How to pitch, how to pivot and How to Build a Goddamn Empire with Ali Kriegsman

Today I’m chatting with Ali Kriegsman, Co-Founder of the YC backed tech startup, Bulletin.

Bulletin is a premium, B2B wholesale marketplace where retailers and buyers go to discover, shop and support the best brands on the planet. So this episode is highly relevant to anyone listening in who has a product based business and wants to work with cool retailers to sell their products and reach new audiences.

We’re chatting about the humbles origins of Bulletin starting as as e-comm newsletter and how that grew into popups, retail stores and went on to be accepted into Y-Combinator which lead to a major pivot into a thriving tech platform... we’re talking about Ali’s top 3 pointers if you want to pitch for VC money and - important to note she just released a really bloody cool book about her journey and you should absolutely check it out, I have linked it in the show notes and it’s called How to build a goddamn empire.

Please note, this transcript has been copy pasted without the lovely touch of a human editor. Please expect some typos!

Speaker1: I'm super excited. I always love to start by getting you to introduce yourself and tell us a little bit about what your business actually is.

Speaker3: So I'm Ali Kriegsman. Great to meet everyone. I'm the co-founder and CEO of Bulletin. Bulletin is a premium wholesale marketplace where retailers come to discover, support and shop the best brands on the planet. Think of it like a twenty four seven always on online trade show. And for brands we make it super easy, affordable and fast to expand your distribution channel. So if you're a product based business, you're making jewelry, candles, pantry items, whatever it may be. If you're looking to sell into physical retailers in the US and Canada or even online retailers that don't have brick and mortar locations, you can join Bulletin's marketplace, get up and running in just a few days and start selling nationwide and in Canada, which is super cool. I'm also the author of How to Build a Goddamn Empire. It is a no B.S. book on entrepreneurship. It's about my journey building, scaling and pivoting bulletin over the past few years. It also features thirty other women business owners that are building companies of varying stages and sizes. And the message of the book is pretty simple. I really believe that if you've decided to build something from nothing and you're in the trenches, that makes you successful enough, that's a really big commitment to be making every day. And I think women especially often shortchange themselves and don't give themselves enough credit. But it obviously gives tactical advice and a ton of storytelling around tackling imposter syndrome, figuring out what areas of your business to invest in and which to abandon. And we obviously get stories and failures and mistakes and triumphs from these incredible other business owners as well. Not just my story.

Speaker1: I cannot wait to read it. That sounds so cool. And I'm really excited about this conversation because obviously we have a lot of small business owners and brand owners listening into the show who would be highly relevant for the platform. So for everyone listening, you should absolutely jump online immediately and check this out because it's going to be right up your alley. And it's so much fun, no pun intended. Actually, it wasn't intended, but now it is. Now that I've heard it, we

Speaker3: Can say that it was intended. Oh, my goodness.

Speaker1: All right, let's get started. Where does your entrepreneurial story actually start?

Speaker3: It starts at age twenty three, twenty four, I had entrepreneur parents growing up and it was a very feast or famine lifestyle and it was a super tumultuous upbringing. My dad also had a lot of medical crises and emergencies. My family went through a ton of financial hardship in my late teens, early 20s, and for that reason I kind of crossed entrepreneurship off my list. I was like, find me the most stable job in the world. Like, give me a doctor, give me a lawyer, let me be a consultant and I'll be happy. Lo and behold, I ended up kicking my career off at Condé Nast, which is a very massive publishing company, a legacy brand. I ended up leaving to join a startup called Contently, and I was just really bored. I was in sales. I was giving the same drab, dry sales pitch every single day, you know, making the same joke planted at the exact same moment of the pitch days on end. And I was the number one salesperson for quarters and quarters. I'm really good at it. But I wasn't fulfilled. And my entrepreneurship journey started when my business partner and co-founder Alana turned to me issues a few years older than me. And she was like, I want to create a newsletter that shop, a bill that features like the coolest brands on Etsy. I'm like a lot of these kind of independent designers and makers that you'd have to dig through Etsy to find yourself.

Speaker3: And for me, it wasn't this big, like nose dive into entrepreneurship. It was definitely a slow build. I agreed to work with her on it. I was editor in chief of the Bulletin newsletter and I wrote all of the articles and the features and the interviews with these artists and designers, most of them based in New York. And it was just a way to, like, get on board and do something fulfilling and something creative. I've always loved to write. I fashion myself a writer, and it was just a side project to kind of tap into a part of me that wasn't being addressed by my full time job. And it took off from there. I mean, we did it as a side project and as a side hustle on the weekends and in the evenings for about a year and a half. We ended up getting a grant, a twenty thousand dollar grant to dive into the business head first and go full time. And I was twenty four. It kind of seems like now we're never I was extremely scared, extremely anxious again, just kind of anchoring my experience against the anxiety and the tumultuousness. I grew up with having entrepreneur parents, but it felt like I had really regret it if I didn't take the chance. So that's that's where it all started.

Speaker1: Oh my gosh. It's come a long way. I'm interested to know in that beginning phase of that first year and a half while you were kind of doing it on the weekends, it was the side hustle. How many subscribers did you have and was it making any money at that point? And what was kind of like the the thought about what you'd grow it into at that point?

Speaker3: So when we first started the way that we did customer acquisition because we had no money to do ads or anything on like Facebook, Instagram, Google, you name it, it was fully bootstrapped. We emailed everyone we knew in their mother. It was like, OK, let me blast this. So like every listserv I was on in college, we emailed it to everyone. That was at our current full time job at the startup we worked at. And we were like spread this far and wide. We did a few, like low key partnerships with other New York based companies that we felt had overlapping audiences. I was our press person. I've been our press person from the beginning and helped get us placed in places like BuzzFeed and Refinery29. So I would say like press, I'm just really leveraging our own network and kind of shamelessly like broadcasting bulletin to everyone we knew was the way we built up our first subscriber base. I think that initially in the first few weeks, we grew it to about five hundred subscribers. I want to say by the time we started doing our pop up markets, which was the next evolution of the business, we had maybe ten thousand. And a lot of that was driven by press at the time. Like, I really think media now has become so much more oversaturated. We're like BuzzFeed and Refinery29 are publishing like 50 articles a day, whereas back then it was in twenty, fifteen, twenty sixteen, you know, they were maybe doing five to ten. And so I think press was really instrumental for us at that point.

Speaker3: And then we started doing pop up events pretty soon into the business. We did our first series of pop ups at the end of twenty fifteen. And so those in-person experiences got us actual customers and we pushed those emails into our newsletter and we were making money by the time we applied to the grant that we eventually got, I want to say we were doing like six thousand dollars or so monthly in revenue, which wasn't crazy, but it was a Squarespace site and it was dropship. We didn't own any of the inventory. We were taking a 40 percent commission on everything that sold. So it was a profitable business. It wasn't like the most lucrative thing on the planet, but part of why we ended up pivoting and making pop up markets a core part of our business model by the end of twenty, fifteen, early twenty sixteen was because we weren't making enough money. So by the beginning of twenty sixteen, we started our series called Bulletin Market. We did pop up markets all over Brooklyn and Manhattan and we charged brands anywhere from one hundred and fifty dollars a weekend to four hundred dollars a weekend, depending on what part of the market they showcased in. We bought all the tents and tables and set the whole environment up for brands, so all they had to do was come and merchandise their table, which made us competitive with other pop up market series like Smorgasbord or Long Island Flea, where you have to schlep everything yourself.

Speaker1: Sounds like hard work.

Speaker3: It was really hard work. We were working seven days a week, but when we turned that on, it was still bootstrapped and we were making like fifteen thousand dollars a weekend sometimes depending on how many brands and food trucks we had showcasing. So we definitely I mean, as a woman in business and I think with like a venture scalable business on Alana's mind, my co-founders at the very least, at the beginning, we knew that in order to get an investor time of day or get on their radar or have a fighting chance at raising venture capital as a women owned business, we needed revenue. Women can't really get by with just having a massive user base or a massive customer base or certain press hits or a waitlist. In my experience, women get measured by their proven track record, whereas men get measured by their potential. So early on in the business, the goal was just like make more money, make more money, make more money versus make this more scalable. And by the end of twenty sixteen was when we really realized that we didn't just need to be optimizing for profits, we needed to be optimizing for scale as well. And that's when we opened our first set of Pop-Up stores.

Speaker1: Right. OK, got it. What I'm interested to know is like how did you go from pop up stores and pop up markets to getting into Y, C? And for anyone who doesn't know, what I see is why C is Y Combinator. And it's kind of like a tech accelerator, right? That it's, you know, the people who have brought out things like Airbnb and and it's the people who have fostered

Speaker3: Dropbox, Dauda,

Speaker1: Shackley let it super, super tech focused businesses. So how does one go from pop up markets and a pop up store to tech accelerator and like the best tech accelerator in the world?

Speaker3: It's a really good question. So we the grants that I mentioned was through Y Combinator, so a few years ago, Y Combinator had two programs that they were accepting applications for, but they didn't make it known that there were these two programs. So we were applying to every incubator accelerator known to man, every grant program known to man, because we just wanted money for the business. And we ended up not getting into Y Combinator core program, but we ended up getting into this program called Y Combinator Fellowship, which doesn't exist anymore. They only did it two or three times, but the program was for super, super early stage companies that were too early for the core batch program and in exchange for a very minor amount of equity, they would give you twenty thousand dollars. And the stipulation was, you have to work on this full time. The program is three months. Let's see how this goes. So we were already in the Y Combinator ecosystem with our e-commerce newsletter because of Y Combinator fellowship. They only accepted like 20 or so people to fellowship. And so by the time we had scaled the pop up market, by the time we had opened our first retail as a service store in Williamsburg, we had been rejected by Y Combinator batch program two times like we just kept applying and kept applying.

Speaker3: And the way that we finally positioned the business and what got us in was positioning bulletin as the way we work or Airbnb of retail space. We believed at the time that it should be just as easy to take over physical space and physical retail space and showcase your wares as a brand as it is to launch a Facebook ad or push a Facebook or marketing campaign out on Instagram. So we our whole thesis was taking over physical space is going to become programmatic, the same way that running ads on Instagram or Facebook is programmatic. And so we basically built a technology platform. It was super nascent where brands could like people stop and pick their spot in the pop up market and then in the store. And honestly, just like piggybacking on the success of Airbnb and we work and kind of bundling our brick and mortar based business as a tech enabled physical retail tech company was what got us in. Do I think that Fullarton should have gone through? I see with that business model, I don't know.

Speaker3: I mean, now that we run a true wholesale marketplace technology company, I feel like I learned the lesson that scaling physical space is not the same as scaling software. But I think that we see at the time was very interested in the future of retail. They were kind of looking to penetrate this industry that they had it historically invested in. And I think we were two compelling female founders. I think they were also trying to bring more female founders into their ecosystem. And we had a lot of revenue. I mean, by the time we got into Y Combinator, we were doing like sixty five thousand seventy thousand dollars in recurring revenue every month. So even though we didn't have, I think, the nuts and bolts of a true tech company at that time, we were more like a tech enabled brick and mortar based business or real estate business. I think they were really impressed with our vision and with our traction. And I think that we had proven ourselves to a point where they were like, well, this may not be the end all be all idea, but these founders are onto something and we want to see where this goes.

Speaker1: You know what's funny is that actually the first time I came across you and your co-founder was because I was going through the application process for what I see myself it was last year, I think it was. And I was. You found

Speaker3: The YouTube

Speaker1: Video? I found the YouTube video. And I was reviewing female founders who had been through I. Sadir to look for look for clues and look for hints of what what could stand out. So that's when I first got introduced to the brand and was like, oh, this is so cool. Love that for you. Thank you. At some point, you pivot and you switch to completely just the tech like marketplace. Mm hmm. I know that a lot of tech founders have this struggle of like the chicken and the egg onboarding like two sides of the coin. What was it like for you? And did you have that struggle that tech founders do often have?

Speaker3: The reason that we pivoted into the wholesale marketplace was I would say there were a few contributing factors. As I said, we were this tech enabled real estate company. At the end of the day, like much like we work was. And we all know how that panned out. And I think for me and Alana, even though the stores were independently profitable and even though we had built this really beloved and compelling consumer brand that was this unapologetic, you know, metropolitan female skewing persona, it was really clear to us that the venture path made no sense. Again, you can't scale physical space and physical retail like you can scale software. It costs too much money. And so when Alana and I projected out operating more than three stores, the model just broke. It didn't make any sense. And our business was also a very heavy service based business, because if a brand wasn't performing well in the store, you need an account manager to manage it. That relationship to keep retention up. Whereas with software it's like you have customer service, but there isn't as much like handholding and customer maintenance. And we also had a wait list of almost four thousand brands, but we were only able to work with like one hundred twenty brands at once because we only have three spaces.

Speaker1: So it was this

Speaker3: Realization of like there's this massive pent up demand that we're not able to serve with this current execution or version of our business model. The appetite for brands to access retail space without having to pay ten thousand dollars to do a trade show, without having to sign up in the showroom for six months, without having to pay a wholesale rep for three consecutive months, without knowing if they're going to close business for you. That was why we had this massive waitlist, but we weren't solving any of those problems. If the only answer was pay to be in one of our three stores, we're full. We only have one hundred twenty spots and it's too expensive to open more stores. So that's when we realized how we can connect brands with other retailers. Why do we have to be the retailer? Why don't we connect a brand with another like minded retailer? Why don't we connect a retailer with all of these incredible businesses on our waitlist? So to answer your question of was it hard like this chicken or the egg thing of getting the marketplace up and running? Oddly enough, no. I think that because we had done pop up markets for so many years and we had worked with, like. I want to say over a thousand brands at that point. We pinged our brand network and we were like, we're launching our own wholesale marketplace, like sign up here, and I want to say of the first 100 or so brands we sent it to, like sixty five signed up immediately.

Speaker3: And so for us, scaling supply was really easy because of the journey we had already been on, which this is why I'm all about. Turn failure into something else, like I can look back on the store business, the pop ups of the newsletter, and be like, oh shit, that was like such a mess up. Like we were just like swimming in this, you know, unscalable, like problematic business for so many years. Building a two sided marketplace is nearly impossible, like I just did it, and the fact that we were able to leverage that past experience to get brands on the site so quickly was a lifesaver. I really believe it's like the only reason that this worked the hardest part was scaling demand. I mean, the hardest part was like tapping into this new customer. Retailers we had never talked to before, never targeted before, didn't really understand their pain points or their concerns. We were retailers ourselves, so that helped. But that was definitely harder, I think, because of our journey as a business, getting to the wholesale marketplace, running stores, running pop ups, running newsletters, and having this massive brand community already under our belt, we knew that we could get supply on board really quickly and that's where we focused our efforts first.

Speaker1: Got it. Gosh, that's so interesting. And I also feel like had you not have done the pop ups and done all of that, it would have been such a different story. Launching something like that. You would have launched two crickets, essentially. Exactly. So all of that foundational work. Yes, it was a pivot. And yes, you didn't see it. The vision immediately from the get go of what it could be. But it was 100 percent on the right track, obviously.

Speaker3: Right. I feel like the insights were always correct, like Alana. And my insights from the very beginning were always correct. But the execution was incorrect. And frankly, I think that going through Y Combinator, seeing other tech businesses that scaled really quickly and efficiently and kind of being in their shadow gave us this amazing educational experience and learning opportunity to be like, oh, that's what we have to do. But I will say and this is why I think parts of venture capital are so broken. We work was a beacon of light and billions when we were building the retail as a service model in the stores and like if you Google Bulletin, you'll see so many headlines. It's like we work with retail, we work retail. So Adam Newman's, you know, great trade, directly informed our business model. And so it's interesting because it's like we almost picked the wrong tech company to model ourselves after and to build in the shadow of for a few years. And once we kind of replaced, like, push them off our vision board and put Etsi on our vision board and Airbnb and be on our vision board and kind of really anchored against true tech companies. That's when things just fundamentally changed for us. But it's watching all the we work documentary stuff and reading all of the content and reading the book about we work is such a triggering experience for me because I'm like, God damn it.

Speaker3: Like we saw the way that Adam Newman and we work, we're being propped up. And we were like, oh, we're going to do that for retail. That's going to be us. And it was definitely a very big decision at the end of twenty eighteen because that was before the we were reckoning happened to see the writing on the wall and kind of push back against what the venture capital landscape was saying, which was like we work is going to be a multibillion dollar company saw things investing. We had to put our own microscope over their business model and be like this makes no sense. But it's hard to do that as female founders in the tech space where you've been deferring to your investors and just kind of deferring to the landscape for so long because you're new to it and you don't know any better. It was a big leap of faith and moment of believing in ourselves to like look at the company we had been modeling ourselves after for so long and be like this, saying it like this. If we keep doing this, this is going to break us. And like that company is like going to implode.

Speaker1: Yes. Oh, my gosh, that is so crazy. I yeah, we work. It's such a tough one, isn't it.

Speaker2: Hey, it's down here. I'm just popping in to bring you a quick message in every episode of the show, you'll hear women who would just like you trying to figure it all out and hustle to grow that business. And I know a lot of you might be sitting there asking yourself, but how do I actually scale my revenue an