✍️ ALI KRIEGSMAN // BRAND CONSULTANT & FORMER FOUNDER

0:00I'm Sam Rose, and this is Commerce is Chaos, the podcast for consumer brand founders who know that building a business is messier than the highlight reel shows. Your supplier just missed their deadline, your top product is out of stock, and your competitors somehow just launched the same thing at half the price. Sound familiar? Every week, we dive into the real problems that keep founders up at night, from inventory disasters to supply chain nightmares, because surviving the chaos is what separates brands

0:25Ali Kriegsman:that fail from brands that scale. Okay. Thank you and welcome to Commerce is Chaos. It's been a minute since I recorded an episode, so I'm so happy to have you here and to be kicking off this next season with such an amazing guest. So thank you for taking your time. I know you're super duper busy. I am a lucky gal. Thank you for having me. And I got the prep questions and I'm very excited for this conversation, I will say. Amazing. Okay, well, let's get right into it. So you built Bulletin, which was a wholesale marketplace. I was a customer. You were so young, by the way. I also started a business very young.

1:05How that can go for you?

1:07Ali Kriegsman:A child. Yeah, I don't know what I was thinking, but I also feel like I wouldn't have done it unless I was that kind of naive and optimistic and just like open road ahead. It was great. I mean, I think what was so beautiful about starting a company that young is like, you can really tell yourself if all else fails, I'll just go back to X, right? I was like the number one salesperson at the tech company where I worked. And I told myself, if this doesn't happen, like if we don't hit certain KPIs or we don't see a certain amount of momentum here, I'll just go back to enterprise sales. So in that way, it was a very freeing time to take that risk.

1:53Ali Kriegsman:but I don't know what your experience was like starting your business young, but I definitely think from an emotional regulation standpoint was not fully baked. So a lot of the highs and lows of entrepreneurship, the anxiety, like the imposter syndrome, the negative self-talk, you know, I just hadn't been in the ring for long enough to know how to properly manage some of those inevitabilities. So yeah, it made it easy to take risks, but like quite difficult to deal with some of the volatility of the entrepreneurial journey. You know, now that you're saying that, I remember feeling all of those things.

2:36Ali Kriegsman:Yeah. Yeah. Yeah. I feel older now and more durable. Definitely. You know, I have like more emotional fortitude. But I remember at the time taking so many things so personally, like I really just, I was like selling spatula, but I took it so personally and I really felt like I was, you know, like fighting, fighting for something better cookware. Um, and, and yeah, I would get hurt kind of easily. Like if we lost, I hated to lose. Um, and at the time I'm like, this is good. I'm taking it personally. That means I'm going to like, you know, commit and invest and like not give up. Um, but I think if I if I was my current self, you know, putting my arm around my little self, I would say like, you know, it's it's not I mean, make it a big deal if you need to make it a big deal.

3:25But like, don't take it too personally.

3:27Ali Kriegsman:Yeah. And like, you'll you'll get through it. And I think just being able to still like enjoy your nights or enjoy your weekends and not have it dictate your entire mood. Yeah, I really cozied up to the anxiety of the entire experience. And I think now it would it would be so different. So, so different. Yeah, I can. I'm better at compartmentalizing now than I was. Although we're in a story for a beer or another conversation. We're in a little bit of a scrap with with a counterparty, I'll say. And it was my daughter's ninth birthday the other day. And like I just got the most disruptive email, like right before, you know, cake time.

4:11And I just I just was right back in it, you know, just like, oh, yeah, I have to respond to this right now. And I got a customer that's upset and the whole thing and stuff like that still gets me.

4:22Ali Kriegsman:Well, that's yeah, that's the nature of the beast. But it's it's it's what we sign up for, you know, the the high highs and the low lows and like the getting the crappy email before the celebration. And the learning to emotionally regulate in those moments is something I wish I could like put in a pill and gift to founders in their 20s. I just wish that I had learned that so much sooner. You know what? Even if it was a placebo, that would be really cool. Yeah. Yeah. Just let me think that I'm doing it. All right. Bye, guys. Allie and I are starting business. Yeah. Off we go. Off we go. Oh, man.

5:04What would we call it? All right. Well, we'll talk about that later, too. But I do think, yeah, just some sort of placebo pill for like it can have magnesium in it or something that made you call actually ashwagandha. But the rapper is just like, chill the fuck out. Yeah.

5:20Ali Kriegsman:You will survive. It's just a company. Right. It's just business. OK, so you so you're building Bulletin. You sell it. You sell the Emerald. Great exit. I mean, and also congratulations. That probably transformed your life, no doubt. It did in some ways. I mean, I think for me, Alana and I were so scrappy. And I was just telling someone this over the weekend. Like, we definitely, especially as Bulletin grew, we understood how important it was to have the right people on the team. And so we would, like shrink our salaries so we could keep certain people on the team. Like when, you know, the business needed us to do that, like COVID was obviously very tough.

6:06Ali Kriegsman:So there were some years I was making 45K, you know, some years I was making a hundred K salary as a founder, but it was seven and a half years of really just crossing your fingers and hoping and praying through hard work every day that there's like a financial light at the end of the tunnel. and for me there was. It is interesting though like you know we sold for 10 million we raised a bit under that it's not like the watershed exit that our investors may have wanted and it's not like a watershed exit that gets a lot of press but I work hard to contextualize it and be like I started that company at 24 I did not come from a technology background you know pivoted three to four times and just fought tooth and nail to stay alive and to build something that was accretive and something that like actually drove value for our customers and drove value for in the market and had market relevance.

7:07Ali Kriegsman:And so to actually get there on the other side of what felt like such a torturous, like confusing seven and a half years of like trying to make that happen, I'm super proud of it. And everyone on the team got jobs. Some people on the team made a bit of money from the exit. You know, some later investors did did OK. So it's it's just funny, though, how like you can say like, oh, I sold a company for 10 million dollars. And to, you know, the average person that doesn't know about VC, they're like, that's crazy. And then to you know, 10 million dollars yeah well not that um but then to like someone in venture capital they're like and so what you know they're like your investors must be pissed at you so yeah you have to you have to find your own um definition of success so so true so so true i mean which goes back to the first thing we were saying just like you have to kind of really become durable as a person to survive survive the journey.

8:07And, and I mean, to make sacrifices like that along the way of just like, you know, trading your own salary to like create a job for somebody else or maintain a job for somebody else. So they don't tell you this, like you're going to be doing that. And then, you know, you're looking at, I don't know, payroll's got to run and you look at it and you're like, okay, oh, I still want to be here. So I just, I just, I just, I just, yeah, you're moving numbers around

8:34Ali Kriegsman:And you're like, I don't know how long this kind of shrinkage is going to be the case for me. But you have to delude yourself into, you know, there's a pot of gold at the end of this rainbow. And you don't know how big it's going to be. But I'm very glad that we stuck it out. That said, you know, I think every founder wants to quit multiple times. And so I'm very grateful to Alana, my co-founder, who was worlds more resilient than I was and who was definitely the voice being like, keep it together. Like we're staying in the game. It's going to be OK. Yeah. Yeah. She was like the roots of our tree a thousand percent.

9:21Ali Kriegsman:Yeah. Yeah. It's so valuable to have someone like that that can just be, especially if it's a friend, like be in the mix with you and just understand the full context of what you're going through without having to have it filtered or storylined or altered. And you get the most positive and critical feedback in that way. Yeah. And I don't just mean feedback like, hey, here's how you're doing. but like as a literal feedback loop, almost like a neural feedback loop. Yeah. How am I going to regulate? Yeah. No, I credit her immensely to a lot of learning how to regulate and just having her as a partner, as a friend, as a role model, you know, leading with her.

10:03Ali Kriegsman:It was one of, it's been one of the defining experiences of my career in the best way. Oh, I love that. That's actually really beautiful. thank you um take us through like the next chapter so you you sell and uh and since then you've been doing like some incredible stuff i mean and maybe like maybe stuff that no one would have predicted either yeah will you tell us what you're working on now yes i went a little bit rogue Um, but listen, I think like in the, in the context of me, myself and I, like when I think of my story, it makes a lot of sense to me. Um, you know, I think building a B2B business and for me, I ran all things growth.

10:51Ali Kriegsman:Um, and I eventually replaced myself with a CRO as the business matured, but I'm a very creative person. You know, I did all of our, you know, brand voice and comms and PR and marketing and social because for a long time before we pivoted to B2B, you know, getting the consumer's attention and investment in our stores, you know, when we had stores like and our online business, like that was how we grew. When we decided to do the wholesale marketplace, I had to learn a completely new set of skills. I had to learn, I had to go back to enterprise sales, basically, which is where I started my career.

11:33Ali Kriegsman:I had to learn performance marketing. I had to learn referral loops. It was just a whole new experience for me that was not, it was creative in the sense that it was very strategic and very problem-solvey. But, you know, there's no colors. There's no storytelling. You know, at a certain point, it does become a bit rinse and repeat. And so after the exit, I wrote a fiction book. I had started writing the book while we were building the business just as like a little creative outlet because, as I said, so much of that creativity had gotten sapped from my day-to-day roll at Bulletin. And I launched it myself in 2025.

12:15Ali Kriegsman:That's a lot of what I did last year. I brought it to market myself. I made a really innovative movie style trailer to promote the book as a way to kind of break through the noise. Like every market is so saturated right now. Like how do you make people pay attention to your book? And I wanted to build a visual world. You know, I did a lot of innovative stuff on TikTok. Hold on one second. My boyfriend's just coming home. Hey, boyfriend. I'm on a podcast, honey. Do you mind just like dealing with shrimp's barking? Thank you. Okay, I can pick it up. He's like not a barky. He's like a not a barky dog, but he always says hi when his dad comes.

12:58Yeah, but then he knows when you're busy. And so he's like, exactly.

13:01Ali Kriegsman:Yeah. So yeah, I did a ton of innovative stuff on TikTok. I did these like POV style videos where I had actors like cosplaying as characters in the book. And I did like this cool editorial shoot with actors playing the characters to bring the characters to life. I did a really thoughtful gifting campaign. And so just kind of taking my years of brand building and go to market and applying it to my own product, in which case, you know, this fictional world and this story that I had written. And what I've also been doing is I specifically help brands grow with Bulletin. It was helping them increase their distribution, getting into retail stores all over the U.S.

13:46Ali Kriegsman:and Canada. And I continued to do that for a while. I helped, you know, one brand create a relationship with Ulta, for example. And so, you know, helping other brands like figure out their independent retail strategy. But I really started to notice that the new retailer is the influencer. You know, a lot of influencers through affiliate platforms like ShopMy, which is my expertise, are driving crazy D2C revenue for these brands. And so I decided to become an expert on that new retailer, which is, you know, the affiliate seller, the influencer, and help brands build programs that kind of activate that new area of distribution.

14:29Ali Kriegsman:So I've been doing that for the last year and a half. And that was sparked by before working on my book, one of my clients approached me and was like, I think we should be doing Shop My. Here's what it is. You know, take over this platform. We don't know what we're doing. Can you figure it out? And that's a founder's dream, right? To kind of get under the hood of a software that you don't understand, figure out all the secrets, figure out how it works, figure out all the mechanics. And I drove such great results for them that I figured, OK, I can do this for other businesses. So, yeah, I kind of have two parallel paths going.

15:04Ali Kriegsman:I'm still trying to build out my career as an author. I'm working on my next book. I have a sub stack that is, you know, thankfully growing every day. and then I'm still helping brands grow, but I'm trying to keep up with the times. You know, I think retail is still really important, but I'm always looking at like, what are the new tools and new systems and new partners brands are using to expand? And I need to become an expert in those if I want to stay in the game. And I'm always trying to stay in the game. It's never over. I mean, you got to build a goddamn empire, you know? Exactly, exactly.

15:41Ali Kriegsman:And I want to, you know, I'm like, okay, I sold the first one for 10 million. I started it when I was 24. I had no idea what I was doing. I don't know that I'm ready yet to build a full-fledged, you know, business again with a team. But I really believe in learning in the in-between so that once I get the bug again, I have a thesis. I have a point of view. You know, I have deep experience in what marketing is, what brands need, kind of like what's going on in my space so that I can activate again when the time comes and be like, okay, you know, what can I do now? What can the outcome look like now?

16:20I mean, it's so interesting that you say that too, because, you know, there's, I think there's a sort of Silicon Valley trope of like, you know, you get the degree and then you decide you want to be in tech and then you like look for a problem and, or you engineer, like you engineer like a like a solution in search of a problem and uh my personal version of entrepreneurship has always been so much more spontaneous like I combust with an idea because I'm experiencing some pain or some problem like so excruciatingly myself and like I'm a really good you know I'm a fertile ground for that sort of thing yeah I guess um and uh and and waiting, I think what I want to tug on that you're pointing at is that sometimes that requires extraordinary patience, because otherwise you're just going to start, you know, a solution in search of the problem.

17:14And if you wait for a problem to be so precise and so strongly felt that you're like, okay, no, this, this is a thing worth spending my, you know, single finite resource on earth, which is time, like we're absolutely finite resource, uh, worth spending my time on, then the, the outcome will be better in, you know, on every vector. It'll fulfill you more. It'll have more commercial success. It'll be easier to find customers for and, and the whole bit. And I always kind of worry for folks who are like, you know, want to have urgency in that process. Like do have urgency. If you want to start something, start something, but, but you can't necessarily just cast about for like the idea.

17:59It's got to kind of hit you in like, you know? Yeah.

18:03Ali Kriegsman:And I, and I think too, like there's definitely cachet around building a business and being a founder. Um, but I think that the, you know, again, bulletin pivoted multiple times until we really found our sweet spot. And I can totally own that. Like when I was that young, I didn't feel quite right in someone else's startup environment. I felt really disillusioned by like, I don't know. I was like, okay, these founders can raise and do this. Like, why can't I? Like kind of empowered by what I was seeing. I didn't feel good in a big bloated corporate environment. I had started my career at Condé Nast.

18:44Ali Kriegsman:I didn't feel quite right there. And I can totally own now that in my early 20s, when I started my first business, the impulse was not, oh, there's a problem here that I need to solve. It was more, oh, maybe this identity and spending my time this way will feel more aligned. And there's a reason Bulletin had to pivot multiple times. It's because we weren't, well, I don't want to speak for Alana, but I don't, it's because there wasn't what you're saying. There wasn't that kind of like massive pull around there's this customer, they have this pain, we need to solve this pain. It was more self-focused, at least on my end.

19:24Ali Kriegsman:And so then you end up in the throes of building a business. Maybe you've taken on capital and you're sniffing your way toward product market fit. And you're not here somewhere. And it's, you're going to have to do that anyway. Like I do, you know, one chapter of my first book is like the business you start isn't the business you run. You will always evolve. You will change your business model. Like, you know, what YouTube is started out completely different than how it started. And there are so many stories of that. But yeah, I do think a good number of people start companies from a place of wanting to be a founder or wanting to like own more of their time versus there's this pain point, there's this problem.

20:10Ali Kriegsman:I have a POV or philosophy or conviction around how this can be addressed, how this can be solved. And I can't take it anymore. You know, I just have to start testing out my theses. That, yeah, I just got to start. Yeah. And I can't take it anymore. Yeah. Is, was there, is there anything that comes up for you in, in memories of like yourself operating right around that time when you kind of like made the last pivot and ultimately, you know, put Bulletin into kind of like it's, you know, the last chapter of what it became, like insights into, you know, the wholesale world, the B2B world, the trade show world.

20:51What was it for you that kind of came up as like a, oh, we got this now?

20:58I think that there's always, well, what I will say is this.

21:06Ali Kriegsman:I think Bulletin always really struggled with the tension between curation and scale. I think those things are always at odds with each other. And we always wanted to build a really compelling brand and a brand that had a point of view. A marketplace or like a software company is not supposed to like have a point of view. It's just supposed to serve as many people as humanly possible. Um, and I think once we let go a little bit more of being seen a certain way or having a certain amount of brand cachet, and we really focused on how do we get more people using this, because that's what makes the supply and demand side of a marketplace valuable.

21:53Ali Kriegsman:Um, that's when we started to grow like crazy. I mean, there was a specific moment in 2021 where I replaced myself with Rachel Krug, our CRO, and I kind of handed off like a theory of the case to her where I was like, these are a lot of things we haven't done that I think we should try. These are the things I think are hamstringing our growth right now. Here's why we haven't done them. You know, you're an expert that's done this before. She had come from an exited marketplace business. I was like, if you can make the case for doing these things, let's see what happens. And we did them. And within three months, the company just exploded.

22:37Ali Kriegsman:Like our GMV was above and beyond what I had ever gotten us to. And I think part of it was like really just accepting what you need to do to make the mechanics of your specific business work. And if that's a marketplace, You need an aggressive amount of supply. You need an aggressive amount of demand. You can handle merchandising and this curation experience through, you know, filters and tooling and collections and like things within the assortment. But you shouldn't be capping the brands that can join your marketplace because they don't have the right aesthetic, right? It's like, how do you bring them on?

23:14Ali Kriegsman:And then how do you bring the right buyers on where maybe that aesthetic is totally right for them? How do you build tools within the marketplace so that they can find each other? And I think that just becoming more technologically savvy, really thinking more about like recommendation systems within the platform, thinking about merchandising and like thinking about how we can solve this user experience around curation within the experience of the marketplace versus how we're capping supply and demand. changing that just completely yeah made made the business grow really significantly in a short period huge unlock I mean yeah actually and what a cool insight like I don't think I've ever framed it in that way either like the tension between curation and scale being like you kind of have to pick at some point you do retrofit the right you know retrofit what in your case you you know unlock the scale piece and you've got to retrofit and build for how the brand promise.