Kimmy Scotti: Partner at 8VC, Entrepreneur, Creative Genius
What has the journey been like to where you are today?
"I started my first business when I was 15. I was out walking in New York City and someone tried to buy a necklace I’d just made right off of my body, so I quickly did the math in my head and sold it to them. At the time, why I knew what wholesale and retail was is beyond me, but it all got me thinking, ‘I could probably do this for a living. I could probably make jewelry and sell it.’ So I started to create the line – Mimz New York. I created a collection and started pounding the pavement locally. A designer store picked it up, and people started wearing it. I ended up building the business all the way through college.
While I was in school, I worked in a showroom with a pajama company. At the time, they wanted someone to come in and help sell their line. I said ‘Well, if I can use your showroom to sometimes sell my line too, then it will be really collaborative.’ They ended up hiring me, and soon after licensed their line to Target. Eventually, we started another label, which was a higher-end pajama label. I ended up doing all these start-up type things, and all in fashion.
Then, I got this experience with Bloomingdales buyers, and it was an absolute nightmare. I decided, ‘I’m going to build technology to talk directly to consumers and not go through buyers to know who my consumer really is,’ because they don't know who she really is. That spawned this idea that I was going to build technology — although I really didn’t know anything about it. I ended up being connected to Michael Loeb, who had just sold his company, and I went to work for him on something new. For eight years, I built companies with him and a great team, and ended up co-founding a health-care company with him that was originally a digital magazine platform that we were building. It ended up scaling incredibly quickly. By the time I left the day-to-day operations at the end of 2014, we were helping over 10 million Americans save over a billion dollars on their medication purchases — with only about 30 employees.
At that time, Whitney and Danielle came to me through a friend of ours to talk to me about how they were building Sakara. This was really the first investment opportunity I was excited about. I really fell in love with that investing process, because it's like you’re a fairy godmother. People come and see you and they’re like, ‘Hey I have an idea…this is what I’m thinking about.’ You give them a little bit of fairy dust (money) and advice and that helps them to grow. It’s a really fun process.
I decided that I would go industrial strength in that and raise a fund. I partnered with two amazing guys, Drew Oetting & Jake Medwell and we raised a fund to invest in earlier stage companies. We eventually came together and built a much larger fund with two additional partners, Joe Lonsdale & Alex Kolicich, called 8VC. We invest in technology companies at various stages, but our sweet spot is series As and Bs.
Somewhere in the middle of starting the fund, my sister LisaMarie, and I came together to build our own thing: Monthly Gift, a feminine care subscription service that delivers customized boxes of tampons, pads and liners to women at home for as little as $10 a month. It’s powered by our period tracker and fertility app. It’s been crazy growth so far and has been so fun to work on with LisaMarie."
What is it like working with seed stage companies versus later stage ones?
"For seed stage companies, sometimes they’re just an idea and a powerpoint. When you’re looking at something it’s about, ‘What is the market for this? What is the market size? Do I believe that this person is the right person to take this idea to fruition?’ It’s more about people. It’s about whether or not you believe that they're the right jockey for this horse. Then you have to think about whether or not the horse is on the right track. You need to believe that person is a flexible enough thinker to understand that when they learn something new, they may need to change direction.
Then in later stage companies, the real difference is that there has to be traction in their business already. You’re looking for someone who is like, ‘Alright, I had an idea, and I got it from 0 to 60, but now I’m taking that next step.’ Here, we’re looking for someone who understands their operations, they really understand their business and the market and now they need support in their growth."
Where does your inspiration come from?
"I’m super ADD so my brain needs to be fed all the time! I actually just had dinner with a very prolific investor. He was talking to me and I picked up my phone and started doing something, and he was like, ‘Literally no one has ever done that to me.’ He said, ‘Your ADD is actually worse than mine.’
Post-college, I was very scared of this idea that I would stop learning. A lot of people you meet, 10 years out of college, haven’t read a book since. And I just couldn’t wrap my head around it, so I implemented this idea of 21 credits for life. Every week, I spend 21 hours learning things. Some things count, some things don’t. Like...cooking counts, if I’m learning a new recipe, but if I’m replaying an oldie, that doesn’t count. The gym counts. Museums count, documentaries count, reading fiction and non-fiction counts. But watching a romcom doesn’t count.
Meeting people who are outside of your space counts — which for me, is actually a lot of my learning hours. I pretty much kill all 21 hours in just meeting with experts in different verticals. I get to spend a lot of time with really creative people. I always tell young entrepreneurs, ‘You’re a genius, you create stuff with your brain!’ They’ll be like, ‘No this thing that’s in my head right now isn’t good enough, I’m not going to make something exist.’ And then three to six months later, it exists. It’s really crazy. I always think of entrepreneurs as being artists of a different medium.
I think that dedication to learning is inspiring. I like to take inspiration from completely different industries. It’s easy to have a lot of your friends be from inside — other entrepreneurs and investors. That’s great and super inspiring. Obviously, a lot of people closest to me fit those molds, but I also have actor and designer and graphic artist and writer friends who are completely different from me."
You have so much going on in one day, how do you juggle it all? How do you stay grounded?
"For the past two and a half years, I’ve been meditating a lot — really trying to bring back my gut instinct. If you keep fighting all the time, you can kill your gut instinct. It stops talking to you and you stop recognizing it. I think it’s really important to get that back. Once I started meditating, it became so loud and constantly let me know if I was doing the right thing or not.
Also, when I’m making decisions, on the inside, I always say it to myself like a headline. ‘What if my mother had to read that headline, what would it say, and would it be okay?’ I’m constantly telling myself this story before I do something.
I think that a lot of times, people on the outside look in and think that everything’s better and more neat and more purposeful than it looks. But most of the time, you’re just running and tripping and your shoelaces are tied together. You’re still moving forward.
Sophia Amoruso said something like, ‘Don’t compare other people's highlight reel to your hustle.’ As you get older, your life looks like a highlight reel. People see you speaking and traveling and whatever, but they don’t know how much you may be struggling. At one point, I was without a paycheck for 18 months and was paying for things to be started with my own money. Everything was draining me. I thought I was going to run out of money soon. The result of that was me bawling under my desk for 90 minutes. My sister was like, ‘You’re going to have to come out from under your desk.’ And I was like, ‘I can’t, don’t make me do it. Call mom.’ She was like, ‘We’re not going to call mommy, you’re 30. Get out from under your desk.'"
In those extremely hard times — we all have them! — what keeps you going?
"Trying to take lessons from all the failures. When you get actual physical pain from whatever happened, whether you’re having a breakup conversation or you fire someone, you’re having that conversation for a reason. I try to use all of those really hard experiences, all the failures, and those physical feelings as ways of growing. The clench on your heart is not a clench, it’s expanding. It’s learning a new thing. Next time, you’ll be better at it. The failures are just stepping stones to the next big win, and mostly, you’re tripping and falling the whole way along.
The life of an entrepreneur is a struggle everyday. The struggle is real. The hustle is insane. It never stops and you never sleep. And even on the worst day, it can still feel like a record amazing day because you love it and you’re still learning."
What’s it like being a woman in a male-dominated industry?
"I’m definitely a card-carrying feminist. Being a female in a male-dominated industry is one of the craziest things. 40-1 is even a common ratio I've experienced. How does that happen?! I can be at a dinner with 100 people, and there will be just two women in the room.
To start, you’re a different creature, so that means you get a lot of attention. It also means that some of the attention you get is negative. I try to remember the times when it’s hard — when some male idiot entrepreneur is hitting on me with their pitch, or you get the “deck pic” the day after a date because they find out that you’re in the industry — that I have to be on my game and make sure that I do more work for the same amount of success because if I’m wrong, then the understanding will be, ‘Girls shouldn’t play at this.’
I spend a lot of time thinking that the future of female entrepreneurship and venture rests on me. If I mess it up, then the next girl that hears about it isn’t going to do it because they’re going to be afraid. I want more women in investing because it means that more female-focused businesses will get funded, and more of our own problems get solved by women. Who better to find our own solutions than us? Monthly Gift is for women, by women. Our team is almost all female. That was really important to me.
Once, I was sitting in a pitch and this guy was telling me about drones, and I’m a really interested person in general, so I was excited about it and asking him questions. Then the guy leans in and kisses me. In a pitch. In a conference room. In the middle of a Wednesday. He literally leans in and plants one on me, open mouth. I was like, ‘Whoa! What are you doing?’ He’s like, ‘Did I read that wrong?’ He stood up super embarrassed and was pacing my conference room. I said, ‘Why don’t you take a walk around the block and cool off, then walk back in here, shake my hand, and we’ll try this again without you trying to make out with me in the middle of your pitch.’
This is the kind of thing that happens every now and again. It’s terrible, but it just happens, and I’m figuring out how to handle it with humor and grace. Snapchat, as a concept, has really helped me because everyone understands that it disappears. I’m like, ‘Do you know Snapchat? Well in 35 seconds, this is going to disappear, and we’re going to be friends, but right now you’re going to listen to me.'"
What is your strategy for work-life balance?
"I don’t have this all figured out, but I have it better figured out than I used to! I used to make excuses all the time because I was always traveling. I’d think to myself, ‘I’m going to eat macaroni and cheese because I’m so tired.’ Or I’d allow myself to have dessert because I was traveling. Then, I was traveling 100% of the time and when I came home all I wanted was comfort food. and I'd make the excuse to not workout because I was too tired from traveling. I kept making all these excuses, so now, I’m never allowed to have another excuse.
My morning regimen is hilarious. I rocket ship out of bed: give myself a countdown from 10 to 1, then jump out of bed and kick my feet in the air. It makes the bed shake. It gets my heart going and pumping. Then I start my day.
I meditate for at least 10 minutes each day. I wake up at five-ish. I’m not a sleeper. I’m one of those really lucky people that essentially doesn’t need a lot of sleep. I’m a four hours a night person. When doctors recommend more sleep, I say, ‘Are you crazy? I have an incredible gift here where I have more hours in the day.’ At the end of the day, everybody wishes they had more hours in the day. I get four extra. That’s a bonus! Mozart said, ‘Sleep, those little slivers of death, how I despise them.’ He knows what’s up.
Anyway, that’s my morning routine — I rocket ship, I meditate, I work out, then come back and dress. I relish the getting dressed part. I look at my schedule and ask, ‘What’s coming up today? Is today a job for a red dress?’ I put on whatever makes sense for that day’s activities. I’m fast at it but I take time to do it the way that I want to because I feel better when I’m all dressed up. It’s also part of my personality. I’m a girl who really loves being a girl. Then I head out the door like, ‘Let’s do this. Show me what you’ve got, day.’
Food-wise, I have a pretty strict diet of being gluten-free and vegetarian — Sakara feeds a lot of my needs. Then when I’m traveling on the road, I take the Sakara granola. I take some bars with me and the detox tea. I pack my bag with all these things that I know are healthy snacks."
Best advice for entrepreneurs?
"The most important thing I always wish I could tell myself when I was younger, is that the hard parts are the good parts. If you don’t like the day to day stuff, it’s never really going to work. The hard conversations — selling a new partner and raising money and building something and talking to your developers and team — if that part is not rewarding, then it’s just not really for you. Look around and enjoy that and really relish those parts.
Actually building something new that didn’t exist before makes you a creative, mad person. A lot of my way, I was ripping my hair out, afraid and struggling and worried and panicked and whatever. Now, I’m like, ‘Kid, you’re going to be fine. It’s all going to turn out okay. If you love the building part, then this will all be worth it.'"
What’s your idea of legacy?
"I feel like a lot of the things I do, I do because I want my sister to know that they can be done. She is one year younger, which is not that much, but she’s like my example of all women, I’m always just trying to be a good example of abundance. I want to have been an example that you can really do anything. We didn’t come from a lot of money. We weren’t educated in any of the "right places". But we know you can make your own life, and make your own luck. And for women, if they have an idea, they can find a champion who will help them build that, or they can do it themselves. That’s why we decided to build Monthly Gift together, to be good examples of possibility and abundance. We can build whatever we want, however big we want, and all of it at the same time."