with your childhood dreams. I still want to be an artist, a filmmaker and write the great American novel. Last summer I took two writing workshops, a documentary film course and spent some quality time with my paintbrush. Life is a work in progress and so are dreams.
What is the most valuable advice you’ve received and how did it set you up to win?
A couple decades ago I was at the table for my college fair talking to alumni about pursuing a career in the media. John “Bones” Rodriguez – an actor, author and entrepreneur – was also at the table. If someone came up and said, “I want to write a book” or “I want to be a journalist or “I want to be an actor.” He would say, “Why aren’t you doing that already? No one is stopping you!” He told them, he wanted to write a book, so he wrote eight books and self-published them on Amazon. His point was, ask yourself what you want to do and start doing it. There were so many opportunities I didn’t take, because I was waiting for someone else to give me permission to take them. Just start doing the job you want to do – now!
What is the worst advice you’ve received and how did it impact you?
When I was graduating college, they said all the great ideas have already been thought of and that everything our generation would contribute would just be an iteration of what had already been done. That was in 1998. When you think about the innovation in the last two decades, I think about how it is so important to not listen to voices that limit a field of vision.
What is the one mistake you regret in life, and why?
I used to regret that I didn’t get into Brown University. My mother went to Pembroke and as a young girl I had my heart set on Brown. I regretted it, until I met my husband. He went to Brown and we would have been in the same class. I am 100% certain if we met in college we would not be where we are today. Now I still get to go to reunions and march with the class, some people think I was actually in the class. You only go to college for 4 years, but I get to reap the benefits of reunion weekend for the rest of my life.
The most inspiring word is, “No!” Think of all the people who have set out to prove someone wrong who told them that they can’t do something. “No,” is often just the beginning of an incredible underdog story.
When you face a challenge, what’s your method to move past it?
Sometimes when you have a problem and you do nothing, it will resolve itself.
How do you create a work-life balance?
I don’t! My life is totally out of balance, full of kid energy and career energy and it fills me to the brim. I don’t know why we put work-life balance on a pedestal. I would rather watch a juggler than a woman with a book on her head anyday.
What “women” hangups have you been a victim to, that you feel sets women up to fail in their professional career?
I am a venture partner at Helena Capital, a VC that is raising its first fund where the founding general partner is a woman – Sarah Antor. The percentage of global venture capital money that is allocated to female founders is under 2%. There are very few VCs run by women who invest in companies at the Series B growth stage. Helena Capital has had to overcome a lot of the historical biases that have made those number what they are but the fund is now poised to make waves.
Are you affected by the Confidence Gap, where studies show that women require confidence as well as competence to succeed in the workplace environment, whereas their male counterparts don’t?
There is that Frank Sinatra song “That’s Life,” “You’re riding high in April, shot down in May, But I know I’m gonna change that tune, when I’m back on top, back on top in June.” The summer my role was eliminated from a company that I had called my home for 8 ½ years and where I had had both of my children, I felt like I had disappointed my family in such a huge way. My husband and I talked about changing my children’s schools, moving cities and selling our apartment. That summer I barely had time to lick my wounds before one of my old colleagues put me to work building the same business we had just left. We still had momentum with the relationships that we had built and there was some business we could grab and run with.
I didn’t feel like I was winning at work yet, but I stumbled into a new forum to win in. It was an odd age to pick up a sport, but a pickleball group at the local club was just the kind of camaraderie I needed.
Ask yourself what you want to do and start doing it. There were so many opportunities I didn’t take, because I was waiting for someone else to give me permission to take them. Just start doing the job you want to do – now!
By the end of the summer, I somehow became the women’s double champion. It felt like a fluke. My partner was an 8th grade ringer. I never thought I could do it again, especially when I heard my ringer was out of town the next year on the day of the tournament. Somehow, I defended the title the next year with a different partner. I played some of the best pickleball I had ever played in that tournament to keep the title. It is harder to call it a fluke if you win twice. There are many better pickleball players than I, but what closed my confidence gap was not winning once, but winning twice. Maybe a man would have only had to win once. Maybe a man would never have thought it was a fluke the first time. This summer I am going for three-time women’s double champion. Wish me luck.
Oh, and that business I started with my partner – Le Labs – it helped stabilize what felt like a financial freefall and has led me on one of the most professionally rewarding chapters of my life.
What does equality mean to you and is it important?
I am working with the head of innovation and transformation at the United Nations Population Fund around ecosystem support where the gap of funding in maternal health is as big as it ever has been. The agency is looking to innovative solutions to establish partnerships that can step up to bridge that gap. The UNFPA supports maternal help around the world to give women a better chance of surviving childbirth and provide the kind of maternal care that will give children – male or female – the best shot at a healthy life. Through the WomenX Collective the UNFPA is looking to fund innovation available today to help scale the increasingly limited resources to help make that possible. We need more philanthropically minded people to come to the table there.
When I think about how families are designed for equality, I look at the little boy and little girl I am raising. They both play with L.O.L. Dolls, spend all afternoon building with legos and race matchbox cars. He is less interested in ‘skincare.’ When they race each other down the sidewalk, they are neck in neck. My daughter is two years older, so for a while she always took the lead. My son has just about caught up. One day he overheard some grown-ups talking about sports and he was shocked by what he heard, “What do you mean men are faster than women?” That had never even occurred to him. I want them both to live in a world where everything is possible and there are no limits.
In your experience, what types of male allyship do you feel women need to foster at home and at work, to encourage an equitable ecosystem?
Marriage and parenting are a lot like rock climbing. One person needs to spot, while the other one climbs. Sometimes life calls you both to spot or both to climb, at the same time. It is important to be invested in the success of your partner and to have in-laws you can count on. People need to talk more about in-law allyship!
The pandemic was a great equalizer. Everyone was home with children climbing on their heads during zoom calls. Equal parental leave helps level the playing field when everyone has to hand over a book of business during their leave. It also means that everyone is invested in continuity upon return, because it could happen to them. Maternity and paternity leaves of absence are not vacations, they are an important time for all parents to bond with their children.
What would you tell your 18-year-old self, looking back over your life’s experiences?
I would encourage my 18 year old self to be more entrepreneurial earlier. Some of my friends from that era of my life are my business partners today. I am a venture partner at Helena Capital. The founding General Partner Sarah Antor was my roommate in boarding school. It just took us 20 years for our work to bring us together in business. Imagine what we could have accomplished by now if we had started earlier!
Raj Bhakta who founded WhistlePig Whiskey was my flatmate when I studied abroad in Vienna. I invested in and advised WhistlePig until we both exited in 2019 and now I am advising him in his next chapter at Bhakta Spirits. He doesn’t always take my advice, but I give it!
What advice would you give to women to help them step into their power?
Surround yourself with people who believe you are capable of anything. Become an expert in something, find your voice and don’t be afraid to use it!
Can you share one resource (book, course, mastermind/masterclass, etc.) that you feel all women need to have?
I have had a lifelong love of the theater and have been known to hold friends throughout my life hostage in my audience while singing Cabaret songs. My parents and grandparents turned me on to the thrill of old standards. Like so many people I had broadway aspirations, but without broadway level talent. Sometimes I would even wish that I lived in a musical. In New York, there is this wonderful musical improv course at Magnet Theater where you learn the rules of improv but in the context of a musical. In the first five minutes of class you are singing and dancing with ten strangers who share your passion. It satisfies those broadway aspirations, but the class also makes you fearless in other contexts – on stage, in the workplace and in a boardroom.
Surround yourself with people who believe you are capable of anything. Become an expert in something, find your voice and don’t be afraid to use it!
What mantra do you live by and how has it impacted your life?
Find a passion that quiets the mind and that you can do alone. When I ski the same run over and over it feels like a mantra. “I turn here, there is the bump, I need to slow down there to catch the curve right, beware the root, here comes the ice, ah yes, that powder feels good, if I catch some speed here I might catch some air as I feed into the next run.” Skiing forces you to be present and to live in the moment.
Which therapies/modalities have helped to shape your healing and empowerment journey that you think would be helpful for other women?
We spend a lot of time in Maine. You can’t buy Maine in a bottle, but it is all the therapy I need. Nature’s beauty is bountiful the moment you step out the door. I love wandering the forest, looking under logs, marveling at fungus and paddling in the water. The hum of the insects, soft calls of an owl or the surprise theater of an Osprey making off with a fish in its mouth are my meditation. It works for children too. Take them fishing for the afternoon and they have forgotten all about screen time.
WHAT'S NEW WITH ROBIN WOOD SAILER:
Today, Robin channels that magic into purpose-driven work: uniting people to advance maternal health with the United Nations Population Fund, advising changemakers as a venture partner at Helena Capital, and crafting extraordinary moments through her experience agency, Le Labs. Her clients span industries and continents, leaders in business, government, and academia who turn to her when the stakes (and the stories) matter most.
