Kimmy Scotti Knows How to Spot the Next Crazy-Successful Business
She launched her first company at 15 (and landed a trunk show at Bloomingdale's), built up over a dozen businesses, and is now at the helm of 8VC.
As far as we’ve come in championing women in business, we also have a long way to go. A long way to go until we stop thinking of women in positions of power as leaders who can’t simultaneously love and enjoy fashion and beauty and run a successful and thriving business. But Kimmy Scotti, a Gucci-loving, “million-step skin-care routine” activist and venture capitalist is changing that notion. She’s been an entrepreneur since she was just 15 years old, turning a jewelry side hustle into a legitimate money-making business that landed her a trunk show at Bloomingdale’s. (NBD.) Over the next 15 years, she built up countless companies in the healthcare and fashion realm (some of which we bet you use regularly) by way of her direct-to-consumer technology knowledge, before becoming a venture capitalist at 8VC. Like I said, she’s a big deal.
She also happens to be one of the nicest, smartest people in the business (see what we mean with doing away with those “boss lady” stereotypes?). Over the last few months, Scotti and I have become phone pals—finding a person who loves to talk over text as much as I do is rare these days—talking career paths, finding ways to keep an inbox at zero, and sharing advice for women looking to become entrepreneurs or get into venture capital. Below are her incredible insights.
Tell me a bit about your path to 8VC:
“My journey to venture has definitely been atypical. Funny enough, I got my start in fashion! When I was in high school I started a jewelry line, which was a ton of fun and gave me my first real taste of that entrepreneurial Kool-Aid. It was doing quite well, actually (I was doing trunk shows at Bloomingdale’s at just 18). I thought that my career would focus on the fashion industry, so I went to the Fashion Institute of Technology.
“One of the things that I learned while working on my line was how broken the infrastructure was around wholesale/retail order management, and seeing how I’m obsessed with problem-solving, I started talking to people who could help me figure out a way to fix it. This led me down a road of direct-to-consumer technology, and after meeting Nicole Williams, I decided to wind down my jewelry line and join her to build the content platform for young professional women called WORKS by Nicole Williams.
“When exploring angles for monetization, we ended up building a digital magazine business that optimized content for the iPad, making it shoppable (and providing our members with discounts). This connected the consumer technology and fashion dots for me. Funny enough, it wasn’t the fashion links that performed the best for us. There was a link in our healthcare publication to a prescription coupon code, and we found that a majority of our revenue was actually from people buying in to get access to that! At the end of 2011, we shifted our focus to healthcare, to a company that developed a prescription discount card that focused on solving big problems. While I ended up engaging in a totally different business from the one I set out to build in the beginning, I landed exactly where I wanted to be: focused on solving big problems with creative solutions.
“After 15 years of building companies from fashion to healthcare, and after a few years of angel investing (fun fact: Danielle and Whitney at Sakara Life received the first angel check I ever wrote!), I found the thing I loved the most was working with founders. Venture capital was actually a super logical next step, though if you would have told the 18-year-old version of me that, she would have definitely laughed at you.”
What does a typical Monday look like for you?
“I kick off the week with a trip to San Francisco to spend a few days with my partners and team. So Monday mornings involve waking up at an ungodly hour in order to be out the door and on my way to Newark Airport for my 6:00 AM flight. I still make time for my million-step skin-care routine though—you have to take care of your skin when flying 6k miles a week.
“When you travel as much as I do, on the same flight every single week, you make fast friends with the people at the airport. So after going through security, I make my rounds and say hi to my friends, and pick up the scrambled eggs and avocado that the guys at the bagel place make for me.
“Once on the plane, I try to get in another hour or two of sleep before planning for the big day ahead. The remainder of my flight is spent on email—my goal is always to get my inbox to zero by the time I land so I can go into Monday meetings with a clear head.”
Being able to get an inbox to zero is an enviable quality! What happens once you get to the office?
“So, after rushing from the airport to the office and throwing my heels on (I never spend a day without them), I head to a stacked day of internal meetings—a routine we have every Monday. At 10:30 AM (PT) I sit down with the partners and talk high-level strategy, which is followed by team lunch and meetings with the larger investment committee to discuss active deals as well as progress with companies already in our portfolio.
“After those meetings, I have a chunk of time designated to ‘zoom-in’ during syncs with my founders and my immediate team. If I’m lucky, I’ll maybe get a moment of zen to myself to revisit the already-overflowing inbox, but it doesn’t always happen.
“The afternoon continues with two hour-long pitches from new companies to the investment team. This is one of my favorite parts, actually; hearing how each of the members of the 8VC team ask such different questions really challenges and excites me, and I love getting to really dive deep with the founders to learn about different markets. We’ll then cap things off with our All-Hands meeting. I love how electric and energized the room is when we’re all in the office together. The team really makes the flights worth it.
“If I’m lucky, I’ll conclude my Monday with dinner or a cocktail with my best friends, Alex and Christine, who live in San Francisco. And of course...my million-step skin-care routine.”
How do you control your inbox and manage a team throughout the week?
“I use my email like a to-do list. I leave the message unread unless I’ve done whatever the task is that the email required. I try to keep my unopened emails relatively low in general. I’ve gotten really good at viewing only the things that I can do and asking for support on the things that I know someone else can do. I have an amazing team, and for a long time I was not a great delegator. The people around me are incredibly smart and capable. In the last couple of years, I had to get really good at delegating, because the volume of things [I had] to do was just so high. As soon as I see something that someone else can do, I share it with them and ask for help. I think that’s good advice for everyone, to only do the things that only you are good at, and then everything else that is someone else’s skill set, ask [them] for help.”
What does the latter half of your week entail?
“I spend the tail end of my weeks in New York, so I’m back home at this point.
“When my schedule permits, I love to start my day with a workout. These days I have Pilates, SoulCycle, and Bari in my rotation. Luckily, I’ve always been someone who wakes up with a ton of energy, so I always head to the studio first thing. I love the way I feel when I’ve managed to get a good sweat in by 7:00 AM.
“I’m currently in the process of converting [to Judaism], which I’m so excited about. I’ve been taking cooking classes so that I can host Shabbat dinners (no, this is not required, and yes, I am a teacher’s pet). So on Friday mornings, before the rest of my team is awake in San Francisco, my chef friend Jennifer Abadi comes over to my apartment and schools me on all yummy things Sephardic and Judeo-Arabic. By the time we wrap at 11:00 AM, I have a six-course meal in my fridge that I’ve made from scratch!”
How do you find the energy?
“I get so much energy and inspiration from the time that I spend with our founders. Usually by the time Friday rolls around, the chaos from the beginning of the week has subsided a bit and I’m able to spend some really focused time with them. This looks like something different every week, but there’s a big focus on high-level strategy with companies like uBiome and MakeSpace.
“I also try to see my sister (my co-founder at Monthly Gift & Dear Kate, and generally just my favorite person on the planet) as often as I can when I’m in New York, so I’ll try to spend a few hours a week with her at our office in Midtown when I can swing it. Uber trips between my place in NoMad and our portfolio companies’ offices always have calls scheduled during them—wasted time isn’t really part of my language.
“Then it’s back up home before sundown so I can break bread with my favorite people. Doesn’t get much better than that!”
How else do you decompress?
“I wind down at the end of the day either with a cocktail with my best friends, or I’ll go through my lifetime skin-care routine and try to really relax into that. I try to watch comedy at the end of the day, either when I’m going to sleep or right before. I find that really decompresses me, so I’ll watch an HBO stand-up or something like that at the end of a Monday.”
Advice she would give female founders or venture capitalists:
“As a founder you’re never quite prepared for whatever it is you’re setting out to do. There’s a lot of taking a risk and a leap. I would say get comfortable with that discomfort and just go. Stop waiting to be ready. Because you’re never going to feel ready. It’s never going to be the right time. So just going and doing is really the best way. That’s founder advice, I would say. As a female investor, I focus on the process of trying to solve big problems. Remember that women have a natural commercial inclination. We consume 80 percent of everything, and so we have a really good, natural feel for markets. You have this incredible ability to understand a market in a way that’s really natural. I think women don’t believe that that’s a value, and it’s an incredible value actually.”
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