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Natalie Sportelli | Fmr. Forbes, Lerer Hippeau, Thingtesting
Natalie talks about how her interest in story telling has led her from journalism to venture to a start-up, how she approaches her Twitter acct., and what she would be doing if she wasn't doing this
I met Natalie as a result of a challenging work day. Although the reasons for why it was challenging are now lost from my mind, I vividly remember lying on my bed and scrolling Twitter for a break. I came across a tweet from Natalie. I’d been seeing many tweets from Natalie (she is a prolific tweeter as we will discuss) but something about seeing that exact tweet in that exact moment made me want to contact her, and so I reached out to her email which was posted on her website. I never did that. I had never cold-emailed anyone before for a conversation, and I have never done it since. But something about the way I was feeling and her easily accessible email address just made me draft the note. I hit send before I could think better of it. What’s so crazy to me now is that she actually responded.
We got coffee. I asked her to be on The Kitchen Fridge’s Shelf Space feature. Luckily, she said “yes” once more.
I reached out to Natalie because I thought she could teach me something. And she certainly has. But what I’ve been surprised by most is how parallel our lives and thoughts seem even though she has been through a couple more jobs and a couple more years of life. Exploration and life-re-evaluation seem to return to us in waves, hitting from different angles but looking rather similar. Big decisions, like careers, have always seemed so heavy and rare. Talking to Natalie made me realize you can make those big decisions over and over again.
Enough from me. Let’s hear from her.
Name: Natalie Sportelli
Source of unconventionality: Making decisions by “following her curiosities”, which has led Natalie from Journalist for the Under 30 franchise at Forbes to Director of Brand and Content at venture fund Lerer Hippeau to Head of Content at start-up Thingtesting to now a life sabbatical to where? She’s not quite sure yet.
Can you talk through your career trajectory so far and how your belief in “following your curiosity” has led you to your different roles?
I didn't really think about pursuing journalism as an initial career. I’d seen The Devil Wears Prada, and I was obsessed with the feel and the process. Plus, the environment seemed exciting. So in high school, I started writing for my hometown newspaper (the Syracuse Post-Standard) in its teen column, and I had so much fun doing that. There’s just such a rush that comes with publishing.
When I went to college, I majored in English and interned at CNBC and then Forbes, where I started after graduation. Through journalism, I was exposed to so many different people and learned what motivates them. I was able to dig into how people approach their own lives.
I was particularly inspired by the stories of founders in the Under 30 franchise. They were so motivated and passionate about solving problems. Writing the Under 30 stories got me curious about how I could work more closely with founders in a way that was still using the journalistic lens of writing and storytelling. This led me to become the Director of Brand and Content at Lerer Hippeau where I worked to tell the stories of the fund and its portfolio companies through content. I didn’t realize content for VC was an area while I was at Forbes, and I’m so glad I landed in that role.
I was looking at start-ups first from the reporter lens at Forbes and then from the venture capital lens at Lerer Hippeau, which made me curious about what it was like to be inside a start-up. Moving to become Head of Content at Thingtesting (a platform for people to research and review Internet-born brands) was a very deliberate move to see first-hand what a start-up looked like. The fact that content was so integral to Thingtesting’s purpose was really appealing.
With each career decision, I followed my curiosity into new experiences because I figured those points of view would be valuable no matter where I go.
In addition to helping organizations build brands, you’ve also built a strong brand for yourself (Natalie has 14.5K followers on Twitter). How do you take the lessons you’ve learned from working in content and turn them toward yourself?
The reporter mentality is that your name is on your work and so you are motivated by publishing. You need to tweet out your articles for them to get attention. You need to tweet about what you’re looking to report on [to get leads].
A hurdle for people trying to build their personal brand online is nerves. They are nervous that no one will resonate with their posts or that they will sound silly. But working in journalism and having to post things frequently pushes you to get over that.
On Twitter, I just try to speak like myself. I try to showcase who I am to people who I might want to connect with in the future. I also try to present myself as a well-rounded person, so my Twitter might be a photo of my dog or something I’m cooking, or a book that I’m reading, and then maybe I’ll post something related to work. I’ve received opportunities and met people on Twitter by just presenting my authentic view.
This spring, you left Thingtesting to go on a life sabbatical and spend time determining which role to take on next. Can you talk about your approach to the sabbatical and what it has been like?
It has been such an interesting time, and I’m in the process of putting all my thoughts down about it. I try to accumulate new perspectives because I’m driven by this motivation to see how different things work. That’s really been the focus of this time off.
When I left Thingtesting, I was thinking about what new perspective I wanted to focus on, and I really didn’t know. So I went on a sabbatical to spend a few months talking to people to see where I could apply all of my different experiences and skills.
At the beginning of my sabbatical, I traveled a lot. And then when I got back from my trips, I did a ton of meetings to reconnect with people and hear about what they are seeing in the market. People also then pointed me to connections they felt would be interesting. I feel really lucky to have had so much exposure to hours and hours of conversation from the smartest people in the business. All of these investors and founders have amazing opinions and world views, but being able to figure out where you fit in — what the future looks like for you and what you can get out of it — is hard. Thanks to all that research, I have a really solid idea for where I can bring value and learn something new.
What has been the most surprising thing about your sabbatical?
Since starting my sabbatical, I’ve connected with a lot of people also taking them. We've heard of all these trends like "quiet quitting" and "reluctant working", but I've been surprised that the reasons why people want to take time off are all entirely different. It’s interesting to see everyone’s process and how they want to spend their time when they don’t have any restrictions. They will do anything from travel Europe to immediately jump into other types of exploration or begin offering consulting. For me, on my sabbatical, I wanted to create a balance. I wanted to travel and then I wanted to catch up with a lot of people and now, I want to get to work.
While you’ve taken on many roles, they’ve all been in the world of entrepreneurship. If you were to be in a parallel world and pick an entirely different career channel, what would it be?
I would be in restaurants as a chef/owner — someone who is on the business side but who is still involved in the kitchen. I’ve watched the Food Network since birth and every sort of cooking show. I’m obsessed with The Bear. I love cooking. I’m currently doing this recipe challenge, cooking through the cookbook No-Recipe Recipes from the New York Times. I love going out for dinner. I enjoy reading gastronomy books. The psychological aspect of restaurants and food is just very interesting to me. When I was at Forbes, I met all of these incredible CPG founders and chefs, and I just think it’s a fascinating industry.
Can you tell me about a phrase or idea — maybe from a book, a song, a life motto — that you repeat to yourself often?
I feel like I have to do my tattoo even though it’s corny. The tattoo is a line from John Green’s Young Adult book Looking for Alaska. I got the tattoo after high school graduation. It reads “I go to seek a Great Perhaps”. I got that to remind myself that you shouldn’t wait to figure out what makes life exciting. It reminds me that I’m not always necessarily seeking contentment. I’m seeking growth, life experience, and learning. It’s a reminder to not shy away from making those big decisions.1
So, where do you go from here?
I’ve always thrown myself into every job 200% and the job becomes my identity. But one concept I’m hoping to take from sabbatical and into my next role is how to have a healthier connection to what I’m doing and who I am. You become better at your job when you’re able to use your time well. The founder burnout culture that suggests you should be always working doesn’t create more happiness or productivity. A founder who loves hiking, goes on the weekend, and then comes back to work, is a more centered person. I want to do a really good job, but I also want to keep perspective. I don’t want to attach my identity just to what I do because I am broader than that.
**Interview has been edited for length
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This is also one of my favorite quotes of all time (for similar reasons.) Looking for Alaska is an all-time great and by far my most-read book (I think I’ve read it ~7 times at various points in my life.) If you haven’t read it, this is your sign.