Sasha Hoffman graduated UCLA at age 19.
Completing college in just two and a half years, she majored in accounting, economics and political science. In addition to finishing early and majoring in multiple subjects, she was also involved in a variety of school activities.
“Part of the reason why I went through school so fast is that I would take over 20 credits a quarter—I just loved going to class. I majored in multiple things, I was involved in our undergraduate business society and I did a couple of finance internships, which I really enjoyed. Growing up as a competitive dancer, I continued to compete in college and I choreographed for our school dance team every year I was there.”
Fun fact: She’s internationally ranked as one of the top belly dancers in the world.
Sasha explained how her parents are both immigrants—her mother is Indian and her father is Russian, Polish, German and Dutch. Although she grew up in the Bay Area, she was constantly going back and forth between the coasts for competitive dance and gymnastics.
“I was dancing since I was out of the womb. You got to see the competitive side of me for a very early age.”
During one of her summers at UCLA, Sasha kick started her finance career as an intern at Lehman Brothers.
“I was really good at math and I liked finance—it was a certain side of the business that I felt like I was good at. I interned in their consumer retail group which focused on doing mergers, acquisitions and IPOs of consumer related companies. That time was the birth of social media and e-commerce so I switched to the technology group and that became my start in the tech world.”
After college, Sasha decided to join Lehman Brothers as a full time investment Banking Analyst in their technology group. She loved her role because so much was happening related to the growth of ecommerce and social media. Although she worked ridiculously long weeks, Sasha liked that she was often directly involved in deals and part of interesting projects.
As luck would have it, shortly after coming on full time, Lehman went bankrupt. Sasha made the decision to stay on as they were acquired by Barclays Capital and she moved to New York City to work in their Global Technology Group. After a year, she decided it was time to move back to San Francisco where she worked for two years as an Investment Banking Associate at Goldman Sachs.
“During my two years at Goldman, I had the unique opportunity to do large deals with companies like Yelp and Facebook. At a certain point, I realized that while I loved these types of companies, I didn’t know how to run one. I knew I wanted to operate a business someday and I wasn’t learning how to do that at Goldman. After a little over five years in finance, I decided it was time to make a career change.”
Leaving the banking world behind, Sasha decided to spend some time exploring her options. During her time in finance, she worked with a variety of social media, internet and SaaS companies. With her relevant knowledge of the industry, she decided to spend some time consulting restaurant groups, helping them to implement new technology and run their establishments more efficiently.
“Getting back to my early days, I really wanted to find ways to take a model that was somewhat inefficient, such as the labor model associated with restaurants, and somehow make it more efficient. We did everything from inserting tablets in these restaurants to changing some of the POS systems and giving people discounts who were checking in on site. At that point, I discovered I enjoyed taking tech and applying it to different industries."
After a few months of consulting, Sasha was introduced to Eliot Buchanan, the CEO of Plastiq. At the time, Plastiq was a Boston-based, venture backed, three-person tech company in its very early stages. Although Sasha had never worked with a startup before, they decided to meet in the San Francisco airport in the spring of 2012 to discuss the possibility of working together.
“We were literally supposed to be passing through and grabbing coffee for twenty minutes. It turned into this four-hour meeting where we brainstormed how we thought the future of payment was going to look. We had forty napkins on a table, all covered in pen,” Sasha described.
Seeing the opportunity in front of her, Sasha decided to take a chance.
“They were young and they were hungry. I realized this was an opportunity for me to be a sponge and learn about all the other aspects of the business, join a startup when I've been in corporate for years and really see a different city. I was ready to be introduced to a totally different lifestyle, to see how people do business and really grow my network.”
So in the summer of 2012, Sasha moved to Boston and started working at her first startup. During her two years as the Head of Business Development, they did their series A and B rounds of funding, grew to about thirty people and moved into office space. Working in a fast-paced environment, Sasha was able to learn about everything from engineering to marketing.
“I often tell people, instead of wasting your own money and starting your own company, it's good to learn on somebody else's dime. This way, you can learn from their mistakes and you can make your own mistakes,” Sasha laughed.
After their second round of funding in the fall of 2014, Plastiq moved out to San Francisco. At that point, Sasha decided she wasn’t quite ready to go back to the west coast. After years of hard work and long hours, she hopped on a plane for a few months of vacation.
While she was gone, Sasha spent time considering her next career move. Her experience at Plastiq taught her how to grow a B2B sales funnel, think about direct consumer marketing and build a road map. After she returned to Boston, she decided to apply this knowledge to her next endeavor and started her first company.
In April of 2015, Sasha launched Fuzzy Compass, a travel site that helped travel bloggers and Instagramers turn themselves into consultants. On the site, readers and viewers could pay a fee to get one on one advice with travel experts.
“I wanted to also experience something from the ground up that I could help operate. I loved to travel. I've actually been to over 90 countries—I'm the 2016 Global Ambassador for Women in Travel and I've had my photography in magazines. I decided to run with this personal passion and start my own travel company.”
Fuzzy Compass was successful and Sasha had an option to take a million-dollar round of funding. But she decided she didn't want to go down that path. She kept the website running but continued searching for the next step forward.
“I wanted to be able to build something myself and I didn't necessarily want that funding and everything that came with it,” she explained.
Shortly after starting Fuzzy Compass, a friend of Sasha’s introduced her to the now CEO of Piaggio Fast Forward, Jeffrey Schnapp.
“Jeff told me about a publically traded company in Italy called the Piaggio Group that manufactured motorcycles and scooters, including Vespa. They were a 135-year-old company doing over a billion dollars of revenue a year with a strong background in manufacturing, engineering and design. But they knew in order to be a success story in another 135 years they needed to innovate quickly in a rapidly evolving world. They wanted to put together a new company, with a separate management team and funding based in Boston to re-think smart mobility from the ground up. The aim of this company was to build lightweight mobility products that would better move people and goods in the future city.”
Sasha saw this was an opportunity for her to work collaboratively, create an interesting product and learn how to be an operator. Putting her passion project aside, she spent the next few months finalizing the plans for Piaggio Fast Forward. It was incorporated in June of 2015.
As of today, Sasha has been with Piaggio for almost two years. As the Chief Operating Officer, Sasha manages HR, marketing, finance, legal, design and pretty much all operations other than the engineering itself. In the past two years, she’s grown the company to 35 people and prepared for a major product launch called Gita.
“It’s really interesting because robotics are a completely new space for me. Although it’s been a big learning curve, I get to use all of my skills. I'm taking everything I've ever learned and applying it here at Piaggio Fast Forward.”
Rapid Fire Questions
Brianne Shelley: Ten years ago, would you have predicted this is where you would have ended up?
Sasha Hoffman: Absolutely not. I might have predicted that I'd be in emerging tech but I certainly wouldn't have guessed I’d be working on a robot that helps humans do more—that I never would have guessed.
I get excited about going to work today. I'm the sort of person who gets bored really quickly if my brain is not constantly being used. In our world, something is changing every day.
BS: Which do you like better, being a mentor or being the student?
SH: I love school. Part of the reason why I went through college so fast is that I would take over 20 credits a quarter. I'm sort of like a sponge and I have a mildly photographic memory so I really enjoy being a student. If someone would pay for me to go get twenty degrees, I would be in school for the rest of my life.
I also like to teach people to keep aware of how quickly the real world is moving and show them the many opportunities available. Many schools seem to be so behind; skills that we need for new jobs aren’t even necessarily being taught or brought up. My reason for being an instructor often has to do with opening people's eyes. I want to help them find something that works for them. There's absolutely no reason to be working somewhere you don’t want to work.
BS: What motivates you?
SH: When I think of why I’m so self-motivated, I’m reminded of my youth. My mom came to this country with nothing from India when she was in college and while my dad grew up here, most of his family was from Europe and died in the Holocaust. We grew up with very little and in neighborhoods with gangs and kids whose natural state of being was to hate.
When I was older, we moved and I went to better schools and started to take on more myself. I realized it was up to me to make my own path and that with education, hard work, and the right opportunities, I could lead a very different life.
As a woman, you’re often called aggressive for working hard, asking for what you want and making a difference. In my world, it’s called survival, because I’m choosing not to go back to the roots I started from and creating a nice life for myself so I can take care of my parents, my children and myself for a long time to come.
BS: Where is your favorite place you've traveled?
SH: I love South Africa, the Azores (islands off the coast of Portugal) and Hawaii. They're great. I also like safari, especially the Serengeti. I often feel the need to just get up and go.
BS: What do you do for fun on weekends?
SH: Lately, I haven't had any weekends or nights because we've been launching a product. But other than that, any weekend that I'm free for the entire weekend, I'll get on a plane. I'm really good at finding last minute deals. I'll book a ton of refundable fares pretty much for the entire winter to the Caribbean. I also dance and spend time with my friends and family. I have a very active family so I spend a lot of time going to events and social gatherings. I have over one hundred relatives in New York and New Jersey and I have another forty or so in California. There's also this thing with Indian families where they just sort of adopt everyone in the neighborhood as well.
BS: What time do you get to the office and what time do you normally leave?
SH: I'm a little bit of a late bird. In college I had class at 8am everyday which was the worst decision of my life. I would literally roll out of bed at 7:40 and be walking to class in my pajamas. After banking for so many years, I'm used to going to bed later. I wake up and I'm usually in the office around 9:30 or so and I’m usually leaving somewhere between 6 and 8. I’ll take a break to either go to the gym, get food or run errands and then I'm usually working between 9 and midnight and then I go to bed somewhere between 12 and 1.
BS: How do you handle stress?
SH: I feel like I'm in a permanent state of being high strung. I have a lot of energy for no reason. I don't drink coffee because I'm always awake and alert. My best way of handling stress is make a task list and just go through it as fast as possible. I've learned that at some point, I'm not a doctor and I don’t have someone on the surgery table so whatever I'm doing is probably not critical. It is to me and it needs to get done but there's some universe where I can probably reprioritize. We're not doing any work that's life or death here.