I Spent 24 Hours With A SaaS Millionaire

Jeremy, a successful "solopreneur," built and sold a Software as a Service (SAS) business for millions. His journey began with a direct message, leading to a discussion of his "tentpole strategy," which he claims revolutionized software building. The speaker, Pat Walls, traveled to Los Angeles to meet Jeremy and learn more about this strategy, particularly in light of current discussions about SAS being "dead" due to AI and low-code tools. Jeremy's business, Taskmagic, focused on automating messy browser human behavior, going beyond the limitations of API-based tools like Zapier. As a solo founder, with the help of his CTO, he scaled Taskmagic to over 60,000 users and approximately 8,000 paying customers, sometimes generating over $400,000 per month and reaching about $3 million in annual revenue. This success led to Taskmagic making the Inc. 500 list. Jeremy decided to sell the business before turning 38, securing an offer in the mid-upper seven figures, which he described as life-changing. He explained his "tentpole strategy" as building a core product, like Taskmagic, and then creating other "side products" that funnel paid users to that main "tentpole" product. Instead of traditional marketing, these side products generate their own SEO lift and attract customers who then naturally upgrade or cross-sell into the main product. He showcased awards like the Product Hunt Golden Kitty Award and recognition from AppSumo, along with an Inc. 5000 magazine feature, as proof of Taskmagic's success. Jeremy started his journey as non-technical, initially "hacking away" at a slow, no-code app builder (V1) in 2019. Early monetization allowed him to hire his first employee, leading to a rebuild and launch in 2020, which achieved seven figures in revenue. In 2021, they shifted focus to automation, starting with a few hundred thousand dollars in revenue and growing to $3 million in three years. He elaborated on the tentpole strategy using Taskmagic as the core. Unlike traditional SAS marketing that might offer free information tools, his approach leverages modern no-code tools to sell functionality. The strategy involves: 1. **Building for the customer's next problem:** For Taskmagic's customers (business owners, agencies, freelancers needing sales), the next problem was outbound communication. 2. **Building something simple and specific:** They created "Mail Lead," a simple email outbound platform. Specificity helps with SEO; a tool like "cold outreach email for some sector" ranks faster than a general "automation" tool. Mail Lead generated almost seven figures in revenue on its own and attracted new customers. 3. **Ensuring a natural upgrade path:** Mail Lead users, after sending cold emails, might want to connect it to other apps, leading them to Taskmagic's automation features, creating a seamless upgrade. Jeremy also noted that Taskmagic offered lifetime deals and usage-based pricing to address customers' reluctance to pay constant subscription fees, which helped bankroll the business early on. 4. **Stacking an ecosystem:** Recognizing Mail Lead users needed leads, they built "Leadquest.ai," an AI tool for searching leads. This created another integration point, as users could then use Taskmagic to automate emailing leads from Leadquest.ai, and then purchase Mail Lead for mass emailing. This interconnected ecosystem allowed Mail Lead to achieve nearly seven figures, while Taskmagic gained more users from both Mail Lead and Leadquest.ai. Jeremy believes this approach, where mini-products cross-sell to each other, is the future of SAS, especially with the ease of creating products using modern tools. He emphasized that these are not separate side hustles but components serving the same ecosystem. If he were to start over, he would apply the same strategy, potentially making a product like Leadquest the new "tentpole." Discussing the sale of Taskmagic, Jeremy shared the emotional rollercoaster behind the seven-figure transaction. He aimed to exit before turning 38, driven by personal financial pressures, including a $9,000 monthly mortgage and having a young daughter. He explored brokers and listed the business on acquire.com, receiving over a hundred inquiries. However, the process involved buying out investors, which depleted both personal and business bank accounts, pushing him into significant personal debt ($50,000 on his Amex Platinum, plus another $200,000). This period was incredibly dark, with the fear of losing their home, and his daughter's room being his only source of calm. Ultimately, the sale brought millions into his bank account, shifting his focus to establishing a new daily routine. As advice for aspiring SAS founders, Jeremy highlighted the "toxically positive" online environment where struggles are often hidden. He encouraged founders to focus on problems, embrace bad days, and share their authentic experiences, rather than presenting a constantly "crushing it" facade. He believes that by following his tentpole strategy, even if it takes multiple products, cumulative success leading to seven figures is achievable. Pat Walls concluded by praising Jeremy as a "real deal" SAS millionaire, emphasizing that building a $3 million annual SAS business and selling it for millions in cash is a rare accomplishment. He noted that AI will change SAS, but Jeremy's strategy of treating products like content and creating an ecosystem of mini-products to help customers is a valuable lesson. He encouraged viewers to consider what kind of SAS ecosystem they could build.