Service-to-SaaS Strategy: Bootstrapping to $5M ARR | Aditude

Jared Siegal quit his job on a whim to start a consulting business, grew it to $2M in revenue, and then successfully pivoted it into a high-growth SaaS platform. He bootstrapped Aditude to over $5M in revenue before raising a $15M Series A. In this episode, Jared reveals the "Service-to-SaaS" playbook he used to transition from hourly billing to recurring revenue. He shares how he convinced a client to lend him an engineer for free to build the MVP, why he forced all customers to pay 100% upfront (creating negative working capital), and how he closes his biggest enterprise deals by taking prospects to Disney World instead of boring steak dinners. 🔑 Key Lessons 🚀 Service-to-SaaS Pivot: How to transition a $2M consulting firm into a scalable software business without losing revenue. 🛠️ The "Client-Funded" MVP: How Jared got a client to give him an engineer for 6 weeks for free to build the first version of the product. 💰 Cash Flow Strategy: Why he enforced a strict "Pay in Advance" policy to bootstrap to $5M without external capital. 🎢 Event-Led Growth: The unique strategy of hosting multi-day Disney World trips for prospects that converts better than traditional sales. 🧠 Founder Urgency: How a personal health diagnosis (MS) drives Jared's relentless focus on revenue over vanity metrics. 📖 Chapters Introduction and Favorite Quote Overview of Aditude's Product and Market Company Growth and Funding Journey Founder's Background and Early Career Transition to Consulting and Early Challenges Building the SaaS Product Client Relationships and Early Success Bootstrapping Challenges and Decision to Raise Capital Effective Fundraising Strategies Bold Outreach and Networking Targeting the Right Investors Referral-Based Growth Advance Payment Policy Event-Based Client Engagement Transitioning Leadership Roles Lightning Round: Business Insights This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services 📫 Mailtrap → Get 20% off with code THESAASPODCAST Resources: 🎧 Full Show Notes: saasclub.io/447 🎤 Subscribe to the Podcast: saasclub.io/subscribe 💌 Get weekly 5-minute SaaS insights: saasclub.io/email 💡 Join the SaaS Club founder community: saasclub.co/plus