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Alumni Writer Series: Ali Kriegsman '09

Milken virtually sat down with four alumni writers for a conversation about their book publishing journeys, creative inspiration, and reflections on their Milken experience.

Meet Ali Kriegsman '09, Co-founder and COO at Bulletin and author of the book, How to Build a Goddamn Empire: Advice on Creating Your Brand with High-Tech Smarts, Elbow Grease, Infinite Hustle, and a Whole Lotta Heart

What is the background on your business?

I have been building my business. It's called Bulletin. It's a venture backed retail startup that's based in New York. We operate a two-sided marketplace where retailers all around the country and Canada can come to our site to source inventory and discover new brands for their stores. 

Congratulations on the upcoming publication of your book! Tell us more.

I’m publishing my first book in April. It's called, How to Build a Goddamn Empire. It's about my entrepreneurship journey, but also features 30 other female founders that have built companies of wildly different stages and sizes. The book is hybrid memoir hybrid business book. I go through my journey starting Bulletin- it was a side hustle, deciding to go full time and all the financial considerations around that, the stressors around going full-time, and how to hire the first few people to your team. There's a lot of elements in there, but I think the most impactful parts about the book are the slightly more personal elements.

I've dealt a lot with imposter syndrome. As a female founder in tech, you feel very ostracized. You feel very alienated. You feel like you're not being taken seriously. And I wasn't really hearing any female founders talk about those experiences because sometimes it feels too risky. I really do feel like I'm giving, existing entrepreneurs, aspiring entrepreneurs, entrepreneurs, women who are thinking about starting a business or turning a passion into something they can monetize. I'm giving them a very candid, raw, humorous, funny and open, view into my journey and 30 other women's journeys.
What inspired you to write this book?

So I was particularly excited about the book because I felt like it was really the type of book that I was missing as I was building and scaling my business. When I started bulletin in 2015, it was on the heels of Girl Boss coming out by Sophia Amoruso, Lean In had been really successful for a few years prior. And I felt like, wow, all these business books were being written by women that had already built their wealth and were so many light years ahead of where I was on my entrepreneurial journey. And I felt like I almost needed an entrepreneurship companion or sidekick, someone that was closer to the ground writing in real time, sharing the hard-won lessons about their experience. 

Thinking back to your time at Milken, what stands out to you?

The community, the takeaways and the Milken spirit really never leaves you. My closest friends were from Milken. I went to a great college-the University of Pennsylvania-and I say to everyone who asks about my Penn education, no shade at Penn, but I really do feel like my Milken education was more challenging, more intimate and more robust. As soon as I got my book deal, I immediately emailed Mr. Martin, who I took classes with for years. I immediately emailed Amy Frangipani, who was the head of the newspaper when I was editor-in-chief. We always chat on Facebook and Instagram and to have a long-term connection with your teachers like that, you know, I'm pushing 30 now is so magical. And I think I really took it for granted for a long time.

Only really after graduating college, did I start having intimate conversations with my friends from college that didn't go to Milken and didn't have a similar school experience as me. And they're always shocked by how close I stayed with my teachers. They're shocked by how close I stayed with my friends. They're shocked by how, openly and wonderfully. I talk about Milken, because I really do think most people have a pretty negative high school experience. And I can't relate to those stories at all. High school was definitely challenging for me. I had horrible skin braces, headgear at times, and underbite, like we all went through it, but I had my little pod and, with my Milken friends, I felt unstoppable. 

I also really feel like Milken allowed for my love of learning to flourish. I took an English independent study with Mr. Martin and another classmate. I had Mr. Castillo as a science teacher, and he would always stay with me after class. I was really bad at physics and he just took the time. He never complained about it. Mr. Lee used to drive me and my late friend, David, who also worked on the paper with me, to, and from different places we need to go for the paper. He wasn't even a part of the paper. It was just such a remarkable and special community that I don't think I'll ever be able to compare to anything else. And I'm just so lucky to have had Milken as my high school experience and to be able to rely on the community and rely on the friendships I made there. 

What advice would you give to current Milken students?

I really felt like my truest self at Milken. I felt like I was able to, explore all my passions. I was in theater. I was in acapella. I was on the paper. I did that independent study. I was able to explore so many different parts of myself. And I think once you get to college, you start to get really stressed about becoming successful and what your professional life is going to look like and what your career is going to be. And I felt like so many parts of me started to chip away at Penn because there's a very pre-professional undercurrent there. When I was there, it was very normal to become a banker or a consultant or go into finance. And for someone like me, that was a little bit more creative, a little bit more entrepreneurial.

I felt like I couldn't really find my place. And I never felt that way at Milken. at Milken, it was totally normal to have a very diverse and wide range of interests. It was very normal to be involved in a bunch of different clubs and organizations and extracurriculars. And I felt like I was able to really shine and really learn about myself and explore all those different parts of myself in high school. 

So I think that my advice to a current Milken students would be really take advantage of everything that Milken has to offer, whether it's the community, the incredible teachers, the unmatched education, the clubs, the extracurriculars, because as you get older, the kind of the things that you touch and the things you can do become more and more narrow and you get more and more pigeon holds as life progresses. And high school is one of those really beautiful times. When you get to test everything, try everything and be the full bodied self that you are meant to be. I think Milken is a perfect place to do that. I did that and I feel like I'm actually coming back to myself in a lot of ways. A lot of the things I'm revisiting and reminding myself that I love to do, I was able to do for the first time and explore that at Milken. 
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