How This Founder Grew Her Side Hustle Into a Multi-Million ‘Goddamn Empire’

24, 2021

10 min read

This article is written in partnership with to promote Yelp’s Women In Business Summit, a free, two-day event which begins today. (Entrepreneur is a media partner.) Answers have been edited and condensed for clarity.

When Ali Kriegsman started Bulletin with co-founder Alana Branston in 2015, the company started as a shoppable newsletter, evolved into pop-up markets around , and eventually put down roots in the form of brick-and-mortar stores. But after six years, a couple of stints with startup accelerator Y Combinator and $10 million raised in funding, Bulletin has pivoted to the online world.

Now Bulletin aspires to become a leading wholesale platform for retailers to discover and buy products from independent brands. The pandemic has accelerated the company’s growth, and Bulletin is now looking to grow beyond its team of 19 people by building upon its product and engineering teams.

We spoke with Kriegsman about her journey in the entrepreneurial space, from starting her business to writing her book How to Build a Goddamn Empire, along with her advice for women interested in .

Tell us a little bit about your company. What is it and what does your company do for its clients?

Behind the curtain, retailers all around the world, have to source inventory from somewhere. Bulletin is one of those somewheres. Independent retailers use Bulletin to discover new brands, products and inventory for their locations, so that they can sell it to their end customer.

Without Bulletin, brands usually have to pay upwards of $30,000 to showcase at a trade show. We allow brands to increase their distribution with these retailers, or even online retailers, without having to go through those crazy expensive, convoluted and time-consuming traditional channels.

Bulletin started out as a shoppable, ecommerce newsletter spotlighting the coolest emerging designers. We then layered in pop-up markets that we did every weekend in Brooklyn throughout 2016.

Then we decided to go indoors and open our own locations around New York. In total we’ve opened five stores in New York. We don’t run our stores anymore, because we have fully invested in the wholesale marketplace. But having that experience as a retailer and feeling like the discovery experience for finding great brands was really disjointed was why we decided to launch the marketplace.

What is your role and what are your day-to-day responsibilities?

I am the COO at Bulletin. What that means in practice is I keep a lot of different trains on the track.

I pretty much oversee growth, communications, positioning, PR for the business. And my day-to-day looks like strategy conversations with my co-founder and our CEO Alana [Branston], one-on-ones with our director of growth or our director of marketing and merchandising, checking in with our growth analyst to see where we’re at to goal for signups for the month or what our conversion rate on emails are looking like. Then I work collaboratively with Alana to make a better user experience for our customer.

Related: If Running Your Business Feels Hard, You’re Doing it Right. Here’s Why

Talk a little bit about your journey into entrepreneurship. 

Alana and I met at a Contently, which is a software startup in New York. I wrote for Contently’s book club and I wrote my own personal blog. Alana was interested in launching this newsletter, and just kind of approached me and was like “Do you want to be my editor in chief?”

[Bulletin] started out as a way to supplement my sales job. It was never making me crazy money. It was like a bootstrap . But the more that we worked on it, the more that I kind of asked myself, “Well, why not me?”

Bulletin ended up getting a $20,000 grant at the beginning of 2016. I just decided to kind of close my eyes and jump off the cliff and see what happened. I really wasn’t one of these people who always knew I wanted to build or start a business. If anything, I was really against it, but I think actually doing it and getting in the weeds with it, and then having this once-in-a-lifetime offer to get some cash, to build the business full-time, and having a lot of support and belief in my abilities was what converted me and started helping me feel a little more open to the idea.

What kind of challenges did you have along the way, and when did you know when to pivot?

Alana and I wanted to build a big business. We wanted it to serve not just a couple of hundred small businesses. We want it to serve thousands. And when we were running our retail stores, We were only able to work with 120 brands at a given time because we had square footage limitations.

We had like a 3,500 waitlist that we just couldn’t do anything with, because it would be too expensive to open 30 stores to serve them all. So that was a big challenge, realizing that in 2018 and being like “We want to do more than just run three stores at once.”

We don’t really have the unit economics or the capital to go open more stores and tap into this waitlist. That was part of why we decided to build our own wholesale marketplace. We launched it in September of 2019, and it just started working right away. We obviously had to make changes to the team, changes to our policies and changes to our value system. We turned into a completely different business within less than a year, so that was a lot to juggle.

I definitely made mistakes. I know Alana feels the same way. Learning how to manage and managing [others] at the same time is very interesting and definitely challenging because you’re constantly second-guessing yourself. You’re constantly worrying about how your team perceives you. I think that’s something very unique to women, especially.

Related: The 5 Greatest Obstacles to Success — and How to Crush Them

You talk a little bit about your struggles in your upcoming book, How to Build a Goddamn Empire. You also talked about how you want it to help founders and especially women redefine the word success with every chapter. When did you first feel like you were successful?

I still don’t feel that way. I think that’s the problem. I think that a lot of what writing the book was a process of trying to find my sense of success in putting pen to paper. It’s not like I got this book deal, felt successful, and felt so accomplished with Bulletin.

Day to day, I don’t wake up feeling like I’ve made it or I’m the best or I’m super successful. So I guess I need to take my own advice. I do really feel like the experience of writing the book was like “Wow. I’ve had a lot of tough conversations with employees. I’ve come a long way as a manager. Alana and my relationship has come a long way as co-founders. We raised $10 million in venture financing when only 2% of women even get venture financing — I’m in the 2% of something.”

It’s not just about hitting a certain revenue number, a certain number of Instagram followers, getting verified on Instagram, working with a certain influencer or getting a certain piece of press. Those things are great, but building something from nothing should be just as much about the journey and the learning experience and the growth that you go through as a person, as it is about the business growing and hitting certain metrics.

How do you build a goddamn empire?

When I say “How to build a goddamn empire,” what I really mean is — if you have that itch to launch a side hustle, pursue an interesting project, or just build something for yourself, that’s your empire right there.

The ingredients for building an empire, however, big or small, require a lot of grit. Things are gonna go wrong. You’re going to make mistakes. You’re going to run into roadblocks.

The second ingredient is a really great support system. I personally experienced going from a six figure salary as a sales executive to the following year, drawing no salary and running outdoor pop-up markets on a shoestring budget in Williamsburg with decrepit port-a-potties and tents falling apart.

It was really hard for me to look around and see that a lot of my friends were leveling up in their careers. They were getting new titles. They were starting to save money. And I felt like I was going backwards. But I felt like I was going backwards because I didn’t really have a sisterhood of other builders and hustlers and people using that grit to just keep going around me the time.

Those are just a few key ingredients. The most important ones would be grit and resilience, a great support system and product market fit.

For women who do want to get into entrepreneurship, but may be intimidated by the space, what advice would you have?

Take the pressure off. When I think back on my and Alana’s journey, the reason I agreed to be her editor in chief for the ecommerce newsletter was not because I was like “Oh my god, how am I going to build like a multi-million dollar business in a few years?” I just thought, “Is this going to be fun for me? Will I learn something? Do I want to work with this person? Will I learn from her?”

If you’re thinking about starting a side hustle or becoming an entrepreneur or becoming owner, there are things to feel stressed and pressure about. There’s a responsible and a resourceful way to do it. But if you’re experiencing a psychological block that is intimidating you out of it or telling you that you don’t have what it takes, that’s where I think women especially need to relieve the pressure.

This doesn’t need to be something that gets written on your grave when you die. If you have the hunch and the inclination and the itch to do it, take a few baby steps and see how you feel.

Don’t feel like it needs to be this magnum opus, because that pressure is going to prevent you from taking those initial baby steps and just getting started.

Related: Entrepreneurship Is All About Overcoming Obstacles

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