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

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.

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.

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.

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."

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.

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."

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.

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."

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.

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."

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