Ali Kriegsman is the co-founder and COO of Bulletin, a venture-backed retail technology startup based in NYC and named a Forbes 30 Under 30 recipient and one of “The Most Creative People in Business” by Fast Company. Ali is publishing her first book, How to Build a Goddamn Empire, on April 6, 2021.
I had the opportunity to interview Ali recently. Here are some of the highlights of that interview:
Jill Griffin: What led you to become the entrepreneur you are today?
Ali Kriegsman: I grew up with entrepreneurial parents who launched and ran a production company that made commercials for TV and movies. My mom is an incredible businesswoman and salesperson, and I watched her do her thing. While I admired her immensely, I never thought I would go into entrepreneurship because it can be a very volatile lifestyle. My family faced a lot of financial hardship and a series of medical crises in my teens, and it caused a deep sense of anxiety and instability. Meanwhile, all of my friends’ parents had “more stable” jobs, and somewhere along the way, I convinced myself that was a better route for me. I wanted consistency.
After I graduated college, I worked at Conde Nast, the publishing company, for about a year. Then, I went to work at a tech startup called Contently, where I met my business partner Alana. I was the number one salesperson at the company for a period, pulling a six-figure salary plus commission. Still, I felt like certain parts of me that were more creative and entrepreneurial weren’t being fulfilled. I wanted to start building the “right” me and putting myself on a path to more fulfillment.
Alana and I started Bulletin as a completely different business. It was a newsletter that featured the coolest emerging brands, and then you could shop their products throughout the story. It was a way to be true to myself and flex certain muscles that weren’t getting enough attention at my full-time job. Long story short, the side hustle simply expanded and evolved. Alana came to me towards the end of 2015 and said, “We have an opportunity to do this full-time. Is that something that you’re interested in?” We had just won a $20,000 grant from an accelerator program, and at the time, that felt like a massive amount of money. It was a once-in-a-lifetime opportunity to see if I could become a successful entrepreneur. It was risky, but a voice inside of me told me to give it a shot and see what might happen.
Griffin: That’s fabulous. Why did you write your upcoming book, How to Build a Goddamn Empire?
Kriegsman: I was 24 when we started working on Bulletin full-time, and I looked to other female founders for inspiration. I couldn’t relate to a lot of them. At the time, people were starting to work at glamorous co-working spaces, and promoting your side hustle or business on Instagram was becoming popular. A lot of women were sharing their highs and not being candid about their lows. I felt very alienated. I believe entrepreneurship is a daily battle. It’s really a rollercoaster. You’re always making mistakes, and I felt like all of these household name founders on magazine covers or in my Instagram feed were so aspirational to a point where it seemed like they had everything figured out. It seemed like no one else was having negative or challenging experiences. Because of this, I wanted the book to serve as a companion to any entrepreneur who feels the same. I want them to hear from the 30 other female founders and me in the book where mistakes, pivots, disappointments, and failures happen. What makes you a great entrepreneur is persisting through them, building resilience, and investing your time and energy in the company, regardless of those hurdles. Any woman in business that feels alone or feels like everyone else has it all figured out can read my book and know that they aren’t alone at all and that there is always more than what meets the eye.
Griffin: I love the title of your book and the message behind it. Tell me, what are the biggest mistakes you want to help other founders avoid as they launch and scale their companies?
Kriegsman: One of the biggest mistakes I’ve seen is picking the wrong financing vehicle. For example, a lot of businesses take on or aspire to take on venture capital, which is this high-growth, high-risk form of capital. But if you don’t have a business that can scale and meet investors’ expectations, that money might be screwing the business over in the long term. I have female founders come to me all the time and ask, How do I get investors? How do I get outside investment? How do I meet these VCs? The book clarifies what venture capital is and isn’t and the types of companies it usually makes sense for. And how taking it when you don’t need it can harm your vision long-term. I interviewed a few founders that had this exact experience.
A big mistake I made when going full-time with Bulletin was not building a strong enough support system. Most of my friends were on a more stable and linear path. If I couldn’t chip in the same amount for dinner, or I was busy doing something for Bulletin and wasn’t available, some of them took it weirdly. I moved into a less desirable apartment and had to take on three different roommates to afford rent. I wasn’t making a real salary. Meanwhile, my friends were getting promoted. Rather than adding to or changing my support system, I became insecure, because those friends couldn’t understand me or support me in the right ways.
Another common mistake is avoiding change when change is necessary. Bulletin has pivoted twice because we reached a ceiling with the business model or wanted to scale and build a more significant business. People often convince themselves that maybe things will work out, and tend toward inaction. I’m passionate about helping women become more comfortable with change, especially dramatic change. Because sometimes, acting fast is the answer to your biggest business problems.
Griffin: That was very insightful, thank you. What can other entrepreneurs learn from you and the book?
Kriegsman: A lot of women have made radical career shifts because of the pandemic. My book will help them be more confident and less fearful as they build their empires or figure out what’s next. But they’ll also learn from a whole crew of 30 other incredible women, including Meena Harris, Kamala Harris’s niece, who runs a booming apparel business called Phenomenal Woman that sells via our wholesale marketplace. They’ll learn from Trinity, the co-founder of wellness empire Golde, who won the Glossier Grant last year. I also feature Dame, a crowdfunded company that makes sex tech products, such as vibrators and lubricants. The book features founders running businesses of all shapes, sizes, and scale, and we cover everything from managing impostor syndrome, to finding a business partner, to nailing your brand identity.
Readers will also learn that being successful doesn’t necessarily mean that you’re a rapidly-growing company taking over the world. If it brings you fulfillment and some extra income, that’s your empire – and you deserve to be proud of it. I am excited to see the impact the book makes on other entrepreneurs.