MEET SASHA ~
A Matchmaker Who Spreads Love Like Butter!
I had the pleasure of chatting with the lovely Sasha Silberberg as the first interview in a series I’m compiling of chats with badass women (and non-binary folks) who’ve braved pioneering lives off the beaten path. I was truly inspired by the wisdom she shared and hope that you will be too! Read on to learn tips for how we can rise above the myth of the 40 hour work week, constructively relate to fear, harness the power of action, and break free.
Anna:
“On your Facebook profile it says you “spread love like butter”. Can you tell me a bit more about that? “
Sasha:
“I worked at a matchmaking company for a while, Dating Ring. Then about a year in I quit because I wanted to make more money and do matchmaking my own way... I took on 3 different jobs - working for Zesty catering, driving for Lyft, and starting my own business. While driving for Lyft, I decorated my car with hearts and sparkly decor to draw people in and tell them about my business. Then one day a woman from SF Chronicle got in my car and said she wanted to write a story about me. Then it all snowballed from there - eventually I was written about in publications like Forbes, Business Insider, VICE, etc....which allowed me to really gain credibility for what I do and get more people in my matchbook because a big part of what makes a matchmaker special is that they know everybody!
I’m really proud of my work. I tell my clients, if you want to talk I’m here. I become friends with my clients. I take 4 -5 clients at a time and I provide them with really high quality services. I want to know what their friends are like and who they surround themselves with because that will help me match them better and I don’t know any other matchmakers who do that - That’s how I spread the love!”
Anna:
“What would you say inspired you to leave the beaten path and brave starting your own business?”
Sasha:
“Long story short is that my main inspiration was the lack of inspiration I saw all around me.”
“I came to SF from New Orleans where I studied Public health and Psychology in college and when I got here, I started living in a place called the Convent - it’s an ex nunnery turned artist collective. I lived there with 24 other people and developed an affinity for city life and living with other people. The first job I had in SF was working at a tech start up that rang a gong every time they made 10K - you know the kind of place that makes you want to throw up every time you walk through the door - and they were paying me like $11/hr. They didn’t value community or treat people well...and I realized I needed to work in a space that values relationships and building community. I was living a double life working at this souless tech start-up and then coming home where life was all about community. It felt disjointed, to say the least and it inspired me to crave something with more soul.
I also felt inspired because I saw a problem that nobody had really solved creatively - which is dating. American dating culture leaves a lot to be desired, and the Bay Area has its own special problems. I mean, honestly you can complain about dating ANYWHERE, but I think the app culture in the Bay Area is its own animal. The idea of matchmaking, which is person-oriented and doesn’t involve much tech, in San Francisco, the hub of all things tech, really inspired me. THIS was the place I could really make a difference.
I always see people constantly being let down by online dating tools, searching for deeper authentic connections. Even now people keep coming up to me with app ideas and I’m like dude! The next frontier for dating isn’t apps. This is a human problem that’s way more complicated than just using an online tool to meet people. I do everything in person or through video chat. I saw an opportunity to really show people that there are ways to find people to mate or partner with beyond online dating. Long story short I guess is that my main inspiration was the lack of inspiration I saw all around me.”
Anna:
“What would you say is a societal “should” you feel that you’ve let go of to go off the beaten path?”
Sasha:
“Oooh, I like this question! The first one to come to mind is that that you should work 40+ hours a week. That’s one of them for sure. I don’t like to work that much and it’s an arbitrary number that was created in the industrial revolution. I still like working, but I want to work smart. I don’t want to be a slave to this arbitrary work schedule. I think America has an obsession with work that’s unhealthy and I didn’t want my lifestyle to be defined by that.”
Anna:
“What were some surprises you encountered in your process of venturing off the mainstream trail?”
Sasha:
“I was surprised by the power of action. We spend so much time in our heads wondering what if...But when you actually just do stuff there’s a lot that can come from it!”
“Venturing off the beaten path, I was surprised by the power of action because we spend so much time in our heads wondering...Is this going to work? What if I do this? What if I do that? What will people think?...But when you actually just do stuff there’s a lot that can come from it and if your heart is in the right place people will go out of their way to support you if you show them that you’re really willing to work and dive into action.
Every day, the biggest obstacle I face as an entrepreneur is myself. I think I can say that on behalf of almost all entrepreneurs. Because you have to wake up every day and say I’m going to motivate myself and believe in myself and believe that what I’m doing can make change in our world and that I’m capable of making that change.
Sure I have days that go by sometimes where I don’t do shit and I’m sitting on my ass having anxiety about it and feeling depressed. But none of the negative stuff I say to myself is true. It’s just a false narrative. I know I create change in the world because my clients tell me so. Outside of helping people find their other halves, I get feedback after dates and use that feedback to coach my clients and really help them improve on their dates.”
“You have to wake up every day and say...I’m going to believe that what I’m doing can make change in our world and that I’m capable of making that change. ”
Anna:
“What do you think are some things that helped you in gaining courage for starting your own business?”
Sasha:
“Community support. Other people believing in what I’m doing. And also, privilege. I am privileged. I know that my family would support me if I needed it and I think that’s an important thing not to skip mentioning. Also, trying out more conventional lifestyles and recognizing that they truly just aren’t for me gives me courage and motivation to make the non-conventional work.”
Anna:
“What do you think are some ways men could step up to fuel the empowerment of women in the business world and beyond?”
Sasha:
“Understanding the underlying dynamics within a monetary negotiation...educating themselves on how women negotiate and the problems they face in a negotiations and being more sensitive to that. I know a lot of women who do amazing work and they undersell themselves because they don’t know how to negotiate well because they’re much more accommodating.”
Anna:
“What’s your view of vulnerability?”
Sasha:
“Vulnerability and authenticity go hand in hand. I think they are some of the biggest strengths a person can have.”
“I think that vulnerability and authenticity go hand in hand. I think that they are some of the biggest strengths that a person can have. I think that to bring it back into the entrepreneurial context being vulnerable and authentic with my clients is one of the biggest ways that I get clients because they trust me and it helps them go into a vulnerable space as well which is important because if I’m going to do a good job I need to be able to see my clients for who they really are.
Anna:
“What do you think we need to break free? On the individual and societal levels?”
Sasha:
“Hmmm...I feel like this could be a philosophical dissertation [giggles]. That’s probably the toughest question you’ve asked me. Freedom is...I think freedom is empowerment in the moment. It’s understanding that regardless of how shitty your situation is - that in most situations you have the choice to change your outlook and make the best of it. I think understanding that is what we need to break free on the individual level.
On a societal level, I think we need to have more institutions of foundational support that can help people have their basic needs met. Things like Universal Basic Income and health care. I have socialist leanings in this way. Once all people have their basic needs met, then it would be up to the culture and society at large to re-write the script that society has written for us about what it means to be a happy and healthy person in this world.”
Anna:
“What’s your relationship like with fear? “
Sasha:
“I feel fear every day. I try to combat it with presence... I also try to accept it and experience it with awareness because it’s a core part of our human experience.”
“I feel fear every day, especially in the work that I do because I’m the only person in my business and I support myself which is scary sometimes. But my view of it is that I try to combat it with presence because fear is future oriented - I have a pretty regular yoga practice and I’m trying to build a meditation practice. But simultaneously I also try to accept it and experience it with awareness because it’s a core part of our human experience.
When I started my business, my dad kept saying it was an “experiment.” Now, three years in, I feel confident enough to say that it’s not. It’s my life and by taking an unconventional path I’ve proved to myself that a lot of the fears I had initially were projections of other people’s fears that were projected on to me - so I’ve been able to let a lot of those that weren’t mine to begin with go.”
Anna:
“How do you take care of yourself when you’re stressed to keep your badass energy shining bright?”
Sasha:
“Yoga, reading, talking to friends, go out in nature - pretty typical stuff to be honest [giggles]. I’m trying to think if there’s anything I do that’s unique…[pause]...Oh recently I’ve started a practice of praying to my future self and to my past self as a way to understand my place of where I am right now and to keep in perspective that this too shall pass...and that I have other orientations than the present moment. It’s important to be present, but it’s also important to understand the greater context in which we live...I heard that suggestion from a podcast “super soul conversations” where Oprah interviewed Will.i.am. It was a really inspiring episode. I highly recommend it.”
Anna:
“What’s the biggest piece of advice you would give to someone who’s considering a creative endeavor that’s off the beaten path?”
Sasha:
“The biggest piece of advice I would give is just do it - and it’s simple and cheesy like Nike right? [giggle] Ha! But that’s really what it’s all about. If you do it and make mistakes and learn from them and then keep doing it, you’ll eventually keep getting better and you’ll have a product to show for it. JUST DO IT!”
JUST DO IT…AND MAKE MISTAKES…AND LEARN…
THEN KEEP DOING IT!