Adam Schwartz On Selling A Company For $40+ Million And Now Building An AI Tool To Help Organizations Manage Their Time Efficiently

In today’s founder spotlight, we’re joined by a rare breed, Adam Schwartz, who has lived the full startup cycle, not once but multiple times, and has done so on his own terms. He is a founder who went from building scrappy marketplaces to scaling a profitable, venture-free company.

Adam’s latest venture, Parable, has secured investment from founder-operators: the minds behind HubSpot, Ramp, Vimeo, Superhuman, Squarespace, and more.

In this episode, you will learn:

• Startups live or die by product-market fit. Validating both sides of a marketplace early is advisable.
• Bootstrapping forces operational discipline and clarity on what actually drives growth.
• Profitability can be a competitive edge, especially when your competitors are burning cash.
• Marketplaces thrive when you obsess over supply–build for creators, and customers will follow.
• Exits are smoother when you’re not under pressure–build a business that doesn’t need to sell.
• There’s a massive data gap in how organizations understand themselves. Parable aims to close it.
• Venture capital is a tool, not a rule–use it only when the opportunity and model demand it.

 

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About Adam Schwartz:

Connect with Adam Schwartz:

• LinkedIn
• Crunchbase
• PitchBook
• TheOrg

Read the Full Transcription of the Interview:

Alejandro Cremades: All right. Hello, everyone, and welcome to the DealMaker Show. Today, we have a really awesome founder joining us—a founder who has gone through the full cycle, and quite successfully. Today, we’re also going to be talking about his latest chapter—his latest company. We’re going to dive into building, scaling, financing, exiting, and also talk about AI—how it’s going to change work, how work works, and how adoption is happening within the enterprise as well.

So brace yourself for a very inspiring conversation. And without further ado, let’s welcome our guest today, Adam Schwartz. Welcome to the show.

Adam Schwartz: Thank you so much. It’s great to be here. I’m excited to speak with you.

Alejandro Cremades: Originally born right outside of Boston—give us a walk down memory lane. How was life growing up for you?

Adam Schwartz: Yeah. My family is all native New Yorkers, but I grew up outside of Boston because there’s this famous loop called the 128 loop, where all the biotech and high-tech companies have their headquarters. My dad was part of the earliest wave of semiconductors in the 70s and 80s, and that’s how he ended up there. So I grew up with all this technology in my backyard.

Alejandro Cremades: And eventually, you went to Florida, and then from there you came to New York City. How did you start to get your feet wet in the venture world? Because back then, the whole startup ecosystem in New York wasn’t really that developed.

Adam Schwartz: Yeah, this was around 2008. My older brother, who was a couple of years older than me, was already in New York working for a startup. That startup probably had the first co-working space in New York. It was called AngelSoft, which was kind of like what AngelList is now.

There was also an organization called the New York Tech Meetup. If you know meetup.com, the founder of that platform created the New York Tech Meetup as its first group. You could basically fit the entire New York tech ecosystem in one room—maybe a couple hundred people.

I was 23, and I didn’t really know what I was going to do, but I always had an itch to be an entrepreneur. That always felt resonant to me, though I didn’t know how to do it. I walked into this room, and everybody was building something on the Internet. It was infectious and really inspiring. I knew I had found my community—my people.

I was really lucky to be there at that time. The community was so small that you could talk to anyone, and everyone would help you. A lot of the people who were in that room have now built multi-billion dollar companies or some of the most successful venture funds out there. It all started with that nucleus. There was a lot of cooperative and collaborative energy that I got swept up in.

Alejandro Cremades: That was back in 2009, which is when you also built your first company, Le Souq. As they say, you either succeed or you learn—and there was a lot of learning with Le Souq.

So tell us, what happened there and what were some of the lessons you took with you?

Adam Schwartz: Yeah. I think I was 24 when we started that company. Over the next two or three years, I got a complete education in all the ways you can go wrong.

To set the table: we were an e-commerce marketplace where fashion brands and designers could source sustainable textiles from suppliers. We were trying to connect supply with demand—specifically, textile suppliers with buyers.

Funnily enough, my family had a background in textiles. My grandfather was in the textile business in New York in the 1940s, walking down the same street where our office later was, selling textiles. We built the company out of an old textile mill that had been converted into a loft. It all happened kind of organically.

What we found was that the supply side—textile suppliers—wasn’t really ready to change how they worked to conform to a digital marketplace model. At least back then—and probably still now—it’s a very relationship-driven business.

We didn’t validate that enough. The demand was real; the problem we were solving was real. There was pain. But the stakeholders weren’t willing to change—or we weren’t able to get them to. We also had misalignment among the co-founders about how to respond to market feedback and whether to iterate or pivot.

That was also my first experience product managing and running an engineering team—triaging, roadmapping, and allocating resources to build product. I did 100% of the sales motion on both the supply and demand sides, so I got a crash course in go-to-market.

On fundraising—we had raised a seed round, and then tried to raise more without much traction. So across all pillars of early-stage business, we essentially missed. But I got a rapid education in how difficult it is to find product-market fit, how to build from scratch in those early, fragile years, and how to de-risk that process.

It was extremely informative.

Alejandro Cremades: No kidding. One door closes, and another opens—and in this case, it opened with a bang. You crossed paths with Josh Abramson, who’s also been on the show. Some people might know him as the founder behind Vimeo.

How did you guys connect?

Adam Schwartz: We were introduced while I was looking for my next thing. It was through a mutual friend I’d met at the New York Tech Meetup.

Josh told me he had sold Vimeo, CollegeHumor, and Busted Tees to IAC. He wanted to buy Busted Tees back—it was a profitable, cash-flow-generative business he thought had a lot of potential. He was looking for a partner to help him run it.

We really clicked on the idea of building a profitable internet-based business. At the time—this was 2011—even the good tech companies often didn’t have revenue, let alone profit. The concept of profitability was almost foreign. But we were both energized by the potential.

We looked at the business almost like a private equity play—it hadn’t been well-run. He managed to finagle it out of IAC, and we took over.

Over the next few years, it was really about fine-tuning every aspect of the business. We were profitable, had a small team of about 10 people, and I was personally optimizing everything—from customer acquisition to the web product to the supply chain—to grow margins and revenue. We ended up doubling the business.

But it became clear the model wasn’t scalable. By 2013, LivingSocial, Groupon, and Gilt were in vogue, flooding the market with unprofitable ads. They were spending 80 cents on the dollar to acquire a customer. Meanwhile, we were trying to do it profitably. It was obvious we couldn’t compete or scale under those conditions.

More fundamentally, Busted Tees was a DTC retail brand. It didn’t have network effects or the properties of a digital product—it was just retail with digital distribution. That realization led me to reflect on what a real internet business was, especially in the Web 2.0 world.

In that model, a great internet business is participatory and community-based. It empowers users to contribute. Vimeo was a great example of that—it was successful because it was a platform that enabled creativity from others. Busted Tees was creative, but the creativity came solely from us.

So out of that came the idea for TeePublic—a marketplace for independent designers and artists. They could build their own version of Busted Tees, design their products, and we’d host it on an aggregated marketplace, handling the supply chain.

While running Busted Tees, we came across new printing technology that allowed you to print one-off items—like a single T-shirt or art print—without taking on inventory risk. That, paired with digital content, felt extremely powerful.

But honestly, it sounds more strategic in retrospect—it was really just an experiment. We put in a little of our own money, tested the hypothesis, and brought on a small community of designers.

And the rest is kind of history. The business grew every month for probably 10 years. And crucially, we grew it profitably.

We never raised venture capital or debt. We were profitable every quarter for the entire life of the business. It was designed to be a profitable business—you had a digital product and a zero-inventory supply chain. A perfect retail business, essentially.

By the time we sold it, we had probably 100 times more SKUs than Walmart—an enormous volume of content on the platform.

Alejandro Cremades: What would you say was your biggest lesson around scale?

Adam Schwartz: Two things come to mind. First, we figured out our North Star early on. Through the data—and it’s kind of a known marketplace dynamic—we realized that marketplaces tend to be supply-side driven.

We were able to correlate designer uploads (our supply side) with the demand side—organic traffic, SEO, paid search. Once we saw that more supply led to more demand in a flywheel effect, we could forecast how much supply we needed to hit certain demand milestones.

Adam Schwartz: And then we became convicted and deployed, you know, for the next three years, I would say, nearly 100% of our resources into growing the supply side of the marketplace—nearly ignoring the demand side—because we were just completely convinced that we needed to take care of the artist side.

Adam Schwartz: We believed that if we did that, the customers would follow. And we were rewarded for that conviction, because that was ultimately how the model really worked. So we were voracious—very deliberate—about aggregating supply.

Adam Schwartz: Whereas our competitors, I think, were more focused on the demand side and on the customer side, which is natural. And that actually benefited us, because we were the most supply-side-driven company in the competitive set we were in.

Alejandro Cremades: Now, in this case, what was it like going through the acquisition? Because I’m sure it was quite nerve-wracking as a first-time experience.

Adam Schwartz: Yeah. Well, I think the first thing that was great about being a non-venture-backed company—and a profitable one at that—was that Josh and I didn’t feel pressure to sell the business.

Adam Schwartz: There was no gun to our head. We were having a good time, and the business was in a good position. So the acquisition was opportunistic—we weren’t looking for it.

Adam Schwartz: It came looking for us. And we only did it when we became convinced that this would be a really healthy outcome for us and for the future of the business.

Adam Schwartz: As the reality of that neared, it did become very nerve-wracking and stressful because it felt like your whole life was condensed into six weeks of diligence and uncertainty.

Adam Schwartz: But I think we probably had a better experience than some. As I said, if it didn’t work out, we still had a good cash-flow business. We were okay.

Adam Schwartz: After the acquisition, there was a huge adjustment period. Josh left, and I stayed with the business for another three years.

Adam Schwartz: We had to learn how to operate within a public company ecosystem, in a foreign market—Australia—and work with a public board.

Adam Schwartz: I had no board before that. I had no investors. Now I had public company investors and a public board of governance.

Adam Schwartz: It was a complete 180. But it started off as a really good experience. What helped was that the business grew a lot during that time. The acquisition was a big success. It helped the broader company a lot. And when everybody’s winning, I think life is easier.

Alejandro Cremades: Well, I mean, winning a $40 million-plus transaction without outside investors is quite the success, Adam. So good stuff. Now, obviously, once an entrepreneur, always an entrepreneur. Let’s talk about your latest company—Parable. How did the idea come knocking? Because at that point, you were spending time on different boards and doing more strategic-level work.

Alejandro Cremades: How did you start to come across the problem, and why did you decide to take action?

Adam Schwartz: Yeah. So when I was post-acquisition with TeePublic, one of the things I did during that time was look across the two organizations to understand how they were the same and how they were different. That led to some transformation work focused on efficiency.

Adam Schwartz: Somewhat serendipitously, after I left, I started doing board work. All of the board work I took on involved companies undergoing transformation—big structural changes.

Adam Schwartz: My reflection from all of that was that when it comes to company transformation—which is typically about organizational design, resource allocation, and operational planning—there’s a severe data gap.

Adam Schwartz: At TeePublic, we fine-tuned every dollar. That goes back to the story I was telling about Busted Tees. At TeePublic, we had deep data on the relationship between content acquisition and demand. We invested heavily in understanding the life cycle of an artist and a customer. I had hundreds of data points on each one.

Adam Schwartz: But by the time we were post-acquisition—with about 600 people—and in the companies where I was doing board work, there was essentially no telemetry data to understand what was going on inside these companies.

Adam Schwartz: In the 20th century, people used to say, “I know 50% of my advertising budget works, I just don’t know which 50.” Nobody says that anymore because digital advertising closed that gap.

Adam Schwartz: But when it comes to people and operations, we know more about our customers than we know about our own employees and companies. That data gap struck me as a severe inhibitor to a company’s ability to create alignment and efficiency in executing its strategy.

Adam Schwartz: When I first started experimenting with large language models, my co-founders and I started thinking about where AI could be used to make sense of fragmented, unstructured data—because that’s essentially what operational data is.

Adam Schwartz: Operations happen across hundreds of software tools. It’s all unstructured. Most of it happens in language form.

Adam Schwartz: We thought about how AI could be used to decode and distill that complexity into something insightful—so that organizations could start to reconceive of themselves in an AI-driven future.

Adam Schwartz: And that’s really the genesis of where the idea for Parable came from.

Alejandro Cremades: For those listening, how do you guys make money at Parable? What’s the business model?

Adam Schwartz: Yeah. Parable is an enterprise software business. Essentially, we work with large enterprises as the foundational system for AI transformation.

Adam Schwartz: We create a baseline of how an organization is currently spending its collective time. So we ask: what is your organization today?

Adam Schwartz: Based on that diagnostic, we identify how the organization can be transformed and made more efficient through AI.

Adam Schwartz: Then we implement that transformation. And because we established a baseline, we can measure the impact AI had on the organization—or even traditional transformation efforts.

Adam Schwartz: This creates a continuous improvement loop—a virtuous cycle. You can reconstitute a company around a new, more aligned and efficient way of working.

Alejandro Cremades: In that case, how did you think about VC versus non-VC? What was the thought process?

Adam Schwartz: As I mentioned, with TeePublic, we had a strong thesis against using venture. I still give the same advice to someone going into retail: retail businesses are poor candidates for venture. I think that’s been proven out by many of the retail venture deals from a decade ago.

Adam Schwartz: Parable, however, is an enterprise AI business—a cutting-edge tech company. It’s a perfect venture candidate.

Adam Schwartz: Venture capital isn’t inherently good or bad—it’s a tool. It’s either applicable or not, depending on the business model.

Adam Schwartz: What we’re doing at Parable is ideal for venture. We believe the market size is between $500 billion and $1 trillion.

Adam Schwartz: We need to hire the best AI engineers in the country. We need to build a product and go-to-market motion that delivers for Fortune 500 companies.

Adam Schwartz: So to pursue an opportunity of that scale, we need venture support. And we’re lucky to have it.

Adam Schwartz: I think having real telemetry data around operations is a universal problem. Every enterprise—and even smaller businesses—face it.

Adam Schwartz: To go after a problem of that magnitude and solve it through product, you need venture capital. And we’re fortunate to have that backing.

Alejandro Cremades: How much have you raised to date, and what was that journey like? I imagine that after your earlier success, it wasn’t too hard to raise.

Adam Schwartz: We raised in mid-2024—so not too long ago. We raised $5.2 million in our pre-seed.

Adam Schwartz: We very intentionally raised that round almost exclusively from founders and operators. Some funds participated, but all of them were created by founder-operators.

Adam Schwartz: We have the founders of HubSpot, Ramp, Vimeo (of course), Superhuman, early Squarespace and Gainsight executives, Bombas—the list goes on.

Adam Schwartz: We wanted a group of champions who knew what it meant to build a company. And we were fortunate to assemble that group in the round.

Alejandro Cremades: So Adam, let’s say you go to sleep tonight and you wake up in a world where the future of Parable is fully realized. What does that future look like?

Adam Schwartz: I think that looks like a world where we’ve built a digital twin and a data structure on top of organizations—or even governments and healthcare systems.

Adam Schwartz: These entities can then speak to their data in natural language. They can say, “I need to hit a certain budget and achieve specific OPEX and EBIT targets. But I don’t want to mortgage the future of this organization. I need to build toward strategic pillars that set us up for success.”

Adam Schwartz: Based on real data and real work, I want the system to simulate thousands of versions of my organization—in terms of design, resource allocation, and operational processes—and tell me what the optimal options are.

Adam Schwartz: Then, give me a plan to move from point A to point B. And eventually, I want a group of agents to help me execute that plan.

Alejandro Cremades: I love it. Now that we’re talking about the future, I want to go back to the past—with a lens of reflection. Let’s say I bring you back to the Tech Meetup days—when founders were throwing iPads and breaking them on stage. I was probably in the same room with you back then.

Alejandro Cremades: Let’s say you had your younger self sitting next to you during those early startup days in New York. What’s one piece of advice you’d whisper to him before launching a business, and why?

Adam Schwartz: I think I would tell him to think as big as absolutely possible—and not to shy away from that.

Adam Schwartz: In approaching and tackling the biggest problem you can find, everyone is going to build their business in a different way. There’s no exact playbook.

Adam Schwartz: While it’s important to study the masters and understand the frameworks, you also have to build with some amount of intuition. And that’s okay.

Adam Schwartz: Eventually, you’ll need to trust yourself to go after it and to make the right decisions. If you’re building with integrity, that will happen.

Alejandro Cremades: I love it. Adam, for the people listening who’d love to reach out and say hi, what’s the best way to do so?

Adam Schwartz: You can find us at askparable.com, and you can email me at ad**@as********.com. I’m happy to chat.

Alejandro Cremades: Amazing. Well, Adam, thank you so much for being on the DealMaker Show today. It has been an absolute honor to have you with us.

Adam Schwartz: The pleasure is mine. Thank you so much for having me.

*****

If you like the show, make sure that you hit that subscribe button. If you can leave a review as well, that would be fantastic. And if you got any value either from this episode or from the show itself, share it with a friend. Perhaps they will also appreciate it. Also, remember, if you need any help, whether it is with your fundraising efforts or with selling your business, you can reach me at al*******@pa**************.com

 

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