447: Aditude: From Scrappy Consulting to 7-Figure SaaS - with Jared Siegal

Summary

Episode 447: Attitude: From Scrappy Consulting to 7-Figure SaaS with Jared Siegel

Podcast Information:

• Title: The SaaS Podcast - SaaS, Startups, Growth Hacking & Entrepreneurship
• Host: Omar Khan
• Guest: Jared Siegel, Founder and CEO of Attitude
• Release Date: June 12, 2025

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Introduction

In this compelling episode of The SaaS Podcast, host Omar Khan sits down with Jared Siegel, the visionary founder and CEO of Attitude—a monetization platform designed to help digital publishers maximize their ad revenue. Jared shares his transformative journey from managing a scrappy consulting business to building Attitude into a high seven-figure SaaS enterprise. The conversation delves deep into the strategies, challenges, and insights that propelled Attitude's rapid growth and success.

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Background: From Publishing to Consulting

Jared Siegel's roots in the online publishing industry span nearly 15 years. His career began at a publisher in St. Louis, where he met his wife and witnessed the company's meteoric rise—from revenue of a few million to a quarter of a billion dollars in just two years. This experience culminated in the company's sale to a private equity firm for nearly $1 billion, a success that paradoxically left Jared feeling empty-handed. Twice experiencing similar outcomes—where his contributions as an employee didn't translate into personal gains—Jared was motivated to chart his own path.

Jared Siegel [04:50]: "I helped two companies basically raise one and sell for a lot of money. And I personally walked away with almost nothing. So once I saw that starting to happen a second time, I made sure that I kind of protected myself and moved on."

Determined to control his destiny, Jared transitioned into consultancy, offering his expertise to publishers grappling with monetization and ad tech challenges. This phase laid the foundation for his later ventures by building trust and a robust client base.

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Building Attitude: The Pivot to SaaS

In early 2019, while running his consulting business, Jared faced acquisition offers from two companies eager to buy his consultancy. However, wary of repeating past disappointments, he opted to decline and instead pivot towards creating his own SaaS product. This bold decision marked the inception of Attitude.

Jared Siegel [07:59]: "I have no idea what that really means. I want to try it out."

Jared collaborated with an engineer from one of his clients to develop the first version of Attitude. Recognizing the importance of trust and proof of value, he chose to offer the product to his existing clients for free initially. This strategy not only demonstrated the platform's efficacy but also seamlessly transitioned these clients into paying SaaS customers once the product proved its worth.

Jared Siegel [16:04]: "All of them [clients] agreed and just switched over. ... By February of '21, everyone was converted and we were scaling up the business."

Within four months of switching to the SaaS model, Attitude achieved its first million in annual recurring revenue (ARR). The consulting arm continued to support the SaaS development, providing essential bootstrap funding that fueled further growth without external investment.

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Challenges of Bootstrapping: Balancing Control and Growth

Bootstrapping Attitude presented Jared with significant challenges, particularly in managing finances and personnel. Operating as a bootstrapped business meant that every dollar spent directly impacted his personal finances.

Jared Siegel [21:30]: "I own 98% of the company. So every dollar that the company was spending meant a dollar out of my own pocket."

Jared's meticulous approach to financial management involved scrutinizing every expense, leading to intense debates within the executive team about scaling versus maintaining profitability. The stress of these decisions was a constant pressure point, ultimately culminating in the decision to raise a Series A round to propel the company forward.

Jared Siegel [24:19]: "I literally couldn't make up my mind that I wanted to do it."

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Fundraising: Strategic Outreach and Leveraging Profitability

When the time came to seek external funding, Jared leveraged the profitability and trust he had built within his business. He adopted a strategic approach to fundraising by targeting venture capital firms that had a productive investment history in his industry.

Jared Siegel [29:25]: "I only sent maybe seven or eight out and all of them replied pretty much within like 24 hours."

Jared's candid and bold outreach emails emphasized his business's profitability and the strategic advantages of partnering with him, rather than merely seeking financial support. This approach not only garnered immediate responses but also positioned him favorably in negotiations, ensuring a successful Series A raise of $15 million in August 2023.

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Growth Strategies: Referral Engines and Event Hosting

A cornerstone of Attitude's growth was its reliance on referrals and organically built networks, especially in the early years before implementing formal marketing strategies. Jared fostered a culture of client referrals by incentivizing existing customers to introduce new clients in exchange for free consulting hours.

Jared Siegel [32:45]: "I built this massive network of people selling Attitude and I never had to do any sales. Deals were just kind of lucky, but they were just like literally falling onto my plate."

In 2023, Jared introduced innovative event-based strategies to further expand Attitude's reach. By hosting exclusive events at Disney World—integrating his personal passions with business objectives—he created memorable experiences that resonated with clients and prospects alike. These events not only strengthened existing relationships but also attracted high-profile clients and sponsors, significantly enhancing brand visibility.

Jared Siegel [37:05]: "We took them to Animal Kingdom, into Epcot and to two rounds of golf. Four dinners, boat cruises and all this kind of stuff."

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Scaling the Business: Leadership and Delegation

As Attitude grew, Jared faced the critical challenge of transitioning from a hands-on founder to a strategic leader. Initially, he managed nearly every aspect of the business, from coding to invoicing, driven by a desire for perfection and control.

Jared Siegel [43:06]: "I was doing all invoicing, payroll, making sure that we were established in each state for tax reasons... 99%, but maybe 75% of the workload."

Recognizing the unsustainable nature of this model, Jared invested in professional management training and gradually began delegating responsibilities. A pivotal moment came when he took a vacation and returned to find the business thriving in his absence, validating his trust in his team.

Jared Siegel [46:53]: "And so we, and we organized and threw it all ourselves, right? It became big enough that I actually became a travel agent on the side just to throw these events for us."

This shift allowed Jared to focus on strategic growth, innovation, and leadership, ultimately enabling Attitude to scale efficiently while maintaining operational excellence.

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Leadership Insights and Personal Reflections

Throughout the conversation, Jared imparts valuable leadership lessons and personal insights that have been instrumental in Attitude's success:

• Revenue-Driven Mindset: Emphasizing the importance of being a revenue driver rather than a cost center has been a guiding principle.

  Jared Siegel [48:29]: "Always be a revenue driver, not a cost driver."

• Understanding the Business: A successful founder possesses a deep understanding of every facet of their business, ensuring they can navigate any challenge that arises.

  Jared Siegel [49:07]: "Someone that spends the time understanding each aspect of the business."

• Routine and Productivity: Jared's disciplined daily routine minimizes decision fatigue and maximizes productivity, a practice he likens to raising a child.

  Jared Siegel [49:41]: "Same way, like we're raising our child. She has the exact same routine every day and it helps her not be cranky and stuff like that."

• Personal Motivation: Diagnosed with multiple sclerosis at a young age, Jared channels his personal challenges into driving relentless productivity and commitment to his business and team.

  Jared Siegel [51:28]: "I'm a very motivated, type A person with a very specific timeline. There's a very specific reason why."

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Conclusion: A Testament to Resilience and Innovation

Jared Siegel's journey with Attitude is a powerful testament to the virtues of resilience, strategic pivoting, and the unwavering commitment to building something of one's own. From rejecting lucrative acquisition offers to bootstrapping through stringent financial discipline, and finally scaling through strategic fundraising and innovative growth strategies, Attitude's story is both inspiring and instructive for aspiring SaaS entrepreneurs.

Attitude today stands as a high seven-figure SaaS business with approximately 50 employees, handling over 100 billion ad impressions monthly. Jared's leadership and innovative mindset continue to drive the company's success, making Attitude a prominent player in the ad tech monetization space.

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Notable Quotes:

• Jared Siegel [04:50]: "I have no idea what that really means. I want to try it out."

• Jared Siegel [16:04]: "All of them [clients] agreed and just switched over. ... By February of '21, everyone was converted and we were scaling up the business."

• Jared Siegel [21:30]: "I own 98% of the company. So every dollar that the company was spending meant a dollar out of my own pocket."

• Jared Siegel [24:19]: "I literally couldn't make up my mind that I wanted to do it."

• Jared Siegel [29:25]: "I only sent maybe seven or eight out and all of them replied pretty much within like 24 hours."

• Jared Siegel [37:05]: "We took them to Animal Kingdom, into Epcot and to two rounds of golf. Four dinners, boat cruises and all this kind of stuff."

• Jared Siegel [48:29]: "Always be a revenue driver, not a cost driver."

• Jared Siegel [49:07]: "Someone that spends the time understanding each aspect of the business."

• Jared Siegel [51:28]: "I'm a very motivated, type A person with a very specific timeline. There's a very specific reason why."

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For more information about Attitude and to connect with Jared Siegel, visit jaredtitude.com.

Transcript

[Jared Siegel]

Foreign.

[Omar Khan]

Welcome to another episode of the SaaS podcast. I'm your host, Omar Khan, and this is a show where I interview proven founders and industry experts who share their stories, strategies, and insights to help you build, launch, and grow your SaaS business. In this episode, I took to Jared Siegel, the founder and CEO of Attitude, a monetization platform that helps digital publishers maximize their ad revenue. Back in 2019, Jared was running a scrappy consulting business, helping publishers fix their broken ad tech. He'd write raw JavaScript in a text editor, email it to the clients, and ask them to paste their code into their websites. It was totally unscalable, but it worked. Then something interesting happened. Several companies came knocking with pretty attractive acquisition offers. But Jared had been burned before. Twice he'd helped build valuable companies as an employee, only to walk away empty handed when they sold. So he turned them down and decided to build something of his own. No venture capital, no team. Just Jared and a borrowed engineer from one of his clients. Together, they built the first version of what would become Attitude. Now, here's the brilliant part. Instead of charging for it, he gave it away free to his consulting clients. Once the product proved it could help them make real money, he flipped the switch to a SaaS model and converted all 30 clients overnight. Four months later, attitude hit its first million in annual recurring revenue. But that's when the real challenge began. Jared had hired a team, but was still doing everything himself. Code releases, payroll, invoicing, taxes. Not because no one else could handle it, but because he was convinced he could do it better. It took his wife literally forcing him to take a vacation for him to realize the truth. The business kept growing while he was completely offline. And that's when he finally started letting go. Today, Attitude is a high seven figure SaaS business with about 50 employees. They've raised $15 million and serve over 100 billion ad impressions every month. In this episode, you'll learn how Jared transformed a scrappy consulting gig into a fast growing SaaS company. Why giving away his product for free actually built more trust and made conversion easier. How consulting revenue became the perfect bootstrap funding for product development. We talk about what it really takes for a control obsessed founder to step back and scale out of the weeds. And how he built a referral engine that grew the business without any traditional sales or marketing. So I hope you enjoy it. All right, Jared, welcome to the show.

[Jared Siegel]

Yeah, thanks for having me.

[Omar Khan]

Do you have a favorite quote? Something that inspires or motivates you?

[Jared Siegel]

Sure. I'm a big country Music fan, big Luke Bryan fan. So in one of his songs, he says, do what you love, but call it work for me. Making sure that, like, I enjoy what I'm doing every day. I get personal satisfaction out of it is what you know. You know, it's important to me, and it's what keeps me motivated.

[Omar Khan]

Love it. Love it. So tell us about attitude. What does the product do? Who's it for? And what's the main problem you're helping to solve?

[Jared Siegel]

Sure. So we consider ourselves a, like an ad tech monetization platform. More easily put. We like to think of ourselves as the AWS for publishers. So we work with publishers, websites, any type of content creator, whether they're game sites, news sites, celebrity sites, we run the gamut and we help them with any of their needs as it relates to monetization. So that could be with reporting, that could be with literally serving the ads, video, whatever it may be.

[Omar Khan]

Okay, cool. And give us a sense of the size of the business. Where are you in terms of revenue, customers, size of team?

[Jared Siegel]

Yeah, we're about 50 employees. We do about 100 billion ad impressions on our platform a month, and we're in the high seven figures a year in ARR.

[Omar Khan]

Cool. And I think you've raised like around 15 million for your series A. Yeah.

[Jared Siegel]

We did series A in August 2023 for 15 million.

[Omar Khan]

Great. And before all the people who are bootstrapping go, oh, yeah, he got the money. You actually went to the first 5 million in ARR. You bootstrapped to that point before you raised any money, right?

[Jared Siegel]

Correct. Yeah, we ran the business for about four years. Completely bootstrapped. I funded the whole thing.

[Omar Khan]

Cool. Awesome. So let's talk about, like, you know, your background and what were you doing? How did this idea sort of come about?

[Jared Siegel]

So my personal background, I've been in online publishing for almost 15 years. But before attitude, always on the publisher side. So I worked at a publisher out in St. Louis where I met my wife. And that company, you know, it was employee number 30. It was doing a few million a year in revenue. Two years later, we were doing like quarter of a billion dollars in revenue. I was running the revenue team, and the company sold to a private equity firm for almost $1 billion. It was a whirlwind. I learned a lot very quickly, as, as happens with many companies that eventually sell, big turnover in the leadership team. I left, went to another publisher, started doing the same thing, literally just helping them monetize, serve ads on their website. As they expanded the business into other lines, they started raising more capital. And I, I think I had a, maybe a similar experience or, or motivation to a lot of founders, which was I helped two companies basically raise one sell for a lot of money. And I personally walked away with almost nothing. And so once I saw that starting to happen a second time, I made sure that I kind of protected myself and moved on. And like, hey, I'm going to start my own business purely to control my own destiny.

[Omar Khan]

Right. So you quit your job and you started consulting.

[Jared Siegel]

Yeah, it was a little bit of like an impromptu decision to quit my job. I did not tell my wife no way. I went into work one day. I went into work with a two and a half hour train from Long island into the city. Got in early, sat down with a boss, asked for a raise. He said no. I said, cool, like, spur the moment. I quit, handed in my laptop, took the train home, called my wife and said, hey, I just quit my job. And she's like, what are you going to do? And I'm like, you know, I'll figure it out. So started out purely, hey, I'm just going to consult for, like, friends that I've met in the space, a lot of companies that were spinoffs of previous companies that I had worked at. And like, over time I'll figure out what I actually want to do in life. Right. I did, like, go to school for entrepreneurship, so I knew I always wanted to eventually start my own business, but, like, I had no, like, actual idea of what that business was going to be or what industry it would be in and what. And so I consulted by myself for about 12 months. I hired one other employee and he helped me for another 12 months. And I just ran it purely as, like an hourly consulting business. Send invoices monthly. This is how much I work, this is how much you owe me. And I scaled that business up.

[Omar Khan]

How. How big did that business get?

[Jared Siegel]

We grew it to, I think, around 30 clients and about 2 million in essentially net revenue a year.

[Omar Khan]

Cool. Okay, so you've got about these 30 clients. Where did the idea for SaaS business come from?

[Jared Siegel]

Yeah. So let me think about it. I started in early 2019. Towards the end of 2020, I. I had two companies out of blue offer to buy me. Right. Buy my company. Right. One was a video tech vendor and one was an actual ad exchange. And they just knew me because I was working with so many of their clients. Right. And I was kind of taken aback by that because I never, at that point, I didn't think I even had A company. I'm like, hey, I'm just consulting, right? I'm like, what do you mean you want to buy, Buy my business? He means you just want me to be an employee for you, right? And they threw out some numbers that were frankly, like they were life changing numbers. And maybe, you know, I'd say it's 2020, maybe I should have taken it, I don't know. But I, you know, I spoke with my wife, I called up one of my old professors from college who was working at like a senior partner at a VC firm and kind of went through the opportunities with him and he was basically like, hey, you're running a consultancy. Your valuation is as good as the revenue you're generating and that's it. So you have a decision to make. You can keep going down the same path and personally make a lot of money, but you're going to be doing this forever. Or you can pivot your company into a real business, maybe SaaS, right? And grow it much quicker and try to sell the business, right? And interesting enough, he's like, I think you should do the former and I want to buy you, right? And so now I got a third offer and I was like, all right, this is getting out of control. I'm going to do the second thing. I'm going to pivot to SaaS. I have no idea what that really means. I want to try it out. And that's when I like, I called up my best friend, I was like, hey, why don't you come on over, be our cto, help me build out real products. Because up to that point, any tech that we had built, I built in a TextEdit file. I'm not an engineer. I built in a TextEdit file and I was sending TextEdit files to our clients with just like raw JavaScript in it and saying like, hey, push this to your site. I don't even know what that means, but push this to your site. And so that call with that former professor, whether he realizes it or not, basically completely changed the path of my business.

[Omar Khan]

So, so you called, you called your best friend and said, come on, you can be the CTO. We're going to build this SaaS thing. I don't know exactly what that means, but that's what we're going to go and build.

[Jared Siegel]

Correct? But, but the, the most important thing to him I said was, right, he had a family at the time and it was a big risk joining a startup. I was like, hey, we're making a lot of money already. I can afford to Pay your salary, what do you want? Right? I'm like, let's do this together. I'm going to give you equity in the business. Let's try to sell this for, you know, crap ton of money one day. Let's do it. Right. And he said, okay. So a few weeks later he came, flew to my house, we sat down at my dining room table, we built the very first official version of what we call our cloud wrap or our main product, and we started pushing it out to the market.

[Omar Khan]

How did you figure out what to build? A lot of people are in this sort of position where they're running a services business and they want to get into SaaS. They're not really quite sure what to what the product should do, right? Because maybe, maybe as a services business, you're providing so much to clients.

[Jared Siegel]

And yeah, we were doing a lot of different things. Yeah, we were helping with analytics, we were helping them with like billing, we were helping them with monetization and optimizations. It was a very, I mean, I was fortunate, but it was a very clear answer to me. Okay. I was basically acting. I attitude was acting as a middleman between all of these publishers and several other third tech or third party tech providers that were doing what I now do, right? And I was basically getting paid to help these other companies fix their product, right? And to me, it was basically me saying, oh, this is like the exact same scenario I had with the two former employers I had. I'm doing all this work and I'm getting nothing for it, right? I'm helping them solve these issues on behalf of my clients. Why don't I just provide that service myself? Right? And so I went to one of our very first clients, said, hey, I'm gonna build this out. I'm not gonna charge you for it. Will you test it? Right. And if you test it, I want you to move all of your tech to me. And it was kind of wild. Cause this is actually before I hired my cto, he gave me his engineer for free for six weeks. We built it together because it behooved him if this worked, he was gonna save a lot of money, right? And we built out the very first version. It crushed, it did incredibly well. And I was like, awesome, this is what my business is going to do, right? At that point, I didn't change my business model, but now I was like, cool, this is what I'm going to focus on. This is the piece of tech. A lot of other things have come from that over the last five years, right? In terms of other features and products that we've built out. But it was, I was very fortunate that, like, a lot of my clients were dealing with the exact same issue with the exact same vendor. Right. I was like, cool, I'm just going to replace that vendor and do it myself.

[Omar Khan]

Wait, so many founders try to get, you know, if they're bootstrapping, they try to get customers to, if they can fund the development. So you went further and you actually got an engineer from a customer.

[Jared Siegel]

Yeah. So he gave him to me for six weeks. And eventually again, this is me as an individual employee, like one person company. Once it started to work, I said, hey, I want you to go tell all of your friends that are also working with this other vendor that they should switch to me. And I'm going to pay your engineer. He's going to work now for me, and he'll now support you on your stuff, but you're going to pay me for his work and I'm going to figure all of this out right now. He's my employee, not yours anymore. You know, thinking about this now, honestly, I don't think about this that often. It was a crazy situation. And he said, sure. He said, sure. So I got very lucky.

[Omar Khan]

You gotta have a good relationship with a client to be able to have that type of conversation.

[Jared Siegel]

Yeah. A lot of my early clients I had already known from previous jobs for quite a while, five, six, seven years. And some of those early clients, I mean, talk about like building a services business and building up a good relationship. I'm literally in their wills. Right. So, like, if anything happens to their business, it goes to me, which is wild. Not their family and things like that. Right. So these are people that trust me at the, at least at the time, trusted me enough.

[Omar Khan]

Are you serious?

[Jared Siegel]

Yeah. If something happens to me, please take care of my business and my family, which is honestly an honor. A little bit crazy. But I remember I have one, I have the very first message of a client that asked me to do that saved on my computer. So starts like, hey, this is a really weird question, you know, but would you be willing? Right. So, yeah, we, I, I built up very close relationships with these people because I was talking to them like six, seven, eight hours a day on hangouts and stuff like that. Right. And a lot of them were very similar businesses. So you know what worked for one, I could kind of multiply and apply to everyone else.

[Omar Khan]

Yeah. And not only that, you started going on vacation with all your clients. But we'll talk about that a bit in A minute. So you built this product, this, this initial one, and I think you said you had about 30 clients at the time. How many of them agreed to switch to the SaaS and start paying for it?

[Jared Siegel]

All of them. And this is the lesson that I learned there. I, for another six, seven months, I gave the tech away for free. I still did the hourly consulting model with all of them, right? And I got to the point where these businesses, like I was hosting their websites, I was running all of their ads, they got like, I mean, just smart, kind of create a sticky business model, right? But like I was as sticky as you get. Like these companies cease to exist without me at that point. And I was like, cool, I'm switching my business Smile now you're going to pay a little bit more. But this is why you should want to do that. We have real engineers now that I hired. You're no longer working with this guy that sometimes creates good code, sometimes breaks your website, right? We're going to constantly innovate and we're going to use that money to build new features for you that you've always wanted. Right? And so pretty much all of them right away agreed and just switched over a handful, said, hey, I want you to prove to me that you can make me more money to justify the increase in cost. So we did a handful of a B tests against ourself, right? Like my original free version of the code versus our new paid version of the code. And we had to prove that, look, the lift was more than the cost. But eventually we got there. So we released like, and pivoted to a SaaS model in November of 2020. By February of 21, everyone was converted and we were scaling up the business.

[Omar Khan]

So February 21st you convert, you give it away for free. Which often founders struggle with that because they're like either obviously there's pressure to generate revenue, but. And then you always hear the thing about charge for the product, the conventional wisdom. But in many ways if you're solving the problem with the product, they already trust you and you're not charging them for the tech, it kind of becomes a no brainer for them to start using it. Even if they know down the line. I mean, they're not stupid, right? They know down the line at some point there'll be some kind of, you know, they have to pay something for the software at some point.

[Jared Siegel]

Right, right. And I kind of made that clear. Them too, right? Like, hey, at some point I have no idea how I'm going to charge you or what I'M going to charge you, but at some point I'm going to charge you for this. Right. Because at some point I have to grow my business. I can't just keep growing everyone else's business. And mine is, you know, making no money. The other thing was like I used the consultancy part of the business to fund the tech, the SaaS business. Right. It was making enough money from all this ancillary stuff that I was doing for websites and these publishers that it could Easily fund hiring 3, 4, 5 engineers. Right. It could easily fund my own paycheck. Any investments in tech, you know, aws, whatever we needed to like invest in, there's plenty of cash around to do that. We, which is why I was like very hesitant for a while to stop that part of the business. And even to this day, you know, we're five, six years later, I guess six years later, the consultancy part of our business still exists. It's no longer, you know, 99% of the revenue, it's a smaller part. But there are still clients that, from way back in the day that still pay us hourly to do all these things for them so they don't have to deal with it.

[Omar Khan]

How long did it take you to, to get to the first million in ARR once you did start charging from.

[Jared Siegel]

A, from a SaaS revenue perspective, you know, sound a little bit ridiculous, maybe like four months. We got like, we were able to scale up our business to such a large size by giving it away for free that when we pivoted it was like almost instantaneous. Oh my God, look how much money we're making. Right. And so our first year of like pivoting from hourly to mostly SaaS, a little bit of hourly, we literally doubled our revenue. And so it was, it was a very quick ramp up. But again, like our consultancy, by the time we did this, it was a legitimate business. Right. Like we had enough clients where like we were one of the larger companies in our space, even though we didn't have any tech.

[Omar Khan]

Yeah. And the reality is that you wouldn't have been able to do that if you hadn't run the consulting business for a couple of years and solve their problems and built the trusts and all of that stuff. Right.

[Jared Siegel]

And had the funding to do this all.

[Omar Khan]

Yeah, yeah. And as we talked about earlier, you raised money when you were at the 5 million-ARR point and you were telling me it was like that was probably when we least needed the money. Talk to me a little bit about some of the challenges you had. Bootstrapping. So it's great. You've got this consulting revenue, and you're using it to fund the SaaS development. But what was the hard part of bootstrapping this business?

[Jared Siegel]

I think there's two things. There's the personnel part of it, and then there's the, like, the financial future decision making. Okay? So from a personnel perspective, when we were bootstrapping, by we bootstrapping, I was bootstrapping the business, right? I own 98% of the company. My wife owned the other 2%, right? So every dollar that the company was spending meant a dollar out of my own pocket, $1 less that we were taking home that year. As we kept scaling up the business, the amount of money I went from making a lot of money to making almost nothing, right? And, you know, so every decision we had to make, hey, we have to hire this another employee we need to hire. We need to pay for this piece of software for our developers. Hey, our AWS bill just went to $20,000 last month, whatever it may be, right? All of that was like, shit, this is money out of my own pocket, right? And so I. Even as we became more and more profitable, I ran this business as if every penny mattered. Like, I was in nickeling and diving. I would checked every bank statement every single day to review what was going on, and I questioned everything. And so there was definitely a lot of, like, say, heated debates is a polite way to put it. Between me, the other executives, and some of our employees. I'm like, hey, why? Like, why the heck do we even need to spend this money? Like, enough. Let's stop. Let's stop spending money. I just want to make, right? And the second part of that is like, okay, we are profitable. Like, where are we trying to take this? Because again, at the time, if we said, all right, we're good at 5 million, we don't need to grow anymore. Let's just run the business as is. I'm sure my other employees would love to hear this now, but that meant me and the two other executives could make a lot of money every year. We had no one that we were beholden to. We could write ourselves nice bonuses and say, hey, we have a really nice life. Let's do this for the next 10 years, right? And so that was always a hot debate between the three of us of should we keep doing that or should we shoot for the moon? Should we raise capital, take a little bit less now and hope that one day we walk away with a lot of money? And so that was kind of the biggest stress Point and what's the word I'm looking for? That's what impacted my decision the most. When we raised our Series A, we got the offer, I feel like in like February of 23, and I didn't close until August, and it had nothing to do with due diligence or anything, that kind of stuff. It was like I literally couldn't make up my mind that I wanted to do it.

[Omar Khan]

You didn't want to let go of the equity?

[Jared Siegel]

Yeah, I don't want to let go. I'm like, oh. Like I'm literally giving up a lot of my ownership in this business, right? I had my wife chirping in my ear as well, saying like, oh my God, like, what if this doesn't work? We just gave this all up, right? Plus the business was paying for everything personally, right? That's kind of what small businesses do. Everything's a business expense. And so it was a big decision. And every June, I always host a barbecue at my house. I invite a ton of employees over. They fly out from around the country, invite friends who are clients over. Some of those friends that have written me into their wills, right? And we host this barbecue. I cook, I love to cook. And, and we just hang out and have a good time. And at that barbecue in 2023, I just, I don't know if I had enough cocktails or whatever it was, but I sat down with the two other executives and I was like, guys, I think we're going to do it. I'm going to take the money. And they looked at me and they're like, let's go, let's do it. Right? And so once I finally made up my mind, then the due diligence and that whole process of raising capital started.

[Omar Khan]

You're generating 5 million ARR. At the time, there's no real pressure for capital. Like you said, it was like you didn't need the money at that point.

[Jared Siegel]

No, I think we had six employees. So you can kind of do the math of like how much we were taking home.

[Omar Khan]

So what was the driver that even got you reaching out to VCs?

[Jared Siegel]

Yeah, it's a good question. In the back of my mind, I always had this question of like, hey, how much am I worth? How much is this business worth? I'm curious. A little bit of curiosity and a little bit of like, what else am I not doing that I should be doing? What do I not know as a first time entrepreneur that I really need to know, right? And so when I did raise capital, this is a little Bit of a bold statement to say on all of, like, these VC calls that I have, but to every single one of them, I said, I don't need your money. What else are you going to give me, right? And the company that we ended up raising capital with had the best answer to that question. Let's.

[Omar Khan]

Let's talk a little bit more about that. Because you. We were talking about this earlier, and you said that when people ask you about raising money, you, you, you know, one of your first questions is like, are you profitable? Right? Just. Just explain that a little bit, because I completely agree with that.

[Jared Siegel]

So I know there's, like, I've had friends that, like, literally, hey, I have an idea. I'm going to raise a ton of money at a crazy valuation on this idea. I'm going to give up a ton of my ownership and hopes that I can actually make a business out of this. And what happens to most of those, right? Like, the traditional VC fund makes thousands of investments a year and 95% of them fail, right? You're going to end up in that bucket. To me, it was always like, hey, I want to get to a point where if I raise capital, me personally and my family, we're financially set. If something bad happens, I don't care. My employees are financially set at that point when we raise capital, I always said to my wife, hey, I'm not supporting us, right? I'm supporting all these other families and their children.

[Omar Khan]

No pressure.

[Jared Siegel]

Yeah, no pressure at all. But a lot of pressure, right? I definitely felt it at the time. But, you know, I have a lot of friends, and one of my best friends right now is starting a company or starting companies trying to raise capital. And it's the very first question I ask is, like, are you profitable? No. Well, then why are you raising capital, right? Like, why are you going to a VC firm? Why aren't you trying to take out a loan or a credit line or something to turn this business profitable? So when you do raise capital, one, you get the valuation you want. Two, you keep the, like, you don't dilute yourself to a point where, like, it's no longer worth it to you, right? And three, so you're in control of a negotiation. If you are profitable and you own it and you don't need the money, you can make whatever demands you want, right? They may say, no, you're crazy. That's fine. You don't need the money, right? When you are struggling and you need that check, because if you don't get that, you're Going to have to lay off your entire team and the company ceases to exist. They're going to beat you up on valuation. It's exactly like the show on Shark Tank, right? Like, oh, you're not profitable. Cool. Your valuation just fell 75%.

[Omar Khan]

Yeah, I would say like the further you can get bootstrapping, the more revenue you can generate, the more profitable you can get, the more leverage you're gonna have. Whenever it comes time to raise money and you as a first time founder, you then decide you're gonna raise money, you send like these cold emails to VCs. Most people might get a reply or two. You, how many of the, how many emails did you, how many VCs did you email and how many of them replied?

[Jared Siegel]

Yeah, I only, I only sent maybe seven or eight out and all of them replied pretty much within like 24 hours. And so again, this is like, as I talk to friends who are thinking about raising now, I have like a very specific strategy that I talk to them about, which is one, do your research on firms, whether they're VCs, you know, growth equity, angel investors, whoever it is that you're trying to go after. People who have invested in companies that are related to your company right in your space and have made money off of that. They've invested in a company and it's been a flop right in your space, they're not going to want to invest in you. They've been burned, right? So find a company that has made a productive investment in your industry. And then two, be really bold in your, in your outreach. Right? So my emails to everyone, I don't remember them exactly word for word, but it was like four or five sentences, something like, hi there, first time entrepreneur here, no idea what I'm doing. I've grown my business with no funding to $5 million in net revenue. Imagine what would happen if someone told me what I'm supposed to be doing.

[Omar Khan]

I love it.

[Jared Siegel]

And yeah, and every single one responded like, hey, we want to talk about. Right? And when they heard my story of how I, I pivoted and I use basically a consultancy business with one line of revenue to, to fund building out an actual tech company. They're like, hey, it's really smart. Right? At the time I was like, I wasn't really thinking of it that way. I was like, yeah, I guess it is really smart, but it was a very bold email. I didn't send like a bland like here's my pitch deck. I never sent any pitch decks, right? And frankly, when I presented to them. I maybe had like one or two slides, but it was mostly just me talking extemporaneously to them about my thoughts on the space, introducing them to some of our clients as well, to talk on our behalf. Probably very different than the average outreach that these firms experience. The other thing that I did as a small business is I didn't go after the Sequoias and these major companies right in the space that everyone wants to work with. They're cutting checks are hundreds of millions of dollars. They don't care about my little rinky dinky business. At the time, I went after firms that were smaller, 30, 40 people in the company. Right. They probably have a billion dollar total fund across their entire network and they do make these smaller investments. So I was very particular of who I reached out to. I found the right person, the person that made that previous investment in those firms and email that person directly. Right. And I was very like bold, but also like very blunt in my email. Right. And it worked.

[Omar Khan]

Yeah. And again, I think it goes back to your point about when you're looking to raise money, are you profitable? Because you could never write an email like that. When you're like, I've just built this product and I have no revenue or I have two customers or something like that.

[Jared Siegel]

You.

[Omar Khan]

It's a completely different type of conversation that you're having. Let's. Apart from converting the existing clients from the consulting business to SaaS, how else did you acquire customers and grow until.

[Jared Siegel]

I think like literally mid 2024. So for five years, we never had any marketing or any sales. It was just me. And it was all like, I kind of built it in a way where like, it was kind of the cool club. Right? Like, you only got to work with us if you knew someone that knew me. Right. And so all of our business came through referrals, all of it. Whether it was an ad exchange that I became friends with, that wanted to integrate with a publisher that couldn't do it, they would make the referral or one of my existing clients would make the referral. And so for many years I had like a policy, I don't know, like a plan with my clients. That base said for every publisher that you get, that you introduce me to that converts, you get three hours free. That was it. It was three hours free. And we had a few clients that just went nuts and they're like, I'm going to introduce you to everyone I know so I don't have to pay for the next six months. And I was like, awesome. I could care less. Let's do it. Right? And so I basically built this massive network of people selling attitude and I never had to do any sales. So like, deals were just kind of lucky, but they were just like literally falling onto my plate. And I was in a position where I could say, hey, this deal doesn't make sense. Sorry, I don't think we should work together. Like, absolutely. This is what I'm going to do for you and let's get going. The other thing that I did, and I mentioned this to you before, but that I think is interesting, is historically speaking, we no longer do this. But as I was building the business and I needed to fund it, everything was paid in advance. You always paid one month ahead of time, right? I was never sending invoices for March in April, right? On March 1st, I sent you the invoice for the entire month of March guessing what you owed me. Any difference, positive or negative, was credited or applied to the next invoice. Right. And that way I never had like aging receipts and things like that, right? Like, I literally never had a balance sheet where people owed me money. I was always ahead on everything.

[Omar Khan]

Did you ever get any pushback from that? Because when you start dealing with some companies and more bureaucracy, they're like, oh, we have this policy on how we pay and accounts payable does this and.

[Jared Siegel]

So on some of the larger publishers, and I'm talking about companies that you, every one of your listeners, has probably interacted with versus some of these smaller shops, right? They definitely pushed back on me on that. And I basically said, if you want to work with me, that's the deal, right? I'm not willing to negotiate and I won. In most cases, they're like, fine, I guess we have no choice, right? I was a little bit stubborn, but like, I'm literally not willing to negotiate with you on any of my terms. This is it. I have this contract signed with all my other clients. You got no choice, you got to sign it.

[Omar Khan]

Why? Why do you think you were able to do that? So obviously you're, you're solving an important problem and you, you have a track record, you got these clients and so on. But like, was there like, did you have much competition? Was there like other places they could go to?

[Jared Siegel]

Yeah, and it still is, frankly. There still is. This is a pretty like online advertising, it's a quasi trillion dollar industry, right? There's a ton of companies in this space, including the behemoth like Google and Amazon, right. So why was I able to do it? And I think it was because how those people found, like, those potential clients found me, it wasn't me reaching out to them and pitching them my services. It was someone that they knew that was already working with me saying, you have to use Jared, right? This is like, Jared, not attitude at the time. You have to use Jared. He's made me so much money, trust me, right? And that goes. One of your friends telling you that versus a salesman telling you that. It just goes way further, right? And so, like, the day I met a potential new client, I already had that trust built up with them, right? And that confidence.

[Omar Khan]

Let's talk about events. Because one of the things that you do is invest in events to. To build the business, grow the business. But when you started telling me about what that meant for you, I was like, what?

[Jared Siegel]

Okay, this is where I've. Yeah, I mean, I've done a really good job of, like, integrating my personal passions and interests into attitude and getting my employees to love what I love, getting my clients to love what I love. Right? Um, early on, we would sponsor events, major events by different ad exchanges and publications that, like, focus on throwing events for our industry, right? I would get up on stage, you know, person seven of 25. I'd do my five minutes spiel. They would ask me questions that weren't even pertinent to me. I would get frustrated. Okay, this is a waste of money, right? And so a little bit on a whim, okay? I was actually flying to an event in early 2023, and on that plane, like, 25 people were going to the same event, right? And I started talking to him. I'm like, hey, guys, would you want to go to Disney with me this summer? Right? And they're like, what do you mean? I'm like, yeah, I think Attitude is going to host a golf tournament. I love golf. I love Disney World. I'm obsessed with Disney World. If everyone that knows me knows I'm obsessed. And they're like, yeah, that sounds cool, right? So I started Text Chain. This was in March, March of 23. About two weeks later, I had 15 people signed up. I'm like, awesome. I call up Disney, I reserve a ton of hotel rooms, I rent out some golf courses. And I. And I set all of this up. I set up dinners, steak dinners, everything. Me, like two employees and the rest clients, right? And we come back from it and we're. We're sending, you know, we're posting pictures on LinkedIn and all this kind of stuff. And the feedback that we got on social was like, why wasn't I invited? I wanted, right? And tons of people who I've never even met or heard of in our industry are like, I want to be part of this. I want. What is this? Right? And so I was like, well, my barbecues are always successful. This was successful. Maybe we should actually just double down and throw a ton of events. And so now 2024, we did what we call the attitude open. Five days, 40 something people, mostly clients, two or three sponsors at Disney World, four rented out restaurants for dinner, three rounds of golf a day in the parks, and I lead the whole thing. People follow me around. I'm obviously obsessed with Disney, so I know exactly where to go at what time and stuff, stuff like that. And so many people reached out that they want to sponsor it. And I was like, wait a second. We did this for a fraction of the cost of going to one event that one of our, one of these other companies throws. And we literally got these people in a room for four days in a hotel with us. Like, we literally spent every waking minute with these people. We're going to double down again, right? So 2025 this year we went nuts. 50 something people, really nice hotel, tons of like this shirt that I'm wearing, tons of swag given out and everything. Most of the people that came, we don't work with yet. Major, major, major publishers. And these are the decision makers at these companies, right? These are VPs and C level people at these companies. And we took them to Animal Kingdom, into Epcot and to two rounds of golf. Four dinners, boat cruises and all this kind of stuff. And we, and we organized and threw it all ourselves, right? It became big enough that I actually became a travel agent on the side just to throw these events for us. Right? I got my cruise line agency number and all of that kind of stuff.

[Omar Khan]

Wow. So it's funny because the idea of going on a vacation with somebody like a vendor is like, it's almost like a timeshare thing. You're like, do I really want to be stuck with them for a whole day where they're going to keep pitching me on the timeshare?

[Jared Siegel]

You better hope you like them.

[Omar Khan]

Yeah. Yeah. And so why do you think, like people who weren't even customers were coming? Was it because they, when you did take customers and then you're going on social and sharing this stuff and they're seeing, wait a minute, like this person from that company spent all of this time with you, plus it's fun because you're going to Disney World or Whatever. Do you think it was like that sort of social proof?

[Jared Siegel]

Yeah, I think they felt like, hey, these, these, this is, this looks fun. This looks cool. Why wasn't I invited? Like, what's this exclusive party that everyone gets to go to? And so that, that certainly worked well. But also, like, people, people like a little bit of a break from reality. Right. This is why I love Disney World specifically, like, it's literally its own world outside of the United States. It's like you're there, you suspend, you know, suspend disbelief. Everything is, everything is possible at Disney. And so blurred out, like a lot of adults really want to go there without their kids. Right. And this is, by the way, this is how I signed our, our very largest client. Without even meeting him. I invited him and his wife to meet me at Disney World with my wife and go on a four day vacation together. Thank God we liked each other, we got along. He's now, he's now one of my best friends. Right. And we hang out all the time, but it works. I do this kind of stuff all the time. If someone is worth, you know, a giant chunk of money in your pocket, you better make sure they feel, you know, loved and heard and respected. And what better way than taking them on vacation?

[Omar Khan]

And the silver lining is, even if you didn't like them, hey, you're in Disney World, right?

[Jared Siegel]

Yeah, what do we care? We're still at our favorite place on earth, so it's fine. Yeah, yeah.

[Omar Khan]

Love it. Let's talk about the transition. So you raised some, your Series A, you are, you know, you're now having investors, stakeholders, there's more conversations about how to scale the company, your role, how that needs to evolve, and so on. And at that point, you were still in the weeds, Right?

[Jared Siegel]

Right. And to some extent I still am, but.

[Omar Khan]

Yeah. And many founders, you know, when this is a baby, it's just like hard to let go. And I think like with your case, it was maybe, maybe an extreme example of that.

[Jared Siegel]

Yeah. So when I raised capital, I was doing the following. I was doing all invoicing, I was doing payroll, I was making sure that we were established in each state for tax reasons. Right. I was paying our taxes, I was doing most of the code releases, I was dealing with all sales, all contracts, like a lot of the business. Right. Like I would say 99%, but maybe 75% of the workload fell on me. Right. Then my CTO is probably taking 20 of the percent, the remaining percent, and then 5% across everyone else. Right. And giving up like that Responsibility. The reason it was so scary to me, and it's probably scary for any founder, is like, you don't want someone to make a mistake that costs you money. You know, you're doing a good job. It's what's making your business money. So God forbid you relinquish certain roles or responsibilities, someone else on their team and like you relinquish invoicing, right? And they send the wrong invoices or the wrong amounts and you don't make as much money as you should have. Like, okay, that's literally dollars out of your pocket, right? And so it took a very long time for me to work on that. I literally paid a management trainer for almost a year. I met every single week. And I would walk through with her different scenarios that were literally happening in my, you know, my quote unquote office, in my remote environment, in my business, with each member of my team. And she's like, even though she never met anyone else on the team, kind of knew who everyone was, right? Like, how should I handle this? What should I do here? This person is not meeting my expectations, like, what do I do? Right? And that was super helpful. But there's been like a recurring story in my life, my work life, which is, you know, some crazy external force happens and I have to make a major decision, right? And this is how I kind of started relinquishing some artifact. Early on in my career, my boss, who actually now works at Attitude, went away on vacation and everything blew up. So I had to learn how to code and I had to figure out how to make this money, right? And that's how my career kind of really took off. In 24, just a little over a year ago, I went on vacation. My wife was like, you're not working. Like, I want to actually enjoy this vacation. You're not going online. And so I met with my team a week before and I said, this is what you're going to do at the end of every day. Just send me an email with the updates, let me know what's going on. Just so I don't feel too far out of the loop, but you're not going to hear from me. I came back the next week. Business had grown, revenue was up, and I was like, I guess I can rely on these people, right? And that's kind of when the floodgates sort of opened. I started like relinquishing a ton of or offloading a ton of like my responsibilities, especially on like the business side, like the day to day operation side to Other members of my team. Some of the stuff like invoicing I still do because I'm a little crazy about that. But it's definitely gotten to the point where like, if I don't work today, we're fine, right? Unless there's an emergency, we're fine. It's a good place to be. It's a scary place to get to as a founder led business. But the only way to do it is to just rip the band aid off and go for it and hope that it works out. If it doesn't, okay, you come back and you fix things and you move on.

[Omar Khan]

But for people to really understand how hard it was to make that transition. Like at one point you hired a couple of people who you were going to start handing over to. And what did they do for the first three months?

[Jared Siegel]

Not much of anything because I was like too afraid to give them any real responsibility. So I had two people on the business side to support me, senior people, and they were probably working one hour a day on like menial tasks that I was handing off to them, right? And that's when the investors came in and said, like, what the heck are you doing, Jared? You got it. You gotta offload something. Like, this is ridiculous. You're doing some of this stuff. You're the CEO of the company. Get someone else to do it. Right? I'm like, oh, I can't, I can't, I can't. Right? Eventually I did. A few months later, they started ramping up really quickly. And now, honestly, their days are out of control and way too busy. And now they have to hire people to offload some of that work too.

[Omar Khan]

That's funny. All right, we should wrap up, so let's do the lightning round. I'm just going to ask you seven quick fire questions. Okay? What's one of the best pieces of business advice you've received?

[Jared Siegel]

Yeah. My mother, when I was applying for my first job, said, always be a revenue driver, not a cost driver. I was debating whether I should go into the marketing department of a company or the revenue department of the company. And she said, I don't even know what this is. Go in the revenue department, trust me. And it was a very smart move.

[Omar Khan]

Love it. What book would you recommend to our audience and why?

[Jared Siegel]

I don't really have a lot of time to read books. I'm so busy. Most of the books that I read are like crazy sci fi stuff to relieve my mind of what's actually going on in the day to day. So I probably don't have the best answer for that one.

[Omar Khan]

All right. What's one attribute or characteristic in your mind of a successful founder?

[Jared Siegel]

Someone that, that, that spends the time understanding each aspect of the business. Right. Like, it drives me nuts when I talk to other founders or executives at a company and they literally don't understand what their business does. If you ask me how a certain piece of code works that I've never seen before, I can go in and figure it out. Right. If you ask me about how this other business that we acquired, how every little aspect of their finances is run, I know everything. Right. And it's that we were like, no. Regardless of like what the issue is, I can always chip in.

[Omar Khan]

What's your favorite personal productivity tool or habit?

[Jared Siegel]

I have a very specific routine. I wake up at like pretty much the exact same time every day. Make my bed, take the shower. I go on my walk with my dog into town. Get the exact same cup of coffee from the exact same place. Like, my day pretty much every day for the last five years has been almost exactly the same. I have very few. Like, I don't have much of a variety of clothing. I don't want to spend time like thinking about what should I wear today? What should I do today? Like, I want to do the exact same thing. It might sound a little bit boring, but like, same way, like we're raising our child. She has the exact same routine every day and it helps her not be cranky and stuff like that. It helps as an adult as well.

[Omar Khan]

Yeah, yeah. Because we can get cranky too as well. What's a new or crazy business idea to pursue if you had the time?

[Jared Siegel]

Yeah. So everyone is obsessed with. Or it's maybe it's a little calming down now, but the idea of AI. Right. And like, okay, AI this, AI that. What I want to do is try to figure out how we can use whether it's like ChatGPT or one of these other tools and some machine learning to basically automate the actual innovation part of our business. We're spending so much. Everyone's thinking about how you automate the, the day to day part of your business. But like, that's what makes us successful. Right. And the second you start automating that or handing off a service as part of a business to a bot, like that's where things are going to fall apart. But we have all these ideas of, of things that we want to test within our products from a development perspective that we don't have the resources to do without us going out and hiring like 50 more engineers. Right. But that's where AI can't really help us is like, figuring out how to leverage that to build the new tech for us. Then our people can service.

[Omar Khan]

What's an interesting little fun fact about you that most people don't know?

[Jared Siegel]

Yeah. I don't know if it's fun, but, you know, I'm a very motivated, type a person with a very specific timeline. There's a very specific reason why. And I share this with my employees. I don't share this often, but when I was young, 23, 24 years old, I got diagnosed with multiple sclerosis, which is a disease that I'm lucky and fortunate enough. I have it under control, but it can debilitate you and it can make you immobile. Right. And when I got that diagnosis, I was in a position where, like, I don't know how many years I'm going to have to be a productive worker and to support my family. Right. And so, like, I'm going to take advantage of every minute that I have or I can to work my butt off to make sure that my family's taken care of. So I write a letter every year to all of my staff saying, like, this is why I'm pushing you so hard. This is what I'm personally trying to achieve for myself and for my family and for you guys. Right. And I have a very specific motivation. Wow.

[Omar Khan]

Wow. I love that in many ways, it's like, when you're pushing people and they know that there's this real personal thing behind you, it's like, okay, it's not just because he's a pain in the ass and wants us to work on.

[Jared Siegel]

Yeah. And honestly, maybe I use it to my advantage a little bit. Like, hey, guys, if I am Ms. And I can do it, you can definitely do it. Right.

[Omar Khan]

And finally, I think we know the answer to this. But finally, what's one of your most important passions outside of your work?

[Jared Siegel]

Yeah. So definitely my wife and I love to travel. We go to Disney a lot, but we travel every year. We try to go to one place internationally. We spent a few weeks in Italy a few summers ago. That was amazing. Disney World is. I'm obsessed. Go five to ten times a year.

[Omar Khan]

Five to ten times a year. Of course you do, because you're taking away your. Yeah, yeah.

[Jared Siegel]

We're taking our customers. Right. And golf. I'm obsessed with golf. I'm not nearly as good as I used to be. Played a little bit in college, but I find it very relaxing to. Again, it's an escape from reality. To walk the course for four and a half, five hours and not really think about the world around me and just be like, in nature. It's very nice.

[Omar Khan]

Love it. Awesome. Thanks, man. It's been a pleasure. I really enjoyed the conversation. It was fun. If people want to learn more about attitude, they can go to attitude.com. that's not attitude, but ad aditude. And if folks want to get in touch with you, what's the best way for them to do that?

[Jared Siegel]

It's just jaredtitude.com awesome.

[Omar Khan]

Thanks. It's been a pleasure and I wish you and the team the best of success.

[Jared Siegel]

Yeah, thanks for having me. It was awesome.

[Omar Khan]

My pleasure. All the best. Cheers.